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A Pair of Windmill-Shaped Enantiomers from Lindera aggregata with Activity toward Improvement of Insulin Sensitivity
Fei Wang?§, Yuan Gao§, Ling Zhang?, Bing Bai?, Ya Nan Hu?, Ze Jun Dong?, Qi Wei Zhai*?, Hua Jie Zhu*? and Ji Kai Liu*?
State Key Laboratory of Phytochemistry and Plant Resources in West China, Kunming Institute of Botany, Chinese Academy of Sciences, Kunming 650204, People’s Republic of China, BioBioPha Co. Ltd., Kunming 650204, People’s Republic of China, and Institute for Nutritional Science, Shanghai Institutes for Biological Sciences, Chinese Academy of Sciences, 294 Tai-Yuan Road, Shanghai 200031, People’s Republic of China
(+)-Linderaspirone A and (?)-linderaspirone A, a pair of natural windmill-shaped enantiomers, were isolated from the traditional Chinese medicine plant Lindera aggregate by HPLC using a chiral column, achieving over 98% ee. Their structures and absolute configurations were determined on the basis of extensive analysis of NMR spectra, crystal X-ray diffraction, and calculation of the optical rotations (OR). They have an unprecedented carbon skeleton and showed significant activity against glucosamine-induced insulin resistance.