KEGG   PATHWAY: rn00402
Entry
rn00402                     Pathway                                
Name
Benzoxazinoid biosynthesis
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
rn00402  Benzoxazinoid biosynthesis
rn00402

Reaction
R02340  (1S,2R)-1-C-(indol-3-yl)glycerol 3-phosphate D-glyceraldehyde-3-phosphate-lyase
R07403  indole,[reduced NADPH---hemoprotein reductase]:oxygen oxidoreductase (2-hydroxylating)
R07421  indolin-2-one,[reduced NADPH---hemoprotein reductase]:oxygen oxidoreductase (3-hydroxylating)
R07422  3-hydroxyindolin-2-one,[reduced NADPH---hemoprotein reductase]:oxygen oxidoreductase (2-hydroxy-2H-1,4-benzoxazin-3(4H)-one-forming)
R07423  2-hydroxy-2H-1,4-benzoxazin-3(4H)-one,[reduced NADPH---hemoprotein reductase]:oxygen oxidoreductase (N-hydroxylating)
R07426  UDP-glucose:DIBOA 2-D-glucosyltransferase
R08972  (2R)-4-hydroxy-3-oxo-3,4-dihydro-2H-1,4-benzoxazin-2-yl beta-D-glucopyranoside:oxygen oxidoreductase (7-hydroxylating)
R08973  S-adenosyl-L-methionine:TRIBOA-glucoside 7-O-methyltransferase
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
Related
pathway
rn00400  Phenylalanine, tyrosine and tryptophan biosynthesis
KO pathway
ko00402   

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