Chromenes of polyketide origin from Peperomia villipetiola

Phytochemistry. 2005 Mar;66(5):573-9. doi: 10.1016/j.phytochem.2005.01.003.

Abstract

An extract of leaves and stems of Peperomia villipetiola has been found to contain myristicin (3-methoxy-4,5-methylenedioxy-allylbenzene) and seven chromenes, whose structures are methyl 5-hydroxy-7-methyl-2,2-dimethyl-2H-1-chromene-6-carboxylate (1), methyl 5-methoxy-7-methyl-2,2-dimethyl-2H-1-chromene-8-carboxylate (2), methyl 7-hydroxy-5-methyl-2,2-dimethyl-2H-1-chromene-6-carboxylate (3), methyl 7-methoxy-5-methyl-2,2-dimethyl-2H-1-chromene-6-carboxylate (4), 5-methanol-7-hydroxy-2,2-dimethyl-2H-1-chromene-6-carboxylic acid (5), 5-methanol-7-methoxy-2,2-dimethyl-2H-1-chromene-6-carboxylic acid (6), and methyl 5-acetoxymethanol-7-hydroxy-2,2-dimethyl-2H-1-chromene-6-carboxylate (7). A biosynthetic rationale for 1-7 suggests that orsellinic acid may be a common intermediate. The anti-fungal activities of the chromenes were measured bioautographically against Cladosporium cladosporioides and Cladosporium sphaerospermum: compounds 6 and 7 were found to be the most active.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Benzopyrans / chemistry*
  • Benzopyrans / isolation & purification
  • Macrolides / chemistry*
  • Macrolides / isolation & purification
  • Magnetic Resonance Spectroscopy
  • Models, Molecular
  • Molecular Conformation
  • Peperomia / chemistry*
  • Plant Extracts / chemistry*
  • Plant Extracts / isolation & purification
  • Plant Leaves / chemistry
  • Plant Stems / chemistry
  • Spectrophotometry, Infrared

Substances

  • Benzopyrans
  • Macrolides
  • Plant Extracts