Caulerprenylols A and B, two rare antifungal prenylated para-xylenes from the green alga Caulerpa racemosa

Bioorg Med Chem Lett. 2013 May 1;23(9):2491-4. doi: 10.1016/j.bmcl.2013.03.038. Epub 2013 Mar 19.

Abstract

Two new prenylated para-xylenes, named caulerprenylols A (1) and B (2), were isolated from the green alga Caulerpa racemosa, collected from the Zhanjiang coastline, China. The structures of the two metabolites were elucidated on the basis of detailed spectroscopic analysis. This is the first report of prenylated para-xylenes from marine algae and from marine organisms as well. Moreover, caulerprenylol B (2) is also characterized by an uncommon indane ring system. In in vitro bioassays, the new compounds exhibited a broad spectrum of antifungal activity against Candida glabrata (537), Trichophyton rubrum (Cmccftla), and Cryptococcus neoformans (32609) with MIC80 values between 4 and 64 μg/mL when compared to amphotericin B (MIC80 values of 2.0, 1.0, and 4.0 μg/mL, respectively) as a positive control and showed no growth inhibition activity against the tumor cells HL60 and A549.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Antifungal Agents / chemistry*
  • Antifungal Agents / isolation & purification
  • Antifungal Agents / pharmacology
  • Candida glabrata / drug effects
  • Caulerpa / chemistry*
  • Cell Line, Tumor
  • Cell Proliferation / drug effects
  • Cryptococcus neoformans / drug effects
  • HL-60 Cells
  • Humans
  • Magnetic Resonance Spectroscopy
  • Molecular Conformation
  • Trichophyton / drug effects
  • Xylenes / chemistry*
  • Xylenes / isolation & purification
  • Xylenes / pharmacology

Substances

  • Antifungal Agents
  • Xylenes
  • caulerprenylol A
  • caulerprenylol B