{"status":"ok","message-type":"work","message-version":"1.0.0","message":{"indexed":{"date-parts":[[2026,9,29]],"date-time":"2026-09-29T02:10:05Z","timestamp":1790647805858,"version":"4.1.0"},"reference-count":235,"publisher":"MDPI AG","issue":"2","license":[{"start":{"date-parts":[[2018,5,3]],"date-time":"2018-05-03T00:00:00Z","timestamp":1525305600000},"content-version":"vor","delay-in-days":0,"URL":"https:\/\/creativecommons.org\/licenses\/by\/4.0\/"}],"funder":[{"name":"Danish Council for Independant Research","award":["DFF-1323-00088"],"award-info":[{"award-number":["DFF-1323-00088"]}]},{"DOI":"10.13039\/100008398","name":"Villum Foundation","doi-asserted-by":"publisher","award":["Center for Plant Plasticity"],"award-info":[{"award-number":["Center for Plant Plasticity"]}],"id":[{"id":"10.13039\/100008398","id-type":"DOI","asserted-by":"publisher"}]}],"content-domain":{"domain":[],"crossmark-restriction":false},"short-container-title":["Insects"],"abstract":"<jats:p>Chemical defences are key components in insect\u2013plant interactions, as insects continuously learn to overcome plant defence systems by, e.g., detoxification, excretion or sequestration. Cyanogenic glucosides are natural products widespread in the plant kingdom, and also known to be present in arthropods. They are stabilised by a glucoside linkage, which is hydrolysed by the action of \u03b2-glucosidase enzymes, resulting in the release of toxic hydrogen cyanide and deterrent aldehydes or ketones. Such a binary system of components that are chemically inert when spatially separated provides an immediate defence against predators that cause tissue damage. Further roles in nitrogen metabolism and inter- and intraspecific communication has also been suggested for cyanogenic glucosides. In arthropods, cyanogenic glucosides are found in millipedes, centipedes, mites, beetles and bugs, and particularly within butterflies and moths. Cyanogenic glucosides may be even more widespread since many arthropod taxa have not yet been analysed for the presence of this class of natural products. In many instances, arthropods sequester cyanogenic glucosides or their precursors from food plants, thereby avoiding the demand for de novo biosynthesis and minimising the energy spent for defence. Nevertheless, several species of butterflies, moths and millipedes have been shown to biosynthesise cyanogenic glucosides de novo, and even more species have been hypothesised to do so. As for higher plant species, the specific steps in the pathway is catalysed by three enzymes, two cytochromes P450, a glycosyl transferase, and a general P450 oxidoreductase providing electrons to the P450s. The pathway for biosynthesis of cyanogenic glucosides in arthropods has most likely been assembled by recruitment of enzymes, which could most easily be adapted to acquire the required catalytic properties for manufacturing these compounds. The scattered phylogenetic distribution of cyanogenic glucosides in arthropods indicates that the ability to biosynthesise this class of natural products has evolved independently several times. This is corroborated by the characterised enzymes from the pathway in moths and millipedes. Since the biosynthetic pathway is hypothesised to have evolved convergently in plants as well, this would suggest that there is only one universal series of unique intermediates by which amino acids are efficiently converted into CNglcs in different Kingdoms of Life. For arthropods to handle ingestion of cyanogenic glucosides, an effective detoxification system is required. In butterflies and moths, hydrogen cyanide released from hydrolysis of cyanogenic glucosides is mainly detoxified by \u03b2-cyanoalanine synthase, while other arthropods use the enzyme rhodanese. The storage of cyanogenic glucosides and spatially separated hydrolytic enzymes (\u03b2-glucosidases and \u03b1-hydroxynitrile lyases) are important for an effective hydrogen cyanide release for defensive purposes. Accordingly, such hydrolytic enzymes are also present in many cyanogenic arthropods, and spatial separation has been shown in a few species. Although much knowledge regarding presence, biosynthesis, hydrolysis and detoxification of cyanogenic glucosides in arthropods has emerged in recent years, many exciting unanswered questions remain regarding the distribution, roles apart from defence, and convergent evolution of the metabolic pathways involved.<\/jats:p>","DOI":"10.3390\/insects9020051","type":"journal-article","created":{"date-parts":[[2018,5,4]],"date-time":"2018-05-04T03:08:21Z","timestamp":1525403301000},"page":"51","update-policy":"https:\/\/doi.org\/10.3390\/mdpi_crossmark_policy","source":"Crossref","is-referenced-by-count":55,"title":["Cyanogenesis in Arthropods: From Chemical Warfare to Nuptial Gifts"],"prefix":"10.3390","volume":"9","author":[{"ORCID":"https:\/\/orcid.org\/0000-0001-5574-2894","authenticated-orcid":false,"given":"Mika","family":"Zagrobelny","sequence":"first","affiliation":[{"name":"Plant Biochemistry Laboratory, Department of Plant and Environmental Sciences, University of Copenhagen, 1871 Frederiksberg C, Denmark"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"\u00c9rika Cristina Pinheiro","family":"De Castro","sequence":"additional","affiliation":[{"name":"Department of Ecology, Federal University of Rio Grande do Norte, Natal-RN, 59078-900, Brazil"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"ORCID":"https:\/\/orcid.org\/0000-0002-3252-3119","authenticated-orcid":false,"given":"Birger Lindberg","family":"M\u00f8ller","sequence":"additional","affiliation":[{"name":"Plant Biochemistry Laboratory, Department of Plant and Environmental Sciences, University of Copenhagen, 1871 Frederiksberg C, Denmark"},{"name":"VILLUM Center for Plant Plasticity, University of Copenhagen, 1871 Frederiksberg C, Denmark"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"ORCID":"https:\/\/orcid.org\/0000-0003-4100-115X","authenticated-orcid":false,"given":"S\u00f8ren","family":"Bak","sequence":"additional","affiliation":[{"name":"Plant Biochemistry Laboratory, Department of Plant and Environmental Sciences, University of Copenhagen, 1871 Frederiksberg C, Denmark"}],"role":[{"vocabulary":"crossref","role":"author"}]}],"member":"1968","published-online":{"date-parts":[[2018,5,3]]},"reference":[{"key":"ref_1","doi-asserted-by":"crossref","first-page":"10242","DOI":"10.3390\/ijms140510242","article-title":"Plant Defense against Insect Herbivores","volume":"14","author":"Zagrobelny","year":"2013","journal-title":"Int. J. Mol. Sci."},{"key":"ref_2","doi-asserted-by":"crossref","first-page":"531","DOI":"10.1111\/brv.12066","article-title":"How insects overcome two-component plant chemical defence: Plant \u03b2-glucosidases as the main target for herbivore adaptation","volume":"89","author":"Pentzold","year":"2014","journal-title":"Biol. Rev."},{"key":"ref_3","doi-asserted-by":"crossref","first-page":"57","DOI":"10.1146\/annurev.ento.47.091201.145121","article-title":"Sequestration of defensive substances from plants by Lepidoptera","volume":"47","author":"Nishida","year":"2002","journal-title":"Annu. Rev. Entomol."},{"key":"ref_4","doi-asserted-by":"crossref","first-page":"1585","DOI":"10.1016\/j.phytochem.2011.02.023","article-title":"Cyanogenic glucosides in the biological warfare between plants and insects: The Burnet moth-Birdsfoot trefoil model system","volume":"72","author":"Zagrobelny","year":"2011","journal-title":"Phytochemistry"},{"key":"ref_5","doi-asserted-by":"crossref","first-page":"309","DOI":"10.1007\/s11101-006-9033-1","article-title":"Cyanogenic glycosides: A case study for evolution and application of cytochromes P450","volume":"5","author":"Bak","year":"2006","journal-title":"Phytochem. Rev."},{"key":"ref_6","unstructured":"Singh, B.K. (1999). Biosynthesis of cyanogenic glucosides, cyanolipids and related compounds. Plant Amino Acids, Marcel Dekker."},{"key":"ref_7","doi-asserted-by":"crossref","first-page":"433","DOI":"10.1146\/annurev.pp.31.060180.002245","article-title":"Cyanogenic compounds","volume":"31","author":"Conn","year":"1980","journal-title":"Annu. Rev. Plant Physiol."},{"key":"ref_8","doi-asserted-by":"crossref","first-page":"401","DOI":"10.1104\/pp.94.2.401","article-title":"Cyanogenesis in plants","volume":"94","author":"Poulton","year":"1990","journal-title":"Plant Physiol"},{"key":"ref_9","doi-asserted-by":"crossref","first-page":"430","DOI":"10.1093\/glycob\/cww012","article-title":"Apiose: One of nature\u2019s witty games","volume":"26","author":"Picmanova","year":"2016","journal-title":"Glycobiology"},{"key":"ref_10","unstructured":"Vennesland, B., Conn, E.E., Knowles, C.J., Westley, J., and Wissing, F (1981). Cyanide and Arthropods. Cyanide in Biology, Academic Press."},{"key":"ref_11","doi-asserted-by":"crossref","first-page":"78","DOI":"10.1016\/j.bse.2015.04.033","article-title":"The chemical defenses of millipedes (Diplopoda): Biochemistry, physiology and ecology","volume":"61","author":"Shear","year":"2015","journal-title":"Biochem. Syst. Ecol."},{"key":"ref_12","first-page":"131","article-title":"Cyanogenesis and the role of cyanogenic compounds in insects","volume":"140","author":"Nahrstedt","year":"1988","journal-title":"Ciba Found. Symp."