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]

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.

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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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