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Tomato-produced 7-epizingiberene and R-curcumene act as repellents to whiteflies
Authors:Bleeker Petra M  Diergaarde Paul J  Ament Kai  Schütz Stefan  Johne Bettina  Dijkink Jan  Hiemstra Henk  de Gelder René  de Both Michiel T J  Sabelis Maurice W  Haring Michel A  Schuurink Robert C
Affiliation:a University of Amsterdam, Dept. of Plant Physiology, Science Park 904, 1098 XH, Amsterdam, The Netherlands
b Keygene NV, Agrobusiness Park 90, P.O. Box 216, 6700 AE, Wageningen, The Netherlands
c University of Göttingen, Dept. of Forest Zoology and Forest Conservation, Buesgenweg 3, 37077 Göttingen, Germany
d University of Amsterdam, Dept. of Synthetic Organic Chemistry, Nieuwe Achtergracht 129, 1018 WS, Amsterdam, The Netherlands
e Radboud University, Institute for Molecules and Materials, Heyendaalseweg 135, 6525 AJ, Nijmegen, The Netherlands
f University of Amsterdam, Institute for Biodiversity and Ecosystem Dynamics, Science Park 904, 1098 XH, Amsterdam, The Netherlands
Abstract:How whiteflies (Bemisia tabaci) make the choice for a host plant prior to landing, is not precisely known. Here we investigated whether they respond to specific volatiles of tomato. Zingiberene and curcumene were purified from Solanum habrochaites (PI127826), characterised by NMR and X-ray analysis and identified as 7-epizingiberene and R-curcumene. In contrast, oil from Zingiber officinalis contained the stereoisomers zingiberene and S-curcumene, respectively. Using a combination of free-choice bio-assays and electroantennography, 7-epizingiberene and its dehydrogenated derivative R-curcumene were shown to be active as semiochemicals to B. tabaci adults, whereas the stereoisomers from ginger were not. In addition, R-curcumene elicited the strongest electroantennographic response. Bio-assays showed that a cultivated tomato could be made less attractive to B. tabaci than its neighbouring siblings by the addition of the tomato stereoisomer 7-epizingiberene or its derivative R-curcumene. These sesquiterpenes apparently repel adult whiteflies prior to landing, presumably because it informs them that after landing they, or their offspring, may be exposed to higher and lethal concentrations of the same compounds.
Keywords:Solanum lycopersicum   Solanum habrochaites   Whitefly   Plant volatiles   Host selection   7-Epizingiberene   R-Curcumene   Stereoisomer   Electroantennography
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