Ayanin | CAS#572-32-7 | flavonoid

MedKoo Cat#: 145464 | Name: Ayanin

Description:

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

Ayanin is a flavonoid isolated from Callicarpa nudiflora. Ayanin is an inhibitor of MRSA ClpP with an IC50 of 19.63 μM. Ayanin reduces the virulence of Staphylococcus aureus (S. aureus) by down-regulating the level of some important virulence factors, including agrA, RNAⅢ, hla, pvl, psmα and spa. Ayanin exhibits a significant therapeutic effect on pneumonia infection induced by S. aureus in mice. Ayanin is a promising therapeutic agent to combat MRSA infections by targeting ClpP.

Chemical Structure

Ayanin

CAS#572-32-7

Theoretical Analysis

MedKoo Cat#: 145464

Name: Ayanin

CAS#: 572-32-7

Chemical Formula: C18H16O7

Exact Mass: 344.0900

Molecular Weight: 344.32

Elemental Analysis: C, 62.79; H, 4.68; O, 32.53

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.

Bulk Inquiry

Related CAS #

No Data

Synonym

Ayanin; NSC-691652;

IUPAC/Chemical Name

5-hydroxy-2-(3-hydroxy-4-methoxyphenyl)-3,7-dimethoxy-4H-chromen-4-one

InChi Key

KPCRYSMUMBNTCK-UHFFFAOYSA-N

InChi Code

1S/C18H16O7/c1-22-10-7-12(20)15-14(8-10)25-17(18(24-3)16(15)21)9-4-5-13(23-2)11(19)6-9/h4-8,19-20H,1-3H3

