Synthesis of Pertyolides A, B, and C: A Synthetic Procedure to C17-Sesquiterpenoids and a Study of Their Phytotoxic Activity,Journal of Natural Products

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Synthesis of Pertyolides A, B, and C: A Synthetic Procedure to C17-Sesquiterpenoids and a Study of Their Phytotoxic Activity
Journal of Natural Products ( IF 3.3 ) Pub Date : 2021-08-09 , DOI: 10.1021/acs.jnatprod.1c00396
David M Cárdenas ₁ , Carlos Rial ₁ , Rosa M Varela ₁ , José M G Molinillo ₁ , Francisco A Macías ₁

Affiliation

C₁₇-sesquiterpenoids are a group of natural products that have been recently discovered. These compounds have the peculiarity of lacking the α,β-methylene butyrolactone system, which is known to be quite relevant for many of the biological activities reported for sesquiterpene lactones. Unfortunately, the biological interest of C₁₇-sesquiterpenoids has not been studied in-depth, mainly due to the poor isolation yields in which they can be obtained from natural sources. Therefore, in order to allow a deeper study of these novel molecules, we have worked out a synthetic pathway that provides C₁₇-sesquiterpenoids in enough quantities from easily accessible sesquiterpene lactones to enable a more thorough investigation of their bioactivities. With this synthesis method, we have successfully synthesized, for the first time, three natural C₁₇-sesquiterpenoids, pertyolides A, B, and C, with good overall yields. Furthermore, we have also evaluated their phytotoxicity against etiolated wheat coleoptiles and corroborated that pertyolides B and C present strong phytotoxic activity.

中文翻译：

Pertyolides A、B 和 C 的合成：C17-倍半萜类化合物的合成方法及其植物毒性活性研究

C _{17 -}倍半萜类化合物是最近发现的一组天然产物。这些化合物的特点是缺乏 α,β-亚甲基丁内酯系统，众所周知，该系统与倍半萜内酯的许多生物活性非常相关。不幸的是，C _{17 -}倍半萜类化合物的生物学意义尚未得到深入研究，这主要是因为它们可以从天然来源获得的分离产率很低。因此，为了对这些新分子进行更深入的研究，我们制定了一条合成途径，提供 C ₁₇- 从易于获得的倍半萜内酯中提取足够数量的倍半萜类化合物，以便对其生物活性进行更彻底的研究。使用这种合成方法，我们首次成功合成了三种天然C _{17 -}倍半萜类化合物pertyolides A、B 和C，并具有良好的总收率。此外，我们还评估了它们对黄化小麦胚芽鞘的植物毒性，并证实了 pertyolides B 和 C 具有很强的植物毒性活性。

更新日期：2021-08-27

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