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Design, Synthesis and Hepatoprotective Activity of Analogs of the Natural Product Goodyeroside A
State Key Laboratory of Bioactive Substance and Function of Natural Medicines & Beijing Key Laboratory of Active Substances Discovery and Druggability Evaluation, Institute of Materia Medica, Peking Union Medical College and Chinese Academy of Medical Sciences, Beijing 100050, China
Shanghai Institute of Pharmaceutical Industry, Shanghai 200040, China
* Author to whom correspondence should be addressed.
Received: 21 December 2012; in revised form: 29 January 2013 / Accepted: 30 January 2013 / Published: 1 February 2013
Abstract: Goodyeroside A, a natural product isolated from the Goodyera species, possesses significant hepatoprotective activity and has a novel skeleton not previously observed in other synthetic drugs used for the treatment of hepatitis. Herein, we report a highly stereoselective synthesis of goodyeroside A and related analogs with varying substituents at the α position of the carbonyl group to explore the structure-activity relationships of goodyeroside A. The absolute configuration of analog 5d was confirmed by single crystal X-ray analysis. The results from in vitro and in vivo studies indicate that 5a, the fully acetylated compound of goodyeroside A, is worthy of further investigation as a lead to identify novel hepatoprotective agents.
Keywords: goodyeroside A; structure-activity relationships; stereoselective; single crystal X-ray
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MDPI and ACS Style
Zhang, F.; Han, B.; Li, P.; Lin, Z.; Yin, D.; Li, Y.; Zhong, J.; Huang, H. Design, Synthesis and Hepatoprotective Activity of Analogs of the Natural Product Goodyeroside A. Molecules 2013, 18, 1933-1948.
Zhang F, Han B, Li P, Lin Z, Yin D, Li Y, Zhong J, Huang H. Design, Synthesis and Hepatoprotective Activity of Analogs of the Natural Product Goodyeroside A. Molecules. 2013; 18(2):1933-1948.
Zhang, Feng; Han, Bei; Li, Peng; Lin, Ziyun; Yin, Dali; Li, Yan; Zhong, Jialiang; Huang, Haihong. 2013. "Design, Synthesis and Hepatoprotective Activity of Analogs of the Natural Product Goodyeroside A." Molecules 18, no. 2: 1933-1948.