},{"key":"ref_13","doi-asserted-by":"crossref","first-page":"1457","DOI":"10.1016\/j.phytochem.2008.02.019","article-title":"Cyanogenesis in plants and arthropods","volume":"69","author":"Zagrobelny","year":"2008","journal-title":"Phytochemistry"},{"key":"ref_14","doi-asserted-by":"crossref","first-page":"1947","DOI":"10.1016\/j.phytochem.2008.04.018","article-title":"Hydroxynitrile Glucosides","volume":"69","author":"Bjarnholt","year":"2008","journal-title":"Phytochemistry"},{"key":"ref_15","unstructured":"Ikan, R. (1999). Cyanogenic glucosides. Naturally Occuring Glycosides, John Wiley & Sons Ltd."},{"key":"ref_16","doi-asserted-by":"crossref","first-page":"1301","DOI":"10.1023\/A:1016298100201","article-title":"Constraints on effectivenes of cyanogenic glycosides in herbivore defense","volume":"28","author":"Gleadow","year":"2002","journal-title":"J. Chem. Ecol."},{"key":"ref_17","doi-asserted-by":"crossref","first-page":"101","DOI":"10.1093\/toxsci\/kfm254","article-title":"Interaction of cyanide and nitric oxide with cytochrome c oxidase: Implications for acute cyanide toxicity","volume":"101","author":"Leavesley","year":"2008","journal-title":"Toxicol. Sci."},{"key":"ref_18","doi-asserted-by":"crossref","first-page":"375","DOI":"10.1042\/BJ20150390","article-title":"A recycling pathway for cyanogenic glycosides evidenced by the comparative metabolic profiling in three cyanogenic plant species","volume":"469","author":"Picmanova","year":"2015","journal-title":"Biochem. J."},{"key":"ref_19","doi-asserted-by":"crossref","unstructured":"Nielsen, L.J., Stuart, P., Picmanova, M., Rasmussen, S., Olsen, C.E., Harholt, J., M\u00f8ller, B.L., and Bjarnholt, N. (2016). Dhurrin metabolism in the developing grain of Sorghum bicolor (L.) Moench investigated by metabolite profiling and novel clustering analyses of time-resolved transcriptomic data. BMC Genom., 17.","DOI":"10.1186\/s12864-016-3360-4"},{"key":"ref_20","first-page":"338","article-title":"Functional diversifications of cyanogenic glucosides","volume":"13","year":"2010","journal-title":"Curr. Opin. Plant Biol."},{"key":"ref_21","doi-asserted-by":"crossref","unstructured":"Bjarnholt, N., Neilson, E.H.J., Crocoll, C., J\u00f8rgensen, K., Motawia, M.S., Olsen, C.E., Dixon, D.P., Edwards, R., and M\u00f8ller, B.L. (2018). Glutathione transferases catalyze recycling of auto-toxic cyanogenic glucosides in sorghum. Plant J., in press.","DOI":"10.1111\/tpj.13923"},{"key":"ref_22","doi-asserted-by":"crossref","first-page":"2057","DOI":"10.1093\/pcp\/pcx135","article-title":"Metabolomic and biochemical approaches link salicylic acid biosynthesis to cyanogenesis in peach plants","volume":"58","author":"Cantabella","year":"2017","journal-title":"Plant Cell Physiol."},{"key":"ref_23","doi-asserted-by":"crossref","first-page":"2691","DOI":"10.1038\/s41598-018-20928-7","article-title":"Label-free Raman hyperspectral imaging analysis localizes the cyanogenic glucoside dhurrin to the cytoplasm in sorghum cells","volume":"8","author":"Heraud","year":"2018","journal-title":"Sci. Rep."},{"key":"ref_24","doi-asserted-by":"crossref","first-page":"363","DOI":"10.1104\/pp.105.065904","article-title":"Cassava plants with a depleted cyanogenic glucoside content in leaves and tubers. Distribution of cyanogenic glucosides, their site of synthesis and transport, and blockage of the biosynthesis by RNA interference technology","volume":"139","author":"Bak","year":"2005","journal-title":"Plant Physiol."},{"key":"ref_25","doi-asserted-by":"crossref","first-page":"617","DOI":"10.1104\/pp.67.4.617","article-title":"Subcellular localization of dhurrin \u03b2-glucosidase and hydroxynitrile lyase in the mesophyll cells of sorghum leaf blades","volume":"67","author":"Thayer","year":"1981","journal-title":"Plant Physiol."},{"key":"ref_26","unstructured":"Romeo, S.B. (1996). Relationships between the defense systems of plants and insects. Recent Advances in Phytochemistry, Pleanum Press."},{"key":"ref_27","doi-asserted-by":"crossref","first-page":"11","DOI":"10.1016\/S0041-0101(99)00128-2","article-title":"Plant cyanogenic glycosides","volume":"38","author":"Vetter","year":"2000","journal-title":"Toxicon"},{"key":"ref_28","doi-asserted-by":"crossref","first-page":"170262","DOI":"10.1098\/rsos.170262","article-title":"Spatial separation of the cyanogenic \u03b2-glucosidase ZfBGD2 and cyanogenic glucosides in the haemolymph of Zygaena larvae facilitates cyanide release","volume":"4","author":"Pentzold","year":"2017","journal-title":"R. Soc. Open. Sci."},{"key":"ref_29","doi-asserted-by":"crossref","unstructured":"Jensen, N.B., Zagrobelny, M., Hjern\u00f8, K., Olsen, C.E., Houghton-Larsen, J., Borch, J., M\u00f8ller, B.L., and Bak, S. (2011). Convergent evolution in biosynthesis of cyanogenic defence compounds in plants and insects. Nat. Commun., 2.","DOI":"10.1038\/ncomms1271"},{"key":"ref_30","doi-asserted-by":"crossref","first-page":"273","DOI":"10.1111\/j.1365-313X.2011.04685.x","article-title":"Genomic clustering of cyanogenic glucoside biosynthetic genes aids their identification in Lotus japonicus and suggests the repeated evolution of this chemical defence pathway","volume":"68","author":"Takos","year":"2011","journal-title":"Plant J."},{"key":"ref_31","doi-asserted-by":"crossref","first-page":"9740","DOI":"10.1073\/pnas.91.21.9740","article-title":"Isolation of the heme-thiolate enzyme cytochrome P450Tyr, Which catalyzes the committed step in the biosynthesis of the cyanogenic glucoside dhurrin in Sorghum bicolor (L.) Moench","volume":"91","author":"Sibbesen","year":"1994","journal-title":"Proc. Natl. Acad. Sci. USA"},{"key":"ref_32","doi-asserted-by":"crossref","first-page":"558","DOI":"10.1111\/tpj.13023","article-title":"The bifurcation of the cyanogenic glucoside and glucosinolate biosynthetic pathways","volume":"84","author":"Clausen","year":"2015","journal-title":"Plant J."},{"key":"ref_33","doi-asserted-by":"crossref","first-page":"393","DOI":"10.1023\/A:1005915507497","article-title":"Cloning of three A type cytochromes P450, CYP71E1, CYP98, and CYP99 from Sorghum bicolor (L.) Moench by a PCR approach and identification by expression in Escherichia coli of CYP71E1 as a multifunctional cytochrome P450 in the biosynthesis of the cyanogenic glucoside dhurrin","volume":"36","author":"Bak","year":"1998","journal-title":"Plant Mol. Biol."},{"key":"ref_34","doi-asserted-by":"crossref","first-page":"35483","DOI":"10.1074\/jbc.274.50.35483","article-title":"The UDP-glucose:p-hydroxymandelonitrile-O-glucosyltransferase that catalyzes the last step in synthesis of the cyanogenic glucoside dhurrin in Sorghum bicolor. Isolation, cloning, heterologous expression, and substrate specificity","volume":"274","author":"Jones","year":"1999","journal-title":"J. Biol. Chem."},{"key":"ref_35","doi-asserted-by":"crossref","first-page":"689","DOI":"10.1016\/0020-1790(87)90037-0","article-title":"Biosynthesis of cyanogenic glucosides in butterflies and moths\u2014Effective incorporation of 2-methylpropanenitrile and 2-methylbutanenitrile into linamarin and lotaustralin by Zygaena and Heliconius species (Lepidoptera)","volume":"17","author":"Davis","year":"1987","journal-title":"Insect Biochem."},{"key":"ref_36","doi-asserted-by":"crossref","first-page":"532","DOI":"10.1111\/imb.12042","article-title":"Cytochrome P450-encoding genes from the Heliconius genome as candidates for cyanogenesis","volume":"22","author":"Chauhan","year":"2013","journal-title":"Insect Mol. Biol."},{"key":"ref_37","doi-asserted-by":"crossref","unstructured":"Zagrobelny, M., Jensen, M.K., Vogel, H., Feyereisen, R., and Bak, S. (2018). Evolution of the biosynthetic pathway for cyanogenic glucosides in Lepidoptera. Mol. Phylogenet Evol., submitted manuscript.","DOI":"10.1007\/s00239-018-9854-8"},{"key":"ref_38","doi-asserted-by":"crossref","first-page":"335","DOI":"10.1002\/2211-5463.12170","article-title":"A novel cytochrome P450, CYP3201B1, is involved in (R)-mandelonitrile biosynthesis in a cyanogenic millipede","volume":"7","author":"Yamaguchi","year":"2017","journal-title":"FEBS Open Bio"},{"key":"ref_39","unstructured":"Romeo, J.T., Ibrahim, R., Varin, L., and De Luca, V. (2000). Function and evolution of plant Cytochrome P450. Recent Advances in Phytochemistry Volume 34, Evolution of Metabolic Pathways, Elsevier Science Publishers."},{"key":"ref_40","doi-asserted-by":"crossref","first-page":"380","DOI":"10.1016\/S1360-1385(00)01720-9","article-title":"Glycosyltransferases in plant natural product synthesis: Characterization of a supergene family","volume":"5","author":"Vogt","year":"2000","journal-title":"Trends Plant Sci."},{"key":"ref_41","doi-asserted-by":"crossref","first-page":"9","DOI":"10.1006\/abbi.1998.1068","article-title":"Substrate specificity of the cytochrome P450 enzymes CYP79A1 and CYP71E1 involved in the biosynthesis of the cyanogenic glucoside dhurrin in Sorghum bicolor (L.) Moench","volume":"363","author":"Kahn","year":"1999","journal-title":"Arch. Biochem. Biophys."},{"key":"ref_42","doi-asserted-by":"crossref","unstructured":"F\u00fcrstenberg-H\u00e4gg, J., Zagrobelny, M., J\u00f8rgensen, K., Vogel, H., M\u00f8ller, B.L., and Bak, S. (2014). Chemical defense balanced by sequestration and de novo biosynthesis in a Lepidopteran specialist. PLoS ONE, 9.","DOI":"10.1371\/journal.pone.0108745"},{"key":"ref_43","doi-asserted-by":"crossref","first-page":"1966","DOI":"10.1074\/jbc.275.3.1966","article-title":"Cytochromes P-450 from Cassava (Manihot esculenta Crantz) catalyzing the first steps in the biosynthesis of the cyanogenic glucosides linamarin and lotaustralin","volume":"275","author":"Andersen","year":"2000","journal-title":"J. Biol. Chem."