Staff Publications

Staff Publications

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    'Staff publications' is the digital repository of Wageningen University & Research

    'Staff publications' contains references to publications authored by Wageningen University staff from 1976 onward.

    Publications authored by the staff of the Research Institutes are available from 1995 onwards.

    Full text documents are added when available. The database is updated daily and currently holds about 240,000 items, of which 72,000 in open access.

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Record number 543699
Title Kauniolide synthase is a P450 with unusual hydroxylation and cyclization-elimination activity
Author(s) Liu, Qing; Beyraghdar Kashkooli, Arman; Manzano, David; Pateraki, Irini; Richard, Lea; Kolkman, Pim; Lucas, Maria Fátima; Guallar, Victor; Vos, Ric C.H. de; Franssen, Maurice C.R.; Krol, Alexander van der; Bouwmeester, Harro
Source Nature Communications 9 (2018)1. - ISSN 2041-1723
DOI https://doi.org/10.1038/s41467-018-06565-8
Department(s) BIOS Applied Metabolic Systems
Laboratory of Plant Physiology
VLAG
Organic Chemistry
Publication type Refereed Article in a scientific journal
Publication year 2018
Abstract

Guaianolides are an important class of sesquiterpene lactones with unique biological and pharmaceutical properties. They have been postulated to be derived from germacranolides, but for years no progress has been made in the elucidation of their biosynthesis that requires an unknown cyclization mechanism. Here we demonstrate the isolation and characterization of a cytochrome P450 from feverfew (Tanacetum parthenium), kauniolide synthase. Kauniolide synthase catalyses the formation of the guaianolide kauniolide from the germacranolide substrate costunolide. Unlike most cytochrome P450s, kauniolide synthase combines stereoselective hydroxylation of costunolide at the C3 position, with water elimination, cyclization and regioselective deprotonation. This unique mechanism of action is supported by in silico modelling and docking experiments. The full kauniolide biosynthesis pathway is reconstructed in the heterologous hosts Nicotiana benthamiana and yeast, paving the way for biotechnological production of guaianolide-type sesquiterpene lactones.

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