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Influence of Cooking on Anthocyanins in Black Rice (Oryza sativa L. japonica var. SBR)
Abstract
The composition and thermal stability of anthocyanins in black rice (Oryza sativa L. japonica var. SBR) produced in California were investigated. Six anthocyanin pigments were identified and quantified by high performance liquid chromatography using photo diode-array detection (HPLC-PDA) and electrospray ionization mass spectrometry [LC-(ESI)MS/MS]. The predominant anthocyanins are cyanidin-3-glucoside (572.47 microg/g; 91.13% of total) and peonidin-3-glucoside (29.78 microg/g; 4.74% of total). Minor constituents included three cyanidin-dihexoside isomers and one cyanidin hexoside. Thermal stability of anthocyanins was assessed in rice cooked using a rice cooker, pressure cooker, or on a gas range. All cooking methods caused significant (P < 0.001) decreases in the anthocyanins identified. Pressure cooking resulted in the greatest loss of cyanidin-3-glucoside (79.8%) followed by the rice cooker (74.2%) and gas range (65.4%). Conversely, levels of protocatechuic acid increased 2.7 to 3.4 times in response to all cooking methods. These findings indicate that cooking black rice results in the thermal degradation of cyanidin-3-glucoside and concomitant production of protocatechuic acid.
... The main non-glycosides are cyanidin, peonidin, delphinidin, pelargonidin, petunidin, and malvidin. 31 The anthocyanin compounds in the seed coat of black rice accumulate in large quantities as it matures, ultimately producing a darker color with a content of up to 40%. 32 The name of black rice comes from its rich natural anthocyanin compounds. ...
... The loss rate of cyanidin-3-glucoside in black rice cooked in pressure cookers is the highest, up to 79.8%, followed by black rice cooked in electric cookers (74.2%) and gas cookers (65.4%). 31 Colasanto et al. 113 compared the effects of cooking techniques (boiling, microwave oven, under pressure pot, and risotto preparation) on the bioactive component in black rice and found that the risotto method is a more useful cooking technique for the retention of active substances such as anthocyanins and antioxidant activity, while the boiling method turned out to be the worst. Similarly, it was noted that the boiling method resulted in large reductions in the overall flavonoid and anthocyanin compositions of black rice. ...
... 119 The main reasons for the differences in polyphenol changes in black rice caused by different cooking methods are different cooking pressures and temperatures. 31 However, when cooking pressure and temperature are the same, the water-to-rice ratio can also cause varying degrees of polyphenol changes in black rice. Compared with black rice porridge, black rice cooked by the risotto method, which completely absorbs water, can better retain anthocyanins, flavonols, phenolic acids, and other active ingredients and even increase the content of soluble anthocyanins, 45 but the integrity of the macrostructure and internal structure of the cell of risotto is lower than that of black rice porridge. ...
Compared to brown and white rice, black rice contains more nutrients and numerous unique bioactive substances, such as essential amino acids, dietary fiber, γ-oryzanols, γ-aminobutyric acid, phenolic compounds, and anthocyanins, which makes it highly valuable for development and use. Whole-grain black rice typically requires a certain amount of processing prior to consumption, with the primary goal of enhancing the taste and texture of whole grains and their products. However, various new processing technologies have been effectively applied to the processing of black rice and the enhancement of its qualitative characteristics, but they also have both positive and negative effects on its nutritional quality. Therefore, evaluation of changes in concentrations of the bioactive substances as natural antioxidants due to processing and storage conditions is critical for establishing dietary guidelines for rice. This review highlights the primary bioactive components of black rice and provides a discussion of the impact of processing methods and storage on the bioactive components of black rice. Furthermore, we summarized the issues that currently exist in the processing and storage of black rice.
... However, excessive ultrasonic power had certain adverse effect on polyphenolic compounds [42], thereby decreasing the TAC of PBR as the power exceeded 360 W. The same observation was reported by Ć urko et al., who showed significant loss of total anthocyanins and total polyphenols of red wines at high ultrasonic power [44]. The high temperature and pressure caused by transient cavitation at high ultrasonic power could stimulate the pyrolysis of H 2 O, thus generating hydroxyl radicals and hydrogen radicals, which could act as oxidizing and reducing agents and react with phenolic compounds leading to loss of phenolic compounds [45,46]. Fig. 3 indicates that the free polyphenol content in PBR increased gradually with the intensification of ultrasonication and was then stabilized. ...
... As the typical anthocyanin of black rice, cyanidin-3-O-glucoside could be converted into cyanidin through deglycosylation during hydrothermal treatment, and cyanidin could be further degraded into protocatechuic acid and phloroglucinaldehyde by breaking chemical bonds, thereby increasing the content of free polyphenol of black rice [47]. The immersion water underwent alternating cycles of negative and positive pressure during the ultrasonic treatment; air bubbles were produced as the negative pressure exceeded the ambient pressure, and oscillating bubbles would generate high local temperature and pressure in the subsequent collapse [46]. Therefore, it could be inferred that the thermal effect of ultrasound-assisted immersion increased the content of free polyphenol in PBR by degrading anthocyanins. ...
Parboiling is gaining increasing attention as it can enhance the head rice yield (HRY) and nutritional quality of non-pigmented rice. The traditional parboiling process with high-temperature immersion requires a long immersion period and results in hard texture of cooked parboiled black rice (PBR), which may be addressed by ultrasound-assisted immersion. In this study, we evaluated the effect of power, time and temperature of ultrasonic immersion on the HRY, texture profile and nutritional quality of PBR. Proper ultrasound-assisted immersion could increase the HRY by about 20% and the GABA content by up to 133%, as well as reduce the arsenic and cadmium content by up to 61% and 79% relative to untreated black rice (UBR), respectively. Moreover, it could increase the content of essential minerals such as calcium, iron and zinc to some extent, and free and bound polyphenols, despite of a certain loss of anthocyanins. It could also improve the palatability of cooked rice. Furthermore, response surface experiments based on the Box-Behnken design were performed to obtain and validate the optimal conditions of ultrasound-assisted immersion (540 W, 45 min, 57 °C). On this basis, morphological changes might be one reason for the improved HRY, nutrition and texture of PBR compared with those of UBR, namely the disappearance of cracks near the aleurone layer and formation of new cracks in the interior of rice.
... e pericarp plays a protective color seed coat and has pigment, which makes rice appear brown, red, or black. Starch stores are majorly found in endosperm, which is about 75%, and proteins are found in an outer layer, which is sub-aleurone [47][48][49]. Mau et al. [50] believed that black rice contains lesser amounts of polysaccharides including dietary fibers (cellulose and hemicellulose, pectin, and resistant starch) and simple sugars. All these carbohydrates are mainly found in the outer layers. ...
... In Asia, particularly in China, a variety of black rice cultivars are grown [51]. When compared to white rice, black rice has better nutritional and functional properties. is is owing to the presence of several bioactive and nutritious components in the embryo and the bran layers, such as functional lipids, essential amino acids, vitamins (A, B complex, and E), dietary fiber, minerals (Fe, K, Zn, Mg, Cu, P, and Mn), phenolic compounds, anthocyanins, y-oryzanol, tocopherols, phytic acid, tocotrienols, and phytosterols [47][48][49]. Black rice's endosperm contains around 75% carbohydrates, mostly starch and a protein-rich outer layer (sub-aleurone). e maximum quantities of anthocyanin are found in black rice, which has a high nutritional value. ...
This review investigates black rice's photochemistry, functional properties, food applications, and health prospects. There are different varieties of black rice available in the World. The origins of this product can be traced back to Asian countries. This rice is also known as prohibited rice, emperor's rice, and royal's rice. Black rice is composed of different nutrients including fiber, protein, carbohydrates, potassium, and vitamin B complex. It contains an antioxidant called anthocyanin as well as tocopherols. Antioxidants are found mostly in foods that are black or dark purple. Due to its nutritious density, high fiber level, and high antioxidant content, black rice is a good alternative to white and brown rice. Utilizing black rice in various foods can enhance the nutritional value of food and be transformed into functional food items. Many non-communicable diseases (NCDs) can be prevented by eating black rice daily, including cancer cells, atherosclerosis, hypertension, diabetes, osteoporosis, asthma, digestive health, and stroke risk. This review aim is to discuss the role of nutritional and functional properties of black rice in the formation of functional food against different non-communicable diseases.
... The effects of germination on the concentrations of pigmented flavonoids often varies. Soaking rice in water for 1 h at room temperature had no effect or delivered inconsistent anthocyanin results (Hiemori, Koh, and Mitchell 2009), whereas germination under various conditions resulted in elevated levels of anthocyanins and proanthocyanidins (Maksup et al. 2018;Owolabi, Chakree, and Yupanqui 2019;Sutharut and Sudarat 2012). Occasionally, slight increases or decreases and/or inconsistent results have been found for total anthocyanin content and individual anthocyanins (Hiemori, Koh, and Mitchell 2009;Yodpitak et al. 2019). ...
... Soaking rice in water for 1 h at room temperature had no effect or delivered inconsistent anthocyanin results (Hiemori, Koh, and Mitchell 2009), whereas germination under various conditions resulted in elevated levels of anthocyanins and proanthocyanidins (Maksup et al. 2018;Owolabi, Chakree, and Yupanqui 2019;Sutharut and Sudarat 2012). Occasionally, slight increases or decreases and/or inconsistent results have been found for total anthocyanin content and individual anthocyanins (Hiemori, Koh, and Mitchell 2009;Yodpitak et al. 2019). The effect of germination on anthocyanins and antioxidant activity in two purple rice varieties was examined (Sutharut and Sudarat 2012). ...
Over the last 30 years, thousands of articles have appeared examining the effects of soaking and germinating brown rice (BR). Variable germination conditions and methods have been employed to measure different health-beneficial parameters in a diverse germplasm of BR. Research results may therefore appear inconsistent with occasional anomalies, and it may be difficult to reach consensus concerning expected trends. Herein, we amassed a comprehensive review on germinated brown rice (GBR), attempting to codify 133 peer-reviewed articles regarding the effects on 164 chemical parameters related to health and nutrition in BR and in value-added food products. The Preferred Reporting Items for Systematic Reviews and Meta-Analyses (PRISMA-2020) approach was used to direct the flow of the literature search. A pair-wise comparison t-test was performed to deliver an overall approach indicating when a given compound has been found to significantly increase or decrease through germination, which was grouped into GABA and polyamines, γ-Oryzanol and phytosterols, phenolic compounds, vitamins, proteins and amino acids, starchy carbohydrates, free sugars, lipids, minerals and phytic acid. This resource will stimulate interest in germinating rice and optimistically help increase both production and consumption of highly nutritious, health-beneficial rice with pigmented bran.
FULL TEXT LINK: https://www.tandfonline.com/eprint/IV4E8UGZBT6J45MCEYWW/full?target=10.1080/10408398.2022.2094887
... Moreover, a significant decrease in the total contents of cyanidin-3-glucoside and peonidin-3-glucoside (p<0.05) was reported in the black rice grains during roasting, soaking, and steaming (Wu et al., 2013). In addition, the total anthocyanin and cyanidin-3-glucoside was decreased by thermal cooking (Bhawamai et al., 2016), and cyanidin-3-glucoside was predominantly found to have protocatechuic acid during roasting (Hiemori et al., 2009). ...
... 5.12±0.35 to 8.47 ± 0.28, 6.80 ± 0.46 mg CAE/g dry weight, respectively (p ≤ 0.05) (Figure 2). Cyaniding-3-glucoside could be degraded to phloroglucinaldehyde and protocatechuic acid in the thermal process (Hiemori et al., 2009;Ito & Lacerda, 2019). This indicated that the decrease of the anthocyanin content observed here was plausibly due to its degradation upon roasting. ...
Abstract The effects of roasting on the colour parameters, anthocyanin content, total polyphenol content, antioxidant activity, γ-aminobutyric acid (GABA) content, and the microstructure of germinated Thai black rice (GTBR: non-waxy) and germinated Thai black sticky rice (GTBSR: waxy) were appraised. The results revealed that both types of roasted germinated Thai black rice showed an increase in all lightness (L*), redness(a*) and yellowness (b*). For the chemical properties, only the concentration of anthocyanin slightly decreased, whereas the total polyphenol content, ABTS+ radical scavenging activity, and GABA content markedly increased after roasting. Moreover, images of a scanning electron microscope (SEM) displayed that both germinated black rice grains became more compact and had a tight shape in the surface structure. Additionally, small pores were found in the GTBR and large pores were present in the GTBSR rice kernel when compared with the unroasted black rice in the internal structure. Together,the roasting process was capable of enhancing the GABA and phenolic contents, and antioxidative capacity in both the GTBR and GTBSR.