},{"key":"ref_44","doi-asserted-by":"crossref","first-page":"178","DOI":"10.3891\/acta.chem.scand.48-0178","article-title":"Cyanogenic glucosides in cassava, Manihot esculenta Crantz","volume":"48","author":"Lykkesfeldt","year":"1994","journal-title":"Acta. Chem. Scand."},{"key":"ref_45","doi-asserted-by":"crossref","first-page":"1307","DOI":"10.1016\/S0031-9422(00)85629-0","article-title":"Studies on cassava, Manihot utilissima Pohl-I. Cyanogenesis: The biosynthesis of linamarin and lotaustralin in etiolated seedlings","volume":"7","author":"Nartey","year":"1968","journal-title":"Phytochemistry"},{"key":"ref_46","doi-asserted-by":"crossref","first-page":"71","DOI":"10.1104\/pp.103.038059","article-title":"Biosynthesis of the nitrile glucosides rhodiocyanoside A and D and the cyanogenic glucosides lotaustralin and linamarin in Lotus japonicus","volume":"135","author":"Forslund","year":"2004","journal-title":"Plant Physiol."},{"key":"ref_47","doi-asserted-by":"crossref","first-page":"10","DOI":"10.1016\/j.ibmb.2006.09.008","article-title":"The cyanogenic glucoside composition of Zygaena filipendulae (Lepidoptera: Zygaenidae) as effected by feeding on wild-type and transgenic lotus populations with variable cyanogenic glucoside profiles","volume":"37","author":"Zagrobelny","year":"2007","journal-title":"Insect Biochem. Mol. Biol."},{"key":"ref_48","doi-asserted-by":"crossref","first-page":"65","DOI":"10.1016\/0305-0491(83)90041-X","article-title":"Occurrence, variation and biosynthesis of the cyanogenic glucosides linamarin and lotaustralin in species of the Heliconiini (Insecta, Lepidoptera)","volume":"75","author":"Nahrstedt","year":"1983","journal-title":"Comp. Biochem. Physiol. PT B"},{"key":"ref_49","doi-asserted-by":"crossref","first-page":"745","DOI":"10.1016\/0305-0491(85)90519-X","article-title":"Biosynthesis and quantitative relationships of the cyanogenic glucosides, linamarin and lotaustralin, in genera of the Heliconiini (Insecta, Lepidoptera)","volume":"82","author":"Nahrstedt","year":"1985","journal-title":"Comp. Biochem. Physiol. PT B"},{"key":"ref_50","doi-asserted-by":"crossref","first-page":"194","DOI":"10.1111\/j.1365-313X.2011.04529.x","article-title":"A P450-centric view of plant evolution","volume":"66","author":"Nelson","year":"2011","journal-title":"Plant J."},{"key":"ref_51","doi-asserted-by":"crossref","first-page":"95","DOI":"10.1016\/j.molp.2017.12.014","article-title":"Oximes: Unrecognized chameleons in general and specialized plant metabolism","volume":"11","author":"Neilson","year":"2018","journal-title":"Mol. Plant"},{"key":"ref_52","doi-asserted-by":"crossref","first-page":"133","DOI":"10.1016\/j.ibmb.2011.11.006","article-title":"Comparative analysis of the UDP-glycosyltransferase multigene family in insects","volume":"42","author":"Ahn","year":"2012","journal-title":"Insect Biochem. Mol. Biol."},{"key":"ref_53","doi-asserted-by":"crossref","first-page":"66","DOI":"10.1016\/j.ibmb.2014.07.008","article-title":"Biosynthetic pathway of the phytohormone auxin in insects and screening of its inhibitors","volume":"53","author":"Suzuki","year":"2014","journal-title":"Insect Biochem. Mol. Biol."},{"key":"ref_54","first-page":"1","article-title":"Morphologie und histologie der wehrsekretbeh\u00e4lter erwachsener raupen von Zygaena trifolii","volume":"48","author":"Franzl","year":"1984","journal-title":"Entomol. Abh."},{"key":"ref_55","doi-asserted-by":"crossref","first-page":"101","DOI":"10.1105\/tpc.13.1.101","article-title":"CYP83B1, a cytochrome P450 at the metabolic branch point in auxin and indole glucosinolate biosynthesis in Arabidopsis","volume":"13","author":"Bak","year":"2001","journal-title":"Plant Cell"},{"key":"ref_56","doi-asserted-by":"crossref","first-page":"5430","DOI":"10.1073\/pnas.0811226106","article-title":"Biochemical analyses of indole-3-acetaldoxime-dependent auxin biosynthesis in Arabidopsis","volume":"106","author":"Sugawara","year":"2009","journal-title":"Proc. Natl. Acad. Sci. USA"},{"key":"ref_57","doi-asserted-by":"crossref","first-page":"3049","DOI":"10.1016\/S0021-9258(19)85850-7","article-title":"The biosynthesis of cyanogenic glucosides in higher plants. Channeling of intermediates in dhurrin biosynthesis by a microsomal system from Sorghum bicolor (L.) Moench","volume":"255","author":"Conn","year":"1980","journal-title":"J. Biol. Chem."},{"key":"ref_58","doi-asserted-by":"crossref","first-page":"37","DOI":"10.1007\/s40610-017-0053-y","article-title":"Assembly of dynamic P450-mediated metabolons\u2013Order versus chaos","volume":"3","author":"Bassard","year":"2017","journal-title":"Curr. Mol. Biol. Rep."},{"key":"ref_59","doi-asserted-by":"crossref","first-page":"890","DOI":"10.1126\/science.aag2347","article-title":"Characterization of a dynamic metabolon producing the defense compound dhurrin in sorghum","volume":"354","author":"Laursen","year":"2016","journal-title":"Science"},{"key":"ref_60","doi-asserted-by":"crossref","first-page":"280","DOI":"10.1016\/j.pbi.2005.03.014","article-title":"Metabolon formation and metabolic channeling in the biosynthesis of plant natural products","volume":"8","author":"Rasmussen","year":"2005","journal-title":"Curr. Opin. Plant Biol."},{"key":"ref_61","doi-asserted-by":"crossref","first-page":"2","DOI":"10.1034\/j.1600-0749.2002.00056.x","article-title":"Comparative biochemistry of eumelanogenesis and the protective roles of phenoloxidase and melanin in insects","volume":"15","author":"Sugumaran","year":"2002","journal-title":"Pigment Cell Res."},{"key":"ref_62","doi-asserted-by":"crossref","first-page":"956","DOI":"10.1124\/mol.108.052001","article-title":"Interaction of cytochrome P450 3A4 and UDP-glucuronosyltransferase 2B7: Evidence for protein-protein association and possible involvement of CYP3A4 J-helix in the interaction","volume":"75","author":"Takeda","year":"2009","journal-title":"Mol. Pharmacol."},{"key":"ref_63","doi-asserted-by":"crossref","first-page":"140","DOI":"10.3109\/03602530903208579","article-title":"Modulation of UDP-glucuronosyltransferase activity by protein-protein association","volume":"42","author":"Ishii","year":"2010","journal-title":"Drug Metab. Rev."},{"key":"ref_64","unstructured":"Zagrobelny, M., Bak, S., and M\u00f8ller, B.L. (2006, January 26). Cyanogenic glucosides as determinants of feeding preferences in Zygaena filipendulae. Proceedings of the 10th International Symposium on Zygaenidae (Lepidoptera), Lyon, France."},{"key":"ref_65","doi-asserted-by":"crossref","first-page":"1795","DOI":"10.1016\/j.phytochem.2008.03.006","article-title":"\u03b2-Glucosidases as detonators of plant chemical defense","volume":"69","author":"Morant","year":"2008","journal-title":"Phytochemistry"},{"key":"ref_66","doi-asserted-by":"crossref","first-page":"1","DOI":"10.1021\/bk-1993-0533.ch001","article-title":"\u03b2-Glucosidases\u2013Overview","volume":"533","author":"Esen","year":"1993","journal-title":"ACS Symp. Ser."},{"key":"ref_67","doi-asserted-by":"crossref","first-page":"3389","DOI":"10.1007\/s00018-010-0399-2","article-title":"\u03b2-Glucosidases","volume":"67","author":"Esen","year":"2010","journal-title":"Cell Mol. Life Sci."},{"key":"ref_68","first-page":"611","article-title":"Hydroxynitrile lyases of higher plants","volume":"377","author":"Wajant","year":"1996","journal-title":"Biol. Chem."},{"key":"ref_69","doi-asserted-by":"crossref","first-page":"891","DOI":"10.1111\/j.1399-3054.1996.tb06700.x","article-title":"Hydroxynitrile lyases: Functions and properties","volume":"98","author":"Hickel","year":"1996","journal-title":"Physiol. Plant"},{"key":"ref_70","doi-asserted-by":"crossref","first-page":"712","DOI":"10.1007\/BF01974565","article-title":"Purification and characterization of a \u03b2-glucosidase (linamarase) from the haemolymph of Zygaena trifolii Esper, 1783 (Insecta, Lepidoptera)","volume":"45","author":"Franzl","year":"1989","journal-title":"Experientia"},{"key":"ref_71","doi-asserted-by":"crossref","first-page":"611","DOI":"10.1055\/s-2006-961234","article-title":"Purification and characterization of an \u03b1-hydroxynitrile lyase from the haemolymph of the larvae of Zygaena trifolii","volume":"56","author":"Nahrstedt","year":"1990","journal-title":"Planta Med."},{"key":"ref_72","doi-asserted-by":"crossref","first-page":"26998","DOI":"10.1038\/srep26998","article-title":"A sacrificial millipede altruistically protects its swarm using a drone blood enzyme, mandelonitrile oxidase","volume":"6","author":"Ishida","year":"2016","journal-title":"Sci. Rep."},{"key":"ref_73","unstructured":"Vennesland, B., Conn, E.E., Knowles, C.J., Westby, J., and Wissing, F. (1981). Cyanide as a metabolic inhibitor. Cyanide in Biology, Academic."},{"key":"ref_74","doi-asserted-by":"crossref","first-page":"18848","DOI":"10.1073\/pnas.0709315104","article-title":"Evolution of heteromeric nitrilase complexes in Poaceae with new functions in nitrile metabolism","volume":"104","author":"Jenrich","year":"2007","journal-title":"Proc. Natl. Acad. Sci. USA"},{"key":"ref_75","doi-asserted-by":"crossref","first-page":"473","DOI":"10.1104\/pp.88.2.473","article-title":"Cyanide metabolism in relation to ethylene production in plant tissues","volume":"88","author":"Yip","year":"1988","journal-title":"Plant Physiol."