Metabolic characterization of sciadonic acid (5c,11c,14c‐eicosatrienoic acid) as an effective substitute for arachidonate of phosphatidylinositol

Tanaka, Tamotsu; Morishige, Jun‐ichi; Takimoto, Tatsunori; Takai, Y; Satouchi, Kiyoshi

doi:10.1046/j.0014-2956.2001.02423.x

Cited by 39 publications

(41 citation statements)

References 62 publications

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“…Studies in HepG2 cells, the parent line of C3A, demonstrate that 36% of cellular PtdIns contains arachidonic acid when cells are grown in DMEM containing 10% fetal bovine serum. This value increases to 80% when the medium is supplemented with arachidonic acid (14). Although the C3A cells used in the studies described here were grown in the absence of added arachidonic acid, the growth medium used for these studies (F-12) contains linoleic acid, which can be converted to arachidonic acid by the cell.…”

Section: Discussionmentioning

confidence: 97%

Regulation of de novo phosphatidylinositol synthesis

Nuwayhid

Vega

Walden

et al. 2006

Journal of Lipid Research

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Mechanisms that function to regulate the rate of de novo phosphatidylinositol (PtdIns) synthesis in mammalian cells have not been elucidated. In this study, we characterize the effect of phorbol ester treatment on de novo PtdIns synthesis in C3A human hepatoma cells. Incubation of cells with 12-O-tetradecanoyl phorbol 13-acetate (TPA) initially (1-6 h) results in a decrease in precursor incorporation into PtdIns; however, at later times (18-24 h), a marked increase is observed. TPA-induced glucose uptake from the medium is not required for observation of the stimulation of PtdIns synthesis, because the effect is apparent in glucose-free medium. Inhibition of the activation of arachidonic acid substantially blocks the synthesis of PtdIns but has no effect on the synthesis of phosphatidylcholine (PtdCho). Increasing the concentration of cellular phosphatidic acid by blocking its conversion to diacylglycerol, on the other hand, enhances the synthesis of PtdIns and inhibits the synthesis of PtdCho. The TPA-induced stimulation of PtdIns synthesis is not the result of the concomitant TPA-induced G1 arrest, because G1 arrest induced by mevastatin has no effect on PtdIns synthesis. Inhibition of protein kinase C activity blocks the stimulatory action of TPA on de novo synthesis of PtdIns but has no effect on TPA-induced inhibition.Potential sites of enzymatic regulation are discussed.-Nuwayhid, S. J., M. Vega, P. D. Walden, and M. E. Monaco. Phosphatidylinositol (PtdIns) is an essential acidic phospholipid found in the membranes of mammalian cells (1) as well as on the chromatin (2). A single molecular species composed of stearate (R9) and arachidonate (R99) accounts for z80% of the total PtdIns. There are two pathways for the synthesis of PtdIns: the de novo pathway and the salvage pathway, which converge at the level of phosphatidic acid (PtdOH). The de novo pathway uses dihydroxyacetone phosphate derived from glucose to make glycerol phosphate, which is subsequently acylated at the sn-1 position with stearate and then at the sn-2 position with arachidonate to yield PtdOH. In the salvage pathway, diacylglycerol (DAG), derived from phospholipase C-mediated hydrolysis of phosphatidylinositol 4,5-bisphosphate (PtdInsP 2 ), is converted to PtdOH through the action of DAG kinase. In the first instance, there is a net increase in PtdIns, whereas in the second, there is not. The central element of both pathways is the production of PtdOH. For the salvage pathway, it appears that the conversion of DAG to PtdOH by DAG kinase is stimulated as a result of agonist-induced polyphosphoinositide turnover. Whether this results from an increase in DAG substrate and/or an increase in DAG kinase enzyme activity is unclear. This laboratory has previously demonstrated that the two pathways can be differentiated in situ on the basis of the inhibition by triacsin C, a specific inhibitor of arachidonate-specific long-chain fatty acyl-CoA synthetase (ACSL4) in situ (3, 4).Although regulation of the salvage pathway via the activation ...

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Section: Discussionmentioning

confidence: 97%

Regulation of de novo phosphatidylinositol synthesis

Nuwayhid

Vega

Walden

et al. 2006

Journal of Lipid Research

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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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“…17) Phosphatidylcholine (PC), phosphatidylethanolamine (PE), phosphatidylserine (PS) and phosphatidylinositol (PI) were isolated from the lipid extract of Swiss 3T3 cells by two-dimensional TLC as described previously. 7) The fatty acid compositions of each phospholipid were analyzed by GC after transmethylesterification. 16) For the proliferation assay, Swiss 3T3 cells were plated in 35-mm plastic dishes at 1ϫ10 5 cells per dish in 2 ml of DMEM containing 10% FBS.…”

Section: Chemicalsmentioning

confidence: 99%

“…7) However, the metabolic fate of PMI-PUFAs in animal cells is somewhat different from that of the usual PUFAs. We have identified a metabolic route for SciA and JA.…”

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confidence: 99%