Plant‐like Cadinane Sesquiterpenes from an Actinobacterial Mangrove Endophyte
| Autor: | Ling Ding, Christian Hertweck, Helmar Görls |
|---|---|
| Jazyk: | angličtina |
| Rok vydání: | 2021 |
| Předmět: |
Sesquiterpene
Magnetic Resonance Spectroscopy Stereochemistry Cadinane 010402 general chemistry Bruguiera 01 natural sciences Endophyte Streptomyces Terpene chemistry.chemical_compound Epicubenol General Materials Science 2D NMR Polycyclic Sesquiterpenes Natural product biology 010405 organic chemistry Stereoisomerism General Chemistry biology.organism_classification NMR 0104 chemical sciences chemistry Rhizophoraceae Fermentation Two-dimensional nuclear magnetic resonance spectroscopy |
| Zdroj: | Ding, L, Görls, H & Hertweck, C 2021, ' Plant-like Cadinane Sesquiterpenes from an Actinobacterial Mangrove Endophyte ', Magnetic Resonance in Chemistry, vol. 59, no. 1, pp. 34-42 . https://doi.org/10.1002/mrc.5070 |
| DOI: | 10.1002/mrc.5070 |
| Popis: | 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 cadinenens, (+)‐11‐hydroxy‐epicubenol (1 ) and (+)‐12‐hydroxy‐epicubenol (2 ) were elucidated by 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 liverworth. The discovery of oxygenated cadinanes from a bacterial endophyte may set the basis for the production of cadinanes by bacterial fermentation. |
| Databáze: | OpenAIRE |
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