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Chrysin-7-O-glucuronide Sale

(Synonyms: 白杨素-7-0-Β-D-葡萄糖醛酸苷) 目录号 : GC35689

A flavonoid glucuronide with diverse biological activities and an active metabolite of chrysin

Chrysin-7-O-glucuronide Chemical Structure

Cas No.:35775-49-6

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产品描述

Chrysin 7-glucuronide is a flavonoid glucuronide that has been found in S. baicalensis and has diverse biological activities and is an active metabolite of chrysin .1,2,3,4 It is formed from chrysin by various UDP-glucuronosyltransferase (UGT) isoforms, including UGT1A3, UGT1A6, and UGT1A9.4 Chrysin 7-glucuronide inhibits α-glucosidase, α-amylase, and neuraminidase (IC50s = 612, 980, and 428 ?g/ml, respectively).1,2 It also inhibits organic anion transporting polypeptide (OATP) isoforms OATP1A2, OATP1B1, OATP1B3, and OATP2B1 (IC50s = 24.1, 4.4, 14.3, and 0.3 ?M, respectively), as well as breast cancer resistance protein (BCRP) and multidrug resistance-associated protein 2 (MRP2; IC50s = 19.8 and 11.2 ?M, respectively).3

1.Li, K., Yao, F., Xue, Q., et al.Inhibitory effects against α-glucosidase and α-amylase of the flavonoids-rich extract from Scutellaria baicalensis shoots and interpretation of structure-activity relationship of its eight flavonoids by a refined assign-score methodChem. Cent. J.12(1)82(2018) 2.Liu, W., Wang, H., Zhu, B., et al.An activity-integrated strategy of the identification, screening and determination of potential neuraminidase inhibitors from Radix ScutellariaePLoS One12(5)e0175751(2017) 3.Mohos, V., Fliszár-Nyúl, E., Ungvári, O., et al.Effects of chrysin and its major conjugated metabolites chrysin-7-sulfate and chrysin-7-glucuronide on cytochrome P450 enzymes and on OATP, P-gp, BCRP, and MRP2 TransportersDrug Metab. Dispos.48(10)1064-1073(2020) 4.Robotham, S.A., and Brodbelt, J.S.Identification of flavone glucuronide isomers by metal complexation and tandem mass spectrometry: Regioselectivity of uridine 5'-diphosphate-glucuronosyltransferase isozymes in the biotransformation of flavonesJ. Agric. Food Chem61(7)1457-1463(2013)

Chemical Properties

Cas No. 35775-49-6 SDF
别名 白杨素-7-0-Β-D-葡萄糖醛酸苷
Canonical SMILES O=C1C2=C(O)C=C(O[C@@H]3O[C@@H]([C@@H](O)[C@H](O)[C@H]3O)C(O)=O)C=C2OC(C4=CC=CC=C4)=C1
分子式 C21H18O10 分子量 430.36
溶解度 Soluble in DMSO 储存条件 Store at -20°C
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1 mM 2.3236 mL 11.6182 mL 23.2364 mL
5 mM 0.4647 mL 2.3236 mL 4.6473 mL
10 mM 0.2324 mL 1.1618 mL 2.3236 mL
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Research Update

Exploring the active constituents of Oroxylum indicum in intervention of novel coronavirus (COVID-19) based on molecular docking method

Netw Model Anal Health Inform Bioinform 2021;10(1):8.PMID:33585155DOI:10.1007/s13721-020-00279-y.

The severe acute respiratory syndrome COVID-19 declared a global pandemic by WHO has become the present wellbeing worry to the whole world. There is an emergent need to search for possible medications. We report in this study a molecular docking study of eighteen Oroxylum indicum molecules with the main protease (Mpro) responsible for the replication of SARS-CoV-2 virus. The outcome of their molecular simulation and ADMET properties reveal four potential inhibitors of the enzyme (Baicalein-7-O-diglucoside, Chrysin-7-O-glucuronide, Oroxindin and Scutellarein) with preference of ligand Chrysin-7-O-glucuronide that has the second highest binding energy (- 8.6 kcal/mol) and fully obeys the Lipinski's rule of five. Supplementary information: The online version contains supplementary material available at 10.1007/s13721-020-00279-y.

Identification of the bioactive components of Banxia Xiexin Decoction that protect against CPT-11-induced intestinal toxicity via UPLC-based spectrum-effect relationship analyses

J Ethnopharmacol 2021 Feb 10;266:113421.PMID:33022337DOI:10.1016/j.jep.2020.113421.

