Synthesis of Pertyolides A, B, and C: A Synthetic Procedure to C-17-Sesquiterpenoids and a Study of Their Phytotoxic Activity

C-17-sesquiterpenoids are a group of natural products that have been recently discovered. These compounds have the peculiarity of lacking the alpha,beta-methylene butyrolactone system, which is known to be quite relevant for many of the biological activities reported for sesquiterpene lactones. Unfo...

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Bibliographic Details
Published inJournal of natural products (Washington, D.C.) Vol. 84; no. 8; pp. 2295 - 2302
Main Authors Cardenas, David M., Rial, Carlos, Varela, Rosa M., Molinillo, Jose M. G., Macias, Francisco A.
Format Journal Article
LanguageEnglish
Published WASHINGTON Amer Chemical Soc 27.08.2021
Subjects
Chemistry, Medicinal
Herbicides - chemical synthesis
Inula - chemistry
Life Sciences & Biomedicine
Molecular Structure
Pharmacology & Pharmacy
Plant Roots - chemistry
Plant Sciences
Science & Technology
Sesquiterpenes - chemical synthesis
Sesquiterpenes - toxicity
Triticum - drug effects
BIOLOGICAL-ACTIVITIES
ALLELOCHEMICALS
PHOTOCHEMICAL ADDITION
MODELS
NATURAL-PRODUCTS
SESQUITERPENE LACTONES
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Summary:C-17-sesquiterpenoids are a group of natural products that have been recently discovered. These compounds have the peculiarity of lacking the alpha,beta-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 C-17-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 C-17-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 C-17-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.
ISSN:0163-3864
1520-6025
DOI:10.1021/acs.jnatprod.1c00396