title: Oviposition stimulants for the monarch butterfly: flavonol glycosides from Asclepias curassavica.
abstract: The monarch butterfly, Danaus plexippus oviposits on milkweed plants, primarily within the Asclepiadaceae. Oviposition stimulants responsible for host plant recognition were isolated from Asclepias curassavica. Six flavonoid glycosides-quercetin 3-O-(2",6"-alpha-L-dirhamnopyranosyl)-beta-D-galactopyranoside, quercetin 3-O-beta-D-glucopyranosyl-(1-->6)-beta-D-galactopyranoside, quercetin 3-O-(2"-O-alpha-L-rhamnopyranosyl)-beta-D-galactopyranoside, quercetin 3-O-alpha-L-rhamnopyranosyl-(1-->6)-beta-D-glucopyranoside, quercetin 3-O-beta-D-galactopyranoside, quercetin 3-O-beta-D-glucopyranoside, and an unidentified flavonoid mixture were isolated and characterized from this plant. An additional glycoside, possibly quercetin 3-O-(2",6"-alpha-L-dirhamnopyranosyl)-beta-D-glucopyranoside, which could not be separated from the first triglycoside, was also found in some batches of plant extract. The two dirhamnosyl glycosides, the glucosylgalactose and the rutinoside were found to be active as oviposition stimulants at 0.5 g leaf equivalents.
authors.affiliation: Boyce Thompson Institute at Cornell University, Ithaca, NY 14853, USA.
authors.forename: M
authors.initials: M
authors.lastname: Haribal
authors.forename: J A
authors.initials: JA
authors.lastname: Renwick
mesh_terms: D000818:Animals; D002080:Butterflies / Q000033:anatomy & histology*; D002236:Carbohydrate Conformation; D002240:Carbohydrate Sequence; D005260:Female; D005419:Flavonoids / Q000737:chemistry / Q000302:isolation & purification / Q000494:pharmacology*; D044948:Flavonols; D006027:Glycosides / Q000737:chemistry / Q000302:isolation & purification / Q000494:pharmacology*; D009682:Magnetic Resonance Spectroscopy; D008958:Models, Molecular; D008969:Molecular Sequence Data; D010058:Oviposition / Q000187:drug effects*; D010936:Plant Extracts
chemical_list: D005419:Flavonoids; D044948:Flavonols; D006027:Glycosides; D010936:Plant Extracts