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Fatty Acid Composition of Cold Pressed Flax Seed Oil by FAME Analysis on GC-MS

Fatty Acid Composition of Cold Pressed Flax Seed Oil by FAME Analysis on GC-MS

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Cold-pressed canola, hemp and flax seed oils were separated into their respective intact triglyc-erides via high pressure liquid chromatography (HPLC) and their fatty acids analysed. Molecular weights of the triglycerides were determined by electrospray ionization-mass spectroscopy (ESI-MS). Seven triglycerides were collected for flax seed, and tri...

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Context 1
... Total Fatty Acid Profile for Cold Pressed Flax Seed Oil a-Linolenic acid (C18:3n-3) was the most dominant fatty acid in flaxseed oil with 58.84% abundance. (Table 1). Linoleic acid was found to be the second most abundant fatty acid with 16.20%. ...
Context 2
... Flax Seed Triglyceride Fractions Linolenic acid is present on all three positions of the glycerol for vial one (Table 10) and after mass spectral analysis, flaxseed fraction 1 was determined to be trilinolenoyl-glycerol. The other fatty acids observed in the fraction may be a result of ghost/background peaks from column pre-use when operating at minimal detection limits. ...
Context 3
... Hemp Seed Triglyceride Fractions Two hempseed fractions were able to be methylated and taken through GC ( Table 11). The other fractions were not conclusive due to their low concentrations. ...
Context 4
... Canola Triglyceride Fractions Canola fraction 1 collection (Table 12) showed a high percentage of linolenic acid. The triglyceride was identified as trilinolenoyl-glycerol through mass spectral analysis. ...

Citations

... In the case of vegetable oils used as a binder for paints, such as linseed and walnut oils, the main components are triglycerides of C16 and C18 fatty acids chains, saturated, and mostly polyunsaturated. 25,26 Heating the oil with lead oxide induces the partial saponification of these triglycerides, i.e. the formation of saturated, mono-and mainly polyunsaturated lead carboxylates. A significant fraction of un-saponified molecules (tri-, di-and monoglyceride) remains in the system, as well as products of additional reactions induced by the heating process, such as oxidation, 27 isomerization, 28,29 cleavage 30 and oligomerization. ...
Article
The supramolecular and mesoscopic architectures of lead-saponified linseed oil, used by painters since the Renaissance, have been characterised and linked to their rheological properties.
... In agreement with earlier studies, the crude fat fraction of hemp seed meal fatty acids contained a higher proportion of PUFA and a lower proportion of MUFA compared with canola meal (Teh and Birch, 2013;Mungure and Birch, 2014). Especially, the concentrations of 18:2 n6 and 18:3 n3 were higher and those of 18:1 c9 and 18:1c11 were lower in dehulled hemp seed meal than in canola meal. ...
... Especially, the concentrations of 18:2 n6 and 18:3 n3 were higher and those of 18:1 c9 and 18:1c11 were lower in dehulled hemp seed meal than in canola meal. These findings agree with the studies of Birch (2013), Mungure and Birch (2014) and Mierliţă (2018). The differences in the lipid composition between the meal explain why hemp seed meal-fed cows had higher milk fat proportions of 18:2 n6 (1.99 vs. 1.56 g/100 g FA) and 18:3 n3 (0.43 vs. 0.31 g/100 g FA) than canola meal-fed cows. ...
