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Details

Stereochemistry ABSOLUTE
Molecular Formula C20H30O
Molecular Weight 286.4516
Optical Activity UNSPECIFIED
Defined Stereocenters 2 / 2
E/Z Centers 0
Charge 0

SHOW SMILES / InChI
Structure of TOTAROL

SMILES

[H][C@@]12CCC3=C(C=CC(O)=C3C(C)C)[C@@]1(C)CCCC2(C)C

InChI

InChIKey=ZRVDANDJSTYELM-FXAWDEMLSA-N
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

HIDE SMILES / InChI

Description
Curator's Comment: Description was created based on several sources, including https://www.ncbi.nlm.nih.gov/pubmed/19755141

Totarol is a meroterpene, and more precisely a terpenophenolic, a chemical compound that is part terpene and part natural phenol. It is a naturally produced diterpene that is bioactive as (+)-totarol. It was first isolated by McDowell and Esterfield from the heartwood of Podocarpus totara, a yew tree found in New Zealand. Totarol showed good activity against Mycobacterium tuberculosis H(37)Rv (MIC of 73.7 uM). It was also most active against the isoniazid-, streptomycin-, and moxifloxacin-resistant variants (MIC of 38.4, 83.4 and 60 uM, respectively). Totarol demonstrated nematicidal and antifouling activities against Caenorhabditis elegans and Artemia salina, it inhibited Leishmania donovani promastigotes, showed good antimicrobial activity against effluxing strains of Staphylococcus aureus. Totarol inhibits bacterial proliferation by targeting FtsZ and it may be useful as a lead compound to develop an effective antitubercular drug.

CNS Activity

Curator's Comment: Totarol prevented glutamate- and oxygen and glucose deprivation-induced neuronal death in primary rat cerebellar granule neuronal cells and cerebral cortical neurons.

Originator

Curator's Comment: Totarol was first isolated by McDowell and Esterfield from the heartwood of Podocarpus totara, a yew tree found in New Zealand.

Approval Year

PubMed

PubMed

TitleDatePubMed
Aromatase inhibitory activities of standishinal and the diterpenoids from the bark of Thuja standishii.
2002 Aug
Novel domino reactions for diterpene synthesis.
2004 Dec 10
The antifungal compound totarol of Thujopsis dolabrata var. hondai seeds selects for fungi on seedling root surfaces.
2007 Dec
Antimycobacterial terpenoids from Juniperus communis L. (Cuppressaceae).
2009 Dec 10
Patents

Sample Use Guides

Rats were intravenously treated with totarol at 2 h, 4 h and 6 h after ischemia onset. Animals were randomly divided into six groups (n = 8–12 per group): Sham, Vehicle, totarol (0.1 ug/kg), totarol (1 ug/kg), totarol (10 ug/kg)
Route of Administration: Intravenous
Totarol demonstrated nematicidal and antifouling activities against Caenorhabditis elegans and Artemia salina at a concentration of 80 ug/mL and 1 ug/mL, respectively.
Name Type Language
TOTAROL
INCI  
INCI  
Official Name English
(4BS-TRANS)-4B,5,6,7,8,8A,9,10-OCTAHYDRO-4B,8,8-TRIMETHYL-1-(1-ISOPROPYL)-2-PHENANTHRENOL
Common Name English
(4AS,10AS)-7-HYDROXY-8-ISOPROPYL-1,1,4A-TRIMETHYL-1,2,3,4,4A,9,10,10A-OCTAHYDROPHENANTHRENE
Common Name English
2-PHENANTHRENOL, 4B,5,6,7,8,8A,9,10-OCTAHYDRO-4B,8,8-TRIMETHYL-1-(1-METHYLETHYL)-, (4BS-TRANS)-
Common Name English
2-PHENANTHRENOL, 4B,5,6,7,8,8A,9,10-OCTAHYDRO-4B,8,8-TRIMETHYL-1-(1-METHYLETHYL)-, (4BS,8AS)-
Common Name English
NSC-299936
Code English
(+)-TOTAROL
Common Name English
TOTAROL [INCI]
Common Name English
TRANS-TOTAROL
Common Name English
PODOCARPA-8,11,13-TRIEN-13-OL, 14-ISOPROPY
Common Name English
Code System Code Type Description
DAILYMED
67NH2854WW
Created by admin on Sat Dec 16 01:28:44 GMT 2023 , Edited by admin on Sat Dec 16 01:28:44 GMT 2023
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EPA CompTox
DTXSID9047752
Created by admin on Sat Dec 16 01:28:44 GMT 2023 , Edited by admin on Sat Dec 16 01:28:44 GMT 2023
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FDA UNII
67NH2854WW
Created by admin on Sat Dec 16 01:28:44 GMT 2023 , Edited by admin on Sat Dec 16 01:28:44 GMT 2023
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RXCUI
1600439
Created by admin on Sat Dec 16 01:28:44 GMT 2023 , Edited by admin on Sat Dec 16 01:28:44 GMT 2023
PRIMARY RxNorm
CAS
511-15-9
Created by admin on Sat Dec 16 01:28:44 GMT 2023 , Edited by admin on Sat Dec 16 01:28:44 GMT 2023
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WIKIPEDIA
TOTAROL
Created by admin on Sat Dec 16 01:28:44 GMT 2023 , Edited by admin on Sat Dec 16 01:28:44 GMT 2023
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MESH
C078548
Created by admin on Sat Dec 16 01:28:44 GMT 2023 , Edited by admin on Sat Dec 16 01:28:44 GMT 2023
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PUBCHEM
92783
Created by admin on Sat Dec 16 01:28:44 GMT 2023 , Edited by admin on Sat Dec 16 01:28:44 GMT 2023
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NSC
299936
Created by admin on Sat Dec 16 01:28:44 GMT 2023 , Edited by admin on Sat Dec 16 01:28:44 GMT 2023
PRIMARY