An elicitor of plant volatiles from beet armyworm oral secretion

Science

Volumn 276, Issue 5314, 1997, Pages 945-949

  Alborn, H T ^a   Turlings, T C J ^a,d   Jones, T H ^b   Stenhagen, G ^c   Loughrin, J H ^a,e   Tumlinson, J H ^a  

^a CENTER FOR MEDICAL   (United States)

^b VIRGINIA MILITARY INSTITUTE   (United States)

^c CHALMERS UNIVERSITY OF TECHNOLOGY   (Sweden)

^d UNIVERSITY OF NEUCHÂTEL   (Switzerland)

^e KENTUCKY STATE UNIVERSITY   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

ICOSANOID; UNCLASSIFIED DRUG; VOLICITIN;

AGRICULTURE; ARTICLE; HOST RESISTANCE; INFESTATION; INSECT CONTROL; NONHUMAN; PRIORITY JOURNAL; WASP;

EID: 0030945869     PISSN: 00368075     EISSN: None     Source Type: Journal    
DOI: 10.1126/science.276.5314.945     Document Type: Article

References (40)

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8. 2) was added.
9. 3CN. All fractions were concentrated to near dryness under vacuum (Speed Vac rotary concentrator, Savant Instruments, Farmingdale, NY ) and redissolved in 0.5 ml of 50 mM pH 8 buffer, for bioassay.
10. 2O from 0 to 20 min.
11. 2O and organic phases were separated and concentrated to dryness under vacuum. Bioassay of the fractions redissolved in pH 8 buffer showed all active material to be present in the organic phase, and HPLC analysis (10) showed the peak to be present in this fraction.
12. 2 and then 2 ml of MeOH. The two fractions were concentrated to dryness under vacuum and each redissolved in 0.5 ml of 50 mM pH 8 buffer for bioassay and HPLC analysis.
13. 2O and 1 μl of trifluoroacetic acid (TFA)] was added to a glycerol matrix and analyzed with FAB-MS on a VG Zabspec instrument (VG Analytical, Fison Instruments, Manchester, England). To obtain sodium adducts, we replaced the TFA with 1 μl of a 1 M sodium chloride solution. High-resolution mass measurements were obtained by adding polyethylene glycol (1 μl) with an average mass of 400 daltons (PEG 400) to the glycerol matrix to give reference ions of known mass for calibration of the mass scale. Possible elemental compositions were established allowing a maximum of 30 carbons, 2 to 8 oxygens, and 2, 4, or 6 nitrogens. The mass window for the calculations was limited to an error of 10 milli mass units. Daughter ion spectra were obtained from samples in the same FAB matrix as above with a tandem four-sector mass spectrometer (JEOL HX/ HX110A, Tokyo, Japan). The nitrogen collision gas was adjusted to give a 60% reduction in intensity of the mother ion.
14. National Institute of Standards and Technology (Gaithersburg, MD), mass spectral library on CD-ROM, version 1.0, January 1995. Characteristic ions for glutamine are m/z 130, 129, 101, 84 (base peak), and 56.
15. 2 was added and the sample was analyzed by GC/MS.
16. 4 for chemical ionization. The ion source temperature was 200°C in both El and Cl mode.
17. The acetate had a shorter retention time (26.06 min) on the polar OV-351 column than the hydroxy acid methyl ester (27.55 min), but a longer retention time (25.54 min) than the hydroxy acid methyl ester (25.38 min) on a nonpolar column (DB1, 25 m long, 0.25-mm ID, J&W Scientific, Folsom, CA). The Cl mass spectrum showed ions at m/z 351 (weak) (M + 1), m/z 309 (weak) (loss of MeOH), m/z 291 (base peak) (loss of acetic acid), and m/z 259 (loss of both MeOH and acetic acid).
18. 2 and the temperature program the same as in (16).
19. 2O before being analyzed by GC/MS (24).
20. Partially reduced hydroxy acid methyl ester (19) was ozonized following the procedures of M. Beroza and B. Bierl [Anal. Chem. 38, 1976 (1966); ibid. 39, 1131 (1967)] and the product analyzed by GC/MS (16).
21. Partially reduced hydroxy acid methyl ester (19) was ozonized following the procedures of M. Beroza and B. Bierl [Anal. Chem. 38, 1976 (1966); ibid. 39, 1131 (1967)] and the product analyzed by GC/MS (16).
22. 2 through the solution for 18 hours. A pyrrolidide derivative of the saturated methyl ester was prepared following the procedures of B. Å. Andersson [Prog. Chem. Fats Other Lipids 16, 279 (1978)].
23. Racemic 17-hydroxy linolenic acid was synthesized (Fig. 3) by the condensation of the appropriate triphenylphosphonium ylid, prepared from the alkyl triphenylphosphonium iodide by the silazide method [H. J. Bestman, W. Stransky, O. Vostrowsky, Chem. Ber. 109, 1694 (1976); H. J. Bestman et al., Liebigs Ann. Chem. 1987 417 (1987)], with methyl 9-oxononanoate [F. C. Pennington, W. D. Clemer, W. M. McLamore, V. V. Bogert, I. A. Solomons, J. Am. Chem. Soc. 75, 109 (1953)]. The phosphonium salt was obtained by standard methodology from the ethoxy ethyl ether of 3,6-heptadiyn-1-ol [W. Huang, S. P. Pulaski, G. Meinwald, J. Org. Chem. 48, 2270 (1983)] by sequential condensation with acetaldehyde and benzoyl chloride, followed by deprotection, partial hydrogenation, and conversion of the primary alcohol to the phosphonium iodide.