Ethnopharmacological relevance: Irinotecan (CPT-11) is a valuable chemotherapeutic compound, but its use is associated with severe diarrhea in some patients. The CPT-11 prodrug is converted into the active 7-ethyl-10-hydroxycamptothecin (SN-38) metabolite, which can then be retained for extended periods in the intestine, leading to the onset of diarrhea and related symptoms. Banxia Xiexin Decoction (BXD) is commonly employed for the treatment of gastroenteritis in traditional Chinese medicine (TCM), and in clinical settings, it is used to prevent diarrhea in patients undergoing CPT-11 treatment. To date, however, there have been no studies specifically examining which components of BXD can alleviate the gastrointestinal symptoms associated with CPT-11 administration. Aim: This study aimed to identify the main herbal components of BXD associated with protection against CPT-11-induced intestinal toxicity in a murine model system. Materials and methods: SN-38 levels were measured by UPLC-ESI-MS/MS in samples collected from mice subjected to CPT-11-induced diarrhea that had been administered BXD or different components thereof. Pearson correlation and Grey relational analyses were then used to explore spectrum-effect relationships between reductions in intestinal SN-38 levels and specific chemical fingerprints in samples from mice administered particular combinations of BXD component herbs. Results: We found that different herbal combinations were associated with significant differences in intestinal SN-38 reductions in treated mice. Our spectrum-effect analysis revealed that BXD components including chrysin 6-C-arabinoside-8-C-glucoside, coptisine, hydroxyl oroxylin A 7-O-glucuronide (hydroxyl wogonoside), baicalin, an isomer of 5,6,7-trihydroxyl-flavanone-7-O-glucuronide, berberine, palmatine, and Chrysin-7-O-glucuronide were all directly linked with reductions in intestinal SN-38 levels. We therefore speculate that these compounds are the primary bioactive components of BXD, suggesting that they offer protection against CPT-11-induced diarrhea. Conclusion: By utilizing UPLC to analyze SN-38 levels in mice treated with a variety of herbal combinations, we were able to effectively explore BXD spectrum-effect relationships and to thereby establish the components of this medicinal preparation that were bioactive and capable of preventing CPT-11-induced diarrhea in mice. This and similar spectrum-effect studies represent a robust means of exploring the mechanistic basis for the pharmacological activity of TCM preparations.

Anticancer potential of phytochemicals from Oroxylum indicum targeting Lactate Dehydrogenase A through bioinformatic approach

Toxicol Rep 2022 Dec 14;10:56-75.PMID:36583135DOI:10.1016/j.toxrep.2022.12.007.

In recent years, small molecule inhibition of LDHA (Lactate Dehydrogenase A) has evolved as an appealing option for anticancer therapy. LDHA catalyzes the interconversion of pyruvate and lactate in the glycolysis pathway to play a crucial role in aerobic glycolysis. Therefore, in the current investigation LDHA was targeted with bioactive phytochemicals of an ethnomedicinally important plant species Oroxylum indicum (L.) Kurz. A total of 52 phytochemicals were screened against LDHA protein through molecular docking, ADMET (Absorption, Distribution, Metabolism, Excretion and Toxicity) assay and molecular dynamics simulation to reveal three potential lead compounds such as Chrysin-7-O-glucuronide (-8.2 kcal/mol), Oroxindin (-8.1 kcal/mol) and Oroxin A (-8.0 kcal/mol). ADMET assay unveiled favorable pharmacokinetic, pharmacodynamic and toxicity properties for all the lead compounds. Molecular dynamics simulation exhibited significant conformational stability and compactness. MM/GBSA free binding energy calculations further corroborated the selection of top candidates where Oroxindin (-46.47 kcal/mol) was found to be better than Chrysin-7-O-glucuronide (-45.72 kcal/mol) and Oroxin A (-37.25 kcal/mol). Aldolase reductase and Xanthine dehydrogenase enzymes were found as potential drug targets and Esculin, the FDA approved drug was identified as structurally analogous to Oroxindin. These results could drive in establishing novel medications targeting LDHA to fight cancer.

Inhibitory effects against α-glucosidase and α-amylase of the flavonoids-rich extract from Scutellaria baicalensis shoots and interpretation of structure-activity relationship of its eight flavonoids by a refined assign-score method

Chem Cent J 2018 Jul 12;12(1):82.PMID:30003449DOI:10.1186/s13065-018-0445-y.

A flavonoids-rich extract of Scutellaria baicalensis shoots and its eight high content flavonoids were investigated for their inhibitory effects against α-glucosidase and α-amylase. Results show that abilities of the extract in inhibiting the two enzymes were obviously higher than those of acarbose. Moreover, inhibitory abilities of all the eight individual flavonoids against the two enzymes show exactly a same order (i.e., apigenin > baicalein > scutellarin > chrysin > apigenin-7-O-glucuronide > baicalin > Chrysin-7-O-glucuronide > isocarthamidin-7-O-glucuronide), and their structure-activity relationship could be well-interpretated by the refined assign-score method. Furthermore, based on the inhibitory abilities and their contents in the extract, it was found that the eight flavonoids made predominant contributions, among which baicalein and scutellarin played roles as preliminary contributors, to overall inhibitory effects of the extract against the two enzymes. Beyond these, contributions of the eight flavonoids to the overall enzyme inhibitory activity were compared with those to the overall antioxidant activity characterized in our recent study, and it could be inferred that within the basic flavonoid structure the hydroxyl on C-4' of ring B was more effective than that on C-6 of ring A in enzyme inhibitory activities while they behaved inversely in antioxidant activities; scutellarin and apigenin contributed more to the overall enzyme inhibitory activity, and baicalin and scutellarin, to the overall antioxidant activity of the extract; and flavonoids of the extract, apart from directly inhibiting enzymes, might also be conducive to curing type 2 diabetes via scavenging various free radicals caused by increased oxidative stresses.