Biosynthesis of tovarol and other sesquiterpenoids in Thapsia laciniata Rouy

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

*Corresponding author for this work

Research output: Contribution to journalJournal articleResearchpeer-review

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 languageEnglish
JournalPhytochemistry
Volume157
Pages (from-to)168-174
ISSN0031-9422
DOIs
Publication statusPublished - 2019

Keywords

  • Apiaceae
  • Bulnesol
  • CYP76AE4
  • Epikunzeaol
  • Guaiol
  • Sesquiterpenoid
  • Thapsia laciniata
  • Tovarol

Cite this

Andersen, Trine Bundgaard ; Rasmussen, Silas Anselm ; Christensen, Søren Brøgger ; Simonsen, Henrik Toft. / Biosynthesis of tovarol and other sesquiterpenoids in Thapsia laciniata Rouy. In: Phytochemistry. 2019 ; Vol. 157. pp. 168-174.
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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 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.",
keywords = "Apiaceae, Bulnesol, CYP76AE4, Epikunzeaol, Guaiol, Sesquiterpenoid, Thapsia laciniata, Tovarol",
author = "Andersen, {Trine Bundgaard} and Rasmussen, {Silas Anselm} and Christensen, {S{\o}ren Br{\o}gger} and Simonsen, {Henrik Toft}",
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Biosynthesis of tovarol and other sesquiterpenoids in Thapsia laciniata Rouy. / Andersen, Trine Bundgaard; Rasmussen, Silas Anselm; Christensen, Søren Brøgger; Simonsen, Henrik Toft.

In: Phytochemistry, Vol. 157, 2019, p. 168-174.

Research output: Contribution to journalJournal articleResearchpeer-review

TY - JOUR

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

Y1 - 2019

N2 - 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.

AB - 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.

KW - Apiaceae

KW - Bulnesol

KW - CYP76AE4

KW - Epikunzeaol

KW - Guaiol

KW - Sesquiterpenoid

KW - Thapsia laciniata

KW - Tovarol

U2 - 10.1016/j.phytochem.2018.10.027

DO - 10.1016/j.phytochem.2018.10.027

M3 - Journal article

VL - 157

SP - 168

EP - 174

JO - Phytochemistry

JF - Phytochemistry

SN - 0031-9422

ER -