Biosynthesis of tovarol and other sesquiterpenoids in Thapsia laciniata Rouy
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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, No. https://doi.org/10.1016/j.phytochem.2018.10.027, 01.2019, p. 168-174.Research output: Contribution to journal › Journal article › Research › peer-review
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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 - 2019/1
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
VL - 157
SP - 168
EP - 174
JO - Phytochemistry
JF - Phytochemistry
SN - 0031-9422
IS - https://doi.org/10.1016/j.phytochem.2018.10.027
ER -
ID: 204530534