Abstract
Bruchins are 3-hydroxypropanoate esters of long-chain α,ω-diols from pea weevils and cowpea weevils that have been shown to initiate callus formation on pea pods at extremely low application rates. Synthetic analogs have been prepared and examined to evaluate structural requirements for inducing this unusual neoplastic response. Chain length (optimum length C22–C24) is important, whereas unsaturation within the chain is relatively unimportant. Difunctionality is required for maximum activity, but the α,ω-diols themselves are inactive. Most critical is the ester portion(s) of the molecules; 3-hydroxypropanoate esters are far more active than any analogs examined.
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REFERENCES
Bartelt, R. J., CossÉ, A. A., Petroski, R. J., and Weaver, D. K. 2002. Cuticular hydrocarbons and novel alkenediol diacetates from wheat stem sawfly (Cephus cinctus): natural oxidation to pheromone components. J. Chem. Ecol. 28:385–405.
Berdnikov, V. A., Trusov, Y. A., Bogdanova, V. S., Kosterin, O. E., Rozov, S. M., Nedel'kina, S. V., and Nikulina, Y. N. 1992. The neoplastic pod gene (Np) may be a factor for resistance to the pest Bruchis pisorum L. Pisum Genet. 24:37–39.
CossÉ, A. A., Bartelt, R. J., Weaver, D. K., and Zilkowski, B. W. 2002. Pheromone components of the wheat stem sawfly: identification, electrophysiology, and field bioassay. J. Chem. Ecol. 28:407–423.
Doss, R. P., Proebsting, W. M., Potter, S. W., and Clement, S. L. 1995. Response of Np Mutant of pea (Pisum sativum L.) to pea weevil (Bruchus pisorum L.) oviposition and extracts. J. Chem. Ecol. 21:97–106.
Doss, R. P., Oliver, J. E., Proebsting, W. M., Potter, S. W., Kuy, S.-R., Clement, S. L., Williamson, R. T., Carney, J. R., and DeVilbiss, E. D. 2000. Bruchins: Insect-derived plant regulators that stimulate neoplasm formation. Proc. Natl. Acad. Sci. USA 97:6218–6223.
Meicenheimer, R. D. and Muehlbauer, F. J. 1982. Growth and developmental stages of Alaska peas. Exp. Agric. 18:17–27. BRUCHINS 2513
Oliver, J. E., Doss, R. P., Williamson, R. T., Carney, J. R., and DeVilbiss, E. D. 2000. Bruchins—mitogenic 3-(hydroxypropanoyl) esters of long chain diols from weevils of the Bruchidae. Tetrahedron 56:7633–7641.
Phillips, T.W., Phillips, J. K., Webster, F. X., Tang, R., and Burkholder, W. E. 1996. Identification of sex pheromones from cowpea weevil, Callosobruchus maculatus, and related studies with C. analis (Coleoptera:Bruchidae). J. Chem. Ecol. 22:2233–2249.
POULAIN, S., NOIRET, N., and PATIN, H. 1996. An easy access to symmetrical Z-olefins from phosphorous ylides. Tetrahedron Lett. 37:7703–7706.
SNOAD, B. and MATTHEWS, P. 1969. Neoplasms of the pea pod, pp. 126–131, in C. D. Darlington and K. R. Lewis (eds.)., Chromosomes Today. Oliver Boyd, Edinburgh.
SONNET, P. E. and OLIVER, J. E. 1976. Olefin inversion. I. Reaction of aliphatic epoxides with triphenylphosphine dihalides. J. Org. Chem. 41:3279–3283.
UENO, Y., YAMASAKI, A., TERAUCHI, H., and TAKEMURA, S. 1974, Reaction of N-haloamide. XX. Bromo-formylation of α, β-unsaturated esters with N,N-dibromobenzenesulfonamide and formic acid. Chem. Pharm. Bull. 22:1646–1651.
ZWEIFEL, G. and POLSTON, N. L. 1970, Selective hydroboration of conjugated diynes with dialkyl boranes. A convenient route to conjugated cis-enynes, α, β-acetylenic ketones, and cis,cis-dienes. J. Am. Chem. Soc. 92:4068–4071.
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Oliver, J.E., Doss, R.P., Marquez, B. et al. Bruchins, Plant Mitogens from Weevils: Structural Requirements for Activity. J Chem Ecol 28, 2503–2513 (2002). https://doi.org/10.1023/A:1021436119421
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DOI: https://doi.org/10.1023/A:1021436119421