Lupulone

Lupulone is a beta-acid that has been found in the hop plant, H. lupulus, and has diverse biological activities, including antibacterial, antioxidant, and anticarcinogenic properties. Lupulone is active against B. subtilis and S. aureus (MICs = 1 and 1.2 µg/ml, respectively), as well as T. b. brucei and L. m. mexicana (IC50s = 0.9 and 4.7 µg/ml, respectively). It scavenges 2,2-diphenyl-1-picrylhydrazyl (DPPH, Cay-14805) radicals in a cell-free assay and inhibits lipid peroxidation in rat brain homogenates (IC50s = 25 and 39 µM, respectively). It reduces proliferation, migration, and capillary tube formation in human umbilical vein endothelial cells (HUVECs) when used at concentrations ranging from 2.5 to 50 µg/ml. Lupulone (40 µg/ml) activates the extrinsic apoptotic death pathway in SW480 and SW620 colon cancer cells.Formal Name: 3,5-dihydroxy-2,6,6-tris(3-methyl-2-buten-1-yl)-4-(3-methyl-1-oxobutyl)-2,4-cyclohexadien-1-one. CAS Number: 468-28-0. Molecular Formula: C26H38O4. Formula Weight: 414.6. Purity: >95%. Formulation: (Request formulation change), A solid. Solubility: Methanol: slightly soluble. SMILES: O=C1C(C/C=C(C)/C)(C/C=C(C)/C)C(O)=C(C(CC(C)C)=O)C(O)=C1C/C=C(C)/C. InChi Code: InChI=1S/C26H38O4/c1-16(2)9-10-20-23(28)22(21(27)15-19(7)8)25(30)26(24(20)29,13-11-17(3)4)14-12-18(5)6/h9,11-12,19,28,30H,10,13-15H2,1-8H3. InChi Key: WPVSVIXDXMNGGN-UHFFFAOYSA-N. Origin: Synthetic.