New triterpenoid sulfates from the red alga Tricleocarpa fragilis

J Nat Prod. 2000 Feb;63(2):210-6. doi: 10.1021/np990448h.

Abstract

Ten new sulfated terpenoids, including six cycloartenol sulfates (1-6), two 29-nor-cycloartenol sulfates (7,8), and two 29-nor-lanosterol sulfates (9,10), were isolated from brine shrimp-toxic fractions of the methanolic extract of the red alga Tricleocarpa fragilis collected in Hawaiian waters. Structures 1-10 were elucidated by spectral methods, and the absolute stereochemistry for compound 1 at C23 was determined by Mosher analysis. Compounds 7 and 10 showed brine shrimp toxicity at 50 microg/mL, while 1 and 3 showed substantial activity at 17 microg/mL. Compounds 2, 4, 5, and 9 were inactive. In cytotoxicity assays, compounds 1-10 were inactive at concentrations tested.

Publication types

  • Research Support, Non-U.S. Gov't
  • Research Support, U.S. Gov't, Non-P.H.S.

MeSH terms

  • Animals
  • Artemia
  • Chromatography, High Pressure Liquid
  • Drug Screening Assays, Antitumor
  • Humans
  • Leukemia P388 / drug therapy
  • Magnetic Resonance Spectroscopy
  • Rhodophyta / chemistry*
  • Spectrometry, Mass, Fast Atom Bombardment
  • Spectrophotometry, Infrared
  • Sulfates
  • Triterpenes / chemistry
  • Triterpenes / isolation & purification*
  • Triterpenes / toxicity

Substances

  • Sulfates
  • Triterpenes