Biosynthesis of tovarol and other sesquiterpenoids in Thapsia laciniata Rouy

Trine Bundgaard Andersen; Silas Anselm Rasmussen; Søren Brøgger Christensen; Henrik Toft Simonsen

doi:10.1016/j.phytochem.2018.10.027

Biosynthesis of tovarol and other sesquiterpenoids in Thapsia laciniata Rouy

Trine Bundgaard Andersen, Silas Anselm Rasmussen, Søren Brøgger Christensen, Henrik Toft Simonsen

Section for Crop Sciences

5 Citations (Scopus)

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,
TlTPS820, TlTPS509 and TlTPS18983. TlTPS18983 is a multi-product enzyme with farnesene as the major
product, while TlTPS509 produces guaiol and bulnesol along with other major and several minor unknown
products. TlTPS820 is orthologous to TgTPS2 from Thapsia garganica L. and is an epikunzeaol synthase.
TgCYP76AE2 from Thapsia garganica performs a triple hydroxylation of epikunzeaol at C-12 to make dihydrocostunolide.
It was therefore investigated if the cytochrome P450, TlCYP76AE4 was able to use epikunzeaol
as a substrate. It was found that TlCYP76AE4 hydroxylates epikunzeaol at C-8 to yield tovarol instead of dihydrocostunolide.

Original language	English
Journal	Phytochemistry
Volume	157
Issue number	https://doi.org/10.1016/j.phytochem.2018.10.027
Pages (from-to)	168-174
Number of pages	15
ISSN	0031-9422
DOIs	https://doi.org/10.1016/j.phytochem.2018.10.027
Publication status	Published - Jan 2019

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10.1016/j.phytochem.2018.10.027

Cite this

@article{7bd9dff6d80f4e378f3181be3dadd922,

title = "Biosynthesis of tovarol and other sesquiterpenoids in Thapsia laciniata Rouy",

abstract = "The genus Thapsia produces a wide variety of sesquiterpenoids. The Mediterranean plant Thapsia laciniata Rouyis known to have a product profile that differs from several other species in the genus. Thus, the biosynthesis ofsesquiterpenoids in Thapsia laciniata Rouy was investigated. Here we describe three terpene synthases,TlTPS820, TlTPS509 and TlTPS18983. TlTPS18983 is a multi-product enzyme with farnesene as the majorproduct, while TlTPS509 produces guaiol and bulnesol along with other major and several minor unknownproducts. TlTPS820 is orthologous to TgTPS2 from Thapsia garganica L. and is an epikunzeaol synthase.TgCYP76AE2 from Thapsia garganica performs a triple hydroxylation of epikunzeaol at C-12 to make dihydrocostunolide.It was therefore investigated if the cytochrome P450, TlCYP76AE4 was able to use epikunzeaolas a substrate. It was found that TlCYP76AE4 hydroxylates epikunzeaol at C-8 to yield tovarol instead of dihydrocostunolide.",

author = "Andersen, {Trine Bundgaard} and Rasmussen, {Silas Anselm} and Christensen, {S{\o}ren Br{\o}gger} and Simonsen, {Henrik Toft}",

year = "2019",

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language = "English",

volume = "157",

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T1 - Biosynthesis of tovarol and other sesquiterpenoids in Thapsia laciniata Rouy

AU - Andersen, Trine Bundgaard

AU - Rasmussen, Silas Anselm

AU - Christensen, Søren Brøgger

AU - Simonsen, Henrik Toft

PY - 2019/1

Y1 - 2019/1

N2 - The genus Thapsia produces a wide variety of sesquiterpenoids. The Mediterranean plant Thapsia laciniata Rouyis known to have a product profile that differs from several other species in the genus. Thus, the biosynthesis ofsesquiterpenoids in Thapsia laciniata Rouy was investigated. Here we describe three terpene synthases,TlTPS820, TlTPS509 and TlTPS18983. TlTPS18983 is a multi-product enzyme with farnesene as the majorproduct, while TlTPS509 produces guaiol and bulnesol along with other major and several minor unknownproducts. TlTPS820 is orthologous to TgTPS2 from Thapsia garganica L. and is an epikunzeaol synthase.TgCYP76AE2 from Thapsia garganica performs a triple hydroxylation of epikunzeaol at C-12 to make dihydrocostunolide.It was therefore investigated if the cytochrome P450, TlCYP76AE4 was able to use epikunzeaolas a substrate. It was found that TlCYP76AE4 hydroxylates epikunzeaol at C-8 to yield tovarol instead of dihydrocostunolide.

AB - The genus Thapsia produces a wide variety of sesquiterpenoids. The Mediterranean plant Thapsia laciniata Rouyis known to have a product profile that differs from several other species in the genus. Thus, the biosynthesis ofsesquiterpenoids in Thapsia laciniata Rouy was investigated. Here we describe three terpene synthases,TlTPS820, TlTPS509 and TlTPS18983. TlTPS18983 is a multi-product enzyme with farnesene as the majorproduct, while TlTPS509 produces guaiol and bulnesol along with other major and several minor unknownproducts. TlTPS820 is orthologous to TgTPS2 from Thapsia garganica L. and is an epikunzeaol synthase.TgCYP76AE2 from Thapsia garganica performs a triple hydroxylation of epikunzeaol at C-12 to make dihydrocostunolide.It was therefore investigated if the cytochrome P450, TlCYP76AE4 was able to use epikunzeaolas a substrate. It was found that TlCYP76AE4 hydroxylates epikunzeaol at C-8 to yield tovarol instead of dihydrocostunolide.

U2 - 10.1016/j.phytochem.2018.10.027

DO - 10.1016/j.phytochem.2018.10.027

M3 - Journal article

C2 - 30412824

SN - 0031-9422

VL - 157

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JO - Phytochemistry

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