Biosynthesis of tovarol and other sesquiterpenoids in Thapsia laciniata Rouy. (January 2019)

• Record Type: Journal Article
• Authors: Andersen, Trine Bundgaard; Rasmussen, Silas Anselm; Christensen, Søren Brøgger; Simonsen, Henrik Toft
• Is Part Of: Phytochemistry. Volume 157(2019)
• Page Start: 168
• Page End: 174
• Publication Date: 2019-01
• Subjects: Thapsia laciniata -- Apiaceae -- Sesquiterpenoid -- CYP76AE4 -- Epikunzeaol -- Tovarol -- Guaiol -- Bulnesol; Botanical chemistry -- Periodicals; Biochemistry -- Periodicals; Botany -- Periodicals; Chimie végétale -- Périodiques; 572.2
• DOI: 10.1016/j.phytochem.2018.10.027
• Languages: English
• ISSNs: 0031-9422

Abstract

Abstract: The genus Thapsia produces a wide variety of sesquiterpenoids. The Mediterranean plant Thapsia laciniata Rouy is known to have a product profile that differs from several other species in the genus. Thus, the biosynthesis of sesquiterpenoids in Thapsia laciniata Rouy was investigated. Here we describe three terpene synthases, Tl TPS820, Tl TPS509 and Tl TPS18983. Tl TPS18983 is a multi-product enzyme with farnesene as the major product, while Tl TPS509 produces guaiol and bulnesol along with other major and several minor unknown products. Tl TPS820 is orthologous to Tg TPS2 from Thapsia garganica L. and is an epikunzeaol synthase. Tg CYP76AE2 from Thapsia garganica performs a triple hydroxylation of epikunzeaol at C-12 to make dihydrocostunolide. It was therefore investigated if the cytochrome P450, Tl CYP76AE4 was able to use epikunzeaol as a substrate. It was found that Tl CYP76AE4 hydroxylates epikunzeaol at C-8 to yield tovarol instead of dihydrocostunolide. Graphical abstract: The biosynthesis of sesquiterpenoids in Thapsia laciniata Rouy was investigated, and three terpene synthases was characterized. Image 1 Highlights: Three sesquiterpene synthases is characterized as one epikunzeaol and two multiple synthases. The cytochrome P450 TlCYP76AE4 hydroxylates epikunzeaol at C-8 yielding tovarol. Epikunzeaol synthase and TlCYP76AE4 is responsible for biosynthesis of tovarol in T. laciniata.