Plant-like cadinane sesquiterpenes from an actinobacterial mangrove endophyte.
2D NMR
NMR
Streptomyces
cadinane
endophyte
epicubenol
sesquiterpene
terpene
Journal
Magnetic resonance in chemistry : MRC
ISSN: 1097-458X
Titre abrégé: Magn Reson Chem
Pays: England
ID NLM: 9882600
Informations de publication
Date de publication:
01 2021
01 2021
Historique:
received:
24
03
2020
revised:
23
06
2020
accepted:
26
06
2020
pubmed:
1
7
2020
medline:
20
7
2021
entrez:
30
6
2020
Statut:
ppublish
Résumé
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.
Substances chimiques
Polycyclic Sesquiterpenes
0
cadinane
0
Types de publication
Journal Article
Research Support, Non-U.S. Gov't
Langues
eng
Sous-ensembles de citation
IM
Pagination
34-42Subventions
Organisme : Bundesministerium für Bildung und Forschung
ID : Intercommunicate
Informations de copyright
© 2020 John Wiley & Sons, Ltd.
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