Article
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Effects of replacing canola meal with dehulled hemp meal in the diet of lactating dairy cows on the dry matter intake (DMI), milk production, milk fatty acid profile, blood metabolites, total-tract nutrient digestibilities, and transfer of cannabinoids were determined in 12 lactating, non-pregnant Holstein cows. These cows were used in a 3 × 3 Latin Square design with 3, 3-wk experimental periods, consisting of 2 wk of adaptation and 1 wk of sampling. Cows received basal partial mixed rations supplemented with either 15% DM canola meal (CM15), 15% DM dehulled hemp meal (HM15), or 7.5% DM dehulled hemp meal and 7.5% DM canola meal (CM7.5HM7.5). Diets were formulated to be isoenergetic and isonitrogenous, but the HM15 and CM7.5HM7.5 diets contained, on average 1.2%-units more CP that the CM15 diet. The CP of the dehulled hemp meal contained less soluble protein than that of canola meal. Hence, the intake of soluble protein did not differ among diets. Canola meal contained less crude fat than hemp seed meal (3.46 vs. 8.25% DM). The lipid fraction of canola meal fat contained more oleic acid (C18:1c9; 47.3 vs, 14.9 g/100 g of fatty acids (FA)), and vaccenic acid (18:1c11; 13.7 vs. 1.2 g/100 g of FA) and less linoleic acid (C18:2 n6; 21.9 vs. 55.7g/100 g of FA), and α linolenic acid (C18:3 n3; 3.2vs. 8.9 g/100 g of FA) than the lipid fraction of hemp seed meal. The hemp seed meal contained 4.9 µg/g cannabidiol, 5.1 µg/g cannabidiolic acid, and 0.1 µg/g tertahydroxycannabinolic acid-A. Treatments did not differ in DMI, yields of milk, milk protein and milk fat, total-tract NDF digestibility, and blood plasma concentrations of β hydroxy butyrate and nonesterified FA. Apparent total-tract DM digestibility was lowest in the HM treatment, whereas the digestibility of crude protein, and the concentrations of urea, in blood, urine and milk were lowest in the CM15 treatment. Cannabinoids were not detected in urine, milk, and blood plasma. Replacing canola meal with hemp seed meal increased milk fat contents of polyunsaturated fatty acids (PUFA), which were 3.42, 3.90, and 4.25 g/100 g of FA for the CM15, CM7.5HM7.5 and HM15 treatments, respectively. Especially, the milk fat contents of 18:2 n6 (1.99 vs. 1.56 g/100 g FA) and 18:3 n3 (0.31 vs. 0.43 g/100 g FA) were increased by HM feeding. Especially, the milk fat contents of 18:2 n6 (1.99 vs. 1.56 g/100 g FA) and 18:3 n3 (0.31 vs. 0.43 g/100 g FA) were increased by hemp meal feeding Our data show that hemp seed meal is a suitable and safe replacement for canola meal as a feed for lactating dairy cows, and that this replacement increases crude protein digestibility, and urea in urine, milk and blood plasma, as well the PUFA content of milk fat.
... In two previous studies about hemp seeds, the authors reported the FA profiles for both the whole oil and their positional distribution within the TAG structure (Gao and Birch, 2016;Mungure and Birch, 2014). These two values are needed to calculate the proportions of individual FA at the sn-2 position, thereby such values were calculated to be compared with our results. ...
... This showed that LA and OA were mostly located at the sn-2 position, as found in this study. However, according to Mungure and Birch (2014), ALA and GLA were mostly located at the sn-1,3 position, which disagrees with the results of this work, as GLA was mostly located at the sn-2 position. Nonetheless, the positional distribution for GLA within the TAG structure found in this work for hemp seeds agrees with previous results for other GLA-rich seeds (Guil-Guerrero et al. 2015Shimizu and Nakanu, 2003). ...
Article
Nowadays, hemp (Cannabis sativa) seeds are receiving increased attention because of their high nutritional value. Among other nutrients, they contain a PUFA- and bioactive compounds-rich oil. Accordingly, this work was focused to establish the fatty acids (FA) content, the regiospecificity of triacylglycerols, and to quantify several bioactive compounds of relevant hemp seeds varieties and related taxa. Eight varieties of unhusked hemp seeds and eight samples of commercial husked hemp seeds were studied, and other Cannabaceae seeds: those from hop (Humulus lupulus) and European hackberry (Celtis australis). We found that all hemp seeds varieties constitute a rich source of essential PUFA as linoleic and α-linolenic acids, as well as oleic acid. PUFA were mostly distributed at the sn-2 position of triacylglycerols, thus, being highly bioaccessible, while SFA were mostly located at the sn-1,3 positions. The n–6/n–3 PUFA ratio was found to be nutritionally advantageous. Vitamin E compounds were noticeable, and γ-tocopherol was the major tocol found. Regarding phytosterols, campesterol and β-sitosterol were the most prominent compounds, while squalene content was also noticeable. Overall, the lipid fraction of hemp seeds can be considered as a source of essential and bioactive FA as well as an antioxidant- and cholesterol-lowering bioactive compounds-containing functional food.
... Consequently, analytical methods providing high chromatographic efficiency and resolution are highly demanded. The TAG analysis of hempseed oil by LC-MS has been poorly described in scientific literature [13,[40][41][42]. In most of the few cases reported, the analytical workflows were based on a preliminary LC separation, which allowed for the collection of the most abundant fractions, each corresponding to a single PN; then, the fractions were injected into a MS system for TAG identification and/or subjected to transesterification or enzymatic procedures to obtain the FA composition of each fraction. ...
... In most of the few cases reported, the analytical workflows were based on a preliminary LC separation, which allowed for the collection of the most abundant fractions, each corresponding to a single PN; then, the fractions were injected into a MS system for TAG identification and/or subjected to transesterification or enzymatic procedures to obtain the FA composition of each fraction. In this way, only the most abundant species for each PN were identified [40][41][42]. ...