... Red kidney beans exhibit a substantial content of cyanidin-3-glucoside, while peanuts display variable amounts of this compound. Lentils contain approximately 0.66 mg of delphinidin-3-glucoside, and in black rice, cyanidin-3-glucoside is relatively low, but peonidin-3-glucoside is notably higher (Table 1) [33][34][35][36]. ...
... The cooking method also affects the overall nutritional content of the prepared product. The thermal stability of the anthocyanin and starch in black rice was assessed by different cooking methods by Hiemori et al. (2009) who found that pressure cooking caused more anthocyanin loss than that of rice cooker and direct gas. The milling and sieving fraction of the black rice starch also affects the protein and phytochemical fractions hence affecting the final nutritional content and the quality of the cooked product (Bolea et al., 2019). ...
The nutritional and functional quality of starch in black rice cultivars varies differently with different landraces for which efforts should be made to maintain the geographic identity, value chain, and utilization of the same. Black rice starch is found to have a better physicochemical and nutritional profile in terms of its thermal, rheological, and presence of bioactive compounds as compared to conventional starch sources such as white rice and wheat. It has more resistant starch content and the starch profile tends to have a bit longer cooking time, moderate gruel solid loss, low water uptake ratio, and swelling capacity while cooking. In this chapter, the nutritional, physicochemical characteristics, functionality, isolation, modification, and applications of black rice starch have been studied in detail with a focus on Indian black rice.
... The quantity and stability of ascorbic acid in extracts suggests that sorghum leaf sheaths have the potential to supply a substantial amount of vitamin C to the foods they are used to prepare [41,42,43]. Table 2 shows the correlation between the different variables. ...
Sorghum bicolor leaf sheaths are a common dried ingredient used as a colourant for waakye, a popular Ghanaian dish made from rice and cowpea. The leaf sheaths are also used in traditional medicine due to its impressive bioactive composition. Its potential as a natural food colourant and antioxidant has been established but the effect of different processing conditions on the physicochemical composition and characteristics have not been adequately researched. The present study assessed the effect of size reduction (whole, coarse and fine), temperature (room temperature (28°C) and 98°C) and time (20, 40 and 60 min) on the colour, pH and ascorbic acid content of sorghum leaf sheaths. Samples were steeped in a measured amount of water and analysis conducted on the extracts. Size reduction significantly reduced the lightness (l*) and colour intensity (chroma and hue) of extracts steeped at both temperatures. The pH of all extracts was relatively neutral, ranging from 6.63 to 7.23 and was not significantly affected by size reduction or time. Extraction of ascorbic acid was more effective at 98°C and did not degrade with constant heating within the experimental time. Average ascorbic acid content of extracts was 3.89 g/L. For effective utilization and value addition of Sorghum bicolor leaf sheaths, food producers should consider fine milling and late incorporation into food for optimum colour and phytochemical content preservation.
... Anthocyanins are considered a cornerstone of red wine quality, as they not only provide the red pigment, but also interact with other compounds in the red wine matrix, leading to changes in tannin and sensory characteristics. Work over the last 15 years has shown that anthocyanins are susceptible to degradation at elevated temperatures, leading to the loss of color through the breaking of covalent bonds in the flavonoid (Hiemori, Koh, and Mitchell 2009). Moreover, it has been shown that transcriptionally, grapevines grown in higher temperatures have lower overall biosynthesis of anthocyanins, leading to a net decrease in concentration at harvest (Yan et al. 2020). ...
... According to Lee [61], the average content of anthocyanin-3-glucoside was 45.52 mg/100 g, while paeoniflorin-3-glucoside was 3.22 mg/100 g. Hiemori et al. [62] determined that raw black rice contains 0.57 0.02 mg/g dw cyanidin-3-glucoside and 0.029 0.002 mg/g dw peonidin- Table 3 Effect of ultrasound-assisted hot-air drying on selenium-enriched germinated black rice regarding phenolic profile, flavonols, and anthocyanins. 3-glucoside. ...
Black rice is a functional food due to its higher protein, fiber, iron, antioxidant compounds, and other health benefits than traditional rice. The ultrasonic (US) pretreatments (10, 20, and 50 min) followed by hot-air drying (50, 60, and 70 °C) were applied to study the drying kinetics, mathematical modeling, thermodynamics, microstructure, bioactive profile, volatile compounds and to lock the nutritional composition of selenium-enriched germinated black rice (SeGBR). Ultrasonic-treated samples exhibited a 20.5% reduced drying time than control ones. The Hii model accurately describes the drying kinetics of SeGBR with the highest R2 (>0.997 to 1.00) among the fifteen studied models. The activation energy values in US-SeGBR varied from 3.97 to 13.90 kJ/mol, while the specific energy consumption ranged from 6.45 to 12.32 kWh/kg, which was lower than untreated. The obtained thermodynamic attributes of dried black rice revealed that the process was endothermic and non-spontaneous. Gallic acid, kaempferol, and cyanidin 3-glucoside were present in high concentrations in phenolics, flavonoids, and anthocyanins, respectively. The HS-SPME-GC-MS investigation detected and quantified 55 volatile compounds. The US-treated SeGBR had more volatile compounds, which may stimulate the release of more flavorful substances. The scanning electronic micrograph shows that the US-treated samples absorbed high water through several micro-cavities. Selenium concentration was significantly higher in US-treated samples at 50 °C than in control samples. In conclusion, ultrasound-assisted hot-air drying accelerated drying and improved SeGBR quality, which is crucial for the food industry and global promotion of this healthiest rice variety.
... Especially, anthocyanin-rich extracts from black rice varieties demonstrated capacity to decrease the levels of ROS, cell viability, and/or increase apoptosis and cellular antioxidant efficacy (Boonyanuphong & Tobgay, 2022;Liang et al., 2019;Moirangthem et al., 2021;Tyagi et al., 2022) ( Table 2). Black rice is a high source of C3G and peonidin-3-O-glucoside (P3G), however, further experimental studies should consider using it raw, as cooking promotes a great loss of total anthocyanins, from 60 to 80%, depending on the method used (Hiemori et al., 2009). Although poorly disclosed, the studies mentioned in this section probably used raw vegetable fractions in order to maintain high levels of anthocyanins. ...
Colorectal cancer (CRC) is the second most lethal and the third most diagnosed type of cancer worldwide. More than 75% of CRC cases are sporadic and lifestyle-related. Risk factors include diet, physical inactivity, genetics, smoking, alcohol, changes in the intestinal microbiota, and inflammation-related diseases such as obesity, diabetes, and inflammatory bowel diseases. The limits of conventional treatments (surgery, chemotherapy, radiotherapy), as demonstrated by the side effects and resistance of many CRC patients, are making professionals search for new chemopreventive alternatives. In this context, diets rich in fruits and vegetables or plant-based products, which contain high levels of phytochemicals, have been postulated as complementary therapeutic options. Anthocyanins, phenolic pigment responsible for the vivid colors of most red, purple, and blue fruits and vegetables, have been shown protective effects on CRC. Berries, grapes, Brazilian fruits, and vegetables such as black rice and purple sweet potato are examples of fruits and vegetables rich in anthocyanins, which have been able to reduce cancer development by modulating signaling pathways associated with CRC. Therefore, this review has as main objective to present and discuss the potential preventive and therapeutic effects of anthocyanins present in fruits and vegetables, in plant extracts, or in their pure form on CRC, taking into account up-to-date studies. Additionally, a highlight is given towards the mechanisms of action of anthocyanins on CRC.
... Although 90% of black rice production is in Asia, some studies showed the expansion of this product. Studies using black rice grown in different countries were reported in the literature: USA (Hiemori, Koh, and Mitchell 2009;Laokuldilok et al. 2011), France (Pereira-Caro et al. 2013); Italy (Melini et al. 2019), Russia (Tumanian et al. 2020;Zelenskaya et al. 2018), Brazil (Dittgen et al. 2019;Fernandes et al. 2021), and Australia (Callcott et al. 2018). ...
Recently, growing demand for products enriched with natural compounds that support human health has been observed. Black rice, its by-products, and residues are known to have in their composition a large amount of these compounds with biological potential, mainly anthocyanins. These compounds have reported effects on anti-obesity, antidiabetic, antimicrobial, anticancer, neuroprotective, and cardiovascular disease. Therefore, the extract from black rice or its by-products have great potential for application as ingredients in functional foods, supplements, or pharmacological formulations. This overview summarizes the methods employed for the extraction of anthocyanins from both black rice and its by-products. In addition, trends in applications of these extracts are also evaluated regarding their biological potential. Commonly, the extraction methods used to recover anthocyanins are conventional (maceration) and some emerging technologies (Ultrasound-Assisted Extraction - UAE, and Microwave-Assisted Extraction - MAE). Anthocyanin-rich extracts from black rice have presented a biological potential for human health. In vitro and in vivo assays (in mice) showed these compounds mainly with anti-cancer properties. However, more clinical trials are still needed to prove these potential biological effects. Extracts from black rice and its by-products have great potential in applying functional products with beneficial characteristics to humans and reducing agro-industrial residues.
... Based upon these results the samples were taken for further processing. It is observed that among the cooked extracts (steaming, boiling and microwave) of rice and millet varieties, the polyphenol content significantly decreased after cooking when compared to uncooked extracts ( Figure: 2a, 2b) The total polyphenolic and flavonoid content of rice and millets decreased drastically which is comparable with the study of Hiemori et al. (Hiemori, Koh and Mitchell, 2009). It was reported that the thermal processing cause significant destruction of phenolics which was attributed to their decomposition or degradation into other products as well as vaporization during cooking. ...
Industrial pollutants in vast amounts have been introduced into the natural domain. Microorganisms of
soil and water can easily degrade an enormous amount of these effluents. The removal of these xenobiotic
compounds is generally sluggish, and they appear to persist in the atmosphere. Because of their high
toxicity, their aggregation will trigger serious environmental issues. Purpose of these studies to degrade the
pollutants from the pharmaceutical industrial effluents. The optimum shaking velocity, inoculum volume,
concentration, and pH were determined. Several approaches are still in use to clean up the atmosphere
from these types of toxins, but the majority of they are expensive and impossible to achieve optimal results.
Biodegradation is now an efficient and cost-effective biotechnological solution for degrading harmful
contaminants from an industrial effluent. DNA fragments of resistant isolates were amplified using the
518F/800R primers. The BLAST tool was utilized for the sequencing of 16S rRNA. Various sequencing
were done utilizing MUSCLE 3.7. For tree rendering and phylogenetic analysis, PhyML 3.0 aLRT program
and TreeDyn 198.3 have been utilized. Usage of bacterial culture shows maximum removal of pollutants
200rpm and maximum removal of pollutants which was identified in 500 ppm at 40 ml culture volume.
... Based upon these results the samples were taken for further processing. It is observed that among the cooked extracts (steaming, boiling and microwave) of rice and millet varieties, the polyphenol content significantly decreased after cooking when compared to uncooked extracts ( Figure: 2a, 2b) The total polyphenolic and flavonoid content of rice and millets decreased drastically which is comparable with the study of Hiemori et al. (Hiemori, Koh and Mitchell, 2009). It was reported that the thermal processing cause significant destruction of phenolics which was attributed to their decomposition or degradation into other products as well as vaporization during cooking. ...
... Oryza sativa There are wide varieties of red and black rice that produce coloured pigments. The dark purple colour of black rice is contributed by the presence of anthocyanin in its pericarp layers (Hiemori et al., 2009). Black rice contains anthocyanins in free forms, which account for 99% of its total anthocyanin (Shao et al., 2014). ...
Background: Many histological stains cause health hazards to technicians, pathologists, and researchers. The hazard-free and eco-friendly natural anthocyanins have the potential to be a new source for histological stains. This study aims to systematically review the use of plant products containing anthocyanin for histopathological diagnosis. Methods: A comprehensive literature search was done using suitable keywords on Wiley, PubMed, Scopus, Google Scholar, and Web of Science databases. A total of 30 articles were selected for systematic review, where data obtained from the studies were tabulated. Results: About 90% of the reviewed studies have proven that anthocyanin-containing plant products may be used as natural stains. Out of the 30 studies, 49% involved the use of Hibiscus extract, 11% utilised mulberry extract, 9% utilised pomegranate, another 9% involved rose, and the remaining ones utilised black plum, black rice, butterfly pea, the flame of woods, onion skin, and red poppy extracts. Almost 40% of the studies concluded that aqueous extracts are superior to alcohol ones, and 46% used either iron or alum as mordant. Conclusion: Natural stains containing anthocyanin could be a better alternative to synthetic histological stains. Further extensive studies should be conducted to observe the use of these stains in pathological diagnosis.
