Vicenin 2

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

MedKoo CAT#: 562968

CAS#: 23666-13-9

Description: Vicenin 2 is an inhibitor of α-glucosidase, PTP1B, and RLAR.


Price and Availability

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Vicenin 2 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#: 562968
Name: Vicenin 2
CAS#: 23666-13-9
Chemical Formula: C27H30O15
Exact Mass: 594.1585
Molecular Weight: 594.52
Elemental Analysis: C, 54.55; H, 5.09; O, 40.37


Synonym: Vicenin 2; Vicenin-2; Vicenin2; Apigenin-6,8-di-C-glycoside;

IUPAC/Chemical Name: 5,7-Dihydroxy-2-(4-hydroxyphenyl)-6,8-bis[(2S,3R,4R,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]chromen-4-one

InChi Key: FIAAVMJLAGNUKW-VQVVXJKKSA-N

InChi Code: InChI=1S/C27H30O15/c28-6-12-17(32)21(36)23(38)26(41-12)15-19(34)14-10(31)5-11(8-1-3-9(30)4-2-8)40-25(14)16(20(15)35)27-24(39)22(37)18(33)13(7-29)42-27/h1-5,12-13,17-18,21-24,26-30,32-39H,6-7H2/t12-,13-,17-,18-,21+,22+,23-,24-,26+,27+/m1/s1

SMILES Code: O=C1C=C(C2=CC=C(O)C=C2)OC3=C1C(O)=C([C@@H]4O[C@H](CO)[C@@H](O)[C@H](O)[C@H]4O)C(O)=C3[C@@H]5O[C@H](CO)[C@@H](O)[C@H](O)[C@H]5O


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:
>2 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:
293490


References

1: Yang D, Zhang X, Zhang W, Rengarajan T. Vicenin-2 inhibits Wnt/β-catenin signaling and induces apoptosis in HT-29 human colon cancer cell line. Drug Des Devel Ther. 2018 May 18;12:1303-1310. doi: 10.2147/DDDT.S149307. eCollection 2018. PubMed PMID: 29849451; PubMed Central PMCID: PMC5965372.

2: Ferreres F, Gomes NGM, Valentão P, Pereira DM, Gil-Izquierdo A, Araújo L, Silva TC, Andrade PB. Leaves and stem bark from Allophylus africanus P. Beauv.: An approach to anti-inflammatory properties and characterization of their flavonoid profile. Food Chem Toxicol. 2018 May 19;118:430-438. doi: 10.1016/j.fct.2018.05.045. [Epub ahead of print] PubMed PMID: 29787847.

3: Oliveira DR, Todo AH, Rêgo GM, Cerutti JM, Cavalheiro AJ, Rando DGG, Cerutti SM. Flavones-bound in benzodiazepine site on GABA(A) receptor: Concomitant anxiolytic-like and cognitive-enhancing effects produced by Isovitexin and 6-C-glycoside-Diosmetin. Eur J Pharmacol. 2018 Jul 15;831:77-86. doi: 10.1016/j.ejphar.2018.05.004. Epub 2018 May 5. PubMed PMID: 29738701.

4: Makni M, Jemai R, Kriaa W, Chtourou Y, Fetoui H. Citrus limon from Tunisia: Phytochemical and Physicochemical Properties and Biological Activities. Biomed Res Int. 2018 Jan 15;2018:6251546. doi: 10.1155/2018/6251546. eCollection 2018. PubMed PMID: 29568760; PubMed Central PMCID: PMC5820557.

5: Hassan N, Ali A, Withycombe C, Ahluwalia M, Al-Nasseri RH, Tonks A, Morris K. TET-2 up-regulation is associated with the anti-inflammatory action of Vicenin-2. Cytokine. 2018 Aug;108:37-42. doi: 10.1016/j.cyto.2018.03.016. Epub 2018 Mar 19. PubMed PMID: 29567563.

6: Casanova LM, Gu W, Costa SS, Jeppesen PB. Phenolic Substances from Ocimum Species Enhance Glucose-Stimulated Insulin Secretion and Modulate the Expression of Key Insulin Regulatory Genes in Mice Pancreatic Islets. J Nat Prod. 2017 Dec 22;80(12):3267-3275. doi: 10.1021/acs.jnatprod.7b00699. Epub 2017 Dec 1. PubMed PMID: 29192771.

7: de Beer D, Pauck CE, Aucamp M, Liebenberg W, Stieger N, van der Rijst M, Joubert E. Phenolic and physicochemical stability of a functional beverage powder mixture during storage: effect of the microencapsulant inulin and food ingredients. J Sci Food Agric. 2018 Jun;98(8):2925-2934. doi: 10.1002/jsfa.8787. Epub 2018 Jan 30. PubMed PMID: 29168179.

8: Jeong KM, Yang M, Jin Y, Kim EM, Ko J, Lee J. Identification of Major Flavone C-Glycosides and Their Optimized Extraction from Cymbidium kanran Using Deep Eutectic Solvents. Molecules. 2017 Nov 18;22(11). pii: E2006. doi: 10.3390/molecules22112006. PubMed PMID: 29156555.

