Position of Double Bond of Trans Isomers of Linoleic Acid Affects Fatty Acid Desaturation and Elongation

2009 ◽  
Vol 50 (2) ◽  
pp. 54-56
Keyword(s):  
Fatty Acid ◽  
Linoleic Acid ◽  
Double Bond ◽  
Fatty Acid Desaturation ◽  
Trans Isomers

scholarly journals TAMI-55. THE EVOLUTIONARY ENIGMA OF FATTY ACID DESATURATION IN GLIOBLASTOMA

2020 ◽  
Vol 22 (Supplement_2) ◽  
pp. ii225-ii225
Author(s):  
Nicole Oatman ◽  
Julie Reisz ◽  
Angelo D’Alessandro ◽  
Biplab Dasgupta
Keyword(s):  
Fatty Acid ◽  
Double Bond ◽  
Acyl Chain ◽  
Enzymatic Reaction ◽  
Monounsaturated Fatty Acids ◽  
Fatty Acid Desaturation ◽  
Dual Function ◽  
Storage Lipids ◽  
Essential Components ◽  
Unexpected Findings

Abstract Fatty acid desaturation is an enzymatic reaction in which a double bond is introduced into an acyl chain. Of the four functionally distinct desaturase subfamilies, the First Desaturase Family of enzymes introduce the first double bond into a saturated fatty acid, resulting in the synthesis of monounsaturated fatty acids (MUFA). MUFA are essential components of membrane and storage lipids and exert a profound influence on the fluidity of biological membranes. A disequilibrium in saturated to unsaturated fatty acid ratio alters cell growth, differentiation and response to external stimuli, and thus affects a range of pathologies including cancer. The most abundant and key First Desaturase Family enzyme is the delta 9 desaturate called Stearoyl Co-A Desaturase (SCD and SCD5 in humans, and SCD1-4 in mice). SCD desaturates Stearoyl-CoA (C18) and palmitoyl-CoA (C16) to oleoyl-CoA (C18:1) and palmitoyl-CoA (C16:1), respectively. Besides SCD, the only known First Desaturase in mammals with dual function is FADS2 which desaturates palmitate to Sapienate (C16:1, a positional isomer of palmitoleate) in skin cells. A recent study showed that some cancer cells can use FADS2 to bypass the SCD reaction. SCD and SCD5 are by far the most abundant desaturases expressed in the human brain. We made an unexpected discovery that SCD undergoes monoallelic codeletion with PTEN on chromosome 10, and is also highly methylated in glioblastoma (GBM). More surprisingly, all GBM cell lines with SCD codeletion/methylation (that expressed very little SCD protein) are completely resistant to SCD/SCD5 inhibition, yet their phospholipids contained abundant oleic acid. It is unknown if GBMs bypassed SCD, but retained the delta 9 desaturation reaction through a novel enzymatic activity. Our targeted and untargeted metabolomics studies revealed unexpected findings that cannot be explained by conventional wisdom, and may lead to identification of novel lipogenic targets in GBM.

scholarly journals DDRE-15. THE EVOLUTIONARY ENIGMA OF FATTY ACID DESATURATION IN GLIOBLASTOMA

2020 ◽  
Vol 3 (Supplement_1) ◽  
pp. i9-i9
Author(s):  
Nicole Oatman ◽  
Biplab Dasgupta
Keyword(s):  
Fatty Acid ◽  
Double Bond ◽  
Acyl Chain ◽  
Enzymatic Reaction ◽  
Monounsaturated Fatty Acids ◽  
Fatty Acid Desaturation ◽  
Dual Function ◽  
Storage Lipids ◽  
Essential Components ◽  
Unexpected Findings