... The amount of GABA can be significantly reduced during the SS drying of brown rice by increasing the SS temperature or processing time (Cheevitsopon & Noomhorm, 2015;Sootjarit et al., 2011). During the SS processing of rice to reduce its cooking time, ferricreducing antioxidant power and total phenolic content are reduced because of thermal degradation and leaching of water-soluble antioxidant compounds (Hiemori et al., 2009;Lisa et al., 2018;Piyawanitpong et al., 2018). Some cultivars of rice contain mainly cyanidin-3-O-β-glucoside, which is highly sensitive to heat (Sompong et al., 2011), resulting in the reduced antioxidant activity of these cultivars of rice when dried using SS (Rumruaytum et al., 2014). ...
The concept of superheated steam (SS) was proposed over a century ago and has been widely studied as a drying method. SS processing of cereals and cereal products has been extensively studied in recent years for its advantages of higher drying rates above the inversion temperature, oxygen‐free environment, energy conservation, and environmental protection. This review provides a brief introduction to the history, principles, and classification of SS. The applications of SS processing in the drying, enzymatic inactivation, sterilization, mycotoxin degradation, roasting, and cooking of cereals and cereal products are summarized and discussed. Moreover, the effects of SS processing on the physicochemical properties of cereals and the qualities of cereal foods are reviewed and discussed. The applications of SS for cereal processing and its effects on cereal properties have been extensively studied; however, issues such as the browning of cereal foods, thermal damage of starch, protein denaturation, and nutrition loss have not been comprehensively studied. Therefore, further studies are required to better understand the mechanism of the quality changes caused by SS processing and to expand the fields of application of SS in the cereal processing industry. This review enhances the understanding of SS processing and presents theoretical suggestions for promoting SS processing to improve the safety and quality of cereals and cereal products.
... As expected, cooking significantly decreased total anthocyanins content. Thermal degradation of anthocyanins was also observed in black rice cooked with three different methods (Hiemori et al., 2009). Zaupa et al. (2015) found that the thermal treatments significantly affected the total anthocyanins content, with their reduction of 30% and 64% in risotto and boiled rice, respectively. ...
In this chapter, an overview of the results related to the food applications of colored cereals such as black, blue, purple, pink and red maize, rice, wheat, barley, oat, sorghum and millet is presented. Anthocyanins are the largest group of pigments in cereal synthesized in grain outer layers i.e. pericarp and/or aleurone. Interest in anthocyanin-rich cereals has intensified because of their possible health benefits. Anthocyanins have demonstrated antioxidant potential in both in vitro and in vivo studies and the consumption of foods high in anthocyanins has been linked to lower risks of chronic diseases such as diabetes, cancer and cardiovascular disease. Rich in anthocyanin, colored cereals can be used as functional food ingredients, dietary supplements and sources of natural food colorants in the food and beverage industry that will be discussed in this chapter.
... The results imply that sprouting time positively affected the total flavonoid content of sorghum samples. Loss or gain in total flavonoids due to treatments could be attributed to a treatment type, nature of the food material and forms of the flavonoids present in the plant material (Prasanna et al., 2018;Hiemori et al., 2009). The increase in the total flavonoids with an increase in sprouting time might be related to its release as a result of enzyme activities from intracellular macromolecules such as carbohydrates and protein and altered cell wall structures (Prasanna et al., 2018). ...
This study assessed the effects of sprouting and fermentation on total phenolic content, total flavonoid content and antioxidant property of pearl millet (Pennisetum glaucum) and sorghum (Sorghum bicolor). Pearl millet and sorghum were subjected to the treatment of sprouting and fermentation for 0 h, 24 h, 48 h, 72 h and 96 h. After each of the treatments, the samples were oven-dried at 60 oC for 24 h and milled into fine flour of 0.05 mm in size. The total phenolic content, flavonoid content and antioxidant capacities were quantified using standard methods. The results of the study revealed that sprouting significantly (p<0.05) increased the total phenolic, total flavonoid and antioxidant capacities of pearl millet and sorghum. However, sprouting time significantly (p<0.05) reduced the total phenolic content of pearl millet. A similar trend of increment was observed in fermentation where there was a significant (p<0.05) increase in the total phenolic, total flavonoid, reducing the power and antioxidant capacities of pearl millet and sorghum with an increase in fermentation time. Therefore, the results of this study revealed that the two bioprocesses (sprouting and fermentation) significantly increased the total phenolic, total flavonoid and antioxidant capacities of pearl millet and sorghum. However, pearl millet exhibited reduced TPC with an increase in sprouting time.
... Besides, these rice varieties are rich in antioxidants that aid in preventing allergies, inflammations, and cancer; they are also recognized to play a prominent role in weight loss and weight management. The major bioactive compound responsible for the color in the pigmented rice is anthocyanin [5]. Apart from that, Vichapong et al. [6] observed the presence of various phenolic compounds in the pigmented rice. ...
The extent of starch hydrolysis and glycemic index (GI) of foods depends on how it is orally processed, but many in vitro digestion studies failed to consider the oral phase of digestion. This research aimed to understand the relationship between oral mastication and GI of rice. For this study, different rice varieties (pigmented and non-pigmented) were selected and analyzed for their physicochemical properties. The amylose content for all rice varieties was higher than 25%, with the starch content of 68.68 ± 0.70%-81.60 ± 1.78%. Temporal dominance of sensation was determined for rice samples to understand the consumers' sensory preferences towards the pigmented rice varieties. In vivo oral mastication studies were also performed for the rice varieties, in which significant differences were observed amongst pigmented and non-pigmented rice samples. The particle size for pigmented rice varieties after in vivo oral mastication was significantly larger (50% particles greater than 2 mm; due to its intact morphology) than non-pigmented rice. The significant impact of oral processing on the GI of rice irrespective of the varieties was also observed in this study. Thus, this research sheds light on the need for oral processing for in vitro digestion studies.
... The content of anthocyanin 3-glycoside in colored rice obtained by a pressure cooker was lower than that of cooked rice processed by a rice cooker and a gas range. Nevertheless, the increase of protocatechuic acid content was observed in these cooking methods [29]. Under thermal conditions, major anthocyanins can be degraded to anthocyanidin aglycones and produce several phenolic acids upon their structures. ...
Purple rice has gained attention for its health promoting potential due to a high content of bioactive phytochemicals. The heat generated during cooking alters the quality and quantity of nutrients and phytochemicals in food. This study aimed to investigate the phytochemical profile and chemopreventive properties of cooked glutinous purple rice using cell-based assays and a rat model. Purple rice was cooked in a rice cooker and was then further extracted with solvents to obtain dichloromethane and methanol extracts. The methanol extracts of glutinous purple rice contained great amounts of phenolics, flavonoids, and anthocyanins. Protocatechuic acid (2.26–5.40 mg/g extract) and cyanidin 3-glucoside (34.3–65.7 mg/g extract) were the major phenolic acid and anthocyanin contents, respectively. After cooking, the content of anthocyanins, γ-oryzanols, and phytosterols decreased, while the amount of some phenolic acid and tocol contents increased. Methanol extracts of glutinous purple rice inhibited reactive oxygen species production about 60% in PMA-treated peripheral blood mononuclear cells, reduced nitric oxide formation in LPS-induced RAW 264.7 cells (26–39% inhibition), and exhibited antimutagenicity against several mutagens using the Ames test, but dichloromethane extracts presented only mild anti-inflammatory activities. Although methanol extracts induced mild mutagenicity (mutagenic index 2.0–2.5), they did not induce micronucleated hepatocyte formation and certain hepatic CYP450 isozyme activities in rats. However, the mutagenicity of the methanol extract significantly declined after cooking. In summary, the methanol extract of the cooked glutinous purple rice might be a promising cancer chemopreventive fraction, which was neither genotoxic nor posing adverse effects on phytochemical–drug interaction in rats.
... Southeastern Asian countries are the primary producer of black rice. Recently, California also produces black rice due to high market demand [90]. European countries that cultivate black rice are Italy and Greece [23]. ...
Rice (Oryza sativa L.) is the primary staple food for half of the world population. It is generally classified based on the grain color into black, red, purple, brown, green, and white. These colored rice are determined by the composition and concentration of anthocyanin pigments in different layers of aleurone, pericarp, and seed coat. Anthocyanins are also accumulated in various tissues of the rice plants, mostly in the grain, but are also presents in leaves, leaf sheath, floral organ, and hull. The type and concentration of the anthocyanins in rice tissues are influenced by the cultivars and developmental stages. Anthocyanin-enriched rice is related to the health effects, including antioxidant, antibacterial, and anti-inflammation activities that potentially use as functional food ingredients, dietary supplements, and natural colorants. Structural and regulatory genes are involved in anthocyanin biosynthesis of rice. Various molecular biology techniques have been applied to improve productivity, nutritional contents, and market value of pigmented rice. This review focused on the genetics, biochemistry and biophysical analysis of anthocyanin in rice that will facilitate rice breeding program to develop new high-yield pigmented rice varieties.
... As expected, cooking significantly decreased total anthocyanins content. Thermal degradation of anthocyanins was also observed in black rice cooked with three different methods (Hiemori et al., 2009). Zaupa et al. (2015) found that the thermal 4.2 Food applications treatments significantly affected the total anthocyanins content, with their reduction of 30% and 64% in risotto and boiled rice, respectively. ...
... Overall, 17 products (55%) were adulterated with Oryza sativa (black rice), which is based on the detection of peonidin 3-O-glucoside (17) and relatively high concentrations of cyanidin 3-O-glucoside (3) in these samples, although other potential adulterants (e.g., purple wheat, black soybean) contain these two anthocyanins in similar proportions. The main compounds of O. sativa are 3 and 17 (Hiemori et al., 2009;Yawadio et al., 2007). Compound 17 was detected only in the seed of Oryza sativa samples but in none of the authentic Sambucus species that were analyzed in this study. ...
This work was initiated to develop a simple, quick, and reliable UHPLC-PDA-MS method to identify chemical markers for authentication and compare fruit samples of four elder species, Sambucus nigra, S. ebulus, S. canadensis, and S. cerulea. The UHPLC method showed an adequate separation of 11 compounds including anthocyanins, phenolic acids, and flavonoids in berries of the four Sambucus species. Quantification, detection limits, precision, accuracy as well as robustness were determined. The analysis of 55 different samples of four Sambucus species showed distinct phytochemical fingerprints. Thirty-one dietary supplements claiming to contain S. nigra berries extract were analyzed to determine authenticity. Ten (32%) of the 31 products complied with the label and contained only elderberry. The application of UHPLC-QToF provided useful information to characterize seventy-three compounds that can be used to distinguish among the four Sambucus species and also help to determine the presence of adulterants. Extracts of black rice (Oryza sativa) were identified as the main adulterants in the dietary supplements, although other undeclared ingredients such as extracts of purple carrot (Daucus carota ssp. sativus var. atrorubens) and flowers of S. nigra were also found instead of elder berry in two products. In addition to the detection of adulterated samples based on a comparison of the chemical profiles of anthocyanin and flavonoids, the developed methods can also be useful for the quality assessment of both bulk raw material and dietary supplements.
... This value gradually decreased to 305.78 ± 0.52, 217.58 ± 0.92, 204.40 ± 0.58, and 182.31 ± 0.58 mg cyanidin-3glucoside equivalent/100 g when black rice went through milling process of 15, 30, 60, and 90 min. Based on the HPLC and LC-MS chromatograms of acidified methanol anthocyanin extracts of black rice (Supporting information Figure S3), the major anthocyanin found in black rice used in this study was cyanidin-3-glucoside. Several previous studies have confirmed the prominent anthocyanin component in black rice is cyanidin-3-glucoside (Hiemori, Koh, & Mitchell, 2009), which is in consistent with the results from current study. The cyanidin-3glucoside content in original black rice was 140.97 ± 0.26 μg/g. ...
This work attempted to obtain miscellaneous black rice particles through directly modifying black rice using media mill, and develop milled black rice particles stabilized Pickering emulsions with intrinsic antioxidation functionalities. Particle size of milled black rice particles was reduced sharply from over twenty micrometers to 773 nm after only 90 min of milling. Slight degradation of some sensitive bioactive compounds (such as cyanidin-3-glucoside) occurred during milling process. While the bound phenolics (e.g. protocatechuic acid, ferulic acid) were well retained. Milled black rice particles exhibited good free radical scavenging activity. These milled black rice particles exhibited ability to form Pickering emulsions with good storage and heating stability. Besides, these Pickering emulsions possessed enhanced lipid antioxidation. This study offers a facile strategy to develop food-grade Pickering emulsions with intrinsic antioxidant properties by directly modify black rice as complex particulate emulsifiers through media milling process.
