Multiple Oxidative Modifications in the Ophiobolin Biosynthesis: P450 Oxidations Found in Genome Mining.
Heterologous expression of four candidate genes found in ophiobolin gene clusters from three fungal strains was employed to elucidate the late-stage biosynthetic pathway of phytotoxin ophiobolin. Expression of oblBAc (cytochrome P450) from the cryptic gene cluster gave unexpected products, and that of oblBBm/oblBEv from the gene cluster of ophiobolin producers, with oblDBm as the transporter, yielded intermediate ophiobolin C through an unusual four-step oxidation process. The observation made in this study may provide a useful guideline for the elucidation of genuine biosynthetic pathways of natural products.
Division of Chemistry, Graduate School of Science, Hokkaido University , Sapporo 060-0810, Japan.
Koji
K
Narita
Division of Chemistry, Graduate School of Science, Hokkaido University , Sapporo 060-0810, Japan.
Ryota
R
Chiba
Division of Chemistry, Graduate School of Science, Hokkaido University , Sapporo 060-0810, Japan.
Atsushi
A
Minami
The United Graduate School of Agricultural Sciences, Tottori University , Tottori 680-8553, Japan.
Motoichiro
M
Kodama
School of Pharmacy, Iwate Medical University , Yahaba, Iwate 028-3694, Japan.
Isao
I
Fujii
Graduate School of Agricultural Science, Tohoku University , Sendai 981-8555, Japan.
Katsuya
K
Gomi
Division of Chemistry, Graduate School of Science, Hokkaido University , Sapporo 060-0810, Japan.
Hideaki
H
Oikawa
D003577:Cytochrome P-450 Enzyme System / Q000235:genetics / Q000378:metabolism*; D008968:Molecular Conformation; D010084:Oxidation-Reduction; D054830:Sesterterpenes / Q000096:biosynthesis* / Q000737:chemistry / Q000235:genetics
D054830:Sesterterpenes; C002884:ophiobolins; D003577:Cytochrome P-450 Enzyme System