KEGG   PATHWAY: map00403
Entry
map00403                    Pathway                                

Name
Indole diterpene alkaloid biosynthesis
Description
Indole diterpene alkaloids are a group of meroterpenoids consisting of a partial diterpene structure with four isoprene units and an indole moiety. The common cyclic diterpene skeleton is derived from geranylgeranyl diphosphate (GGPP) and an indole moiety is derived from tryptophan or a tryptophan precursor. They are combined in the initial step of biosynthetic reactions that generate paspaline, the first stable and less modified form required for other forms. Most indole diterpene alkaloids have potent mammalian tremorgenic activities, such as ryegrass staggers in livestock, and some have anti-insect properties. This map shows examples of indole diterpene alkaloids isolated from filamentous fungi.
Class
Metabolism; Biosynthesis of other secondary metabolites
Pathway map
map00403  Indole diterpene alkaloid biosynthesis
map00403

Module
M00661  Paspaline biosynthesis, geranylgeranyl-PP + indoleglycerol phosphate => paspaline [PATH:map00403]
Reference
  Authors
Saikia S, Nicholson MJ, Young C, Parker EJ, Scott B
  Title
The genetic basis for indole-diterpene chemical diversity in filamentous fungi.
  Journal
Mycol Res 112:184-99 (2008)
DOI:10.1016/j.mycres.2007.06.015
Reference
  Authors
Saikia S, Parker EJ, Koulman A, Scott B
  Title
Four gene products are required for the fungal synthesis of the indole-diterpene, paspaline.
  Journal
FEBS Lett 580:1625-30 (2006)
DOI:10.1016/j.febslet.2006.02.008
Reference
  Authors
Saikia S, Parker EJ, Koulman A, Scott B
  Title
Defining paxilline biosynthesis in Penicillium paxilli: functional characterization of two cytochrome P450 monooxygenases.
  Journal
J Biol Chem 282:16829-37 (2007)
DOI:10.1074/jbc.M701626200
Reference
  Authors
Nicholson MJ, Koulman A, Monahan BJ, Pritchard BL, Payne GA, Scott B
  Title
Identification of two aflatrem biosynthesis gene loci in Aspergillus flavus and metabolic engineering of Penicillium paxilli to elucidate their function.
  Journal
Appl Environ Microbiol 75:7469-81 (2009)
DOI:10.1128/AEM.02146-08
Reference
  Authors
Saikia S, Takemoto D, Tapper BA, Lane GA, Fraser K, Scott B
  Title
Functional analysis of an indole-diterpene gene cluster for lolitrem B biosynthesis in the grass endosymbiont Epichloe festucae.
  Journal
FEBS Lett 586:2563-9 (2012)
DOI:10.1016/j.febslet.2012.06.035
Reference
  Authors
Motoyama T, Hayashi T, Hirota H, Ueki M, Osada H
  Title
Terpendole E, a kinesin Eg5 inhibitor, is a key biosynthetic intermediate of indole-diterpenes in the producing fungus Chaunopycnis alba.
  Journal
Chem Biol 19:1611-9 (2012)
DOI:10.1016/j.chembiol.2012.10.010
Related
pathway
map00400  Phenylalanine, tyrosine and tryptophan biosynthesis
map00900  Terpenoid backbone biosynthesis
KO pathway
ko00403   
LinkDB

DBGET integrated database retrieval system