New bioactive polyphenols from Theobroma grandiflorum ("cupuaçu").
Activity-guided fractionation of Theobroma grandiflorum ("cupuaçu") seeds resulted in the identification of two new sulfated flavonoid glycosides, theograndins I (1) and II (2). In addition, nine known flavonoid antioxidants, (+)-catechin, (-)-epicatechin, isoscutellarein 8-O-beta-d-glucuronide, hypolaetin 8-O-beta-d-glucuronide, quercetin 3-O-beta-d-glucuronide, quercetin 3-O-beta-d-glucuronide 6' '-methyl ester, quercetin, kaempferol, and isoscutellarein 8-O-beta-d-glucuronide 6' '-methyl ester, were identified. Theograndin II (2) displayed antioxidant activity (IC(50) = 120.2 microM) in the 1,1-diphenyl-2-picrylhydrazyl (DPPH) free-radical assay, as well as weak cytotoxicity in the HCT-116 and SW-480 human colon cancer cell lines with IC(50) values of 143 and 125 microM, respectively. While 1 was less active as an antioxidant than 2, the known compounds were more potent in the DPPH assay (IC(50) range 39.7-89.7 microM).
Yang
Hui
H
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.
Protiva
Petr
P
Cui
Baoliang
B
Ma
Cuiying
C
Baggett
Scott
S
Hequet
Vanessa
V
Mori
Scott
S
Weinstein
I Bernard
IB
Kennelly
Edward J
EJ
D000972:Antineoplastic Agents, Phytogenic / Q000737:chemistry / Q000302:isolation & purification* / Q000494:pharmacology; D000975:Antioxidants / Q000737:chemistry / Q000302:isolation & purification* / Q000494:pharmacology; D001713:Biphenyl Compounds; D002392:Catechin / Q000737:chemistry; D003110:Colonic Neoplasms; D004354:Drug Screening Assays, Antitumor; D005419:Flavonoids / Q000737:chemistry / Q000302:isolation & purification* / Q000494:pharmacology; D005616:French Guiana; D006027:Glycosides / Q000737:chemistry / Q000302:isolation & purification* / Q000494:pharmacology; D006801:Humans; D020128:Inhibitory Concentration 50; D019660:Malvaceae / Q000737:chemistry*; D015394:Molecular Structure; D010851:Picrates / Q000494:pharmacology; D012639:Seeds / Q000737:chemistry; D014407:Tumor Cells, Cultured / Q000187:drug effects
D000972:Antineoplastic Agents, Phytogenic; D000975:Antioxidants; D001713:Biphenyl Compounds; D005419:Flavonoids; D006027:Glycosides; D010851:Picrates; C482484:theograndin I; C482485:theograndin II; D002392:Catechin; C004931:1,1-diphenyl-2-picrylhydrazyl