PMID: 9182998May 1, 1997Paper

The two facies of pyrrolizidine alkaloids: the role of the tertiary amine and its N-oxide in chemical defense of insects with acquired plant alkaloids

European Journal of Biochemistry
R LindigkeitT Hartmann

Abstract

Larvae of Creatonotos transiens (Lepidoptera, Arctiidae) and Zonocerus variegatus (Orthoptera, Pyrgomorphidae) ingest 14C-labeled senecionine and its N-oxide with the same efficiency but sequester the two tracers exclusively as N-oxide. Larvae of the non-sequestering Spodoptera littoralis eliminate efficiently the ingested alkaloids. During feeding on the two alkaloidal forms transient levels of senecionine (but not of the N-oxide) are built up in the haemolymph of S. littoralis larvae. Based on these results, senecionine [18O]N-oxide was fed to C. transiens larvae and Z. variegatus adults. The senecionine N-oxide recovered from the haemolymph of the two insects shows an almost complete loss of 18O label, indicating reduction of the orally fed N-oxide in the guts, uptake of the tertiary alkaloid and its re-N-oxidation in the haemolymph. The enzyme responsible for N-oxidation is a soluble mixed function monooxygenase. It was isolated from the haemolymph of the sequestering arctiid Tyria jacobaeae and purified to electrophoretic homogeneity. The enzyme is a flavoprotein with a native Mr of 200000 and a subunit Mr of 51000. It shows a pH optimum at 7.0, has its maximal activity at a temperature of 40-45 degrees C and an isoelectri...Continue Reading

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Citations

Sep 25, 2009·Journal of Chemical Ecology·Annika ReinhardTill Beuerle
Apr 23, 2003·Insect Biochemistry and Molecular Biology·T HartmannJ M Pasteels
Sep 16, 1998·Natural Product Reports·J R Liddel
Mar 2, 2011·Food Additives & Contaminants. Part A, Chemistry, Analysis, Control, Exposure & Risk Assessment·L A P HoogenboomH P Van Egmond
Mar 2, 2011·Food Additives & Contaminants. Part A, Chemistry, Analysis, Control, Exposure & Risk Assessment·Michael Boppré
Dec 1, 2001·Annual Review of Entomology·Ritsuo Nishida
Apr 25, 2002·Proceedings of the National Academy of Sciences of the United States of America·Claudia NaumannDietrich Ober
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Jul 2, 2014·Journal of Chemical Ecology·Tri R NuringtyasKirsten A Leiss
Oct 11, 2014·Phytochemistry·Braulio M FragaAzucena González-Coloma
Jul 21, 2016·Current Opinion in Insect Science·Georg Petschenka, Anurag A Agrawal
Oct 13, 2004·The American Naturalist·Michael S SingerThomas Hartmann
Jun 23, 2012·Phytochemistry·Geoffrey A Cordell
Sep 25, 2015·Plant Cell Reports·Andrew Maxwell P JonesPraveen K Saxena
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Dec 23, 2020·The Science of the Total Environment·Jawameer R Hama, Bjarne W Strobel
Feb 15, 2001·Journal of Natural Products·M ReinaL Villarroel

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