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人参皂苷Rg5的氧化和水解:一条被低估的降解途径、未知降解产物的分离与表征

Oxidation and Hydrolysis of Ginsenoside Rg5: An Underestimated Degradation Pathway, Isolation, and Characterization of Unknown Degradation Products.

作者信息

Cheng Leqin, Ye Anqi, Tao Yunqi, Zhang Yuewei

机构信息

School of Chemistry and Pharmaceutical Engineering, Jilin Institute of Chemical Technology, Jilin 132022, China.

出版信息

ACS Omega. 2025 Apr 9;10(15):15732-15743. doi: 10.1021/acsomega.5c01444. eCollection 2025 Apr 22.

DOI:10.1021/acsomega.5c01444
PMID:40290950
原文链接:https://pmc.ncbi.nlm.nih.gov/articles/PMC12019737/
Abstract

Ginsenoside Rg5, a secondary ginsenoside derived from the degradation of protopanaxadiol saponins, exhibits various pharmacological activities, including anticancer, anti-inflammatory, antidiabetic, and memory-enhancing effects, making it a promising candidate for natural medicine. However, research on the stability of Rg5, particularly in aqueous solutions, remains limited. This study systematically investigates the stability of ginsenoside Rg5 in water by monitoring its degradation over time under controlled conditions. The stability of the Rg5 aqueous solution was assessed by investigating the influences of temperature and time, employing high-performance liquid chromatography (HPLC) analysis to evaluate its degradation. The findings indicated substantial degradation of Rg5, with approximately 95% decomposition observed after a period of 10 days. The decomposition products were isolated using preparative liquid chromatography and identified through high-resolution mass spectrometry (HR-MS), NMR, and induced circular dichroism (ICD) analyses. A novel derivative was identified, and its degradation pathway was elucidated, encompassing oxidation, hydrolysis, and dehydration processes that culminated in the formation of four distinct stereoisomers. This study elucidates the instability of Rg5 in aqueous environments and offers significant insights into its decomposition mechanism. The findings emphasize the critical importance of optimizing storage conditions and minimizing exposure to water and oxygen to enhance the stability of Rg5, thereby advancing its potential applications in pharmaceutical development and storage.

摘要

人参皂苷Rg5是原人参二醇皂苷降解产生的次生皂苷,具有多种药理活性,包括抗癌、抗炎、抗糖尿病和增强记忆作用,使其成为天然药物的一个有潜力的候选物。然而,关于Rg5稳定性的研究,特别是在水溶液中的稳定性研究仍然有限。本研究通过在可控条件下监测其随时间的降解情况,系统地研究了人参皂苷Rg5在水中的稳定性。通过研究温度和时间的影响来评估Rg5水溶液的稳定性,采用高效液相色谱(HPLC)分析来评估其降解情况。研究结果表明Rg5发生了大量降解,在10天的时间内观察到约95%的分解。使用制备液相色谱分离分解产物,并通过高分辨率质谱(HR-MS)、核磁共振(NMR)和诱导圆二色性(ICD)分析进行鉴定。鉴定出一种新的衍生物,并阐明了其降解途径,包括氧化、水解和脱水过程,最终形成四种不同的立体异构体。本研究阐明了Rg5在水环境中的不稳定性,并对其分解机制提供了重要见解。研究结果强调了优化储存条件以及尽量减少与水和氧气接触以提高Rg5稳定性的至关重要性,从而推动其在药物开发和储存中的潜在应用。

https://cdn.ncbi.nlm.nih.gov/pmc/blobs/296c/12019737/c09b3cca2383/ao5c01444_0007.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/296c/12019737/080bfc950f07/ao5c01444_0001.jpg
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https://cdn.ncbi.nlm.nih.gov/pmc/blobs/296c/12019737/c09b3cca2383/ao5c01444_0007.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/296c/12019737/080bfc950f07/ao5c01444_0001.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/296c/12019737/5d210718dbd8/ao5c01444_0002.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/296c/12019737/6fa54b4b0dfa/ao5c01444_0003.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/296c/12019737/b3ac109d49d6/ao5c01444_0004.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/296c/12019737/f9945cf8db64/ao5c01444_0005.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/296c/12019737/eea9d2618b5c/ao5c01444_0006.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/296c/12019737/c09b3cca2383/ao5c01444_0007.jpg

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本文引用的文献

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