The mechanism of hydrothermal hydrolysis for glycyrrhizic acid into glycyrrhetinic acid and glycyrrhetinic acid 3- O -mono-β- d -glucuronide in subcritical water

Fan, Rui; Li, Nan; Xu, Huaide; Xiang, Jun; Wang, Lei; Gao, Yanxiang

doi:10.1016/j.foodchem.2015.06.039

Cited by 19 publications

(11 citation statements)

References 41 publications

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“…However, as the most important bioactive metabolite for glycyrrhetinic acid, M34 was not detected in the plasma of normal rats. The result was consistent with previous literature reports . In our further experiment, M34 was observed in the feces of normal rats (data not shown).…”

Section: Resultssupporting

confidence: 94%

Comparative pharmacokinetics and metabolites study of seven major bioactive components of Shaoyao‐Gancao decoction in normal and polycystic ovary syndrome rats by ultra high pressure liquid chromatography with tandem mass spectrometry

Liu

Cheng

Shao

et al. 2019

J of Separation Science

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A simple and sensitive liquid chromatography with tandem mass spectrometry method was developed for simultaneous quantification of paeoniflorin, albiflorin, oxypaeoniflorin, liquiritin, liquiritigenin, glycyrrhetinic acid, and glycyrrhizin in rat plasma after oral administration of Shaoyao-Gancao decoction, which is traditionally used in the treatment of polycystic ovary syndrome. The plasma samples were pretreated with methanol as precipitant. The method exhibited good linearity (correlation coefficient (R 2 ) > 0.99) with lower quantification limits of 0.595-4.69 ng/mL for all analytes. Intra-and interbatch precision, accuracy, recovery, and stability of the method were all within accepted criteria. The results showed that the pharmacokinetic behaviors of the seven compounds were altered in the pathological status of polycystic ovary syndrome. Furthermore, a total of 36 metabolites were structurally identified based on their accurate masses and fragment ions. The major metabolic pathway involves phase I metabolic reactions (such as hydroxylation), phase II metabolic reactions (such as sulfation and glucuronidation conjugation) as well as the combined multiple-step metabolism. This study is the first report on the pharmacokinetic and metabolic information of Shaoyao-Gancao decoction in both normal and model rats, which would provide scientific evidences for the bioactive chemical basis of herbal medicines and also promote the clinical application of Shaoyao-Gancao decoction for treating polycystic ovary syndrome. K E Y W O R D Sacokinetics, pharmacokinetics, polycystic ovary syndrome, tandem mass spectrometry, traditional Chinese medicine Article Related Abbreviations: AUC 0-∞ , total area under the plasma concentration-time curve from time zero to time infinity; AUC 0-t , total area under the plasma concentration-time curve from time zero to time t; C max , peak plasma concentration; CE, collision energy; DMPK, drug metabolism and pharmacokinetics; GU, Glycyrrhizae uralensis; IS, internal standard; LLOQ, linearity and low limits of quantification; MRM, multiple reaction monitoring; PCOS, polycystic ovary syndrome; QC, quality control; QTRAP, triple quadrupole-linear ion trap; RP, Radix Paeoniae Alba; SGD, Shaoyao-Gancao decoction; T 1/2 , elimination half-life; TCM, traditional Chinese medicine; T max , time to reach C max .Jun-jin Liu and Yao Cheng contribute equally to this paper. 2534

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Section: Resultssupporting

confidence: 94%

Comparative pharmacokinetics and metabolites study of seven major bioactive components of Shaoyao‐Gancao decoction in normal and polycystic ovary syndrome rats by ultra high pressure liquid chromatography with tandem mass spectrometry

Liu

Cheng

Shao

et al. 2019

J of Separation Science

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“…2) have aglycone saponins. It has been proved that GA can ameliorate ventricular arrhythmia (Wu et al, 2015) and GL transforms to GA in the absorption process (Fan et al, 2016). HA is considered to be effective on CVD, and its heat stability in water is better than that of other alkaloids (Yue et al, 2008;Zhang et al, 2015).…”

