BIOSYNTHESIS OF 8R-HYDROPEROXYLINOLEIC ACID BY THE FUNGUS LAETISARIA-ARVALIS

被引：39
作者：
BRODOWSKY, ID
OLIW, EH
机构：
[1] Department of Pharmaceutical Biosciences, Uppsala University Biomedical Center, Uppsala
来源：
BIOCHIMICA ET BIOPHYSICA ACTA | 1993年 / 1168卷 / 01期
关键词：
ESSENTIAL FATTY ACID; LINOLEIC ACID; MASS SPECTROMETRY; DIOXYGENASE; FUNGAL BIOSYNTHESIS; LIPOXYGENASE;
D O I：
10.1016/0005-2760(93)90267-D
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：
8-Hydroxylinoleic acid is known to be a fungicidal metabolite formed by the fungus Laetisaria arvalis (Bowers, W.S. et al. (1986) Science 232, 105-106). In the present report, the mechanism of formation of 8-hydroxylinoleic acid was investigated. L. arvalis metabolized [C-14]linoleic acid to 8-hydroperoxylinoleic acid and 8-hydroxylinoleic acid as major metabolites. The identification is based on the reduction of the hydroperoxide to an alcohol with stannous chloride and gas chromatography-mass spectrometry. The absolute configuration of the hydroxyl was determined to be R by ozonolysis of the (-)-menthoxycarbonyl derivative of 8-hydroxylinoleic acid. Linoleic acid 8 R-dioxygenase activity was present in the 100 000 X g supernatant of the cell lysate. In summary, the 8R-linoleic acid dioxygenase of L. arvalis shows many similarities with the 8R-dioxygenase recently described in the fungus Gaeumannomyces graminis.
引用
收藏
页码：68 / 72
页数：5
相关论文
共 17 条
[1]   THALLOPHYTIC ALLELOPATHY - ISOLATION AND IDENTIFICATION OF LAETISARIC ACID [J].
BOWERS, WS ;
HOCH, HC ;
EVANS, PH ;
KATAYAMA, M .
SCIENCE, 1986, 232 (4746) :105-106
[2]  
BRADFORD MM, 1976, ANAL BIOCHEM, V72, P248, DOI 10.1016/0003-2697(76)90527-3
[3]   METABOLISM OF 18-2(N-6), 18-3(N-3), 20-4(N-6) AND 20-5(N-3) BY THE FUNGUS GAEUMANNOMYCES-GRAMINIS - IDENTIFICATION OF METABOLITES FORMED BY 8-HYDROXYLATION AND BY W2 AND W3 OXYGENATION [J].
BRODOWSKY, ID ;
OLIW, EH .
BIOCHIMICA ET BIOPHYSICA ACTA, 1992, 1124 (01) :59-65
[4]  
BRODOWSKY ID, 1992, J BIOL CHEM, V267, P14738
[5]  
BRODOWSKY ID, UNPUB
[6]  
EVANS PH, 1987, ACS SYM SER, V355, P353
[7]  
HAMBERG M, 1967, J BIOL CHEM, V242, P5329
[8]   STERIC ANALYSIS OF HYDROPEROXIDES FORMED BY LIPOXYGENASE OXYGENATION OF LINOLEIC ACID [J].
HAMBERG, M .
ANALYTICAL BIOCHEMISTRY, 1971, 43 (02) :515-&
[9]  
HONECK H, 1985, PHARMAZIE, V40, P221
[10]  
MAZUR P, 1991, J CHEM SOC CHEM COMM, V20, P1486
12