Bioactive novel polyphenols from the fruit of Manilkara zapota (Sapodilla).
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.
Ma
Jun
J
Department of Biological Sciences, Lehman College and The Graduate Center, The City University of New York, 250 Bedford Park Boulevard West, Bronx, New York 10468, USA.
Luo
Xiao-Dong
XD
Protiva
Petr
P
Yang
Hui
H
Ma
Cuiying
C
Basile
Margaret J
MJ
Weinstein
I Bernard
IB
Kennelly
Edward J
EJ
D000975:Antioxidants / Q000737:chemistry / Q000302:isolation & purification* / Q000494:pharmacology; D001713:Biphenyl Compounds; D003110:Colonic Neoplasms; D004354:Drug Screening Assays, Antitumor; D005419:Flavonoids / Q000737:chemistry / Q000302:isolation & purification* / Q000494:pharmacology; D005431:Florida; D005638:Fruit / Q000737:chemistry; D006801:Humans; D020128:Inhibitory Concentration 50; D032129:Manilkara / Q000737:chemistry*; D015394:Molecular Structure; D019906:Nuclear Magnetic Resonance, Biomolecular; D010636:Phenols / Q000737:chemistry / Q000302:isolation & purification* / Q000494:pharmacology; D010851:Picrates / Q000494:pharmacology; D059808:Polyphenols; D013237:Stereoisomerism; D013329:Structure-Activity Relationship; D014407:Tumor Cells, Cultured / Q000187:drug effects
D000975:Antioxidants; D001713:Biphenyl Compounds; D005419:Flavonoids; D010636:Phenols; D010851:Picrates; D059808:Polyphenols; C004931:1,1-diphenyl-2-picrylhydrazyl