New sesquiterpene derivatives from the red alga Laurencia scoparia. Isolation, structure determination, and anthelmintic activity

J Nat Prod. 2001 Dec;64(12):1552-5. doi: 10.1021/np0102307.

Abstract

Eleven sesquiterpenes (1-11) and one long chain aldehyde (12) have been isolated from the dichloromethane extract of the red alga Laurencia scoparia. Four of them are new natural products. Scopariol (1) is a new natural product with an unusual rearranged chamigrane-type structure. The other three are beta-chamigrenes: isorigidol (2), (+)-3-(Z)-bromomethylidene-10 beta-bromo-beta-chamigrene (3), and (-)-3-(E)-bromomethylidene-10 beta-bromo-beta-chamigrene (4). The in vitro activity of compounds 1-12 against the parasitant stage of Nippostrongylus brasiliensis (L4) has been studied.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Animals
  • Anthelmintics / chemistry
  • Anthelmintics / isolation & purification*
  • Anthelmintics / pharmacology
  • Brazil
  • Chromatography, Thin Layer
  • In Vitro Techniques
  • Molecular Conformation
  • Molecular Structure
  • Nippostrongylus / drug effects*
  • Nuclear Magnetic Resonance, Biomolecular
  • Rhodophyta / chemistry*
  • Sesquiterpenes / chemistry
  • Sesquiterpenes / isolation & purification*
  • Sesquiterpenes / pharmacology
  • Spectroscopy, Fourier Transform Infrared
  • Spiro Compounds / chemistry
  • Spiro Compounds / isolation & purification*
  • Spiro Compounds / pharmacology
  • Stereoisomerism
  • Structure-Activity Relationship

Substances

  • 3-bromomethylidene-10-bromochamigren
  • 8-bromo-3,7,7-trimethyl-11-methylenespiro(5.5)-undec-1-ene-3,9-diol
  • Anthelmintics
  • Sesquiterpenes
  • Spiro Compounds
  • scopariol