Afzelin | CAS#482-39-3 | flavonol glycoside

MedKoo Cat#: 591337 | Name: Afzelin

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Description:

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

Afzelin is a flavonol glycoside. It is the rhamnoside of kaempferol. Afzelin improved the survival rate and reduced the serum levels of alanine aminotransferase and pro-inflammatory cytokines in GalN/LPS-treated mice. Afzelin attenuated the mitochondrial damage, as indicated by diminished mitochondrial swelling and mitochondrial glutamate dehydrogenase activity in GalN/LPS-treated mice. Afzelin enhanced mitochondrial biogenesis, as indicated by increased levels of PPAR-γ coactivator 1α, nuclear respiratory factor 1 and mitochondrial transcription factor A. Afzelin also decreased the level of mitophagy-related proteins, parkin and PTEN-induced putative kinase 1. Furthermore, while GalN/LPS significantly increased the level of fission-related protein, dynamin-related protein 1, and decreased the level of fusion-related protein, mitofusin 2; these effects were attenuated by afzelin.

Chemical Structure

Afzelin

CAS#482-39-3

Theoretical Analysis

MedKoo Cat#: 591337

Name: Afzelin

CAS#: 482-39-3

Chemical Formula: C21H20O10

Exact Mass: 432.1056

Molecular Weight: 432.38

Elemental Analysis: C, 58.34; H, 4.66; O, 37.00

Price and Availability

Size	Price	Availability
5mg	USD 350.00	2 Weeks
10mg	USD 600.00	2 Weeks
25mg	USD 1,250.00	2 Weeks

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Related CAS #

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Synonym

Afzelin; Kaempferol 3-rhamnoside; Kaempferin; kaempferol-3-rhamnoside; Afzeloside; Kaempferol 3-O-α-L-rhamnopyranoside

IUPAC/Chemical Name

4H-1-Benzopyran-4-one, 3-((6-deoxy-alpha-L-mannopyranosyl)oxy)-5,7-dihydroxy-2-(4-hydroxyphenyl)-

InChi Key

SOSLMHZOJATCCP-AEIZVZFYSA-N

InChi Code

InChI=1S/C21H20O10/c1-8-15(25)17(27)18(28)21(29-8)31-20-16(26)14-12(24)6-11(23)7-13(14)30-19(20)9-2-4-10(22)5-3-9/h2-8,15,17-18,21-25,27-28H,1H3/t8-,15-,17+,18+,21-/m0/s1

SMILES Code

O=C1C(O[C@H]2[C@@H]([C@@H]([C@H]([C@H](C)O2)O)O)O)=C(C3=CC=C(O)C=C3)OC4=CC(O)=CC(O)=C14

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).

