ENTRY       osa00402                    Pathway
NAME        Benzoxazinoid biosynthesis - Oryza sativa japonica (Japanese rice) (RefSeq)
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 osa00402  Benzoxazinoid biosynthesis
ORGANISM    Oryza sativa japonica (Japanese rice) (RefSeq) [GN:osa]
GENE        4334427  indole-3-glycerol phosphate lyase, chloroplastic [KO:K13222] [EC:4.1.2.8]
            9268807  tryptophan synthase alpha chain [KO:K13222] [EC:4.1.2.8]
            9270552  indole-3-glycerol phosphate lyase, chloroplastic [KO:K13222] [EC:4.1.2.8]
            4350429  DIMBOA UDP-glucosyltransferase BX8 [KO:K13227] [EC:2.4.1.202]
            4342809  DIMBOA UDP-glucosyltransferase BX8 [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   PMID:11106389
  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   PMID:11556781
  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   PMID:16260753
  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   PMID:12620350
  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   PMID:11851909
  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   PMID:16666853
  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   PMID:18192444
  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   PMID:19577780
  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
REL_PATHWAY osa00400  Phenylalanine, tyrosine and tryptophan biosynthesis
KO_PATHWAY  ko00402
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