... Treatment of human and murine adipocytes with these derivatives showed that the compound mimicked insulin-like properties, enhancing Glut4 translocation and aiding PPARγ expression [127]. Similarly, polyphenols are also found in rice brans like ferulic acid, protocatechuic, sinapic acid and pigmented rice brans are rich in AcNs and pro-AcNs like C3G and PCA [128]. Rice bran is well known to exert antioxidant and anti-diabetic properties [129,130]. ...
Compromised carbohydrate metabolism leading to hyperglycemia is the primary metabolic disorder of non-insulin-dependent diabetes mellitus. Reformed digestion and altered absorption of carbohydrates, exhaustion of glycogen stock, enhanced gluconeogenesis and overproduced hepatic glucose, dysfunction of β-cell, resistance to insulin in peripheral tissue, and impaired insulin signaling pathways are essential reasons for hyperglycemia. Although oral anti-diabetic drugs like α-glucosidase inhibitors, sulfonylureas and insulin therapies are commonly used to manage Type 2 Diabetes (T2D) and hyperglycemia, natural compounds in diet also play a significant role in combating the effect of diabetes. Due to their vast bioavailability and anti-hyperglycemic effect with least or no side effects, polyphenolic compounds have gained wide popularity. Polyphenols such as flavonoids and tannins play a significant role in carbohydrate metabolism by inhibiting key enzymes responsible for the digestion of carbohydrates to glucose, viz. α-glucosidase and α-amylase. Several polyphenols such as resveratrol, epigallocatechin-3-gallate (EGCG) and quercetin enhanced glucose uptake in the muscles and adipocytes by translocating GLUT4 to plasma membrane mainly by the activation of the AMP-activated protein kinase (AMPK) pathway. This review provides an insight into the protective role of polyphenols in T2D, highlighting the aspects of insulin resistance.
... C3G concentration of the tested samples was calculated by using standard calibration curve (y = 20784x + 286223, R 2 = 0.9992) which is applied to this present study, and units of C3G were expressed in ppm (mgKg À1 ). UFLC peck of anthocyanins specifically C3G compound in raw rice was monitored at 520 nm and cooked rice was monitored at 280 nm according to Hiemori et al, 2009 (Table 4). ...
... C3G concentration of the tested samples was calculated by using standard calibration curve (y = 20784x + 286223, R 2 = 0.9992) which is applied to this present study, and units of C3G were expressed in ppm (mgKg À1 ). UFLC peck of anthocyanins specifically C3G compound in raw rice was monitored at 520 nm and cooked rice was monitored at 280 nm according to Hiemori et al, 2009 (Table 4). ...
Background
Black pericarp rice has recently become popular among rice consumers for its diverse health benefits specially anti-cancer effect. Cyanidin-3-Glucosides (C3G), an prominant bioactive component of anthocyanins which is abundantly present in black pericarp rice.
Objectives
We investigated, how effectively it can be used to fortify Cyanidin-3-Glucosides (C3G) content in red and white pericarp polished rice or rice based bakery products for more nutritional value.
Method
In the present study, we have characterized several black pericarp rice cultivars along with some red pericarp and white pericarp rice cultivars by physicochemical including mineral profiling, and quantified the C3G by UFLC and LCMS.
Results
C3G content was significantly reduced from raw rice to cooked rice condition. All the black pericarp rice cultivars synthesized C3G, while this content was not detected in red and white pericarp rice cultivars. However, when 25% of black pericarp rice were mixed with 75% red or white pericarp polished rice, C3G content was significantly retained in cooked rice conditions. Formulation of rice-based bakery food product using black pericarp rice powder was also remarkably retained the C3G content as compared to that of cooking. Black rice is harder in texture, difficult to digest and needs higher energy for cooking. Therefore,we tried to circumvent these challenges by fortifying 25% of black pericarp rice with white or red pericarp rice.
Conclusion
Fortification of C3G enriched black rice (25%) with red or white pericarp rice (75%) might bring a better nutritional quality in both cooking and baking condition. This may lead a way to the effective management of the non-communicable disease such as cancer for common rice consuming population.
... According to a previous study, soluble free protocatechuic acid and vanillic acid might act as precursors or accelerants in the anthocyanin biosynthesis pathway [26]. According to another study, cyanidin-3-glucoside is deglycosylated upon heating, with subsequent formation of protocatechuic acid upon degradation of deglycosylated cyani-din [27]. Furthermore, vanillic acid might be generated from peonidin-3-glucoside via the same mechanism [28]. ...
Comprehensive profiling of primary and secondary metabolites was performed to understand metabolic differences associated with color formation in pigmented rice (Oryza sativa L.). Overall, 110 metabolites from non-pigmented, black, and red rice cultivars were identified. Black and red rice contained high levels of flavonoids associated with plant color. Black rice also contained high levels of terpenoids (carotenoids, tocopherols, phytosterols, and monoterpenes). The non-pigmented rice contained relatively low levels of secondary metabolites. Multivariate and pathway analyses were performed to data-mine the metabolite profiles. Hierarchical clustering analysis of correlation coefficients revealed metabolite clusters based on nitrogen and carbon sources. These clusters suggested a negative correlation between nitrogen and carbon. Pathway analysis revealed that black rice was rich in carbon-based secondary metabolites, with relatively low levels of primary metabolites compared with other rice cultivars. These data highlight the complex interactions between nitrogen and carbon metabolism of primary and secondary metabolites in rice. For the first time, the relationships and metabolic differences in terpenoid content (monoterpenes, triterpenes, and tetraterpenes) of non-pigmented and pigmented rice cultivars were analyzed. These findings should greatly contribute to the understanding of pigmented rice metabolome and inform breeding programs for new rice cultivars.
... These variations can lead to higher or lower cleavage of phenolic bonds according to the type of heat applied and the food being analyzed [23]. Moreover, the heat treatments could inactivate polyphenol oxidases, preventing oxidation and polymerization of polyphenols [25]. ...
Green leafy vegetables (GLVs) are abundant in bioactive compounds and constitute a crucial part of a balanced diet. Sri Lankan green leafy vegetables which are edible and available for consumption have not been thoroughly investigated, whilst their consumption can deflate the risk of arising several degenerative diseases, such as cancer and cardiovascular diseases. The present study was aimed at evaluating the antioxidant capacities of the leafy vegetables, Gymnema lactiferum (Kurignan), Wattakaka volubilis (Aguna), and Argyreia populifolia (Girithilla), with different thermal treatments (70°C, 120°C, and 170°C) which are used in domestic cooking processes. Heat treatments significantly affect the antioxidant capacity and polyphenolic content of most vegetables analyzed, either increasing or decreasing the concentration of these compounds. In the presence of thermal treatments, Gymnema lactiferum (14.52-20.28 mg GAE/g DW) and Wattakaka volubilis (19.75-27.13 mg GAE/g DW) showed a significantly higher (p
The phenolic metabolites, antioxidant properties, and minerals of rice are highly affected by various hydrothermal treatments including cooking process. The purpose of this study was to use a metabolomic strategy to compare the effects of parboiling on metabolites, antioxidant capacity, and mineral content in raw rice, cooked rice, and rice gruel. The antioxidant properties of raw rice, cooked rice, and rice gruel, as well as specific phenolic metabolites and other phenolic compounds, were studied using multivariate analysis. MetaboAnalyst was utilized to determine the metabolic pathway. Cooked parboiled rice had higher Zn and Fe levels as compared to cooked non-parboiled rice. Parboiled rice lost 18.82% P, 9.27% K, 9.67% Mg, and 16.90% total phenol content, while non-parboiled rice lost 19.20% P, 17.92% K, and 25.19% phenol due to gruel removal during preparation. Notably, epicatechin was the most abundant metabolite in all samples, followed by 3,5-hydroxybenzoic acid, caffeic acid, and rutin hydrate, and positively correlated with Total phenolic content (TPC) and antioxidant activity. Parboiled rice with gruel can be a heather choice for consumers than other parboiled or non-parboiled rice.
Graphical Abstract
This paper evaluated the effects of different polishing times and regular cooking on the phytochemical properties and antioxidant activities of black rice Brillante, red rice Minaangan, and white rice NSIC Rc 160. Rice samples were polished for 0, 15, 30, and 45 s, and were cooked using their optimum cooking water ratio. The samples were then characterized for their phytochemical properties [total anthocyanin content (TAC), total phenolic content (TPC), and total flavonoid content (TFC)] and antioxidant activities [DPPH-radical scavenging activity (DPPH-RSA) and ferric reducing antioxidant power (FRAP)]. Pearson’s correlation analysis (PCA) was employed to determine the strength of the linear relationship between the polishing times and different parameters tested. Results showed that the pigmented rice samples had significantly higher phytochemical properties and antioxidant activities than the white rice sample. Polishing of rice samples considerably reduced their TAC (4.8% to 52.7%), TPC (13.0% to 65.2%), TFC (11.2% to 61.5%), DPPH-RSA (35.0% to 79.9%), and FRAP (11.8% to 68.5%). Cooking also decreased their TAC (24.1% to 92.6%), TPC (14.3% to 78.0%), TFC (14.4% to 74.2%), DPPH-RSA (38.9% to 84.6%), and FRAP (37.0% to 92.8%). Moreover, PCA showed that the polishing time had a strong to very strong negative correlation with phytochemical properties (-0.8809 to -0.9846) and antioxidant activities (-0.8106 to -0.9763). This study concluded that the polishing and cooking significantly affected the phytochemical content and antioxidant activities of white and pigmented rice cultivars. The information generated can be used as a basis for selecting suitable processes to better preserve the antioxidants of pigmented rice.
Rice is one of the most important staple plant foods that provide a major source of calories and nutrients for tackling the global hunger index especially in developing countries. In terms of nutritional profile, pigmented rice grains are favoured for their nutritional and health benefits. The pigmented rice varieties are rich sources of flavonoids, anthocyanin and proanthocyanidin that can be readily incorporated into diets to help address various lifestyle diseases. However, the cultivation of pigmented rice is limited due to low productivity and unfavourable cooking qualities. With the advances in genome sequencing, molecular breeding, gene expression analysis and multi-omics approaches, various attempts have been made to explore the genetic architecture of rice grain pigmentation. In this review, we have compiled the current state of knowledge of the genetic architecture and nutritional value of pigmentation in rice based upon the available experimental evidence. Future research areas that can help to deepen our understanding and help in harnessing the economic and health benefits of pigmented rice are also explored.
This research is aimed to study growth adaptation of Wojalaka black rice variety which is cultivated with The Banjarese system cultivation and its problem during planting period. A descriptive exploratory research was conducted in rainfed rice field in Binuang Village, Binuang District, Tapin Regency, South Kalimantan Province on November 2016 to May 2017. Land preparation was done with Tepulikampar technology and the seedbed was done in two stages, i.e. dry seedbed and continued with wet nursery. Observations were made on plant height, plant age, number of productive tillers, panicle length, number of seeds per panicle, weight per panicle, weight of 1000 seeds, total weight and problems during plant growth including pests, diseases and environmental conditions. The results showed that Wojalaka black rice variety were 125 cm high and the plant age was 176 days or longer than the normal age of 127 days. Number of productive tillers is relatively small as many as 12 tillers. The yield potential is almost equal to the potential yield in the area of origin. The Banjarese planting system is less suitable to be applied to the Wojalaka black rice variety because it causes the longer period of harvest and the decrease of the harvest. The attacks of rice ear bugs and birds and diseases caused by fungus Ustilaginoidea virens also cause the decline of crop yields. Keywords: Black rice, Growth, Wojalaka, Banjarese system cultivation
Interest in colored rice has been increasing due to its health benefits. This study examined the metabolite profiling of CONSTITUTIVELY PHOTOMORPHOGENIC 1 (COP1) mutated rice seed (yel-mutant). The wild-type (WT) and the yel-mutant having yellow (y)- and purple (p)-pericarp variants from Chucheong (cc) and Samkwang (sk) cultivars were investigated for differences in bioactive metabolite profiles and free radical scavenging activity. The total fatty acid content decreased by >50% in the yel-mutant against the WT, while no significant difference was observed between yellow- and purple-pericarp variants (p < 0.05). The yel-mutant of both cultivars showed significantly higher flavone contents than their WT (non-detected). Most of the metabolites examined were highly produced in the yel-cc-p and the yel-sk-y than in the other phenotypic variants studied. This study provides further useful information for colored rice breeding by revealing the detailed biofunctional metabolic profile under COP1 mutation in colored rice.
