Momilactone biosynthesis (Oryza sativa)

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1-20Legend3β-Hydroxy-9β-pimara-7,15-diene-19,6β-olideLOC_Os04g09900.1Syn-copalyl Diphosphate9-beta-primara-7,15-dieneUpregulation of gene expressionLOC_Os04g09920LOC_Os04g54474 (OsTGAP1)LOC_Os04g10060.1Geranylgeranyl diphosphate biosynthesis II (plastidic)Momilactone BLOC_OS04G10010.1Momilactone AGeranylgeranyl DiphosphateLOC_Os04g10160Oryzalexin S biosynthesisCatalyst reactions


Description

Phytoalexins Momilactone A and B accumulate in rice husks. Both compounds act in multiple ways such as (1) growth inhibitors involved in seed dormancy, (2) play an important role in the rice plant defense system against pathogens and insects and (3) contribute to allelopathy where they inhibit the growth of weeds. They are also known to be induced by the jasmonic acid plant growth hormone.

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Bibliography

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  1. Wang Q, Hillwig ML, Peters RJ; ''CYP99A3: functional identification of a diterpene oxidase from the momilactone biosynthetic gene cluster in rice.''; Plant J, 2011 PubMed Europe PMC Scholia
  2. Mohan RS, Yee NK, Coates RM, Ren YY, Stamenkovic P, Mendez I, West CA; ''Biosynthesis of cyclic diterpene hydrocarbons in rice cell suspensions: conversion of 9,10-syn-labda-8(17),13-dienyl diphosphate to 9beta-pimara-7,15-diene and stemar-13-ene.''; Arch Biochem Biophys, 1996 PubMed Europe PMC Scholia
  3. Shimura K, Okada A, Okada K, Jikumaru Y, Ko KW, Toyomasu T, Sassa T, Hasegawa M, Kodama O, Shibuya N, Koga J, Nojiri H, Yamane H; ''Identification of a biosynthetic gene cluster in rice for momilactones.''; J Biol Chem, 2007 PubMed Europe PMC Scholia
  4. Lee SC, Chung IM, Jin YJ, Song YS, Seo SY, Park BS, Cho KH, Yoo KS, Kim TH, Yee SB, Bae YS, Yoo YH; ''Momilactone B, an allelochemical of rice hulls, induces apoptosis on human lymphoma cells (Jurkat) in a micromolar concentration.''; Nutr Cancer, 2008 PubMed Europe PMC Scholia
  5. Kim SJ, Park HR, Park E, Lee SC; ''Cytotoxic and antitumor activity of momilactone B from rice hulls.''; J Agric Food Chem, 2007 PubMed Europe PMC Scholia
  6. Wilderman PR, Xu M, Jin Y, Coates RM, Peters RJ; ''Identification of syn-pimara-7,15-diene synthase reveals functional clustering of terpene synthases involved in rice phytoalexin/allelochemical biosynthesis.''; Plant Physiol, 2004 PubMed Europe PMC Scholia
  7. Atawong A, Hasegawa M, Kodama O; ''Biosynthesis of rice phytoalexin: enzymatic conversion of 3beta-hydroxy-9beta-pimara-7,15-dien-19,6beta-olide to momilactone A.''; Biosci Biotechnol Biochem, 2002 PubMed Europe PMC Scholia
  8. Toyomasu T, Kagahara T, Okada K, Koga J, Hasegawa M, Mitsuhashi W, Sassa T, Yamane H; ''Diterpene phytoalexins are biosynthesized in and exuded from the roots of rice seedlings.''; Biosci Biotechnol Biochem, 2008 PubMed Europe PMC Scholia
  9. Kato-Noguchi H; ''Convergent or parallel molecular evolution of momilactone A and B: potent allelochemicals, momilactones have been found only in rice and the moss Hypnum plumaeforme.''; J Plant Physiol, 2011 PubMed Europe PMC Scholia
  10. Okada A, Okada K, Miyamoto K, Koga J, Shibuya N, Nojiri H, Yamane H; ''OsTGAP1, a bZIP transcription factor, coordinately regulates the inductive production of diterpenoid phytoalexins in rice.''; J Biol Chem, 2009 PubMed Europe PMC Scholia
  11. Rodrigues FA, McNally DJ, Datnoff LE, Jones JB, Labbé C, Benhamou N, Menzies JG, Bélanger RR; ''Silicon enhances the accumulation of diterpenoid phytoalexins in rice: a potential mechanism for blast resistance.''; Phytopathology, 2004 PubMed Europe PMC Scholia
  12. Otomo K, Kanno Y, Motegi A, Kenmoku H, Yamane H, Mitsuhashi W, Oikawa H, Toshima H, Itoh H, Matsuoka M, Sassa T, Toyomasu T; ''Diterpene cyclases responsible for the biosynthesis of phytoalexins, momilactones A, B, and oryzalexins A-F in rice.''; Biosci Biotechnol Biochem, 2004 PubMed Europe PMC Scholia
  13. Lee JH, Cho B, Jun HJ, Seo WD, Kim DW, Cho KJ, Lee SJ; ''Momilactione B inhibits protein kinase A signaling and reduces tyrosinase-related proteins 1 and 2 expression in melanocytes.''; Biotechnol Lett, 2012 PubMed Europe PMC Scholia
  14. Kanno Y, Otomo K, Kenmoku H, Mitsuhashi W, Yamane H, Oikawa H, Toshima H, Matsuoka M, Sassa T, Toyomasu T; ''Characterization of a rice gene family encoding type-A diterpene cyclases.''; Biosci Biotechnol Biochem, 2006 PubMed Europe PMC Scholia
  15. Hasegawa M, Mitsuhara I, Seo S, Imai T, Koga J, Okada K, Yamane H, Ohashi Y; ''Phytoalexin accumulation in the interaction between rice and the blast fungus.''; Mol Plant Microbe Interact, 2010 PubMed Europe PMC Scholia
  16. Kato-Noguchi H, Ino T, Ota K; ''Secretion of momilactone A from rice roots to the rhizosphere.''; J Plant Physiol, 2008 PubMed Europe PMC Scholia
  17. Wickham KA, West CA; ''Biosynthesis of rice phytoalexins: identification of putative diterpene hydrocarbon precursors.''; Arch Biochem Biophys, 1992 PubMed Europe PMC Scholia
  18. Kato-Noguchi H, Hasegawa M, Ino T, Ota K, Kujime H; ''Contribution of momilactone A and B to rice allelopathy.''; J Plant Physiol, 2010 PubMed Europe PMC Scholia
  19. Kato-Noguchi H; ''The chemical cross talk between rice and barnyardgrass.''; Plant Signal Behav, 2011 PubMed Europe PMC Scholia
  20. Imai T, Ohashi Y, Mitsuhara I, Seo S, Toshima H, Hasegawa M; ''Identification of a degradation intermediate of the momilactone a rice phytoalexin by the rice blast fungus.''; Biosci Biotechnol Biochem, 2012 PubMed Europe PMC Scholia

