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Journal of Natural Products
Altshuler, O., Institute of Plant Sciences, ARO, Volcani Center, PO Box 6, Bet-Dagan 50250, Israel
Abu-Abied, M., Institute of Plant Sciences, ARO, Volcani Center, PO Box 6, Bet-Dagan 50250, Israel
Chaimovitsh, D., Division of Aromatic Plants, ARO, Newe ya'Ar, PO Box 1021, Ramat Yishai 30095, Israel
Shechter, A., Division of Aromatic Plants, ARO, Newe ya'Ar, PO Box 1021, Ramat Yishai 30095, Israel
Frucht, H., Division of Aromatic Plants, ARO, Newe ya'Ar, PO Box 1021, Ramat Yishai 30095, Israel
Dudai, N., Division of Aromatic Plants, ARO, Newe ya'Ar, PO Box 1021, Ramat Yishai 30095, Israel
Sadot, E., Institute of Plant Sciences, ARO, Volcani Center, PO Box 6, Bet-Dagan 50250, Israel
Citronellal is a major component of Corymbia citriodora and Cymbopogon nardus essential oils. Herein it is shown that whereas (+)-citronellal (1) is an effective microtubule (MT)-disrupting compound, (-)-citronellal (2) is not. Quantitative image analysis of fibroblast cells treated with 1 showed total fluorescence associated with fibers resembling that in cells treated with the MT-disrupting agents colchicine and vinblastine; in the presence of 2, the fluorescence more closely resembled that in control cells. The distribution of tubulin in soluble and insoluble fractions in the presence of 1 also resembled that in the presence of colchicine, whereas similar tubulin distribution was obtained in the presence of 2 and in control cells. In vitro polymerization of MTs was inhibited by 1 but not 2. Measurements of MT dynamics in plant cells showed similar MT elongation and shortening rates in control and 2-treated cells, whereas in the presence of 1, much fewer and shorter MTs were observed and no elongation or shrinkage was detected. Taken together, the MT system is suggested to be able to discriminate between different enantiomers of the same compound. In addition, the activity of essential oils rich in citronellal is affected by the relative content of the two enantiomers of this monoterpenoid. © 2013 The American Chemical Society and American Society of Pharmacognosy.
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Enantioselective effects of (+)- and (-)-citronellal on animal and plant microtubules
76
Altshuler, O., Institute of Plant Sciences, ARO, Volcani Center, PO Box 6, Bet-Dagan 50250, Israel
Abu-Abied, M., Institute of Plant Sciences, ARO, Volcani Center, PO Box 6, Bet-Dagan 50250, Israel
Chaimovitsh, D., Division of Aromatic Plants, ARO, Newe ya'Ar, PO Box 1021, Ramat Yishai 30095, Israel
Shechter, A., Division of Aromatic Plants, ARO, Newe ya'Ar, PO Box 1021, Ramat Yishai 30095, Israel
Frucht, H., Division of Aromatic Plants, ARO, Newe ya'Ar, PO Box 1021, Ramat Yishai 30095, Israel
Dudai, N., Division of Aromatic Plants, ARO, Newe ya'Ar, PO Box 1021, Ramat Yishai 30095, Israel
Sadot, E., Institute of Plant Sciences, ARO, Volcani Center, PO Box 6, Bet-Dagan 50250, Israel
Enantioselective effects of (+)- and (-)-citronellal on animal and plant microtubules
Citronellal is a major component of Corymbia citriodora and Cymbopogon nardus essential oils. Herein it is shown that whereas (+)-citronellal (1) is an effective microtubule (MT)-disrupting compound, (-)-citronellal (2) is not. Quantitative image analysis of fibroblast cells treated with 1 showed total fluorescence associated with fibers resembling that in cells treated with the MT-disrupting agents colchicine and vinblastine; in the presence of 2, the fluorescence more closely resembled that in control cells. The distribution of tubulin in soluble and insoluble fractions in the presence of 1 also resembled that in the presence of colchicine, whereas similar tubulin distribution was obtained in the presence of 2 and in control cells. In vitro polymerization of MTs was inhibited by 1 but not 2. Measurements of MT dynamics in plant cells showed similar MT elongation and shortening rates in control and 2-treated cells, whereas in the presence of 1, much fewer and shorter MTs were observed and no elongation or shrinkage was detected. Taken together, the MT system is suggested to be able to discriminate between different enantiomers of the same compound. In addition, the activity of essential oils rich in citronellal is affected by the relative content of the two enantiomers of this monoterpenoid. © 2013 The American Chemical Society and American Society of Pharmacognosy.
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