Department of Medicinal Chemistry and Pharmacognosy, UIC/NIH Center for Botanical Dietary Supplements Research, University of Illinois College of Pharmacy, 833 S. Wood Street, Chicago, IL 60612-7231, USA.
Fitoterapia. 2012 Apr;83(3):441-60. doi: 10.1016/j.fitote.2011.12.006. Epub 2011 Dec 9.
Black cohosh preparations are popular dietary supplements among women seeking alternative treatments for menopausal complaints. For decades, triterpene glycosides and phenolic acids have dominated the phytochemical and biomedical research on this plant. In this study, we provide evidence that black cohosh contains an unexpected and highly diverse group of secondary nitrogenous metabolites previously unknown to exist in this plant. Using a dereplication approach that combines accurate mass measurements, database searches and general knowledge of biosynthetic pathways of natural products, we identified or tentatively identified 73 nitrogen-containing metabolites, many of which are new natural products. The identified compounds belong to several structural groups including alkaloids, amides or esters of hydroxycinnamic acids and betains. Among the alkaloids, several classes such as guanidino alkaloids, isoquinolines and β-carbolines were identified. Fragmentation patterns for major compound classes are discussed, which provides a framework for the discovery of these compounds from other sources. Identification of alkaloids as a well-known group of bioactive natural products represents an important advance in better understanding of the pharmacological profile of black cohosh.
黑升麻制剂是深受寻求更年期症状替代疗法的女性欢迎的膳食补充剂。数十年来，三萜糖苷和酚酸一直主导着对这种植物的植物化学和生物医学研究。在这项研究中，我们提供的证据表明，黑升麻含有一组以前未知的、意想不到的、高度多样化的含氮次生代谢物。我们使用一种去重复方法，结合准确的质量测量、数据库搜索和对天然产物生物合成途径的一般了解，鉴定或暂定鉴定了 73 种含氮代谢物，其中许多是新的天然产物。鉴定出的化合物属于几种结构类别，包括生物碱、羟基肉桂酸的酰胺或酯和甜菜碱。在生物碱中，鉴定出了胍类生物碱、异喹啉类和β-咔啉类等几类。还讨论了主要化合物类别的断裂模式，为从其他来源发现这些化合物提供了框架。将生物碱鉴定为一组众所周知的生物活性天然产物，是更好地了解黑升麻药理特性的重要进展。
