coccinellidae; alkaloid biosynthesis; labelling; glutamine; fat body
Abstract :
[en] In vitro experiments using [1-C-14] and [2-C-14] acetate were devised to study the biosynthesis of the defensive coccinellid alkaloids adaline and coccinelline in Adalia 2-punctata and Coccinella 7-punctata, respectively. The labelled alkaloids obtained in these experiments had a specific activity about ten times higher than that of the samples obtained in feeding experiments. This in vitro assay has enabled us to demonstrate that these two alkaloids are most likely biosynthesised through a fatty acid rather than a polyketide pathway, that glutamine is the preferred source of the nitrogen atom and that alkaloid biosynthesis takes place in the insect fat body.
Disciplines :
Chemistry
Author, co-author :
Laurent, Pascal ; Université de Liège - ULiège > Chimie et bio-industries > Chimie biologique industrielle
Braekman, Jean-Claude
Daloze, Désiré
Pasteels, Jacques
Language :
English
Title :
In vitro production of adaline and coccinelline, two defensive alkaloids from ladybird beetles (Coleoptera : Coccinellidae)
Publication date :
2002
Journal title :
Insect Biochemistry and Molecular Biology
ISSN :
0965-1748
eISSN :
1879-0240
Publisher :
Pergamon Press - An Imprint of Elsevier Science, Oxford, United Kingdom
Attygalle A.B., Xu S.C., McCormick K.D., Meinwald J. (1993) Alkaloids of the Mexican bean beetle, Epilachna varivestis (Coccinellidae). Tetrahedron 49:9333-9342.
Attygalle A.B., Blankespoor C.L., Eisner T., Meinwald J. (1994) Biosynthesis of a defensive insect alkaloid: Epilachnene from oleic acid and serine. Proc. Natl. Acad. Sci. USA 91:12790-12793.
Attygalle A.B., Svatos A., Veith M., Farmer J.J., Meinwald J., Smedley S., Gonzales A., Eisner T. (1999) Biosynthesis of epilachnene, a macrocyclic defensive alkaloid of the Mexican bean beetle. Tetrahedron 55:955-966.
Braconnier M.F., Braekman J.C., Daloze D., Pasteels J.M. (1985) (Z)-1,17-diaminooctadec-9-ene, a novel aliphatic diamine from Coccinellidae. Experientia 41:519-520.
Braekman J.C., Charlier A., Daloze D., Heilporn S., Pasteels J.M., Plasman V., Wang S.F. (1999) New piperidine alkaloids from two ladybird beetles of the genus Calvia (Coccinellidae). Eur. J. Org. Chem. 1749-1755.
Chapman R.F. The insects. Structure and function , Cambridge University Press, Cambridge; 1998, 132-140.
Daloze D., Braekman J.C., Pasteels J.M. (1995) Ladybird defence alkaloids: Structural chemotaxonomic and biosynthetic aspects (Col.: Coccinellidae). Chemoecology 5-6:173-183.
Huang Q., Attygalle A.B., Meinwald J., Houck M.A., Eisner T. (1998) Chilocorine C. A new "dimeric" alkaloid from a coccinellid beetle, Chilocorus cacti. J. Nat. Prod. 61:598-601.
Ivarsson P., Blomquist G.J., Seybold S.J. (1997) In vitro production of the pheromone intermediates ipsdienone and ipsenone by the bark beetles Ips pini (Say) and I. paraconfusus Lanier (Coleoptera: Scolytidae). Naturwissensch. 84:454-457.
King G.A., Meinwald J. (1996) Review of the defensive chemistry of coccinellids. Chem. Rev. 96:1105-1122.
Laurent P., Lebrun B., Braekman J.C., Daloze D., Pasteels J.M. (2001) Biosynthetic studies on adaline and adalinine, two alkaloids from ladybird beetles (Coleoptera: Coccinellidae). Tetrahedron 57:3403-3412.
Leete E., Olson J.O. (1972) Biosynthesis and metabolism of the hemlock alkaloids. J. Am. Chem. Soc. 94:5472-5477.
Luckner M. Secondary Metabolism in Microorganisms, Plants, and Animals , Springer Verlag, Berlin; 1984, 54-99.
Luckner M. Biochemistry of Alkaloids , Springer Verlag, Berlin; 1985, 66-67.
Massière F., Badet-Denisot M.A. (1998) The mechanism of glutamine-dependent amidotransferases. Cell. and Mol. Life Sci. 54:205-222.
McCormick K.D., Attygalle A.B., Xu S.C., Svatos A., Meinwald J., Houck M.A., Blankespoor C.L., Eisner T. (1994) Chilocorine: Heptacyclic alkaloid from a coccinellid beetle. Tetrahedron 50:2365-2372.
Radfort P., Attygalle A.B., Meinwald J., Smedley S.R., Eisner T. (1997) Pyrrolidinooxazolidine alkaloids from two species of ladybird beetles. J. Nat. Prod. 60:755-759.
Renson B., Merlin P., Daloze D., Braekman J.C., Roisin Y., Pasreels J.M. (1994) Biosynthesis of tetraponerine-8, a defence alkaloid of the ant Tetraponera sp. Can. J. Chem. 72:105-109.
Robinson J.D., Brady R.O., Bradley R.M. (1963) Biosynthesis of fatty acids: IV, Studies with inhibitors. J. Lipid Res. 4:144-150.
Shi X., Attygalle A.B., Meinwald J., Houck M.A., Eisner T. (1995) Spirocyclic defensive alkaloids from a coccinellid beetle. Tetrahedron 51:8711-8718.
Timmermans M., Braekman J.C., Daloze D., Pasteels J.M., Merlin J., Declercq J.P. (1992) Exochomine, a dimeric ladybird alkaloid, isolated from Exochomus quadripustulatus (Coleoptera: Coccinellidae). Tetrahedon Lett. 33:1281-1284.
Tursch B., Daloze D., Braekman J.C., Hootelé C., Pasteels J.M. (1975) Chemical ecology of arthropods - X. The structure of myrrhine and the biosynthesis of coccinelline. Tetrahedron 31:1541-1543.
Wang S.F., Braekman J.C., Daloze D., Pasteels J.M. (1996) Signatipermine: A new alkaloid from the New Guinean ladybird Epilachna signatipennis (Coccinellidae). Bull. Soc. Chim. Belges 105:483-487.