},{"key":"ref_76","doi-asserted-by":"crossref","first-page":"1199","DOI":"10.1104\/pp.65.6.1199","article-title":"Metabolism of hydrogen cyanide by higher plants","volume":"65","author":"Miller","year":"1980","journal-title":"Plant Physiol."},{"key":"ref_77","doi-asserted-by":"crossref","first-page":"2758","DOI":"10.1021\/ja01038a058","article-title":"Toxic principle in vetch: Isolation and identification of g-L-glutamyl-L-\u03b2-cyanoalanine from common vetch seeds: Distribution in some legumes","volume":"91","author":"Ressler","year":"1969","journal-title":"J. Am. Chem. Soc."},{"key":"ref_78","doi-asserted-by":"crossref","first-page":"1789","DOI":"10.1007\/BF01013229","article-title":"Cyanogenesis\u2013A general phenomenon in the Lepidoptera","volume":"13","author":"Witthohn","year":"1987","journal-title":"J. Chem. Ecol."},{"key":"ref_79","doi-asserted-by":"crossref","unstructured":"Shields, V.D.C. (2017). Herbivore adaptations to plant cyanide defenses. Herbivores, InTech.","DOI":"10.5772\/62658"},{"key":"ref_80","unstructured":"Kerkut, G.A., and Gilbert, L.I. (1985). Cyanogenesis in insects. Comprehensive Insect Physiology, Biochemistry and Pharmacology, Pleanum Press."},{"key":"ref_81","doi-asserted-by":"crossref","first-page":"e02365","DOI":"10.7554\/eLife.02365","article-title":"A gene horizontally transferred from bacteria protects arthropods from host plant cyanide poisoning","volume":"3","author":"Wybouw","year":"2014","journal-title":"elife"},{"key":"ref_82","doi-asserted-by":"crossref","first-page":"1785","DOI":"10.1093\/gbe\/evw119","article-title":"Horizontal gene transfer contributes to the evolution of Arthropod herbivory","volume":"8","author":"Wybouw","year":"2016","journal-title":"Genome Biol. Evol."},{"key":"ref_83","doi-asserted-by":"crossref","unstructured":"Herfurth, A.M., van Ohlen, M., and Wittstock, U. (2017). \u00df-Cyanoalanine synthases and their possible role in Pierid host plant adaptation. Insects, 8.","DOI":"10.3390\/insects8020062"},{"key":"ref_84","doi-asserted-by":"crossref","first-page":"99","DOI":"10.1016\/j.ibmb.2015.12.004","article-title":"Cyanide detoxification in an insect herbivore: Molecular identification of \u03b2-cyanoalanine synthases from Pieris rapae","volume":"70","author":"Herfurth","year":"2016","journal-title":"Insect Biochem. Mol. Biol."},{"key":"ref_85","first-page":"243","article-title":"Die Rhodanbildung im Tierk\u00f6rper","volume":"259","author":"Lang","year":"1933","journal-title":"Biochem. Z."},{"key":"ref_86","doi-asserted-by":"crossref","first-page":"45","DOI":"10.1007\/BF00987603","article-title":"Rhodanese in insects","volume":"11","author":"Beesley","year":"1985","journal-title":"J. Chem. Ecol."},{"key":"ref_87","doi-asserted-by":"crossref","first-page":"741","DOI":"10.1093\/embo-reports\/kvf150","article-title":"The rhodanese\/Cdc25 phosphatase superfamily\u2013Sequence-structure-function relations","volume":"3","author":"Bordo","year":"2002","journal-title":"Embo Rep."},{"key":"ref_88","doi-asserted-by":"crossref","first-page":"367","DOI":"10.1016\/0020-1790(82)90033-6","article-title":"Is rhodanese important in the detoxification of dietary cyanide in southern armyworm (Spodoptera eridania Cramer) larvae","volume":"12","author":"Long","year":"1982","journal-title":"Insect Biochem."},{"key":"ref_89","doi-asserted-by":"crossref","first-page":"25055","DOI":"10.1074\/jbc.M301978200","article-title":"Mutational and structural analysis of aglycone specificity in maize and sorghum \u03b2-glucosidases","volume":"278","author":"Verdoucq","year":"2003","journal-title":"J. Biol. Chem."},{"key":"ref_90","doi-asserted-by":"crossref","first-page":"25","DOI":"10.1007\/BF00028958","article-title":"Proporties and functions of the cyanogenic system in higher plants","volume":"48","author":"Kakes","year":"1990","journal-title":"Euphytica"},{"key":"ref_91","doi-asserted-by":"crossref","first-page":"1777","DOI":"10.1021\/jf4056659","article-title":"Ultraperformance liquid chromatography tandem mass spectrometry determination of cyanogenic glucosides in trifolium species","volume":"62","author":"Muzashvili","year":"2014","journal-title":"J. Agric. Food. Chem."},{"key":"ref_92","doi-asserted-by":"crossref","first-page":"299","DOI":"10.1111\/tpj.12561","article-title":"The evolutionary appearance of non-cyanogenic hydroxynitrile glucosides in the Lotus genus is accompanied by the substrate specialization of paralogous \u03b2-glucosidases resulting from a crucial amino acid substitution","volume":"79","author":"Lai","year":"2014","journal-title":"Plant J."},{"key":"ref_93","doi-asserted-by":"crossref","first-page":"525","DOI":"10.1007\/s10886-012-0114-x","article-title":"Occurrence of sarmentosin and other hydroxynitrile glucosides in Parnassius (papilionidae) butterflies and their food plants","volume":"38","author":"Bjarnholt","year":"2012","journal-title":"J. Chem. Ecol."},{"key":"ref_94","doi-asserted-by":"crossref","first-page":"155","DOI":"10.1146\/annurev-arplant-050213-040027","article-title":"Cyanogenic glycosides: Synthesis, physiology, and phenotypic plasticity","volume":"65","author":"Gleadow","year":"2014","journal-title":"Annu. Rev. Plant. Biol."},{"key":"ref_95","doi-asserted-by":"crossref","first-page":"1222","DOI":"10.1104\/pp.000687","article-title":"Dhurrin synthesis in sorghum is regulated at the transcriptional level and induced by nitrogen fertilization in older plants","volume":"129","author":"Busk","year":"2002","journal-title":"Plant Physiol."},{"key":"ref_96","doi-asserted-by":"crossref","first-page":"293","DOI":"10.1016\/j.phytochem.2003.10.016","article-title":"Cyanogenic glucosides and plant-insect interactions","volume":"65","author":"Zagrobelny","year":"2004","journal-title":"Phytochemistry"},{"key":"ref_97","doi-asserted-by":"crossref","first-page":"811","DOI":"10.1007\/s00442-014-3036-1","article-title":"Chemical defense lowers plant competitiveness","volume":"176","author":"Ballhorn","year":"2014","journal-title":"Oecologia"},{"key":"ref_98","doi-asserted-by":"crossref","first-page":"20130347","DOI":"10.1098\/rstb.2013.0347","article-title":"Adaptive gains through repeated gene loss: Parallel evolution of cyanogenesis polymorphisms in the genus Trifolium (Fabaceae)","volume":"369","author":"Olsen","year":"2014","journal-title":"Phil. Trans. R. Soc. Lond. B Biol. Sci."},{"key":"ref_99","first-page":"155","article-title":"Plasticity in cyanogenesis of Trifolium repens L.: Inducibility, fitness costs and variable expression","volume":"4","author":"Hayden","year":"2002","journal-title":"Evol. Ecol. Res."},{"key":"ref_100","doi-asserted-by":"crossref","first-page":"724","DOI":"10.1111\/j.1365-294X.2012.05667.x","article-title":"Recurrent gene deletions and the evolution of adaptive cyanogenesis polymorphisms in white clover (Trifolium repens L.)","volume":"22","author":"Olsen","year":"2013","journal-title":"Mol. Ecol."},{"key":"ref_101","doi-asserted-by":"crossref","first-page":"1141","DOI":"10.1086\/591984","article-title":"Freezing tolerance and cyanogenesis in white clover (Trifolium repens L. Fabaceae)","volume":"169","author":"Olsen","year":"2008","journal-title":"Int. J. Plant Sci."},{"key":"ref_102","doi-asserted-by":"crossref","first-page":"2455","DOI":"10.1111\/j.1365-294X.2012.05486.x","article-title":"Rapid evolution of an adaptive cyanogenesis cline in introduced North American white clover (Trifolium repens L.)","volume":"21","author":"Kooyers","year":"2012","journal-title":"Mol. Ecol."},{"key":"ref_103","doi-asserted-by":"crossref","first-page":"160226","DOI":"10.1098\/rsos.160226","article-title":"Differential phenotypic and genetic expression of defence compounds in a plant-herbivore interaction along elevation","volume":"3","author":"Salgado","year":"2016","journal-title":"R. Soc. Open. Sci."},{"key":"ref_104","doi-asserted-by":"crossref","first-page":"1053","DOI":"10.1111\/mec.12666","article-title":"Aridity shapes cyanogenesis cline evolution in white clover (Trifolium repens L.)","volume":"23","author":"Kooyers","year":"2014","journal-title":"Mol. Ecol."},{"key":"ref_105","doi-asserted-by":"crossref","first-page":"357","DOI":"10.1093\/aob\/mcu141","article-title":"Salinity-mediated cyanogenesis in white clover (Trifolium repens) affects trophic interactions","volume":"114","author":"Ballhorn","year":"2014","journal-title":"Ann. Bot."},{"key":"ref_106","doi-asserted-by":"crossref","first-page":"817","DOI":"10.1093\/pcp\/pct054","article-title":"Stress enhances the synthesis of secondary plant products: The impact of stress-related over-reduction on the accumulation of natural products","volume":"54","author":"Selmar","year":"2013","journal-title":"Plant Cell Physiol."},{"key":"ref_107","doi-asserted-by":"crossref","first-page":"1109","DOI":"10.1038\/1931109a0","article-title":"Selective eating of acyanogenic form of plant Lotus corniculatus by various animals","volume":"193","author":"Jones","year":"1962","journal-title":"Nature"},{"key":"ref_108","first-page":"151","article-title":"Cyanogenesis in animal-plant interactions","volume":"140","author":"Jones","year":"1988","journal-title":"Ciba Found. Symp."