The caterpillars of several kinds of arctiid mothingest pyrrolizidine alkaloids—substances which plants produce to deter herbivores—and use them as protection against insectivores. The larva converts the alkaloid into an N-oxide for storage; on metamorphosis, the alkaloid is retained and used by the adult. This was discovered after the observation that Utetheisa ornatrix moths caught in spiderwebs were cut loose by the spiders.
Many insects that carry pyrrolizidine alkaloids are brightly-colored to signal their toxicity.
Male tiger moths convert the alkaloid through various intermediate stages[2] into the pheromone hydroxydanaidal;[3] female moth prefer males with more pheromone, since the alkaloid will be transferred into her eggs and protect them from predation.
Referencesedit
^RÖMPP Lexikon Naturstoffe. Stuttgart: Verlag Thieme. 1997. p. 170. ISBN978-3137499015.
^S Schulz; W Francke; M Boppré; T Eisner; J Meinwald (Jul 15, 1993). "Insect pheromone biosynthesis: stereochemical pathway of hydroxydanaidal production from alkaloidal precursors in Creatonotos transiens (Lepidoptera, Arctiidae)". PNAS. 90 (14): 6834–6838. Bibcode:1993PNAS...90.6834S. doi:10.1073/pnas.90.14.6834. PMC47027. PMID 11607415.
^J A Edgar, M Boppré, E Kaufmann; Boppré; Kaufmann (2007). "Insect-synthesised Retronecine Ester Alkaloids: Precursors of the Common Arctiine (Lepidoptera) Pheromone Hydroxydanaidal". J Chem Ecol. 33 (12): 2266–2280. doi:10.1007/s10886-007-9378-y. PMID 18030534. S2CID 8963122.{{cite journal}}: CS1 maint: multiple names: authors list (link)
April 18, 2024
hydroxydanaidal, insect, pheromone, synthesized, some, species, moth, from, pyrrolizidine, alkaloids, found, their, diet, names, iupac, name, hydroxy, dihydro, pyrrolizin, carboxaldehyde, identifiers, number, 34199, model, jsmol, interactive, image, chemspider. Hydroxydanaidal is an insect pheromone synthesized by some species of moth from pyrrolizidine alkaloids found in their diet Hydroxydanaidal Names IUPAC name 7 Hydroxy 6 7 dihydro 5H pyrrolizin 1 carboxaldehyde Identifiers CAS Number 34199 35 4 3D model JSmol Interactive image ChemSpider 142107 PubChem CID 161805 UNII CCJ9N9N4QT Y CompTox Dashboard EPA DTXSID60955744 InChI InChI 1S C8H9NO2 c10 5 6 1 3 9 4 2 7 11 8 6 9 h1 3 5 7 11H 2 4H2Key QJXKHTIRIREIAG UHFFFAOYSA N SMILES O Cc1ccn2CC C H O c12 Properties Chemical formula C 8H 9N O 2 Molar mass 151 165 g mol 1 Appearance Solid Melting point 55 C 131 F 328 K 1 Except where otherwise noted data are given for materials in their standard state at 25 C 77 F 100 kPa Infobox referencesUse editThe caterpillars of several kinds of arctiid moth ingest pyrrolizidine alkaloids substances which plants produce to deter herbivores and use them as protection against insectivores The larva converts the alkaloid into an N oxide for storage on metamorphosis the alkaloid is retained and used by the adult This was discovered after the observation that Utetheisa ornatrix moths caught in spiderwebs were cut loose by the spiders Many insects that carry pyrrolizidine alkaloids are brightly colored to signal their toxicity Male tiger moths convert the alkaloid through various intermediate stages 2 into the pheromone hydroxydanaidal 3 female moth prefer males with more pheromone since the alkaloid will be transferred into her eggs and protect them from predation References edit ROMPP Lexikon Naturstoffe Stuttgart Verlag Thieme 1997 p 170 ISBN 978 3137499015 S Schulz W Francke M Boppre T Eisner J Meinwald Jul 15 1993 Insect pheromone biosynthesis stereochemical pathway of hydroxydanaidal production from alkaloidal precursors in Creatonotos transiens Lepidoptera Arctiidae PNAS 90 14 6834 6838 Bibcode 1993PNAS 90 6834S doi 10 1073 pnas 90 14 6834 PMC 47027 PMID 11607415 J A Edgar M Boppre E Kaufmann Boppre Kaufmann 2007 Insect synthesised Retronecine Ester Alkaloids Precursors of the Common Arctiine Lepidoptera Pheromone Hydroxydanaidal J Chem Ecol 33 12 2266 2280 doi 10 1007 s10886 007 9378 y PMID 18030534 S2CID 8963122 a href Template Cite journal html title Template Cite journal cite journal a CS1 maint multiple names authors list link Retrieved from https en wikipedia org w index php title Hydroxydanaidal amp oldid 1105133300, wikipedia, wiki, book, books, library,
