| Identification | Back Directory | [Name]
Malabaricone C | [CAS]
63335-25-1 | [Synonyms]
Malabaricone C
1-(2,6-dihydroxyphenyl)-9-(3,4-dihydroxyphenyl)nonan-1-one
1-(2,6-Dihydroxyphenyl)-9-(3,4-dihydroxyphenyl)-1-nonanone
1-Nonanone, 1-(2,6-dihydroxyphenyl)-9-(3,4-dihydroxyphenyl)- | [Molecular Formula]
C21H26O5 | [MDL Number]
MFCD31557586 | [MOL File]
63335-25-1.mol | [Molecular Weight]
358.43 |
| Chemical Properties | Back Directory | [storage temp. ]
Store at -20°C | [solubility ]
DMF: 25 mg/ml; DMSO: 20 mg/ml; Ethanol: 10 mg/ml | [form ]
A crystalline solid | [color ]
White to off-white | [InChI]
InChI=1S/C21H26O5/c22-16-13-12-15(14-20(16)26)8-5-3-1-2-4-6-9-17(23)21-18(24)10-7-11-19(21)25/h7,10-14,22,24-26H,1-6,8-9H2 | [InChIKey]
HCOZRFYGIFMIEX-UHFFFAOYSA-N | [SMILES]
C(C1=C(O)C=CC=C1O)(=O)CCCCCCCCC1=CC=C(O)C(O)=C1 |
| Hazard Information | Back Directory | [Description]
Malabaricone C is a diarylnonanoid that has been found in Myristica and has diverse biological activities.1,2,3,4 It scavenges 59.9% of 2,2-diphenyl-1-picrylhydrazyl (DPPH; Item No. 14805) radicals when used at a concentration of 7 μg/ml.1 Malabaricone C is active against S. aureus, B. subtilis, and C. albicans in vitro (MICs = 2-32 μg/ml).2 It is cytotoxic to A549, HL-60, and MCF-7 cells (IC50s = 12.3, 46.1, and 10.8 μM, respectively).3 Malabaricone C inhibits sphingomyelin synthase 1 (SMS1) and SMS2 activity in cell lysates (IC50s = 3 and 1.5 μM, respectively).4 It decreases body weight gain, hepatic steatosis, and hepatic and plasma triglyceride levels in a mouse model of high-fat diet-induced obesity when administered at a dose of 0.1% in the diet. | [Uses]
Malabaricone C is a useful research chemical compound from Myristica malabarica which exhibits antioxidant activity. | [Definition]
ChEBI: A natural product found in Myristica cinnamomea. | [in vivo]
Malabaricone C (High-fat diet supplemented with 0.1%, p.o., daily for 8 weeks) reduces body weight gain, improves glucose tolerance, and decreases lipid accumulation in the liver in high fat diet-induced obesity mice models[1].
Malabaricone C (10 mg/kg, i.p., a single dose for 24 h) inhibits T-cell activation and cytokine secretion in mice[2].
| Animal Model: | High fat diet-induced obesity mice models[1] | | Dosage: | High-fat diet supplemented with 0.1% | | Administration: | p.o., daily for 8 weeks | | Result: | Reduced weight gain, improved glucose tolerance, and reduced hepatic steatosis in high fat diet-induced obesity mice models. |
| Animal Model: | Swiss, BALB/c, and C57BL/6 male mice[2] | | Dosage: | 10 mg/kg | | Administration: | i.p., a single dose for 24 h | | Result: | Significantly decreased the percentage of proliferating cells as compared with vehicle control and resulted in significant decrease in mitogen-induced cytokine (IL-2, IFN-γ, and IL-6) secretion by T-cells. |
| [storage]
Store at -20°C | [References]
[1] BIRIJA S. PATRO. Antioxidant Activity of Myristica malabarica Extracts and Their Constituents[J]. Journal of Agricultural and Food Chemistry, 2005, 53 17: 6912-6918. DOI: 10.1021/jf050861x
[2] KHALED Y. ORABI Farouk S E F Jaber S Mossa. Isolation and Characterization of Two Antimicrobial Agents from Mace (Myristica fragrans)[J]. Journal of Natural Products , 1991, 54 3: 856-859. DOI: 10.1021/np50075a017
[3] PARINUCH CHUMKAEW Theera S. New neolignans from the seeds of Myristica fragrans and their cytotoxic activities[J]. Journal of Natural Medicines, 2018, 73 1: 273-277. DOI: 10.1007/s11418-018-1246-2
[4] MUHAMADAQMAL OTHMAN. Malabaricone C as Natural Sphingomyelin Synthase Inhibitor against Diet-Induced Obesity and Its Lipid Metabolism in Mice[J]. ACS Medicinal Chemistry Letters, 2019, 10 8: 1154-1158. DOI: 10.1021/acsmedchemlett.9b00171 |
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