},{"key":"ref_109","doi-asserted-by":"crossref","first-page":"5685","DOI":"10.1073\/pnas.1016508108","article-title":"Tradeoffs associated with constitutive and induced plant resistance against herbivory","volume":"108","author":"Kempel","year":"2011","journal-title":"Proc. Natl. Acad. Sci. USA"},{"key":"ref_110","doi-asserted-by":"crossref","first-page":"392","DOI":"10.1038\/hdy.1995.57","article-title":"Cyanogenesis in Turnera ulmifolia L. (Turneraceae). I. Phenotypic distribution and genetic variation for cyanogenesis on Jamaica","volume":"74","author":"Schappert","year":"1995","journal-title":"Heredity"},{"key":"ref_111","first-page":"337","article-title":"Cyanogenesis in Turnera ulmifolia L. (Turneraceae): II. Developmental expression, heritability and cost of cyanogenesis","volume":"2","author":"Schappert","year":"2000","journal-title":"Evol. Ecol. Res."},{"key":"ref_112","doi-asserted-by":"crossref","first-page":"1826","DOI":"10.1126\/science.1062249","article-title":"Resistance to an herbivore through engineered cyanogenic glucoside synthesis","volume":"293","author":"Tattersall","year":"2001","journal-title":"Science"},{"key":"ref_113","doi-asserted-by":"crossref","first-page":"119","DOI":"10.1016\/j.ibmb.2015.10.004","article-title":"Metabolism, excretion and avoidance of cyanogenic glucosides in insects with different feeding specialisations","volume":"66","author":"Pentzold","year":"2015","journal-title":"Insect Biochem. Mol. Biol."},{"key":"ref_114","doi-asserted-by":"crossref","first-page":"901","DOI":"10.1007\/BF00990212","article-title":"Hydrogen cyanide-producing glands in a scolopender, Asanada N.SP. (Chilopoda, Scolopendridae)","volume":"5","author":"Maschwitz","year":"1979","journal-title":"J. Chem. Ecol."},{"key":"ref_115","doi-asserted-by":"crossref","first-page":"421","DOI":"10.1007\/BF00988807","article-title":"Benzoyl cyanide and mandelonitrile in the cyanogenic secretion of a Centipede","volume":"2","author":"Jones","year":"1976","journal-title":"J. Chem. Ecol."},{"key":"ref_116","doi-asserted-by":"crossref","first-page":"861","DOI":"10.1007\/s00114-013-1086-6","article-title":"Chemistry of the sternal gland secretion of the Mediterranean centipede Himantarium gabrielis (Linnaeus, 1767) (Chilopoda: Geophilomorpha: Himantariidae)","volume":"100","author":"Vujisic","year":"2013","journal-title":"Naturwissenschaften"},{"key":"ref_117","doi-asserted-by":"crossref","first-page":"15","DOI":"10.1007\/s10886-014-0536-8","article-title":"Chemical polymorphism in defense secretions during ontogenetic development of the millipede Niponia nodulosa","volume":"41","author":"Kuwahara","year":"2015","journal-title":"J. Chem. Ecol."},{"key":"ref_118","doi-asserted-by":"crossref","first-page":"101","DOI":"10.1007\/BF00988137","article-title":"Benzoyl cyanide and mandelonitrile benzoate in defensive secretions of millipedes","volume":"3","author":"Duffey","year":"1977","journal-title":"J. Chem. Ecol."},{"key":"ref_119","first-page":"753","article-title":"Intermediates in biosynthesis of HCN and benzaldehyde by a polydesmid millipede, Harpaphe haydeniana Wood","volume":"47","author":"Duffey","year":"1974","journal-title":"Comp. Biochem. Physiol."},{"key":"ref_120","doi-asserted-by":"crossref","unstructured":"Bettini, S. (1978). Defensive secretions of millipedes. Arthropod Venoms, Springer.","DOI":"10.1007\/978-3-642-45501-8"},{"key":"ref_121","doi-asserted-by":"crossref","first-page":"1047","DOI":"10.1139\/z72-141","article-title":"Defensive secretion: Biosynthesis of hydrogen-cyanide and benzaldehyde from phenylalanine by a millipede","volume":"50","author":"Towers","year":"1972","journal-title":"Can. J. Zool."},{"key":"ref_122","doi-asserted-by":"crossref","first-page":"447","DOI":"10.1303\/aez.32.447","article-title":"Identification of Nedyopus patriocus patriocus (Attems, 1898) (Polydesmida: Paradoxosomatidae) secretions as possible defense substances","volume":"32","author":"Noguchi","year":"1997","journal-title":"Appl. Ent. Zool."},{"key":"ref_123","doi-asserted-by":"crossref","first-page":"401","DOI":"10.1303\/aez.2003.401","article-title":"Identification of secretory compounds from the millipede, Oxidus gracilis C.L. Koch (Polydesmida: Paradoxosomatidae) and their variation in different habitats","volume":"38","author":"Taira","year":"2003","journal-title":"Appl. Ent. Zool."},{"key":"ref_124","doi-asserted-by":"crossref","first-page":"235","DOI":"10.1093\/aesa\/66.1.235","article-title":"Phenol and benzaldehyde in the defensive secretion of a strongylosomid millipede","volume":"66","author":"Blum","year":"1973","journal-title":"Ann. Entomol. Soc. Am."},{"key":"ref_125","doi-asserted-by":"crossref","first-page":"1063","DOI":"10.1007\/s10886-014-0509-y","article-title":"Glucosinolate-related glucosides in Alliaria petiolata: Sources of variation in the plant and different metabolism in an adapted specialist herbivore, Pieris rapae","volume":"40","author":"Frisch","year":"2014","journal-title":"J. Chem. Ecol."},{"key":"ref_126","doi-asserted-by":"crossref","first-page":"31","DOI":"10.1111\/j.1469-7998.1983.tb06115.x","article-title":"Studies on an Indian polydesmoid millipede Streptogonopus phipsoni: Life cycle and swarming behaviour of the larvae","volume":"199","author":"Bellairs","year":"1983","journal-title":"J. Zool. Lond."},{"key":"ref_127","doi-asserted-by":"crossref","first-page":"95","DOI":"10.5038\/1827-806X.41.1.10","article-title":"Chemical defense in the cave-dwelling millipede Brachydesmus troglobius Daday, 1889 (Diplopoda, Polydesmidae)","volume":"41","author":"Makarov","year":"2012","journal-title":"Int. J. Speleol."},{"key":"ref_128","doi-asserted-by":"crossref","first-page":"978","DOI":"10.1007\/s10886-010-9847-6","article-title":"Defensive secretions in three species of polydesmids (Diplopoda, Polydesmida, Polydesmidae)","volume":"36","author":"Makarov","year":"2010","journal-title":"J. Chem. Ecol."},{"key":"ref_129","doi-asserted-by":"crossref","first-page":"517","DOI":"10.1303\/aez.29.517","article-title":"Identification of benzaldehyde, phenol and mandelonitrile from Epanerchodus japonicus Carl (Polydesmide: Polydesmidae) as possible defence substances","volume":"29","author":"Mori","year":"1994","journal-title":"Appl. Ent. Zool."},{"key":"ref_130","first-page":"387","article-title":"Defensive secretions from the repugnatorial glands of a polydesmoid millipede","volume":"47","author":"Bano","year":"1978","journal-title":"Curr. Sci."},{"key":"ref_131","doi-asserted-by":"crossref","first-page":"206","DOI":"10.1007\/BF02124069","article-title":"Benzoyl cyanide in the defensive secretion of polydesmoid millipeds","volume":"33","author":"Conner","year":"1977","journal-title":"Experientia"},{"key":"ref_132","doi-asserted-by":"crossref","first-page":"10605","DOI":"10.1073\/pnas.1508311112","article-title":"Discovery and molecular and biocatalytic properties of hydroxynitrile lyase from an invasive millipede, Chamberlinius hualienensis","volume":"112","author":"Dadashipour","year":"2015","journal-title":"Proc. Natl. Acad. Sci. USA"},{"key":"ref_133","doi-asserted-by":"crossref","first-page":"197","DOI":"10.1303\/aez.30.197","article-title":"Major defensive cyanogen from Parafontaria laminata armigera Verhoeff (Xystodesmidae: Polydesmida)","volume":"30","author":"Mori","year":"1995","journal-title":"Appl. Ent. Zool."},{"key":"ref_134","doi-asserted-by":"crossref","first-page":"73","DOI":"10.1303\/aez.2002.73","article-title":"Species-specific chemical compositions of defense secretions from Parafontaria tonominea Attems and Riukiaria semicircularis semicircularis Takakuwa (Polydesmida: Xystodesmidae)","volume":"37","author":"Omura","year":"2002","journal-title":"Appl. Ent. Zool."},{"key":"ref_135","first-page":"105","article-title":"Note on the poison produced by the Polydesmus (Fontaria) vicinus","volume":"9","author":"Pallares","year":"1946","journal-title":"Linn. Arch. Biochem. Biophys."},{"key":"ref_136","first-page":"91","article-title":"Studies on the constituents of smells from some Okinawan local millipedes","volume":"56","author":"Kikunaga","year":"1993","journal-title":"Bull. Coll. Sci. Univ. Ryukyus"},{"key":"ref_137","doi-asserted-by":"crossref","first-page":"3469","DOI":"10.1073\/pnas.1618327114","article-title":"Storage and release of hydrogen cyanide in a chelicerate (Oribatula tibialis)","volume":"114","author":"Raspotnig","year":"2017","journal-title":"Proc. Natl. Acad. Sci. USA"},{"key":"ref_138","doi-asserted-by":"crossref","first-page":"1552","DOI":"10.1007\/s10886-012-0220-9","article-title":"Quantification of canavanine, 2-aminoethanol, and cyanamide in Aphis craccivora and its host plants, Robinia pseudoacacia and Vicia angustifolia: Effects of these compounds on larval survivorship of Harmonia axyridis","volume":"38","author":"Kamo","year":"2012","journal-title":"J. Chem. Ecol."},{"key":"ref_139","doi-asserted-by":"crossref","first-page":"199","DOI":"10.1007\/BF01021279","article-title":"Sapindaceae, cyanolipids, and bugs","volume":"16","author":"Aldrich","year":"1990","journal-title":"J. Chem. Ecol."},{"key":"ref_140","doi-asserted-by":"crossref","first-page":"355","DOI":"10.1016\/0305-1978(82)90010-2","article-title":"Cyanogenic and other glucosides in a Neo-Guinean bug Leptocoris isolata: Possible precursors in its host-plant","volume":"10","author":"Braekman","year":"1982","journal-title":"Biochem. Syst. Ecol."},{"key":"ref_141","doi-asserted-by":"crossref","first-page":"928","DOI":"10.1515\/znc-1986-9-1020","article-title":"(R) Mandelonitrile and prunasin, the sources of hydrogen cyanide in all stages of Paropsis atomaria (Coleoptera: Chrysomelidae)","volume":"41","author":"Nahrstedt","year":"1986","journal-title":"Z. Naturforsch. C"},{"key":"ref_142","doi-asserted-by":"crossref","first-page":"1793","DOI":"10.1139\/o61-200","article-title":"The action of fumigants on insects. III. The fate of hydrogen cyanide in Sitophilus granarius (L.)","volume":"39","author":"Bond","year":"1961","journal-title":"Can. J. Biochem. Physiol."