Stemar‐13‐ene synthase, a diterpene cyclase involved in the biosynthesis of the phytoalexin oryzalexin S in rice

Nemoto, Tadahiro; Cho, Eun-Min; Okada, Atsushi; Okada, Kazunori; Otomo, Kazuko; Kanno, Yuka; Toyomasu, Tomonobu; Mitsuhashi, Wataru; Sassa, Takeshi; Minami, Eiichi; Shibuya, Naoto; Nishiyama, Makoto; Nojiri, Hideaki; Yamane, Hisakazu

doi:10.1016/j.febslet.2004.07.002

Cited by 76 publications

(80 citation statements)

References 31 publications

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“…The YDTAW motif near the N-terminus, the function of which is unknown, has been extensively found in diterpene cyclases in plants. [19][20][21][22][23] This YDTAW motif, however, has not been found in triterpene or sesquiterpene cyclases. PhCPS/KS contains five AsnXaa-Ser/Thr motifs, which might be a site for Nglycosylation of the protein.…”

Section: Formation Of a Ga Skeleton Inmentioning

confidence: 99%

Biochemical and Molecular Analyses of Gibberellin Biosynthesis in Fungi

Kawaide

2006

Bioscience, Biotechnology, and Biochemistry

123

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Section: Formation Of a Ga Skeleton Inmentioning

confidence: 99%

Biochemical and Molecular Analyses of Gibberellin Biosynthesis in Fungi

Kawaide

2006

Bioscience, Biotechnology, and Biochemistry

123

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“…2A). [20][21][22][23] The transcript levels of all of these genes increased markedly after UV treatment in rice leaves and after elicitor treatment in cultured rice cells, both of which induce phytoalexin biosynthesis. Thus these genes are likely to be involved in rice diterpene phytoalexin biosynthesis.…”

Section: Labdane-related Diterpene Cyclase Gene Family In Ricementioning

confidence: 99%

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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“…Hence, the upstream enzymes, ent-CPP synthase (CPS), KS, and kaurene oxidase (KO)/CYP701, can be diverted to alternative labdane-related diterpenoid biosynthesis. Many examples of CPS and KS-like (KSL) diterpene synthases that operate in more specialized metabolism are known Nemoto et al, 2004;Otomo et al, 2004aOtomo et al, , 2004bPrisic et al, 2004;Wilderman et al, 2004;Xu et al, 2004Xu et al, , 2007Harris et al, 2005;Kanno et al, 2006;Morrone et al, 2006;Gao et al, 2009;Toyomasu et al, 2009;Falara et al, 2010). By contrast, no KO/ CYP701 family member has been shown to act as anything other than a KO-i.e.…”

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CYP701A8: A Rice ent-Kaurene Oxidase Paralog Diverted to More Specialized Diterpenoid Metabolism

et al. 2012

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All higher plants contain an ent-kaurene oxidase (KO), as such a cytochrome P450 (CYP) 701 family member is required for gibberellin (GA) phytohormone biosynthesis. While gene expansion and functional diversification of GA-biosynthesis-derived diterpene synthases into more specialized metabolism has been demonstrated, no functionally divergent KO/CYP701 homologs have been previously identified. Rice (Oryza sativa) contains five CYP701A subfamily members in its genome, despite the fact that only one (OsKO2/CYP701A6) is required for GA biosynthesis. Here we demonstrate that one of the other rice CYP701A subfamily members, OsKOL4/CYP701A8, does not catalyze the prototypical conversion of the ent-kaurene C4a-methyl to a carboxylic acid, but instead carries out hydroxylation at the nearby C3a position in a number of related diterpenes. In particular, under conditions where OsKO2 catalyzes the expected conversion of ent-kaurene to ent-kaurenoic acid required for GA biosynthesis, OsKOL4 instead efficiently reacts with ent-sandaracopimaradiene and ent-cassadiene to produce the corresponding C3a-hydroxylated diterpenoids. These compounds are expected intermediates in biosynthesis of the oryzalexin and phytocassane families of rice antifungal phytoalexins, respectively, and can be detected in rice plants under the appropriate conditions. Thus, it appears that OsKOL4 plays a role in the more specialized diterpenoid metabolism of rice, and our results provide evidence for divergence of a KO/CYP701 family member from GA biosynthesis. This further expands the range of enzymes recruited from the ancestral GA primary pathway to the more complex and specialized labdane-related diterpenoid metabolic network found in rice.

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Stemar‐13‐ene synthase, a diterpene cyclase involved in the biosynthesis of the phytoalexin oryzalexin S in rice

Cited by 76 publications

References 31 publications

Biochemical and Molecular Analyses of Gibberellin Biosynthesis in Fungi

Biochemical and Molecular Analyses of Gibberellin Biosynthesis in Fungi

Recent Advances Regarding Diterpene Cyclase Genes in Higher Plants and Fungi

CYP701A8: A Rice ent-Kaurene Oxidase Paralog Diverted to More Specialized Diterpenoid Metabolism

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