Constitutive phenolics of Harpephyllum caffrum (Anacardiaceae) and their biological effects on human keratinocytes

Fitoterapia. 2011 Dec;82(8):1265-71. doi: 10.1016/j.fitote.2011.08.014. Epub 2011 Aug 31.

Abstract

Assessment of the UV protecting potential of an aqueous methanol leaf extract of Harpephyllum caffrum proved that it possesses a distinct radical scavenging effect and inhibits the production of the proinflammatory cytokine IL-6 by human keratinocytes (HaCaT cells) following UV radiation. Phytochemical investigation of this extract led to isolation and structural determination of the hitherto unknown phenolics, kaempferol 3-O-(2″-sulphatogalactopyranoside), its quercetin analogue and 3-methoxyellagic acid 4-O-galactopyranoside in addition to 18 known phenolic compounds. The structures were determined by spectroscopic and conventional methods of analysis. Flavonoid sulphatoglycosides which have been rarely found in nature were major phenolic constituents of this plant, and this is the first report of the isolation of any of them from Anacardiaceae. The extract was found to diminish UV phototoxic reaction of keratinocytes. However, the isolated kaempferol sulphatogalactopyranoside did not interact with UVB triggered IL-6 production of HaCaT keratinocytes.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Anacardiaceae / chemistry*
  • Anti-Inflammatory Agents / isolation & purification
  • Anti-Inflammatory Agents / pharmacology*
  • Antioxidants / isolation & purification
  • Antioxidants / pharmacology*
  • Cells, Cultured
  • Dermatitis, Phototoxic / drug therapy
  • Dermatitis, Phototoxic / metabolism
  • Dermatologic Agents / isolation & purification
  • Dermatologic Agents / pharmacology
  • Ellagic Acid / analogs & derivatives*
  • Ellagic Acid / isolation & purification
  • Ellagic Acid / pharmacology
  • Free Radical Scavengers / isolation & purification
  • Free Radical Scavengers / pharmacology
  • Galactosides / isolation & purification
  • Galactosides / pharmacology*
  • Humans
  • Interleukin-6 / biosynthesis
  • Kaempferols / isolation & purification
  • Kaempferols / pharmacology*
  • Keratinocytes / drug effects*
  • Keratinocytes / metabolism
  • Keratinocytes / radiation effects
  • Molecular Structure
  • Plant Extracts / chemistry
  • Plant Extracts / pharmacology*
  • Plant Leaves
  • Polyphenols / isolation & purification
  • Polyphenols / pharmacology
  • Quercetin / isolation & purification
  • Quercetin / pharmacology
  • Ultraviolet Rays / adverse effects

Substances

  • 3-methoxyellagic acid 4-O-galactopyranoside
  • Anti-Inflammatory Agents
  • Antioxidants
  • Dermatologic Agents
  • Free Radical Scavengers
  • Galactosides
  • Interleukin-6
  • Kaempferols
  • Plant Extracts
  • Polyphenols
  • kaempferol 3-O-(2''-sulfatogalactopyranoside)
  • Ellagic Acid
  • Quercetin