Chacón Morales Pablo A, Amaro-Luis Juan M, Kutateladze Andrei G
Laboratory of Natural Products, Department of Chemistry, Faculty of Sciences, University of "Los Andes" , Mérida 5101, Venezuela.
Department of Chemistry and Biochemistry, University of Denver , Denver, Colorado 80208, United States.
J Nat Prod. 2017 Apr 28;80(4):1210-1214. doi: 10.1021/acs.jnatprod.7b00041. Epub 2017 Mar 30.
Basic hydrolysis of a dichloromethane extract of Stevia lucida yielded (4R,5S,7R,9R,10R,11R)-7,9-dihydroxylongipin-2-en-1-one (1), which was oxidized and subjected to acidic conditions to generate the new seco-moreliane derivative 3. The structure of 3 was established based on NMR data interpretation and confirmed computationally. A plausible mechanism for the carbocationic rearrangement of the trione 2 to the seco-moreliane 3 was supported by DFT computations.
光叶甜菊二氯甲烷提取物的碱性水解产生了(4R,5S,7R,9R,10R,11R)-7,9-二羟基长叶松-2-烯-1-酮(1)，其经氧化并在酸性条件下生成了新的裂环莫雷烷衍生物3。通过核磁共振数据解析确定了3的结构，并经计算得到证实。密度泛函理论计算支持了三酮2向裂环莫雷烷3的碳正离子重排的合理机制。
