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Xylopiana A, a Dimeric Guaiane with a Case-Shaped Core from Xylopia vielana: Structural Elucidation and Biomimetic
Ya-Long Zhang1, Xu-Wei Zhou1, Xiao-Bing Wang1
1Jiangsu Key Laboratory of Bioactive Natural Product Research and State Key Laboratory of Natural Medicines, China Pharmaceutical University , 24 Tong Jia Xiang, Nanjing 210009, People's Republic of China.
Abstract:
Xylopiana A (1), a dimeric guaiane with an unprecedented pentacyclo[5.2.1.01,2.04,5'.05,4']decane-3,2'-dione core, and three biosynthetically related intermediates, compounds 2-4, were isolated from the leaves of Xylopia vielana. Their structures and absolute configurations were determined by a combination of spectroscopic data, X-ray crystallography, electronic circular dichroism calculations, and chemical conversion. The structure of known vielanin A was revised to be compound 3. Compound 4 exerted a 3.7-fold potentiation effect on doxorubicin susceptibility at the tested concentration of 10 μM.
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