Geranins A and B, new antiprotozoal A-type proanthocyanidins from Geranium niveum

J Nat Prod. 1999 May;62(5):705-9. doi: 10.1021/np980467b.

Abstract

Bioassay-guided fractionation of the antiprotozoal extract of Geranium niveum led to the isolation of two new A-type proanthocyanidins, epi-afzelechin-(4beta-->8, 2beta-->O-->7)-afzelechin (1) and epi-catechin-(4beta-->8, 2beta-->O-->7)-afzelechin (2). Compounds 1 and 2 were given the trivial names of geranins A and B, respectively. In addition, five known compounds, mahuannin B (3), reynoutrin (4), hyperin (5), methyl gallate (6), and 3-beta-caffeoyl-12-oleanen-28-oic acid (7), were obtained. The structures of the new proanthocyanidins were elucidated by spectroscopic and chemical methods as well as CD measurements. Compounds 1, 2, and 4-7 were tested against axenically grown trophozoites of Giardia lamblia and Entamoeba histolytica.

Publication types

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

MeSH terms

  • Animals
  • Anthocyanins / isolation & purification
  • Anthocyanins / pharmacology*
  • Antineoplastic Agents, Phytogenic / isolation & purification
  • Antineoplastic Agents, Phytogenic / pharmacology
  • Antiprotozoal Agents / isolation & purification
  • Antiprotozoal Agents / pharmacology*
  • Drug Screening Assays, Antitumor
  • Entamoeba histolytica / drug effects
  • Giardia lamblia / drug effects
  • Humans
  • Magnetic Resonance Spectroscopy
  • Magnoliopsida / chemistry*
  • Mexico
  • Models, Molecular
  • Molecular Conformation
  • Plant Roots / chemistry
  • Proanthocyanidins*
  • Spectrometry, Mass, Fast Atom Bombardment
  • Tumor Cells, Cultured

Substances

  • Anthocyanins
  • Antineoplastic Agents, Phytogenic
  • Antiprotozoal Agents
  • Proanthocyanidins
  • geranin A
  • geranin B