The Use of Argentation Chromatography for the Analysis of Fatty Acid Esters of Polyenes: The Structure of Carotenoid Esters of Aglais urticae (Lepidoptera, Insecta)

1975 ◽  
Vol 30 (5-6) ◽  
pp. 369-378 ◽  
Author(s):  
Hartmut Kayser
Keyword(s):  
Fatty Acids ◽  
Fatty Acid ◽  
Linoleic Acid ◽  
Linolenic Acid ◽  
Unsaturated Fatty Acids ◽  
Reversed Phase ◽  
Fatty Acid Esters ◽  
Preparative Scale ◽  
Argentation Chromatography ◽  
Acid Esters

Abstract Argentation Thin-layer systems for argentation chromatography of fatty-acid esters of carotenoids have been developed. As two-dimensional reversed-phase partition system on paraffine impregnated cellulose this method permits a clear discrimination between saturated and unsaturated fatty acids. By adsorption on silver nitrate containing silica gel-G separation of carotenoid esters according to the degree of unsaturation of their fatty acids was established. With the use of known esters for comparison the fatty acids of whole carotenoid esters can be successfully analysed from minute amounts. Using these methods the carotenoid esters of pupae of Aglais urticae have been studied. The pupae contain 5.3% β-carotene, 46% lutein diester, 7.8% lutein 3-monoester, 11.7% lutein 3′-mono-ester, and 29.2% unesterified lutein. The fatty acids of the esters are linoleic acid (18:2) and linolenic acid (18:3) only. The diester fraction was composed of 70% dilinolenate, 25% linolenate-linoleate, and 5% dilinoleate. The combined monoesters consisted of 81% linolenate and 19% linoleate. The two main diesters could be isolated in a preparative scale and their structure verified by mass spectrometry. On the whole, in Aglais pupae 6.2 μg linolenic acid and 1.4 μg linoleic acid are bound to lutein. Since polyunsaturated fatty acids are of dietary origin, and represent essential factors for insect development, it is concluded, that their esterification with carotenoids may be a mode of storage comparable to the formation of glycerides.

scholarly journals Explore the gene network regulating the composition of fatty acids in cottonseed

2021 ◽  
Vol 21 (1) ◽  
Author(s):  
Lihong Ma ◽  
Xinqi Cheng ◽  
Chuan Wang ◽  
Xinyu Zhang ◽  
Fei Xue ◽  
...  
Keyword(s):  
Fatty Acids ◽  
Fatty Acid ◽  
Linoleic Acid ◽  
Linolenic Acid ◽  
Gene Network ◽  
Unsaturated Fatty Acids ◽  
Saturated Fatty Acids ◽  
Accumulation Pattern ◽  
Time Points ◽  
Expression Characteristics

Abstract Background Cottonseed is one of the major sources of vegetable oil. Analysis of the dynamic changes of fatty acid components and the genes regulating the composition of fatty acids of cottonseed oil is of great significance for understanding the biological processes underlying biosynthesis of fatty acids and for genetic improving the oil nutritional qualities. Results In this study, we investigated the dynamic relationship of 13 fatty acid components at 12 developmental time points of cottonseed (Gossypium hirsutum L.) and generated cottonseed transcriptome of the 12 time points. At 5–15 day post anthesis (DPA), the contents of polyunsaturated linolenic acid (C18:3n-3) and saturated stearic acid (C18:0) were higher, while linoleic acid (C18:2n-6) was mainly synthesized after 15 DPA. Using 5 DPA as a reference, 15,647 non-redundant differentially expressed genes were identified in 10–60 DPA cottonseed. Co-expression gene network analysis identified six modules containing 3275 genes significantly associated with middle-late seed developmental stages and enriched with genes related to the linoleic acid metabolic pathway and α-linolenic acid metabolism. Genes (Gh_D03G0588 and Gh_A02G1788) encoding stearoyl-ACP desaturase were identified as hub genes and significantly up-regulated at 25 DPA. They seemed to play a decisive role in determining the ratio of saturated fatty acids to unsaturated fatty acids. FAD2 genes (Gh_A13G1850 and Gh_D13G2238) were highly expressed at 25–50 DPA, eventually leading to the high content of C18:2n-6 in cottonseed. The content of C18:3n-3 was significantly decreased from 5 DPA (7.44%) to 25 DPA (0.11%) and correlated with the expression characteristics of Gh_A09G0848 and Gh_D09G0870. Conclusions These results contribute to our understanding on the relationship between the accumulation pattern of fatty acid components and the expression characteristics of key genes involved in fatty acid biosynthesis during the entire period of cottonseed development.

