Dimeric Sesquiterpenoids

Abstract

It is widely accepted that a large number of proteins that are responsible for cellular function exist as dimers or need to be activated by dimerization before mediating certain signaling pathways. Simultaneously targeting both monomeric moieties of the dimeric proteins has shown potential in the development of various therapeutic agents. As dimeric molecules might be able to act on both moieties of a dimeric protein, dimeric sesquiterpenoids (DSs), which are generated biogenetically from coupling of two sesquiterpenoid molecules, are in essence potential biologically active molecules, and have attracted in recent years great attention for their peculiar structures and biological activities. In fact, a number of DSs are more potent than their monomeric precursors for some activities such as anti-inflammatory, anti-tumor, immunosuppressive, potassium channel blocking, antimalarial, anti-virus, and neurotrophic activities.The complex and diversified structures of DSs also attracted attention of chemists in their isolation, structural elucidation, and synthetic construction.In the contribution, a general view of the classification and distribution of DSs will be provided. Strategies for the structural elucidation of DSs and their analogues is presented. Chemical strategies for the convergence of the two sesquiterpenoid units is reviewed. Biological activities are discussed under each type of activity.

Vlasouliolides A-D, four rare C17/C15 sesquiterpene lactone dimers with potential anti-inflammatory activity from Vladimiria souliei

“…Since the first SLD absinthin was isolated from Artemisia absinthium in 1953 3 , more than 160 SLDs have been obtained. To the best of our knowledge, most of the published SLDs have C 30 cores derived from two C 15 sesquiterpenoid units 4 5 6 .…”

New terpenoids from the fermentation broth of the edible mushroom Cyclocybe aegerita

“…This includes polyacetylenes [9–10] as well as sesquiterpenoids with illudine [11], aromadendrane [12], marasmene [13] and fomannosane [14] type skeletons. Although bovistol could formally be supposed to be a triterpene, it is thought to be derived by a hetero-Diels–Alder reaction of two sesquiterpenes to form a dimeric sesquiterpenoid [15].…”

Artematrovirenolides A—D and Artematrolides S—Z, Sesquiterpenoid Dimers with Cytotoxicity against Three Hepatoma Cell Lines from Artemisia atrovirens

“…Up to now, a variety of sesquiterpenoid dimers with potential in the treatment of liver cancer [ 6‐7 ] and antiinflammatory activities have been isolated from Artemisia species. [ 8‐19 ] Guaiane‐type sesquiterpenoid dimers are the main classes of sesquiterpenoid dimers in this genus, predominantly composed of two alike or unlike monomeric sesquiterpene lactone units through different connecting model. Chemical investigations showed that 77 guaiane‐type sesquiterpenoid dimers had been identified from Artemisia plants in the last 40 years, and most of them were generated via intermolecular Diels–Alder reaction to produce an additional cyclohexene moiety.…”