Abstract Fatty acid desaturation is an enzymatic reaction in which a double bond is introduced into an acyl chain. Of the four functionally distinct desaturase subfamilies, the First Desaturase Family of enzymes introduce the first double bond into a saturated fatty acid, resulting in the synthesis of monounsaturated fatty acids (MUFA). MUFA are essential components of membrane and storage lipids and exert a profound influence on the fluidity of biological membranes. A disequilibrium in saturated to unsaturated fatty acid ratio alters cell growth, differentiation and response to external stimuli, and thus affects a range of pathologies including cancer. The most abundant and key First Desaturase Family enzyme is the delta 9 desaturate called Stearoyl Co-A Desaturase (SCD and SCD5 in humans, and SCD1-4 in mice). SCD desaturates Stearoyl-CoA (C18) and palmitoyl-CoA (C16) to oleoyl-CoA (C18:1) and palmitoyl-CoA (C16:1), respectively. Besides SCD, the only known First Desaturase in mammals with dual function is FADS2 which desaturates palmitate to Sapienate (C16:1, a positional isomer of palmitoleate) in skin cells. A recent study showed that some cancer cells can use FADS2 to bypass the SCD reaction. SCD and SCD5 are by far the most abundant desaturases expressed in the human brain. We made an unexpected discovery that SCD undergoes monoallelic codeletion with PTEN on chromosome 10, and is also highly methylated in glioblastoma (GBM). More surprisingly, all GBM cell lines with SCD codeletion/methylation (that expressed very little SCD protein) are completely resistant to SCD/SCD5 inhibition, yet their phospholipids contained abundant oleic acid. It is unknown if GBMs bypassed SCD, but retained the delta 9 desaturation reaction through a novel enzymatic activity. Our targeted and untargeted metabolomics studies revealed unexpected findings that cannot be explained by conventional wisdom, and may lead to identification of novel lipogenic targets in GBM.

TRIGLYCERIDE COMPOSITION OF SIXTEEN STRAINS OF MARINE DIATOM

2013 ◽  
Vol 5 (1) ◽  
Author(s):  
Lily M.G. Panggabean ◽  
Abdullah Rasyid ◽  
Zarrah Duniani ◽  
Yana Meliana ◽  
Indah Kurniasih
Keyword(s):  
Mass Spectrometry ◽  
Fatty Acid ◽  
Double Bond ◽  
Unsaturated Fatty Acid ◽  
Ion Trap ◽  
Carbon Chain ◽  
Highly Unsaturated Fatty Acid ◽  
Marine Diatom ◽  
Ion Trap Mass Spectrometry ◽  
Spectra Analysis

Trigliceride or triacylglicerol (TAG) composition in crude oil of sixteen strain of marine diatom has been detected by spectra analyses on an Electrospray - Ion Trap – Mass Spectrometry (ESI-IT-MS) HCT Bruker-Daltonic GmbH instrument with AgNO3 used as coordination ionization agent. Biomass samples of each microalga strain were taken from early and late stationary cultures in f/2 enriched seawater and algal oils were extracted according to Bligh and Dyer. Results from spectra analysis showed that P-Pt-P (C16:0-C16:1-C16:0) were distinguished in TAG from diatom strains Chaetoceros sp.1, Chaetoceros sp.2, Thalasiossira sp.1, Thalasiossira sp.2, Thalasiossira sp.3, Navicula sp. 1, Navicula sp. 2, Navicula sp. 3, Navicula sp. 4, Nitzschia sp. 2 and Amphora sp. In contrast, TAGs in Melosira sp. included P-P-P (C16:0-C16:0-C16:0) and P-P-O (C16:0-C16:0-C18:1) were identified. TAGs from Chaetoceros sp. were the most varies among samples, i.e. P-Pt-P (C16:0-C16:1-C16:0), A-P-M (C20:4-C16:0-C14:0), P-Pt-Lt (C16:0-C16:1-C18:3), P-Pt-A (C16:0-C16:1-C20:4), D-P-P (C22:6-C16:0-C16:0), A-Ln-P (C20:4-C18:2-C16:0). Various TAGs were also detected in Nitzschia sp.2, i.e. P-Pt-M (C16:0-C16:1-C14:0), P-Pt-P (C16:0-C16:1-C16:0), P-Pt-S (C16:0-C16:1-C18:0), P-Pt-A (C16:0-C16:1-C20:4). TAGs composition in Skeletonema strains that similar to those in Nitzschia sp.1 has longer carbon, i.e. P-P-O (C16:0-C16:0-C18:1), P-O-O (C16:0-C18:1-C18:1) and O-O-O (C18:1-C18:1-C18:1). TAGs with longer carbon chain and more double bond including highly unsaturated fatty acid C20:4 were increased with culture age in diatoms Chaetoceros sp.1, Chaetoceros sp.2, Thalasiossira sp.2, Navicula sp.1 and Nitzschia sp. 2.Keywords: diatom, TAG, ESI-IT-MS, f/2, early and late stationary

