1.0 2010-04-08 22:11:29 UTC 2019-11-26 03:10:48 UTC FDB014814 Carnosol Bitter principle in Salvia carnosa, Salvia officinalis (sage), Salvia triloba (Greek sage) and Rosmarinus officinalis (rosemary). Nutriceutical with anticancer props. Carnosol is a naturally occurring phenolic diterpene found in rosemary (Rosemarinus officinalis, Labiatae). It has been known that an extract of rosemary leaves contains high antioxidative activity. Ninety percent of this antioxidative activity can be attributed to carnosol and carnosic acid. Carnosic acid is easily converted to carnosol by oxidation. Carnosol has multiple beneficial medicinal effects including anti-inflammatory, anti-microbial and anti-cancer activities in various disease models. Carnosol may possess important neuroprotective effects against rotenone-induced DA neuronal damage. Naturally occurring antioxidants reduce the risk of neurodegenerative diseases. In addition, carnosol and carnosic acid promoted the synthesis of nerve growth factor in glial cells. Carnosol-mediated neuroprotection in DA neurons is involved in the attenuation of caspase-3 activity, which was induced by rotenone. Furthermore, carnosol-mediated tyrosine hydroxylase (TH) increase, which is dependent on the Raf-mitogen-activated protein kinase (MEK)-extracellular signal-regulated kinase (ERK)1/2 signaling pathway, is responsible for the neuroprotection in SN4741 DA cells. (PMID: 17047462); Carnosol, a phenolic diterpene compound of the labiate herbs rosemary and sage, is an activator of the human peroxisome proliferator-activated receptor gamma (PPARgamma), a ligand activated transcription factor, belonging to the metazoan family of nuclear hormone receptors. Activation of PPARgamma increases the transcription of enzymes involved in primary metabolism, leading to lower blood levels of fatty acids and glucose. Hence, PPARgamma represents the major target for the glitazone type of drugs currently being used clinically for the treatment of type 2 diabetes. (PMID: 16858665) 1,3,4,9,10,10AS-hexahydro-5,6-dihydroxy-1,1-dimethyl-7-isopropyl-2H-9S,4ar-(epoxymethano)phenanthren-12-one 11,12-Dihydroxy-8,11,13-abietatrien-20,7-olide Picrosalvin C20H26O4 330.418 330.18310932 3,4-dihydroxy-11,11-dimethyl-5-(propan-2-yl)-16-oxatetracyclo[6.6.2.0^{1,10}.0^{2,7}]hexadeca-2(7),3,5-trien-15-one 3,4-dihydroxy-5-isopropyl-11,11-dimethyl-16-oxatetracyclo[6.6.2.0^{1,10}.0^{2,7}]hexadeca-2(7),3,5-trien-15-one 5957-80-2 CC(C)C1=CC2=C(C(O)=C1O)C13CCCC(C)(C)C1CC2OC3=O InChI=1S/C20H26O4/c1-10(2)11-8-12-13-9-14-19(3,4)6-5-7-20(14,18(23)24-13)15(12)17(22)16(11)21/h8,10,13-14,21-22H,5-7,9H2,1-4H3 XUSYGBPHQBWGAD-UHFFFAOYSA-N belongs to the class of organic compounds known as diterpene lactones. These are diterpenoids containing a lactone moiety. Diterpene lactones Organic compounds Lipids and lipid-like molecules Prenol lipids Terpene lactones Aromatic heteropolycyclic compounds 1-hydroxy-4-unsubstituted benzenoids 2-benzopyrans Carbonyl compounds Carboxylic acid esters Delta valerolactones Diterpenoids Hydrocarbon derivatives Monocarboxylic acids and derivatives Organic oxides Oxacyclic compounds Oxanes Phenanthrenes and derivatives Tetralins 1-hydroxy-4-unsubstituted benzenoid 2-benzopyran Aromatic heteropolycyclic compound Benzenoid Benzopyran Carbonyl group Carboxylic acid derivative Carboxylic acid ester Delta valerolactone Delta_valerolactone Diterpene lactone Diterpenoid Hydrocarbon derivative Isochromane Lactone Monocarboxylic acid or derivatives Organic oxide Organic oxygen compound Organoheterocyclic compound Organooxygen compound Oxacycle Oxane Phenanthrene Tetralin Solid logp 4.35 ALOGPS logs -3.92 ALOGPS solubility 3.95e-02 g/l ALOGPS melting_point Mp 221-226° logp 4.58 ChemAxon pka_strongest_acidic 9.19 ChemAxon pka_strongest_basic -6.1 ChemAxon iupac 