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Preparation and fractionation of conjugated trienes from α‐linolenic acid and their growth‐inhibitory effects on human tumor cells and fibroblasts
Author(s) -
Igarashi Miki,
Miyazawa Teruo
Publication year - 2005
Publication title -
lipids
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.601
H-Index - 120
eISSN - 1558-9307
pISSN - 0024-4201
DOI - 10.1007/s11745-005-1365-5
Subject(s) - conjugated system , linolenic acid , chemistry , absorbance , fractionation , high performance liquid chromatography , degree of unsaturation , proton nmr , conjugated linoleic acid , chromatography , stereochemistry , fatty acid , biochemistry , organic chemistry , linoleic acid , polymer
Conjugated α‐linolenic acid (ClnA) was prepared from α‐linolenic acid (9,12,15–18∶3n−3, LnA) by alkaline treatment; we fractionated CLnA into three peaks by reversed‐phase column‐HPLC as evidenced by monitoring absorbance at 205, 235, and 268 nm. Peak I was a conjugated dienoic FA derived from LnA, whereas Peaks II and III were conjugated trienoic LnA. Proton NMR analysis showed that Peak III consisted of the all‐ trans isomer. The methylated Peak III was further divided into five peaks (Peaks IV–VIII) by silver ion column‐HPLC. Peak V, a major constituent in the Peak III fraction, was identified as conjugated 10 t ,12 t ,14 t ‐LnA by GC‐EIMS and 1 H NMR analysis. Peaks III and V, which consisted of conjugated all‐ trans trienoic LnA, had stronger growth‐inhibitory effects on human tumor cell lines than the other collected peaks and strongly induced lipid peroxidation as compared with Peaks I, II, and LnA. We propose that conjugated all‐ trans trienoic FA have the strongest growth‐inhibitory effect among the conjugated trienoic acids and conjugated dienoic acids produced by alkaline treatment of α‐LnA, and that this effect is mediated by lipid peroxidation.