4.5 Article

New Bioactive Sulfated Alkenes from the Sea Cucumber Apostichopus japonicus

Journal

CHEMISTRY & BIODIVERSITY
Volume 9, Issue 6, Pages 1166-1171

Publisher

WILEY-V C H VERLAG GMBH
DOI: 10.1002/cbdv.201100324

Keywords

Apostichopus japonicus; Decenyl sulfate; Alkenyl sulfate; Sea cucumbers; Antifungal activity; Antibacterial activity; Cytotoxic activity

Funding

  1. Natural Science Foundation of China [30873200, 41176125]
  2. STCSM [08JC1405600]
  3. Shanghai Leading Academic Discipline Project [B906]
  4. Shanghai Pujiang Program [PJ2008]
  5. International Science and Technology Cooperation of China [2010DFB30810]

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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.

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