Functional analyses of cytochrome P450 genes responsible for the early steps of brassicicene C biosynthesis

被引：20

作者：

Hashimoto, Makoto ^{[1
]}

Higuchi, Yusuke ^{[2
]}

Takahashi, Shunji ^{[3
,4
]}

Osada, Hiroyuki ^{[3
,4
]}

Sakaki, Toshiyuki ^{[1
]}

Toyomasu, Tomonobu ^{[5
]}

Sassa, Takeshi ^{[5
]}

Kato, Nobuo ^{[2
]}

Dairi, Tohru ^{[1
]}

机构：

[1] Toyama Prefectural Univ, Biotechnol Res Ctr, Toyama 9390398, Japan

[2] Osaka Univ, Inst Sci & Ind Res, Osaka 5670047, Japan

[3] RIKEN, Antibiot Lab, Wako, Saitama 3510198, Japan

[4] RIKEN, Dept Biol Chem, Wako, Saitama 3510198, Japan

[5] Yamagata Univ, Dept Bioresource Engn, Yamagata 9978555, Japan

来源：

BIOORGANIC & MEDICINAL CHEMISTRY LETTERS | 2009年 / 19卷 / 19期

关键词：

Diterpene; Brassicicene C; Biosynthesis; Cytochrome P450; DIFFERENTIATION-INDUCING AGENT; PHOMOPSIS FUSICOCCUM AMYGDALI; PLANT-GROWTH REGULATOR; COTYLENIN-A; MYELOID-LEUKEMIA; FUNGUS; CELLS; CARCINOMA; ALPHA;

D O I：

10.1016/j.bmcl.2009.08.026

中图分类号：

R914 [药物化学];

学科分类号：

100701 ;

摘要：

We previously revealed that Orf8 and Orf6, which were identified in the brassicicene C biosynthetic gene cluster in Alternaria brassicicola strain ATCC96836, were fusicoccadiene (FD) synthase and 16-O-methyltransferase, respectively. In the present Letter, the early biosynthetic steps after the formation of FD were investigated. Plasmids carrying the FD synthase gene, one (or two) of five cytochrome P450 genes (orf1, orf2, orf5, orf7, and orf11) identified in the cluster and a cytochrome P450 reductase gene cloned from strain ATCC96836 were constructed and introduced into Saccharomyces cerevisiae. Based on the structures of the compounds produced by the transformants, Orf1 is suggested to be an 8 beta-hydroxylation enzyme that yields FD 8 beta-ol ( 4), followed by 16-hydroxylation by Orf7 to produce FD 8 beta 16-diol ( 5). (C) 2009 Elsevier Ltd. All rights reserved.

引用

页码：5640 / 5643

页数：4

共 20 条

[1] Cotylenin A, a plant-growth regulator, induces the differentiation in murine and human myeloid leukemia cells [J].