Yan Cheng, Davlat Akramov, Lola Yakhshilikova, Chengwei Zhu, Jie Lu, Jin Suo, Santhosh Pugazh, Hongjian Qin, Safomuddin Abduahadi, Jishan Qin, Tianwen Hu, Jingshan Shen, Feipu Yang, Haji A Aisa
{"title":"天然产物结构相似性导致样品错误鉴定：以双苄基异喹啉生物碱氧棘嘌呤和小檗碱为例。","authors":"Yan Cheng, Davlat Akramov, Lola Yakhshilikova, Chengwei Zhu, Jie Lu, Jin Suo, Santhosh Pugazh, Hongjian Qin, Safomuddin Abduahadi, Jishan Qin, Tianwen Hu, Jingshan Shen, Feipu Yang, Haji A Aisa","doi":"10.1021/acs.jnatprod.4c01109","DOIUrl":null,"url":null,"abstract":"<p><p>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 (<b>1</b>). The NMR data of all purchased samples were consistent. The X-ray crystallography characterization of one sample revealed it to be <b>1</b>. The NMR data of <b>1</b> were fully assigned for the first time. Berbamine (<b>2</b>) was isolated from the roots of <i>Berberis sieboldii</i> Miq. The NMR data of <b>2</b> 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.</p>","PeriodicalId":47,"journal":{"name":"Journal of Natural Products ","volume":" ","pages":"191-198"},"PeriodicalIF":3.3000,"publicationDate":"2025-01-24","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":"0","resultStr":"{\"title\":\"Structural Similarity in Natural Products Leading to Sample Misidentification: A Case Study of the Bisbenzylisoquinoline Alkaloids Oxyacanthine and Berbamine.\",\"authors\":\"Yan Cheng, Davlat Akramov, Lola Yakhshilikova, Chengwei Zhu, Jie Lu, Jin Suo, Santhosh Pugazh, Hongjian Qin, Safomuddin Abduahadi, Jishan Qin, Tianwen Hu, Jingshan Shen, Feipu Yang, Haji A Aisa\",\"doi\":\"10.1021/acs.jnatprod.4c01109\",\"DOIUrl\":null,\"url\":null,\"abstract\":\"<p><p>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 (<b>1</b>). The NMR data of all purchased samples were consistent. The X-ray crystallography characterization of one sample revealed it to be <b>1</b>. The NMR data of <b>1</b> were fully assigned for the first time. Berbamine (<b>2</b>) was isolated from the roots of <i>Berberis sieboldii</i> Miq. The NMR data of <b>2</b> 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.</p>\",\"PeriodicalId\":47,\"journal\":{\"name\":\"Journal of Natural Products \",\"volume\":\" \",\"pages\":\"191-198\"},\"PeriodicalIF\":3.3000,\"publicationDate\":\"2025-01-24\",\"publicationTypes\":\"Journal Article\",\"fieldsOfStudy\":null,\"isOpenAccess\":false,\"openAccessPdf\":\"\",\"citationCount\":\"0\",\"resultStr\":null,\"platform\":\"Semanticscholar\",\"paperid\":null,\"PeriodicalName\":\"Journal of Natural Products \",\"FirstCategoryId\":\"99\",\"ListUrlMain\":\"https://doi.org/10.1021/acs.jnatprod.4c01109\",\"RegionNum\":2,\"RegionCategory\":\"生物学\",\"ArticlePicture\":[],\"TitleCN\":null,\"AbstractTextCN\":null,\"PMCID\":null,\"EPubDate\":\"2025/1/9 0:00:00\",\"PubModel\":\"Epub\",\"JCR\":\"Q2\",\"JCRName\":\"CHEMISTRY, MEDICINAL\",\"Score\":null,\"Total\":0}","platform":"Semanticscholar","paperid":null,"PeriodicalName":"Journal of Natural Products ","FirstCategoryId":"99","ListUrlMain":"https://doi.org/10.1021/acs.jnatprod.4c01109","RegionNum":2,"RegionCategory":"生物学","ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":null,"EPubDate":"2025/1/9 0:00:00","PubModel":"Epub","JCR":"Q2","JCRName":"CHEMISTRY, MEDICINAL","Score":null,"Total":0}
Structural Similarity in Natural Products Leading to Sample Misidentification: A Case Study of the Bisbenzylisoquinoline Alkaloids Oxyacanthine and Berbamine.
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.
期刊介绍：
The Journal of Natural Products invites and publishes papers that make substantial and scholarly contributions to the area of natural products research. Contributions may relate to the chemistry and/or biochemistry of naturally occurring compounds or the biology of living systems from which they are obtained.
Specifically, there may be articles that describe secondary metabolites of microorganisms, including antibiotics and mycotoxins; physiologically active compounds from terrestrial and marine plants and animals; biochemical studies, including biosynthesis and microbiological transformations; fermentation and plant tissue culture; the isolation, structure elucidation, and chemical synthesis of novel compounds from nature; and the pharmacology of compounds of natural origin.
When new compounds are reported, manuscripts describing their biological activity are much preferred.
Specifically, there may be articles that describe secondary metabolites of microorganisms, including antibiotics and mycotoxins; physiologically active compounds from terrestrial and marine plants and animals; biochemical studies, including biosynthesis and microbiological transformations; fermentation and plant tissue culture; the isolation, structure elucidation, and chemical synthesis of novel compounds from nature; and the pharmacology of compounds of natural origin.
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