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处理:儿茶素和没食子酸衍生物的转化及其鉴定。

Processing of : transformation of catechin and gallic acid derivatives and their identification.

作者信息

Bai Junqi, Zou Qiyu, Su He, Liao Baosheng, Wang Ping, Huang Juan, Zhang Danchun, Gong Lu, Xu Wen, Zhang Jing, Huang Zhihai, Qiu Xiaohui

机构信息

Guangdong Provincial Hospital of Traditional Chinese Medicine, The Second Clinical Medical College of Guangzhou University of Chinese Medicine, Guangzhou, China.

Shanghai Dehua Traditional Chinese Medicine Co., Ltd., Shanghai, China.

出版信息

Front Pharmacol. 2024 Feb 26;15:1356876. doi: 10.3389/fphar.2024.1356876. eCollection 2024.

Abstract

The root of (Thunb.) Moldenke (RM) has been used widely in formulations of herbal medicines in China for centuries. Raw . (RRM) should be processed before use to reduce toxicity and increase efficacy. However, detailed regulation of the processing endpoint is lacking, and the duration of processing can vary considerably. We conducted in-depth research on stilbene glycosides in RM at different processing times. Previously, we discovered that 219 stilbene glycosides changed markedly in quantity and content. Therefore, we proposed that processing causes changes in various chemical groups. To better explain the mechanism of RM processing for toxicity reduction and efficacy enhancement, we used a method of tandem mass spectrometry described previously to research gallic acid based and catechin based metabolites. A total of 259 metabolites based on gallic acid and 112 metabolites based on catechins were identified. Among these, the peak areas of 157 gallic acid and 81 catechins gradually decreased, those of another 71 gallic acid and 30 catechins first increased and then decreased, those of 14 gallic acid and 1 catechin gradually increased. However, 17 of the gallic acids showed no significant changes. We speculate that many gallic acid metabolites hydrolyze to produce gallic acid; moreover, the dimers/trimers of catechins, after being cleaved into catechins, epicatechin, gallic acid catechins, and epicatechin monomers, are cleaved into gallic acid and protocatechualdehyde under high temperature and high humidity, subsequently participating in the Maillard reaction and browning reactions. We showed that processing led to changes in chemical groups, clarification of the groups of secondary metabolites could provide a basis for research on the pharmacological and toxic mechanisms of RM, as well as the screening of related markers.

摘要

(Thunb.)Moldenke(RM)的根在中国几个世纪以来一直广泛用于草药配方中。生的 (RRM)在使用前应进行炮制以降低毒性并提高疗效。然而,缺乏对炮制终点的详细规范,炮制时间也可能有很大差异。我们对不同炮制时间的RM中的芪苷进行了深入研究。此前,我们发现219种芪苷的数量和含量有明显变化。因此,我们提出炮制会导致各种化学基团发生变化。为了更好地解释RM炮制降低毒性和增强疗效的机制,我们使用了先前描述的串联质谱法研究基于没食子酸和儿茶素的代谢产物。共鉴定出259种基于没食子酸的代谢产物和112种基于儿茶素的代谢产物。其中,157种没食子酸和81种儿茶素的峰面积逐渐减小,另外71种没食子酸和30种儿茶素的峰面积先增大后减小,14种没食子酸和1种儿茶素的峰面积逐渐增大。然而,17种没食子酸没有显著变化。我们推测许多没食子酸代谢产物水解产生没食子酸;此外,儿茶素的二聚体/三聚体在裂解为儿茶素、表儿茶素、没食子酸儿茶素和表儿茶素单体后,在高温高湿条件下裂解为没食子酸和原儿茶醛,随后参与美拉德反应和褐变反应。我们表明炮制导致化学基团发生变化,明确次生代谢产物的基团可为研究RM的药理和毒理机制以及筛选相关标志物提供依据。

https://cdn.ncbi.nlm.nih.gov/pmc/blobs/184a/10926517/b523507b3be6/fphar-15-1356876-g001.jpg

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