Antiophidic solanidane steroidal alkaloids from Solanum campaniforme

J Nat Prod. 2011 Oct 28;74(10):2168-73. doi: 10.1021/np200479a. Epub 2011 Sep 30.

Abstract

Three new solanidane alkaloids bearing a 22,23-epoxy ring (1-3) and four known compounds were isolated from leaves of Solanum campaniforme. The structures were determined using spectroscopic techniques, including 1D and 2D NMR, and HRESIMS experiments. The antiophidic activity of the alkaloids was tested against Bothrops pauloensis venom. Compounds 1-3 completely inhibited myotoxicity without inhibiting phospholipase A2 activity of the venom, while hemorrhage and skin necrosis were significantly reduced in the presence of alkaloids 1 and 2.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Alkaloids / chemistry
  • Alkaloids / immunology
  • Alkaloids / isolation & purification*
  • Alkaloids / pharmacology*
  • Animals
  • Bothrops / physiology
  • Brazil
  • Crotalid Venoms / blood
  • Crotalid Venoms / metabolism
  • Crotalid Venoms / toxicity*
  • Molecular Structure
  • Nuclear Magnetic Resonance, Biomolecular
  • Plant Leaves / chemistry
  • Solanum / chemistry*
  • Steroids / chemistry
  • Steroids / isolation & purification*
  • Steroids / pharmacology*

Substances

  • 22alpha,23alpha-epoxy-solanida-1,4,9-trien-3-one
  • 22alpha,23alpha-epoxy-solanida-1,4-dien-3-one
  • 3,9beta-hydroxy-22alpha,23alpha-epoxy-9(10)-seco-solanida-1,3,5(10)-triene
  • Alkaloids
  • Crotalid Venoms
  • Steroids