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Stability Study and Identification of Degradation Products of Caffeoylgluconic Acid Derivatives from Fructus Euodiae

Caffeoylgluconic acid derivatives are characteristic constituents isolated from the aqueous extract of Fructus Euodiae. In this research focusing on caffeoylgluconic acid derivatives, trans-caffeoyl-6-O-d-gluconic acid (CGA), trans-caffeoyl-6-O-d-gluconic acid methyl ester (CGA-ME), and trans-caffeo...

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Autores principales: Yu, Huijuan, Yang, Jing, Ding, Jiamin, He, Ying, Jiang, Zhenzuo, Chai, Xin, Wang, Yuefei
Formato: Online Artículo Texto
Lenguaje:English
Publicado: MDPI 2018
Materias:
Acceso en línea:https://www.ncbi.nlm.nih.gov/pmc/articles/PMC6222684/
https://www.ncbi.nlm.nih.gov/pubmed/30096766
http://dx.doi.org/10.3390/molecules23081975
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author Yu, Huijuan
Yang, Jing
Ding, Jiamin
He, Ying
Jiang, Zhenzuo
Chai, Xin
Wang, Yuefei
author_facet Yu, Huijuan
Yang, Jing
Ding, Jiamin
He, Ying
Jiang, Zhenzuo
Chai, Xin
Wang, Yuefei
author_sort Yu, Huijuan
collection PubMed
description Caffeoylgluconic acid derivatives are characteristic constituents isolated from the aqueous extract of Fructus Euodiae. In this research focusing on caffeoylgluconic acid derivatives, trans-caffeoyl-6-O-d-gluconic acid (CGA), trans-caffeoyl-6-O-d-gluconic acid methyl ester (CGA-ME), and trans-caffeoyl-6-O-d-glucono-γ-lactone (CGA-LT), a systematic study of stability was performed under different temperatures and pH levels by ultra performance liquid chromatography-diode array detector (UPLC-DAD) and ultra performance liquid chromatography-diode array detector/electrospray ionization-quadrupole-time of flight mass spectrometry (UPLC-DAD/ESI-Q-TOF MS). From the concentration–time curves and sensitivity index (SeI), it was found that compared to CGA, which is inert to the variation of temperature and pH in the tested range, CGA-ME and CGA-LT were more sensitive, with stabilities more likely to be influenced by temperature. Considering the stability index (StI), the integrated stability of CGA was the best, and that of CGA-ME was the worst. In terms of the quasi-molecular and fragment ions of the tested compounds, the degradation products were identified or tentatively characterized, which could shed light on the degradation pathways. CGA-ME and CGA-LT were easily converted to CGA by hydrolytic reaction, all of which were susceptible to the formation of isomers. This study elucidated the degradation mechanism of caffeoylgluconic acid derivatives, contributing to better guidance on manufacturing and controlling the quality of drugs.
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spelling pubmed-62226842018-11-13 Stability Study and Identification of Degradation Products of Caffeoylgluconic Acid Derivatives from Fructus Euodiae Yu, Huijuan Yang, Jing Ding, Jiamin He, Ying Jiang, Zhenzuo Chai, Xin Wang, Yuefei Molecules Article Caffeoylgluconic acid derivatives are characteristic constituents isolated from the aqueous extract of Fructus Euodiae. In this research focusing on caffeoylgluconic acid derivatives, trans-caffeoyl-6-O-d-gluconic acid (CGA), trans-caffeoyl-6-O-d-gluconic acid methyl ester (CGA-ME), and trans-caffeoyl-6-O-d-glucono-γ-lactone (CGA-LT), a systematic study of stability was performed under different temperatures and pH levels by ultra performance liquid chromatography-diode array detector (UPLC-DAD) and ultra performance liquid chromatography-diode array detector/electrospray ionization-quadrupole-time of flight mass spectrometry (UPLC-DAD/ESI-Q-TOF MS). From the concentration–time curves and sensitivity index (SeI), it was found that compared to CGA, which is inert to the variation of temperature and pH in the tested range, CGA-ME and CGA-LT were more sensitive, with stabilities more likely to be influenced by temperature. Considering the stability index (StI), the integrated stability of CGA was the best, and that of CGA-ME was the worst. In terms of the quasi-molecular and fragment ions of the tested compounds, the degradation products were identified or tentatively characterized, which could shed light on the degradation pathways. CGA-ME and CGA-LT were easily converted to CGA by hydrolytic reaction, all of which were susceptible to the formation of isomers. This study elucidated the degradation mechanism of caffeoylgluconic acid derivatives, contributing to better guidance on manufacturing and controlling the quality of drugs. MDPI 2018-08-08 /pmc/articles/PMC6222684/ /pubmed/30096766 http://dx.doi.org/10.3390/molecules23081975 Text en © 2018 by the authors. Licensee MDPI, Basel, Switzerland. This article is an open access article distributed under the terms and conditions of the Creative Commons Attribution (CC BY) license (http://creativecommons.org/licenses/by/4.0/).
spellingShingle Article
Yu, Huijuan
Yang, Jing
Ding, Jiamin
He, Ying
Jiang, Zhenzuo
Chai, Xin
Wang, Yuefei
Stability Study and Identification of Degradation Products of Caffeoylgluconic Acid Derivatives from Fructus Euodiae
title Stability Study and Identification of Degradation Products of Caffeoylgluconic Acid Derivatives from Fructus Euodiae
title_full Stability Study and Identification of Degradation Products of Caffeoylgluconic Acid Derivatives from Fructus Euodiae
title_fullStr Stability Study and Identification of Degradation Products of Caffeoylgluconic Acid Derivatives from Fructus Euodiae
title_full_unstemmed Stability Study and Identification of Degradation Products of Caffeoylgluconic Acid Derivatives from Fructus Euodiae
title_short Stability Study and Identification of Degradation Products of Caffeoylgluconic Acid Derivatives from Fructus Euodiae
title_sort stability study and identification of degradation products of caffeoylgluconic acid derivatives from fructus euodiae
topic Article
url https://www.ncbi.nlm.nih.gov/pmc/articles/PMC6222684/
https://www.ncbi.nlm.nih.gov/pubmed/30096766
http://dx.doi.org/10.3390/molecules23081975
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