Vexibinol | CAS#97938-30-2 | Diverse flavanoid

MedKoo Cat#: 584536 | Name: Vexibinol

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Description:

WARNING: This product is for research use only, not for human or veterinary use.

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

Vexibinol

CAS#97938-30-2

Theoretical Analysis

MedKoo Cat#: 584536

Name: Vexibinol

CAS#: 97938-30-2

Chemical Formula: C25H28O6

Exact Mass: 424.1886

Molecular Weight: 424.49

Elemental Analysis: C, 70.74; H, 6.65; O, 22.61

Price and Availability

Size	Price	Availability
1mg	USD 350.00	2 Weeks
5mg	USD 550.00	2 Weeks
10mg	USD 850.00	2 Weeks
25mg	USD 1,250.00	2 Weeks

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Related CAS #

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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

Instruction

View handling instruction

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

Note: There can be variations in solubility for the same chemical from different vendors or different batches from the same vendor. The following factors can affect the solubility of the same chemical: solvent used for crystallization, residual solvent content, polymorphism, salt versus free form, degree of hydration, solvent temperature. Please use the solubility data as a reference only. Warming and sonication will facilitate dissolving. Still have questions? Please contact our Technical Support scientists.

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.

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

1: Lee TH, Chen JL, Tsai MM, Wu YH, Tseng HC, Cheng LC, Shanmugam V, Hsieh HL. Protective Effects of Sophoraflavanone G by Inhibiting TNF-α-Induced MMP-9-Mediated Events in Brain Microvascular Endothelial Cells. Int J Mol Sci. 2023 Dec 24;25(1):283. doi: 10.3390/ijms25010283. PMID: 38203454; PMCID: PMC10779338. 2: Wang MC, Huang WC, Chen LC, Yeh KW, Lin CF, Liou CJ. Sophoraflavanone G from Sophora flavescens Ameliorates Allergic Airway Inflammation by Suppressing Th2 Response and Oxidative Stress in a Murine Asthma Model. Int J Mol Sci. 2022 May 29;23(11):6104. doi: 10.3390/ijms23116104. PMID: 35682783; PMCID: PMC9181790. 3: Fu YW, Liu WD, Chen HZ, Lin DJ, Hou TL, Guo SQ, Zhang QZ. Antiparasitical efficacy of sophoraflavanone G isolated from Sophora flavescens against parasitic protozoa Ichthyophthirius multifiliis. Vet Parasitol. 2022 Jun;306:109731. doi: 10.1016/j.vetpar.2022.109731. Epub 2022 May 22. PMID: 35643574. 4: Cheng W, Liu D, Guo M, Li H, Wang Q. Sophoraflavanone G suppresses the progression of triple-negative breast cancer via the inactivation of EGFR- PI3K-AKT signaling. Drug Dev Res. 2022 Aug;83(5):1138-1151. doi: 10.1002/ddr.21938. Epub 2022 Apr 15. PMID: 35426453. 5: Wu CP, Li YQ, Hung TH, Chang YT, Huang YH, Wu YS. Sophoraflavanone G Resensitizes ABCG2-Overexpressing Multidrug-Resistant Non-Small-Cell Lung Cancer Cells to Chemotherapeutic Drugs. J Nat Prod. 2021 Sep 24;84(9):2544-2553. doi: 10.1021/acs.jnatprod.1c00584. Epub 2021 Sep 8. PMID: 34496204. 6: 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. 7: 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. 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, 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. 11: 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. 12: 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. 13: 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. 14: 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. 15: 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. 16: Guo C, Yang L, Luo J, Zhang C, Xia Y, Ma T, Kong L. Sophoraflavanone G from Sophora alopecuroides inhibits lipopolysaccharide-induced inflammation in RAW264.7 cells by targeting PI3K/Akt, JAK/STAT and Nrf2/HO-1 pathways. Int Immunopharmacol. 2016 Sep;38:349-56. doi: 10.1016/j.intimp.2016.06.021. Epub 2016 Jun 25. PMID: 27351825. 17: Cha SM, Cha JD, Jang EJ, Kim GU, Lee KY. Sophoraflavanone G prevents Streptococcus mutans surface antigen I/II-induced production of NO and PGE2 by inhibiting MAPK-mediated pathways in RAW 264.7 macrophages. Arch Oral Biol. 2016 Aug;68:97-104. doi: 10.1016/j.archoralbio.2016.04.001. Epub 2016 Apr 4. PMID: 27111520. 18: Li ZY, Huang WC, Tu RS, Gu PY, Lin CF, Liou CJ. Sophoraflavanone G Induces Apoptosis in Human Leukemia Cells and Blocks MAPK Activation. Am J Chin Med. 2016;44(1):165-76. doi: 10.1142/S0192415X16500117. PMID: 26916921. 19: Chen P, Zhang X, Huang T, Yu Q, Cheng N. Metabolism of the hepatotoxic compound sophoraflavanone G in rat liver microsomes. J Food Sci. 2014 Jul;79(7):T1462-8. doi: 10.1111/1750-3841.12501. Epub 2014 Jun 3. PMID: 24894298. 20: Zhang C, Ma Y, Gao HM, Liu XQ, Chen LM, Zhang QW, Wang ZM, Li AP. [Non- alkaloid components from Sophora flavescens]. Zhongguo Zhong Yao Za Zhi. 2013 Oct;38(20):3520-4. Chinese. PMID: 24490565.