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The line profile plots of chromatograms of (a) sample P6 with a predomination of Apiaceae pollen type adjusted to three red/green/blue (RGB) channels, (b) samples P1 and P10, respectively, adjusted to the green channel, (c) samples P6, P18 and P22, respectively, adjusted to the green channel. R F : retention factor
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Information on compositional, nutritional and functional properties of bee-pollen, as a health-promoting food, is essential for defining its quality. Concerning the nutritional importance of phenolic compounds, the aim of this study was to determine the phenolic profile and antioxidant activity of twenty-four bee-pollen samples collected from diffe...
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Context 1
... (RGB) images were analyzed with Image J software and raw data were further processed by a pattern recognition method. The line profile plots of chromatograms for pollen samples of particular botanical origin, according to its RGB channels, are presented in Figure 2. Differences in profile plots of the same sample are the result of different color values of each point on the chromatographic profile depending on the channel applied. ...
Context 2
... line profile plots of chromatograms for pollen samples of particular botanical origin, according to its RGB channels, are presented in Figure 2. Differences in profile plots of the same sample are the result of different color values of each point on the chromatographic profile depending on the channel applied. The line profile plots of the chromatogram corresponding to sample P6 (predominantly Apiaceae pollen type) according to RGB channel are presented in Figure 2a. Visual review revealed that the green channel was the most informative for the analyzed pollen samples (Figure 2a). ...
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... line profile plots of the chromatogram corresponding to sample P6 (predominantly Apiaceae pollen type) according to RGB channel are presented in Figure 2a. Visual review revealed that the green channel was the most informative for the analyzed pollen samples (Figure 2a). Also, phenolic line profile plots obtained for samples in which one pollen type predominates (samples P1 and P10 with a predomination of Brassicaceae and Fabaceae pollen type; P6, P18 and P22 with a predomination of Apiaceae, Ranunculaceae and Sophora pollen type, respectively) were shown to be notably different (Figure 2b,c). ...
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... review revealed that the green channel was the most informative for the analyzed pollen samples (Figure 2a). Also, phenolic line profile plots obtained for samples in which one pollen type predominates (samples P1 and P10 with a predomination of Brassicaceae and Fabaceae pollen type; P6, P18 and P22 with a predomination of Apiaceae, Ranunculaceae and Sophora pollen type, respectively) were shown to be notably different (Figure 2b,c). ...
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Citations
... There trihydroxyflavones were tentatively identified in extracts from M. varia (varieties Nakhodka, Sarga and Demetra). The CID in negative ion mode of astragalin from extracts of M. varia is shown in Figure 4C 22. Astragalin has been reported in extracts from Juglans mandshurica [48], bee pollen [49], Lonicera japonica [45], Ribes meyeri [44] and potato [50]. ...
A comparative metabolomic study of Medicago varia Mart. varieties (Demetra, Nakhodka, Sarga) grown in the Far East Three varieties of alfalfa were extracted using the supercritical CO2-extraction method. Several experimental conditions were investigated in the pressure range 50–250 bar, with the used volume of co-solvent ethanol in the amount of 1 % in the liquid phase at a temperature in the range of 31-70 ℃. The most effective extraction conditions are: pressure 250 Bar and temperature 60℃ for M. varia. M. varia contain various phenolic compounds and sulfated polyphenols with valuable biological activity. Tandem mass-spectrometry (HPLC-ESI – ion trap) was applied to detect target analytes. There were tentatively identified 103 bioactive compounds in extracts from aerial parts of alfalfa (fifty-nine compounds from polyphenol group and forty-four compounds from other chemical groups). For the first time, twenty-one chemical constituents from polyphenol group (flavones Formononetin, Chrysoeriol, Cirsimaritin, Cirsiliol, Cirsilineol, tricin-O-hexoside, Apigenin C-glucose C-deoxyhexoside, Apigenin 7-O-diglucuronide, 2'-Hydroxygenistein 4',7-O-diglucoside, etc.) and six chemical constituents from other chemical groups (saponins: Soyasaponin II, Soyasaponin gamma g, Soyasaponin I, Soyasaponin Bd, Soyaysaponin beta g, etc.) were identified in aerial parts of M. varia.
... High-performance thin-layer chromatography (HPTLC) was mainly used in the analysis of bee pollen samples for fingerprinting [4,5,12] with chemometric evaluation [12] and bioautography [4], in the past, also for testing the purity of isolates [13]. HPTLC separations of phenolic compounds in bee pollen samples were performed on silica gel plates [4,5,12] developed with developing solvents containing formic acid [5,12] or formic acid and acetic acid [4,5]. ...
