Novel Chemical Synthesis of Ginkgolic Acid (13:0) and Evaluation of Its Tyrosinase Inhibitory Activity

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• 作者：Yuanqing Fu ; Shan Hong ; Duo Li ; Songbai Liu
• 刊名：Journal of Agricultural and Food Chemistry
• 出版年：2013
• 出版时间：June 5, 2013
• 年：2013
• 卷：61
• 期：22
• 页码：5347-5352
• 全文大小：347K
• 年卷期：v.61,no.22(June 5, 2013)
• ISSN：1520-5118

文摘

A novel efficient synthesis of ginkgolic acid (13:0) from abundant 2,6-dihydroxybenzoic acid was successfully developed through a state-of-the-art palladium-catalyzed cross-coupling reaction and catalytic hydrogenation with an overall yield of 34% in five steps. The identity of the synthesized ginkgolic acid (13:0) was confirmed by nuclear magnetic resonance, mass spectrometry, infrared, and high-performance liquid chromatography. The reaction sequence of this method can be readily extended to the synthesis of other ginkgolic acids. The synthesized ginkgolic acid (13:0) exhibited promising anti-tyrosinase activity (IC₅₀ = 2.8 mg/mL) that was not correlated to antioxidant activity as probed by 1,1-diphenyl-2-picrylhydrazyl, 2,2鈥?azino-bis(3-ethylbenzothiazoline-6-sulfonic acid), ferric reducing ability of plasma, and oxygen radical absorbance capacity assays. The synthetic strategy developed in this work will significantly facilitate biological studies of ginkgolic acids that have great potential applications in food and pharmaceuticals.

Keywords:

Ginkgolic acid; synthesis; tyrosinase inbibitory activity; cross-coupling reaction; antioxidant activity