Biosynthesis of indole diterpenes, emindole, and paxilline: involvement of a common intermediate.
The key step for construction of the carbon skeleton in the indole diterpenes, paxilline, and emindole DA was examined. Intact incorporation of multiply (2)H-labeled 3-geranylgeranylindole into two different fungal metabolites proves 3-geranylgeranylindole to be a biosynthetic intermediate. These results give evidence that indole diterpenes are biosynthesized via epoxidation of a common intermediate, and the subsequent cationic cyclization, analogous to those in the steroid biosynthesis. [structure: see text]
Fueki
Shuhei
S
Division of Chemistry, Graduate School of Science, Hokkaido University, Sapporo 060-0810, Japan.
Tokiwano
Tetsuo
T
Toshima
Hiroaki
H
Oikawa
Hideaki
H
D003500:Cyclization; D004224:Diterpenes / Q000737:chemistry / Q000378:metabolism*; D032842:Emericella / Q000378:metabolism*; D007211:Indoles / Q000737:chemistry / Q000378:metabolism*; D009682:Magnetic Resonance Spectroscopy; D009183:Mycotoxins / Q000096:biosynthesis* / Q000737:chemistry; D010407:Penicillium / Q000378:metabolism*
D004224:Diterpenes; D007211:Indoles; D009183:Mycotoxins; C496869:emindole; C048220:paxilline; C030374:indole