... High-performance thin-layer chromatography (HPTLC) was mainly used in the analysis of bee pollen samples for fingerprinting [4,5,12] with chemometric evaluation [12] and bioautography [4], in the past, also for testing the purity of isolates [13]. HPTLC separations of phenolic compounds in bee pollen samples were performed on silica gel plates [4,5,12] developed with developing solvents containing formic acid [5,12] or formic acid and acetic acid [4,5]. ...
... High-performance thin-layer chromatography (HPTLC) was mainly used in the analysis of bee pollen samples for fingerprinting [4,5,12] with chemometric evaluation [12] and bioautography [4], in the past, also for testing the purity of isolates [13]. HPTLC separations of phenolic compounds in bee pollen samples were performed on silica gel plates [4,5,12] developed with developing solvents containing formic acid [5,12] or formic acid and acetic acid [4,5]. When coupling HPTLC and mass spectrometry (MS) via elution head-based interface, acids in the developing solvent cause intense background signals of clusters (e.g. ...
High-performance thin-layer chromatographic (HPTLC) silica gel and amino plates in combination with developing solvents containing formic and acetic acid were examined for HPTLC‒multi-stage mass spectrometry (MS ⁿ ) analyses of chestnut bee pollen samples from Slovenia and Türkiye. Ethyl acetate‒formic acid‒acetic acid‒water (10:1.1:1.1:2.6, V/V ) and ethyl acetate‒dichloromethane‒formic acid‒acetic acid (10:2.5:1:1.1, V/V ) were used for development of silica gel and amino plates, respectively. Twofold pre-development was required for the developed HPTLC‒MS ⁿ methods. The first pre-development was performed with methanol‒formic acid (10:3, V/V ) for silica gel plates and methanol‒formic acid (10:5, V/V ) for amino plates. The second pre-development with methanol was equal for both types of the plates. Using the developed HPTLC‒MS ⁿ methods, five phenylamides (spermidines), six isorhamnetin glycosides and gluconic acid were identified in both chestnut bee pollen samples. Glycosylated phenolic acid (caffeic acid-hexoside) was detected only in the Turkish bee pollen sample. To the best of our knowledge, this is the first report on isorhamnetin-(hexosyl)hexoside, isorhamnetin-acetylhexoside, isorhamnetin-(pentosyl-deoxyhexosyl)hexoside and caffeic acid-hexoside in chestnut bee pollen. This is also the first report on isorhamnetin-(pentosyl-deoxyhexosyl)hexoside and caffeic acid-hexoside in any bee products.
... Through pollen analysis, most researchers classified HBP as multifloral or monofloral (Alimoglu et al., 2021;Aylanc et al., 2023;Gercek et al., 2021). However, Barth et al. (2010), Mosić et al. (2019), and Nandi and Karmakar (2018) proposed a more detailed classification, covering mono, bi, tri, and multifloral categories. In this study, the palynological analysis of bee pollen samples from Türkiye has been assessed for the first time using this approach. ...
Honey bee pollen (HBP) is a hive product produced by worker bees from floral pollen grains agglutination. It is characterized by its excellent nutritional and bioactive composition, making it a superior source of human nutrition. This study aimed to evaluate the monofloral bee pollen samples, including Cistus, Crataegus monogyna, Cyanus, Elaeagnus angustifolia, Papaver somniferum, Quercus, Salix, Sinapis, and Silybum from Türkiye according to palynological analysis, antioxidant activity, phenolic profiles, and color. The phenolic profiles were detected using ultra‐high performance liquid chromatography coupled with tandem mass spectrometry. Bee pollens were categorized into monofloral, bifloral, and multifloral, underscoring the significance of confirming the botanical source of them depending on palynological analyses. Total phenolic content (TPC) of bee pollens ranged from 4.5 to 14.4 mg gallic acid/g HBP. The samples exhibited antioxidant activity for 2,2′‐azinobis‐(3‐ethylbenzothiazoline‐6‐sulfonic acid) (ABTS •⁺) ranging from 94.9 to 233.5 µmol trolox/g HBP, whereas lower values were seen for 2,2‐diphenyl‐1‐picrylhydrazyl (DPPH•) ranging from 25.86 to 70.81 µmol trolox/g HBP. A yellowish‐red tint color was also displayed for whole samples, whereas only E. angustifolia bee pollen indicated a darker color (L* = 31.6). Among the phenolic compounds, luteolin, kaempferol, isorhamnetin, rutin, and genistein were the most abundant, and their profiles varied across the samples. It was also observed that TPC, antioxidant activities, and polyphenol composition were higher in samples containing pollen grains of P. somniferum, Quercus, Plantago, and E. angustifolia species.
