Beilstein J. Org. Chem.2017,13, 2458–2465, doi:10.3762/bjoc.13.242
pathway. After large-scale fermentation of H. aurantiacus 114-95T, the putative diterpene was isolated in sufficient quantity to enable NMR-based structure elucidation. The compound, for which the name herpetopanone is proposed, features a rare octahydro-1H-indenyl skeleton. Herpetopanone bears
resemblance to cadinane-type sesquiterpenes from plants, but is structurally entirely unprecedented in bacteria. Based on its molecular architecture, a possible biosynthetic pathway is postulated.
Keywords: genome mining; herpetopanone; Herpetosiphon; isotope labeling; terpene; Introduction
Terpenoids
by flash column chromatography on RP silica gel. Fractions containing the target compound were identified by LC–MS, pooled and further purified via semipreparative RP–HPLC to give 19 mg of herpetopanone (1).
The IR spectrum of 1 revealed two distinctive bands at 3395 and 1699 cm−1, which were
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Graphical Abstract
Figure 1:
Distribution of isotopic labels from [1-13C]-glucose via the MEP (route a) and MEV pathway (route b...