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 432.38 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: Lotha R, Sundaramoorthy NS, Shamprasad BR, Nagarajan S, Sivasubramanian A. Plant nutraceuticals (Quercetrin and Afzelin) capped silver nanoparticles exert potent antibiofilm effect against food borne pathogen Salmonella enterica serovar Typhi and curtail planktonic growth in zebrafish infection model. Microb Pathog. 2018 Apr 30;120:109-118. doi: 10.1016/j.micpath.2018.04.044. [Epub ahead of print] PubMed PMID: 29715535. 2: Shingnaisui K, Dey T, Manna P, Kalita J. Therapeutic potentials of Houttuynia cordata Thunb. against inflammation and oxidative stress: A review. J Ethnopharmacol. 2018 Jun 28;220:35-43. doi: 10.1016/j.jep.2018.03.038. Epub 2018 Mar 30. Review. PubMed PMID: 29605674. 3: Zhao Y, Chen S, Wang Y, Lv C, Wang J, Lu J. Effect of drying processes on prenylflavonoid content and antioxidant activity of Epimedium koreanum Nakai. J Food Drug Anal. 2018 Apr;26(2):796-806. doi: 10.1016/j.jfda.2017.05.011. Epub 2017 Jun 13. PubMed PMID: 29567251. 4: Oliveira MM, Daré RG, Barizão ÉO, Visentainer JV, Romagnolo MB, Nakamura CV, Truiti MDCT. Photodamage attenuating potential of Nectandra hihua against UVB-induced oxidative stress in L929 fibroblasts. J Photochem Photobiol B. 2018 Apr;181:127-133. doi: 10.1016/j.jphotobiol.2018.03.008. Epub 2018 Mar 9. PubMed PMID: 29550671. 5: Shi M, He N, Li W, Li C, Kang W. Simultaneous determination of myricetrin, quercitrin and afzelin in leaves of Cercis chinensis by a fast and effective method of ionic liquid microextraction coupled with HPLC. Chem Cent J. 2018 Mar 1;12(1):23. doi: 10.1186/s13065-018-0391-8. PubMed PMID: 29497935; PubMed Central PMCID: PMC5832659. 6: Trinh PTN, An NH, An PN, Tri MD, Du CV, Minh PN, Thuy NTL, Tuan NT, Thoa VTK, Tuan NN, Dung LT. A new benzofuran derivative from the leaves of Ficus pumila L. Nat Prod Res. 2017 Oct 26:1-5. doi: 10.1080/14786419.2017.1395427. [Epub ahead of print] PubMed PMID: 29072969. 7: Shan M, Li SFY, Yu S, Qian Y, Guo S, Zhang L, Ding A. Chemical Fingerprint and Quantitative Analysis for the Quality Evaluation of Platycladi cacumen by Ultra-performance Liquid Chromatography Coupled with Hierarchical Cluster Analysis. J Chromatogr Sci. 2018 Jan 1;56(1):41-48. doi: 10.1093/chromsci/bmx079. PubMed PMID: 28977346. 8: Huang CY, Lin YT, Kuo HC, Chiou WF, Lee MH. Compounds isolated from Eriobotrya deflexa leaves protect against ultraviolet radiation B-induced photoaging in human fibroblasts. J Photochem Photobiol B. 2017 Oct;175:244-253. doi: 10.1016/j.jphotobiol.2017.08.042. Epub 2017 Sep 4. PubMed PMID: 28917186. 9: Ramos AC, de Oliveira RR. A new alkaloid and flavonoids isolated from Solanum cernuum leaves by high-performance countercurrent chromatography. Nat Prod Res. 2017 Oct;31(20):2405-2412. doi: 10.1080/14786419.2017.1311889. Epub 2017 Apr 7. PubMed PMID: 28385048. 10: Benmerache A, Benteldjoune M, Alabdul Magid A, Abedini A, Berrehal D, Kabouche A, Gangloff SC, Voutquenne-Nazabadioko L, Kabouche Z. Chemical composition, antioxidant and antibacterial activities of Tamarix balansae J. Gay aerial parts. Nat Prod Res. 2017 Dec;31(24):2828-2835. doi: 10.1080/14786419.2017.1299729. Epub 2017 Mar 10. PubMed PMID: 28281364. 11: Trinh PTN, Luan NQ, Tri MD, Khanh VD, An NH, Minh PN, An PN, Thuy NTL, Phung NKP, Dung LT. New naphthalene derivative from the leaves of Cassia grandis L. Nat Prod Res. 2017 Aug;31(15):1733-1738. doi: 10.1080/14786419.2017.1290615. Epub 2017 Feb 16. PubMed PMID: 28278658. 12: Kim SB, Hwang SH, Suh HW, Lim SS. Phytochemical Analysis of Agrimonia pilosa Ledeb, Its Antioxidant Activity and Aldose Reductase Inhibitory Potential. Int J Mol Sci. 2017 Feb 10;18(2). pii: E379. doi: 10.3390/ijms18020379. PubMed PMID: 28208627; PubMed Central PMCID: PMC5343914. 13: Yu KY, Wu W, Li SZ, Dou LL, Liu LL, Li P, Liu EH. A new compound, methylbergenin along with eight known compounds with cytotoxicity and anti-inflammatory activity from Ardisia japonica. Nat Prod Res. 2017 Nov;31(22):2581-2586. doi: 10.1080/14786419.2017.1283495. Epub 2017 Jan 30. PubMed PMID: 28135873. 14: Voukeng IK, Nganou BK, Sandjo LP, Celik I, Beng VP, Tane P, Kuete V. Antibacterial activities of the methanol extract, fractions and compounds from Elaeophorbia drupifera (Thonn.) Stapf. (Euphorbiaceae). BMC Complement Altern Med. 2017 Jan 7;17(1):28. doi: 10.1186/s12906-016-1509-y. PubMed PMID: 28061888; PubMed Central PMCID: PMC5219710. 15: Jung E, Kim JH, Kim MO, Lee SY, Lee J. Melanocyte-protective effect of afzelin is mediated by the Nrf2-ARE signalling pathway via GSK-3β inactivation. Exp Dermatol. 2017 Sep;26(9):764-770. doi: 10.1111/exd.13277. Epub 2017 Apr 11. PubMed PMID: 27992083. 16: Lee SB, Kang JW, Kim SJ, Ahn J, Kim J, Lee SM. Afzelin ameliorates D-galactosamine and lipopolysaccharide-induced fulminant hepatic failure by modulating mitochondrial quality control and dynamics. Br J Pharmacol. 2017 Jan;174(2):195-209. doi: 10.1111/bph.13669. Epub 2016 Dec 15. PubMed PMID: 27861739; PubMed Central PMCID: PMC5192940. 17: Torres-Naranjo M, Suárez A, Gilardoni G, Cartuche L, Flores P, Morocho V. Chemical Constituents of Muehlenbeckia tamnifolia (Kunth) Meisn (Polygonaceae) and Its In Vitro α-Amilase and α-Glucosidase Inhibitory Activities. Molecules. 2016 Nov 2;21(11). pii: E1461. PubMed PMID: 27827864. 18: Fouseki MM, Damianakos H, Karikas GA, Roussakis C, P Gupta M, Chinou I. Chemical constituents from Cordia alliodora and C. colloccoca (Boraginaceae) and their biological activities. Fitoterapia. 2016 Dec;115:9-14. doi: 10.1016/j.fitote.2016.09.004. Epub 2016 Sep 20. PubMed PMID: 27659390. 19: Sulaiman I, Lim JC, Soo HL, Stanslas J. Molecularly targeted therapies for asthma: Current development, challenges and potential clinical translation. Pulm Pharmacol Ther. 2016 Oct;40:52-68. doi: 10.1016/j.pupt.2016.07.005. Epub 2016 Jul 22. Review. PubMed PMID: 27453494. 20: Jung E, Kim JH, Kim MO, Jang S, Kang M, Oh SW, Nho YH, Kang SH, Kim MH, Park SH, Lee J. Afzelin positively regulates melanogenesis through the p38 MAPK pathway. Chem Biol Interact. 2016 Jul 25;254:167-72. doi: 10.1016/j.cbi.2016.06.010. Epub 2016 Jun 7. PubMed PMID: 27287415.

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Diisopropyl fumarate