New Bioactive Sulfated Alkenes from the Sea Cucumber Apostichopus japonicus

Two new alkene sulfates, (5Z)‐dec‐5‐en‐1‐yl sulfate (4) and (3E)‐dec‐3‐en‐1‐yl sulfate (5), together with three known sulfated alkanes, 2,6‐dimethylheptyl sulfate (1), octyl sulfate (2), and decyl sulfate (3), were isolated from the sea cucumber Apostichopus japonicus. The structures of the new comp...

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Bibliographic Details
Published in:Chemistry & biodiversity 2012-06, Vol.9 (6), p.1166-1171
Main Authors: La, Ming-Ping, Li, Cui, Li, Ling, Sun, Peng, Tang, Hua, Liu, Bao-Shu, Gong, Wei, Han, Hua, Yi, Yang-Hua, Zhang, Wen
Format: Article
Language:English
Subjects:
Alkanes - chemistry
Alkanes - isolation & purification
Alkanes - pharmacology
Alkenes - chemistry
Alkenes - isolation & purification
Alkenes - pharmacology
Alkenyl sulfate
Animals
Anti-Bacterial Agents - chemistry
Anti-Bacterial Agents - isolation & purification
Anti-Bacterial Agents - pharmacology
Antibacterial activity
Antifungal activity
Antifungal Agents - chemistry
Antifungal Agents - isolation & purification
Antifungal Agents - pharmacology
Apostichopus japonicus
Bacillus megaterium - drug effects
Cytotoxic activity
Decenyl sulfate
Escherichia coli - drug effects
Magnetic Resonance Spectroscopy
Mass Spectrometry
Molecular Conformation
Sea cucumbers
Sea Cucumbers - chemistry
Sulfates - chemistry
Sulfuric Acid Esters - chemistry
Sulfuric Acid Esters - isolation & purification
Sulfuric Acid Esters - pharmacology
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Summary:Two new alkene sulfates, (5Z)‐dec‐5‐en‐1‐yl sulfate (4) and (3E)‐dec‐3‐en‐1‐yl sulfate (5), together with three known sulfated alkanes, 2,6‐dimethylheptyl sulfate (1), octyl sulfate (2), and decyl sulfate (3), were isolated from the sea cucumber Apostichopus japonicus. The structures of the new compounds 4 and 5 were elucidated by spectroscopic analysis, including 1H‐, 13C‐, and 2D‐NMR, ESI‐MS, and HR‐ESI‐MS. Compounds 2 and 3 were isolated from natural sources for the first time. In preliminary bioassays in vitro, compounds 4 and 5 showed antibacterial, antifungal, and cytotoxic activities.
ISSN:1612-1872
1612-1880
DOI:10.1002/cbdv.201100324