Abstract
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).
Publication types
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Research Support, Non-U.S. Gov't
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Research Support, U.S. Gov't, P.H.S.
MeSH terms
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Antineoplastic Agents, Phytogenic / chemistry
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Antineoplastic Agents, Phytogenic / isolation & purification*
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Antineoplastic Agents, Phytogenic / pharmacology
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Antioxidants / chemistry
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Antioxidants / isolation & purification*
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Antioxidants / pharmacology
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Biphenyl Compounds
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Catechin / chemistry
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Colonic Neoplasms
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Drug Screening Assays, Antitumor
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Flavonoids / chemistry
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Flavonoids / isolation & purification*
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Flavonoids / pharmacology
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French Guiana
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Glycosides / chemistry
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Glycosides / isolation & purification*
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Glycosides / pharmacology
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Humans
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Inhibitory Concentration 50
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Malvaceae / chemistry*
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Molecular Structure
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Picrates / pharmacology
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Seeds / chemistry
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Tumor Cells, Cultured / drug effects
Substances
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Antineoplastic Agents, Phytogenic
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Antioxidants
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Biphenyl Compounds
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Flavonoids
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Glycosides
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Picrates
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theograndin I
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theograndin II
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Catechin
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1,1-diphenyl-2-picrylhydrazyl