Dihydrochalcones from Piper longicaudatum

Planta Med. 2001 Mar;67(2):186-8. doi: 10.1055/s-2001-11517.

Abstract

Bioactivity-guided fractionation of an ethanolic extract of the leaves and twigs of Piper longicaudatum Trelease & Yunker (Piperaceae) resulted in the isolation of one new (1) and three known (2-4) dihydrochalcones. The known compounds are: 2',6'-dihydroxy-4'-methoxydihydrochalcone (2), 2',6',4-trihydroxy-4'-methoxydihydrochalcone (asebogenin) (3), and 2'-hydroxy-4'-methoxy-2'-[1-hydroxy-1-methylethyl]-2",3"-dihy- drofurano[4",5":5',6"]-3"-[2-hydroxy-5-methoxycarbonylphe- nyl]dihydrochalcone (piperaduncin B) (4). The new compound is 2'-hydroxy-4'-methoxy-2"-[2-hydroxy-5-methoxycarbonyl- phenyl]-furano[4",5":5',6']-dihydrochalcone (longicaudatin) (1). Compounds 1-4 were tested for antibacterial activity against S. aureus and methicillin-resistant S. aureus (MRSA); only compound 3 showed inhibitory activity (IC50 of 10 and 4.5 micrograms/ml, respectively).

Publication types

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

MeSH terms

  • Alkaloids / isolation & purification*
  • Alkaloids / pharmacology
  • Anti-Bacterial Agents / isolation & purification*
  • Anti-Bacterial Agents / pharmacology
  • Chalcone / analogs & derivatives*
  • Chalcone / isolation & purification*
  • Chalcone / pharmacology
  • Chalcones
  • Molecular Structure
  • Plant Leaves / chemistry
  • Plant Stems / chemistry
  • Plants, Medicinal / chemistry*
  • Staphylococcus aureus / drug effects

Substances

  • 2',6'-dihydroxy-4'-methoxydihydrochalcone
  • Alkaloids
  • Anti-Bacterial Agents
  • Chalcones
  • asebogenin
  • piperaduncin B
  • Chalcone
  • longicautadine
  • dihydrochalcone