Non-methylene-Interrupted Polyunsaturated Fatty Acids: Effective Substitute for Arachidonate of Phosphatidylinositol

We investigated effects of the non-methylene-interrupted polyunsaturated fatty acid, sciadonic acid (allcis-5,11,14-eicosatrienoic acid), on the lipid metabolism in rats, to identify the mechanism for the plasma and hepatic triacylglycerol-lowering effects of Japanese torreya (Torreya nucifera) seed oil. Sciadonic acid was isolated from torreya seed oil by the combination of urea-adduct with lipase-esterification. Sprague-Dawley (SD) male rats were fed with experimental diets containing 5% and 10% sciadonic acid based on corn oil for 2 weeks. The serum and liver triacylglycerol levels were lower in the rats fed with sciadonic acid. Considerable amounts of sciadonic acid were detected in the triacylglycerol and phospholipid in both the serum and liver of the rats fed with sciadonic acid. These observations demonstrate that sciadonic acid could modify the lipid metabolism in rats.

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“…They also reported that NMIFAs could be an effective substitute for arachidonate phosphatidylinositol. 15) Our results support their hypothesis.…”

Section: Discussionsupporting

confidence: 87%

Effects of Non-Methylene-Interrupted Polyunsaturated Fatty Acid, Sciadonic (All-cis-5,11,14-eicosatrienoic Acid) on Lipid Metabolism in Rats

Endo

Tsunokake

Ikeda

2009

Bioscience, Biotechnology, and Biochemistry

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“…In cell culture studies, SCA replaced AA in phospholipids [8,9] and inhibited prostaglandin E 2 (PGE 2 ) synthesis and type-2 cyclooxygenase (COX-2) expression in human keratinocytes and murine macrophages [5,10,11]. Our recent studies also demonstrated that PNA and Δ7-ETrA substituted for AA in phospholipids and reduced the production of pro-inflammatory mediators in RAW264.7 macrophages and human breast cancer MDA-MB-231 cells [12][13][14].…”

Section: Introductionmentioning

confidence: 87%

Phospholipid Incorporation of Non-Methylene-Interrupted Fatty Acids (NMIFA) in Murine Microglial BV-2 Cells Reduces Pro-Inflammatory Mediator Production

et al. 2015

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Sciadonic acid (SCA), pinolenic acid (PNA), and Δ7-eicosatrienoic acid (Δ7-ETrA) are three non-methylene-interrupted fatty acids (NMIFA). Using murine microglial BV-2 cells, this study determined how NMIFA incorporation modulated phospholipid fatty acid composition and the production of pro-inflammatory mediators. Each NMIFA was rapidly taken up and incorporated in BV-2 cells, resulting in the differential redistribution of total lipids. The cellular phospholipid fatty acid compositions were altered, and a significant decrease in the proportions of total monounsaturated fatty acids (MUFA) was observed while the proportions of NMIFA and its metabolites accounted for 38% of the fatty acid total. Incubation of microglial cells with NMIFA suppressed production of LPS-stimulated pro-inflammatory mediators, including nitric oxide (NO), prostaglandin E2 (PGE2), interleukin-6 (IL-6), and tumor necrosis factor-α (TNF-α), as well as the over-expression of inducible nitric oxide synthase (iNOS) and type 2 cyclooxygenase (COX-2). These inhibitory effects could be accounted for, in part, by the inactivation of mitogen-activated protein kinases (MAPK) signaling. In conclusion, Δ7-ETrA, PNA, and SCA are anti-inflammatory NMIFA that may be useful in suppressing in vitro immune responses involved in neural inflammation.

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“…1). This is biochemically exemplified by experiments showing that sciadonic acid competes with AA, both in vivo and in vitro, for the acylation of phosphatidylinositol [1,4,21,22]. With the exceptions of dihomopinolenic (7,11,14-C20:3) acid, present in the seeds from most species of the Pinaceae family [62], and dihomotaxoleic (7,11-C20:2) acid in Taxus spp.…”

Section: Figmentioning

confidence: 99%

Structures, practical sources (gymnosperm seeds), gas-liquid chromatographic data (equivalent chain lengths), and mass spectrometric characteristics of all-cis Δ5-olefinic acids

Wolff

Christie

2002

Eur. J. Lipid Sci. Technol.

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Structures, practical sources (gymnosperm seeds), gas-liquid chromatographic data (equivalent chain lengths), and mass spectrometric characteristics of all-cis ∆ ∆5-olefinic acidsIn view of the increasing interest of lipid researchers in the biological effects of all-cis ∆5-unsaturated polymethylene-interrupted fatty acids (∆5-UPIFA) from vegetable origin, this paper is concerned with their occurrence in practical sources (gymnosperm seeds), structures, and identification by gas-liquid chromatography (GLC) and mass spectrometry (MS). The use of equivalent chain lengths (ECL) determined by calculations based on available standards, in close agreement with data determined with easily available commercial gymnosperm seeds specific for each ∆5-UPIFA, allows identification of all ∆5-UPIFA. These tentative identifications are supported by GLC-MS of the appropriate (4,4-dimethyloxazoline and picolinyl ester) derivatives. ECL are particularly useful to identify ∆5-UPIFA in tissue lipids from animals experimentally fed oils containing these acids, with no interference with polyunsaturated fatty acids of endogenous origin.

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Non-methylene-Interrupted Polyunsaturated Fatty Acids: Effective Substitute for Arachidonate of Phosphatidylinositol

Cited by 35 publications

References 36 publications

Effects of Non-Methylene-Interrupted Polyunsaturated Fatty Acid, Sciadonic (All-cis-5,11,14-eicosatrienoic Acid) on Lipid Metabolism in Rats

Effects of Non-Methylene-Interrupted Polyunsaturated Fatty Acid, Sciadonic (All-cis-5,11,14-eicosatrienoic Acid) on Lipid Metabolism in Rats

Phospholipid Incorporation of Non-Methylene-Interrupted Fatty Acids (NMIFA) in Murine Microglial BV-2 Cells Reduces Pro-Inflammatory Mediator Production

Structures, practical sources (gymnosperm seeds), gas-liquid chromatographic data (equivalent chain lengths), and mass spectrometric characteristics of all-cis Δ5-olefinic acids

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