Insect antifeedant properties of withanolides and related steroids from Solanaceae

Abstract

Physalisperuviana shrubs were not attacked by larvae of Spodoptera littoralis. It was demonstrated that withanolide E, a steroid isolated from P.peruviana, as well as several related steroids, have insect antifeedant properties.

Withanolides and related ergostane-type steroids as antifeedants for larvae ofEpilachna varivestis (Coleoptera: Chrysomelidae)

“…In the second group, IV (withaferin A) and V (withanolide D) were inactive against S. littoralis at the screening dose of 0.01% used in the previous study (1). In the present work, these two compounds were not active according to our criterion of activity below the highest concentration tested, 0.1%.…”

“…In a recent study (1) it was shown that certain ergostane-type steroids isolated from the leaves of several solanaceous plants, as well as some closely related products (5), have a considerable antifeedant effect for larvae of a lepidopterous insect, the Egyptian cotton leafworm, Spodoptera littoralis (Boisd.). The most active compounds were withanolide E (I) and its 2,3-dihydro-l~-hydroxy derivative (III).…”

Bioactive phytochemicals, nutritional value, and functional properties of cape gooseberry (Physalis peruviana): An overview

“…Withanolides exhibited a broad spectrum of biological properties and significant pharmacological activities, including insect-antifeedant, insect-repellent activities, hepatoprotective, immunomodulatory, antibacterial, anti-inflammatory, antitumor, cytotoxic activity, and protection against CCl 4 -induced hepatoxicity (Glotter, 1991;Lan et al, 2009;Veleiro, Oberti, & Burton, 2005). An insect-antifeedant property of withanolide E isolated from P. peruviana has been demonstrated against Spodoptera littoralis larvae (Ascher et al, 1980). Withanolide E and 4β-hydroxywithanolide E have been tested as anticancer agents (Cassady & Suffness, 1980).…”

Withasteroids, a Growing Group of Naturally Occurring Steroidal Lactones

“…The insect repellent and insecticidal properties of nicandrenone (189) and the insect antifeedant property of withanolide E (150) and of a number of related natural and synthetically modified withanolides have been studied (13,84,94,254). Further investigation of this property of withasteroids is expected to yield fruitful results.…”

“…The key steps in the recent synthesis of this substance by PEREZ-MEDRANO and GRIECO (226) were the insertion of a hydroxyl group at the 14a-position and introduction of the 17J3-hydroxyl group. The former was achieved by a hetero Diels-Alder reaction between steroidal dienol acetate (252) and benzyl nitrosoformate and subsequent transformation of the desired adduct to 14a-hydroxy-17-oxo-androstane derivative (254). Attempts to introduce 17J3-hydroxyl group by addition of appro- References pp.…”