Identification and antiradical properties of anthocyanins in fruits of Viburnum dilatatum thunb.
The fruit of Viburnum dilatatum Thunb., called gamazumi, has been shown to prevent oxidative injury in rats given gamazumi crude extract (GCE). Therefore, phenolic compounds in GCE were purified by Sephadex LH-20 column chromatography and preparative high-performance liquid chromatography. Two major anthocyanins were isolated, and their structures were determined by NMR, liquid chromatography/electrospray ionization mass spectrometry/MS and sugar analysis as cyanidin 3-O-(2-O-beta-D-xylopyranosyl)-beta-D-glucopyranoside, namely, cyanidin 3-sambubioside (I) and that of cyanidin 3-O-beta-D-glucopyranoside, namely, kuromanin (II). This is the first identification of these compounds in V. dilatatum fruits, which contain I and II at 141.3 and 4.5 microg/g of fresh fruit, respectively. By the electron spin resonance method, the superoxide anion radical scavenging activities (IC(50)) of I and II were 17.3 and 69.6 microM, and their activities on hydroxyl radicals were 4.3 and 53.2 mM. As a positive control, the activities of ascorbic acid were 74.2 microM on superoxide anion radicals and 3.0 mM on hydroxyl radicals. Our results suggest that these anthocyanins having radical scavenging properties may be key compounds contributing to the antioxidant activity and physiological effects of V. dilatatum fruits.
D000872:Anthocyanins / Q000032:analysis* / Q000494:pharmacology; D000975:Antioxidants / Q000032:analysis*; D002241:Carbohydrates / Q000032:analysis; D002851:Chromatography, High Pressure Liquid; D016166:Free Radical Scavengers / Q000032:analysis* / Q000494:pharmacology; D005638:Fruit / Q000737:chemistry*; D005960:Glucosides / Q000032:analysis* / Q000494:pharmacology*; D017665:Hydroxyl Radical; D010936:Plant Extracts / Q000737:chemistry / Q000494:pharmacology; D021241:Spectrometry, Mass, Electrospray Ionization; D013481:Superoxides; D027925:Viburnum / Q000737:chemistry*
D000872:Anthocyanins; D000975:Antioxidants; D002241:Carbohydrates; D016166:Free Radical Scavengers; D005960:Glucosides; D010936:Plant Extracts; C000596494:cyanidin 3-O-glucopyranoside; D013481:Superoxides; D017665:Hydroxyl Radical