In recent years, consumers have been concentrating on the health benefits and nutrition from food to preserve a healthy lifestyle. They are looking for colorants derived from natural sources to enhance the nutritional and antioxidant value of foods. Coloured cereals (wheat, rice, barley, oat, maize, sorghum, and millets) contain many phytochemicals, including anthocyanins and carotenoids associated with numerous health benefits. This book presents a comprehensive overview of the bioactive potential, food applications, and health benefits of coloured cereal grains. Novel approaches to the integration of coloured grain into food in the food processing industries are included, reviewing high-value pigments in the bran layer which can easily be extracted and utilized as functional foods and natural colorants.
Aimed at researchers carrying out innovative studies, food regulatory and safety authorities and food processing industries who are trying to minimize synthetic food colorants and dyes, this book provides a novel approach to the use of substitute synthetic dyes which can improve the nutritional value, appearance, texture, flavour, and storage properties of food products.
Black rice is widely popular variant of rice (Oryza sativa L.) popularly consumed in India and other South Asian countries and is a part of the traditional practices of certain parts of India and amongst certain communities. The abundance of a variety of minerals such as Zinc, Potassium, iron and the phenolic compounds have proved black rice as suitable for usage in anti-diabetic, anti-inflammatory, anti-carcinogenic treatments, and in aiding a healthier health and mind, via-a-vis the traditionally popular practices of its use. The present study is a descriptive delineation of the nutritional benefits of black rice and its avenues as a snack and as a natural food colourant. The study attempts to explore black rice as a promising element as possible additives in food industry as colorants and value added food products. The purpose of the paper is aid researchers in black rice studies to understand the benefits and potential in the food industry.
Protocatechuic acid (PCA) and its precursor protocatechuic aldehyde (PCAL) are widely distributed polyphenols found in edible plants, fruits, and vegetables. PCA is the major human metabolite of cyanidin-glucosides derived from anthocyanins (ACN). Evidence suggests, that both PCA and PCAL influence the profile of the gut microbiota which contributes to the improvement of health benefits for humans. As agents used by plants in the self-defense, they have antibacterial and antiviral activity. Consumption of these substances is associated with lowered risk of some chronic conditions such as cardiovascular diseases. In aging-related states such as neurodegeneration, a reduction in amyloid deposition associated with Alzheimer’s disease was observed. Both PCA and PCAL have been shown to have antioxidant activity in vitro and in vivo, and beneficial effects in chronic inflammation. Both have been shown to be effective in cancer chemoprevention. The preventive effect of PCA in experimental models of the metabolic syndrome is of great importance, thanks to the antidiabetic effect and reducing obesity. PCA and PCAL show antiatherogenic activity; moreover, PCA acts as an anti-aggregating agent, reducing the risk of thrombosis. In preclinical studies, a beneficial effect of PCA in inhibiting osteoporosis has been found. It should be taken into account, that phenolic acids as dietary components, inter alia, show anticancer activity by reversing epigenetics-related changes, that lead to the activation of oncogenes and inactivation of suppressive genes.
Cancer prevention using dietary phytochemicals holds great potential, particularly in the alternative treatment of liver cancer. Our previous study found that the methanol extract of cooked purple rice performed various biological functions including antioxidant, anti-inflammatory, and antimutagenic activities in in vitro assays. This study aimed to evaluate the chemopreventive effects of cooked glutinous purple rice extract (CRE) obtained from routine rice cooking method on diethylnitrosamine (DEN)-induced hepatic preneoplastic lesions in rats, along with its inhibitory mechanisms. CRE containing γ-oryzanols and high amounts of polyphenolic compounds, particularly cyanidin-3-glucoside, was fed to rats over a period 15 weeks. Additionally, injections of triple DEN at a concentration of 100 mg/kg BW were administered to rats once a week during the second, third, and fourth weeks of the experiment. The results revealed that CRE did not induce the formation of glutathione S-transferase placental form (GST-P) positive foci as a precancerous lesion during rat hepatocarcinogenesis, indicating non-carcinogenicity. Furthermore, CRE significantly reduced the number and size of GST-P positive foci in DEN-initiated rats. It also modulated microenvironment homeostasis by reducing the number of PCNA positive hepatocytes and by enhancing the number of apoptotic positive hepatocytes in the livers of DEN-initiated rats. Using RT-PCR analysis, CRE decreased the mRNA expression of some proinflammatory mediators, including interleukin-6, interleukin-1 beta, inducible nitric oxide synthase and cyclooxygenase 2, by attenuating the expression of cyclin E, the proliferation marker, while also inducing the expression of the apoptotic gene, Bcl2 associated X. The inhibitory mechanism at the early stages of hepatocarcinogenesis of CRE may be involved with the attenuation of cell proliferation, the enhancement of apoptosis, and the modulation of the proinflammatory system. Anthocyanins, flavonoids, and γ-oryzanol represent a group of promising chemopreventive agents in cooked glutinous purple rice extract. The outcomes of this study can provide an improved understanding of the potential role of the phytochemicals contained in cooked purple glutinous rice with regard to cancer alleviation.
Black rice is rich in anthocyanins, and the antioxidant effect of anthocyanins is recognized by consumers. The aim of this study was to identify the molecular mechanisms underlying the antioxidant activity of black rice anthocyanin extract (BRAE) in PC12 cells and C. elegans. Results showed that BRAE increased antioxidant enzyme activities and decreased the accumulation of reactive oxygen species (ROS) and malondialdehyde in PC12 cells induced by H2O2. Meanwhile, BRAE extended the lifespan, enhanced resistance to stress, increased antioxidant enzyme activities, and reduced lipofuscin, ROS, and MDA accumulation in wild-type C. elegans. The polyQ40 aggregation in AM141, paralysis in CL4176, and chemotaxis deficit in CL2355 were alleviated by BRAE administration. BRAE downregulated the mRNA expression of age-1 and daf-2, while upregulated the daf-16 mRNA level and SOD-3, CTL-1, and GST-4 protein expression. Mutational lifespan tests and molecular docking showed that insulin pathway might be involved in the mechanism of lifespan extension.
Developing rice varieties with enhanced levels of functional bioactives is an important intervention for achieving food and nutritional security in Asia where rice is the staple food and Type II diabetes incidences are higher. The present study was aimed at dissecting out the molecular events underlying the accumulation of bio active compounds in pigmented traditional rice Kavuni. Comparative transcriptome profiling in the developing grains of Kavuni and a white rice variety ASD 16 generated 37.7 and 29.8 million reads respectively. Statistical analysis identified a total of 9177 exhibiting significant differential expression (DEGs) between the grains of Kavuni and ASD 16. Pathway mapping of DEGs revealed the preferential up-regulation of genes involved in the biosynthesis of amylose and dietary fibres in Kavuni accounting for its low glycemic index (GI). Transcripts involved in the biosynthesis of carotenoids, flavonoids, anthocyanins, phenolic acids and phenylpropanoids were also found to be up-regulated in the grains of Kavuni. This study identified up-regulation of key transcripts involved in the accumulation of phenolic acids having potential for inhibiting major hydrolytic enzymes α-amylase and α-glucosidase and thus accounting for the slow digestibility leading to low GI. Overall, this study has identified molecular targets for the genetic manipulation of anti-diabetic and anti-oxidant traits in rice.
Pigmented rice has attracted attention due to its high anthocyanin content. However, the relationship between the anthocyanin content, color value, and absorption efficiency of anthocyanins has not been well studied in rice. In this study, the color parameter a* and the contents of functional substances (total phenols, total flavonoids, carotenoids, and anthocyanins) in five different rice varieties (BR207, BR307, RR208, RR308, and WR3010) were investigated. The absorption efficiencies of total anthocyanins and cyanidin-3-o-glucoside (C3G) in BR207 and BR307 rice were assessed using an in vitro model, and the correlation between anthocyanin absorption and inherent starch concentration was analyzed in digestion products. The results indicated that the anthocyanin concentration in BR207 and BR307 were higher than that in other varieties. The anthocyanin content showed a positive correlation with the color parameter a*, revealing a close relationship between the anthocyanin content and the color values of black rice varieties. In the simulated digestion process, the bioaccessibility of C3G in BR307 and BR207 was approximately 68.67 ± 16.32% and 24.08 ± 5.59%, respectively. Furthermore, the linear analysis showed that the anthocyanin content was significantly negatively correlated with the starch concentration, indicating a mutual relationship between anthocyanin absorption and the starch concentration. This study provided basic data for understanding the absorption efficiency of anthocyanins in pigmented rice and discussed the factors that might affect its absorption efficiency in humans.
Anthocyanins are water-soluble, colored compounds of the flavonoid class, abundantly found in the fruits, leaves, roots, and other parts of the plants. The fruit berries are prime sources and exhibit different colors. The anthocyanins' utility as a traditional medicament for liver protection and cure and importance as strongest plants-based anti-oxidants have conferred these plants products different biological activities. These activities include anti-inflammation, liver protective, analgesic, and anti-cancers, which have provided the anthocyanins an immense commercial value and have impelled their chemistry, biological activity, isolation, and quality investigations as prime focus.
Methods in extraction and production of anthocyanin-based products have assumed vital economic importance. Different extraction techniques in aquatic solvents mixtures, eutectic solvents, and other
chemically reactive extractions including low acid concentrations-based extractions have been developed. The prophylactic and curative therapy roles of the anthocyanins, together with no reported
toxicity have offered much-needed impetus and economic benefits to these classes of compounds which are commercially available. Information retrieval from various search engines, including the
PubMed®, ScienceDirect®, Scopus®, and Google Scholar®, were used in the review preparation. This imparted an outlook on the anthocyanins occurrence, roles in plants, isolation-extraction, structures, biosynthetic as well as semi- and total-synthetic pathways, product quality and yields enhancements, including uses as part of traditional medicines, and uses in liver disorders, prophylactic and therapeutic applications in liver protection and longevity, liver cancer and hepatocellular carcinoma. The review also highlights the integrated approach to yields maximizations to meet the regular demands of the anthocyanins products, also as part of the extract-rich preparations together with a listing of marketed products available for human consumption as nutraceuticals/food supplements.
Background and objectives
The traditional heat processing methods, steaming and cooking treatment can affect the nutrients in rice, such as phenolics, flavonoid and dietary fiber, etc. However, there is no systematic assessment that by which heat treatment method and conditions more nutrients in rice can be retained, especially in brown rice, two-times milling rice, four-times milling rice, polished rice and color selection rice (from different milling processes with practical processing at rice milling factory). The aim of this study was to investigate the effect of steaming and cooking treatment on the changes of nutrients in rice with different milling processes, including dietary fiber and phenolic acids, flavonoid, anthocyanin, individual phenolic compounds, antioxidant activities (DPPH, ABTS and T-AOC) in the free and bound extracts.
Findings
Compared with unsteamed and uncooked rice, the total phenolic content (TPC), the total flavonoid content (TFC) and individual phenolic compounds in the free and bound fractions, total anthocyanin content (TAC) and antioxidant activity in the free fractions in brown rice, two-times milling rice, four-times milling rice, polished rice and color selection rice were significantly reduced by steaming and cooking treatment (p < 0.05). The TAC and antioxidant activity in the bound fractions, soluble dietary fiber (SDF), insoluble dietary fiber (IDF) and total dietary fiber (TDF) in the five rice samples were increased after steaming and cooking. However, it was very interesting that steaming treatment resulted in a less reduction in phenolics and antioxidant activities than cooking.
Conclusions
From the view of retaining more nutrients, steaming treatment is more suitable for the white rice of the milling process with high milling degree, while cooking treatment is more suitable for the brown rice or rice of milling process with low milling degree. Generally, steaming treatment retains more phenolics, dietary fiber and antioxidant activities than cooking rice with different milling processes.
Significance and novelty
This study may provide useful reference and offer a simple and practical method to retain more nutrients for preparation and consumption of rice. These results suggest that steaming treatment is an efficient method of daily processing to reduce the loss of nutrients in rice.
Anthocyanins are water-soluble pigments widely distributed in fruits and vegetables. The compound has important functions in the propagation, protection, and physiology of plants. Moreover, the antioxidative and anti-inflammatory features of anthocyanins also make them promising ingredients in promoting human health. Emerging evidence shows that the biosynthesis and structure of anthocyanins are influenced by the genetic background and growth environment of the source, which varies substantially with plants. Thus, we will summarize the published results regarding the anthocyanin profiles in fruits, vegetables, grains, and herbs in this chapter, which is not only important to its application in food industry but also important to the development of dietotherapies containing anthocyanins.
