Flavonoids are ubiquitous plant metabolites with a lot of purported pharmacological properties. Emergence of advanced analytical instrumentations such as liquid chromatography hyphenated to mass spectrometry (LC–MS) has allowed for unparallel elucidation of chemical compositions of various plants. Through such analyses, various chemical modifications such as glycosylation and other forms of isomerization have been shown to be an evolutionary strategy of plants to diversify their metabolite compositions (metabolome). Herein, metabolite fingerprinting of two closely related plant species vis Coccinia grandis and Coccinia rehmannii revealed that flavonoids attached to either di- or tri-saccharides are prone to isomerization, a phenomenon termed glycoisomerization herein. Furthermore, modification known as sugar acylation by known biologically active metabolites such as derivatives of cinnamic acids (i. e., caffeic acid and coumaric acid) has been noted in C. rehmannii but not in C. grandis. The findings of the current study reveal glycosylation patterns of flavonoids as an evolutionary strategy used by plants to diversify its metabolome, a phenomenon of which the biological consequence is still to be investigated.

类黄酮是普遍存在的植物代谢产物，具有许多声称的药理特性。诸如液相色谱法，质谱联用技术（LC-MS）等高级分析仪器的出现，使各种植物的化学成分得到了无与伦比的阐明。通过此类分析，各种化学修饰（例如糖基化和其他形式的异构化）已被证明是植物使其代谢物成分（代谢组）多样化的进化策略。本文中，两种对大球藻和熟球藻密切相关的植物的代谢产物指纹图谱显示，黄酮类化合物附着于二或三糖易于异构化，在本文中称为糖异构化的现象。此外，通过公知的生物活性代谢物称为糖酰化修饰如肉桂酸（即，咖啡酸和香豆酸）衍生物已注意到C. rehmannii但不是在C.桉。本研究的发现揭示了类黄酮的糖基化模式是植物用于使其代谢组多样化的一种进化策略，这种现象的生物学后果尚待研究。