Kuwanon C | CAS#62949-79-5 | Diverse prenylated flavone

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

MedKoo CAT#: 464057

CAS#: 62949-79-5

Description: Kuwanon C is a prenylated flavone originally isolated from M. alba that has diverse biological activities, including antioxidant, antibacterial, antiproliferative, and neuroprotective properties. It scavenges DPPH radicals in a cell-free assay. It is active against E. coli, S. typhimurium, S. epidermis, and S. aureus and inhibits the growth of P388 mouse lymphoma cancer cells. Kuwanon C improves motor coordination in a rotarod test and decreases neuronal loss in the substantia nigra pars compacta in a mouse model of MPTP-induced Parkinson's disease.

Chemical Structure

Kuwanon C

CAS# 62949-79-5

Product data Instruction

Theoretical Analysis

MedKoo Cat#: 464057
Name: Kuwanon C
CAS#: 62949-79-5
Chemical Formula: C25H26O6
Exact Mass: 422.17
Molecular Weight: 422.477
Elemental Analysis: C, 71.07; H, 6.20; O, 22.72

Price and Availability

Size	Price	Availability
5mg	USD 430	2 Weeks
25mg	USD 1190	2 Weeks
Bulk inquiry Welcome, Customer: Please do not inquire quote if your intended use is for a patient since our products are for research use and for chemical synthesis use, not for human use . For in-stock products, we listed price in the web page. You may inquire prices for which sizes were not listed. If no price is listed, this means the product is not in stock at the moment, which may be available via custom synthesis. For cost-effective reason, minimum order of 1g is requested (typically very expensive). The lead time is usually 2-4 months. Quote of less than 1g will not be provided. MedKoo may not offer quote for below reasons: (1) current available synthetic method appears to be extremely expensive which is obviously not affordable to most customers; (2) Key raw material to make the product is temporally not available; (3) DEA controlled substances; (4) the product is under patent protection in customer’s country.

Synonym: Kuwanon C; Kuwanon-C; Mulberrin;

IUPAC/Chemical Name: 2-(2,4-dihydroxyphenyl)-5,7-dihydroxy-3,8-bis(3-methylbut-2-en-1-yl)-4H-chromen-4-one

InChi Key: UWQYBLOHTQWSQD-UHFFFAOYSA-N

InChi Code: InChI=1S/C25H26O6/c1-13(2)5-8-17-20(28)12-21(29)22-23(30)18(9-6-14(3)4)24(31-25(17)22)16-10-7-15(26)11-19(16)27/h5-7,10-12,26-29H,8-9H2,1-4H3

SMILES Code: O=C1C2=C(O)C=C(O)C(C/C=C(C)\C)=C2OC(C3=C(C=C(C=C3)O)O)=C1C/C=C(C)\C

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

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Product Data:

Product Data

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Biological target:	Mulberrin (kuwanon C) is a strong inhibitor of organic anion-transporting polypeptide 2B1 (OATP2B1)-mediated estrone-3-sulfate (E3S) uptake with an IC50 value being 1.8 ±1.5 μM.
In vitro activity:	This study established a mechanism of action by observing how KC (kuwanon C) prevents the infection of SARS-CoV-2 spike pseudotyped virus in ACE2/TPRSS2-overexpressing HEK293T cells. Finally, this study demonstrated that KC inhibits clinical isolates of SARS-CoV-2 in Vero cells. Reference: Int J Mol Sci. 2022 Oct 19;23(20):12516. https://pubmed.ncbi.nlm.nih.gov/36293371/
In vivo activity:	Mul (mulberrin)-treated mice had an attenuated cardiac injured response and improved cardiac function after DOX (doxorubicin) injection. DOX-induced oxidative damage, inflammation accumulation, and myocardial apoptosis were largely attenuated by the treatment of Mul. Reference: Oxid Med Cell Longev. 2022 Jul 7;2022:2967142. https://pubmed.ncbi.nlm.nih.gov/35847586/

Solubility Data

	Solvent	Max Conc. mg/mL	Max Conc. mM
Solubility
	DMSO	100.0	236.70

Preparing Stock Solutions

The following data is based on the product molecular weight 422.48 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

