Vexibinol

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

MedKoo CAT#: 584536

CAS#: 97938-30-2

Description: Vexibinol, one of the flavanols found in Sophora, has an inhibitory effect on gastric ulcers.


Price and Availability

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Vexibinol is not in stock, may be available through custom synthesis. For cost-effective reason, minimum 1 gram order is requested. The product will be characterized by NMR, HPLC and MS analysis. Purity (HPLC) is usually >98%. CoA, QC data, MSDS will be provided when product is successfully made. The estimated lead time is 2-3 months. Please send email to sales@medkoo.com to inquire quote.


Chemical Structure

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Theoretical Analysis

MedKoo Cat#: 584536
Name: Vexibinol
CAS#: 97938-30-2
Chemical Formula: C25H28O6
Exact Mass: 424.1886
Molecular Weight: 424.493
Elemental Analysis: C, 70.74; H, 6.65; O, 22.61


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


Technical Data

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).

Harmonized System Code:
2934.99.03.00


References

1: 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. PubMed PMID: 24894298.

2: Wun ZY, Lin CF, Huang WC, Huang YL, Xu PY, Chang WT, Wu SJ, Liou CJ. Anti-inflammatory effect of sophoraflavanone G isolated from Sophora flavescens in lipopolysaccharide-stimulated mouse macrophages. Food Chem Toxicol. 2013 Dec;62:255-61. doi: 10.1016/j.fct.2013.08.072. Epub 2013 Sep 2. PubMed PMID: 24007739.

3: Kim DW, Chi YS, Son KH, Chang HW, Kim JS, Kang SS, Kim HP. Effects of sophoraflavanone G, a prenylated flavonoid from Sophora flavescens, on cyclooxygenase-2 and in vivo inflammatory response. Arch Pharm Res. 2002 Jun;25(3):329-35. PubMed PMID: 12135106.

4: 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). pii: E2116. doi: 10.3390/ijms17122116. PubMed PMID: 27999266; PubMed Central PMCID: PMC5187916.

5: Shitan N, Kamimoto Y, Minami S, Kubo M, Ito K, Moriyasu M, Yazaki K. A tolerance gene for prenylated flavonoid encodes a 26S proteasome regulatory subunit in Sophora flavescens. Biosci Biotechnol Biochem. 2011;75(5):982-4. Epub 2011 May 20. PubMed PMID: 21597174.

6: 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. PubMed PMID: 24490565.

7: 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. PubMed PMID: 27808456.

8: 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. PubMed PMID: 27351825.

9: 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. PubMed PMID: 27832995.

10: Yamahara J, Mochizuki M, Chisaka T, Fujimura H, Tamai Y. The antiulcer action of sophora and the active constituent in Sophora. II. The antiulcer action of vexibinol. Chem Pharm Bull (Tokyo). 1990 Apr;38(4):1039-44. PubMed PMID: 2379277.

11: Tsuchiya H, Iinuma M. Reduction of membrane fluidity by antibacterial sophoraflavanone G isolated from Sophora exigua. Phytomedicine. 2000 Apr;7(2):161-5. PubMed PMID: 10839220.

12: Yamamoto H, Yatou A, Inoue K. 8-dimethylallylnaringenin 2'-hydroxylase, the crucial cytochrome P450 mono-oxygenase for lavandulylated flavanone formation in Sophora flavescens cultured cells. Phytochemistry. 2001 Nov;58(5):671-6. PubMed PMID: 11672730.

13: Yu Q, Cheng N, Ni X. Identifying 2 prenylflavanones as potential hepatotoxic compounds in the ethanol extract of Sophora flavescens. J Food Sci. 2013 Nov;78(11):T1830-4. doi: 10.1111/1750-3841.12275. Epub 2013 Oct 8. PubMed PMID: 24245902.

14: 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. PubMed PMID: 27111520.

15: Chong ES, Hwang GB, Nho CW, Kwon BM, Lee JE, Seo S, Bae GN, Jung JH. Antimicrobial durability of air filters coated with airborne Sophora flavescens nanoparticles. Sci Total Environ. 2013 Feb 1;444:110-4. doi: 10.1016/j.scitotenv.2012.11.075. Epub 2012 Dec 21. PubMed PMID: 23262327.

16: Yamahara J, Kobayashi G, Iwamoto M, Chisaka T, Fujimura H, Takaishi Y, Yoshida M, Tomimatsu T, Tamai Y. Vasodilatory active principles of Sophora flavescens root. J Ethnopharmacol. 1990 Apr;29(1):79-85. PubMed PMID: 2161063.

17: 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. PubMed PMID: 27823627.

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. PubMed PMID: 26916921.

19: Kim BH, Won C, Lee YH, Choi JS, Noh KH, Han S, Lee H, Lee CS, Lee DS, Ye SK, Kim MH. Sophoraflavanone G induces apoptosis of human cancer cells by targeting upstream signals of STATs. Biochem Pharmacol. 2013 Oct 1;86(7):950-9. doi: 10.1016/j.bcp.2013.08.009. Epub 2013 Aug 17. PubMed PMID: 23962443.

20: Kim CS, Park SN, Ahn SJ, Seo YW, Lee YJ, Lim YK, Freire MO, Cho E, Kook JK. Antimicrobial effect of sophoraflavanone G isolated from Sophora flavescens against mutans streptococci. Anaerobe. 2013 Feb;19:17-21. doi: 10.1016/j.anaerobe.2012.11.003. Epub 2012 Nov 23. PubMed PMID: 23178373.