Abstract
Several terpenes as well as synthetic analogues were screened for activity against Mycobacterium tuberculosis in vitro using the microplate alamar blue assay. Geranylgeraniol (MIC 1.56 μg/mL) and geranylgeranyl acetate (MIC 3.13 μg/mL) were identified as potent and selective inhibitors of M. tuberculosis .
Abbreviations
clogP :calculated log octanol/water partition coefficient
MABA:microplate alamar blue assay
MIC:minimum inhibitory concentration
References
1
Cantrell C L, Franzblau S G, Fischer N H.
Antimycobacterial plant terpenoids.
Planta Med.
2001;
67
685-94.
2
Copp B R, Pearce A N.
Natural product growth inhibitors of Mycobacterium tuberculosis
.
Nat Prod Rep.
2007;
24
278-97.
3
Dye C.
Global epidemiology of tuberculosis.
Lancet.
2006;
367
938-40.
4
Utenova B T, Gundersen L L.
Synthesis of (+)-agelasine D from (+)-manool.
Tetrahedron Lett.
2004;
45
4233-5.
5
Bakkestuen A K, Gundersen L L, Petersen D, Utenova B T, Vik A.
Synthesis and antimycobacterial activity of agelasine E and analogs.
Org Biol Chem.
2005;
3
1025-33.
6
Vik A, Hedner E, Charnock C, Samuelsen Ø, Larsson R, Gundersen L L. et al .
(+)-Agelasine D: Improved synthesis and evaluation of antibacterial and cytotoxic activities.
J Nat Prod.
2006;
69
381-6.
7
Vik A, Hedner E, Charnock C, Tangen L W, Samuelsen Ø, Larsson R. et al .
Antimicrobial and cytotoxic activity of agelasine and agelasimine analogs.
Bioorg Med Chem.
2007;
15
4016-37.
8
Rajab M S, Cantrell C L, Franzblau S G, Fisher N H.
Antimycobacterial activity of (E )-phytol and derivatives. A preliminary structure-activity study.
Planta Med.
1998;
64
2-4.
9
Topcu G, Erenler R, Cakmak O, Johansson C B, Celik C, Chai H B. et al .
Diterpenes from the berries of Juniperus excelsa
.
Phytochemistry.
1999;
50
1195-9.
10
Kubo I, Muroi H, Kubo A.
Antibacterial activity of long-chain alcohols against Streptococcus mutans
.
J Agric Food Chem.
1993;
41
2447-50.
11
Inoue Y, Hada T, Shiraishi A, Hirose K, Hamashima H, Kobayashi S.
Biphasic effects of geranylgeraniol, teprenone, and phytol on the growth of Staphylococcus aureus
.
Antimicrob Agents Chemother.
2005;
49
1770-4.
12
Nahmany M, Melman A.
Studies on the synthesis of DNA-damaging part of leinamycin: regioselectivity in Ti(OiPr)4 mediated opening of hydroxy epoxides with carboxylic acids.
Tetrahedron.
2005;
61
7481-8.
13
Bakkestuen A K, Gundersen L L.
Synthesis of (+)-trixagol, the enantiomer of the (-)-agelasine E terpenoid side chain.
Tetrahedron.
2003;
59
115-21.
14 Clark J S, Myatt J, Wilson C, Roberts L, Walshe N. Exploration of the biomimetic synthesis of indole-diterpene mycotoxins: an unexpected cascade reaction during the attempted synthesis of emindole SB. Chem Commun 2003: 1546-7.
15
Völkert M, Uwai K, Tebbe A, Popkirova B, Wagner M, Kuhlmann J. et al .
Synthesis and biological activity of photoactivatable N-Ras peptides and proteins.
J Am Chem Soc.
2003;
125
12 749-58.
16
Khomenko T M, Tatarova L E, Korchagina D V, Barkhash V A.
Rearrangements of epoxides of linalool and nerolidyl acetate in acid media.
Russ J Org Chem.
2002;
38
498-506.
Prof. Lise-Lotte Gundersen
Department of Chemistry
University of Oslo
P.O. Box 1033
Blindern
N-0315 Oslo
Norway
Phone: +47-228-57-019
Fax: +47-228-55-507
Email: l.l.gundersen@kjemi.uio.no