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  • Title: Plant-like cadinane sesquiterpenes from an actinobacterial mangrove endophyte.
    Author: Ding L, Görls H, Hertweck C.
    Journal: Magn Reson Chem; 2021 Jan; 59(1):34-42. PubMed ID: 32598052.
    Abstract:
    Cadinanes are typical plant sesquiterpenes with a broad range of biological functions. We report the isolation of three cadinanes (1-3) from a bacterial endophyte (Streptomyces sp.) of the mangrove plant Bruguiera gymnorrhiza. The structures of two new cadinenes, (+)-11-hydroxy-epicubenol (1) and (+)-12-hydroxy-epicubenol (2) were elucidated by nuclear magnetic resonance (NMR) and mass spectrometry. The bacterial product (+)-11-hydroxy-epicubenol was elucidated to be an enantiomer of the plant product pubinernoid C. (+)-12-Hydroxy-epicubenol was established as a diastereomer of the basidiomycete product trichapargin A. In addition, a crystal structure analysis corroborated the structure and configuration of 5,11-epoxy-10-cadinanol (3), a cadinane cycloether initially described as a natural product from liverwort. The discovery of oxygenated cadinanes from a bacterial endophyte may set the basis for the production of cadinanes by bacterial fermentation.
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