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Identification and Synthesis of Volicitin and Related Components from Beet Armyworm Oral Secretions

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Abstract

Oral secretion of beet armyworm caterpillars (BAW), when applied to damaged tissues of corn seedlings, induces the seedlings to emit volatile compounds that attract the natural enemies of the caterpillars. The key elicitor present in BAW oral secretions is N-[17-hydroxylinolenoyl]-L-glutamine (volicitin). Analysis of the oral secretion showed that it also contained N-[17-hydroxyolinoleoyl]-L-glutamine, free 17-hydroxylinolenic, and 17-hydroxylinoleic acid, the glutamine conjugates of linolenic and linoleic acid as well as free linolenic and linoleic acid. Here we present the identification and synthesis of the hydroxy acids and of glutamine conjugates.

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REFERENCES

  • Alborn,Ñ H.ÑT.,Ñ Rose,Ñ U.ÑS.ÑR.,ÑandÑ McAuslane,Ñ H.ÑJ.Ñ1996.ÑSystemicÑinductionÑofÑfeedingÑdeterrentsÑinÑcottonÑplantsÑbyÑfeedingÑofÑSpodopteraÑspp.Ñlarvae.ÑJ.ÑChem.ÑEcol.Ñ22:919–932.

  • Alborn,Ñ H.ÑT.,Ñ Turlings,Ñ T.ÑC.ÑJ.,Ñ Jones,Ñ T.ÑH.,Ñ Stenhagen,Ñ G.,Ñ Loughrin,Ñ J.ÑH.,ÑandÑ Tumlinson,Ñ J.ÑH.Ñ1997.ÑAnÑelicitorÑofÑplantÑvolatilesÑfromÑbeetÑarmywormÑoralÑsecretion.ÑScienceÑ276:945–949.

  • Anderson,Ñ B.ÑÅ.Ñ1978.ÑMassÑspectrometryÑofÑfattyÑacidÑpyrrolidides.ÑProg.ÑChem.ÑFatsÑOtherÑLipidsÑ16:279–308.

  • Attygalle,Ñ A.ÑB.,Ñ Jham,Ñ G.ÑN.,Ñ Svatos,Ñ A.,Ñ Frighetto,Ñ R.ÑT.ÑS.,Ñ Meinwald,Ñ J.,Ñ Vilela,Ñ E.ÑF.,Ñ Ferrara,Ñ F.ÑA.,ÑandÑ Uchoafernandes,Ñ M.ÑA.Ñ1995.ÑMicroscale,ÑrandomÑreduction-applicationÑtoÑtheÑcharacterizationÑofÑ(E,Z,Z)-3,8,11-tetradecatrienylÑacetate,ÑaÑnewÑlepidopteranÑsexpheromone.ÑTetrahedronÑLett.Ñ36:5471–5474.

  • Bellas,Ñ T.ÑE.,Ñ Brownlee,Ñ R.ÑG.,ÑandÑ Silverstein,Ñ R.ÑM.Ñ1969.ÑSynthesisÑofÑbrevicomin,ÑprincipalÑsexÑattractantÑinÑtheÑfrassÑofÑtheÑfemaleÑwesternÑpineÑbeetle.ÑTetrahedronÑ25:5149–5153.

  • Beroza,Ñ M.,ÑandÑ Bierl,Ñ B.ÑA.Ñ1966.ÑApparatusÑforÑozonolysisÑofÑmicrogramÑtoÑmilligramÑamountÑofÑcompound.ÑAnal.ÑChem.Ñ38:1976–1977.

  • Beroza,Ñ M.,ÑandÑ Bierl,Ñ B.ÑA.Ñ1967.ÑRapidÑdeterminationÑofÑolefinicÑpositionÑinÑorganicÑcompoundsÑinÑmicrogramÑrangeÑbyÑozonolysisÑandÑgasÑchromatography.ÑAnal.ÑChem.Ñ39:1131–1135.

  • Bestmann,Ñ H.ÑJ.,Ñ Stransky,Ñ W.,ÑandÑ Vostrowsky,Ñ O.Ñ1976.ÑDarstellungÑlithiumsalzfreierÑYlidlosungenÑmitÑNatrium-bis(trimethylsily)amidÑalsÑBase.ÑChem.ÑBer.Ñ109:1694–1700.

