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 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.
Research Center for Marine Drugs, School of Pharmacy, Second Military Medical University, 325 Guo-He Road, Shanghai 200433, P. R. China.
Ming-Ping
MP
La
Cui
C
Li
Ling
L
Li
Peng
P
Sun
Hua
H
Tang
Bao-Shu
BS
Liu
Wei
W
Gong
Hua
H
Han
Yang-Hua
YH
Yi
Wen
W
Zhang
D000473:Alkanes / Q000737:chemistry* / Q000302:isolation & purification / Q000494:pharmacology; D000475:Alkenes / Q000737:chemistry* / Q000302:isolation & purification / Q000494:pharmacology; D000818:Animals; D000900:Anti-Bacterial Agents / Q000737:chemistry / Q000302:isolation & purification / Q000494:pharmacology; D000935:Antifungal Agents / Q000737:chemistry / Q000302:isolation & purification / Q000494:pharmacology; D001410:Bacillus megaterium / Q000187:drug effects; D004926:Escherichia coli / Q000187:drug effects; D009682:Magnetic Resonance Spectroscopy; D013058:Mass Spectrometry; D008968:Molecular Conformation; D012616:Sea Cucumbers / Q000737:chemistry*; D013431:Sulfates / Q000737:chemistry*; D013463:Sulfuric Acid Esters / Q000737:chemistry* / Q000302:isolation & purification / Q000494:pharmacology
C575703:(3E)-dec-3-en-1-yl sulfate; C575702:(5Z)-dec-5-en-1-yl sulfate; D000473:Alkanes; D000475:Alkenes; D000900:Anti-Bacterial Agents; D000935:Antifungal Agents; D013431:Sulfates; D013463:Sulfuric Acid Esters