},{"key":"ref_143","doi-asserted-by":"crossref","first-page":"37","DOI":"10.1016\/S0031-9422(00)97007-9","article-title":"A cyanoglucoside, sarmentosin, from the magpie moth, Abraxas grossulariata, Geometridae: Lepidoptera","volume":"36","author":"Nishida","year":"1994","journal-title":"Phytochemistry"},{"key":"ref_144","doi-asserted-by":"crossref","first-page":"1268","DOI":"10.2307\/1939211","article-title":"Defensive regurgitation of allelochemicals derived from host cyanogenesis by Eastern tent caterpillars","volume":"68","author":"Peterson","year":"1987","journal-title":"Ecology"},{"key":"ref_145","doi-asserted-by":"crossref","first-page":"306","DOI":"10.1007\/s001140100238","article-title":"Production of a cyanogenic secretion by a thyridid caterpillar (Calindoea trifascialis, Thyrididae, Lepidoptera)","volume":"88","author":"Darling","year":"2001","journal-title":"Naturwissenschaften"},{"key":"ref_146","doi-asserted-by":"crossref","first-page":"1853","DOI":"10.1016\/S0031-9422(00)81161-9","article-title":"Cycasin in the endangered butterfly Eumaeus atala Florida","volume":"25","author":"Rothschild","year":"1986","journal-title":"Phytochemistry"},{"key":"ref_147","doi-asserted-by":"crossref","first-page":"575","DOI":"10.1016\/0305-0491(81)90077-8","article-title":"The occurrence of the cyanoglucosides, linamarin and lotaustralin, in Acraea and Heliconius butterflies","volume":"68","author":"Nahrstedt","year":"1981","journal-title":"Comp. Biochem. Physiol. PT B"},{"key":"ref_148","doi-asserted-by":"crossref","first-page":"52","DOI":"10.1007\/BF01325228","article-title":"Evolutionary strategies of chemical defense in aposematic butterflies: Cyanogenesis in Asteraceae-feeding American Acreinae","volume":"1","author":"Brown","year":"1990","journal-title":"Chemoecol."},{"key":"ref_149","doi-asserted-by":"crossref","first-page":"555","DOI":"10.1111\/brv.12357","article-title":"The arms race between heliconiine butterflies and Passiflora plants\u2014New insights on an ancient subject","volume":"93","author":"Zagrobelny","year":"2018","journal-title":"Biol. Rev."},{"key":"ref_150","unstructured":"De Castro, \u00c9.C.P., Zagrobelny, M., Cardoso, M.Z., Zurano, J.P., Feyereisen, R., and Bak, S. (2018). The paradox between sequestration and biosynthesis of cyanogenic glucosides in heliconiine butterflies and its consequences for diversification of Passiflora plants. Evolution, submitted manuscript."},{"key":"ref_151","doi-asserted-by":"crossref","first-page":"267","DOI":"10.1007\/BF01931110","article-title":"A cyanoglucoside stored by a Sedum-feeding Apollo butterfly, Parnassius phoebus","volume":"51","author":"Nishida","year":"1995","journal-title":"Experientia"},{"key":"ref_152","doi-asserted-by":"crossref","first-page":"576","DOI":"10.1007\/BF01612411","article-title":"\u00dcber die Bildung von Cyanwasserstoffs\u00e4ure bei einem Myriapoden","volume":"28","year":"1882","journal-title":"Pfl\u00fcger Archiv F\u00fcr Die Gesamte Physiologie Des Menschen Der Tiere"},{"key":"ref_153","doi-asserted-by":"crossref","first-page":"468","DOI":"10.1007\/BF02952627","article-title":"\u00dcber eine cyanwasserstoffs\u00e4ure bereitende Dr\u00fcse","volume":"21","author":"Weber","year":"1882","journal-title":"Arch. Mikrosk. Anat."},{"key":"ref_154","first-page":"723","article-title":"Cyanide tolerance in millipedes: The biochemical basis","volume":"38B","author":"Hall","year":"1971","journal-title":"Comp. Biochem. Physiol."},{"key":"ref_155","unstructured":"Blum, M.S. (1981). Chemical Defenses of Arthropods, Academic Press."},{"key":"ref_156","first-page":"4","article-title":"Effectiveness of chemical defense in a tropical millipede species on a potential predator, the tarantula Megaphobema mesomelas","volume":"7","author":"Klem","year":"2017","journal-title":"Occam Razor"},{"key":"ref_157","doi-asserted-by":"crossref","first-page":"232","DOI":"10.1007\/s10886-011-9920-9","article-title":"Release of hydrogen cyanide via a post-secretion Schotten-Baumann reaction in defensive fluids of polydesmoid millipedes","volume":"37","author":"Kuwahara","year":"2011","journal-title":"J. Chem. Ecol."},{"key":"ref_158","first-page":"24","article-title":"Cassava variety tolerance to spider mite attack in relation to leaf cyanide level","volume":"3","author":"Mutisya","year":"2013","journal-title":"J. Biol. Agric. Healthc."},{"key":"ref_159","unstructured":"Urbanska, A., Leszczynski, B., Matok, H., and Dixon, A.F.G. (2002). Cyanide detoxifying enzymes of Bird cherry oat aphid. Electron. J. Pol. Agric. Univ., 5."},{"key":"ref_160","doi-asserted-by":"crossref","first-page":"1870","DOI":"10.1016\/j.phytochem.2008.03.018","article-title":"Frequency and distribution of cyanogenic glycosides in Eucalyptus L\u2019Herit","volume":"69","author":"Gleadow","year":"2008","journal-title":"Phytochemistry"},{"key":"ref_161","doi-asserted-by":"crossref","first-page":"36","DOI":"10.1111\/j.1440-6055.1967.tb02135.x","article-title":"Hydrogen cyanide in the defensive secretions of larval Paropsini (Coleoptera: Chrysomelidae)","volume":"6","author":"Moore","year":"1967","journal-title":"J. Aust. Entomol. Soc."},{"key":"ref_162","doi-asserted-by":"crossref","first-page":"127","DOI":"10.1007\/BF01240597","article-title":"Sequestration of plant secondary compounds by butterflies and moths","volume":"5","author":"Nishida","year":"1994","journal-title":"Chemoecology"},{"key":"ref_163","doi-asserted-by":"crossref","first-page":"1","DOI":"10.1080\/09168451.2014.877836","article-title":"Chemical ecology of insect-plant interactions: Ecological significance of plant secondary metabolites","volume":"78","author":"Nishida","year":"2014","journal-title":"Biosci. Biotechnol. Biochem."},{"key":"ref_164","doi-asserted-by":"crossref","first-page":"671","DOI":"10.1242\/jeb.013664","article-title":"Larvae of the fall webworm, Hyphantria cunea, inhibit cyanogenesis in Prunus serotina","volume":"211","author":"Fitzgerald","year":"2008","journal-title":"J. Exp. Biol."},{"key":"ref_165","doi-asserted-by":"crossref","first-page":"1283","DOI":"10.1007\/s10886-008-9545-9","article-title":"Aposematism in Archips cerasivoranus not linked to the sequestration of host-derived cyanide","volume":"34","author":"Fitzgerald","year":"2008","journal-title":"J. Chem. Ecol."},{"key":"ref_166","doi-asserted-by":"crossref","unstructured":"Stauber, E.J., Kuczka, P., van Ohlen, M., Vogt, B., Janowitz, T., Piotrowski, M., Beuerle, T., and Wittstock, U. (2012). Turning the \u2018mustard oil bomb\u2019 into a \u2018cyanide bomb\u2019: Aromatic glucosinolate metabolism in a specialist insect herbivore. PLoS ONE, 7.","DOI":"10.1371\/journal.pone.0035545"},{"key":"ref_167","unstructured":"Briolat, E.S., Zagrobelny, M., Olsen, C.E., Blount, J.D., and Stevens, M. (2018). Sex differences and dishonest aposematic signalling in the six-spot burnet moth (Zygaena filipendulae L.). Evolution, submitted manuscript."},{"key":"ref_168","doi-asserted-by":"crossref","unstructured":"Pentzold, S., Zagrobelny, M., Roelsgaard, P.S., M\u00f8ller, B.L., and Bak, S. (2014). The multiple strategies of an insect herbivore to overcome plant cyanogenic glucoside defence. PLoS ONE, 9.","DOI":"10.1371\/journal.pone.0091337"},{"key":"ref_169","doi-asserted-by":"crossref","unstructured":"Naumann, C.M., Tarmann, G.M., and Tremewan, W.G. (1999). The Western Palaearctic Zygaenidae: (Lepidoptera), Apollo Books.","DOI":"10.1163\/9789004631731"},{"key":"#cr-split#-ref_170.1","unstructured":"Dutreix, C., Naumann, C.M., and Tremewan, W.G. (1992). The reaction of birds to the larval defensive system of Zygaena trifolii (Esper, 1783) (Lepidoptera: Zygaenidae). Proceedings of the 4th Symposium on Zygaenidae"},{"key":"#cr-split#-ref_170.2","unstructured":"Nantes 11-13 September 1987. Recent advances in Burnet Moth Research (Lepidoptera: Zygaenidae), Koeltz Scientific Books."},{"key":"ref_171","doi-asserted-by":"crossref","first-page":"998","DOI":"10.2307\/2408077","article-title":"Survival of distasteful insects after being attacked by naive birds: A reappraisal of the theory of aposematic coloration evolving through individual selection","volume":"36","author":"Wiklund","year":"1982","journal-title":"Evolution"},{"key":"ref_172","doi-asserted-by":"crossref","first-page":"1189","DOI":"10.1016\/j.ibmb.2007.07.008","article-title":"Intimate roles for cyanogenic glucosides in the life cycle of Zygaena filipendulae (Lepidoptera, Zygaenidae)","volume":"37","author":"Zagrobelny","year":"2007","journal-title":"Insect Biochem. Mol. Biol."},{"key":"ref_173","doi-asserted-by":"crossref","first-page":"267","DOI":"10.1016\/0040-8166(85)90093-X","article-title":"Cuticular cavities: Storage chambers for cyanoglucoside-containing defensive secretions in larvae of a Zygaenid moth","volume":"17","author":"Franzl","year":"1985","journal-title":"Tissue Cell"},{"key":"ref_174","doi-asserted-by":"crossref","first-page":"22407","DOI":"10.1038\/srep22407","article-title":"Lepidopteran defence droplets\u2014A composite physical and chemical weapon against potential predators","volume":"6","author":"Pentzold","year":"2016","journal-title":"Sci. Rep."