Illudane-type sesquiterpenes: Challenges and opportunities for toxicology and chemotherapy

• Type: Chapter or Part of a Book
• Date: 2014

Authors

Gil da Costa, R. M. (Author) FEUP; Lopes, C (Author) Other; Oliveira, PA (Author) Other; Margarida M. S. M. Bastos (Author) FEUP

Book

Title: New Developments in Terpenes Research

Pages: 135-183

ISBN: 9781629487618; 9781629487601

Indexing

Scopus - 3 Citations

Associated Projects

UI0511 - PROJECTO ESTRATÉGICO - UI 511 - 2013-2014

Other information

Authenticus ID: P-00K-1RC

Abstract (EN): Illudanes are biologically active sesquiterpenes and nor-sesquiterpenes synthesized by fungal, vegetal and some marine organisms, via a protoilludane precursor. Illudanes commonly contain a reactive cyclopropane ring and present high reactivity towards nucleophiles, constituting an important part of defences against bacteria and insects. Since their discovery in the 1960s, illudane compounds became the focus of a dual interest due, on the one hand, to their potential therapeutic application as cytotoxic antitumour agents and, on the other hand, to their high toxicity towards mammals. Their comparatively stable illudalane derivatives include the well-known family of pterosinsand present a more favourable toxicity profile. Illudalanes have attracted attention as potential ant-diabetic and muscle-relaxant agents. One of the first illudanes isolated from Omphalotus illudens, illudin S (1), became the lead compound for the development of acylfulvenes, a new class of anti-neoplastics. Recent clinical trials of one such illudane derivative, hydroxymethylacylfulvene (162), suggest it may be useful for treating several malignancies, when used in combination therapies. The discovery of ptaquiloside (30), an illudane glycoside from bracken (Pteridium spp.), gave rise to a different line of research. Using different animal models, this nor-sesquiterpenoid has been shown to be a potent carcinogen, due to its DNA-alkylating and immunosuppressive properties. Additionally, the wide environmental contamination associated with ptaquiloside (30) ranges from the contamination of ground waters to that of foodstuffs of animal origin, such as milk and meat from bracken-fed cattle. Other ptaquiloside-related illudane-type molecules, whose toxicological profiles are little studied, are still being discovered in bracken and other ferns. The public health impact of ptaquiloside (30) and related illudanes remains the focus of intense concern and discussion.

Language: English

Type (Professor's evaluation): Scientific