Practical Application
The increasing number of new findings on honey bee pollen is crucial to food science and technology. In this sense, this study offers a robust method for verifying the authenticity and quality of 11 monofloral bee pollens, which is crucial for the food industry. It also identifies potential sources of high‐quality pollen, benefiting producers, and consumers seeking superior bee pollen products.
... Kaempferol favonoids are characterized by a deprotonated kaempferol aglycone fragment at m/z 284/285, and other characteristic product ions at m/z 255 and 227 further confrm the identifcation of the kaempferol aglycone[43]. Compound 5 gave a (M-H) − ion at m/z 533.093 while its MS/MS fragmentation gave a base peak at m/z 285.043, due to the loss of the malonyl hexose moiety, and was thus identifed as kaempferol malonyl hexose[51]. Compound 6 gave a (M-H) − ion at m/z 592.785, while its MS/MS fragmentation gave a base peak at m/z 285.043 due to the loss of the rutinoside sugar and was identifed as kaempferol rutinoside[52]. ...
Moringa oleifera Lam. is a functional tree that is known to produce a variety of metabolites with purported pharmacological activities. It is frequently called the “miracle tree” due to its utilization in numerous nutraceutical and pharmacological contexts. This study was aimed at studying the chemical space of M. oleifera leaf extracts through molecular networking (MN), a tool that identifies metabolites by classifying them based on their MS-based fragmentation pattern similarities and signals. In this case, a special emphasis was placed on the flavonoid composition. The MN unraveled different molecular families such as flavonoids, carboxylic acids and derivatives, lignin glycosides, fatty acyls, and macrolactams that are found within the plant. In silico annotation tools such as network annotation propagation (NAP) and DEREPLICATOR, an unsupervised substructure identification tool (MS2LDA), and MolNet enhancer were also explored to further compliment the classic molecular networking output within the Global Natural Product Social (GNPS) site. In this study, common flavonoids found within Moringa oleifera were further annotated using MS2LDA. Utilizing computational tools allowed for the discovery of a wide range of structurally diverse flavonoid molecules within M. oleifera leaf extracts. The expansion of the flavonoid chemical repertoire in this plant arises from intricate glycosylation modifications, leading to the creation of structural isomers that manifest as isobaric ions during mass spectrometry (MS) analyses.
... The presence of phytochemical compounds as secondary metabolites such as coumarin derivatives in the extracts of various species of prangos plant has been reported in different studies (Meshkatalsadat and Mirzaei, 2007;Badalamenti et al., 2022). In addition, quercetin and myristin derivatives have been identified as glycosidic flavonoids in Prangos uechtritzii (Schieber et al., 2002;Mosić et al., 2019). In the study by Dall'Acqua et al. (2022), who identified the bioactive compounds in prangos species by HPLC, the obtained secondary metabolites were grouped into concentrated tannins, hydrolyzable tannins, coumarins, and flavonoid derivatives (Dall'Acqua et al., 2022). ...
Prangos ferulacea plant is very popular in Iran due to its unique properties in treating diseases and its special flavor. To check the characteristics of this plant, first, its extract was extracted using the maceration method. Its chemical composition was investigated using high-performance liquid chromatography (HPLC) that p-coumaric was identified as its main compound, and Fourier-transform infrared spectroscopy (FTIR) showed the presence of functional groups related to phenolic, flavonoid, tannins, and carboxylic acids such as caffeic acid and coumaric acid composition. Total phenol content (TPC), total flavonoid content (TFC), and beta-carotene were equal to 202.04 ± 5.46 mg gallic acid equivalent (GAE)/g dry weight, 1,909.46 ± 13 μg quercetin (QE)/g of dry weight, and 2.91 mg/100 g. The antioxidant property of the extract was evaluated using 2,2-Diphenyl-1-picrylhydrazyl (DPPH) and 2,2′-azino-bis (3-ethylbenzothiazoline-6-sulphonic acid (ABTS) free radical scavenging and ferric reducing antioxidant power assay (FRAP). According to the IC50 obtained for DDPH (274 ± 7.2 μg/mL) and ABTS (120.45 ± 9.6 μg/mL) and FRAP values [1.92 ± 0.05 μg ascorbic acid equivalent (AAE)/g of extract], this extract had high antioxidant properties. Cytotoxicity was evaluated against the survival of HT 29 cells that IC50 was 82.15 ± 0.02 μg/mL. The antimicrobial property of the extract was calculated using disk diffusion agar (DDA), well diffusion agar (WDA), minimum inhibitory concentration (MIC), and minimum bactericidal concentration (MBC). Listeria monocytogenes has the highest sensitivity to this extract and inhibition zone based on DDA and WDA method and with an MIC and MBC equal to 16 and 128 mg/mL has the least resistance. The morphology change of L. monocytogenes strain was proved through scanning electron microscope (SEM) and confocal laser scanning microscopy (CLSM). The extract caused a significant reduction in the transcription of genes involved in the film formation ability of L. monocytogenes . The obtained results fully prove the very practical and pragmatic characteristics of P. ferulacea .
