4H-1-Benzopyran-4-one, 2,3-dihydro-7-hydroxy-2-(4-hydroxyphenyl)-, (2S)-/(2S)-7-hydroxy-2-(4-hydroxyphenyl)-2,3-dihydrochromen-4-one/4H-1-Benzopyran-4-one, 2,3-dihydro-7-hydroxy-2-(4-hydroxyphenyl)-, (S)-/(2S)-7-Hydroxy-2-(4-hydroxyphenyl)-2,3-dihydro-4H-1-benzopyran-4-one/Liquiritigenin/(2S)-7-Hydroxy-2-(4-hydroxyphenyl)-2,3-dihydro-4H-chromen-4-one
Methanol; Ethanol; DMF
529.5±50.0 °C at 760 mmHg
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provides coniferyl ferulate(CAS#:578-86-9) MSDS, density, melting point, boiling point, structure, formula, molecular weight etc. Articles of coniferyl ferulate are included as well.>> amp version: coniferyl ferulate
In this study,liquiritigenin sulfonation was characterized using recombinant human sulfotransferases( SULTs). The chemical structure of liquiritigenin sulfate was determined by ultra-high performance liquid chromatography-quadrupole time-of-flight mass spectrometry( UPLC-Q-TOF-MS/MS). Then model fitting and parameter estimation were performed using the Graphpad Prism V5 software. Various SULT enzymes( SULT1 A1,1 A2,1 A3,1 B1,1 C2,1 C4,1 E1 and 2 A1) were able to catalyze the formation of liquiritigenin-7-O-sulfate. Sulfonation of liquiritigenin-7-hydroxy( 7-OH) by these eight SULT enzymes consistently displayed the classical Michaelis-Menten profile. According to the intrinsic clearance( CLint) value,the sulfonation rates of liquiritigenin-7-OH by expressed SULT enzymes followed the following rank order: SULT1 C4 > SULT1 A3 > SULT1 E1 > SULT1 A1 > SULT1 A2 > SULT1 B1 >SULT1 C2>SULT2 A1. Further,liquiritigenin-7-O-sulfonation was significantly correlated with the SULT1 A3 protein levels( P<0. 05).Then,human embryonic kidney( HEK) 293 cells over expressing SULT1 A3( named as HEK-SULT1 A3 cells) were conducted. As a result,liquiritigenin-7-O-sulfate( L-7-S) was rapidly generated upon incubation of the cells with liquiritigenin. Consistent with SULT1 A3,sulfonation of liquiritigenin-7-OH in HEK-SULT1 A3 cells also followed the Michaelis-Menten kinetics. The derived Vmaxvalues was( 0. 315±0. 009) μmol·min-1·g-1,Kmwas( 7. 04±0. 680) μmol·L-1,and CLintwas( 0. 045±0. 005) L·min-1·g-1. Moreover,the sulfonation characters of liquiritigenin( 7-OH) in SULT1 A3 were strongly correlated with that in HEK-SULT1 A3 cells( P<0. 001).The results indicated that HEK-SULT1 A3 cells have shown the catalytic function of SULT1 A3 enzymes. In conclusion,liquiritigenin was subjected to efficient sulfonation,and SULT1 A3 enzyme plays an important role in the sulfonation of liquiritigenin-7-OH. Significant sulfonation should be the main reason for the low bioavailability of liquiritigenin. In addition,HEK-SULT1 A3 cells were conducted and successfully used to evaluate liquiritigenin sulfonation,which will provide an appropriate tool to accurately depict the sulfonation disposition of liquiritigenin in vivo.
HEK-SULT1A3 cells; SULT1A3; bioavailability; liquiritigenin; sulfonation
[7-hydroxy sulfonation of liquiritigenin by recombinant SULT1A3 enzyme and HEK-SULT1A3 cells].
Zhang YD1, Li HY1, Liu FY1, Niu J1, Wang X1, Liang C1, Sun H1.
Osteoarthritis (OA) is an age-related arthropathy which has been considered to be associated with inflammatory damage and cartilage degradation. Liquiritigenin (LG), the main bioactive component of the rhizomes of Glycyrrhiza uralensis, has exhibited promising anti-inflammatory and anti-oxidative potential in numerous inflammatory diseases. However, the effects of LG on OA remain unclear. In this study, the therapeutic effects as well as the underlying mechanisms of LG on interleukin-1β (IL-1β)-treated rat chondrocytes had been investigated. Our results showed that LG could inhibit the IL-1β-induced expression of nitic oxide (NO) and prostaglandin E2 (PGE2). In consist with these findings, the IL-1β-induced production of inducible nitic oxide synthase (iNOS) and cyclooxygenase-2 (COX2) could also be decreased by LG. Meanwhile, LG could suppress the IL-1β-induced upregulation of cartilage matrix catabolic enzymes including aggrecanase-2 (ADAMTS5) and matrix metalloproteinases (MMPs). Besides, the IL-1β-induced degradation of collagen II and aggrecan could be alleviated by LG. Moreover, LG prevented cartilage damage in IL-1β-treated rat cartilage explants. Mechanistically, LG functioned by inhibiting mitogen-activated protein kinase (MAPK) and nuclear factor-kappa B (NF-κB) pathways activation. In general, this study reveals the anti-inflammatory properties of LG on IL-1β-treated rat chondrocytes and the possible mechanisms behind it, which may provide new ideas for OA therapy.
Copyright © 2019. Published by Elsevier B.V.
ADAMTS5; COX2; Liquiritigenin; MMPs; Osteoarthritis; iNOS
Liquiritigenin inhibits IL-1β-induced inflammation and cartilage matrix degradation in rat chondrocytes.
Tu C1, Ma Y1, Song M2, Yan J1, Xiao Y3, Wu H4.
2019 Sep 5
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 (R2 ) > 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.
© 2019 WILEY-VCH Verlag GmbH & Co. KGaA, Weinheim.
acokinetics; pharmacokinetics; polycystic ovary syndrome; tandem mass spectrometry; traditional Chinese medicine
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 JJ1,2, Cheng Y1,2, Shao YY1,2, Chang ZP1,2, Guo YT1,2, Feng XJ1,2, Xu D1,2, Zhang JP1,2, Song Y1,2, Hou RG1,2.
Liquiritigenin, a flavanone isolated from Glycyrrhiza uralensis, is a highly selective estrogen receptor β (ERβ) agonist with an EC50 of 36.5 nM for activation of the ERE tk-Luc.