Bis(sulfato)-cyclosiphonodictyol A, a new disulfated sesquiterpene-hydroquinone from a deep water collection of the Marine sponge Siphonodictyon coralliphagum

J Nat Prod. 1995 Jun;58(6):958-60. doi: 10.1021/np50120a024.

Abstract

A new compound, bis(sulfato)-cyclosiphonodictyol A [1], which inhibits the binding of [3H]-LTB4 to intact human neutrophils with an IC50 value of 44 microM, was isolated from the sponge Siphonodictyon coralliphagum. The sponge was collected using the Johnson-Sea-Link manned submersible at a depth of 195 feet in the Bahamas. The compound was isolated via reversed-phase chromatography and its structure determined spectroscopically. To the best of our knowledge, 1 is the first marine-derived compound with two aromatic sulfate ester functionalities, and is also the first in the siphonodictyal series to contain an oxepane functionality.

MeSH terms

  • Animals
  • Humans
  • In Vitro Techniques
  • Lipoxygenase Inhibitors / isolation & purification*
  • Lipoxygenase Inhibitors / pharmacology
  • Neutrophils / drug effects
  • Neutrophils / enzymology
  • Neutrophils / metabolism
  • Porifera / chemistry*
  • Receptors, Leukotriene B4 / antagonists & inhibitors
  • Sesquiterpenes / isolation & purification*
  • Sesquiterpenes / pharmacology

Substances

  • Lipoxygenase Inhibitors
  • Receptors, Leukotriene B4
  • Sesquiterpenes
  • bis(sulfato)-cyclosiphonodictyol A