... These types of compounds are the main flavonoids located in the exine membrane. Therefore, they have been found as part of the flavonoid composition of bee pollen of diverse botanical origins [33,42,56,57]. It should be noted that these flavonoids have been detected in various extracts of chestnut shell, inner shell, bur leaves, and products, as well as in the flowers, relating their presence to a botanical origin [58]. ...
Bee pollen is a rich bee product, from the point of view of its nutritional and functional chemical characteristics. The chemical composition of bee pollen and its properties make this product an excellent food supplement for the human diet, due to its various functional bioactivities, such as having antioxidant, antibacterial, antifungal, and anti-inflammatory properties. These properties depend on the botanical origin of the bee pollen. Castanea sativa bee pollen is one of the most important types of pollen collected in the northwest of the Iberian Peninsula. Thus, the phenolic profile of Castanea bee pollen was featured in this study. For this, 11 samples of Castanea were selected through prior colorimetric separation using the CIELab* scale and verified with palynological analysis. Identification of the main phenol compounds was performed through LC/DAD/ESI-MSn analysis. The phenols compounds were quantified using calibration curves for caffeic acid, quercetin, and naringenin. The main results showed a profile formed of 19 compounds for all samples, although quantitative differences were found. Most of these compounds were phenolamides, with N1, N5, and N10-tricaffeoylspermidine being significantly (p < 0.05) the most abundant. Three isorhamnetin glycoside derivatives and one naringenin were also identified. The richness in phenolamides of Castanea bee pollen identified in this study suggests Castanea bee pollen as a functional food, owing to its healthy properties.
... higher level than in the other. Isorhamnetin 3-O-(2"-rhamnosyl)-hexoside has been detected in Serbian bee-pollen [93], while luteolin glycosides were already determined in fruits of pear cultivars [94]. ...
The topography and morpho-anatomical characteristics of floral nectaries and the chemical analysis of nectar have been studied in seven pear cultivars with different susceptibility to Erwinia amylovora. The susceptible cultivar Williams, the moderately resistant cultivars Bella di guigno, Poire de Cure and the low susceptible cultivar Alexander Lucas originated from Pyrus communis, while highly resistant cultivars Chojuro and Nijisseiki from P. pyraster and Kieffer as interspecies hybrid P. communis × P. pyraster were included in this experiment and studied for the first time. Large differences in size and structure of the nectaries were observed in these seven pear cultivars. The epidermal cells were with cuticle being more or less striated in Alexander Lucas, Kieffer and Williams. Resistant cultivars had a narrow, elongated cell shape of epidermal cells while those susceptible had an isodiametric. Stomata were mesomorphic in all cultivars except in Poire de Cure and Williams, being slightly xeromorphic since they were situated in deep hollows. Guard cells of the modified stomata were much larger in resistant cultivars. Hypanthium cells were larger in resistant compared to susceptible cultivars. The most abundant sugars were glucose, fructose, sorbitol and sucrose in nectar of all studied pear cultivars. The resistant cultivars (Chojuro, Kieffer and Nijisseiki) had a ~2-fold higher level of sorbitol and galactose, ~2.2-fold higher isomaltose, ~2.7-fold turanose, ~3.35-fold maltose, ~4.4-fold melibiose and ~12.7-fold higher melesitose compared to susceptible cultivars. The sum of quantified phenolic acids varied from 0.049 (Williams) up to 4.074 µg CAE/mL (Kieffer), while flavonoid glycosides levels ranged from 1.224 (Williams) up to 11.686 µg RE/mL (Nijisseiki). In the nectar of the resistant cultivars, rutin, apigetrin, together with patuletin and luteolin glycosides were detected but not in susceptible cultivars, which could be considered as the markers of resistance.
