STEREOCHEMISTRY OF AN ALCOHOL OXIDASE FROM THE DEFENSIVE SECRETION OF LARVAE OF THE LEAF BEETLE PHAEDON ARMORACIAE (COLEOPTERA: CHRYSOMELIDAE)
作者： Martin Veith , Konrad Dettner , Wilhelm Boland
DOI: 10.1016/0040-4020(96)00298-0
关键词:
摘要: Abstract Larvae of the leaf beetle Phaedon armoraciae produce iridoids chrysomelidial 1 and plagiodial 3 from geraniol 6 by an oxidative sequence identical to that known in plants. Following ω-oxidation resulting 8-hydroxygeraniol 7 is oxidised via 8-oxogeraniol 14 8-hydroxygeranial 15 dialdehyde 8 . In plants this transformation achieved NADP + dependent oxidoreductases. However, defensive secretion several beetles oxygen-dependent oxidase present. The enzyme catalyses removal C(1)- C(8)-H R hydrogen atoms ( Re -specificity) diol yielding 8-oxogeranial
mpg.de
core.ac.uk
uni-bayreuth.de
elsevier.com参考文章(21)
Novel aspects of the biology of Chrysomelidae. Kluwer Academic Publishers Group. ,(1994) , 10.1007/978-94-011-1781-4
Acyclic monoterpene primary alcohol:NADP+ oxidoreductase of Rauwolfia serpentina cells: the key enzyme in biosynthesis of monoterpene alcohols. Journal of Biochemistry. ,vol. 109, pp. 341- 347 ,(1991) , 10.1093/OXFORDJOURNALS.JBCHEM.A123383
Jacques M. Pasteel, Martine Rowell-Rahier, Jean-Claude Braekman, Désiré Daloze, Chemical defences in leaf beetles and their larvae: The ecological, evolutionary and taxonomic significance Biochemical Systematics and Ecology. ,vol. 12, pp. 395- 406 ,(1984) , 10.1016/0305-1978(84)90071-1
Michael Lorenz, Wilhelm Boland, Konrad Dettner, Biosynthesis of iridodials in the defense glands of beetle larvae (Chrysomelinae) Angewandte Chemie. ,vol. 32, pp. 912- 914 ,(1993) , 10.1002/ANIE.199309121
K. Dettner, Defensive secretions and exocrine glands in free-living staphylinid bettles—their bearing on phylogeny (Coleoptera: Staphylinidae) Biochemical Systematics and Ecology. ,vol. 21, pp. 143- 162 ,(1993) , 10.1016/0305-1978(93)90020-R
Chi Huey Wong, George M. Whitesides, Enzyme-catalyzed organic synthesis: regeneration of deuterated nicotinamide cofactors for use in large-scale enzymatic synthesis of deuterated substances Journal of the American Chemical Society. ,vol. 105, pp. 5012- 5014 ,(1983) , 10.1021/JA00353A026
Shinichi Uesato, Hiromitsu Ikeda, Tetsuro Fujita, Hiroyuki Inouye, Meinhart H. Zenk, Elucidation of iridodial formation mechanism - partial purification and characterization of the novel monoterpene cyclase from rauwolfia serpentina cell suspension cultures Tetrahedron Letters. ,vol. 28, pp. 4431- 4434 ,(1987) , 10.1016/S0040-4039(00)96530-4
J. M. Pasteels, S. Duffey, M. Rowell-Rahier, Toxins in chrysomelid beetles Possible evolutionary sequence from de novo synthesis to derivation from food-plant chemicals. Journal of Chemical Ecology. ,vol. 16, pp. 211- 222 ,(1990) , 10.1007/BF01021280
Martin Veith, Michael Lorenz, Wilhelm Boland, Helmut Simon, Konrad Dettner, Biosynthesis of iridoid monoterpenes in insects - defensive secretions from larvae of leaf beetles (coleoptera, chrysomelidae) Tetrahedron. ,vol. 50, pp. 6859- 6874 ,(1994) , 10.1016/S0040-4020(01)81338-7
G. W. Dawson, D. C. Griffiths, N. F. Janes, A. Mudd, J. A. Pickett, L. J. Wadhams, Christine M. Woodcock, Identification of an aphid sex pheromone Nature. ,vol. 325, pp. 614- 616 ,(1987) , 10.1038/325614A0