  • Bestmann,Ñ H.ÑJ.,Ñ Roth,Ñ K.,Ñ Michaelis,Ñ K.,Ñ Vostrowsky,Ñ O.,Ñ Shafer,Ñ H.ÑJ.,ÑandÑ Michaelis,Ñ R.Ñ1987.ÑSyntheseÑMethylen-unterbrochenerÑLepidopteren-PolyenpheromoneÑundÑStrukturanloger.ÑLiebigsÑAnn.ÑChem.Ñ1987:417–422.

  • Burgstahler,Ñ A.ÑW.,Ñ Weigel,Ñ L.ÑO.,ÑandÑ Schaefer,Ñ C.ÑG.Ñ1976.ÑImprovedÑmodificationÑofÑtheÑRosenmundÑreduction.ÑSynthesisÑ1976:767–768.

  • Brandsma,Ñ L.Ñ1988.ÑPreparativeÑAcetylenicÑChemistry.ÑElsevier,Ñ Amsterdam,Ñp.Ñ225.

  • DeÑMoraes,Ñ C.ÑM.,Ñ Lewis,Ñ W.ÑJ.,Ñ ParĚ,Ñ P.ÑW.,Ñ Alborn,Ñ H.ÑT.,ÑandÑ Tumlinson,Ñ J.ÑH.Ñ1988.ÑHerbivore-infestedÑplantsÑselectivelyÑattractÑparasitoids.ÑNatureÑ393:570–573.

  • Farmer,Ñ E.ÑE.,ÑandÑ Ryan,Ñ C.ÑA.Ñ1992a.ÑOctadecanoid-derivedÑsignalsÑinÑplants.ÑTrendsÑCellÑBiol.Ñ2:236–241.

  • Farmer,Ñ E.ÑE.,ÑandÑ Ryan,Ñ C.ÑA.Ñ1992b.ÑOctadecanoidÑprecursorsÑofÑjasmonicÑacidÑactivateÑtheÑsynthesisÑofÑwound-inducibleÑproteinase-inhibitors.ÑPlantÑCellÑ4:129–134.

  • Gil,Ñ S.,Ñ Lazaro,Ñ M.ÑA.,Ñ Mestres,Ñ R.,ÑandÑ Parra,Ñ M.Ñ1996.ÑSexÑpheromoneÑofÑChiloÑsupressalis:ÑEfficientÑsynthesisÑofÑZ-13-octadenenalÑandÑZ-9-hexadecenal.ÑSynth.ÑCommun.Ñ26:2329–2340.

  • Huang,Ñ W.,Ñ Pulaski,Ñ S.ÑP.,ÑandÑ Meinwald,Ñ J.Ñ1983.ÑSynthesisÑofÑhighlyÑunsaturatedÑinsectÑpheromones:Ñ(Z,Z,Z)-1,3,6,9-HeneicosatetraeneÑandÑ(Z,Z,Z)-1,3,6,9-nonadecatetraene.ÑJ.ÑOrg.ÑChem.Ñ48:2270–2274.

  • Kramell,Ñ R.,Ñ Atzorn,Ñ R.,Ñ Schneider,Ñ G.,Ñ Miersch,Ñ O.,Ñ Bruckner,Ñ C.,Ñ Schmidt,Ñ J.,Ñ Sembdner,Ñ G.,ÑandÑ Parthier,Ñ B.Ñ1995.ÑOccurrenceÑandÑidentificationÑofÑjasmonicÑacidÑandÑitsÑamino-acidÑconjugatesÑinducedÑbyÑosmotic-stressÑinÑbarleyÑleafÑtissue.ÑJ.ÑPlantÑGrowthÑRegul.Ñ14:29–36.

  • Krumm,Ñ T.,Ñ Bandemer,Ñ K.,ÑandÑ Boland,Ñ W.Ñ1995.ÑInductionÑofÑvolatileÑbiosynthesisÑinÑtheÑLimaÑbeanÑ(PhaseolusÑlunatus)ÑbyÑleucineÑandÑisoleucineÑconjugatesÑofÑ1-oxo-ÑandÑ1-hydroxyindan-4-carboxylicÑacid:ÑEvidenceÑforÑaminoÑacidÑconjugatesÑofÑjasmonicÑacidÑasÑintermediatesÑinÑtheÑoctadecanoidÑsignallingÑpathway.ÑFEBSÑLett.Ñ377:523–529.

  • Lammert,Ñ S.ÑR.,Ñ Ellis,Ñ A.ÑI.,Ñ Chauvette,Ñ R.ÑR.,ÑandÑKukolja,Ñ S.Ñ1978.ÑAzetidinoneÑantibiotics.Ñ19.ÑAÑsimpleÑmethodÑforÑtheÑremovalÑofÑp-nitrobenzylÑacidÑprotectiveÑgroup.ÑJ.ÑOrg.ÑChem.Ñ43:1243–1244.