Article
Full-text available
The growing demand in natural matrices that represent a source of dietary and nutraceutical molecules has led to an increasing interest in Cannabis sativa, considered to be a multipurpose, sustainable crop. Particularly, the considerable content in essential fatty acids (FAs) makes its derived-products useful food ingredients in the formulation of dietary supplements. In this research, the FA and triacylglycerol (TAG) composition of hempseed oils and flours were investigated using gas chromatography coupled to mass spectrometry and flame ionization detection as well as liquid chromatography coupled to mass spectrometry (LC-MS), respectively. Furthermore, a recently introduced linear retention index (LRI) approach in LC was successfully employed as a useful tool for the reliable identification of TAG species. A total of 30 FAs and 62 glycerolipids were positively identified in the investigated samples. Relative quantitative analyses confirmed linoleic acid as the most abundant component (50–55%). A favorable omega6/omega3 ratio was also measured in hemp-derived products, with the α-linolenic acid around 12–14%. Whereas, γ-linolenic acid was found to be higher than 1.70%. These results confirm the great value of Cannabis sativa as a source of valuable lipids, and the further improvement of the LRI system paves the way for the automatization of the identification process in LC.
... The percentages of the different lipid classes in hemp seeds are barely known. Triacylglycerols (TAG) are the main component of these seeds [7], and the most abundant TAG are LLL+LnLP (21.9%), LLLn (18.7%), and LLnLn (15.3%) that mostly contain C18:2n-6 and C18:3n-3 ( Table 2). ...
... and LLnLn (12.0-17.1%), containing C18:3n-3 (Ln), C18:2n-6 (L), and C18:1n-9 (O) [7,33] (Table 2). Flaxseed oil has 0.15 to 7.8 g 100 g -1 oil of phospholipids [8,40], from which phosphatidylcholine is the most abundant phospholipid class ( Table 3). ...
Article
Background Some plant seeds and berries have gained increased recognition due to their wide variety of bioactive compounds. Many of these foods are rich in lipids with high nutritional value, of which n-3 and n-6 essential fatty acids stand out. However, knowledge of these foodstuffs’ chemical composition and biological activity and their value as a source of healthy lipids is far from being fully explored. Objective and Methods The benefits of the intake of hemp seeds, flaxseed and açaí berries, considered functional foods, have been compiled in this review. Likewise, their general chemical composition will be described to evaluate their relevance in a healthy diet, highlighting their lipid components and nutritional lipid indices. Results and Conclusion The fibres and essential fatty acids of hemp seeds and flaxseed and the antioxidant properties of açaí berries provide them protective roles against several chronic non-communicable diseases and represent significant beneficial effects that add value to these healthy natural products. More research is needed to deepen the knowledge on their lipids’ molecular composition and bioactivity.
... The most abundant PUFA in HSO samples was proved to be LA (on average 54.7% for ITA samples and 56.9% for EEU samples), followed by ALA (from 12.3% to 17.5% for ITA samples and from 15.8% to 19.0% for EEU samples). As also reported in other papers [2,19], this study confirms that all HSO samples contained LA and ALA as major n6PUFA and n3PUFA, respectively, but it has been also reported that HSO showed a 2:1 ratio of LA and ALA [23]. The percentage of n6PUFA is very similar between ITA (57.6%) and EEU (57.5%) samples. ...
... FA sn-1 sn-2 sn-3 sn-1 sn-2 sn-3 sn-1 sn-2 sn-3 sn-1 sn-2 sn-3 Regarding HSO, TAG structural data are available, even if they are relative only to sn-2 position. Mungure and Birch (2014) carried out the pancreatic lipase treatment, considering the sn-1 and sn-3 positions equal to each other [23], while Gao and Birch (2016) evaluated the percentage distribution of FA and their positional distribution following Novozym 435 treatment of cold-pressed HSO sample from New Zealand [38]. Mungure and Birch (2014) reported that LA was the most abundant (58.2%) fatty acid at the sn-2 position in HSO, followed by OA (18.01%) and ALA (11.52%) [23]. ...
... Mungure and Birch (2014) carried out the pancreatic lipase treatment, considering the sn-1 and sn-3 positions equal to each other [23], while Gao and Birch (2016) evaluated the percentage distribution of FA and their positional distribution following Novozym 435 treatment of cold-pressed HSO sample from New Zealand [38]. Mungure and Birch (2014) reported that LA was the most abundant (58.2%) fatty acid at the sn-2 position in HSO, followed by OA (18.01%) and ALA (11.52%) [23]. The same authors have also carried out a direct HSO TAG analysis by HPLC and ESI-MS. ...
