Jump to main content
Jump to site search
Access to RSC content Close the message box

Continue to access RSC content when you are not at your institution. Follow our step-by-step guide.



Plant triterpenoids with bond-missing skeletons: biogenesis, distribution and bioactivity

Author affiliations

Abstract

Covering: up to December 2018

The polycyclic ABCD(E) framework of triterpenoids can miss a single endocyclic C–C bond as a result of a modification of the cyclization cascade that triggers their formation (interrupted- or diverted cascades), or can be the result of post-cyclization ring cleavage by late-stage oxidative modifications (seco-triterpenoids). Because of mechanistic and biogenetic differences, ring opening associated with loss of a skeletal fragment, as in nor-seco-triterpenoids (limonoids, quassinoids), will not be covered, nor will compounds where ring opening is part of a fragmentation cascade or of a multiple diversion from it. Even with these limitations, 342 bond-missing triterpenoids could be retrieved from the literature, with transversal distribution in the plant kingdom. Their structural diversity translates into a variety of biological targets, with dominance of potential applications in the realm of cancer, neuroprotection, and anti-infective therapy. In addition to the bioactivity and chemotaxonomic relevance of bond-missing triterpenoids, current knowledge on the genetic basis of interrupted- and diverted oxidosqualene cyclases will be summarized. This untapped source of enzymes could be useful to selectively modify triterpenoids by metabolic engineering, circumventing the bottlenecks of their isolation (poor yield or inadequate supply chain) to explore new areas of their chemical space.

Graphical abstract: Plant triterpenoids with bond-missing skeletons: biogenesis, distribution and bioactivity

Back to tab navigation

Supplementary files

Article information


Submitted
16 May 2019
First published
05 May 2020

Nat. Prod. Rep., 2020, Advance Article
Article type
Review Article

Plant triterpenoids with bond-missing skeletons: biogenesis, distribution and bioactivity

A. Almeida, L. Dong, G. Appendino and S. Bak, Nat. Prod. Rep., 2020, Advance Article , DOI: 10.1039/C9NP00030E

Social activity

Search articles by author

Spotlight

Advertisements