3,4-dihydroxy-11,11-dimethyl-5-(propan-2-yl)-16-oxatetracyclo[6.6.2.0^{1,10}.0^{2,7}]hexadeca-2(7),3,5-trien-15-one ChemAxon average_mass 330.418 ChemAxon mono_mass 330.18310932 ChemAxon smiles CC(C)C1=CC2=C(C(O)=C1O)C13CCCC(C)(C)C1CC2OC3=O ChemAxon formula C20H26O4 ChemAxon inchi InChI=1S/C20H26O4/c1-10(2)11-8-12-13-9-14-19(3,4)6-5-7-20(14,18(23)24-13)15(12)17(22)16(11)21/h8,10,13-14,21-22H,5-7,9H2,1-4H3 ChemAxon inchikey XUSYGBPHQBWGAD-UHFFFAOYSA-N ChemAxon polar_surface_area 66.76 ChemAxon refractivity 91.43 ChemAxon polarizability 35.86 ChemAxon rotatable_bond_count 1 ChemAxon acceptor_count 3 ChemAxon donor_count 2 ChemAxon physiological_charge 0 ChemAxon formal_charge 0 ChemAxon Specdb::MsMs 89040 Specdb::MsMs 89041 Specdb::MsMs 89042 Specdb::MsMs 151887 Specdb::MsMs 151888 Specdb::MsMs 151889 HMDB02121 #<Reference:0x000055ce3230a8a8> #<Reference:0x000055ce3230a6c8> Black tea Type 1 Caraway Type 1 specific Carum carvi 48032 0.0 0.0 0.0 mg/100 g Ceylon cinnamon Type 1 specific Cinnamomum verum 128608 0.0 0.0 0.0 mg/100 g Cloves Type 1 specific Syzygium aromaticum 219868 0.0 0.0 0.0 mg/100 g Common sage Type 1 specific Salvia officinalis 38868 Cumin Type 1 specific Cuminum cyminum 52462 0.0 0.0 0.0 mg/100 g Ginger Type 1 specific Zingiber officinale 94328 0.0 0.0 0.0 mg/100 g Green tea Type 1 Herbal tea Type 1 Herbs and Spices Unknown generic Nutmeg Type 1 specific Myristica fragrans 51089 0.0 0.0 0.0 mg/100 g Pepper (Spice) Type 1 specific Piper nigrum 13216 0.0 0.0 0.0 mg/100 g Red tea Type 1 Rosemary Type 1 specific Rosmarinus officinalis 39367 284.824998 516.65 52.999996185 mg/100 g Star anise Type 1 specific Illicium verum 124778 0.0 0.0 0.0 mg/100 g Sweet bay Type 1 specific Laurus nobilis 85223 0.0 0.0 0.0 mg/100 g Tea Type 1 specific Camellia sinensis 4442 bitter 5-lipoxygenase inhibitor 10 A compound or agent that combines with an enzyme in such a manner as to prevent the normal substrate-enzyme combination and the catalytic reaction. Anti hepatotoxic 328 Any compound that is able to prevent damage to the liver. Anti HIV 333 A substance that destroys or inhibits replication of viruses. Anti lipoperoxidant 407 Anti radicular 572 Anti-inflammatory 370 A substance that reduces or suppresses inflammation. Anti-mutagenic 451 Anti-oxidant 502 A substance that opposes oxidation or inhibits reactions brought about by dioxygen or peroxides. In European countries, E-numbers for permitted antioxidant food additives are from E 300 to E 324. Antibiotic 147 A substance that kills or slows the growth of microorganisms, including bacteria, viruses, fungi and protozoans. Antitumor 672 A substance that inhibits or prevents the proliferation of neoplasms. Antitumor promoter 673 A substance that inhibits or prevents the proliferation of neoplasms. Cancer preventive 754 A substance that inhibits or prevents the proliferation of neoplasms. Candidicide 756 Cyclooxygenase inhibitor 849 A compound or agent that combines with cyclooxygenases (EC 1.14.99.1) and thereby prevents its substrate-enzyme combination with arachidonic acid and the formation of icosanoids, prostaglandins, and thromboxanes. Fungicide 940 A substance used to destroy fungal pests. Metal chelator 1100 A ligand with two or more separate binding sites that can bind to a single metallic central atom, forming a chelate. Ornithine-decarboxylase inhibitor 1175 A compound or agent that combines with an enzyme in such a manner as to prevent the normal substrate-enzyme combination and the catalytic reaction. Pesticide 1210 Strictly, a substance intended to kill pests. In common usage, any substance used for controlling, preventing, or destroying animal, microbiological or plant pests. Protease inhibitor 1262 A compound which inhibits or antagonizes the biosynthesis or actions of proteases (endopeptidases). Quinone-reductase inducer 1277