KEGG   PATHWAY: rn00403
Entry
rn00403                     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
rn00403  Indole diterpene alkaloid biosynthesis
rn00403

Module
M00661  Paspaline biosynthesis, geranylgeranyl-PP + indoleglycerol phosphate => paspaline [PATH:rn00403]
Reaction
R10349   
R10350  3-geranylgeranylindole,NADPH:oxygen oxidoreductase (10,11-epoxidizing)
R10351  emindole-SB,NADPH:oxygen oxidoreductase (14,15-epoxidizing)
R10352   
R10353   
R10356  paspaline-B,NADPH:oxygen oxidoreductase
R10357   
R10358   
R10359  13-desoxypaxilline,NADPH:oxygen oxidoreductase
R10360   
R10361   
R10362   
R10365  dimethylallyl-diphosphate:paspalinine dimethylallyltransferase
R10366  13-desoxyterpendole I,NADPH:oxygen oxidoreductase
R10367   
R10368   
R10369   
R10370  dimethylallyl-diphosphate:lolitriol dimethylallyl-O-transferase
R10371  paspaline,NADPH:oxygen oxidoreductase
R10372   
R10373  paspaline,NADPH:oxygen oxidoreductase
R10376   
R10379   
R10380  dimethylallyl-diphosphate:terpendole-I dimethylallyl-O-transferase
R10381   
R10382   
R10383   
R10384   
R10405   
R10406   
R10410   
R10566   
R10569   
R10570   
R10571   
R10692   
R10694   
Compound
C00353  Geranylgeranyl diphosphate
C03506  Indoleglycerol phosphate
C13782  Paxilline
C20525  3-Geranylgeranylindole
C20526  10,11-Epoxy-3-geranylgeranylindole
C20527  Emindole SB
C20528  Terpendole B
C20529  14,15-Epoxyemindole SB
C20530  Paspaline
C20531  13-Desoxypaxilline
C20532  20,21-Diprenylterpendole I
C20534  12-Demethyl-11,12-dehydropaspaline
C20535  beta-PC-M6
C20536  Terpendole E
C20542  13-Desoxyterpendole I
C20543  Terpendole I
C20545  Terpendole J
C20546  Terpendole C
C20548  Lolitriol
C20550  Lolitrem E
C20551  Lolitrem B
C20552  Terpendole K
C20553  Paspalicine
C20554  Paspalinine
C20555  Aflatrem
C20561  21,22-Diprenylpaxilline
C20586  Terpendole G
C20587  Paspaline B
C20593  beta-Paxitriol
C20594  20,21-Diprenylterpendole J
C20595  20,21-Diprenylterpendole C
C20596  Penitrem D
C20601  Janthitrem C
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
rn00400  Phenylalanine, tyrosine and tryptophan biosynthesis
rn00900  Terpenoid backbone biosynthesis
KO pathway
ko00403   
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