  • McAuslane,Ñ H.ÑJ.,ÑandÑ Alborn,Ñ H.ÑT.Ñ1998.ÑSystemicÑinductionÑofÑallelochemicalsÑinÑglandedÑandÑglandlessÑisogenicÑcottonÑbyÑSpodopteraÑexiguaÑfeeding.ÑJ.ÑChem.ÑEcol.Ñ24:399–416.

  • McAuslane,Ñ H.ÑJ.,Ñ Alborn,Ñ H.ÑT.,ÑandÑ Toth,Ñ J.ÑP.Ñ1997.ÑSystemicÑinductionÑofÑterpenoidÑaldehydesÑinÑcottonÑpigmentÑglandsÑbyÑfeedingÑofÑlarvalÑSpodopteraÑexigua.ÑJ.ÑChem.ÑEcol.Ñ23:2861–2879.

  • Mee,Ñ J.ÑM.ÑL.,Ñ Korth,Ñ J.,ÑandÑ Halpern,Ñ B.Ñ1977.ÑRapidÑandÑquantitativeÑbloodÑaminoÑacidÑanalysisÑbyÑchemicalÑionizationÑmassÑspectrometry.ÑBiomed.ÑMassÑSpectrom.Ñ4:178–181.

  • Millar,Ñ J.ÑG.,ÑandÑ Oehlschlager,Ñ A.ÑC.Ñ1984.ÑSynthesisÑofÑZ,Z,Z-skippedÑdieneÑmacrolideÑpheromonesÑforÑCryptolestesÑandÑOryzaephilusÑgrainÑbeetles.ÑJ.ÑOrg.ÑChem.Ñ49:2332–2338.

  • NISTÑ(NationalÑInstituteÑofÑStandardsÑandÑTechnology).Ñ1995.ÑMassÑspectralÑlibraryÑonÑCD-rom,ÑversionÑ1.0,ÑGaithersburg,ÑMD.

  • Oehlslager,Ñ A.ÑC.,Ñ Czyzewska,Ñ E.,Ñ Aksela,Ñ R.,ÑandÑPierce,Ñ H.ÑD.Ñ1986.ÑImprovedÑsynthesisÑofÑhydroxyÑacidÑprecursorsÑofÑmacrolideÑpheromonesÑofÑcucujidÑgrainÑbeetles.ÑCan.ÑJ.ÑChem.Ñ64:1407–1413.

  • ParĚ,Ñ P.ÑW.,ÑandÑTumlinson,Ñ J.ÑH.Ñ1997.ÑInducedÑsynthesisÑofÑplantÑvolatiles.ÑNatureÑ385:30–31.

  • ParĚ,Ñ P.ÑW.,ÑandÑ Tumlinson,Ñ J.ÑH.Ñ1998.ÑCottonÑvolatilesÑsynthesizedÑandÑreleasedÑdistalÑtoÑtheÑsiteÑofÑinsectÑdamage.ÑPhytochemistryÑ47:521–526.

  • ParĚ,Ñ P.ÑW.,Ñ Alborn,Ñ H.ÑT.,ÑandÑ Tumlinson,Ñ J.ÑH.Ñ1998.ÑConcertedÑbiosynthesisÑofÑanÑinsectÑelicitorÑofÑplantÑvolatiles.ÑProc.ÑNatl.ÑAcad.ÑSci.ÑU.S.A.Ñ95:13971–13975.

  • Pennington,Ñ F.ÑC.,Ñ Clemer,Ñ W.ÑD.,Ñ McLamore,Ñ W.ÑM.,ÑBogert,Ñ V.ÑV.,ÑandÑ Solomons,Ñ I.ÑA.Ñ1953.ÑMicrobiologicallyÑactiveÑ4-thiazolidones.ÑJ.ÑAm.ÑChem.ÑSoc.Ñ75:109–115.

  • RÖse,Ñ U.ÑS.ÑR.,Ñ Manukian,Ñ A.,Ñ Heath,Ñ R.ÑR.,ÑandÑ Tumlinson,Ñ J.ÑH.Ñ1996.ÑVolatileÑsemiochemicalsÑreleasedÑfromÑundamagedÑcottonÑleaves-aÑsystemicÑresponseÑofÑlivingÑplantsÑtoÑcaterpillarÑdamage.ÑPlantÑPhysiol.Ñ111:487–495.