Formulation protocol:	1. Kim YS, Kwon EB, Kim B, Chung HS, Choi G, Kim YH, Choi JG. Mulberry Component Kuwanon C Exerts Potent Therapeutic Efficacy In Vitro against COVID-19 by Blocking the SARS-CoV-2 Spike S1 RBD:ACE2 Receptor Interaction. Int J Mol Sci. 2022 Oct 19;23(20):12516. doi: 10.3390/ijms232012516. PMID: 36293371; PMCID: PMC9604257. 2. Wen F, Shi M, Bian J, Zhang H, Gui C. Identification of natural products as modulators of OATP2B1 using LC-MS/MS to quantify OATP-mediated uptake. Pharm Biol. 2016;54(2):293-302. doi: 10.3109/13880209.2015.1034326. Epub 2015 Apr 10. PMID: 25858254. 3. Ye P, Li WL, Bao LT, Ke W. Mulberrin Confers Protection against Doxorubicin-Induced Cardiotoxicity via Regulating AKT Signaling Pathways in Mice. Oxid Med Cell Longev. 2022 Jul 7;2022:2967142. doi: 10.1155/2022/2967142. PMID: 35847586; PMCID: PMC9283020. 4. Cao W, Dong Y, Zhao W, Lu X, Sun L. Mulberrin attenuates 1-methyl-4-phenyl-1,2,3,6- tetrahydropyridine (MPTP)-induced Parkinson's disease by promoting Wnt/β-catenin signaling pathway. J Chem Neuroanat. 2019 Jul;98:63-70. doi: 10.1016/j.jchemneu.2019.04.003. Epub 2019 Apr 9. PMID: 30978489.
In vitro protocol:	1. Kim YS, Kwon EB, Kim B, Chung HS, Choi G, Kim YH, Choi JG. Mulberry Component Kuwanon C Exerts Potent Therapeutic Efficacy In Vitro against COVID-19 by Blocking the SARS-CoV-2 Spike S1 RBD:ACE2 Receptor Interaction. Int J Mol Sci. 2022 Oct 19;23(20):12516. doi: 10.3390/ijms232012516. PMID: 36293371; PMCID: PMC9604257. 2. Wen F, Shi M, Bian J, Zhang H, Gui C. Identification of natural products as modulators of OATP2B1 using LC-MS/MS to quantify OATP-mediated uptake. Pharm Biol. 2016;54(2):293-302. doi: 10.3109/13880209.2015.1034326. Epub 2015 Apr 10. PMID: 25858254.
In vivo protocol:	1. Ye P, Li WL, Bao LT, Ke W. Mulberrin Confers Protection against Doxorubicin-Induced Cardiotoxicity via Regulating AKT Signaling Pathways in Mice. Oxid Med Cell Longev. 2022 Jul 7;2022:2967142. doi: 10.1155/2022/2967142. PMID: 35847586; PMCID: PMC9283020. 2. Cao W, Dong Y, Zhao W, Lu X, Sun L. Mulberrin attenuates 1-methyl-4-phenyl-1,2,3,6- tetrahydropyridine (MPTP)-induced Parkinson's disease by promoting Wnt/β-catenin signaling pathway. J Chem Neuroanat. 2019 Jul;98:63-70. doi: 10.1016/j.jchemneu.2019.04.003. Epub 2019 Apr 9. PMID: 30978489.

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1: Chajra H, Salwinski A, Guillaumin A, Mignard B, Hannewald P, Duriot L, Warnault P, Guillet-Claude C, Fréchet M, Bourgaud F. Plant Milking Technology-An Innovative and Sustainable Process to Produce Highly Active Extracts from Plant Roots. Molecules. 2020 Sep 11;25(18):4162. doi: 10.3390/molecules25184162. PMID: 32932881; PMCID: PMC7570732.

2: Ko W, Yoon CS, Kim KW, Lee H, Kim N, Woo ER, Kim YC, Kang DG, Lee HS, Oh H, Lee DS. Neuroprotective and Anti-Inflammatory Effects of Kuwanon C from Cudrania tricuspidata Are Mediated by Heme Oxygenase-1 in HT22 Hippocampal Cells, RAW264.7 Macrophage, and BV2 Microglia. Int J Mol Sci. 2020 Jul 8;21(14):4839. doi: 10.3390/ijms21144839. PMID: 32650596; PMCID: PMC7402286.

3: Wu SC, Han F, Song MR, Chen S, Li Q, Zhang Q, Zhu K, Shen JZ. Natural Flavones from Morus alba against Methicillin-Resistant Staphylococcus aureus via Targeting the Proton Motive Force and Membrane Permeability. J Agric Food Chem. 2019 Sep 11;67(36):10222-10234. doi: 10.1021/acs.jafc.9b01795. Epub 2019 Sep 3. PMID: 31385700.

