Vexibinol
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MedKoo CAT#: 584536

CAS#: 97938-30-2

Description: Vexibinol is a flavonoid that has been found in S. flavescens and has diverse biological activities. It is active against 21 strains of methicillin-resistant S. aureus (MRSA; MICs = 3.13-6.25 µg/ml) and inhibits the activities of α-glucosidase and β-amylase (Kis = 5.6 and 30.6 µM, respectively). Vexibinol is cytotoxic to HL-60 and HepG2 cancer cells (IC50s = 12.5 and 13.3 µM, respectively) and induces apoptosis in HL-60 cells when used at concentrations of 10 or 25 µM. It reduces LPS-induced production of prostaglandin E2 (PGE2) in RAW 264.7 cells when used at concentrations ranging from 1 to 50 µM. Vexibinol (250 mg/kg) inhibits carrageenan-induced paw edema in rats.

Chemical Structure

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Vexibinol
CAS# 97938-30-2
Instruction

Theoretical Analysis

MedKoo Cat#: 584536
Name: Vexibinol
CAS#: 97938-30-2
Chemical Formula: C25H28O6
Exact Mass: 424.19
Molecular Weight: 424.493
Elemental Analysis: C, 70.74; H, 6.65; O, 22.61

Price and Availability

Size Price Availability Quantity
1mg USD 225 2 Weeks
5mg USD 460 2 Weeks
10mg USD 725 2 Weeks
25mg USD 1175 2 Weeks
Bulk inquiry

Synonym: Vexibinol; (-)-Vexibinol; Kushenol F; Kushnol F; Norkurarinone; Sophoraflavanone G;

IUPAC/Chemical Name: 4H-1-Benzopyran-4-one, 2,3-dihydro-5,7-dihydroxy-2-(2,4-dihydroxyphenyl)-8-(5-methyl-2-(1-methylethenyl)-4-hexenyl)-, (S-(R*,S*))-

InChi Key: XRYVAQQLDYTHCL-CMJOXMDJSA-N

InChi Code: InChI=1S/C25H28O6/c1-13(2)5-6-15(14(3)4)9-18-20(28)11-21(29)24-22(30)12-23(31-25(18)24)17-8-7-16(26)10-19(17)27/h5,7-8,10-11,15,23,26-29H,3,6,9,12H2,1-2,4H3/t15-,23+/m1/s1

SMILES Code: O=C1C[C@@H](C2=CC=C(O)C=C2O)OC3=C(C[C@H](C(C)=C)C/C=C(C)\C)C(O)=CC(O)=C13

Appearance: Solid powder

Purity: >98% (or refer to the Certificate of Analysis)

Shipping Condition: Shipped under ambient temperature as non-hazardous chemical. This product is stable enough for a few weeks during ordinary shipping and time spent in Customs.

Storage Condition: Dry, dark and at 0 - 4 C for short term (days to weeks) or -20 C for long term (months to years).

Solubility: Soluble in DMSO

Shelf Life: >3 years if stored properly

Drug Formulation: This drug may be formulated in DMSO

Stock Solution Storage: 0 - 4 C for short term (days to weeks), or -20 C for long term (months).

HS Tariff Code: 2934.99.03.00

More Info:

Biological target:
In vitro activity:
In vivo activity:

Solubility Data

Solvent Max Conc. mg/mL Max Conc. mM
Solubility
DMF 30.0 70.67
DMSO 30.0 70.67
Ethanol 20.0 47.12

Preparing Stock Solutions

The following data is based on the product molecular weight 424.49 Batch specific molecular weights may vary from batch to batch due to the degree of hydration, which will affect the solvent volumes required to prepare stock solutions.

Recalculate based on batch purity %
Concentration / Solvent Volume / Mass 1 mg 5 mg 10 mg
1 mM 1.15 mL 5.76 mL 11.51 mL
5 mM 0.23 mL 1.15 mL 2.3 mL
10 mM 0.12 mL 0.58 mL 1.15 mL
50 mM 0.02 mL 0.12 mL 0.23 mL
Formulation protocol:
In vitro protocol:
In vivo protocol:

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1: Chen MH, Gu YY, Zhang AL, Sze DM, Mo SL, May BH. Biological effects and mechanisms of matrine and other constituents of Sophora flavescens in colorectal cancer. Pharmacol Res. 2021 Sep;171:105778. doi: 10.1016/j.phrs.2021.105778. Epub 2021 Jul 20. PMID: 34298110.