Article
Full-text available
Hemp seed oil (HSO) has received considerable attention for its health properties, especially due to unsaturated fatty acid (UFA) content. In this work, the triacylglycerol (TAG) fraction of Italian and Extra-European HSO was characterized by applying an enzymatic approach, based on the use of pancreatic lipase and sn-1,2-diacylglycerol kinase. This procedure allows determination of the intrapositional FA% composition of TAG. The results of the stereospecific analysis are useful for deepening knowledge on HSO nutritional aspects. The high percentage of UFA (88.3–89.9%), in particular essential FA (74.4–85.9%), of HSO samples in sn-2 position is important for long-term health effects, but also to enhance the use of this oil as a functional ingredient in food, cosmetic and nutraceutical fields. Furthermore, the results of total and intrapositional FA % compositions, subjected to principal component analysis, were able to differentiate HSO Italian samples from Extra-European ones. Based on the obtained results, it can be stated that the stereospecific analysis represents a potent analytical tool providing the fingerprint of TAG fraction, useful to highlight possible chemical descriptors for HSO authenticity and traceability purposes.
... Thus, the reduction of this ratio to recommended levels requires an increase in ALA consumption, which is only provided by few vegetable oils. Flax (Linum usitatissimum L.) seed oil is the richest ALA dietary source; its triacyglycerol (TAG) accumulating around 60% of this ω-3 FA [3]. ...
... LPAAT specificity and selectivity were determined as described in Nlandu Mputu et al. [19]. 3 H and 14 C labelling in PA was measured separately by scintillation counting. Specific activity is expressed as the amount of unlabelled acyl-CoA incorporated into [ 3 H] LPA-18:1 per mg protein per minute, calculated according to the amount of [ 3 H]PA produced. ...
... The proportion of ALA present at the sn-2 position of TAG is about 60% in flax seed [3]. Several metabolic pathways may control its in- [23]. ...
... This can provide information on the raw materials used, the processing conditions, and can provide a means of quality control of purity and whether the oils have been blended (Jakab et al., 2002). The characterization of several seed oils has been reported, including oil extracts from grape (Bail et al., 2008), canola, hemp and flax seeds (Mungure and Birch, 2014). ...
... HPLC-CAD offered better sensitivity and detection of lower abundance TAGs. Mungure and Birch (2014) used HPLC coupled with ESI-MS to characterise cold pressed canola, flax, and hemp seed oil. TAGs were separated by HPLC and the detection was carried out using a diode array detector at wavelengths of 215 nm (flax and canola) and 205 nm (hemp). ...
Article
Tobacco use causes serious public health concerns and causes many health problems like (asthma, COPD, stroke, cancer, etc.). While a number of pharmacological treatments are used to reduce tobacco use, they often have adverse effects. Fewer studies have assessed non-pharmacological treatments {Eicosapentaenoic acid (EPA), Docosahexaenoic acid (DHA) or fish oil} to reduce tobacco use. Omega-3 fatty acids, already known for their benefits in reducing bad cholesterol, managing diabetes, and helping with fatty liver, are now being studied for their potential impact on smoking habits. We aimed to evaluate the effect of omega-3 supplementation (flaxseed oil as a vegetarian source of alpha-linolenic acid, ALA) on tobacco craving intensity, withdrawal symptoms, and various biochemical markers in tobacco users. This single-blind, placebo-controlled study involved 104 tobacco users divided into two groups: omega-3 (n = 54) receiving 10 ml flaxseed oil daily for 6 months and placebo (n = 50). We measured tobacco craving intensity {Visual Analogue Scale (VAS)}, withdrawal symptoms {Minnesota Nicotine Withdrawal Scale (MNWS)}, demographic parameters (BMI, WHR, BP, HR), and biochemical parameters (LFT, KFT, Lipid Profile) at baseline and after 6 months. Six-month consumption of edible grade pure flaxseed oil resulted in significant lowering of BMI in omega-3 group when compared to placebo group (p = 0.0002). Also, omega-3 effectively decreased tobacco craving intensity (p < 0.0001) and its withdrawal (p < 0.0001). More intriguingly, LFT panel showed significantly lower levels of bilirubin (D) (p = 0.0216) and SGPT (p = 0.0217). Urea level (p = 0.0489) was significantly decreased while creatinine and blood urea nitrogen were comparatively decreased in omega-3 than placebo group in KFT panel. Eventually in case of lipid profile, triglycerides (p = 0.0031), LDL (p = 0.0291) and VLDL (p = 0.0055) showed significant reduction in omega-3 group. Omega-3 supplementation with flaxseed oil effectively reduces tobacco craving intensity and withdrawal symptoms, suggesting its potential for aiding tobacco cessation. Additionally, it significantly improved liver and kidney functions as well as lipid profile, highlighting its potential for broader health benefits. Trial registration This study was registered at Clinical Trial Registry-India (http://www.ctri.nic.in) with reference no. CTRI202202040681 and was performed in accordance with the Declaration of Helsinki principles.