KEGG   PATHWAY: taes00402
Entry
taes00402                   Pathway                                
Name
Benzoxazinoid biosynthesis - Triticum aestivum (bread wheat)
Description
Benzoxazinoids (hydroxamic acids) are plant secondary metabolites that serve as important factors for host resistance against microbial pathogens and insects and for allelopathic effects. They are found in grass family and some eudicot families. The predominant benzoxazinoids are DIBOA and its 7-methoxy derivative DIMBOA, which are stored as glucosides in vacuoles. In maize, benzoxazinoid biosynthesis branches off from tryptophan biosynthesis at indole-3-glycerol phosphate, which is converted to indole by indole-3-glycerol phosphate lyase, BX1. Subsequently four cytochrome P450 monooxygenases (BX2-BX5) catalyze the introduction of four oxygen atoms into the indole moiety, yielding DIBOA. After glucosylation by UDP-glucosyltransferase (BX8/BX9), the glucoside is further modified by hydroxylation and O-methylation at C-7 to form DIMBOA-glucoside.
Class
Metabolism; Biosynthesis of other secondary metabolites
Pathway map
taes00402  Benzoxazinoid biosynthesis
taes00402

Organism
Triticum aestivum (bread wheat) [GN:taes]
Gene
123076902  indole-3-glycerol phosphate lyase, chloroplastic-like [KO:K13222] [EC:4.1.2.8]
606350  indole-3-glycerol phosphate lyase, chloroplastic [KO:K13222] [EC:4.1.2.8]
123113684  tryptophan synthase alpha chain-like [KO:K13222] [EC:4.1.2.8]
123113689  tryptophan synthase alpha chain-like [KO:K13222] [EC:4.1.2.8]
123113690  tryptophan synthase alpha chain-like [KO:K13222] [EC:4.1.2.8]
543409  indole-3-glycerol phosphate lyase, chloroplastic [KO:K13222] [EC:4.1.2.8]
123064487  indole-3-glycerol phosphate lyase, chloroplastic-like [KO:K13222] [EC:4.1.2.8]
123117220  tryptophan synthase alpha chain-like [KO:K13222] [EC:4.1.2.8]
123100031  indole-3-glycerol phosphate lyase, chloroplastic-like [KO:K13222] [EC:4.1.2.8]
123101657  tryptophan synthase alpha chain-like [KO:K13222] [EC:4.1.2.8]
123121015  tryptophan synthase alpha chain-like [KO:K13222] [EC:4.1.2.8]
123105414  tryptophan synthase alpha chain-like isoform X1 [KO:K13222] [EC:4.1.2.8]
123105418  tryptophan synthase alpha chain-like [KO:K13222] [EC:4.1.2.8]
123123211  tryptophan synthase alpha chain-like isoform X1 [KO:K13222] [EC:4.1.2.8]
123123214  tryptophan synthase alpha chain-like [KO:K13222] [EC:4.1.2.8]
123108041  tryptophan synthase alpha chain-like [KO:K13222] [EC:4.1.2.8]
123125768  tryptophan synthase alpha chain-like [KO:K13222] [EC:4.1.2.8]
123057652  indole-3-glycerol phosphate lyase, chloroplastic-like [KO:K13222] [EC:4.1.2.8]
123097902  indole-2-monooxygenase-like [KO:K13223] [EC:1.14.14.153]
123085450  indole-2-monooxygenase-like [KO:K13223] [EC:1.14.14.153]
123092596  indole-2-monooxygenase-like [KO:K13223] [EC:1.14.14.153]
123191890  indolin-2-one monooxygenase-like [KO:K13224] [EC:1.14.14.157]
123119086  indolin-2-one monooxygenase-like [KO:K13224] [EC:1.14.14.157]
123101970  indolin-2-one monooxygenase-like [KO:K13224] [EC:1.14.14.157]
123054595  indolin-2-one monooxygenase-like [KO:K13224] [EC:1.14.14.157]
123110087  indolin-2-one monooxygenase-like [KO:K13224] [EC:1.14.14.157]
123119085  3-hydroxyindolin-2-one monooxygenase-like [KO:K13225] [EC:1.14.14.109]
123101969  3-hydroxyindolin-2-one monooxygenase-like [KO:K13225] [EC:1.14.14.109]
123110086  3-hydroxyindolin-2-one monooxygenase-like [KO:K13225] [EC:1.14.14.109]
123119084  cytochrome P450 71C3-like [KO:K13226] [EC:1.14.14.110]
