A diterpene with diverse biological activities
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Totarol

Item No. 26412

Technical Information
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
Purity
≥98%
A crystalline solid
DMF: 2.5 mg/mlDMSO: 3 mg/mlEthanol: 2 mg/ml
λmax
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
Shipping & Storage Information
Storage
-20°C
Shipping
Room temperature in continental US; may vary elsewhere
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    Product Description

    Totarol is a diterpene originally isolated from P. totara that has diverse biological activities, including antibacterial, antioxidant, and neuroprotective properties.1 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).2 It inhibits mitochondrial respiration in P. aeruginosa, inhibiting NADH-cytochrome c, NADH-DPIP, and NADH-coenzyme Q reductases but not cytochrome c oxidase.3 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 (Item No. 90150) with an IC50 value of 9.8 µM.4 In rat primary cerebellar granule cells, totarol increases Akt and GSK-3β phosphorylation when used at a concentration of 5 µM and prevents neuronal death induced by glutamate or oxygen and glucose deprivation.5 It also reduces infarct volume in a rat model of acute cerebral ischemic injury when administered at doses of 1 and 10 microgram/kg.

    WARNING This product is not for human or veterinary use.

    References & Product Citations
    Product Description References

    1. Short, W.F., and Stromberg, H. Totarol. Part I. J. Chem. Soc. 516-520 (1937).

    2. Kubo, I., Muroi, H., and Himehima, M. Antibacterial activity of totarol and its potentiation. J. Nat. Prod. 55(10), 1436-1440 (1992).

    3. Haraguchi, H., Oike, S., Muroi, H., et alMode of antibacterial action of totarol, a diterpene from Podocarpus nagi. Planta Med. 62(2), 122-125 (1996).

    4. Haraguchi, H., Ishikawa, H., and Kubo, I. Antioxidative action of diterpenoids from Podocarpus nagi. Planta Med. 63(3), 213-215 (1997).

    5. Gao, Y., Xu, X., Chang, S., et alTotarol prevents neuronal injury in vitro and ameliorates brain ischemic stroke: Potential roles of Akt activation and HO-1 induction. Toxicol. Appl. Pharmacol. 289(2), 142-154 (2015).