C29 sterols with a cyclopropane ring at C-25 and 26 from the Vietnamese marine sponge Ianthella sp. and their anticancer properties

Bioorg Med Chem Lett. 2009 Aug 15;19(16):4584-8. doi: 10.1016/j.bmcl.2009.06.097. Epub 2009 Jul 2.

Abstract

Two new C(29) sterols with a cyclopropane ring at C-25 and C-26, petrosterol-3,6-dione (1) and 5alpha,6alpha-epoxy-petrosterol (2), along with petrosterol (3), were isolated from the Vietnamese marine sponge Ianthella sp. The structures of the new compounds were elucidated by comprehensive spectroscopic analyses. Compounds 1-3 showed cytotoxic activities on A549, HL-60, MCF-7, SK-OV-3, and U937 cancer cell lines with IC(50) in the range of 8.4-22.6 microM, whereas compounds 1-3 exhibited only weak cytotoxic activities on HT-29 cell. After HL-60 cells were treated with the compounds, several apoptosis events like chromatin condensation and the increase of the population of sub-G1 hypodiploid cells were observed. These data supported that the compounds might have potential for leukemia treatment.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Animals
  • Antineoplastic Agents / chemistry*
  • Antineoplastic Agents / isolation & purification
  • Antineoplastic Agents / pharmacology
  • Cell Line
  • Drug Screening Assays, Antitumor
  • HL-60 Cells
  • Humans
  • Porifera / chemistry*
  • Sterols / chemistry*
  • Sterols / isolation & purification
  • Sterols / pharmacology
  • Vietnam

Substances

  • 5alpha,6alpha-epoxy-petrosterol
  • Antineoplastic Agents
  • Sterols
  • petrosterol-3,6-dione
  • petrosterol