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Journal of Asian Natural Products Research Volume 15, 2013 - Issue 1
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The resolution of aglinin A epimers and their NMR assignments

Tian-Xiang Feng State Key Laboratory of Microbial Metabolism, School of Life Sciences and Biotechnology, Shanghai Jiao Tong University, Shanghai, 200030, China; Department of Natural Medicinal Chemistry, Shanghai Institute of Materia Medica, Chinese Academy of Sciences, Shanghai, 201203, China
,
Shi-Jin Qu Department of Natural Medicinal Chemistry, Shanghai Institute of Materia Medica, Chinese Academy of Sciences, Shanghai, 201203, China
,
Jun-Jie Tan Department of Natural Medicinal Chemistry, Shanghai Institute of Materia Medica, Chinese Academy of Sciences, Shanghai, 201203, China
,
Kun Jiang Department of Natural Medicinal Chemistry, Shanghai Institute of Materia Medica, Chinese Academy of Sciences, Shanghai, 201203, China
,
Chang-Heng Tan Department of Natural Medicinal Chemistry, Shanghai Institute of Materia Medica, Chinese Academy of Sciences, Shanghai, 201203, ChinaCorrespondence[email protected]
&
Shuang-Jun Lin State Key Laboratory of Microbial Metabolism, School of Life Sciences and Biotechnology, Shanghai Jiao Tong University, Shanghai, 200030, ChinaCorrespondence[email protected]
Pages 89-93 | Received 23 May 2012, Accepted 30 Oct 2012, Published online: 17 Jan 2013
 
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Abstract

Aglinin A (1) is a mixture of C24-epimeric 20S,24-epoxy-24,25-dihydroxy-3,4-secodammar-4(28)-en-3-oic acid and present in plants of the family Meliaceae. The two epimers of 1 were resolved through an acetonide reaction, and the absolute configurations of two derivatives were deduced by the analysis of their 13C NMR differences induced by γ-gauche or steric effect. Based on it, the 13C NMR assignment of 24R-1 and 24S-1 was also established.

Acknowledgements

This study was financially supported by grants from the National Science & Technology Major Project “Key New Drug Creation and Manufacturing Program” (No. 2011ZX09307-002-03) and the National Natural Science Foundation of China (Nos. 81072545 and 21202182).

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