SMILES Code

COC1=CC(O)=C2C(=O)C(OC)=C(OC2=C1)C3=CC(O)=C(OC)C=C3

Appearance

To be determined

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

To be determined

Shelf Life

>2 years if stored properly

Drug Formulation

To be determined

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 344.32 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: Jin M, Zhu S, Tang Y, Kong X, Wang X, Li Y, Jiang S, Wei L, Hu C, Wang B, Song W. Ayanin, a natural flavonoid inhibitor of Caseinolytic protease, is a promising therapeutic agent to combat methicillin-resistant Staphylococcus aureus infections. Biochem Pharmacol. 2023 Nov;217:115814. doi: 10.1016/j.bcp.2023.115814. Epub 2023 Sep 26. PMID: 37769713. 2: Lee FP, Shih CM, Shen HY, Chen CM, Chen CM, Ko WC. Ayanin, a non-selective phosphodiesterase 1-4 inhibitor, effectively suppresses ovalbumin-induced airway hyperresponsiveness without affecting xylazine/ketamine-induced anesthesia. Eur J Pharmacol. 2010 Jun 10;635(1-3):198-203. doi: 10.1016/j.ejphar.2010.02.055. Epub 2010 Mar 20. PMID: 20307524. 3: Marrero MT, Estévez S, Negrín G, Quintana J, López M, Pérez FJ, Triana J, León F, Estévez F. Ayanin diacetate-induced cell death is amplified by TRAIL in human leukemia cells. Biochem Biophys Res Commun. 2012 Nov 9;428(1):116-20. doi: 10.1016/j.bbrc.2012.10.017. Epub 2012 Oct 11. PMID: 23063980. 4: Kawai M, Hirano T, Higa S, Arimitsu J, Maruta M, Kuwahara Y, Ohkawara T, Hagihara K, Yamadori T, Shima Y, Ogata A, Kawase I, Tanaka T. Flavonoids and related compounds as anti-allergic substances. Allergol Int. 2007 Jun;56(2):113-23. doi: 10.2332/allergolint.R-06-135. Epub 2007 Mar 1. PMID: 17384531. 5: Morgan JW, Thomson J. Ayan dermatitis. Br J Ind Med. 1967 Apr;24(2):156-8. doi: 10.1136/oem.24.2.156. PMID: 4225728; PMCID: PMC1008547. 6: Guerrero MF, Puebla P, Martín ML, Carrón R, San Román L, Reguero MT, Arteaga L. Inhibitory effect of N(G)-nitro-L-arginine methyl ester on the anti- adrenergic response elicited by ayanin in the pithed rat. Planta Med. 2002 Apr;68(4):322-5. doi: 10.1055/s-2002-26755. PMID: 11988855. 7: Arciniegas A, Pérez-Castorena AL, Meléndez-Aguirre M, Ávila JG, García-Bores AM, Villaseñor JL, Romo de Vivar A. Chemical Composition and Antimicrobial Activity of Ageratina deltoidea. Chem Biodivers. 2018 Mar;15(3):e1700529. doi: 10.1002/cbdv.201700529. PMID: 29427474. 8: The Son N. Genus Miliusa: A Review of Phytochemistry and Pharmacology. Evid Based Complement Alternat Med. 2019 Aug 14;2019:8314693. doi: 10.1155/2019/8314693. PMID: 31485249; PMCID: PMC6710790. 9: Chmiel M, Stompor-Gorący M. The Spectrum of Pharmacological Actions of Syringetin and Its Natural Derivatives-A Summary Review. Nutrients. 2022 Dec 4;14(23):5157. doi: 10.3390/nu14235157. PMID: 36501187; PMCID: PMC9739508. 10: Mahambo ET, Uwamariya C, Miah M, Clementino LDC, Alvarez LCS, Di Santo Meztler GP, Trybala E, Said J, Wieske LHE, Ward JS, Rissanen K, Munissi JJE, Costa FTM, Sunnerhagen P, Bergström T, Nyandoro SS, Erdelyi M. Crotofolane Diterpenoids and Other Constituents Isolated from Croton kilwae. J Nat Prod. 2023 Feb 24;86(2):380-389. doi: 10.1021/acs.jnatprod.2c01007. Epub 2023 Feb 7. PMID: 36749598; PMCID: PMC9972476. 11: Yuan Z, Luan G, Wang Z, Hao X, Li J, Suo Y, Li G, Wang H. Flavonoids from Potentilla parvifolia Fisch. and Their Neuroprotective Effects in Human Neuroblastoma SH-SY5Y Cells in vitro. Chem Biodivers. 2017 Jun;14(6). doi: 10.1002/cbdv.201600487. Epub 2017 Apr 25. PMID: 28294523. 12: Gyeltshen T, Jordan GJ, Smith JA, Bissember AC. Natural products isolation studies of the paleoendemic plant species Nothofagus gunnii and Nothofagus cunninghamii. Fitoterapia. 2022 Jan;156:105088. doi: 10.1016/j.fitote.2021.105088. Epub 2021 Nov 17. PMID: 34798163. 13: Mahmoud AB, Danton O, Kaiser M, Khalid S, Hamburger M, Mäser P. HPLC-Based Activity Profiling for Antiprotozoal Compounds in Croton gratissimus and Cuscuta hyalina. Front Pharmacol. 2020 Aug 14;11:1246. doi: 10.3389/fphar.2020.01246. PMID: 32922290; PMCID: PMC7456963. 14: Guerrero MF, Puebla P, Carrón R, Martín ML, San Román L. Quercetin 3,7-dimethyl ether: a vasorelaxant flavonoid isolated from Croton schiedeanus Schlecht. J Pharm Pharmacol. 2002 Oct;54(10):1373-8. doi: 10.1211/002235702760345455. PMID: 12396299. 15: Chan AL, Huang HL, Chien HC, Chen CM, Lin CN, Ko WC. Inhibitory effects of quercetin derivatives on phosphodiesterase isozymes and high-affinity [(3) H]-rolipram binding in guinea pig tissues. Invest New Drugs. 2008 Oct;26(5):417-24. doi: 10.1007/s10637-008-9114-7. Epub 2008 Feb 9. PMID: 18264679. 16: Chen JJ, Duh CY, Huang HY, Chen IS. Furoquinoline alkaloids and cytotoxic constituents from the leaves of Melicope semecarpifolia. Planta Med. 2003 Jun;69(6):542-6. doi: 10.1055/s-2003-40637. PMID: 12865974. 17: Guerrero MF, Puebla P, Carrón R, Martín ML, San Román L. Vasorelaxant effect of new neo-clerodane diterpenoids isolated from Croton schiedeanus. J Ethnopharmacol. 2004 Sep;94(1):185-9. doi: 10.1016/j.jep.2004.05.018. PMID: 15261981. 18: Lewin G, Maciuk A, Thoret S, Aubert G, Dubois J, Cresteil T. Semisynthesis of natural flavones inhibiting tubulin polymerization, from hesperidin. J Nat Prod. 2010 Apr 23;73(4):702-6. doi: 10.1021/np100065v. PMID: 20356063. 19: Dao TB, Nguyen TM, Nguyen VQ, Tran TM, Tran NM, Nguyen CH, Nguyen TH, Nguyen HH, Sichaem J, Tran CL, Duong TH. Flavones from Combretum quadrangulare Growing in Vietnam and Their Alpha-Glucosidase Inhibitory Activity. Molecules. 2021 Apr 26;26(9):2531. doi: 10.3390/molecules26092531. PMID: 33926133; PMCID: PMC8123651. 20: Hirano T, Higa S, Arimitsu J, Naka T, Ogata A, Shima Y, Fujimoto M, Yamadori T, Ohkawara T, Kuwabara Y, Kawai M, Matsuda H, Yoshikawa M, Maezaki N, Tanaka T, Kawase I, Tanaka T. Luteolin, a flavonoid, inhibits AP-1 activation by basophils. Biochem Biophys Res Commun. 2006 Feb 3;340(1):1-7. doi: 10.1016/j.bbrc.2005.11.157. Epub 2005 Dec 6. PMID: 16343431.