Structure Database (LMSD)

Common Name
(+)-Totarol
Systematic Name
(+)-8,11,13-totara-trien-13-ol
Synonyms
LM ID
LMPR0104070001
Formula
Exact Mass
Calculate m/z
286.229665
Status
Curated


Classification

Biological Context

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 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.

This information has been provided by Cayman Chemical

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

References

Taxonomy Information

Curated from
NCBI taxonomy class
Reference
Podocarpus totara (#56901)
Pinopsida (#58019)
Totarol. Part II,
J Chem Soc, 1951

String Representations

InChiKey (Click to copy)
ZRVDANDJSTYELM-FXAWDEMLSA-N
InChi (Click to copy)
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
SMILES (Click to copy)
C1CC[C@]2(C)C3C=CC(O)=C(C(C)C)C=3CC[C@@]2([H])C1(C)C

Other Databases

Wikipedia
CHEBI ID
PubChem CID
Cayman ID

Calculated Physicochemical Properties

Heavy Atoms 21
Rings 3
Aromatic Rings 1
Rotatable Bonds 1
Van der Waals Molecular Volume 307.45
Topological Polar Surface Area 20.23
Hydrogen Bond Donors 1
Hydrogen Bond Acceptors 1
logP 5.55
Molar Refractivity 88.99

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Created at
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Updated at
6th Feb 2024