1.02010-04-08 22:11:29 UTC2019-11-26 03:10:48 UTCFDB014814CarnosolBitter 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-one11,12-Dihydroxy-8,11,13-abietatrien-20,7-olidePicrosalvinC20H26O4330.418330.183109323,4-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-one3,4-dihydroxy-5-isopropyl-11,11-dimethyl-16-oxatetracyclo[6.6.2.0^{1,10}.0^{2,7}]hexadeca-2(7),3,5-trien-15-one5957-80-2CC(C)C1=CC2=C(C(O)=C1O)C13CCCC(C)(C)C1CC2OC3=OInChI=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,5-7,9H2,1-4H3XUSYGBPHQBWGAD-UHFFFAOYSA-N belongs to the class of organic compounds known as diterpene lactones. These are diterpenoids containing a lactone moiety.Diterpene lactonesOrganic compoundsLipids and lipid-like moleculesPrenol lipidsTerpene lactonesAromatic heteropolycyclic compounds1-hydroxy-4-unsubstituted benzenoids2-benzopyransCarbonyl compoundsCarboxylic acid estersDelta valerolactonesDiterpenoidsHydrocarbon derivativesMonocarboxylic acids and derivativesOrganic oxidesOxacyclic compoundsOxanesPhenanthrenes and derivativesTetralins1-hydroxy-4-unsubstituted benzenoid2-benzopyranAromatic heteropolycyclic compoundBenzenoidBenzopyranCarbonyl groupCarboxylic acid derivativeCarboxylic acid esterDelta valerolactoneDelta_valerolactoneDiterpene lactoneDiterpenoidHydrocarbon derivativeIsochromaneLactoneMonocarboxylic acid or derivativesOrganic oxideOrganic oxygen compoundOrganoheterocyclic compoundOrganooxygen compoundOxacycleOxanePhenanthreneTetralinSolidlogp4.35logs-3.92solubility3.95e-02 g/lmelting_pointMp 221-226°logp4.58pka_strongest_acidic9.19pka_strongest_basic-6.1iupac3,4-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-oneaverage_mass330.418mono_mass330.18310932smilesCC(C)C1=CC2=C(C(O)=C1O)C13CCCC(C)(C)C1CC2OC3=OformulaC20H26O4inchiInChI=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,5-7,9H2,1-4H3inchikeyXUSYGBPHQBWGAD-UHFFFAOYSA-Npolar_surface_area66.76refractivity91.43polarizability35.86rotatable_bond_count1acceptor_count3donor_count2physiological_charge0formal_charge0Specdb::MsMs151887Specdb::MsMs151888Specdb::MsMs151889Specdb::MsMs89040Specdb::MsMs89041Specdb::MsMs89042HMDB02121#<Reference:0x00005556740d5b40>#<Reference:0x00005556740d57f8>Black teaType 1CarawayType 1specificCarum carvi480320.00.00.0mg/100 gCeylon cinnamonType 1specificCinnamomum verum1286080.00.00.0mg/100 gClovesType 1specificSyzygium aromaticum2198680.00.00.0mg/100 gCommon sageType 1specificSalvia officinalis38868CuminType 1specificCuminum cyminum524620.00.00.0mg/100 gGingerType 1specificZingiber officinale943280.00.00.0mg/100 gGreen teaType 1Herbal teaType 1Herbs and SpicesUnknowngenericNutmegType 1specificMyristica fragrans510890.00.00.0mg/100 gPepper (Spice)Type 1specificPiper nigrum132160.00.00.0mg/100 gRed teaType 1RosemaryType 1specificRosmarinus officinalis39367284.824998516.6552.999996185mg/100 gStar aniseType 1specificIllicium verum1247780.00.00.0mg/100 gSweet bayType 1specificLaurus nobilis852230.00.00.0mg/100 gTeaType 1specificCamellia sinensis4442bitter5-lipoxygenase inhibitor10A 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 hepatotoxic328Any compound that is able to prevent damage to the liver.anti HIV333A substance that destroys or inhibits replication of viruses.anti inflammatory370A substance that reduces or suppresses inflammation.anti lipoperoxidant407anti mutagenic451anti radicular572antibiotic147A substance that kills or slows the growth of microorganisms, including bacteria, viruses, fungi and protozoans.antioxidant502A 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.antitumor672A substance that inhibits or prevents the proliferation of neoplasms.antitumor promoter673A substance that inhibits or prevents the proliferation of neoplasms.cancer preventive754A substance that inhibits or prevents the proliferation of neoplasms.candidicide756cyclooxygenase inhibitor849A 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.fungicide940A substance used to destroy fungal pests.metal chelator1100A ligand with two or more separate binding sites that can bind to a single metallic central atom, forming a chelate.ornithine-decarboxylase inhibitor1175A compound or agent that combines with an enzyme in such a manner as to prevent the normal substrate-enzyme combination and the catalytic reaction.pesticide1210Strictly, a substance intended to kill pests. In common usage, any substance used for controlling, preventing, or destroying animal, microbiological or plant pests.protease inhibitor1262A compound which inhibits or antagonizes the biosynthesis or actions of proteases (endopeptidases).quinone-reductase inducer1277