Structure determination of two new sesquiterpenoids from Streptomyces sanglieri

Magnetic Resonance in Chemistry
2016.0

Abstract

Sesquiterpenoids are a group of abundant and structurally diverse secondary metabolites mainly derived from plant and fungi. By contrast, they are rarely isolated from bacteria, and the terpene synthase genes had been considered to be silent in prokaryotes.[1,2] Recently, more and more terpenes were identified from bacteria, and the biosynthesis of some terpenes has been discussed in heterologous bacteria.[3–6] Actually, it demonstrated that the terpene synthases are widely distributed in bacteria, including streptomycete, and some new sesquiterpenoids and diterpenoids had been obtained through heterologous expression of terpene synthase genes derived from Streptomyces microorganism.[7]In our ongoing investigation of new bioactive natural products from streptomycete, two new sesquiterpenes, 15-hydroxy-(+)-epicubenol (1) and 7β-hydroxy-7-epi-α-eudesmol (2), were identified from a fermentation broth of Streptomyces sanglieri (YIM 121209-2), which was isolated from the forest soil sample collected from Wuyi Mountain, Fujian Province, China. The structures of compounds 1 and 2 (Fig. 1) were elucidated based on detailed spectroscopic data analyses, including 1D and 2D NMR techniques. The cytotoxicity against two human cancer cell lines and antimicrobial activity against a panel of bacteria and fungi of 1 and 2 were evaluated. None of them showed cytotoxic or antimicrobial activities at 100 μg/ml.

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