This study arose from the need to meet the request of consumers for healthy, ready-to-eat foods. The behavior of pigmented rice was investigated during extrusion in terms of nutritional (i.e., phenolic acids, anthocyanins and antioxidant capacity (AC)) and physical (i.e., starch pasting properties, texture, porosity and biometric indices) properties. Snacks were produced from brown, red, and black rice, by means of a co-rotating twin-screw extruder, and their features were compared with those of snacks from white rice. Although the soluble and cell-wall bound phenolic acid contents of pigmented and brown rice did not differ, the red and black rice both resulted in a higher AC after extrusion. Black rice showed the highest anthocyanin and AC contents, even after extrusion. Furthermore, the high phenolic compound content of black rice affected the starch pasting properties, and led to a lower viscosity and higher snack porosity than those of brown rice. Nevertheless, considering both the biometric and textural properties, the best results were obtained from red rice. Optimizing the extrusion conditions will help reduce the loss of anthocyanins in snacks made of pigmented rice, increase the nutritional value and improve the physical properties of the product.
Anthocyanins are a major subclass of flavonoids that have diverse biological functions and benefit human health. In rice (Oryza sativa), the various colors shown by organs are due mainly to the accumulation of anthocyanins and are traits associated with domestication. Elucidating the genetic basis of anthocyanin biosynthesis in rice would support the engineering of anthocyanins as well as shedding light on the evolutionary history of O. sativa. We summarize recent progress in rice anthocyanin biosynthesis research, including gene cloning, biosynthetic pathway discovery, and study of the domestication process. We discuss the application of anthocyanin biosynthesis genes in rice breeding. Our object is to broaden knowledge of the genetic basis of anthocyanin biosynthesis in rice and support the breeding of novel rice cultivars.
Pigments are present in all living matter and provide attractive colors and play basic roles in the development of organisms. Human beings, like most animals, come in contact with their surroundings through color, and things can or cannot be acceptable based on their color characteristics. This review presents the basic information about pigments focusing attention on the natural ones; it emphasizes the principal plant pigments: carotenoids, anthocyanins, and betalains. Special considerations are given to their salient characteristics; to their biosynthesis, taking into account the biochemical and molecular biology information generated in their elucidation; and to the processing and stability properties of these compounds as food colorants.
Black rice and its pigment fraction may have antiatherogenic activity, but the exact component contributing to the beneficial effect remains unclear. The aim of the present study was to investigate the influence of the anthocyanin-rich extract from black rice on the vulnerability of advanced plaques in apolipoprotein (apo) E-deficient mice. Using LC-MS, the anthocyanin-rich extract from black rice was identified as containing cyanidin-3-glucoside and peonidin-3-glucoside. ApoE-deficient mice (n = 30; 30 wk old) were randomly divided into 3 groups: a control group (fed the AIN-93G diet), the simvastin group [simva; fed the AIN-93G diet containing simvastatin, 50 mg/(kg.d)], or the anthocyanin-rich extract group [antho; fed the AIN-93G diet supplemented with anthocyanin-rich extract from black rice, 300 mg/(kg.d)]. After 20 wk of intervention, the plaque area that developed in the brachiocephalic artery of mice in the antho group was smaller than that of the control mice. Both the antho and simva groups had lower frequencies of the large necrotic core and thin fibrous cap in plaques than the control group. Collagen I was increased and matrix metalloproteinase-1 contents were reduced in the brachiocephalic lesion of both the antho and simva groups compared with the control group. Furthermore, mRNA levels of tissue factor and inducible nitric oxide synthase in aortae were decreased in the antho and simva groups. Supplementation of anthocyanin-rich extract improved the lipid profile by decreasing serum triglyceride, total cholesterol, and non-HDL cholesterol. These results suggest that chronic diet intake of anthocyanin-rich extract from black rice may enhance plaque stabilization in old apoE-deficient mice. The underlying mechanism is related mainly to inhibiting proinflammatory factors and improving the serum lipid profile.
Anthocyanin pigments in ten pigmented rice cultivars were isolated with cellulose thin-layer chromatography and preparative high performance liquid chromatography (HPLC), and further identified with conventional chromatographic techniques. Individual anthocyanins were then quantified by HPLC using a reversed ODS-5 column and detected at 280 nm. Ten rice varieties contained two major anthocyanins, cyanidin 3-glucoside and peonidin 3-glucoside. Total anthocyanin contents varied greatly in the range of 0-493 mg/100 g grain among varieties. Cyanidin 3-glucoside, an agent having important oxygen radical absorbing capacity (ORAC), was most abundant in Suwon #415 variety (470 mg/100 g grain), while Jawangdo (10 mg/100 g grain) and Ilpumbyeo (not detected) had the smallest amount of anthocyanin among the samples examined. As for the distribution ratio of individual anthocyanin, Suwon #415 was characterized by a relatively high percentage of cyanidin 3-glucoside (95.3%); whereas, Suwon #425 and Heugjinmi were characterized by a relatively larger amount of peonidin 3-glucoside.
Interest in food colorants as shown by the number of patents has doubled in recent years with natural pigments outnumbering synthetics by five to one. The natural colorant area can be subdivided into anthocyanins, betalains, chlorophylls, carotenoids, flavonoids, polyphenols, Monascus, hemes, quinones, biliproteins, safflower, turmeric, and miscellaneous. All involve different groups of chemical compounds which may be used directly as colorants, or may be chemically modified to produce different hues or increased stability. All usually involve a method of collection, extraction, purification, possibly stabilization, and formulation. A variety of hues can be obtained ranging from green through yellow, orange, red, blue, and violet, depending on the source of colorant. Similarly, water or oil‐soluble formulations can be prepared depending on the type of colorant.
The composition of fatty acids, minerals, total dietary fiber and vitamin , in pigmented rice varieties were determined. Proximate composition and color were also compared among pigmented rice varieties. Crude protein contents of black rice were higher than those of red and brown rice, especially, Suwon 415 had the highest protein content. There were no significant differences in lipid and crude ash contents between pigmented rice and brown rice. Black rice showed lower Hunter value L, a and b value compared with red and brown rice. Most mineral contents of pigmented rice except Fe, Zn and Mn were higher than those of brown rice. Pigmented rice showed the higher contents in total dietary fiber, vitamin compared to brown rice. The major fatty acids of pigmented rice were palmitic acid, oleic acid and linoleic acid. The contents of oleic acid was similar to that of linoleic acid in brown rice. Oleic acid contents was lower than linoleic acid in black rice, but higher in red rice.
The thermal degradation pathways of acylated and nonacylated anthocyanins from 3 commercial sources have been investigated. Strawberry, elderberry, and black carrot concentrates were purified on XAD-16-HP and Sephadex-LH-20 columns to remove sugars, amino acids, salts, and phenolic compounds, respectively. The so obtained anthocyanin isolates were heated at 95 °C at pH 1, the optimum stability condition for the flavylium cation. During 7 h of thermal exposure, the samples were monitored by HPLC-DAD-MS3 at 280, 320, and 520 nm, respectively, together with spectrophotometric color and anthocyanin assessment. Total anthocyanin content lightness, and chroma, but not hue angle, were appropriate parameters to monitor anthocyanin loss on a statistically significant level. Anthocyanin glycosides were generally cleaved by successive loss of sugar moieties and pentoses were more readily split off than hexoses. Anthocyanin aglycones were further degraded by scission into phloroglucinaldehyde (cyanidin, pelargonidin), 4-hydroxybenzoic acid (pelargonidin), and protocatechuic acid (cyanidin), the residues of the A- and B-rings, respectively. Most interestingly, acylated cyanidin-triglycosides from black carrot were degraded into their corresponding diglycoside derivatives, which are not genuine carrot pigments. Moreover, hydroxycinnamic acid glycosides were generated. It is therefore assumed that the thermal burden during processing of anthocyanic food can be deduced by monitoring the colored and colorless compound profiles.
Cereal Chem. 76(3):350–354 A simple, rapid method for determining total anthocyanins was devel-oped for use in developing wheat cultivars with dark-blue grains. The method was evaluated as a screening test and for quantification of total anthocya-nins in blue and purple wheats and related cereals. Wheat anthocyanins were significantly more extractable in ethanol or methanol than in water at different pH levels. A sample-to-solvent ratio of 1:8 at pH 1 and 25°C was used. Anthocyanin extracts of pigmented wheat and barley grains exhibited absorbance spectra similar to cyanidin 3-glucoside. The absor-bance of anthocyanin extracts of 160 blue wheat experimental lines were significantly correlated with whole-grain Hunterlab color values. Total antho-cyanins averaged 157 mg/kg in blue wheat whole meal and 104 mg/kg in purple wheat whole meal, whereas blue wheat bran contained 458 mg/kg as compared with 251 mg/kg in purple wheat bran.
Complete diallel crosses with Oryza sativa L., six varieties of black rice and one variety of aromatic white rice were conducted to study the seed, maternal and cytoplasmic
genetic effects on grain characteristics such as 100-grain weight, length, width and shape and their genetic correlations
with Fe, Zn, Mn and P mineral contents in kernels by using the genetic model on quantitative traits of seed in parents and
their F1s and F2s. The seed genetic effects were found more important than the maternal genetic effects for grain characteristics, and seed
additive effects constituted a major part of their genetic effects. The heritabilities of seed effects were high for 100-grain
weight, width and shape and moderate for grain length. Single seed selection based on the 100-grain weight, width and shape
was advocated in early generations, whereas single plant and seed selection based on grain length were advocated in late generations.
Significant genetic correlations including seed additive, dominance, cytoplasmic, maternal additive and dominance between
100-grain weight, length, width and shape and Fe, Zn, Mn and P mineral contents were observed. Indirect selection of grain
characteristics may be one of the breeding methods to select for higher contents of Fe, Zn, Mn and P in black pericarp indica rice.
Violet cauliflower and red cabbage were analysed for their anthocyanin profiles before and after thermal treatments. Anthocyanins are well-noted as healthy compounds due to their antioxidant properties. Samples were analysed for total anthocyanin content by using a spectrophotometric differential pH method. An MS-based method, combining high-performance liquid chromatography (HPLC) with quadrupole tandem mass spectrometry (HPLC–MS/MS) was developed, aimed to separate, identify and quantify the main anthocyanin forms. The procedure involves a rapid and efficient pre-treatment of the samples by solid-phase extraction, followed by selective determination of all compounds in a single run analysis using HPLC–MS/MS. Structural information for the identification of compounds was obtained from their fragmentation patterns (MS/MS spectra). The compounds were separated by HPLC and detected in the multiple reaction monitoring mode (MRM), which provides a high level of selectivity for targeting the analytes in vegetables. Cauliflower and red cabbage showed differences in their anthocyanin profiles: cyanidin-3,5-diglucoside was absent in cauliflower, while it was well represented in red cabbage, together with the characteristic anthocyanin of Brassica genus, cyanidin-3-sophoroside-5-glucoside. The p-coumaryl and feruloyl esterified forms of cyanidin-3-sophoroside-5-glucoside were predominant in cauliflower, while the sinapyl one was mostly present in red cabbage. Besides, the stability of cauliflower’s anthocyanin profile was evaluated in relation to thermal pre-treatments. All thermal treatments, except microwave heating, drastically reduced total cauliflower anthocyanin content. The amount of individual anthocyanins was expressed as the percentage with respect to total anthocyanin amount, spectrophotometrically measured. Significant individual changes were observed after different thermal treatment with an isomer formation.
Antioxidant activity of purple wheat bran, heat-treated purple wheat bran, and purple wheat bran muffins was evaluated to determine the impact of thermal processing on potential health benefits. The purple wheat bran and muffin samples were analyzed for total phenolic content, anthocyanin content and free radical scavenging activity using peroxyl (oxygen radical absorbance capacity assay) and 2,2-diphenyl-1-picrylhydrazyl (DPPH assay) radicals. Total phenolic content and oxygen radical absorbance capacity (ORAC) values of sample extracts were significantly affected by various extracting solvents. The conditions selected for heat treatment did not markedly change antioxidant activity of purple wheat bran. However, there was a significant reduction in total phenolic contents, ORAC values and total anthocyanins during processing of purple wheat bran- or heat-treated purple wheat bran-enriched muffins. On the contrary, muffin extracts still remained excellent in DPPH radical scavenging activity.
Two anthocyanins (cyanidin-3-O-β-glucoside and peonidin-3-O-β-glucoside) and other phenolic (ferulic acid) were, respectively isolated from black and pigmented brown rices (Oryza sativa L. japonica) and their complete structures were determined by spectroscopic analyses (H NMR, C NMR and MALDI MASS). The HPLC profile of anthocyanins extracted from black rice showed cyanidin-3-O-β-glucoside as the first peak (85%) and peonidin 3-O-β-d-glucoside as the second (15%), while that of pigmented brown rice showed ferulic acid as the first peak (85.7%) and tocols as the second (14.3%). Several tocols were isolated and identified from the unsaponifiable fractions of both rices having some difference on their structures and amounts. The aldose reductase inhibitory activity of isolated compounds was in the following decreasing order: cyanidin-3-glucoside > quercetin > ferulic acid > peonidin-3-glucoside > tocopherol.All isolated compounds showed significant inhibitory activity against aldose reductase suggesting that both pigmented rices might contribute significantly in combating diabetic complications as health-promoting food ingredients in food processing.