9: Shaheen U, Shoeib NA, Temraz A, Abdelhady MIS. Flavonoidal Constituents, Antioxidant, Antimicrobial, and Cytotoxic Activities of Dipterygium glaucum Grown in Kingdom of Saudi Arabia. Pharmacogn Mag. 2017 Oct;13(Suppl 3):S484-S488. doi: 10.4103/pm.pm_44_16. Epub 2017 Oct 11. PubMed PMID: 29142403; PubMed Central PMCID: PMC5669086.

10: Chin CY, Jalil J, Ng PY, Ng SF. Development and formulation of Moringa oleifera standardised leaf extract film dressing for wound healing application. J Ethnopharmacol. 2018 Feb 15;212:188-199. doi: 10.1016/j.jep.2017.10.016. Epub 2017 Nov 5. PubMed PMID: 29080829.

11: Moharram FA, El Dib RAEM, Marzouk MS, El-Shenawy SM, Ibrahim HA. New Apigenin Glycoside, Polyphenolic Constituents, Anti-inflammatory and Hepatoprotective Activities of Gaillardia grandiflora and Gaillardia pulchella Aerial Parts. Pharmacogn Mag. 2017 Jul;13(Suppl 2):S244-S249. doi: 10.4103/pm.pm_344_16. Epub 2017 Jul 11. PubMed PMID: 28808387; PubMed Central PMCID: PMC5538161.

12: Picariello G, Sciammaro L, Siano F, Volpe MG, Puppo MC, Mamone G. Comparative analysis of C-glycosidic flavonoids from Prosopis spp. and Ceratonia siliqua seed germ flour. Food Res Int. 2017 Sep;99(Pt 1):730-738. doi: 10.1016/j.foodres.2017.06.058. Epub 2017 Jun 27. PubMed PMID: 28784538.

13: Oshima N, Maruyama T, Yamashita T, Uchiyama N, Amakura Y, Hyuga S, Hyuga M, Nakamori S, Takemoto H, Kobayashi Y, Hakamatsuka T, Odaguchi H, Hanawa T, Goda Y. Two flavone C-glycosides as quality control markers for the manufacturing process of ephedrine alkaloids-free Ephedra Herb extract (EFE) as a crude drug preparation. J Nat Med. 2018 Jan;72(1):73-79. doi: 10.1007/s11418-017-1111-8. Epub 2017 Aug 3. PubMed PMID: 28776291.

14: Sommella E, Pagano F, Pepe G, Ostacolo C, Manfra M, Chieppa M, Di Sanzo R, Carabetta S, Campiglia P, Russo M. Flavonoid Composition of Tarocco (Citrus sinensis L. Osbeck) Clone "Lempso" and Fast Antioxidant Activity Screening by DPPH-UHPLC-PDA-IT-TOF. Phytochem Anal. 2017 Nov;28(6):521-528. doi: 10.1002/pca.2701. Epub 2017 Jul 7. PubMed PMID: 28686312.

15: Dib I, Tits M, Angenot L, Wauters JN, Assaidi A, Mekhfi H, Aziz M, Bnouham M, Legssyer A, Frederich M, Ziyyat A. Antihypertensive and vasorelaxant effects of aqueous extract of Artemisia campestris L. from Eastern Morocco. J Ethnopharmacol. 2017 Jul 12;206:224-235. doi: 10.1016/j.jep.2017.05.036. Epub 2017 May 31. PubMed PMID: 28578165.

16: Ito T, Fujimoto S, Suito F, Shimosaka M, Taguchi G. C-Glycosyltransferases catalyzing the formation of di-C-glucosyl flavonoids in citrus plants. Plant J. 2017 Jul;91(2):187-198. doi: 10.1111/tpj.13555. Epub 2017 Jun 5. PubMed PMID: 28370711.

17: Singhal SS, Jain D, Singhal P, Awasthi S, Singhal J, Horne D. Targeting the mercapturic acid pathway and vicenin-2 for prevention of prostate cancer. Biochim Biophys Acta. 2017 Aug;1868(1):167-175. doi: 10.1016/j.bbcan.2017.03.009. Epub 2017 Mar 28. Review. PubMed PMID: 28359741; PubMed Central PMCID: PMC5638116.

18: Papalia T, Barreca D, Panuccio MR. Assessment of Antioxidant and Cytoprotective Potential of Jatropha (Jatropha curcas) Grown in Southern Italy. Int J Mol Sci. 2017 Mar 18;18(3). pii: E660. doi: 10.3390/ijms18030660. PubMed PMID: 28335473; PubMed Central PMCID: PMC5372672.

19: Chemam Y, Benayache S, Marchioni E, Zhao M, Mosset P, Benayache F. On-Line Screening, Isolation and Identification of Antioxidant Compounds of Helianthemum ruficomum. Molecules. 2017 Feb 8;22(2). pii: E239. doi: 10.3390/molecules22020239. PubMed PMID: 28208718.

20: Rauf A, Raza M, Saleem M, Ozgen U, Karaoglan ES, Renda G, Palaska E, Orhan IE. Carbonic Anhydrase and Urease Inhibitory Potential of Various Plant Phenolics Using in vitro and in silico Methods. Chem Biodivers. 2017 Jun;14(6). doi: 10.1002/cbdv.201700024. Epub 2017 Jun 9. PubMed PMID: 28207990.