Furan Fatty Acids of Lipids from Serum and Sexual Organs of Chum Salmon.

Ota, Toru; Toru, Takeshi

doi:10.2331/suisan.57.1565

Cited by 15 publications

(15 citation statements)

References 2 publications

(2 reference statements)

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“…Subsequently, these increases in F-acids were correlated with starvation (30). F-acids were detected in all fish tissues examined (28) and in their blood (35). The best source for Facids was the liver (23,24).…”

Section: Occurrencementioning

confidence: 89%

“…Measuring retention indices is often used as the only identification method, and this may be the reason why most authors have overlooked the presence of F-acids. F-acids were found in a great number of freshwater (28,29) and marine fish (29)(30)(31)(32)(33)(34)(35) (see Table 2), and some minor compounds with variations in the chain length have been detected (36). Morover, F-acids were found as constituents of cod liver oil (29,36,37).…”

Section: Occurrencementioning

confidence: 99%

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Furan fatty acids: Occurrence, synthesis, and reactions. Are furan fatty acids responsible for the cardioprotective effects of a fish diet?

Spiteller

2005

Lipids

148

170

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Furan FA (F-acids) are tri- or tetrasubstituted furan derivatives characterized by either a propyl or pentyl side chain in one of the alpha-positions; the other is substituted by a straight long-chain saturated acid with a carboxylic group at its end. F-acids are generated in large amounts in algae, but they are also produced by plants and microorganisms. Fish and other marine organisms as well as mammals consume F-acids in their food and incorporate them into phospholipids and cholesterol esters. F-acids are catabolized to dibasic urofuran acids, which are excreted in the urine. The biogenetic precursor of the most abundant F-acid, F6, is linoleic acid. Methyl groups in the beta-position are derived from adenosylmethionine. Owing to the different alkyl substituents, synthesis of F-acids requires multistep reactions. F-acids react readily with peroxyl radicals to generate dioxoenes. The radical-scavenging ability of F-acids may contribute to the protective properties of fish and fish oil diets against mortality from heart disease.

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Section: Occurrencementioning

confidence: 89%

Section: Occurrencementioning

confidence: 99%

Furan fatty acids: Occurrence, synthesis, and reactions. Are furan fatty acids responsible for the cardioprotective effects of a fish diet?

Spiteller

2005

Lipids

148

170

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“…Liver and testes lipids contain high concentrations of F-acids, which vary seasonally, depending on spawning (27,(32)(33)(34)(35). We isolated authentic F-acid methyl esters from the testes of salmon captured at Hokkaido, Japan, in September 2007.…”

Section: Resultsmentioning

confidence: 99%

“…Spiteller hypothesized that furan fatty acids (F-acids), which were first isolated from the northern pike in 1974 (22), are such naturally occurring antioxidative fatty acids that ameliorate the oxidative risk of the cellular membrane (23,24). Even though F-acid concentration is usually low, these fatty acids are widely distributed in plants and aquatic organisms (25)(26)(27)(28)(29)(30)(31)(32)(33)(34)(35)(36). The unique structural feature of Facids is the tetraalkyl-substituted furan ring, which is a rarely observed skeleton in natural products.…”

Section: Resultsmentioning

confidence: 99%

“…Additionally, to circumvent the autoxidation of the tetraalkyl-substituted furan ring on the surface of silica gel (30,39), careful manipulations are required, especially in the case of lower quantities from natural sources. Previous reports used the method of Folch et al (40) or Bligh and Dyer (41) to extract total lipids, which were further separated by silica gel into cholesteryl ester, triglycerides, and phospholipid fractions (25)(26)(27)(28)(29)(30)(31)(32)(33)(34)(35). These esters were transesterified with a methanolic sodium methoxide solution to form fatty acid methyl esters and then were investigated by GC-MS.…”

Section: Resultsmentioning

confidence: 99%

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Furan fatty acid as an anti-inflammatory component from the green-lipped mussel Perna canaliculus

Wakimoto

Kondo

Nii

et al. 2011

Proc. Natl. Acad. Sci. U.S.A.

102

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A lipid extract of Perna canaliculus (New Zealand green-lipped mussel) has reportedly displayed anti-inflammatory effects in animal models and in human controlled studies. However, the anti-inflammatory lipid components have not been investigated in detail due to the instability of the lipid extract, which has made the identification of the distinct active components a formidable task. Considering the instability of the active component, we carefully fractionated a lipid extract of Perna canaliculus (Lyprinol) and detected furan fatty acids (F-acids). These naturally but rarely detected fatty acids show potent radical-scavenging ability and are essential constituents of plants and algae. Based on these data, it has been proposed that F-acids could be potential antioxidants, which may contribute to the protective properties of fish and fish oil diets against chronic inflammatory diseases. However, to date, in vivo data to support the hypothesis have not been obtained, presumably due to the limited availability of F-acids. To confirm the in vivo anti-inflammatory effect of F-acids in comparison with that of eicosapentaenoic acid (EPA), we developed a semisynthetic preparation and examined its anti-inflammatory activity in a rat model of adjuvant-induced arthritis. Indeed, the F-acid ethyl ester exhibited more potent anti-inflammatory activity than that of the EPA ethyl ester. We report on the in vivo activity of F-acids, confirming that the lipid extract of the green-lipped mussel includes an unstable fatty acid that is more effective than EPA.

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An improved method of characterizing fatty acids by equivalent chain length values

Stránský

Jursík

Vı́tek

et al. 1992

J. High Resol. Chromatogr.

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Furan Fatty Acids of Lipids from Serum and Sexual Organs of Chum Salmon.

Cited by 15 publications

References 2 publications

Furan fatty acids: Occurrence, synthesis, and reactions. Are furan fatty acids responsible for the cardioprotective effects of a fish diet?

Furan fatty acids: Occurrence, synthesis, and reactions. Are furan fatty acids responsible for the cardioprotective effects of a fish diet?

Furan fatty acid as an anti-inflammatory component from the green-lipped mussel Perna canaliculus

An improved method of characterizing fatty acids by equivalent chain length values

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