A General Convergent Strategy for the Synthesis of Tetra‐Substituted Furan Fatty Acids (FuFAs)

Wang, Yamin; Pritchard, Gareth J.; Kimber, Marc C.

doi:10.1002/ejoc.202000234

Cited by 9 publications

(2 citation statements)

References 48 publications

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“…The furan fatty acids (FuFAs) are fatty acids with a furan ring. To date, thirty different structures have been identified (Glass et al, 1974;Wang et al, 2020b). The most common FuFAs are methylated or dimethylated forms.…”

Section: Structure and Biosynthesismentioning

confidence: 99%

Potential favourable health effects of some dietary uncommon fatty acids

Coudray

Durand

Balas

et al. 2021

OCL

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In addition to the major fatty acids widely studied, our diet contains many bioactive fatty acids less frequently investigated such as n-3 docosapentaenoic acid (n-3 DPA), natural trans fatty acids, conjugated fatty acids (CLAs), furan fatty acids (FuFAs), branched chain fatty acids (BCFAs) and fatty acid esters of hydroxyl fatty acids (FAHFAs). Many of them may have beneficial health effects, particularly in the prevention of cardiovascular diseases, inflammation and metabolic disorders such as diabetes. This review aims to give a brief overview of the current knowledge on these lipids. Thus, information about biosynthesis, food and tissue content, daily intake, biological and potential health effects of these fatty acids is provided.

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Section: Structure and Biosynthesismentioning

confidence: 99%

Potential favourable health effects of some dietary uncommon fatty acids

Coudray

Durand

Balas

et al. 2021

OCL

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“…However, the final structural proof of uFuFA isomers had not been achieved. Unfortunately, multi-step syntheses of (chain-saturated) FuFAs [ 17 , 18 ] are difficult to conduct, and paired with additional double bonds and the geometry issue of uFuFAs, it appeared unrealistic to be feasible in reasonable time. Vice versa, knowledge of the exact uFuFA structures would simplify their later synthesis by experts.…”

Section: Introductionmentioning

confidence: 99%

Enrichment and structural assignment of geometric isomers of unsaturated furan fatty acids

Müller,

Conrad,

Hammerschick

et al. 2023

Anal Bioanal Chem

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Furan fatty acids (FuFAs) are valuable minor fatty acids, which are known for their excellent radical scavenging properties. Typically, the furan moiety is embedded in an otherwise saturated carboxyalkyl chain. Occasionally, these classic FuFAs are accompanied by low amounts of unsaturated furan fatty acids (uFuFAs), which additionally feature one double bond in conjugation with the furan moiety. A recent study produced evidence for the occurrence of two pairs of E-/Z-uFuFA isomers structurally related to saturated uFuFAs. Here, we present a strategy that allowed such trace compounds to be enriched to a level suited for structure determination by NMR. Given the low amounts and the varied abundance ratio of the four uFuFA isomers, the isolation of individual compounds was not pursued. Instead, the entire isomer mixture was enriched to an amount and purity suitable for structure investigation with contemporary NMR methods. Specifically, lipid extracted from 150 g latex, the richest known source of FuFAs, was subsequently fractionated by countercurrent chromatography (CCC), silver ion, and silica gel column chromatography. Analysis of the resulting mixture of four uFuFAs isomers (2.4 mg in an abundance ratio of 56:23:11:9) by different NMR techniques including PSYCHE verified that the structures of the two most abundant isomers were E-9-(3-methyl-5-pentylfuran-2-yl)non-8-enoic acid and E-9-(3-methyl-5-pent-1-enylfuran-2-yl)nonanoic acid. Additionally, we introduced a computer-based method to generate an averaged chromatogram from freely selectable GC/MS runs of CCC fractions without the necessity of pooling aliquots. This method was found to be suitable to simplify subsequent enrichment steps. Graphical Abstract

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Synthesis of polysubstituted furan-3(4)-carboxylates (microreview)

Gomonov

Pelipko

2022

Chem Heterocycl Comp

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A General Convergent Strategy for the Synthesis of Tetra‐Substituted Furan Fatty Acids (FuFAs)

Cited by 9 publications

References 48 publications

Potential favourable health effects of some dietary uncommon fatty acids

Potential favourable health effects of some dietary uncommon fatty acids

Enrichment and structural assignment of geometric isomers of unsaturated furan fatty acids

Synthesis of polysubstituted furan-3(4)-carboxylates (microreview)

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