Proanthocyanidin glycosides and related polyphenols from cacao liquor and their antioxidant effects

• Published in: Phytochemistry (Oxford) 2002-04, Vol.59 (7), p.749-758
• Main Authors: Hatano, Tsutomu, Miyatake, Haruka, Natsume, Midori, Osakabe, Naomi, Takizawa, Toshio, Ito, Hideyuki, Yoshida, Takashi
• Format: Article
• Language: English
• Subjects: Animals; Anthocyanins - chemistry; Anthocyanins - isolation & purification; Anthocyanins - pharmacology; Antioxidant; Antioxidants - chemistry; Antioxidants - isolation & purification; Antioxidants - pharmacology; Biological and medical sciences; Cacao - chemistry; Cacao liquor; Flavonoids - chemistry; Flavonoids - isolation & purification; Food industries; Free Radical Scavengers - chemistry; Free Radical Scavengers - isolation & purification; Free Radical Scavengers - pharmacology; Fundamental and applied biological sciences. Psychology; Glycosides - chemistry; Linoleic Acid - metabolism; Lipid peroxidation; Lipid Peroxidation - drug effects; Lipid Peroxidation - physiology; Microsomes, Liver - drug effects; Microsomes, Liver - metabolism; Oxidation-Reduction - drug effects; Phenols - chemistry; Phenols - isolation & purification; Phenols - pharmacology; Plant Extracts - chemistry; Polymers - chemistry; Polymers - isolation & purification; Polymers - pharmacology; Polyphenol; Proanthocyanidin glycosides; Proanthocyanidins; Radical scavenger; Rats; Research and development. New food products, dietetic foods and beverages; Sterculiaceae; Tannin; Theobroma cacao
• ISSN: 0031-9422; 1873-3700
• DOI: 10.1016/S0031-9422(02)00051-1

Purification of polar fractions from cacao liquor extracts gave 17 phenolics including four new compounds. The new compounds were characterized as a C-glycosidic flavan, an O-glycoside of a dimeric and two O-glycosides of trimeric A-linked proanthocyanidins, on the basis of spectroscopic data. Isolated polyphenols showed inhibitory effects on nicotinamide adenine dinucleotide phosphate-dependent lipid peroxidation in microsomes and on the autoxidation of linoleic acid. These effects were attributed to the radical-scavenging activity in the peroxidation chain reactions, based on the findings that the cacao polyphenols effectively scavenged the 1,1-diphenyl-2-picrylhydrazyl radical. Structures of four monomeric and oligomeric flavan glycosides were elucidated, and antioxidant effects of cacao polyphenols were shown.