},{"key":"ref_175","doi-asserted-by":"crossref","first-page":"183","DOI":"10.1007\/BF00363935","article-title":"Cyanoglucoside storing cuticle of Zygaena larvae (Insecta, Lepidoptera)\u2014Morphological and cyanoglucoside changes during the molt","volume":"108","author":"Franzl","year":"1988","journal-title":"Zoomorphology"},{"key":"ref_176","doi-asserted-by":"crossref","first-page":"80","DOI":"10.1016\/j.ibmb.2014.04.001","article-title":"Transcriptional Regulation of De Novo Biosynthesis of cyanogenic glucosides throughout the life-cycle of the burnet moth Zygaena filipendulae (Lepidoptera)","volume":"49","author":"Zagrobelny","year":"2014","journal-title":"Insect Biochem. Mol. Biol."},{"key":"ref_177","doi-asserted-by":"crossref","first-page":"44","DOI":"10.1016\/j.ibmb.2013.11.003","article-title":"Sequestration, tissue distribution and developmental transmission of cyanogenic glucosides in a specialist insect herbivore","volume":"44","author":"Zagrobelny","year":"2014","journal-title":"Insect Biochem. Mol. Biol."},{"key":"ref_178","doi-asserted-by":"crossref","first-page":"284","DOI":"10.1111\/phen.12113","article-title":"Volatiles from the burnet moth Zygaena filipendulae (Lepidoptera) and associated flowers, and their involvement in mating communication","volume":"40","author":"Zagrobelny","year":"2015","journal-title":"Physiol. Entomol."},{"key":"ref_179","doi-asserted-by":"crossref","first-page":"107","DOI":"10.1016\/0031-9422(82)80023-X","article-title":"Sarmentosin epoxide, a new cyanogenic compound from Sedum Cepaea","volume":"21","author":"Nahrstedt","year":"1982","journal-title":"Phytochemistry"},{"key":"ref_180","doi-asserted-by":"crossref","first-page":"414","DOI":"10.1016\/j.pbi.2013.06.003","article-title":"A paleobiologic perspective on plant-insect interactions","volume":"16","author":"Labandeira","year":"2013","journal-title":"Curr. Opin. Plant Biol."},{"key":"ref_181","doi-asserted-by":"crossref","first-page":"211","DOI":"10.1007\/BF01021280","article-title":"Toxins in chrysomelid beetles possible evolutionary sequence from de novo synthesis to derivation from food-plant chemicals","volume":"16","author":"Pasteels","year":"1990","journal-title":"J. Chem. Ecol."},{"key":"ref_182","doi-asserted-by":"crossref","first-page":"124","DOI":"10.1055\/s-2007-971587","article-title":"Cyanogenic glycosides in butterflies: Detection and synthesis of linamarin and lotaustralin in the Heliconiinae","volume":"42","author":"Nahrstedt","year":"1981","journal-title":"Planta Med."},{"key":"ref_183","doi-asserted-by":"crossref","first-page":"542","DOI":"10.1021\/np010572c","article-title":"Plant analysis by butterflies: Occurrence of cyclopentenylglycines in Passifloraceae, Flacourtiaceae, and Turneraceae and discovery of the novel nonproteinogenic amino acid 2-(3\u2018-cyclopentenyl)glycine in Rinorea","volume":"65","author":"Clausen","year":"2002","journal-title":"J. Nat. Prod."},{"key":"ref_184","doi-asserted-by":"crossref","first-page":"1254","DOI":"10.1111\/jeb.12119","article-title":"Pollen feeding, resource allocation and the evolution of chemical defence in passion vine butterflies","volume":"26","author":"Cardoso","year":"2013","journal-title":"J. Evol. Biol."},{"key":"ref_185","doi-asserted-by":"crossref","unstructured":"Sekimura, T., and Nijhout, H.F. (2017). Chemical ecology of poisonous butterflies: Model or mimic? A paradox of sexual dimorphisms in M\u00fcllerian mimicry. Diversity and Evolution of Butterfly Wing Patterns, Springer.","DOI":"10.1007\/978-981-10-4956-9"},{"key":"ref_186","doi-asserted-by":"crossref","first-page":"1","DOI":"10.1016\/j.jep.2004.02.023","article-title":"Passiflora: A review update","volume":"94","author":"Dhawan","year":"2004","journal-title":"J. Ethnopharmacol."},{"key":"ref_187","doi-asserted-by":"crossref","unstructured":"Spencer, K.C. (1988). Chemical mediation of co-evolution in the Passiflora-Heliconius interaction. Chemical Mediation of Coevolution, Academic Press Inc.","DOI":"10.1016\/B978-0-12-656855-4.50011-5"},{"key":"ref_188","doi-asserted-by":"crossref","first-page":"144","DOI":"10.1038\/35018159","article-title":"Insect metabolism: Preventing cyanide release from leaves","volume":"406","author":"Engler","year":"2000","journal-title":"Nature"},{"key":"ref_189","doi-asserted-by":"crossref","first-page":"1455","DOI":"10.1023\/A:1020995329980","article-title":"Effects of cyanogenesis polymorphism in Turnera ulmifolia on Euptoieta hegesia and potential Anolis predators","volume":"25","author":"Schappert","year":"1999","journal-title":"J. Chem. Ecol."},{"key":"ref_190","doi-asserted-by":"crossref","first-page":"2177","DOI":"10.1007\/BF01014108","article-title":"Cyanoglycoside gynocardin from Acraea horta (L) (Lepidoptera, Acraeinae) possible implications for evolution of Acraeine host choice","volume":"15","author":"Raubenheimer","year":"1989","journal-title":"J. Chem. Ecol."},{"key":"ref_191","doi-asserted-by":"crossref","first-page":"515","DOI":"10.1016\/j.ympev.2007.11.024","article-title":"Phylogenetic relationships of butterflies of the tribe Acraeini (Lepidoptera, Nymphalidae, Heliconiinae) and the evolution of host plant use","volume":"46","author":"Wahlberg","year":"2008","journal-title":"Mol. Phylogenet. Evol."},{"key":"ref_192","unstructured":"Burkholder, P. (2018, March 13). Preferential Oviposition by Heliconiinae (Nymphalidae) Butterflies on Passiflora biflora (Passifloraceae) Leaves with Higher Cyanide Concentrations. Available online: http:\/\/digital.lib.usf.edu\/SFS0001216\/00001."},{"key":"ref_193","doi-asserted-by":"crossref","first-page":"307","DOI":"10.1111\/j.1365-3032.2006.00528.x","article-title":"Hydrogen cyanide release during feeding of generalist and specialist lepidopteran larvae on a cyanogenic plant, Passiflora capsularis","volume":"31","author":"Amelot","year":"2006","journal-title":"Physiol. Entomol."},{"key":"ref_194","doi-asserted-by":"crossref","first-page":"744","DOI":"10.1080\/15216540701736277","article-title":"Tipping the scales\u2014Specifier proteins in glucosinolate hydrolysis","volume":"59","author":"Wittstock","year":"2007","journal-title":"IUBMB Life"},{"key":"ref_195","doi-asserted-by":"crossref","unstructured":"Regier, J.C., Zwick, A., Cummings, M.P., Kawahara, A.Y., Cho, S., Weller, S., Roe, A., Baixeras, J., Brown, J.W., and Parr, C. (2009). Toward reconstructing the evolution of advanced moths and butterflies (Lepidoptera: Ditrysia): An initial molecular study. BMC Evol. Biol., 9.","DOI":"10.1186\/1471-2148-9-280"},{"key":"ref_196","first-page":"25","article-title":"De novo Synthesis vs. sequestration: Negatively correlated metabolic traits and the evolution of host plant specialization in cyanogenic butterflies","volume":"33","author":"Gilbert","year":"2008","journal-title":"J. Chem. Ecol."},{"key":"ref_197","doi-asserted-by":"crossref","first-page":"427","DOI":"10.1146\/annurev.en.26.010181.002235","article-title":"The biology of Heliconius and related genera","volume":"26","author":"Brown","year":"1981","journal-title":"Ann. Rev. Entomol."},{"key":"ref_198","doi-asserted-by":"crossref","first-page":"109","DOI":"10.1146\/annurev.en.21.010176.000545","article-title":"Host selection by insect parasitoids","volume":"21","author":"Vinson","year":"1976","journal-title":"Annu. Rev. Entomol."},{"key":"ref_199","doi-asserted-by":"crossref","first-page":"563","DOI":"10.1086\/285756","article-title":"Survival patterns and mortality sources of herbivorous insects-some demographic trends","volume":"145","author":"Cornell","year":"1995","journal-title":"Am. Nat."},{"key":"ref_200","unstructured":"Tremewan, W.G., Wipking, W., and Naumann, C.M. (1993, January 10\u201312). Host-searching and host-discrimination by a pupal parasitoid of Zygaena trifolii (Esper, 1783) (Lepidoptera, Zygaenidae). Proceedings of the 5th International Symposium on the Biology of the Zygaenidae (Insecta, Lepidoptera), Grietherbusch, Germany."},{"key":"ref_201","first-page":"143","article-title":"Nogle snyltehvepse kl\u00e6kket fra danske k\u00f8llesv\u00e6rmere (Lepidoptera, Zygaenidae: Zygaena Fabr. 1775, Hymenoptera: Braconidae, Ichneumonidae, Pteromalidae og Eupelmidae)","volume":"57","author":"Overgaard","year":"1989","journal-title":"Entomol. Medd."},{"key":"ref_202","doi-asserted-by":"crossref","first-page":"1027","DOI":"10.2298\/ABS1303027Z","article-title":"Parasitoid complex of Zygaena filipendulae L. (Lepidoptera; Zygaenidae)","volume":"65","author":"Zikic","year":"2013","journal-title":"Arch. Biol. Sci. Belgrade"},{"key":"ref_203","first-page":"287","article-title":"Alkaloid content of parasitoids reared from pupae of an alkaloid-sequestering Arctiid moth (Utetheisa ornatrix)","volume":"111","author":"Rossini","year":"2000","journal-title":"Entomol. News"},{"key":"ref_204","doi-asserted-by":"crossref","first-page":"992","DOI":"10.1007\/s10886-010-9840-0","article-title":"Caterpillar chemical defense and parasitoid success: Cotesia congregata parasitism of Ceratomia catalpae","volume":"36","author":"Lampert","year":"2010","journal-title":"J. Chem. Ecol."},{"key":"ref_205","unstructured":"Tremewan, W.G. (2006). Ecology, Phenotypes and the Mendelian Genetics of Burnet Moths, Gem Publishing Company."