New cytotoxic cycloartane triterpene from Cassia italica aerial parts

Nat Prod Res. 2014;28(13):976-83. doi: 10.1080/14786419.2014.902820. Epub 2014 Apr 1.

Abstract

Phytochemical study of the aerial parts of Cassiaitalica Mill. (family: Fabaceae) growing in Saudi Arabia afforded one new cycloartane triterpene, named (22E)-3-β-hydroxycycloart-22-en-24-one (2), together with eight known compounds: β-sitosterol (1), uvaol (3), daucosterol (4), methyl 3,4-dihydroxybenzoate (5), emodin (6), 4-hydroxypheny-O-β-D-glucopyranoside (7), aloin (8) and rutin (9). The structure of the isolated compounds was determined by physical, chemical and spectral data (UV, IR, MS, 1D ((1)H, (13)C and DEPT) and 2D ((1)H-(1)H COSY, HSQC and HMBC) NMR), as well as by comparing with authentic samples. Compounds 3-5 and 7-9 were isolated for the first time from the plant. Compound 2 was evaluated for its cytotoxic activity against the L5178Y and PC12 cell lines. The total methanolic extract and compounds 5-9 exhibited free radical-scavenging activity using DPPH assay.

Keywords: Cassia italic; anthraquinones; antioxidant; cycloartane; cytotoxicity; phenolics.

MeSH terms

  • Algorithms
  • Animals
  • Biphenyl Compounds / pharmacology
  • Cassia / chemistry*
  • Free Radical Scavengers / chemistry
  • Free Radical Scavengers / isolation & purification*
  • Free Radical Scavengers / pharmacology*
  • Humans
  • Hydroxybenzoates / chemistry
  • Nuclear Magnetic Resonance, Biomolecular
  • PC12 Cells
  • Picrates / pharmacology
  • Rats
  • Saudi Arabia
  • Sitosterols / chemistry
  • Triterpenes / chemistry
  • Triterpenes / isolation & purification*
  • Triterpenes / pharmacology*

Substances

  • (22E)-3-beta-hydroxycycloart-22-en-24-one
  • 3,4-dihydroxybenzoate
  • Biphenyl Compounds
  • Free Radical Scavengers
  • Hydroxybenzoates
  • Picrates
  • Sitosterols
  • Triterpenes
  • cycloartane
  • gamma-sitosterol
  • 1,1-diphenyl-2-picrylhydrazyl
  • uvaol