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Chemical transformation and target preparation of saponins in stems and leaves of Panax notoginseng

机译:三七茎叶中皂苷的化学转化及靶标制备

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Background: Notoginsenoside Ft1 is a promising potential candidate for cardiovascular and cancer diseasetherapy owing to its positive pharmacological activities. However, the yield of Ft1 is ultralow utilizingreported methods. Herein, an acid hydrolyzing strategy was implemented in the acquirement ofrare notoginsenoside Ft1.Methods: Chemical profiles were identified by ultraperformance liquid chromatography coupled withquadruple-time-of-flight and electrospray ionization mass spectrometry (UPLC-Q/TOF-ESI-MS). Theacid hydrolyzing dynamic changes of chemical compositions and the possible transformation pathwaysof saponins were monitored by ultrahigh-performance LC coupled with tandem MS (UHPLC-MS/MS).Results and conclusion: Notoginsenoside Ft1 was epimerized from notoginsenoside ST4, which wasgenerated through cleaving the carbohydrate side chains at C-20 of notoginsenosides Fa and Fc, and vinaginsenosideR7, and further converted to other compounds via hydroxylation at C-25 or hydrolysis of thecarbohydrate side chains at C-3 under the acid conditions. High temperature contributed to the hydroxylationreaction at C-25 and 25% acetic acid concentration was conducive to the preparation ofnotoginsenoside Ft1. C-20 epimers of notoginsenoside Ft1 and ST4 were successfully separated utilizingsolvent method of acetic acid solution. The theoretical preparation yield rate of notoginsenoside Ft1 wasabout 1.8%, which would be beneficial to further study on its bioactivities and clinical application.
机译:背景:三七皂苷Ft1由于其积极的药理活性,是心血管和癌症疾病治疗的有希望的潜在候选者。然而,利用报告的方法,Ft1的产率极低。方法:采用超高效液相色谱-四倍飞行时间-电喷雾电离质谱法(UPLC-Q / TOF-ESI-MS),对稀有三七皂苷Ft1进行了酸水解。超高效液相色谱-串联质谱(UHPLC-MS / MS)监测了酸水解物化学成分的动态变化以及皂苷可能的转化途径。结果与结论:三七皂甙ST4是三七皂甙Ft1的差向异构体,三元皂甙STt是通过裂解碳水化合物生成的。三七皂苷Fa和Fc以及长春皂苷R7在C-20的侧链,并通过在酸性条件下在C-25的羟基化或在C-3的碳水化合物侧链的水解进一步转化为其他化合物。高温促进了C-25的羟基化反应,乙酸浓度为25%有利于三七皂苷Ft1的制备。利用乙酸溶液的溶剂法成功分离了三七皂苷Ft1和ST4的C-20差向异构体。三七皂苷Ft1的理论制备得率约为1.8%,有利于进一步研究其生物活性和临床应用。

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