Triterpene Glycosides and Other Polar Constituents of Shea (Vitellaria Paradoxa) Kernels and Their Bioactivities

Phytochemistry. 2014 Dec;108:157-70. doi: 10.1016/j.phytochem.2014.09.017. Epub 2014 Oct 21.

Abstract

The MeOH extract of defatted shea (Vitellaria paradoxa; Sapotaceae) kernels was investigated for its constituents, and fifteen oleanane-type triterpene acids and glycosides, two steroid glucosides, two pentane-2,4-diol glucosides, seven phenolic compounds, and three sugars, were isolated. The structures of five triterpene glycosides were elucidated on the basis of spectroscopic and chemical methods. Upon evaluation of the bioactivity of the isolated compounds, it was found that some or most of the compounds have potent or moderate inhibitory activities against the following: melanogenesis in B16 melanoma cells induced by α-melanocyte-stimulating hormone (α-MSH); generation of 1,1-diphenyl-2-picrylhydrazyl (DPPH) radicals, against Epstein-Barr virus early antigen (EBV-EA) activation induced by 12-O-teradecanoylphorbol 13-acetate (TPA) in Raji cells; t TPA-induced inflammation in mice, and proliferation of one or more of HL-60, A549, AZ521, and SK-BR-3 human cancer cell lines, respectively. Western blot analysis established that paradoxoside E inhibits melanogenesis by regulation of expression of microphthalmia-associated transcription factor (MITF), tyrosinase, and tyrosinase-related protein-1 (TRP-1) and TRP-2. In addition, tieghemelin A was demonstrated to exhibit cytotoxic activity against A549 cells (IC50 13.5 μM) mainly due to induction of apoptosis by flow cytometry. The extract of defatted shea kernels and its constituents may be, therefore, valuable as potential antioxidant, anti-inflammatory, skin-whitening, chemopreventive, and anticancer agents.

Keywords: Anti-inflammatory activity; Antioxidant activity; Cytotoxic activity; Epstein–Barr virus early antigen (EBV-EA); Melanogenesis-inhibitory activity; Oleanane-type triterpene glycoside; Sapotaceae; Shea butter; Shea kernel; Vitellaria paradoxa.

MeSH terms

  • Animals
  • Antigens, Viral / drug effects
  • Biphenyl Compounds / pharmacology
  • Glycosides / chemistry
  • Glycosides / isolation & purification*
  • Glycosides / pharmacology*
  • HL-60 Cells
  • Humans
  • Melanins / antagonists & inhibitors
  • Mice
  • Molecular Structure
  • Monophenol Monooxygenase / antagonists & inhibitors
  • Nuclear Magnetic Resonance, Biomolecular
  • Oleanolic Acid / analogs & derivatives
  • Oleanolic Acid / pharmacology
  • Oxidoreductases
  • Picrates / pharmacology
  • Saponins / pharmacology
  • Sapotaceae / chemistry*
  • Seeds / chemistry
  • Triterpenes / chemistry
  • Triterpenes / isolation & purification*
  • Triterpenes / pharmacology*
  • alpha-MSH / drug effects

Substances

  • Antigens, Viral
  • Biphenyl Compounds
  • Epstein-Barr virus early antigen
  • Glycosides
  • Melanins
  • Picrates
  • Saponins
  • Triterpenes
  • tieghemelin
  • alpha-MSH
  • Oleanolic Acid
  • 1,1-diphenyl-2-picrylhydrazyl
  • Oxidoreductases
  • tyrosinase-related protein-1
  • Monophenol Monooxygenase