| Identification | Back Directory | [Name]
5,6-Dihydro-2,3-(methylenedioxy)-9,10-dimethoxy-13-methyldibenzo[a,g]quinolizinium | [CAS]
54260-72-9 | [Synonyms]
13-Methylberberine
13-Methylberberinium Chlorid
13-Methylberberine (chloride)
13-methylberberine/13-Methylberberine chloride
2,3-(Methylenedioxy)-9,10-dimethoxy-13-methyl-5H,6H-dibenzo[a,g]quinolizin-7-ium
9,10-Dimethoxy-13-methyl-5,6-dihydrobenzo[g]-1,3-benzodioxolo[5,6-a]quinolizinium
5,6-Dihydro-2,3-(methylenedioxy)-9,10-dimethoxy-13-methyldibenzo[a,g]quinolizinium | [Molecular Formula]
C21H20ClNO4 | [MDL Number]
MFCD32197205 | [MOL File]
54260-72-9.mol | [Molecular Weight]
385.841 |
| Chemical Properties | Back Directory | [Melting point ]
198-200 °C | [storage temp. ]
Store at -20°C | [solubility ]
Water: 1 mg/ml | [form ]
A crystalline solid | [color ]
Light yellow to yellow |
| Hazard Information | Back Directory | [Description]
13-Methylberberine (13-MB) (chloride) is a 13-methyl-substituted derivative of berberine . Berberine is a widely distributed berberidaceaen alkaloid found in plant tissues that has antibacterial, anti-inflammatory, antitumor, anti-obesity, and hypercholesterolemic activity. 13-MB has improved antibacterial activity against S. aureus (MIC = 125 μg/ml) and improved antitumor activity with a mean GI50 value of 11.7 μM, as compared to berberine. 13-MB also induces down-regulation of adipocyte differentiation transcription factors, reduces de novo lipid synthesis, and accumulates in murine 3T3-L1 adipocytes at higher levels than berberine, suggesting improved anti-obesity activity. | [Uses]
13-Methylberberinium Chloride can be used to treat and prevent immunoinflammatory dermal disorders. It can also be used in synthesis to result in derivatives that can be used to treat nerve diseases and anti-infective agents. | [References]
[1] YIT-LAI CHOW F S Mami Sogame. 13-Methylberberine, a berberine analogue with stronger anti-adipogenic effects on mouse 3T3-L1 cells[J]. Scientific Reports, 2016, 6 1. DOI: 10.1038/srep38129
[2] WEIJIA KONG. Berberine is a novel cholesterol-lowering drug working through a unique mechanism distinct from statins[J]. Nature Medicine, 2004, 10 12: 1344-1351. DOI: 10.1038/nm1135
[3] K IWASA . Antibacterial activity and structure-activity relationships of berberine analogs[J]. European Journal of Medicinal Chemistry, 1996, 31 6: Pages 469-478. DOI: 10.1016/0223-5234(96)85167-1
[4] KINUKO IWASA. In Vitro Cytotoxicity of the Protoberberine-Type Alkaloids[J]. Journal of Natural Products , 2001, 64 7: 896-898. DOI: 10.1021/np000554f
[5] DONG-UNG LEE . Effects of 13-alkyl-substituted berberine alkaloids on the expression of COX-II, TNF-α, iNOS, and IL-12 production in LPS-stimulated macrophages[J]. Life sciences, 2003, 73 11: Pages 1401-1412. DOI: 10.1016/s0024-3205(03)00435-1 |
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