Bioactive novel polyphenols from the fruit of Manilkara zapota (Sapodilla)

J Nat Prod. 2003 Jul;66(7):983-6. doi: 10.1021/np020576x.

Abstract

Activity-guided fractionation of a methanol extract from the fruit of Manilkara zapota cv. Tikal resulted in the isolation of two new antioxidants, methyl 4-O-galloylchlorogenate (1) and 4-O-galloylchlorogenic acid (2), along with eight known polyphenolic antioxidants, namely, methyl chlorogenate (3), dihydromyricetin (4), quercitrin (5), myricitrin (6), (+)-catechin (7), (-)-epicatechin (8), (+)-gallocatechin (9), and gallic acid (10). Of the 10 polyphenols, 1 showed the highest antioxidant activity (IC(50) = 12.9 microM) in the 1,1-diphenyl-2-picrylhydrazyl (DPPH) free-radical assay and displayed cytotoxicity in the HCT-116 and SW-480 human colon cancer cell lines with IC(50) values of 190 and 160 microM, respectively. Compound 2 showed high antioxidant activity (IC(50) = 23.5 microM) in the DPPH free-radical assay and displayed cytotoxicity in the HCT-116 and SW-480 human colon cancer cell lines with IC(50) values of 154 and 134 microM, respectively.

Publication types

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

MeSH terms

  • Antioxidants / chemistry
  • Antioxidants / isolation & purification*
  • Antioxidants / pharmacology
  • Biphenyl Compounds
  • Colonic Neoplasms
  • Drug Screening Assays, Antitumor
  • Flavonoids / chemistry
  • Flavonoids / isolation & purification*
  • Flavonoids / pharmacology
  • Florida
  • Fruit / chemistry
  • Humans
  • Inhibitory Concentration 50
  • Manilkara / chemistry*
  • Molecular Structure
  • Nuclear Magnetic Resonance, Biomolecular
  • Phenols / chemistry
  • Phenols / isolation & purification*
  • Phenols / pharmacology
  • Picrates / pharmacology
  • Polyphenols
  • Stereoisomerism
  • Structure-Activity Relationship
  • Tumor Cells, Cultured / drug effects

Substances

  • Antioxidants
  • Biphenyl Compounds
  • Flavonoids
  • Phenols
  • Picrates
  • Polyphenols
  • 1,1-diphenyl-2-picrylhydrazyl