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Synthesis and Structure Characterization of Bioactive

Polymethoxy Flavonoids Carboxylic Acid and Amino
Acids Derivatives

1,4 2 3 1,2,4,*
LIU Wei ,摇 LI Xueli ,摇 WANG Qiu蒺an ,摇 SHAN Yang
(1. Institute of Agricultural Product Processing, Hunan Academy of Agricultural Science, Changsha 410125, China;
2. Longping Branch Graduate School, Hunan University, Changsha 410125, China;
3. College of Chemistry and Chemical Engineering, Hunan University, Changsha 410082, China;
4. Hunan Key Laboratory of Fruits & Vegetables Storage, Processing and Quality Safety, Changsha 410125, China)

Abstract: Polymethoxy flavonoids (PMFs) are a class natural products, which almost exclusively exist in
citrus plants possessing distinguished anti鄄carcinogenic, anti鄄inflammatory and antioxidative activities. In
order to increase the water solubility and medicinal value of PMFs, tangeretin and nobiletin, the two most
abundant source and the highest anticancer activity of natural polymethoxy flavonoids, were oxidated by
dimethyldioxirane to polymethoxy flavonoids (3鄄hydroxytangerine (7) and 3鄄hydroxynobiletin (8)). The
compound 7 or 8 was reacted with ethyl chloroacetate by Williamson synthesis in anhydrous potassium
carbonate and N, N鄄dimethylformamide. Then the reaction solution was controlled under alkaline
conditions at room temperature for hydrolysis to obtain two polymethoxy flavonoids carboxylic acid
derivatives ( tangerine鄄3鄄O鄄acetic acid (1 ) and nobiletin鄄3鄄O鄄acetic acid ( 2 )) that have not been
reported in the literature. Under the conditions of CH Cl as solvent, EDCI and DMAP as the catalytic
2 2
system, tangerine and nobiletin carboxylic acid derivatives were reacted with glycine methyl ester
hydrochloride and phenylalanine methyl ester hydrochloride respectively and four polymethoxy flavonoids
amino acid methyl ester derivative were obtained. After the hydrolysis treatment, four new polymethoxy
flavonoids amino acid derivatives 3 to 6 were first synthesized. The structure of all synthesized compounds
1 13
were characterized by H NMR, C NMR, and MS.
Keywords: polymethoxy flavonoids; flavonoid carboxylic acid derivatives; flavonoid amino acid
derivatives; synthesis; structure characterization
(责任编辑:李摇 宁)