  • Sheehan,Ñ J.ÑC.,Ñ Preston,Ñ J.,ÑandÑ Cruickshank,Ñ P.ÑA.Ñ1965.ÑAÑrapidÑsynthesisÑofÑoligopeptideÑderivativesÑwithoutÑisolationÑofÑintermediates.ÑJ.ÑAm.ÑChem.ÑSoc.Ñ87:2492–2493.

  • Stanley-Samuelson,Ñ D.ÑW.Ñ1994a.ÑAsessingÑtheÑsignificanceÑofÑprostaglandinsÑandÑotherÑeicosanoidsÑinÑinsectÑphysiology.ÑJ.ÑInsectÑPhysiol.Ñ40:3–11.

  • Stanley-Samuelson,Ñ D.ÑW.Ñ1994b.ÑProstaglandinesÑandÑrelatedÑeicosanoidsÑinÑinsects.ÑAdv.ÑInsectÑPhysiol.Ñ24:115–212.

  • Turlings,Ñ T.ÑC.ÑJ.,ÑandÑ Tumlinson,Ñ J.ÑH.Ñ1992.ÑSystemicÑreleaseÑofÑchemicalÑsignalsÑbyÑherbivoreinjuredÑcorn.ÑProc.ÑNatl.ÑAcad.ÑSci.ÑU.S.A.Ñ89:8399–8402.

  • Turlings,Ñ T.ÑC.ÑJ.,Ñ Tumlinson,Ñ J.ÑH.,ÑandÑ Lewis,Ñ W.ÑJ.Ñ1990.ÑExploitationÑofÑherbivore-inducedÑplantÑodorsÑbyÑhostÑseekingÑparasiticÑwasps.ÑScienceÑ250:1251–1253.

  • Turlings,Ñ T.ÑC.ÑJ.,Ñ Tumlinson,Ñ J.ÑH.,Ñ Heath,Ñ R.ÑR.,ÑProveaux,Ñ A.ÑT.,ÑandÑ Doolittle,Ñ R.ÑE.Ñ1991.ÑIsolationÑandÑidentificationÑofÑallelochemicalsÑthatÑattractÑtheÑlarvalÑparasitoidÑCotesiaÑmarginiventrisÑtoÑtheÑmicroÑhabitatÑofÑoneÑofÑitsÑhosts.ÑJ.ÑChem.ÑEcol.Ñ17:2235–2251.

  • Turlings,Ñ T.ÑC.ÑJ.,Ñ McCall,Ñ P.ÑJ.,Ñ Alborn,Ñ H.ÑT.,ÑandÑTumlinson,Ñ J.ÑH.Ñ1993.ÑAnÑelicitorÑinÑcaterpillarÑoralÑsecretionsÑthatÑinducesÑcornÑseedlingsÑtoÑemitÑchemicalÑsignalsÑattractiveÑtoÑparasiticÑwasps.ÑJ.ÑChem.ÑEcol.Ñ19:411–425.

  • Turlings,Ñ T.ÑC.ÑJ.,Ñ Alborn,Ñ H.ÑT.,Ñ Loughrin,Ñ J.ÑH.,ÑandÑTumlinson,Ñ J.ÑH.Ñ2000.ÑVolicitin,ÑanÑelicitorÑofÑmaizeÑvolatilesÑinÑtheÑoralÑsecretionÑofÑSpodopteraÑexigua:ÑItsÑisolationÑandÑbioactivity.ÑJ.ÑChem.ÑEcol.Ñ26:189–202.

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Authors and Affiliations

  1. Center for Medical, Agricultural, and Veterinary Entomology, United States Department of Agriculture, Agricultural Research Service, Gainesville, Florida, 32608

    H. T. Alborn & J. H. Tumlinson

  2. Department of Chemistry, Virginia Military Institute, Lexington, Virginia, 24450

    T. H. Jones

  3. Department of Organic Chemistry, Chalmers University of Technology, S-412 96, Göteborg, Sweden

    G. S. Stenhagen

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  1. H. T. Alborn
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  2. T. H. Jones
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  3. G. S. Stenhagen
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  4. J. H. Tumlinson
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Alborn, H.T., Jones, T.H., Stenhagen, G.S. et al. Identification and Synthesis of Volicitin and Related Components from Beet Armyworm Oral Secretions. J Chem Ecol 26, 203–220 (2000). https://doi.org/10.1023/A:1005401814122

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