Cyclization of natural allene oxide in aprotic solvent:: formation of the novel oxylipin methyl cis-12-oxo-10-phytoenoate

被引：7

作者：

Medvedeva, Natalia V.

Mukhtarova, Lucia S.

Mukhitova, Faina K.

Balandina, Alsu A.

Latypov, Shamil K.

Grechkin, Alexander N.

机构：

[1] Russian Acad Sci, Kazan Inst Biochem & Biophys, Kazan 420111, Russia

[2] Russian Acad Sci, AE Arbuzov Organ & Phys Chem Inst, Kazan, Russia

来源：

CHEMISTRY AND PHYSICS OF LIPIDS | 2007年 / 148卷 / 02期

基金：

俄罗斯基础研究基金会;

关键词：

allene oxide synthase; allene oxides; cyclization; cyclopentenone; oxylipins; NMR;

D O I：

10.1016/j.chemphyslip.2007.04.010

中图分类号：

Q5 [生物化学]; Q7 [分子生物学];

学科分类号：

071010 ; 081704 ;

摘要：

Allene oxide, (9Z, I I F)-12,13-epoxy-9,11-octadecadienoic acid (12,13-EOD), was prepared by incubation of linoleic acid (13S)-hydroperoxide with flaxseed allene oxide synthase (AOS) and purified (as methyl ester) by low temperature HPLC. Identification of pure 12,13-EOD was substantiated by its UV and H-1 NMR spectra and by GC-MS data for its methanol trapping product. The methyl ester of 12,13-EOD (but not the free carboxylic acid) is slowly cyclized in hexane solution, affording a novel cyclopentenone cis- 12-oxo-10-phytoenoic acid. Free carboxylic form of 12,13-EOD does not cyclize due to the exceeding formation of macrolactone (9Z)-12-oxo-9-octadecen-11-olide. The spontaneous cyclization of pure natural allene oxide (12,13-EOD) into cis-cyclopentenone have been observed first time. (c) 2007 Elsevier Ireland Ltd. All rights reserved.

引用

页码：91 / 96

页数：6

共 20 条

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