},{"key":"ref_206","doi-asserted-by":"crossref","first-page":"557","DOI":"10.1007\/BF00377274","article-title":"Repeated larval diapause and diapause-free development in geographic strains of the burnet moth Zygaena trifolii Esp (Insecta, Lepidoptera).1. Discontinuous clinal variation in photoperiodically controlled diapause induction","volume":"77","author":"Wipking","year":"1988","journal-title":"Oecologia"},{"key":"ref_207","unstructured":"Price, P., Lewinsohn, T., Fernandes, T., and Benson, W. (1991). Biodiversity of a Central American Heliconius community: Pattern, process, and problems. Plant-Animal Interactions: Evolutionary Ecology in Tropical and Temperate Regions, John Wiley & Sons."},{"key":"ref_208","unstructured":"Woelke, J. (2008). Egg Parasitoid Community on Heliconiini Butterflies in a Panamanian Rainforest. [Ph.D. Thesis, Wageningen University]."},{"key":"ref_209","doi-asserted-by":"crossref","first-page":"704","DOI":"10.1038\/433704a","article-title":"Butterfly anti-aphrodisiac lures parasitic wasps","volume":"433","author":"Fatouros","year":"2005","journal-title":"Nature"},{"key":"ref_210","first-page":"1","article-title":"Phylogeny, host association and biogeographical patterns in the diverse millipede-parasitoid genus Myriaphora Brown (Diptera: Phoridae)","volume":"34","author":"Hash","year":"2017","journal-title":"Cladistics"},{"key":"ref_211","doi-asserted-by":"crossref","first-page":"8","DOI":"10.1016\/j.cois.2015.11.005","article-title":"Sequestration of plant secondary metabolites by insect herbivores: Molecular mechanisms and ecological consequences","volume":"14","author":"Erb","year":"2016","journal-title":"Curr. Opin. Insect Sci."},{"key":"ref_212","doi-asserted-by":"crossref","first-page":"557","DOI":"10.1007\/BF02033701","article-title":"Uptake and sequestration of Ouabain and other cardiac glycosides in Danaus plexippus (Lepidoptera: Danaidae): Evidence for a carrier mediated process","volume":"21","author":"Frick","year":"1995","journal-title":"J. Chem. Ecol."},{"key":"ref_213","doi-asserted-by":"crossref","first-page":"895","DOI":"10.1016\/j.ibmb.2008.06.005","article-title":"De novo biosynthesis versus sequestration: A network of transport systems supports in iridoid producing leaf beetle larvae both modes of defense","volume":"38","author":"Kunert","year":"2008","journal-title":"Insect Biochem. Mol. Biol."},{"key":"ref_214","doi-asserted-by":"crossref","first-page":"e01096","DOI":"10.7554\/eLife.01096","article-title":"ABC transporter functions as a pacemaker for sequestration of plant glucosides in leaf beetles","volume":"2","author":"Strauss","year":"2013","journal-title":"Elife"},{"key":"ref_215","doi-asserted-by":"crossref","first-page":"531","DOI":"10.1038\/nature11285","article-title":"NRT\/PTR transporters are essential for translocation of glucosinolate defence compounds to seeds","volume":"488","author":"Andersen","year":"2012","journal-title":"Nature"},{"key":"ref_216","doi-asserted-by":"crossref","first-page":"37079","DOI":"10.1038\/srep37079","article-title":"The biosynthetic gene cluster for the cyanogenic glucoside dhurrin in Sorghum bicolor contains its co-expressed vacuolar MATE transporter","volume":"6","author":"Darbani","year":"2016","journal-title":"Sci. Rep."},{"key":"ref_217","doi-asserted-by":"crossref","first-page":"17","DOI":"10.1016\/j.cois.2015.12.004","article-title":"How herbivores coopt plant defenses: Natural selection, specialization, and sequestration","volume":"14","author":"Petschenka","year":"2016","journal-title":"Curr. Opin. Insect Sci."},{"key":"ref_218","doi-asserted-by":"crossref","first-page":"812","DOI":"10.1016\/j.ympev.2006.01.007","article-title":"Higher phylogeny of zygaenid moths (Insecta: Lepidoptera) inferred from nuclear and mitochondrial sequence data and the evolution of larval cuticular cavities for chemical defence","volume":"39","author":"Niehuis","year":"2006","journal-title":"Mol. Phylogenet. Evol."},{"key":"ref_219","doi-asserted-by":"crossref","first-page":"501","DOI":"10.1111\/j.1095-8312.2007.00858.x","article-title":"Evolutionary history of the burnet moth genus Zygaena Fabricius, 1775 (Lepidoptera: Zygaenidae) inferred from nuclear and mitochondrial sequence data: Phylogeny, host-plant association, wing pattern evolution and historical biogeography","volume":"92","author":"Niehuis","year":"2007","journal-title":"Biol. J. Linn. Soc."},{"key":"ref_220","doi-asserted-by":"crossref","first-page":"337","DOI":"10.1023\/A:1022629911304","article-title":"Sequestration and metabolism of protoxic pyrrolizidine alkaloids by larvae of the leaf beetle Platyphora boucardi and their transfer via pupae into defensive secretions of adults","volume":"29","author":"Pasteels","year":"2003","journal-title":"J. Chem. Ecol."},{"key":"ref_221","doi-asserted-by":"crossref","first-page":"1899","DOI":"10.1016\/j.phytochem.2009.08.002","article-title":"Always being well prepared for defense: The production of deterrents by juvenile Chrysomelina beetles (Chrysomelidae)","volume":"70","author":"Burse","year":"2009","journal-title":"Phytochemistry"},{"key":"ref_222","doi-asserted-by":"crossref","unstructured":"Opitz, S.E., Boeve, J.L., Nagy, Z.T., Sonet, G., Koch, F., and Muller, C. (2012). Host shifts from Lamiales to Brassicaceae in the sawfly genus Athalia. PLoS ONE, 7.","DOI":"10.1371\/journal.pone.0033649"},{"key":"ref_223","doi-asserted-by":"crossref","first-page":"39","DOI":"10.1007\/s00114-006-0154-6","article-title":"A male gift to its partner? Cyanogenic glycosides in a spermatophore of longwing butterflies (Heliconius)","volume":"94","author":"Cardoso","year":"2007","journal-title":"Naturwissenschaften"},{"key":"ref_224","unstructured":"Leather, S.R., and Hardie, J. (1995). Male nuptial gifts: Phenotypic consequences and evolutionary implications. Insect Reproduction, CRC Press."},{"key":"ref_225","doi-asserted-by":"crossref","first-page":"83","DOI":"10.1146\/annurev.ento.53.103106.093423","article-title":"Sexual conflict over nuptial gifts in Insects","volume":"53","author":"Gwynne","year":"2008","journal-title":"Annu. Rev. Entomol."},{"key":"ref_226","doi-asserted-by":"crossref","first-page":"1037","DOI":"10.1016\/j.ibmb.2013.08.007","article-title":"Male-to-female transfer of 5-hydroxytryptophan glucoside during mating in Zygaena filipendulae (Lepidoptera)","volume":"43","author":"Zagrobelny","year":"2013","journal-title":"Insect Biochem. Mol. Biol."},{"key":"ref_227","doi-asserted-by":"crossref","first-page":"5992","DOI":"10.1073\/pnas.85.16.5992","article-title":"Biparental defensive endowment of eggs with acquired plant alkaloid in the moth Utetheisa ornatrix","volume":"85","author":"Dussourd","year":"1988","journal-title":"Proc. Natl. Acad. Sci. USA"},{"key":"ref_228","doi-asserted-by":"crossref","unstructured":"Hilker, M., and Meiners, T. (2002). Paternal investment in egg defence. Chemoecology of Insect Eggs and Egg Deposition, Blackwell Publishing.","DOI":"10.1002\/9780470760253"},{"key":"ref_229","doi-asserted-by":"crossref","first-page":"283","DOI":"10.1007\/s002650000292","article-title":"Precopulatory assessment of male quality in an arctiid moth (Utetheisa ornatrix): Hydroxydanaidal is the only criterion of choice","volume":"49","author":"Iyengar","year":"2001","journal-title":"Behav. Ecol. Sociobiol."},{"key":"ref_230","doi-asserted-by":"crossref","first-page":"1019","DOI":"10.1042\/bj1171019","article-title":"The activities of proline dehydrogenase, glutamate dehydrogenase, aspartate-oxoglutarate aminotransferase and alanine-oxoglutarate aminotransferase in some insect flight muscles","volume":"117","author":"Crabtree","year":"1970","journal-title":"Biochem. J."},{"key":"ref_231","doi-asserted-by":"crossref","first-page":"1","DOI":"10.1016\/0010-406X(61)90188-8","article-title":"Properties of transaminases and glutamic dehydrogenase in the cockroach Periplaneta americana","volume":"3","author":"Mcallan","year":"1961","journal-title":"Comp. Biochem. Physiol."},{"key":"ref_232","doi-asserted-by":"crossref","first-page":"169","DOI":"10.1006\/eesa.1996.1504","article-title":"Changes in protein metabolism in hemolymph and fat body of the silkworm, Bombyx mori (Lepidoptera: Bombycidae) in response to organophosphorus insecticides toxicity","volume":"36","author":"Nath","year":"1997","journal-title":"Ecotoxicol. Environ. Saf."},{"key":"ref_233","unstructured":"Gilbert, L.E. (2009). Chitin metabolism in insects. Insect Development: Morphogenesis, Molting and Metamorphosis, Academic Press."},{"key":"ref_234","doi-asserted-by":"crossref","first-page":"409","DOI":"10.1007\/s00442-008-1096-9","article-title":"Positive effects of cyanogenic glycosides in food plants on larval development of the common blue butterfly","volume":"157","author":"Goverde","year":"2008","journal-title":"Oecologia"}],"container-title":["Insects"],"original-title":[],"language":"en","link":[{"URL":"https:\/\/www.mdpi.com\/2075-4450\/9\/2\/51\/pdf","content-type":"unspecified","content-version":"vor","intended-application":"similarity-checking"}],"deposited":{"date-parts":[[2025,10,11]],"date-time":"2025-10-11T15:03:10Z","timestamp":1760194990000},"score":1,"resource":{"primary":{"URL":"https:\/\/www.mdpi.com\/2075-4450\/9\/2\/51"}},"subtitle":[],"short-title":[],"issued":{"date-parts":[[2018,5,3]]},"references-count":235,"journal-issue":{"issue":"2","published-online":{"date-parts":[[2018,6]]}},"alternative-id":["insects9020051"],"URL":"https:\/\/doi.org\/10.3390\/insects9020051","relation":{},"ISSN":["2075-4450"],"issn-type":[{"value":"2075-4450","type":"electronic"}],"subject":[],"published":{"date-parts":[[2018,5,3]]}}}