FEATURES OF THE OIL-BEARING-CROP (CHARTHAMUS) CULTIVATION UNDER THE CONTRASTIVE EDAPHIC-CLIMATIC CONDITIONS

2018 ◽  
pp. 31-37
Author(s):  
S. К. Temirbekova ◽  
Yu. V. Afanaseva ◽  
I. M. Kulikov ◽  
G. V. Metlina ◽  
S. A. Vasilchenko
Keyword(s):  
Fatty Acid Composition ◽  
Fatty Acid ◽  
Linoleic Acid ◽  
Acid Composition ◽  
Oil Content ◽  
Moscow Region ◽  
Average Weight ◽  
North Caucasus ◽  
Saratov Region ◽  
Rostov Region

The results of long-term studies of the biological, morphological and phenological features of the introduced new culture of safflower in the Central, Volga and North Caucasus regions are presented. Optimum parameters of depth of seeding (5-6 cm), seeding rates (300-350 thousand pieces/hectare or 12-14 kg), ensuring high productivity, oil content and quality of seeds are established. For the first time, the relationship between moisture availability of vegetation periods with accumulation of oil content and a change in the fatty acid composition was established. Oilseed (in untreated seeds) in the regions was from 14,5 to 31,2%, in excessively wet 2013 – 6,4% in the Moscow region and 8,6% in the Saratov region. Fatty acid composition revealed a high content of oleic acid in Krasa Stupinskaya variety – 13,6-16,8%, linoleic acid – 68,5-75,7%. The yield of oil in the Moscow region was 240 kg/ha. The yield of Krasa Stupinskaya in the Moscow Region was 0,6 t/ha, the Rostov Region 0,8 t/ha and Saratov Region 1,2 t/ha, with an average weight of 1000 seeds, respectively, by regions: 40,0 g, 47,3 g and 40,9 g. The growing season for growing seeds was 105 days in the Moscow Region, 94 days in the Rostov Region and 95 days in the Saratov Region. It has been established that excessive moistening during the flowering and seed filling period increases the harmfulness of enzyme-mycosis seed depletion (EMIS) – biological injury during maturation (enzymatic stage), followed by the seeding of the seeds with the phytopathogen Alternaria carthami Chowdhury. In the breeding programs for productivity and oil content, it is recommended to use the varieties Moldir (Kazakhstan) and Krasa Stupinskaya (FGBNU VSTISP), the fatty acid composition of which is characterized by an increased content of oleic and linoleic acid, which is of particular value for storage and use for food purposes.

Validating porcine SCD haplotype effects on fatty acid desaturation and fat deposition in different genetic backgrounds

2017 ◽  
Vol 205 ◽  
pp. 98-105 ◽  
Author(s):  
Ana I. Fernández ◽  
Cristina Óvilo ◽  
Carmen Barragán ◽  
M. Carmen Rodríguez ◽  
Luis Silió ◽  
...  
Keyword(s):  
Fatty Acid ◽  
Fat Deposition ◽  
Fatty Acid Desaturation

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.

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