Journal article
Plant‐like Cadinane Sesquiterpenes from an Actinobacterial Mangrove Endophyte
Center for Microbial Secondary Metabolites, Centers, Technical University of Denmark1
DTU Metabolomics Core, Section for Microbial and Chemical Ecology, Department of Biotechnology and Biomedicine, Technical University of Denmark2
Section for Microbial and Chemical Ecology, Department of Biotechnology and Biomedicine, Technical University of Denmark3
Natural Product Discovery, Section for Microbial and Chemical Ecology, Department of Biotechnology and Biomedicine, Technical University of Denmark4
Department of Biotechnology and Biomedicine, Technical University of Denmark5
Friedrich Schiller University Jena6
Leibniz Institute for Natural Product Research and Infection Biology - Hans Knöll Institute7
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.
| Language: | English |
|---|---|
| Year: | 2021 |
| Pages: | 34-42 |
| ISSN: | 1097458x and 07491581 |
| Types: | Journal article |
| DOI: | 10.1002/mrc.5070 |
| ORCIDs: | Ding, Ling and 0000-0002-0367-337X |
