Determination of atropisomeric configurations of macrocyclic bisbibenzyls by HPLC CDUV and quantum chemical calculations高效液相色谱紫外可见分光光度法和量子化学计算确定大环双联苄的阻转异构构型.pdfVIP

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Determination of atropisomeric configurations of macrocyclic bisbibenzyls by HPLC CDUV and quantum chemical calculations高效液相色谱紫外可见分光光度法和量子化学计算确定大环双联苄的阻转异构构型.pdf

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Journal of Asian Natural Products Research Vol. 13, No. 4, April 2011, 312–318 Determination of atropisomeric conﬁgurations of macrocyclic bisbibenzyls by HPLC-CD/UV and quantum chemical calculations Li-Ning Wang, Chun-Feng Xie, Xiao-Song Zhu, Pei-Hong Fan and Hong-Xiang Lou* School of Pharmaceutical Sciences, Shandong University, Jinan 250012, China (Received 8 November 2010; ﬁnal version received 13 January 2011) Isoriccardin C (1) and riccardin D (2), isolated from the liverwort Reboulia hemisphaerica, were ﬁrst characterized to be a mixture of two enantiomeric atropisomers by online chiral high-performance liquid chromatography-circular dichroism (HPLC-CD) analysis. Exemplarily for bisbibenzyls of the diarylether- biphenyl type, the absolute atropisomeric conﬁgurations of compunds 1 and 2 were determined by the analysis of their CD data coupled with quantum chemical CD calculations. Keywords: Reboulia hemisphaerica ; atropisomer; bisbibenzyls; online HPLC-CD; quantum chemical CD calculations 1. Introduction In ongoing studies on the biologically Macrocyclic bisbibenzyls are unique active bisbibenzyls from liverworts metabolites detected mainly in liverwort [2,11,12], we found that the type III species and found to have antifungal, structures, when ortho-hydroxyl(s) anticancer, antioxidant, antiplatelet aggre- occurred at the biphenyl linkage, were gation, antibacterial, and antiviral activi- also optically active. Here, we ﬁrst report ties [1 – 4]. Their structures can be the characterization and assignment of the subdivided into four groups according to absolute conﬁgura