Synthesis and Absolute Configuration of (−)-Phytocassane D, a Diterpene Phytoalexin Isolated from the Rice Plant,Oryza sativa

Yajima, Arata; Mori, Kenji

doi:10.1002/1099-0690(200012)2000:24<4079::aid-ejoc4079>3.0.co;2-r

Cited by 50 publications

(24 citation statements)

References 25 publications

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“…Of the 15 phytoalexins that have been isolated from rice, 14 are polycyclic diterpenoid phytoalexins and the other is a flavonoid-type phytoalexin named sakuranetin. The diterpenoid phytoalexins have been classified into four groups according to their carbon skeletons: phytocassanes A-E (Koga et al 1995(Koga et al , 1997Yajima and Mori 2000), oryzalexins A-F (Akatsuka et al 1985;Kato et al 1993Kato et al , 1994, momilactones A and B (Kato et al 1973;Cartwright et al 1981), and oryzalexin S (Tamogami et al 1993). The antimicrobial activity of phytoalexins has been evaluated in a spore germination experiment using the blast fungus Magnaporthe grisea (Peters 2006).…”

Section: Introductionmentioning

confidence: 99%

Elicitor induced activation of the methylerythritol phosphate pathway toward phytoalexins biosynthesis in rice

et al. 2007

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Diterpenoid phytoalexins such as momilactones and phytocassanes are produced via geranylgeranyl diphosphate in suspension-cultured rice cells after treatment with a chitin elicitor. We have previously shown that the production of diterpene hydrocarbons leading to phytoalexins and the expression of related biosynthetic genes are activated in suspension-cultured rice cells upon elicitor treatment. To better understand the elicitor-induced activation of phytoalexin biosynthesis, we conducted microarray analysis using suspension-cultured rice cells collected at various times after treatment with chitin elicitor. Hierarchical cluster analysis revealed two types of early-induced expression (EIE-1, EIE-2) nodes and a late-induced expression (LIE) node that includes genes involved in phytoalexins biosynthesis. The LIE node contains genes that may be responsible for the methylerythritol phosphate (MEP) pathway, a plastidic biosynthetic pathway for isopentenyl diphosphate, an early precursor of phytoalexins. The elicitor-induced expression of these putative MEP pathway genes was confirmed by quantitative reverse-transcription PCR. 1-Deoxy-D: -xylulose 5-phosphate synthase (DXS), 1-deoxy-D: -xylulose 5-phosphate reductoisomerase (DXR), and 4-(cytidine 5'-diphospho)-2-C-methyl-D: -erythritol synthase (CMS), which catalyze the first three committed steps in the MEP pathway, were further shown to have enzymatic activities that complement the growth of E. coli mutants disrupted in the corresponding genes. Application of ketoclomazone and fosmidomycin, inhibitors of DXS and DXR, respectively, repressed the accumulation of diterpene-type phytoalexins in suspension cells treated with chitin elicitor. These results suggest that activation of the MEP pathway is required to supply sufficient terpenoid precursors for the production of phytoalexins in infected rice plants.

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Section: Introductionmentioning

confidence: 99%

Elicitor induced activation of the methylerythritol phosphate pathway toward phytoalexins biosynthesis in rice

et al. 2007

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“…1), [6][7][8][9] and phytocassanes (phytoalexin, Fig. 1) [10][11][12] have been isolated from plants. Similarly, fungal GAs, 13) aphidicolin (a specific inhibitor of DNA polymerase ), 14,15) and fusicoccin A (a diterpene glucoside that acts as a plant plasma membrane H þ -ATPase activator) 16,17) have been isolated from fungi.…”

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Recent Advances Regarding Diterpene Cyclase Genes in Higher Plants and Fungi

Toyomasu

2008

Bioscience, Biotechnology, and Biochemistry

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Cyclic diterpenoids are commonly biosynthesized from geranylgeranyl diphosphate (GGDP) through the formation of carbon skeletons by specific cyclases and subsequent chemical modifications, such as oxidation, reduction, methylation, and glucosidation. A variety of diterpenoids are produced in higher plants and fungi. Rice produces four classes of diterpene phytoalexins, phytocassanes A to E, oryzalexins A to F, oryzalexin S, and momilactones A and B. The six diterpene cyclase genes involved in the biosynthesis of these phytoalexins were identified and characterized. Fusicoccin A was produced by the phytopathogenic Phomopsis amygdali and served as a plant H þ -ATPase activator. A PaFS, encoding a fungal diterpene synthase responsible for fusicoccin biosynthesis, was isolated. The PaFS is an unusual chimeric diterpene synthase that possesses not only terpene cyclase activity (the formation of fusicoccadiene, a biosynthetic precursor of fusicoccin A), but also prenyltransferase activity (the formation of GGDP). Thus, we identified a unique multifunctional diterpene synthase family in fungi.

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“…and phytocassanes [7][8][9] which act as phytoalexins. GAs are important for many aspects of plant growth and development such as seed germination, stem elongation, flowering, and fruit development.…”

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confidence: 99%

Comparison of the Enzymatic Properties ofent-Copalyl Diphosphate Synthases in the Biosynthesis of Phytoalexins and Gibberellins in Rice

Hayashi¹,

Toyomasu²,

Hirose³

et al. 2008

Bioscience, Biotechnology, and Biochemistry

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Synthesis and Absolute Configuration of (−)-Phytocassane D, a Diterpene Phytoalexin Isolated from the Rice Plant,Oryza sativa

Cited by 50 publications

References 25 publications

Elicitor induced activation of the methylerythritol phosphate pathway toward phytoalexins biosynthesis in rice

Elicitor induced activation of the methylerythritol phosphate pathway toward phytoalexins biosynthesis in rice

Recent Advances Regarding Diterpene Cyclase Genes in Higher Plants and Fungi

Comparison of the Enzymatic Properties ofent-Copalyl Diphosphate Synthases in the Biosynthesis of Phytoalexins and Gibberellins in Rice

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