Anthocyanins and betalains play important roles both in plant physiology, visual attraction for pollinators and seed dispersers, but also in food mainly defining its aesthetic value. Since anthocyanin and betalain structures allow to predict only part of their appearance, additional chemical and anatomical functions are required to modulate the appearance of plants and coloured food. Physiological effects that the same pigments exert in plants are supposedly similar to those which they show in humans following ingestion of coloured food. Therefore, anthocyanins and betalains both in fresh and also processed fruit and vegetables serve two functions: They improve the overall appearance, but also contribute to consumers' health and well-being.
This study on anthocyanin stability and colour variation (λmax, ε) in the pH range 1–12 during a period of 60 days storage at 10 and 23°C, was conducted on the 3-glucosides of the six common anthocyanidins. It was mostly in the alkaline region that differences in colour and stability became significant. Although it has been generally accepted that anthocyanins are stable only at low pH values, this study revealed that, for some of the anthocyanin 3-glucosides (e.g. malvidin 3-glucoside), the bluish colours were rather intense and stability relatively high in the alkaline region. Thus, they can be regarded as potential colorants for some slightly alkaline food products.
Liquid chromatography (LC) was used for the fractionation of particular anthocyanins in glycoside form from methanol extracts of red grape skins and solid phase extracts of red wine. By the combination of nuclear magnetic resonance spectroscopy and LC-mass spectroscopy the identification of 13 anthocyanins in a particular LC fraction and hence the in particular peaks in chromatograms were obtained. Peaks areas in the chromatograms obtained under the semi-quantitaive conditions of the solid phase extracts of red wines Pinot Noir, Cabernet Sauvignon and Merlot from the Coastal wine-growing region in Slovenia, produced in 1999, were used as input data in chemometric analysis. The chemometric methods used were hierarchical clustering analysis and regularised discriminant analysis. The results of both methods give 100% correct classification of wines regarding the vine variety.
The effects of boiling and steaming processes on the phenolic components and antioxidant activities of whole yellow (with yellow seed coat and yellow cotyledon) and black (with black seed coat and green cotyledon) soybeans were investigated. As compared to the raw soybeans, all processing methods caused significant (p < 0.05) decreases in total phenolic content (TPC), total flavonoid content (TFC), condensed tannin content (CTC), monomeric anthocyanin content (MAC), DPPH free radical scavenging activity (DPPH), ferric reducing antioxidant power (FRAP), and oxygen radical absorbing capacity (ORAC) in black soybeans. Pressure steaming caused significant (p < 0.05) increases in TPC, CTC, DPPH, FRAP, and ORAC in yellow soybeans. The steaming resulted in a greater retention of TPC, DPPH, FRAP, and ORAC values in both yellow and black soybeans as compared to the boiling treatments. To further investigate the effect of processing on phenolic compounds and elucidate the contribution of these compounds to changes of antioxidant activities, phenolic acids, isoflavones, and anthocyanins were quantitatively determined by HPLC. The pressure steaming treatments caused significant (p < 0.05) increases in gallic acid and 2,3,4-trihydroxybenzoic acid, whereas all treatments caused significant (p < 0.05) decreases in two predominant phenolic acids (chlorogenic acid and trans-cinnamic acid), and total phenolic acids for both yellow and black soybeans. All thermal processing caused significant (p < 0.05) increases in aglucones and beta-glucosides of isoflavones, but caused significant (p < 0.05) decreases in malonylglucosides of isoflavones for both yellow and black soybeans. All thermal processing caused significant (p < 0.05) decreases of cyanidin-3-glucoside and peonidin-3-glucoside in black soybeans. Significant correlations existed between selected phenolic compositions, isoflavone and anthocyanin contents, and antioxidant properties of cooked soybeans.
Olive oil contains several phenolic compounds with antioxidant activity, whose levels depend strongly on the kind of cultivar grown, fruit ripening effects and the oil extraction process. Therefore, the beneficial effects exerted by olive oil consumption on the resistance of low density lipoproteins (LDLs) to oxidation depend not only on an increased intake of mono-unsaturated fatty acids (e.g. oleate) which are less prone to oxidation, but also phenolic antioxidants. The aim of this study was to analyze in vitro effects exerted on the oxidative modification of Cu-stimulated human LDL by two olive oil biophenols, i.e. 3,4-dihydroxyphenylethanol-elenolic acid (3,4-DHPEA-EA) and protocatecuic acid. These compounds have not been investigated in as much detail as the better-known olive oil biophenols - such as tyrosol (p-HPEA), o-coumaric acid, vanillic acid, caffeic acid, oleuropein and 3,4-dihydroxyphenylethanol (3,4-DHPEA). Modification of LDL was tested by measuring the formation of intermediate and end products of lipid peroxidation such as conjugated dienes, lipid hydroperoxides, cholesterol and cholesteryl ester oxides, as well as studying the decrease in oxidizable substrates like polyunsaturated fatty acids. In addition, the increase in LDL negative charges was evaluated. The results demonstrate the two-tested olive oil biophenols show high antioxidant activities. In particular, protocatecuic acid and 3,4-DHPEA-EA show an antioxidant activity comparable with that of caffeic acid, oleuropein and 3,4-DHPEA. They are not only able to retard lipid peroxidation, but also to reduce the extent of its activity.
The modifying effects of topical application of the phenolic antioxidant protocatechuic acid (PA) on 12-O-tetradecanoylphorbol-13-acetate (TPA)-induced mouse skin tumor promotion were investigated. Dimethylbenz[a]anthracene-initiated female ICR mice were treated with TPA (1.6 nmol) twice weekly for 20 weeks to promote papilloma formation. Pre-treatment with 16nmol PA 30 min prior to each TPA treatment significantly inhibited the number of papillomas per mouse by 52% (P < 0.05). On the other hand, PA pre-treatment at a high dose (1600 nmol) significantly enhanced tumor numbers by 38% (P < 0.05). Interestingly, in the group treated with a quite high dose (20000 nmol) of PA 5 min prior to each TPA application, the average number of tumors per mouse was reduced by 38%, whereas the same PA dose 3 h before TPA treatment significantly enhanced tumor numbers by 84% (P < 0.01). These results suggested that topically applied PA was converted to compound(s) lacking antioxidative properties and/or rather possessing the potential to enhance tumor development. A similar tendency was also observed in the short-term experiment of TPA-induced inflammation and oxidative stress; i.e. two groups pre-treated with PA at 20000 nmol, 30min and 3h before TPA treatment, did not show suppression or even significantly enhanced TPA-induced leukocyte infiltration, H(2)O(2) generation, thiobarbituric acid-reacting substances level and proliferating cell nuclear antigen index, while PA treatment together with TPA significantly suppressed these parameters. Treatment with a high dose (20000 nmol) of PA alone for 3h enhanced oxidative stress by reducing glutathione levels in mouse skin, which was counteracted by the tyrosinase inhibitor arbutin. Oxidative stress responses such as leukocyte infiltration and H(2)O(2) generation were also counteracted by arbutin. These results suggested that tyrosinase-dependent oxidative metabolism of PA was at least partially involved in the enhanced effects of PA on TPA-induced inflammatory responses and thus tumor promotion.
The distribution of chemical constituents is known not to be even within a rice kernel. To improve the eating quality of rice or to give it some special traits by adjusting the milling intensity, we investigated the distribution of amylose, nitrogen (N), and specific minerals (P, K, Mg, Ca, and Mn) in rice kernels of 11 cultivars with various characteristics cultivated under similar conditions. The distributions of these constituents were determined using flour samples prepared consecutively by abrasive milling from the outer to the inner portions of hulled rice. In all the cultivars tested, N and the minerals were found to be more abundant in the outer than in the inner portion, but amylose was rich in the inner portion. P, Mg, K, and Mn were extremely rich in the outer portion, while N and Ca were only relatively rich there. Koshihikari, which is the most popular cultivar in Japan because of its excellent eating quality, showed the highest Mg/K ratio in the outermost portion of polished rice. The color of flour samples became pure white going from outside portions toward the center of the kernel, even if the sample was from red rice or purple-black rice because only the surface of hulled rice contains pigments. These findings suggest that the outer portion contains various compounds other than starch and the inner portion contains relatively pure starch. Rice palatability and other characteristics can be improved through controlling the degree of milling using the biased distribution of chemical constituents within a rice kernel.
Data on the biologic activity of protocatechuic acid are contradictory; some studies have shown that it acts as an antioxidant and suppresses chemical-induced carcinogenesis and others that it induces oxidative stress and promotes tumour formation. The anticarcinogenicity of protocatechuic acid was postulated to be related, in part, to its specific suppression of neoplastic hyperproliferation. To determine whether protocatechuic acid was preferentially antiproliferative to malignant cells, non-malignant and carcinoma cells were exposed for 24 hr to protocatechuic acid (2.5 to 25 mM) and viability was assessed with the neutral red assay. The cell lines were derived from tissues of the human oral cavity, the initial site of exposure upon ingestion of dietary protocatechuic acid, and included normal GN61 gingival fibroblasts, immortalized, non-tumorigenic S-G gingival epithelial cells, and malignant HSG1 cells derived from the salivary gland, HSC-2 cells from the floor of the oral cavity, and CAL27 cells from the tongue. Selective toxicity of protocatechuic acid to malignant cells was not observed. Furthermore, using a total cellular protein determination to quantitate cell growth, no differences in comparative sensitivities of S-G epithelial cells and HSG1 carcinoma cells were noted in a 3 day continuous exposure to 2.5 to 12.5 mM protocatechuic acid and in recovery from a 24 hr exposure to 3 to 15 mM protocatechuic acid. The S-G and HSG1 cells were then used to study the effects of elevated concentrations of protocatechuic acid on oxidative stress. For both cell types, protocatechuic acid induced oxidative stress, presumably through its bioactivation by a tyrosinase pathway. A brief exposure to 25 mM protocatechuic acid lowered the levels of intracellular glutathione and potentiated Fe2+-induced lipid peroxidation of the cells. As determined with the neutral red assay, S-G and HSG1 cells exposed briefly to a non-toxic level (0.5 mM) of the glutathione depleter, 1,3-bis(2-chloroethyl)-N-nitrosourea, were hypersensitive to a subsequent challenge with 10 mM protocatechuic acid and preexposure of the S-G and HSG1 cells to a nontoxic level of protocatechuic acid (2.5 mM) enhanced their sensitivity to a subsequent exposure to tert-butyl hydroperoxide. These findings were consistent with protocatechuic acid, at high levels (> or = 10 mM), acting as an inducer of oxidative stress.
Antioxidant activity was studied for anthocyanins extracted from purple black rice (PBR) by a 3% aqueous trifluoroacetic acid solution (TFA), as well as for anthocyanins extracted from blueberry (Bluetta, high bush type). Capillary zone electrophoresis revealed that the PBR extract contained almost exclusively a single anthocyanin, which was identified as cyanidin 3-O-beta-D-glucoside (Cy 3-Glc) after purification by polyvinylpyrrolidone column chromatography. In contrast, 11 anthocyanins were identified in the blueberry extract. PBR extract showed slightly weaker superoxide scavenging and crocin bleaching activities than blueberry extract did. Both PBR and blueberry extracts, however, showed 10 to 25 times stronger activity than the same concentration of Trolox used as a reference antioxidant. It was further noted that the purified Cy 3-Glc from PBR extract retained approximately 74% of the antioxidant activity (both crocin bleaching and superoxide scavenging) observed in the original TFA extract. The hydroxyl radical scavenging activity of both extracts was several times weaker than that of the same concentration of Trolox, although the PBR extract showed approximately two times stronger activity than blueberry extract did. The hydroxyl radical scavenging activity of the purified Cy 3-Glc from PBR, however, decreased to approximately 20% of that of the original PBR extract. These results indicate that the anthocyanin Cy 3-Glc contributes to the antioxidant activity of PBR through its strong superoxide radical but not hydroxyl radical scavenging activity.
