Literature DB >> 19052820

Biparental endowment of endogenous defensive alkaloids in Epilachna paenulata.

Soledad Camarano1, Andrés González, Carmen Rossini.   

Abstract

Coccinellid beetles contain a variety of defensive alkaloids that render them unpalatable to predators. Epilachna paenulata (Coleoptera: Coccinellidae) is a South American ladybird beetle that feeds on plants of the Cucurbitaceae family. The defensive chemistry of E. paenulata has been characterized as a mixture of systemic piperidine, homotropane, and pyrrolidine alkaloids. Whole body extracts of adult beetles contain four major alkaloids: 2-(2'-oxopropyl)-6-methylpiperidine (1); 1-(6-methyl-2,3,4,5-tetrahydro-pyridin-2-yl)-propan-2-one (2); 1-methyl-9-azabicyclo[3.3.1]nonan-3-one (3); and 1-(2''-hydroxyethyl)-2-(12'-aminotridecyl)-pyrrolidine (4). Comparative studies of the defensive chemistry of eggs, larvae, pupae, and adults showed differences in alkaloid composition and concentration among life stages. While adults contained mainly the homotropane 1-methyl-9-azabicyclo[3.3.1]nonan-3-one (3), eggs showed the highest concentration of the piperidine 2-(2'-oxopropyl)-6-methylpiperidine (1). We studied the origin of this alkaloid in the eggs by feeding newly emerged, virgin adult beetles with [2-(13)C]-labeled acetate, and by performing crosses between (13)C-fed and unlabeled males and females. GC-MS analysis of alkaloids from (13)C-fed males and females showed high incorporation of (13)C into the alkaloids, as evidenced from a 20-30% increase of isotopic peaks in diagnostic fragment ions, confirming the expected endogenous origin of these alkaloids. In addition, analyses of eggs from different crosses showed that labeled alkaloids from both parents are incorporated into eggs, indicating that E. paenulata males transfer alkaloids to the females at mating. Biparental endowment of chemical defenses into eggs has been shown previously in insects that acquire defensive compounds from dietary sources. To our knowledge, this is the first report of biparental egg endowment of endogenous defenses.

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Year:  2008        PMID: 19052820     DOI: 10.1007/s10886-008-9570-8

Source DB:  PubMed          Journal:  J Chem Ecol        ISSN: 0098-0331            Impact factor:   2.626


  18 in total

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Journal:  J Insect Physiol       Date:  2001-06       Impact factor: 2.354

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3.  Combinatorial chemistry in insects: a library of defensive macrocyclic polyamines.

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Journal:  Science       Date:  1998-07-17       Impact factor: 47.728

4.  Biparental defensive endowment of eggs with acquired plant alkaloid in the moth Utetheisa ornatrix.

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Journal:  Proc Natl Acad Sci U S A       Date:  1988-08       Impact factor: 11.205

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6.  Pyrrolidinoöxazolidine alkaloids from two species of ladybird beetles.

Authors:  P Radford; A B Attygalle; J Meinwald; S R Smedley; T Eisner
Journal:  J Nat Prod       Date:  1997-08       Impact factor: 4.050

7.  Biosynthesis of a defensive insect alkaloid: epilachnene from oleic acid and serine.

Authors:  A B Attygalle; C L Blankespoor; T Eisner; J Meinwald
Journal:  Proc Natl Acad Sci U S A       Date:  1994-12-20       Impact factor: 11.205

8.  In vitro production of adaline and coccinelline, two defensive alkaloids from ladybird beetles (Coleoptera: Coccinellidae).

Authors:  Pascal Laurent; Jean-Claude Braekman; Désiré Daloze; Jacques M Pasteels
Journal:  Insect Biochem Mol Biol       Date:  2002-09       Impact factor: 4.714

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Authors:  J E Carrel; J P Doom; J P McCormick
Journal:  J Chem Ecol       Date:  1986-03       Impact factor: 2.626

10.  Ecological adaptation of an Aristolochiaceae-feeding swallowtail butterfly,Atrophaneura alcinous, to aristolochic acids.

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Journal:  J Chem Ecol       Date:  1989-11       Impact factor: 2.626

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4.  Chemical defense acquired via pharmacophagy can lead to protection from predation for conspecifics in a sawfly.

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  4 in total

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