Cherbonolides M and N from a Formosan Soft Coral Sarcophyton cherbonnieri

Two new isosarcophine derivatives, cherbonolides M (1) and N (2), were further isolated from a Formosan soft coral Sarcophyton cherbonnieri. The planar structure and relative configuration of both compounds were established by the detailed analysis of the IR, MS, and 1D and 2D NMR data. Further, the...

Full description

Saved in:
Bibliographic Details
Published in:Marine drugs 2021-05, Vol.19 (5), p.260
Main Authors: Peng, Chia-Chi, Huang, Tzu-Yin, Huang, Chiung-Yao, Hwang, Tsong-Long, Sheu, Jyh-Horng
Format: Article
Language:English
Subjects:
Absolute configuration
Anions
anti-inflammatory activity
Carbon
Cell lines
Configurations
Corals
Cytochalasin B
Cytotoxicity
Elastase
Formyl peptides
Inflammation
Infrared analysis
isosarcophine derivatives
Leukocytes (neutrophilic)
Metabolites
Natural products
NMR
Nuclear magnetic resonance
Oxidation
Phenylalanine
Planar structures
Proliferation
Sarcophyton
Sarcophyton cherbonnieri
Superoxide anions
tetrahydrooxepane
Toxicity
Citations: Items that this one cites
Items that cite this one
Online Access:Get full text
Tags: Add Tag
No Tags, Be the first to tag this record!
Description
Summary:Two new isosarcophine derivatives, cherbonolides M (1) and N (2), were further isolated from a Formosan soft coral Sarcophyton cherbonnieri. The planar structure and relative configuration of both compounds were established by the detailed analysis of the IR, MS, and 1D and 2D NMR data. Further, the absolute configuration of both compounds was determined by the comparison of CD spectra with that of isosarcophine (3). Notably, cherbonolide N (2) possesses the unique cembranoidal scaffold of tetrahydrooxepane with the 12,17-ether linkage fusing with a γ-lactone. In addition, the assay for cytotoxicity of both new compounds revealed that they showed to be noncytotoxic toward the proliferation of A549, DLD-1, and HuCCT-1 cell lines. Moreover, the anti-inflammatory activities of both metabolites were carried out by measuring the N-formyl-methionyl-leucyl-phenylalanine/cytochalasin B (fMLF/CB)-induced generation of superoxide anion and elastase release in the primary human neutrophils. Cherbonolide N (2) was found to reduce the generation of superoxide anion (20.6 ± 6.8%) and the elastase release (30.1 ± 3.3%) in the fMLF/CB-induced human neutrophils at a concentration of 30 μM.
ISSN:1660-3397
1660-3397
DOI:10.3390/md19050260