Vescalagin | CAS#36001-47-5 | anti-diabetic

MedKoo Cat#: 585368 | Name: Vescalagin

Description:

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

Vescalagin is isolated from Pink wax apple fruit, and has therapeutic potential in preventing the progression of diabetes mellitus by reducing hepatic protein expression involved in inflammation pathways while up-regulating expression of hepatic insulin signaling-related proteins..

Chemical Structure

Vescalagin

CAS#36001-47-5

Theoretical Analysis

MedKoo Cat#: 585368

Name: Vescalagin

CAS#: 36001-47-5

Chemical Formula: C41H26O26

Exact Mass: 934.0712

Molecular Weight: 934.63

Elemental Analysis: C, 52.69; H, 2.80; O, 44.51

Price and Availability

This product is currently not in stock but may be available through custom synthesis. To ensure cost efficiency, the minimum order quantity is 1 gram. The estimated lead time is 2 to 4 months, with pricing dependent on the complexity of the synthesis (typically high for intricate chemistries). Quotes for quantities below 1 gram will not be provided. To request a quote, please click the button below. Note: If this product becomes available in stock in the future, pricing will be listed accordingly.

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Related CAS #

No Data

Synonym

Vescalagin

IUPAC/Chemical Name

7,8,9,12,13,14,25,26,27,30,31,32,35,36,37,46-hexadecahydroxy-3,18,21,41,43-pentaoxanonacyclo[27.13.3.138,42.02,20.05,10.011,16.023,28.033,45.034,39]hexatetraconta-5,7,9,11,13,15,23,25,27,29(45),30,32,34(39),35,37-pentadecaene-4,17,22,40,44-pentone

InChi Key

UDYKDZHZAKSYCO-UHFFFAOYSA-N

InChi Code

InChI=1S/C41H26O26/c42-8-1-5-12(24(48)21(8)45)13-6(2-9(43)22(46)25(13)49)39(60)65-34-11(4-63-37(5)58)64-38(59)7-3-10(44)23(47)26(50)14(7)15-18-16(28(52)32(56)27(15)51)17-19-20(30(54)33(57)29(17)53)31(55)35(66-41(19)62)36(34)67-40(18)61/h1-3,11,31,34-36,42-57H,4H2

SMILES Code

O=C(C1=CC(O)=C(O)C(O)=C1C2=C(O)C(O)=C(O)C=C2C(OCC3OC(C4=CC(O)=C(O)C(O)=C4C(C(O)=C(O)C(O)=C5C6=C7C8=C(O)C(O)=C6O)=C5C(O9)=O)=O)=O)OC3C9C(C8O)OC7=O