123101968  cytochrome P450 71C3-like [KO:K13226] [EC:1.14.14.110]
123110085  cytochrome P450 71C3-like [KO:K13226] [EC:1.14.14.110]
123110235  cytochrome P450 71C3-like [KO:K13226] [EC:1.14.14.110]
123110236  cytochrome P450 71C3-like [KO:K13226] [EC:1.14.14.110]
123147887  DIMBOA UDP-glucosyltransferase BX8-like [KO:K13227] [EC:2.4.1.202]
123167683  DIMBOA UDP-glucosyltransferase BX8-like [KO:K13227] [EC:2.4.1.202]
123150283  DIMBOA UDP-glucosyltransferase BX9-like [KO:K13227] [EC:2.4.1.202]
123150314  DIMBOA UDP-glucosyltransferase BX9-like [KO:K13227] [EC:2.4.1.202]
123172831  DIMBOA UDP-glucosyltransferase BX8-like [KO:K13227] [EC:2.4.1.202]
100682422  DIMBOA UDP-glucosyltransferase BX8 [KO:K13227] [EC:2.4.1.202]
123159126  DIMBOA UDP-glucosyltransferase BX8-like [KO:K13227] [EC:2.4.1.202]
123160005  DIMBOA UDP-glucosyltransferase BX8-like [KO:K13227] [EC:2.4.1.202]
Compound
C00463  Indole
C03506  Indoleglycerol phosphate
C04831  DIMBOA-glucoside
C11130  3-Hydroxyindolin-2-one
C12312  Indolin-2-one
C15769  HBOA
C15770  DIBOA
C15772  DIBOA-glucoside
C18062  TRIBOA-glucoside
Reference
  Authors
Frey M, Stettner C, Pare PW, Schmelz EA, Tumlinson JH, Gierl A.
  Title
An herbivore elicitor activates the gene for indole emission in maize.
  Journal
Proc Natl Acad Sci U S A 97:14801-6 (2000)
DOI:10.1073/pnas.260499897
Reference
  Authors
Gierl A, Frey M.
  Title
Evolution of benzoxazinone biosynthesis and indole production in maize.
  Journal
Planta 213:493-8 (2001)
DOI:10.1007/s004250100594
Reference
  Authors
Nomura T, Ishihara A, Yanagita RC, Endo TR, Iwamura H.
  Title
Three genomes differentially contribute to the biosynthesis of benzoxazinones in hexaploid wheat.
  Journal
Proc Natl Acad Sci U S A 102:16490-5 (2005)
DOI:10.1073/pnas.0505156102
Reference
PMID:9235894
  Authors
Frey M, Chomet P, Glawischnig E, Stettner C, Grun S, Winklmair A, Eisenreich W, Bacher A, Meeley RB, Briggs SP, Simcox K, Gierl A.
  Title
Analysis of a chemical plant defense mechanism in grasses.
  Journal
Science 277:696-9 (1997)
DOI:10.1126/science.277.5326.696
Reference
  Authors
Frey M, Huber K, Park WJ, Sicker D, Lindberg P, Meeley RB, Simmons CR, Yalpani N, Gierl A.
  Title
A 2-oxoglutarate-dependent dioxygenase is integrated in DIMBOA-biosynthesis.
  Journal
Phytochemistry 62:371-6 (2003)
DOI:10.1016/S0031-9422(02)00556-3
Reference
  Authors
von Rad U, Huttl R, Lottspeich F, Gierl A, Frey M.
  Title
Two glucosyltransferases are involved in detoxification of benzoxazinoids in maize.
  Journal
Plant J 28:633-42 (2001)
DOI:10.1046/j.1365-313x.2001.01161.x
Reference
  Authors
Bailey BA, Larson RL
  Title
Hydroxamic Acid glucosyltransferases from maize seedlings.
  Journal
Plant Physiol 90:1071-6 (1989)
DOI:10.1104/pp.90.3.1071
Reference
  Authors
Jonczyk R, Schmidt H, Osterrieder A, Fiesselmann A, Schullehner K, Haslbeck M, Sicker D, Hofmann D, Yalpani N, Simmons C, Frey M, Gierl A
  Title
Elucidation of the final reactions of DIMBOA-glucoside biosynthesis in maize: characterization of Bx6 and Bx7.
  Journal
Plant Physiol 146:1053-63 (2008)
DOI:10.1104/pp.107.111237
Reference
  Authors
Frey M, Schullehner K, Dick R, Fiesselmann A, Gierl A
  Title
Benzoxazinoid biosynthesis, a model for evolution of secondary metabolic pathways in plants.
  Journal
Phytochemistry 70:1645-51 (2009)
DOI:10.1016/j.phytochem.2009.05.012
Related
pathway
taes00400  Phenylalanine, tyrosine and tryptophan biosynthesis
KO pathway
ko00402   
LinkDB

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