Wheat grain is recognized as a good source of potentially health-enhancing components such as dietary fiber, phenolics, tocopherols, and carotenoids. Anthocyanins, another group of bioactive compounds, are found in blue and purple wheat grains. In the present study, a blue aleurone spring wheat line "Purendo 38" with relatively high content of total anthocyanins was used to investigate the composition and stability of anthocyanins over three crop years. Commercial cultivars of purple (Konini) and red (Katepwa) wheats were included in the study. Separation of anthocyanins by high-performance liquid chromatography (HPLC) showed that each wheat had a distinct anthocyanin profile. Four major anthocyanins were separated from blue wheat extracts as compared to five anthocyanins in purple wheat. Cyanidin 3-glucoside was the predominant anthocyanin in purple wheat, whereas it was the second major anthocyanin in blue wheat. The predominant anthocyanin in blue wheat, making up approximately 41% of the total anthocyanin content, remains to be structurally unidentified. Blue wheat anthocyanins were thermally most stable at pH 1. Their degradation was slightly lower at pH 3 as compared to pH 5. Increasing the temperature from 65 to 95 degrees C increased degradation of blue wheat anthocyanins. Addition of SO(2) during heating of blue wheat had a stabilizing effect on anthocyanin pigments. The optimal SO(2) concentrations were 500-1000 ppm for whole meals and 1000-3000 ppm for isolated anthocyanins. Further studies are underway to identify and verify individual anthocyanins in blue wheat and their potential end uses.
Anthocyanins, present in fruits and vegetables as natural colorants, have been well characterized to possess bioactive properties. Anthocyanin components extracted from black rice (Oryza sativa L. indica) separated by gel filtration and identified using LC-MS were cyanidin 3-glucoside and peonidin 3-glucoside. A standardized extract of black rice pigmented fraction (BRE) containing known proportions of cyanidin 3-glucoside and peonidin 3-glucoside exhibited marked antioxidant activities and free radical scavenging capacities in a battery of in vitro model systems. Significant (p < 0.05) prevention of supercoiled DNA strand scission induced by reactive oxygen species (specifically, peroxyl radical and hydroxyl radicals) and suppression of the oxidative modification of human low-density lipoprotein was obtained with BRE. In addition, BRE reduced (p < 0.05) the formation of nitric oxide by suppressing inducible nitric oxide synthase expression in murine macrophage RAW264.7 cells, without introducing cell toxicity. The results of this study show that black rice contains anthocyanin pigments with notable antioxidant and anti-inflammatory properties for potential use in nutraceutical or functional food formulations.
Two hydroxycinnamate sucrose esters, 6'-O-(E)-feruloylsucrose and 6'-O-(E)-sinapoylsucrose, were isolated from methanol extracts of rice bran. Soluble and insoluble phenolic compounds as well as 6'-O-(E)-feruloylsucrose and 6'-O-(E)-sinapoylsucrose from white rice, brown rice, and germinated brown rice were analyzed using HPLC. The results demonstrated that the content of insoluble phenolic compounds was significantly higher than that of soluble phenolics in rice, whereas almost all compounds identified in germinated brown rice and brown rice were more abundant than those in white rice. 6'-O-(E)-Feruloylsucrose (1.09 mg/100 g of flour) and 6'-O-(E)-sinapoylsucrose (0.41 mg/100 g of flour) were found to be the major soluble phenolic compounds in brown rice. During germination, an approximately 70% decrease was observed in the content of the two hydroxycinnamate sucrose esters, whereas free phenolic acid content increased significantly; the ferulic acid content of brown rice (0.32 mg/100 g of flour) increased to 0.48 mg/100 g of flour and became the most abundant phenolic compound in germinated brown rice. The content of sinapinic acid increased to 0.21 mg/100 g of flour, which is nearly 10 times as much as that in brown rice (0.02 mg/100 g of flour). In addition, the total content of insoluble phenolic compounds increased from 18.47 mg/100 g of flour in brown rice to 24.78 mg/100 g of flour in germinated brown rice. These data suggest that appropriate germination of brown rice may be a method to improve health-related benefits.
Anthocyanins (ACNs) are water-soluble plant pigments that have important functions in plant physiology as well as possible health effects. Over 100 common foods were screened for ACNs, and 24 of them were found to contain ACNs. Concentrations of total ACNs varied considerably from 0.7 to 1480 mg/100 g of fresh weight in gooseberry ('Careless' variety) and chokeberry, respectively. Not only does the concentration vary, but the specific anthocyanins present in foods are also quite different. Only six common aglycones, delphinidin, cyanidin, petunidin, pelargonidin, peonidin, and malvidin, were found in all of these foods. However, their sugar moieties and acylation patterns varied from food to food. Results from this study will add to the available data for the USDA Nutrient Database of flavonoids. On the basis of the concentration data and updated food intake data from NHANES 2001-2002, the daily intake of ACNs is estimated to be 12.5 mg/day/person in the United States. Of the different aglycones, cyanidin, delphinidin, and malvidin were estimated to contribute 45, 21, and 15%, respectively, of the total ACN intake. Nonacylated contributed 77% compared to 23% from acylated ACNs.
Anthocyanin pigments from a wide variety of edible and ornamental black, blue, pink, purple, red, and white wheat, barley, corn, rice, and wild rice were identified and quantified to evaluate their potential as natural colorants or functional food ingredients. The total anthocyanin contents varied significantly and exhibited a range of 7-3276 microg/g. Some grains, such as red rice and black rice, contained a limited number of pigments, whereas others, such as blue, pink, purple, and red corns, had complex anthocyanin profiles. Of the 42 anthocyanin compounds observed, 9 were characterized by comparison of the spectroscopic and chromatographic properties with those of authentic standards. The remaining compounds were tentatively identified on the basis of spectroscopic properties and electrospray ionization mass spectra. The most abundant anthocyanins were cyanidin 3-glucoside in black and red rices and in blue, purple, and red corns, pelargonidin 3-glucoside in pink corn, and delphinidin 3-glucoside in blue wheat.
Tumor metastasis is the most important cause of cancer death and various treatment strategies have targeted on preventing the occurrence of metastasis. Anthocyanins are natural colorants belonging to the flavonoid family, and are wildly used for their antioxidant properties. Here, we provided molecular evidence associated with the anti-metastatic effects of peonidin 3-glucoside and cyanidin 3-glucoside, major anthocyanins extracted from black rice (Oryza sativa L. indica), by showing a marked inhibition on the invasion and motility of SKHep-1 cells. This effect was associated with a reduced expression of matrix metalloproteinase (MMP)-9 and urokinase-type plasminogen activator (u-PA). Peonidin 3-glucoside and cyanidin 3-glucoside also exerted an inhibitory effect on the DNA binding activity and the nuclear translocation of AP-1. Furthermore, these compounds also exerted an inhibitory effect of cell invasion on various cancer cells (SCC-4, Huh-7, and HeLa). Finally, anthocyanins from O. sativa L. indica (OAs) were evidenced by its inhibition on the growth of SKHep-1 cells in vivo.
This study was designed to evaluate the effect of an anthocyanin-rich extract from black rice on hyperlipidemia and insulin resistance in fructose-fed rats. Rats fed fructose diet for 4 weeks exhibited significantly higher plasma insulin levels and lower insulin sensitivity than the control rats fed AIN-93G diet. Dietary supplementation with the anthocyanin-rich extract (5 g/kg of high-fructose diet) prevented the development of fructose-induced insulin resistance. After fructose-induced insulin resistance had been established, 4-week treatment with the anthocyanin-rich extract (5 g/kg of high-fructose diet) or pioglitazone (270 mg/kg of high-fructose diet) ameliorated the glucose intolerance and hyperlipidemia, but the extract failed to reverse the fructose-induced hyperinsulinemia as pioglitazone did. In addition, rats supplemented by the extract exhibited lower oxidative stress than the fructose-fed controls, as indicated by the lower concentrations of plasma thiobarbituric acid reactive substances and blood oxidized glutathione. Overall, these results suggest that the anthocyanin-rich extract from black rice improves certain metabolic abnormalities associated with diets high in fructose.
Barley and its products are good sources of antioxidants. This experiment was conducted to examine the classification and concentration of phenolic compounds, proanthocyanidins, and anthocyanins in 127 lines of colored barley. Their relationship with 1,1-diphenyl-2-picrylhydrazyl (DPPH) radical scavenging activity was also examined. Barley was placed into seven groups using the colorimeter: hulled (black 1, black 2, black 3, and purple) and unhulled (black, blue, and purple). The contents of phenolic compounds and anthocyanins were analyzed by using HPLC. The average content of phenolic compounds in unhulled barley groups (268.6 microg/g) was higher than that in hulled (207.0 microg/g) (P > 0.05). The proanthocyanidins content was determined by modified vanillin assay. The average content of proanthocyanidins was significantly higher in purple and blue barley groups compared with black (P < 0.05). The content of anthocyanins varied from 13.0 to 1037.8 microg/g. Purple and blue barley groups contained higher average contents of anthocyanins than black (P < 0.05). The most common anthocyanin in the purple barley groups was cyanidin 3-glucoside, whereas delphinidin 3-glucoside was the most abundant anthocyanin in the blue and black groups. In colored barley, DPPH radical scavenging activity had high positive correlation to the content of phenolic compounds and proanthocyanidins.
Adipocyte dysfunction is strongly associated with the development of obesity and insulin resistance. It is accepted that the regulation of adipocytokine expression is one of the most important targets for the prevention of obesity and improvement of insulin sensitivity. In this study, we have demonstrated that anthocyanin (cyanidin 3-glucoside; C3G) which is a pigment widespread in the plant kingdom, ameliorates hyperglycemia and insulin sensitivity due to the reduction of retinol binding protein 4 (RBP4) expression in type 2 diabetic mice. KK-A(y) mice were fed control or control +0.2% of a C3G diet for 5 weeks. Dietary C3G significantly reduced blood glucose concentration and enhanced insulin sensitivity. The adiponectin and its receptors expression were not responsible for this amelioration. C3G significantly upregulated the glucose transporter 4 (Glut4) and downregulated RBP4 in the white adipose tissue, which is accompanied by downregulation of the inflammatory adipocytokines (monocyte chemoattractant protein-1 and tumor necrosis factor-alpha) in the white adipose tissue of the C3G group. These findings indicate that C3G has significant potency in an anti-diabetic effect through the regulation of Glut4-RBP4 system and the related inflammatory adipocytokines.
The effect of anthocyanins extracted from black soybean (Glycine max L.) seed coats on body weight, adipose tissue weight, and serum lipids was evaluated in rats fed a high fat diet (HFD). Rats were raised on a normal diet (ND) (based on the AIN-93M diet), HFD (ND supplemented with 16% lard oil), HFD containing 10% black soybean, and HFD containing 0.037% black soybean anthocyanins (equivalent to that in the 10% black soybean diet). Weight gain was significantly lowered in the rats fed HFD plus black soybean anthocyanins compared with the rats fed HFD alone (P < .05) and reversed to the level of the rats fed ND. The black soybean diet also decreased body weight gain compared with the HFD (P < .05). The black soybean anthocyanins-added diet suppressed the HFD-induced weight gain in liver intermediately and tended to decrease the weights of epididymal and perirenal fat pads. The black soybean anthocyanins were also effective in improving the lipid profile. They significantly reduced the levels of serum triglyceride and cholesterol (P < .05), while they markedly increased the high-density lipoprotein-cholesterol concentration, which was decreased in the rats fed HFD (P < .05). These results indicate that the anthocyanins in black soybean seed coats have an anti-obesity effect, which can reverse the effects of HFD on body weight, adipose tissue weight, and serum lipid contents.
Identification of anthocyanins in Japanese black rice
- K Ono
- S A Huang
Ono, K.; Huang, S. A. Identification of anthocyanins in Japanese black rice. Gifu City Women's Res. Bull. 2001, 51, 135–138.
The DeVelopment and Use of Integrated Crop Management for Rice Production
- R Clampett
- W S Nguyen
- V N Tran
t R, retention time; λ max, maximum absorption. LITERATURE CITED (1) Clampett, W. S.; Nguyen, V. N.; Tran, D. V. The DeVelopment and Use of Integrated Crop Management for Rice Production;
Schematic of the thermal degradation of cyanidin-3-glucoside in black rice. Cooking Effects on Anthocyanins in Black Rice
- R L Scalzo
- A Genna
- F Branca
Figure 6. Schematic of the thermal degradation of cyanidin-3-glucoside in black rice. Cooking Effects on Anthocyanins in Black Rice J. Agric. Food Chem., Vol. 57, No. 5, 2009 1913 (26) Scalzo, R. L.; Genna, A.; Branca, F.;
Revised manuscript received
- Hiemori
Received for review October 9, 2008. Revised manuscript received November 24, 2008. Accepted January 6, 2009. JF803153Z 1914 J. Agric. Food Chem., Vol. 57, No. 5, 2009 Hiemori et al.