Sesquiterpene Lactones from Artemisia absinthium. Biotransformation and Rearrangement of the Insect Antifeedant 3α-hydroxypelenolide.

Braulio M Fraga,María Bailén,Azucena González-Coloma,Carmen E Díaz

doi:10.3390/plants10050891

Abstract

Three new compounds, the sesquiterpenes absilactone and hansonlactone and the acetophenone derivative ajenjol, have been isolated from a cultivated variety of Artemisia absinthium. In addition, the major lactone isolated, 3α-hydroxypelenolide, was biotransformed by the fungus Mucor plumbeus affording the corresponding 1β, 10α-epoxide. A cadinane derivative was formed by an acid rearrangement produced in the culture medium, but not by the enzymatic system of the fungus. Furthermore, 3α-hydroxypelenolide showed strong antifeedant effects against Leptinotarsa decemlineata and cytotoxic activity to Sf9 insect cells, while the biotransformed compounds showed antifeedant postingestive effects against Spodoptera littoralis.

Highlights

Plants 2021, 10, 891. https://doi.org/The Artemisia genus with more of 400 species is one of the largest genera in the Asteraceae family
In this work we describe three unknown compounds, the sesquiterpene lactones absilactone (1) and hansonlactone (2) and the acetophenone derivative artenol (12) [4], isolated from A. absinthium var. candial along with several known compounds
Absilactone is a new nor-sesquiterpene, which structure has been determined as 1 based on the following considerations: Its high-resolution mass spectrum showed the molecular ion at m/z 248.1040, which corresponds to the molecular formula C14 H16 O4

Summary

Introduction

Plants 2021, 10, 891. https://doi.org/The Artemisia genus with more of 400 species is one of the largest genera in the Asteraceae family. The Artemisia genus with more of 400 species is one of the largest genera in the Asteraceae family. The species Artemisia absinthium L., known as wormwood, is a perennial medicinal species which has been widely investigated due to its ethno-pharmacological interest. A. absinthium is abundant in the mountains of Spain as a ruderal species. There are seven chemotypes described in the Iberian Peninsula [1]. Candial) has been domesticated for the production of essential oil [2]. The oil characterized by the presence of cis-epoxyocimene, (−)-cis-chrysanthenol, chrysanthenyl acetate, linalool and trans-caryophyllene showed strong antifungal effects [2]. Two ocimene monoterpenes were isolated and their absolute configurations determined by vibrational circular dichroism (VCD) [3]

Methods

Results

Conclusion