New bioactive sulfated alkenes from the sea cucumber Apostichopus japonicus

Chem Biodivers. 2012 Jun;9(6):1166-71. doi: 10.1002/cbdv.201100324.

Abstract

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.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Alkanes / chemistry*
  • Alkanes / isolation & purification
  • Alkanes / pharmacology
  • Alkenes / chemistry*
  • Alkenes / isolation & purification
  • Alkenes / pharmacology
  • Animals
  • Anti-Bacterial Agents / chemistry
  • Anti-Bacterial Agents / isolation & purification
  • Anti-Bacterial Agents / pharmacology
  • Antifungal Agents / chemistry
  • Antifungal Agents / isolation & purification
  • Antifungal Agents / pharmacology
  • Bacillus megaterium / drug effects
  • Escherichia coli / drug effects
  • Magnetic Resonance Spectroscopy
  • Mass Spectrometry
  • Molecular Conformation
  • Sea Cucumbers / chemistry*
  • Sulfates / chemistry*
  • Sulfuric Acid Esters / chemistry*
  • Sulfuric Acid Esters / isolation & purification
  • Sulfuric Acid Esters / pharmacology

Substances

  • (3E)-dec-3-en-1-yl sulfate
  • (5Z)-dec-5-en-1-yl sulfate
  • Alkanes
  • Alkenes
  • Anti-Bacterial Agents
  • Antifungal Agents
  • Sulfates
  • Sulfuric Acid Esters