title: Occurrence of sarmentosin and other hydroxynitrile glucosides in Parnassius (papilionidae) butterflies and their food plants.
abstract: Sequestration of plant secondary metabolites is a widespread phenomenon among aposematic insects. Sarmentosin is an unsaturated γ-hydroxynitrile glucoside known from plants and some Lepidoptera. It is structurally and biosynthetically closely related to cyanogenic glucosides, which are commonly sequestered from food plants and/or de novo synthesized by lepidopteran species. Sarmentosin was found previously in Parnassius (Papilionidae) butterflies, but it was not known how the occurrence was related to food plants or whether Parnassius species could biosynthesize the compound. Here, we report on the occurrence of sarmentosin and related compounds in four different Parnassius species belonging to two different clades, as well as their known and suspected food plants. There were dramatic differences between the two clades, with P. apollo and P. smintheus from the Apollo group containing high amounts of sarmentosin, and P. clodius and P. mnemosyne from the Mnemosyne group containing low or no detectable amounts. This was reflected in the larval food plants; P. apollo and P. smintheus larvae feed on Sedum species (Crassulaceae), which all contained considerable amounts of sarmentosin, while the known food plants of the two other species, Dicentra and Corydalis (Fumariaceae), had no detectable levels of sarmentosin. All insects and plants containing sarmentosin also contained other biosynthetically related hydroxynitrile glucosides in patterns previously reported for plants, but not for insects. Not all findings could be explained by sequestration alone and we therefore hypothesize that Parnassius species are able to de novo synthesize sarmentosin.
authors.affiliation: Plant Biochemistry Laboratory, Department of Plant Biology and Biotechnology and the VKR Centre of Excellence Pro-Active Plants, University of Copenhagen, 40 Thorvaldsensvej, Frederiksberg C, 1871, Denmark. nnb@life.ku.dk
authors.forename: Nanna
authors.initials: N
authors.lastname: Bjarnholt
authors.forename: Mirosław
authors.initials: M
authors.lastname: Nakonieczny
authors.forename: Andrzej
authors.initials: A
authors.lastname: Kędziorski
authors.forename: Diane M
authors.initials: DM
authors.lastname: Debinski
authors.forename: Stephen F
authors.initials: SF
authors.lastname: Matter
authors.forename: Carl Erik
authors.initials: CE
authors.lastname: Olsen
authors.forename: Mika
authors.initials: M
authors.lastname: Zagrobelny
mesh_terms: D000818:Animals; D002080:Butterflies / Q000502:physiology*; D029627:Crassulaceae / Q000378:metabolism*; D031310:Fumarioideae / Q000378:metabolism*; D005947:Glucose / Q000031:analogs & derivatives* / Q000302:isolation & purification / Q000378:metabolism; D005960:Glucosides / Q000302:isolation & purification / Q000378:metabolism*; D060434:Herbivory; D009570:Nitriles / Q000302:isolation & purification / Q000378:metabolism*
chemical_list: D005960:Glucosides; D009570:Nitriles; C082842:sarmentosine; D005947:Glucose