Constituents of some Curvularia species

1968 ◽  
Vol 21 (3) ◽  
pp. 783 ◽  
Author(s):  
RG Coombe ◽  
JJ Jacobs ◽  
TR Watson
Keyword(s):  
Fatty Acids ◽  
Fatty Acid ◽  
Related Species ◽  
Unsaturated Fatty Acids ◽  
Brefeldin A ◽  
Fatty Acid Esters ◽  
Curvularia Species ◽  
Acid Esters

Thirteen Gurvularia and related species were examined and the following metabolites obtained: brefeldin A, curvularin, curvulin, curvulinic acid derivatives, D-mannitol, 1,4,5,8-tetrahydroxy-2,6-dimethylanthraquinone, saturated and unsaturated fatty acids, and fatty acid esters.

Stimulation of Phosphorylcholine–Glyceride Transferase Activity by Unsaturated Fatty Acids

1973 ◽  
Vol 51 (11) ◽  
pp. 1479-1486 ◽  
Author(s):  
Michael Sribney ◽  
Eileen M. Lyman
Keyword(s):  
Fatty Acids ◽  
Fatty Acid ◽  
Unsaturated Fatty Acids ◽  
Small Extent ◽  
Fatty Acid Esters ◽  
Transferase Activity ◽  
Significant Extent ◽  
Acyltransferase Activity ◽  
Acid Esters ◽  
Stimulation Of

A number of unsaturated fatty acids markedly stimulate chicken liver microsomal phosphorylcholine–glyceride transferase (CDP-choline:1,2-diglyceride cholinephosphotransferase, EC 2.7.8.2). Oleate (0.8 mM) activates this enzyme severalfold only if a mixed diglyceride such as 1-palmitoyl-2-oleoyl-sn-glycerol is used as a substrate for the reaction. Dipalmitin and diolein incorporation into lecithin is not stimulated to any significant extent by unsaturated fatty acids. Fatty acid esters and numerous detergents either inhibit the enzyme or have no effect. Phosphorylethanolamine–glyceride transferase (CDP-ethanolamine:1,2-diglyceride ethanolaminephosphotransferase, EC 2.7.8.1) activity is only very slightly stimulated while diglyceride O-acyltransferase activity is inhibited to a small extent.

scholarly journals Fatty acids in wild hemp seeds (Cannabis sativa L. ssp. sativa var. spontanea Vavilov)

2021 ◽  
Vol 30 (1) ◽  
pp. 65-73
Author(s):  
Bojana Špirović-Trifunović ◽  
Dejan Nedeljković ◽  
Darko Stojićević ◽  
Dragana Božić
Keyword(s):  
Fatty Acids ◽  
Fatty Acid ◽  
Unsaturated Fatty Acids ◽  
Cannabis Sativa ◽  
Folk Medicine ◽  
Raw Material ◽  
Fatty Acid Esters ◽  
Relative Mass ◽  
Industrial Hemp ◽  
Acid Esters

Wild hemp (Cannabis sativa L. ssp. sativa var. spontanea) is a special variety of industrial hemp (Cannabis sativa L. ssp. sativa), which is believed to have originated from the acclimatization of industrial hemp to the ruderal habitat conditions of Eastern Europe. In Serbia it is found along roads, on field edges, stubble fields, garbage dumps etc., but also as a weed in fields. Due to the great popularity of industrial hemp, which can be used for various purposes (as raw material in food and pharmaceutical industry, in the production of gluten-free flour, biodiesel, detergents, in folk medicine), many researchers have analyzed its seeds, including analysing their fatty acids content. However, even though this knowledge can be of chemotaxonomic, ecological, evolutionary and nutritional significance, there is no data on the presence and composition of fatty acids in wild hemp seeds For the analysis of fatty acids in wild hemp seeds, the seed material was collected from two locations. After the extraction with hexane, determination of fatty acid esters was performed by capillary gas chromatography. Chromatographic peaks in the samples were identified by comparing the retention times with the retention times of the fatty acid esters in the analytical standard of a mixture of 37 fatty acid esters. The fatty acid composition is expressed as the relative mass fraction of the total fatty acids. The analysis of fatty acids in wild hemp seeds reveales the presence of 15 different acids, with content of 17.5% (U1) and 14.7% (U2) in relation to the total seed weight. Linoleic (45.3 and 47.5%) and a-linoleic (13.6 and 15.5%) acids were the most dominant. Of the 15 detected fatty acids, only 4 are saturated, with a representation of about 12%. Unsaturated fatty acids are present in a significantly higher proportion (about 88%), which indicates the nutritional value of these seeds.

scholarly journals A Bi-Enzymatic Cascade Pathway Towards FAHFAs

2021 ◽  
Author(s):  
Yan Zhang ◽  
Bekir Engin Eser ◽  
Zheng Guo
Keyword(s):  
Fatty Acids ◽  
Fatty Acid ◽  
Unsaturated Fatty Acids ◽  
Operation Mode ◽  
Hydroxy Fatty Acids ◽  
Fatty Acid Esters ◽  
One Pot ◽  
Preparative Scale

