Natural Friedelanes

Abstract

This review covers the occurrence and biological activities of all natural friedelane triterpenoids found between 1977 and March 2011. The biogeneses of dimeric friedelanes and several rearranged friedelanes are discussed. The pharmacological properties of representative compounds, including celastrol and correolide, have also been compiled, on the basis of 344 references.

Integrative Approaches for the Identification and Localization of Specialized Metabolites in Tripterygium Roots

“…While sesquiterpene polyesters have been isolated primarily from fruit, sesquiterpene pyridine alkaloid macrolides are present in several organs, and their concentrations are often fairly high in roots (Gao et al, 2007). Friedelane triterpenoids are a third prominent class of specialized metabolites in the Celastraceae (more than 50 structures; Shan et al, 2013), and our searches indicated that 26 different friedelanes have been described in Tripterygium.…”

Employing Two‐stage Derivatisation and GC–MS to Assay for Cathine and Related Stimulant Alkaloids across the Celastraceae

“…Of the 27 compounds detected from our workflow, 18 were annotated as sterol‐like, eight were annotated as terpene‐ or terpenoid‐like, and one did not match well to any compound type in the metabolite databases used. A wide diversity of terpenes, including numerous unique types, have been described from the Celastraceae (Shan et al ., ). The bioactivity of terpenes in the Celastraceae has been studied within certain species given their potential application as painkillers, cancer treatments, anti‐HIV agents, diabetes treatments, and antidepressants (Shan et al ., ).…”

“…Five compounds annotated as terpenes were found in high abundance in Cassine schinoides , one in Pseudocatha mandenensis , one in Peripterygia marginata, and one found in both Pseudocatha mandenensis and Cheiloclinum hippocratedides (Figs ) . As with sterols, terpenes are commonly found in the Celastraceae (Shan et al ., ). It appears that the species Cassine schinoides , Pseudocatha mandenensis, and Cheiloclinium hippocrateoides have not been part of any published phytochemical work on terpenes.…”

“…Despite ongoing phytochemical research in Celastraceae, a systematic investigation to identify cathinone and cathine as well as precursors and possible derivatives thereof has not been undertaken in this family. Much of the phytochemical research in Celastraceae has focussed on molecules, such as terpenoids, that have unique structures and potential as pharmaceutical products (reviewed in Shan et al ., ). Here, the presence of cathine in Celastraceae species other than Catha edulis is hypothesised based on the following two reasons.…”

Triterpenoids

“…222 A review of naturally occurring friedelanes, isolated between 1977 and March 2011 has been published. 301 Ovalifolones A 556 and B 557, from Garcinia ovalifolia, 302 Clerodendrumic acid 624, from Clerodendrum glabrum, has also be reported with this stereochemistry. 337 The acetonide 625 is likely to be an artefact from chromatography of the extract of Rhododendron hainanense.…”