An unexpected diterpene cyclase from rice: Functional identification of a stemodene synthase

Dana Morrone; Yinghua Jin; Meimei Xu; Suh Yeon Choi; Robert M. Coates; Reuben J. Peters

doi:10.1016/j.abb.2005.09.001

An unexpected diterpene cyclase from rice: Functional identification of a stemodene synthase

Dana Morrone, Yinghua Jin, Meimei Xu, Suh Yeon Choi, Robert M. Coates, Reuben J. Peters

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41 Scopus citations

Abstract

We have cloned a novel diterpene synthase (OsKSL11) from rice that produces stemod-13(17)-ene from syn-copalyl diphosphate. Notably, this gene sequence was not predicted from the extensive sequence information available for rice, nor, despite extensive phytochemical investigations, has this diterpene or any derived natural product previously been reported in rice plants. OsKSL11 represents the first identified stemodene synthase, which catalyzes the committed step in biosynthesis of the stemodane family of diterpenoid natural products, some of which possess antiviral activity. In addition, OsKSL11 is highly homologous to the mechanistically similar stemarene synthase recently identified from rice, making this pair of diterpene cyclases an excellent model system for investigating the enzymatic determinants for differential product outcome. The unexpected nature of this cyclase and its product parallels recent observations of previously unrecognized natural products metabolism in Arabidopsis thaliana, suggesting that many, if not all, plant species will prove to have extensive biosynthetic capacity.

Original language	English (US)
Pages (from-to)	133-140
Number of pages	8
Journal	Archives of Biochemistry and Biophysics
Volume	448
Issue number	1-2
DOIs	https://doi.org/10.1016/j.abb.2005.09.001
State	Published - Apr 15 2006
Externally published	Yes

Bibliographical note

Funding Information:
We thank Dr. James D. White (Oregon State University) for generously providing a mixture of synthetic (±)-exo- and endo-stemodene. This work was supported by USDA-NRI Grant 2005-35318-15477 (to R.J.P.) and NIH Grant GM13956 (to R.M.C.), as well as fellowship support from Iowa State University (to D.M.) and the University of Illinois (to Y.J.).

Keywords

Biosynthesis
Functional genomics
Labdane-related diterpenoids
Natural products
Terpene synthases

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title = "An unexpected diterpene cyclase from rice: Functional identification of a stemodene synthase",

abstract = "We have cloned a novel diterpene synthase (OsKSL11) from rice that produces stemod-13(17)-ene from syn-copalyl diphosphate. Notably, this gene sequence was not predicted from the extensive sequence information available for rice, nor, despite extensive phytochemical investigations, has this diterpene or any derived natural product previously been reported in rice plants. OsKSL11 represents the first identified stemodene synthase, which catalyzes the committed step in biosynthesis of the stemodane family of diterpenoid natural products, some of which possess antiviral activity. In addition, OsKSL11 is highly homologous to the mechanistically similar stemarene synthase recently identified from rice, making this pair of diterpene cyclases an excellent model system for investigating the enzymatic determinants for differential product outcome. The unexpected nature of this cyclase and its product parallels recent observations of previously unrecognized natural products metabolism in Arabidopsis thaliana, suggesting that many, if not all, plant species will prove to have extensive biosynthetic capacity.",

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note = "Funding Information: We thank Dr. James D. White (Oregon State University) for generously providing a mixture of synthetic (±)-exo- and endo-stemodene. This work was supported by USDA-NRI Grant 2005-35318-15477 (to R.J.P.) and NIH Grant GM13956 (to R.M.C.), as well as fellowship support from Iowa State University (to D.M.) and the University of Illinois (to Y.J.).",

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An unexpected diterpene cyclase from rice: Functional identification of a stemodene synthase

Abstract

Bibliographical note

Keywords

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