4: Azminah A, Erlina L, Radji M, Mun'im A, Syahdi RR, Yanuar A. In silico and in vitro identification of candidate SIRT1 activators from Indonesian medicinal plants compounds database. Comput Biol Chem. 2019 Dec;83:107096. doi: 10.1016/j.compbiolchem.2019.107096. Epub 2019 Jul 18. PMID: 31377446.

5: Cao W, Dong Y, Zhao W, Lu X, Sun L. Mulberrin attenuates 1-methyl-4-phenyl-1,2,3,6- tetrahydropyridine (MPTP)-induced Parkinson's disease by promoting Wnt/β-catenin signaling pathway. J Chem Neuroanat. 2019 Jul;98:63-70. doi: 10.1016/j.jchemneu.2019.04.003. Epub 2019 Apr 9. PMID: 30978489.

6: Abdel Bar FM, Abbas GM, Gohar AA, Lahloub MI. Antiproliferative activity of stilbene derivatives and other constituents from the stem bark of Morus nigra L. Nat Prod Res. 2020 Dec;34(24):3506-3513. doi: 10.1080/14786419.2019.1573236. Epub 2019 Mar 1. PMID: 30822142.

7: Xia P, Gao X, Duan L, Zhang W, Sun YF. Mulberrin (Mul) reduces spinal cord injury (SCI)-induced apoptosis, inflammation and oxidative stress in rats via miroRNA-337 by targeting Nrf-2. Biomed Pharmacother. 2018 Nov;107:1480-1487. doi: 10.1016/j.biopha.2018.07.082. Epub 2018 Sep 4. PMID: 30257365.

8: Hou XD, Ge GB, Weng ZM, Dai ZR, Leng YH, Ding LL, Jin LL, Yu Y, Cao YF, Hou J. Natural constituents from Cortex Mori Radicis as new pancreatic lipase inhibitors. Bioorg Chem. 2018 Oct;80:577-584. doi: 10.1016/j.bioorg.2018.07.011. Epub 2018 Jul 17. PMID: 30032067.

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14: Wen F, Shi M, Bian J, Zhang H, Gui C. Identification of natural products as modulators of OATP2B1 using LC-MS/MS to quantify OATP-mediated uptake. Pharm Biol. 2016;54(2):293-302. doi: 10.3109/13880209.2015.1034326. Epub 2015 Apr 10. PMID: 25858254.

15: Zelová H, Hanáková Z, Čermáková Z, Šmejkal K, Dalĺ Acqua S, Babula P, Cvačka J, Hošek J. Evaluation of anti-inflammatory activity of prenylated substances isolated from Morus alba and Morus nigra. J Nat Prod. 2014 Jun 27;77(6):1297-303. doi: 10.1021/np401025f. Epub 2014 Jun 5. PMID: 24901948.

16: Abbas GM, Abdel Bar FM, Baraka HN, Gohar AA, Lahloub MF. A new antioxidant stilbene and other constituents from the stem bark of Morus nigra L. Nat Prod Res. 2014;28(13):952-9. doi: 10.1080/14786419.2014.900770. Epub 2014 Mar 28. PMID: 24673367.

17: Syahdi RR, Mun'im A, Suhartanto H, Yanuar A. Virtual screening of Indonesian herbal database as HIV-1 reverse transcriptase inhibitor. Bioinformation. 2012;8(24):1206-10. doi: 10.6026/97320630081206. Epub 2012 Dec 8. PMID: 23275721; PMCID: PMC3530873.

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19: Yang ZG, Matsuzaki K, Takamatsu S, Kitanaka S. Inhibitory effects of constituents from Morus alba var. multicaulis on differentiation of 3T3-L1 cells and nitric oxide production in RAW264.7 cells. Molecules. 2011 Jul 19;16(7):6010-22. doi: 10.3390/molecules16076010. PMID: 21772233; PMCID: PMC6264761.

20: Kim JY, Lee WS, Kim YS, Curtis-Long MJ, Lee BW, Ryu YB, Park KH. Isolation of cholinesterase-inhibiting flavonoids from Morus lhou. J Agric Food Chem. 2011 May 11;59(9):4589-96. doi: 10.1021/jf200423g. Epub 2011 Apr 5. PMID: 21434689.

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Kuwanon C featured