... Image acquisition under 254 nm, 366 nm, and visible light illumination gives nine channels of information, where fluorescence of the analyzed compounds as well as its quenching on fluorescent plate is a main phenomenon responsible for the obtained information [26,27]. Such multichannel datasets are fantastic targets of advanced pattern recognition algorithms [28,29]. ...
The advantages of high dynamic range (HDR) imaging in videodensitometry are presented and discussed on the example of Gentiana extract thin-layer fingerprints visualized under 254 nm. An inexpensive microscope camera, together with security surveillance lens, mounted instead of original camera on videodensitometry chamber, allows to grab HDR images with high tonal range using Python scripts and OpenCL library. HDR imaging preserves linearity in whole tonal range and does not destroy details in the brightest and darkest plate regions, so it can be seen as a good alternative to classical videodensitometry. Moreover, the tonemapping of HDR images can be used to present a plate photograph with enhanced visibility of weak spots and other details. Principal component analysis done on nine classic exposures and HDR image proves that HDR image contains the highest amount of extracted information from the thin-layer chromatographic plate.
... Phenolic compounds are important for the development and functions of pollen of anemophilous plants: they participate in the synthesis of sporopollenin and affect its stability [5,53], while bioactive properties help to protect the exine and intine [54]. Pollen phenolic compounds in the human diet are studied for both quantification and bioactivity determination [8,21,22,55]. Meanwhile, knowledge on the emission of phenolic compounds into the environment from naturally degrading pollen in ecosystems is very scarce. ...
In this study, phenolic compounds and their antioxidant activity in the pollen of anemophilous Betula and Pinus were determined. Spectrophotometric, high-performance thin-layer and liquid chromatography methods were applied. Free phenolic compounds (free PC) and phenolic compounds bound to the cell wall (bound PC) were analysed in the pollen extracts. Regardless of the pollen species, their content was 20% higher than that in bound PC extracts. Pinus pollen extracts contained 2.5 times less phenolic compounds compared to Betula. Free PC extraction from the deeper layers of Pinus pollen was minimal; the same content of phenolic compounds was obtained in both types of extracts. The bioactivity of pollen (p < 0.05) is related to the content of phenolic compounds and flavonoids in Betula free PC and in bound PC, and only in free PC extracts of Pinus. Rutin, chlorogenic and trans-ferulic acids were characterised by antioxidant activity. Phenolic acids accounted for 70–94%, while rutin constituted 2–3% of the total amount in the extracts. One of the dominant phenolic acids was trans-ferulic acid in all the Betula and Pinus samples. The specific compounds were vanillic and chlorogenic acids of Betula pollen extracts, while Pinus extracts contained gallic acid. The data obtained for the phenolic profiles and antioxidant activity of Betula and Pinus pollen can be useful for modelling food chains in ecosystems.
... In addition, 25 flavonoid glycosides were found in 18 floral types of bee pollen. Compounds B1, B3, B6, B7, B9, B14, B16, B17, B18, B20, and B22 were similarly identified in previous studies (Giampieri et al., 2022;Mosić et al., 2019;Pinto et al., 2010;Thakur & Nanda, 2020;Truchado, Ferreres, & Tomas-Barberan, 2009;Turner, Nielsen, O'Connor, & Burton, 2006;Wu, Shao, Li, Zhang, & Wang, 2015). Compounds B2, B4, B5, B8, B10, B11, B12, B13, B15, B19, B21, B23, B24, and B25 seem to be firstly identified in bee pollen. ...
This study aimed at investigating phenolamides and flavonoid glycosides in 20 types of monofloral bee pollen. The plant origins of pollen samples were determined by DNA barcoding, with the purities to over 70%. The 31 phenolamides and their 33 cis/trans isomers, and 25 flavonoid glycosides were identified; moreover, 19 phenolamides and 14 flavonoid glycosides as new-found compounds in bee pollen. All phenolics and flavonoids are present in the amidation or glycosylation form. The MS/MS cleavage modes of phenolamides and flavonoid glycosides were summarized. Isorhamnetin-3-O-gentiobioside presented the highest levels 23.61mg/g in apricot pollen. Phenolamides in 11 types of pollen constituted over 1% of the total weight, especially 3.9% in rose and 2.8% in pear pollen. Tri-p-coumaroyl spermidine and di-p-coumaroyl-caffeoyl spermidine respectively accounted for over 2.6% of the total weight in pear and rose pollen. The richness in phenolamides and flavonoid glycosides can offer bee pollen more bioactivities as functional foods.