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

2934.99.9001

More Info

Instruction

View handling instruction

Preparing Stock Solutions

The following data is based on the product molecular weight 934.63 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: Huang DW, Chang WC, Wu JS, Shih RW, Shen SC. Vescalagin from Pink Wax Apple [Syzygium samarangense (Blume) Merrill and Perry] Alleviates Hepatic Insulin Resistance and Ameliorates Glycemic Metabolism Abnormality in Rats Fed a High-Fructose Diet. J Agric Food Chem. 2016 Feb 10;64(5):1122-9. doi: 10.1021/acs.jafc.5b05558. Epub 2016 Feb 1. PubMed PMID: 26800576. 2: Kamada Y, Yakabu H, Ichiba T, Tamanaha A, Shimoji M, Kato M, Norimoto C, Yamashiro R, Miyagi I, Sakudo A, Tanaka Y. Castalagin and vescalagin purified from leaves of Syzygium samarangense (Blume) Merrill & L.M. Perry: Dual inhibitory activity against PARP1 and DNA topoisomerase II. Fitoterapia. 2018 Sep;129:94-101. doi: 10.1016/j.fitote.2018.06.015. Epub 2018 Jun 19. PubMed PMID: 29928967. 3: Matsuo Y, Wakamatsu H, Omar M, Tanaka T. Reinvestigation of the stereochemistry of the C-glycosidic ellagitannins, vescalagin and castalagin. Org Lett. 2015 Jan 2;17(1):46-9. doi: 10.1021/ol503212v. Epub 2014 Dec 12. PubMed PMID: 25496565. 4: García-Estévez I, Gavara R, Alcalde-Eon C, Rivas-Gonzalo JC, Quideau S, Escribano-Bailón MT, Pina F. Thermodynamic and kinetic properties of a new myrtillin-vescalagin hybrid pigment. J Agric Food Chem. 2013 Nov 27;61(47):11569-78. doi: 10.1021/jf403319u. Epub 2013 Nov 15. PubMed PMID: 24164407. 5: Vivas N, Laguerre M, Pianet de Boissel I, Vivas de Gaulejac N, Nonier MF. Conformational interpretation of vescalagin and castalagin physicochemical properties. J Agric Food Chem. 2004 Apr 7;52(7):2073-8. PubMed PMID: 15053554. 6: Shen SC, Chang WC. Hypotriglyceridemic and hypoglycemic effects of vescalagin from Pink wax apple [Syzygium samarangense (Blume) Merrill and Perry cv. Pink] in high-fructose diet-induced diabetic rats. Food Chem. 2013 Jan 15;136(2):858-63. doi: 10.1016/j.foodchem.2012.08.037. Epub 2012 Aug 30. PubMed PMID: 23122137. 7: García-Estévez I, Jacquet R, Alcalde-Eon C, Rivas-Gonzalo JC, Escribano-Bailón MT, Quideau S. Hemisynthesis and structural and chromatic characterization of delphinidin 3-O-glucoside-vescalagin hybrid pigments. J Agric Food Chem. 2013 Nov 27;61(47):11560-8. doi: 10.1021/jf4033188. Epub 2013 Nov 15. PubMed PMID: 24215431. 8: Auzanneau C, Montaudon D, Jacquet R, Puyo S, Pouységu L, Deffieux D, Elkaoukabi-Chaibi A, De Giorgi F, Ichas F, Quideau S, Pourquier P. The polyphenolic ellagitannin vescalagin acts as a preferential catalytic inhibitor of the α isoform of human DNA topoisomerase II. Mol Pharmacol. 2012 Jul;82(1):134-41. doi: 10.1124/mol.111.077537. Epub 2012 Apr 23. PubMed PMID: 22528119. 9: Chang WC, Shen SC, Wu JS. Protective effects of vescalagin from pink wax apple [Syzygium samarangense (Blume) Merrill and Perry] fruit against methylglyoxal-induced inflammation and carbohydrate metabolic disorder in rats. J Agric Food Chem. 2013 Jul 24;61(29):7102-9. doi: 10.1021/jf4020284. Epub 2013 Jul 15. PubMed PMID: 23819528. 10: Puech JL, Mertz C, Michon V, Le Guernevé C, Doco T, Hervé Du Penhoat C. Evolution of castalagin and vescalagin in ethanol solutions. Identification of new derivatives. J Agric Food Chem. 1999 May;47(5):2060-6. PubMed PMID: 10552496. 11: Quideau S, Douat-Casassus C, Delannoy López DM, Di Primo C, Chassaing S, Jacquet R, Saltel F, Genot E. Binding of filamentous actin and winding into fibrillar aggregates by the polyphenolic C-glucosidic ellagitannin vescalagin. Angew Chem Int Ed Engl. 2011 May 23;50(22):5099-104. doi: 10.1002/anie.201006712. Epub 2011 Apr 27. PubMed PMID: 21538732. 12: Mannelli F, Daghio M, Alves SP, Bessa RJB, Minieri S, Giovannetti L, Conte G, Mele M, Messini A, Rapaccini S, Viti C, Buccioni A. Effects of Chestnut Tannin Extract, Vescalagin and Gallic Acid on the Dimethyl Acetals Profile and Microbial Community Composition in Rumen Liquor: An In Vitro Study. Microorganisms. 2019 Jul 18;7(7). pii: E202. doi: 10.3390/microorganisms7070202. PubMed PMID: 31323805; PubMed Central PMCID: PMC6680752. 13: Matsuo Y. Study of the Stereochemistry and Oxidation Mechanism of Plant Polyphenols, Assisted by Computational Chemistry. Yakugaku Zasshi. 2017;137(3):347-354. doi: 10.1248/yakushi.16-00207. Review. Japanese. PubMed PMID: 28250332. 14: Yamada H, Wakamori S, Hirokane T, Ikeuchi K, Matsumoto S. Structural Revisions in Natural Ellagitannins. Molecules. 2018 Jul 30;23(8). pii: E1901. doi: 10.3390/molecules23081901. Review. PubMed PMID: 30061530; PubMed Central PMCID: PMC6222896. 15: Georgess D, Spuul P, Le Clainche C, Le Nihouannen D, Fremaux I, Dakhli T, Delannoy López DM, Deffieux D, Jurdic P, Quideau S, Génot E. Anti-osteoclastic effects of C-glucosidic ellagitannins mediated by actin perturbation. Eur J Cell Biol. 2018 Nov;97(8):533-545. doi: 10.1016/j.ejcb.2018.09.003. Epub 2018 Sep 24. PubMed PMID: 30287085. 16: Soares S, Silva MS, García-Estevez I, Groβmann P, Brás N, Brandão E, Mateus N, de Freitas V, Behrens M, Meyerhof W. Human Bitter Taste Receptors Are Activated by Different Classes of Polyphenols. J Agric Food Chem. 2018 Aug 22;66(33):8814-8823. doi: 10.1021/acs.jafc.8b03569. Epub 2018 Aug 14. PubMed PMID: 30056706. 17: Silva MS, García-Estévez I, Brandão E, Mateus N, de Freitas V, Soares S. Molecular Interaction Between Salivary Proteins and Food Tannins. J Agric Food Chem. 2017 Aug 9;65(31):6415-6424. doi: 10.1021/acs.jafc.7b01722. Epub 2017 Jun 19. PubMed PMID: 28589723. 18: García-Estévez I, Alcalde-Eon C, Martínez-Gil AM, Rivas-Gonzalo JC, Escribano-Bailón MT, Nevares I, Del Alamo-Sanza M. An Approach to the Study of the Interactions between Ellagitannins and Oxygen during Oak Wood Aging. J Agric Food Chem. 2017 Aug 9;65(31):6369-6378. doi: 10.1021/acs.jafc.7b02080. Epub 2017 Jun 1. PubMed PMID: 28534630. 19: Navarro M, Kontoudakis N, Canals JM, García-Romero E, Gómez-Alonso S, Zamora F, Hermosín-Gutiérrez I. Improved method for the extraction and chromatographic analysis on a fused-core column of ellagitannins found in oak-aged wine. Food Chem. 2017 Jul 1;226:23-31. doi: 10.1016/j.foodchem.2017.01.043. Epub 2017 Jan 11. PubMed PMID: 28254015. 20: Piwowarski JP, Kiss AK. C-glucosidic ellagitannins from Lythri herba (European Pharmacopoeia): chromatographic profile and structure determination. Phytochem Anal. 2013 Jul-Aug;24(4):336-48. doi: 10.1002/pca.2415. Epub 2012 Dec 28. PubMed PMID: 23280650.