2: Liu HR, Liu YM, Hou TL, Li CT, Zhang QZ. Antiparasitic Efficacy of Crude Plant Extracts and Compounds Purified from Plants against the Fish Monogenean Neobenedenia girellae. J Aquat Anim Health. 2021 Apr 27. doi: 10.1002/aah.10128. Epub ahead of print. PMID: 33905159.

3: Soltani S, Boozari M, Nejad Ebrahimi S, Amin GR, Iranshahi M. Histone Deacetylase Inhibitory and Cytotoxic Activities of the Constituents from the Roots of Sophora Pachycarpa. Iran J Pharm Res. 2020 Fall;19(4):51-58. doi: 10.22037/ijpr.2020.112442.13760. PMID: 33841520; PMCID: PMC8019873.

4: Sun ZL, Sun SC, He JM, Lan JE, Gibbons S, Mu Q. Synergism of sophoraflavanone G with norfloxacin against effluxing antibiotic-resistant Staphylococcus aureus. Int J Antimicrob Agents. 2020 Sep;56(3):106098. doi: 10.1016/j.ijantimicag.2020.106098. Epub 2020 Jul 21. PMID: 32707171.

5: Wang H, Tong Y, Xiao D, Xia B. Involvement of mTOR-related signaling in antidepressant effects of Sophoraflavanone G on chronically stressed mice. Phytother Res. 2020 Sep;34(9):2246-2257. doi: 10.1002/ptr.6675. Epub 2020 Apr 3. PMID: 32246575.

6: Chen H, Yang J, Hao J, Lv Y, Chen L, Lin Q, Yuan J, Yang X. A Novel Flavonoid Kushenol Z from Sophora flavescens Mediates mTOR Pathway by Inhibiting Phosphodiesterase and Akt Activity to Induce Apoptosis in Non-Small-Cell Lung Cancer Cells. Molecules. 2019 Dec 4;24(24):4425. doi: 10.3390/molecules24244425. PMID: 31817093; PMCID: PMC6943755.

7: Wang R, Deng X, Gao Q, Wu X, Han L, Gao X, Zhao S, Chen W, Zhou R, Li Z, Bai C. Sophora alopecuroides L.: An ethnopharmacological, phytochemical, and pharmacological review. J Ethnopharmacol. 2020 Feb 10;248:112172. doi: 10.1016/j.jep.2019.112172. Epub 2019 Aug 20. PMID: 31442619.

8: Yang Z, Wang Y, Cheng J, Shan B, Wang Y, Wang R, Hou L. Solid self- microemulsifying drug delivery system of Sophoraflavanone G: Prescription optimization and pharmacokinetic evaluation. Eur J Pharm Sci. 2019 Aug 1;136:104953. doi: 10.1016/j.ejps.2019.06.007. Epub 2019 Jun 5. PMID: 31175944.

9: Huang WC, Gu PY, Fang LW, Huang YL, Lin CF, Liou CJ. Sophoraflavanone G from Sophora flavescens induces apoptosis in triple-negative breast cancer cells. Phytomedicine. 2019 Aug;61:152852. doi: 10.1016/j.phymed.2019.152852. Epub 2019 Jan 29. PMID: 31035052.

10: Boozari M, Nejad Ebrahimi S, Soltani S, Tayarani-Najaran Z, Emami SA, Asili J, Iranshahi M. Absolute configuration and anti-cancer effect of prenylated flavonoids and flavonostilbenes from Sophora pachycarpa: Possible involvement of Wnt signaling pathway. Bioorg Chem. 2019 Apr;85:498-504. doi: 10.1016/j.bioorg.2019.01.051. Epub 2019 Feb 6. PMID: 30802806.

11: Boozari M, Soltani S, Iranshahi M. Biologically active prenylated flavonoids from the genus Sophora and their structure-activity relationship-A review. Phytother Res. 2019 Mar;33(3):546-560. doi: 10.1002/ptr.6265. Epub 2019 Jan 16. PMID: 30652369.

