Abstract
Zwiebelane A (cis-2,3-dimethyl-5,6-dithiabicyclo[2.1.1]hexane 5-oxide), a natural product of onion bulbs (Allium cepa L.), is found to enhance the potential fungicidal activity of polymyxin B (PMB). As is the case with allicin, an allyl sulfur compound from garlic, zwiebelane A amplifies the disruptive effect of PMB on the vacuole of Saccharomyces cerevisiae, which has been found to represent a target for antifungal agents.
Key words
Allium cepa
- Alliaceae - zwiebelane A - polymyxin B -
Saccharomyces cerevisiae
References
-
1
Ankri S, Mirelman D.
Antimicrobial properties of allicin from garlic.
Microbes Infect.
1999;
1
125-129
-
2
Oommen S, Anto R J, Srinivas G, Karunagaran D.
Allicin (from garlic) induces caspase-mediated apoptosis in cancer cells.
Eur J Pharmacol.
2004;
485
97-103
-
3
Coppi A, Cabinan M, Mirelman D, Sinnis P.
Antimalarial activity of allicin, a biologically active compound from garlic cloves.
Antimicrob Agents Chemother.
2006;
50
1731-1737
-
4
Ogita A, Fujita K, Taniguchi M, Tanaka T.
Enhancement of the fungicidal activity of amphotericin B by allicin, an allyl-sulfur compound from garlic, against the yeast Saccharomyces cerevisiae as a model system.
Planta Med.
2006;
72
1247-1250
-
5
Ogita A, Matsumoto K, Fujita K, Usuki Y, Hatanaka Y, Tanaka T.
Synergistic fungicidal activities of amphotericin B and N-methyl-N"-dodecylguanidine: a constituent of polyol macrolide antibiotic niphimycin.
J Antibiot.
2007;
60
27-35
-
6
Ogita A, Fujita K, Tanaka T.
Enhancement of the fungicidal activity of amphotericin B by allicin: effects on intracellular ergosterol trafficking.
Planta Med.
2009;
75
222-226
-
7
Borjihan H, Ogita A, Fujita K, Hirasawa E, Tanaka T.
The vacuole-targeting fungicidal activity of amphotericin B against the pathogenic fungus Candida albicans and its enhancement by allicin.
J Antibiot.
2009;
62
691-697
-
8
Ogita A, Fujita K, Usuki Y, Tanaka T.
Targeted yeast vacuole disruption by polyene antibiotics with a macrocyclic lactone ring.
Int J Antimicrob Agents.
2010;
35
89-92
-
9
Ogita A, Nagao Y, Fujita K, Tanaka T.
Amplification of vacuole-targeting fungicidal activity of antibacterial antibiotic polymyxin B by allicin, an allyl sulfur compound from garlic.
J Antibiot.
2007;
60
511-518
-
10
Ogita A, Konishi Y, Borjihan B, Fujita K, Tanaka T.
Synergistic fungicidal activities of polymyxin B and ionophores, and their dependence on direct disruptive action of polymyxin B on fungal vacuole.
J Antibiot.
2009;
62
81-87
-
11
Bayer T, Wagner H, Block E, Grisoni S, Zhao S H, Neszmelyi A.
Zwiebelanes: novel biologically active 2,3-dimethyl-5,6-dithiabicyclo[2.1.1.]hexane-5-oxides from onion.
J Am Chem Soc.
1989;
111
3085-3086
-
12
Thumm M.
Structure and function of the yeast vacuole and its role in autophagy.
Microsc Res Tech.
2000;
51
563-572
-
13
Davis S R.
An overview of the antifungal properties of allicin and its breakdown products – the possibility of a safe and effective antifungal prophylactic.
Micoses.
2005;
48
95-100
-
14
Davies H M L, Huby N J S, Cantrell W R, Olive J L.
Alpha-hydroxy esters as chiral auxiliaries in asymmetric cyclopropanations by rhodium (II)-stabilized vinylcarbenoids.
J Am Chem Soc.
1993;
115
9468-9479
Univ.-Prof. Dr. Toshio Tanaka
Department of Bio- and Geosciences
Graduate School of Science
Osaka City University
3–3–138 Sugimoto
Sumiyoshi-ku, Osaka 558–8585
Japan
Telefon: + 81 6 66 05 31 63
Fax: + 81 6 66 05 31 64
eMail: tanakato@sci.osaka-cu.ac.jp