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

Abstract

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.

Effects of extraction, fermentation, and storage processes on the levels of choline derived from calabash fruit (Crescentia cujete L.)

“…We suspected that the decreased choline levels could be correlated with the purity of the product produced through extraction and fermentation. A previous study showed that pure caffeoylgluconic acid has better quality and stability than its mixture product [20].…”

Identification of Q-Markers from Hedan Tablet by employing “spider-web” mode and taking compounds’ hepatotoxicity into account

“…Fortunately, under the guidance of the Q-Marker theory proposed by Academician Changxiao Liu, it sheds the light for the quality control of CMM related preparations with the complicated compounds ( Liu et al, 2016 , Liu et al, 2017 , Liu, 2021 ). In order to identify Q-Markers from CMM related preparations, “spider-web” mode was successfully developed and extended to apply in stability study, optimization of extracting methods and processing parameters, screening of active fractions, and so on ( Li et al, 2019b , Wang et al, 2016 , Yang et al, 2018 , Yu et al, 2018 , Zhang et al, 2019a ). “Spider-web” mode based on “content-stability-activity” has been proven to be a great strategy, which can filter out the redundant compounds and focus on the key indexes of quality control ( Zhang et al, 2020 ).…”

Quantitative Analysis and Stability Study on Iridoid Glycosides from Seed Meal of Eucommia ulmoides Oliver

“…have been reported [14][15][16][17]. There is no doubt that a systematic understanding of the stability of bioactive compounds would contribute to improvements in manufacturing and controlling the quality of CMMs [18][19][20]. Meanwhile, it is also vital to design the suitable sample packaging and choose storage conditions for products.…”