Recently discovered endogenous mammalian lipids fatty acid esters of hydroxy fatty acids (FAHFAs), proved to <a></a><a>have anti-inflammatory and anti-diabetic effects</a>. Due to their extremely low abundancies <i>in vivo</i>, forging a feasible scenario for FAHFA synthesis is critical for their use in uncovering biological mechanism or clinical trials. Here, we showcase a fully enzymatic approach, a novel <i>in vitro</i> bi-enzymatic cascade system, enabling an effective conversion of nature-abundant fatty acid into FAHFAs. Two hydratases <a></a><a>from <i>L. acidophilus</i> </a>were used for converting unsaturated fatty acids to various stereospecific hydroxy fatty acids, followed by esterification with another fatty acid catalyzed by <i>C. antarctica</i> lipase A (CALA). Various FAHFAs were synthesized in a preparative scale using this bi-enzymatic approach in a one-pot two-step operation mode. In all, we demonstrated that hydratase-CALA system promises a sustainable solution to the synthesis of structure-diverse stereospecific FAHFAs.

scholarly journals Changes in Soybean (Glycine max L.) Flour Fatty-Acid Content Based on Storage Temperature and Duration

Molecules ◽  
2018 ◽  
Vol 23 (10) ◽  
pp. 2713 ◽  
Author(s):  
Mayakrishnan Prabakaran ◽  
Kyoung-Jin Lee ◽  
Yeonju An ◽  
Chang Kwon ◽  
Soyeon Kim ◽  
...  
Keyword(s):  
Fatty Acids ◽  
Oleic Acid ◽  
Fatty Acid ◽  
Linoleic Acid ◽  
Linolenic Acid ◽  
Acid Content ◽  
Unsaturated Fatty Acids ◽  
Storage Temperature ◽  
Fatty Acid Content ◽  
Soybean Flour

Soybeans are low in saturated fat and a rich source of protein, dietary fiber, and isoflavone; however, their nutritional shelf life is yet to be established. This study evaluated the change in the stability and quality of fatty acids in raw and roasted soybean flour under different storage temperatures and durations. In both types of soybean flour, the fatty-acid content was the highest in the order of linoleic acid (18-carbon chain with two double bonds; C18:2), oleic acid (C18:1), palmitic acid (C16:0), linolenic acid (18:3), and stearic acid (C18:0), which represented 47%, 26%, 12%, 9%, and 4% of the total fatty-acid content, respectively. The major unsaturated fatty acids of raw soybean flour—oleic acid, linoleic acid, and linolenic acid—decreased by 30.0%, 94.4%, and 97.7%, and 38.0%, 94.8%, and 98.0% when stored in polyethylene and polypropylene film, respectively, after 48 weeks of storage under high-temperature conditions. These values were later increased due to hydrolysis. This study presents the changes in composition and content of two soybean flour types and the changes in quality and stability of fatty acids in response to storage temperature and duration. This study shows the influence of storage conditions and temperature on the nutritional quality which is least affected by packing material.

scholarly journals A Bi-Enzymatic Cascade Pathway Towards FAHFAs

2021 ◽  
Author(s):  
Yan Zhang ◽  
Bekir Engin Eser ◽  
Zheng Guo
Keyword(s):  
Fatty Acids ◽  
Fatty Acid ◽  
Unsaturated Fatty Acids ◽  
Operation Mode ◽  
Hydroxy Fatty Acids ◽  
Fatty Acid Esters ◽  
One Pot ◽  
Preparative Scale

Recently discovered endogenous mammalian lipids fatty acid esters of hydroxy fatty acids (FAHFAs), proved to <a></a><a>have anti-inflammatory and anti-diabetic effects</a>. Due to their extremely low abundancies <i>in vivo</i>, forging a feasible scenario for FAHFA synthesis is critical for their use in uncovering biological mechanism or clinical trials. Here, we showcase a fully enzymatic approach, a novel <i>in vitro</i> bi-enzymatic cascade system, enabling an effective conversion of nature-abundant fatty acid into FAHFAs. Two hydratases <a></a><a>from <i>L. acidophilus</i> </a>were used for converting unsaturated fatty acids to various stereospecific hydroxy fatty acids, followed by esterification with another fatty acid catalyzed by <i>C. antarctica</i> lipase A (CALA). Various FAHFAs were synthesized in a preparative scale using this bi-enzymatic approach in a one-pot two-step operation mode. In all, we demonstrated that hydratase-CALA system promises a sustainable solution to the synthesis of structure-diverse stereospecific FAHFAs.

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