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Biosynthesis of tovarol and other sesquiterpenoids in Thapsia laciniata Rouy
Phytochemistry ( IF 3.2 ) Pub Date : 2019-01-01 , DOI: 10.1016/j.phytochem.2018.10.027
Trine Bundgaard Andersen , Silas Anselm Rasmussen , Søren Brøgger Christensen , Henrik Toft Simonsen

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.

中文翻译:

木瓜中托伐醇和其他倍半萜类化合物的生物合成

Thapsia 属产生多种倍半萜类化合物。众所周知,地中海植物 Thapsia laciniata Rouy 的产品特征与该属中的其他几个物种不同。因此,研究了在 Thapsia laciniata Rouy 中倍半萜类化合物的生物合成。在这里,我们描述了三种萜烯合酶,TlTPS820、TlTPS509 和 TlTPS18983。TlTPS18983 是一种多产物酶,以法呢烯为主要产物,而 TlTPS509 产生愈创木酚和布尼醇以及其他主要和几种次要的未知产物。TlTPS820 与来自 Thapsia garganica L. 的 TgTPS2 直系同源,并且是一种表昆玉米醇合酶。来自 Thapsia garganica 的 TgCYP76AE2 在 C-12 处对表昆西醇进行三重羟基化以制备二氢木香内酯。因此研究了细胞色素 P450、TlCYP76AE4 是否能够使用表昆玉米醇作为底物。
更新日期:2019-01-01
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