Sorbicillinol, a key intermediate of bisorbicillinoid biosynthesis in Trichoderma sp USF-2690

被引:39
作者
Abe, N [1 ]
Sugimoto, O [1 ]
Arakawa, T [1 ]
Tanji, K [1 ]
Hirota, A [1 ]
机构
[1] Univ Shizuoka, Sch Food & Nutr Sci, Shizuoka 4228526, Japan
关键词
sorbicillinol; DPPH-radical scavenger; Trichoderma sp USF-2690; bisorbicillinoids biosynthesis;
D O I
10.1271/bbb.65.2271
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
In the course of our screening program for free radical scavengers from Trichoderma sp. USF-2690, we found an unidentified metabolite (1) that appeared by the method used for HPLC analysis. Metabolite 1 gradually decreased with the production of bisorbicillinoids and was easily missed during the general isolation procedure. The LC-ESI-MS (negative) analysis for I gave m/z 247 as the (M-1)(-) ion peak. The hydrolysis of synthetic 6-O-acetylsorbicillinol (+/- -2) by 0.05 M KOH and acetylation of product I in an aqueous solution indicated that the structure of 1 was (6S)-4-(2,4-hexadienoyl)-3,6-dihydroxy-2,6-dimethyl-2,4- cyclohexadien-1-one, designated sorbicillinol, a quinol that has been postulated to be important in bisorbicillinoid biosynthesis.
引用
收藏
页码:2271 / 2279
页数:9
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