Structural Similarity in Natural Products Leading to Sample Misidentification: A Case Study of the Bisbenzylisoquinoline Alkaloids Oxyacanthine and Berbamine
Cheng YanUniversity of Chinese Academy of Sciences, Beijing 100049, P.R. ChinaDavlat Kh. AkramovInstitute of Biochemistry, Samarkand State University, Samarkand city 140104, UzbekistanLola J. YakhshilikovaInstitute of Biochemistry, Samarkand State University, Samarkand city 140104, UzbekistanChengwei ZhuJie LuState Key Laboratory of Drug Research, Shanghai Institute of Materia Medica, Chinese Academy of Sciences, Shanghai 201203, P.R. ChinaJin SuoState Key Laboratory of Drug Research, Shanghai Institute of Materia Medica, Chinese Academy of Sciences, Shanghai 201203, P.R. ChinaSanthosh PugazhState Key Laboratory of Drug Research, Shanghai Institute of Materia Medica, Chinese Academy of Sciences, Shanghai 201203, P.R. ChinaHongjian QinState Key Laboratory Basis of Xinjiang Indigenous Medicinal Plants Resource Utilization, Key Laboratory of Plant Resources and Chemistry of Arid Zone, Xinjiang Technical Institute of Physics and Chemistry, Chinese Academy of Sciences, Urumqi 830011, P.R. ChinaSafomuddin AbduahadiState Key Laboratory of Drug Research, Shanghai Institute of Materia Medica, Chinese Academy of Sciences, Shanghai 201203, P.R. ChinaJishan QinState Key Laboratory of Drug Research, Shanghai Institute of Materia Medica, Chinese Academy of Sciences, Shanghai 201203, P.R. ChinaTianwen HuJingshan ShenState Key Laboratory of Drug Research, Shanghai Institute of Materia Medica, Chinese Academy of Sciences, Shanghai 201203, P.R. ChinaFeipu YangState Key Laboratory of Drug Research, Shanghai Institute of Materia Medica, Chinese Academy of Sciences, Shanghai 201203, P.R. ChinaHaji Akber AisaSchool of Pharmacy, Xinjiang Medical University, Urumqi 830054, P.R. China
ABI
Abstract
The similar structures of natural compounds and the absence of NMR data for commercial products raise the risk of misidentification. This work reports a case in which purchased samples labeled as “berbamine” from 14 suppliers are oxyacanthine (1). The NMR data of all purchased samples were consistent. The X-ray crystallography characterization of one sample revealed it to be 1. The NMR data of 1 were fully assigned for the first time. Berbamine (2) was isolated from the roots of Berberis sieboldii Miq. The NMR data of 2 were assigned, and its crystal structure was reported for the first time. The authors intend to raise awareness and support the academic/industrial community through a study of this misidentification case.