Section: Introductionmentioning

confidence: 99%

Protective mechanisms of hypaconitine and glycyrrhetinic acid compatibility in oxygen and glucose deprivation injury

Wang

Wan

Zhou

et al. 2017

J. Zhejiang Univ. Sci. B

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This study investigated the protective effect of the compatibility of hypaconitine (HA) and glycyrrhetinic acid (GA) on H9c2 cells under oxygen and glucose deprivation (OGD)-induced injury, and the possible mechanisms. We found that HA+GA significantly improved pathology and morphology of the nucleus and ultrastructure of H9c2 cells under OGD as determined by Hoechst 33342 staining and transmission electron microscopy (TEM) tests. It also reduced the releases of lactate dehydrogenase (LDH), creatine kinase-myocardial band isoenzyme (CK-MB), and aspartate transaminase (AST) from the cultured supernatant of H9c2 cells, which were tested by enzyme-linked immune sorbent assay (ELISA) kits. In addition, it lessened the apoptotic rate as determined by a fluorescein isothiocyanate-annexin V/propidium iodide (FITC-AV/PI) double staining assay. It was also found that HA+GA might regulate the protein expression associated with the phosphatidylinositol 3-kinase (PI3K)/Akt signaling pathway. Overall, the study demonstrated that HA+GA protected H9c2 cells against OGD-induced injury, and the signaling mechanism might be related to the PI3K/Akt signaling pathway.

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“…GA and GAMG were commonly produced by conventional chemical and biotransformation methods [ 4 , 8 ]. To overcome the drawbacks of the current methods, such as a long hydrolysis time, a complicated operation process, and high production cost, the subcritical water system was introduced to generate the derivants of GL in our previous work [ 9 ]. But, the separation technology of GL and its derivants was scarcely reported.…”

Section: Introductionmentioning

confidence: 99%

Separation of Glycyrrhizic Acid and Its Derivants from Hydrolyzation in Subcritical Water by Macroporous Resin

Fan

2020

Molecules

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Glycyrrhizic acid (GL) and its derivants, glycyrrhetinic acid 3-O-mono-β-d-glucuronide (GAMG) and glycyrrhetinic acid (GA) hydrolyzed in subcritical water, are bioactive substances and edulcorators. In this work, a separation strategy for these three substances was established. The effects of adsorbent and eluent were investigated by static/dynamic adsorption and multi-stage desorption with the mechanism analysis. The adsorption of them onto EXA50 resin was well fitted by the pseudo second-order kinetic model. The optimal dynamic adsorption flow rate was 6 bed volume (BV)/h, and water of pH = 12 was used to elute GL at 4 BV/h, then n-buthanol was used subsequently to elute GA at 1 BV/h, and finally 90% ethanol was applied to elute GAMG at 2 BV/h. As a result, purities of these compounds increased, which demonstrated that this adsorption-desorption technology was simple and efficient, and indicated the potential for large-scale purification and preparation of GL and its derivants in the future.

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The mechanism of hydrothermal hydrolysis for glycyrrhizic acid into glycyrrhetinic acid and glycyrrhetinic acid 3- O -mono-β- d -glucuronide in subcritical water

Cited by 19 publications

References 41 publications

Comparative pharmacokinetics and metabolites study of seven major bioactive components of Shaoyao‐Gancao decoction in normal and polycystic ovary syndrome rats by ultra high pressure liquid chromatography with tandem mass spectrometry

Comparative pharmacokinetics and metabolites study of seven major bioactive components of Shaoyao‐Gancao decoction in normal and polycystic ovary syndrome rats by ultra high pressure liquid chromatography with tandem mass spectrometry

Protective mechanisms of hypaconitine and glycyrrhetinic acid compatibility in oxygen and glucose deprivation injury

Separation of Glycyrrhizic Acid and Its Derivants from Hydrolyzation in Subcritical Water by Macroporous Resin

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