Puupehanol, a sesquiterpene-dihydroquinone derivative from the marine sponge Hyrtios sp

Bioorg Med Chem Lett. 2009 Nov 1;19(21):6140-3. doi: 10.1016/j.bmcl.2009.09.015. Epub 2009 Sep 11.

Abstract

Puupehanol (1), a new sesquiterpene-dihydroquinone derivative, was isolated from the marine sponge Hyrtios sp., along with the known compounds puupehenone (2) and chloropuupehenone (3) that are responsible for the antifungal activity observed in the extract. The structure of 1 was established as (20R,21R)-21-hydroxy-20,21-dihydropuupehenone by extensive spectroscopic and computational methods. Compound 2 exhibited potent activity against Cryptococcus neoformans and Candida krusei with MFCs of 1.25 and 2.50 microg/mL, respectively.

Publication types

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

MeSH terms

  • Animals
  • Antifungal Agents / chemistry*
  • Antifungal Agents / isolation & purification
  • Antifungal Agents / pharmacology
  • Benzopyrans / chemistry*
  • Benzopyrans / isolation & purification
  • Benzopyrans / pharmacology
  • Cyclohexanones / chemistry*
  • Cyclohexanones / isolation & purification
  • Cyclohexanones / pharmacology
  • Heterocyclic Compounds, 4 or More Rings / chemistry
  • Heterocyclic Compounds, 4 or More Rings / isolation & purification
  • Heterocyclic Compounds, 4 or More Rings / pharmacology
  • Magnetic Resonance Spectroscopy
  • Microbial Sensitivity Tests
  • Molecular Conformation
  • Porifera / chemistry*
  • Pyrans / chemistry
  • Pyrans / isolation & purification
  • Pyrans / pharmacology
  • Quinones / chemistry*
  • Quinones / isolation & purification
  • Quinones / pharmacology
  • Sesquiterpenes / chemistry*
  • Sesquiterpenes / isolation & purification
  • Sesquiterpenes / pharmacology
  • Xanthones / chemistry
  • Xanthones / isolation & purification
  • Xanthones / pharmacology

Substances

  • 1,4-dihydroquinone
  • Antifungal Agents
  • Benzopyrans
  • Cyclohexanones
  • Heterocyclic Compounds, 4 or More Rings
  • Pyrans
  • Quinones
  • Sesquiterpenes
  • Xanthones
  • chloropuupehenone
  • puupehanol
  • puupehenone