Natural sesquiterpenoids

Abstract

This review covers the isolation, structural determination, synthesis and chemical and microbiological transformations of natural sesquiterpenoids. The literature is reviewed, and 435 references are cited.

The Chemistry of the Sesquiterpene Alkaloids

“…16 The biogenesis is shown in Scheme 3, and goes from farnesyl pyrophosphate to the basic guaiane skeleton. Cleavage of a C=C double bond at the bicycle junction produces the xanthane sesquiterpene skeleton, 17 and inclusion of a nitrogen atom between the two carbonyl groups then finalises the sequence to the guaipyridine framework.…”

Four New Chloro-Eremophilane Sesquiterpenes from an Antarctic Deep-Sea Derived Fungus, Penicillium sp. PR19N-1

“…Eremophilane-type sesquiterpenes as a subclass of sesquiterpenoids have gained considerable attentions due to diverse structures and a broad range of biological activities [23,24], most of them distributed in terrestrial plants or microorganisms. To date, more than 900 eremophilane-type sesquiterpenes have been discovered, and to the best of our knowledge, it is the first example that chloro-eremophilane sesquiterpenes were found from microorganisms in the past 30 years.…”

Capgermacrenes A and B, Bioactive Secondary Metabolites from a Bornean Soft Coral, Capnella sp.

“…from Mantanani Island (Sabah, Malaysia) and it has led to the isolation of bicyclogermacrenes as first report in Bornean soft corals. The methanol extract gave two new bicyclogermacrenes, capgermacrenes A ( 1 ) and B ( 2 ), in addition to two known compounds, palustrol ( 3 ) [6] and litseagermacrane ( 4 ) [7,8] (Figure 1). Anti-inflammatory activity of capgermacrene A ( 1 ) in LPS-induced RAW 264.7 macrophages exhibited down-regulation of inflammatory mediator such as nitric oxide (NO), prostaglandin-E2 (PGE 2 ), tumor necrosis factor-α (TNF-α), interleukin 1β (IL-1β), interleukin 6 (IL-6), inducible nitric oxide synthase (iNOS) and cyclooxygenase-2 (COX-2).…”