Totarol

Totarol is a diterpene originally isolated from P. totara that has diverse biological activities, including antibacterial, antioxidant, and neuroprotective properties. It is active against Gram-positive bacteria, including P. acnes, S. mutans, B. subtilis, and B. ammoniagenes (MICs = 0.39, 0.78, 1.56, and 0.78 µg/ml, respectively), as well as penicillin-resistant and -susceptible strains of S. aureus (MICs = 0.78 and 1.56 µg/ml, respectively). It inhibits mitochondrial respiration in P. aeruginosa, inhibiting NADH-cytochrome c, NADH-DPIP, and NADH-coenzyme Q reductases but not cytochrome c oxidase. Totarol inhibits Fe(III)-ADP/NADPH-induced lipid oxidation in rat liver microsomes and mitochondria (IC50s = 4.79 and 0.47 µM, respectively) and autooxidation of linoleic acid (Cay-90150) with an IC50 value of 9.8 µM. In rat primary cerebellar granule cells, totarol increases Akt and GSK-3beta phosphorylation when used at a concentration of 5 µM and prevents neuronal death induced by glutamate or oxygen and glucose deprivation. It also reduces infarct volume in a rat model of acute cerebral ischemic injury when administered at doses of 1 and 10 microgram/kg.Formal Name: (4bS,8aS)-4b,5,6,7,8,8a,9,10-octahydro-4b,8,8-trimethyl-1-(1-methylethyl)-2-phenanthrenol. CAS Number: 511-15-9. Synonyms: NSC 299936, (+)-Totarol, trans-Totarol. Molecular Formula: C20H30O. Formula Weight: 286.5. Purity: >98%. Formulation: (Request formulation change), A crystalline solid. Solubility: DMF: 2.5 mg/ml, DMSO: 3 mg/ml, Ethanol: 2 mg/ml. lambdamax: 281 nm. SMILES: OC(C=C1)=C(C(C)C)C2=C1[C@]3(C)[C@](CC2)([H])C(C)(C)CCC3. InChi Code: InChI=1S/C20H30O/c1-13(2)18-14-7-10-17-19(3,4)11-6-12-20(17,5)15(14)8-9-16(18)21/h8-9,13,17,21H,6-7,10-12H2,1-5H3/t17-,20+/m0/s1. InChi Key: ZRVDANDJSTYELM-FXAWDEMLSA-N. Origin: Plant/Podocarpus totara.