12: Sekiguchi F, Fujita T, Deguchi T, Yamaoka S, Tomochika K, Tsubota M, Ono S, Horaguchi Y, Ichii M, Ichikawa M, Ueno Y, Koike N, Tanino T, Nguyen HD, Okada T, Nishikawa H, Yoshida S, Ohkubo T, Toyooka N, Murata K, Matsuda H, Kawabata A. Blockade of T-type calcium channels by 6-prenylnaringenin, a hop component, alleviates neuropathic and visceral pain in mice. Neuropharmacology. 2018 Aug;138:232-244. doi: 10.1016/j.neuropharm.2018.06.020. Epub 2018 Jun 18. PMID: 29913186.

13: Herrmann FC, Sivakumar N, Jose J, Costi MP, Pozzi C, Schmidt TJ. In Silico Identification and In Vitro Evaluation of Natural Inhibitors of Leishmania major Pteridine Reductase I. Molecules. 2017 Dec 6;22(12):2166. doi: 10.3390/molecules22122166. PMID: 29211037; PMCID: PMC6149668.

14: Sze A, Olagnier D, Hadj SB, Han X, Tian XH, Xu HT, Yang L, Shi Q, Wang P, Wainberg MA, Wu JH, Lin R. Sophoraflavenone G Restricts Dengue and Zika Virus Infection via RNA Polymerase Interference. Viruses. 2017 Oct 3;9(10):287. doi: 10.3390/v9100287. PMID: 28972551; PMCID: PMC5691638.

15: Sun ZL, He JM, Lan JE, Mu Q. High-Speed Counter-Current Chromatography with an Online Storage Technique for the Preparative Isolation and Purification of Dihydroflavonoids from Sophora alopecuroides L. Phytochem Anal. 2017 Nov;28(6):496-504. doi: 10.1002/pca.2698. Epub 2017 Jun 6. PMID: 28589595.

16: Qiu ZC, Dong XL, Dai Y, Xiao GK, Wang XL, Wong KC, Wong MS, Yao XS. Discovery of a New Class of Cathepsin K Inhibitors in Rhizoma Drynariae as Potential Candidates for the Treatment of Osteoporosis. Int J Mol Sci. 2016 Dec 16;17(12):2116. doi: 10.3390/ijms17122116. PMID: 27999266; PMCID: PMC5187916.

17: Wang H, Chen L, Zhang L, Gao X, Wang Y, Weiwei T. Protective effect of Sophoraflavanone G on streptozotocin (STZ)-induced inflammation in diabetic rats. Biomed Pharmacother. 2016 Dec;84:1617-1622. doi: 10.1016/j.biopha.2016.10.113. Epub 2016 Nov 7. PMID: 27832995.

18: Guo C, Yang L, Wan CX, Xia YZ, Zhang C, Chen MH, Wang ZD, Li ZR, Li XM, Geng YD, Kong LY. Anti-neuroinflammatory effect of Sophoraflavanone G from Sophora alopecuroides in LPS-activated BV2 microglia by MAPK, JAK/STAT and Nrf2/HO-1 signaling pathways. Phytomedicine. 2016 Dec 1;23(13):1629-1637. doi: 10.1016/j.phymed.2016.10.007. Epub 2016 Oct 14. PMID: 27823627.

19: Yang Z, Zhang W, Li X, Shan B, Liu J, Deng W. Determination of sophoraflavanone G and kurarinone in rat plasma by UHPLC-MS/MS and its application to a pharmacokinetic study. J Sep Sci. 2016 Nov;39(22):4344-4353. doi: 10.1002/jssc.201600681. Epub 2016 Nov 3. PMID: 27808456.

20: Oh J, Liu H, Park HB, Ferreira D, Jeong GS, Hamann MT, Doerksen RJ, Na M. In silico investigation of lavandulyl flavonoids for the development of potent fatty acid synthase-inhibitory prototypes. Biochim Biophys Acta Gen Subj. 2017 Jan;1861(1 Pt A):3180-3188. doi: 10.1016/j.bbagen.2016.08.001. Epub 2016 Aug 13. PMID: 27531709; PMCID: PMC5918680.