History

View all...
CompareRevisionActionTimeUserComment
117419view10:44, 21 May 2021EweitzModified title
113896view20:38, 7 December 2020FinterlyAdded pathway link.
113895view20:36, 7 December 2020FinterlySmall graphical updates. Fixed legend.
71862view20:56, 18 October 2013EgonwAdded a few identifiers.
70138view20:56, 12 July 2013MaintBotupdated to 2013 schema
67488view11:08, 26 June 2013DdiglesOntology Term : 'momilactone biosynthetic pathway' added !
48987view22:52, 2 July 2012PjaiswalModified categories
48612view21:05, 6 June 2012Pjaiswaladded xref to WP2210
48603view19:52, 6 June 2012PjaiswalModified description
48602view19:38, 6 June 2012PjaiswalModified description
48590view00:57, 6 June 2012PjaiswalModified description
48589view00:51, 6 June 2012PjaiswalOntology Term : 'diterpenoid biosynthetic pathway' added !
48588view00:48, 6 June 2012PjaiswalNew pathway

External references

DataNodes

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NameTypeDatabase referenceComment
3β-Hydroxy-9β-pimara-7,15-diene-19,6β-olideMetabolite
9-beta-primara-7,15-dieneMetabolite
Catalyst reactions
Geranylgeranyl DiphosphateMetaboliteCHEBI:57533 (ChEBI)
Geranylgeranyl diphosphate biosynthesis II (plastidic)PathwayWP2211 (WikiPathways)
LOC_OS04G10010.1GeneProductLOC_OS04G10010.1 (Gramene Rice) sex determination protein tasselseed-2, putative, expressed//diterpene phytoalexin precursor biosynthetic process pathway//metabolic process//oxidoreductase activity
LOC_Os04g09900.1GeneProductLOC_Os04g09900.1 (Gramene Rice) ent-kaurene synthase, chloroplast precursor, putative, expressed//diterpene phytoalexin precursor biosynthetic process pathway//metabolic process//gibberellin metabolic process//ent-copalyl diphosphate synthase
LOC_Os04g09920GeneProductLOC_Os04g09920 (Gramene Rice) CYP99A3, cytochrome P450 monooxygenase
LOC_Os04g10060.1GeneProductLOC_Os04g10060.1 (Gramene Rice) ent-kaurene synthase, chloroplast precursor, putative, expressed//metabolic process//diterpene phytoalexin metabolic process//syn-pimara-7,15-diene synthase activity//ent-kaurene synthase
LOC_Os04g10160GeneProductLOC_Os04g10160 (Gramene Rice) cytochrome P450, putative, expressed
LOC_Os04g54474 (OsTGAP1)GeneProductLOC_Os04g54474 (Gramene Rice)
Momilactone AMetaboliteCHEBI:49191 (ChEBI)
Momilactone BMetabolite3084979 (PubChem-compound)
Oryzalexin S biosynthesisPathwayWP2210 (WikiPathways)
Syn-copalyl DiphosphateMetabolite
Upregulation of gene expression

Annotated Interactions

No annotated interactions

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