Cytochrome P450 monooxygenase-mediated tailoring of triterpenoids and steroids in plants

Publikation: Beitrag in FachzeitschriftÜbersichtsarbeitForschungPeer-Review

Autoren

  • Karan Malhotra
  • Jakob Franke
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Details

OriginalspracheEnglisch
Seiten (von - bis)1289-1310
Seitenumfang22
FachzeitschriftBeilstein Journal of Organic Chemistry
Jahrgang18
PublikationsstatusVeröffentlicht - 21 Sept. 2022

Abstract

The cytochrome P450 monooxygenase (CYP) superfamily comprises hemethiolate enzymes that perform remarkable regio- and stereospecific oxidative chemistry. As such, CYPs are key agents for the structural and functional tailoring of triterpenoids, one of the largest classes of plant natural products with widespread applications in pharmaceuticals, food, cosmetics, and agricultural industries. In this review, we provide a full overview of 149 functionally characterised CYPs involved in the biosynthesis of triterpenoids and steroids in primary as well as in specialised metabolism. We describe the phylogenetic distribution of triterpenoid- and steroid-modifying CYPs across the plant CYPome, present a structure-based summary of their reactions, and highlight recent examples of particular interest to the field. Our review therefore provides a comprehensive up-to-date picture of CYPs involved in the biosynthesis of triterpenoids and steroids in plants as a starting point for future research.

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Cytochrome P450 monooxygenase-mediated tailoring of triterpenoids and steroids in plants. / Malhotra, Karan; Franke, Jakob.
in: Beilstein Journal of Organic Chemistry, Jahrgang 18, 21.09.2022, S. 1289-1310.

Publikation: Beitrag in FachzeitschriftÜbersichtsarbeitForschungPeer-Review

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abstract = "The cytochrome P450 monooxygenase (CYP) superfamily comprises hemethiolate enzymes that perform remarkable regio- and stereospecific oxidative chemistry. As such, CYPs are key agents for the structural and functional tailoring of triterpenoids, one of the largest classes of plant natural products with widespread applications in pharmaceuticals, food, cosmetics, and agricultural industries. In this review, we provide a full overview of 149 functionally characterised CYPs involved in the biosynthesis of triterpenoids and steroids in primary as well as in specialised metabolism. We describe the phylogenetic distribution of triterpenoid- and steroid-modifying CYPs across the plant CYPome, present a structure-based summary of their reactions, and highlight recent examples of particular interest to the field. Our review therefore provides a comprehensive up-to-date picture of CYPs involved in the biosynthesis of triterpenoids and steroids in plants as a starting point for future research.",
keywords = "biosynthesis, CYPs, cytochrome P450 monooxygenases, plants, steroid, sterol, triterpene, triterpenoid",
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note = "Funding Information: We gratefully acknowledge financial support by the Emmy Noether programme of the Deutsche Forschungsgemeinschaft (FR 3720/3-1) and the SMART BIOTECS alliance between the Technische Universit{\"a}t Braunschweig and the Leibniz Universit{\"a}t Hannover, supported by the Ministry of Science and Culture (MWK) of Lower Saxony. ",
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Download

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N1 - Funding Information: We gratefully acknowledge financial support by the Emmy Noether programme of the Deutsche Forschungsgemeinschaft (FR 3720/3-1) and the SMART BIOTECS alliance between the Technische Universität Braunschweig and the Leibniz Universität Hannover, supported by the Ministry of Science and Culture (MWK) of Lower Saxony.

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N2 - The cytochrome P450 monooxygenase (CYP) superfamily comprises hemethiolate enzymes that perform remarkable regio- and stereospecific oxidative chemistry. As such, CYPs are key agents for the structural and functional tailoring of triterpenoids, one of the largest classes of plant natural products with widespread applications in pharmaceuticals, food, cosmetics, and agricultural industries. In this review, we provide a full overview of 149 functionally characterised CYPs involved in the biosynthesis of triterpenoids and steroids in primary as well as in specialised metabolism. We describe the phylogenetic distribution of triterpenoid- and steroid-modifying CYPs across the plant CYPome, present a structure-based summary of their reactions, and highlight recent examples of particular interest to the field. Our review therefore provides a comprehensive up-to-date picture of CYPs involved in the biosynthesis of triterpenoids and steroids in plants as a starting point for future research.

AB - The cytochrome P450 monooxygenase (CYP) superfamily comprises hemethiolate enzymes that perform remarkable regio- and stereospecific oxidative chemistry. As such, CYPs are key agents for the structural and functional tailoring of triterpenoids, one of the largest classes of plant natural products with widespread applications in pharmaceuticals, food, cosmetics, and agricultural industries. In this review, we provide a full overview of 149 functionally characterised CYPs involved in the biosynthesis of triterpenoids and steroids in primary as well as in specialised metabolism. We describe the phylogenetic distribution of triterpenoid- and steroid-modifying CYPs across the plant CYPome, present a structure-based summary of their reactions, and highlight recent examples of particular interest to the field. Our review therefore provides a comprehensive up-to-date picture of CYPs involved in the biosynthesis of triterpenoids and steroids in plants as a starting point for future research.

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KW - steroid

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