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Paper | Regular issue | Vol 81, No. 11, 2010, pp.2497-2509
Published online, 13th September, 2010
DOI: 10.3987/COM-10-12002
UNIQUE PHENYL ETHER TYPE BIFLAVONOIDS, ZIZYFLAVOSIDES A AND B WITH BIOMIMETIC SYNTHESIS FOR ZIZYFLAVOSIDE A

Mahmoud Mostafa,* Fumihide Takano, and Tomihisa Ohta*

*Department of Pharmacognosy and Chemistry of Natural Products, Graduate School of Natural Science and Technology, Kanazawa University, Kakuma, Kanazawa, Ishikawa 920-1192, Japan

Abstract

During our investigation of Zizyphus spina-christi (L.) Willd. leaves for anti-inflammatory activity, eight compounds were characterized. Two are new phenyl ether type biflavonoids, which were assigned as zizyflavosides A (1) and B (2). The structures of 1 and 2 were determined by spectroscopic analyses including 1D, 2D NMR and MS spectroscopic and chemical data. The other isolated compounds were known flavonoids kaempferol-3-O-rutinoside (5), quercetin-3-O-rutinoside (6), 3',5'-di-C-β-D-glucosylphloretine (7), quercetin-3-O-[β-D-xylosyl-(12)-α-L-rhamnoside]-4'-O-α-L-rhamnoside (8), epiafzelechin (9) and quercetin-3-O-[β-D-xylosyl-(12)-α-L-rhamnoside] (10). Zizyflavoside A was synthesized from quercetin-3-O-rutinoside and kaempferol-3-O-rutinoside using laccase as an enzyme and this biomimetic synthesis could be indication to its biosynthetic pathway.