24. Racemic 17-hydroxy linolenic acid was synthesized (Fig. 3) by the condensation of the appropriate triphenylphosphonium ylid, prepared from the alkyl triphenylphosphonium iodide by the silazide method [H. J. Bestman, W. Stransky, O. Vostrowsky, Chem. Ber. 109, 1694 (1976); H. J. Bestman et al., Liebigs Ann. Chem. 1987 417 (1987)], with methyl 9-oxononanoate [F. C. Pennington, W. D. Clemer, W. M. McLamore, V. V. Bogert, I. A. Solomons, J. Am. Chem. Soc. 75, 109 (1953)]. The phosphonium salt was obtained by standard methodology from the ethoxy ethyl ether of 3,6-heptadiyn-1-ol [W. Huang, S. P. Pulaski, G. Meinwald, J. Org. Chem. 48, 2270 (1983)] by sequential condensation with acetaldehyde and benzoyl chloride, followed by deprotection, partial hydrogenation, and conversion of the primary alcohol to the phosphonium iodide.
25. Racemic 17-hydroxy linolenic acid was synthesized (Fig. 3) by the condensation of the appropriate triphenylphosphonium ylid, prepared from the alkyl triphenylphosphonium iodide by the silazide method [H. J. Bestman, W. Stransky, O. Vostrowsky, Chem. Ber. 109, 1694 (1976); H. J. Bestman et al., Liebigs Ann. Chem. 1987 417 (1987)], with methyl 9-oxononanoate [F. C. Pennington, W. D. Clemer, W. M. McLamore, V. V. Bogert, I. A. Solomons, J. Am. Chem. Soc. 75, 109 (1953)]. The phosphonium salt was obtained by standard methodology from the ethoxy ethyl ether of 3,6-heptadiyn-1-ol [W. Huang, S. P. Pulaski, G. Meinwald, J. Org. Chem. 48, 2270 (1983)] by sequential condensation with acetaldehyde and benzoyl chloride, followed by deprotection, partial hydrogenation, and conversion of the primary alcohol to the phosphonium iodide.
26. Racemic 17-hydroxy linolenic acid was synthesized (Fig. 3) by the condensation of the appropriate triphenylphosphonium ylid, prepared from the alkyl triphenylphosphonium iodide by the silazide method [H. J. Bestman, W. Stransky, O. Vostrowsky, Chem. Ber. 109, 1694 (1976); H. J. Bestman et al., Liebigs Ann. Chem. 1987 417 (1987)], with methyl 9-oxononanoate [F. C. Pennington, W. D. Clemer, W. M. McLamore, V. V. Bogert, I. A. Solomons, J. Am. Chem. Soc. 75, 109 (1953)]. The phosphonium salt was obtained by standard methodology from the ethoxy ethyl ether of 3,6-heptadiyn-1-ol [W. Huang, S. P. Pulaski, G. Meinwald, J. Org. Chem. 48, 2270 (1983)] by sequential condensation with acetaldehyde and benzoyl chloride, followed by deprotection, partial hydrogenation, and conversion of the primary alcohol to the phosphonium iodide.
27. 3CN in 0.4 mM ammonium acetate buffer (Aldrich) at a flow rate of 1.2 ml/min. The retention time of the synthetic and natural elicitor was identical.
28. 3CN in 0.4 mM ammonium acetate buffer (Aldrich) at a flow rate of 1.2 ml/min. The retention time of the synthetic and natural elicitor was identical.
29. 3CN in 0.4 mM ammonium acetate buffer (Aldrich) at a flow rate of 1.2 ml/min. The retention time of the synthetic and natural elicitor was identical.
30. 3CN in 10 mM ammonium acetate buffer, pH 4.5, at a flow rate of 1 ml/min (10). The synthetic L-form had a retention time of 5.25 min, identical to that of the natural elicitor, and the D-form had a retention time of 9.03 min.
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34. J. H. Loughrin, A. Manukian, R. R. Heath, T. C. J. Turlings, J. H. Tumlinson, Proc. Natl. Acad. Sci. U.S.A. 91, 11836 (1994).
35. U. S. R. Röse, A. Manukian, R. R. Heath, J. H. Tumlinson, Plant Physiol. 111, 487 (1996).
36. P. W. Pare and J. H. Tumlinson, Nature 385, 30 (1997).
37. T. C. J. Turlings and J. H. Tumlinson, Proc. Natl. Acad. Sci. U.S.A. 89, 8399 (1992).
38. L. Mattiacci, M. Dicke, M. A. Posthumus, ibid. 92, 2036 (1995).
39. Significant differences in relative release rates of volatiles were tested by Tukey's studentized range test after analysis of variance with a significance level of 5% (SYSTAT, Systat Inc., Evanston, IL).
40. This project was funded in part by a grant from the Swedish Natural Science Research Council. We thank H. Karlsson, A. T. Proveaux, and D. Powell for assistance with mass spectrometric analysis, J. Lockerman and S. Sharp for oral secretion collection, and M. Brennan for technical assistance. We also thank J. G. Millar, C. A. Ryan, and G. G. Still for helpful comments on the manuscript.