title: Acylated peonidin glycosides from duskish mutant flowers of Ipomoea nil.
abstract: Five acylated peonidin glycosides were isolated from the pale gray-purple flowers of a duskish mutant in the Japanese morning glory (Ipomoea nil or Pharbitis nil) as major pigments, along with a known anthocyanin, Heavenly Blue Anthocyanin (HBA). Three of these were based on peonidin 3-sophoroside and two on peonidin 3-sophoroside-5-glucoside as their deacylanthocyanins; both deacylanthocyanins were acylated with caffeic acid and/or glucosylcaffeic acids. By spectroscopic and chemical methods, the structures of the former three pigments were determined to be 3-O-[2-O-(6-O-(trans-caffeoyl)-beta-D-glucopyranosyl)-beta-D-glucopyranoside], 3-O-[2-O-(6-O-(3-O-(beta-D-glucopyranosyl)-trans-caffeoyl)-beta-D-glucopyranosyl)-6-O-(4-O-(6-O-(3-O-(beta-D-glucopyranosyl)-trans-caffeoyl)-beta-D-glucopyranosyl)-trans-caffeoyl)-beta-glucopyranoside], and 3-O-[2-O-(6-O-(trans-caffeoyl)-beta-D-glucopyranosyl)-6-O-(4-O-(6-O-(3-O-(beta-D-glucopyranosyl)-trans-caffeoyl)-beta-D-glucopyranosyl)-trans-caffeoyl)-beta-D-glucopyranoside] of peonidin. The structures of the latter two pigments were also confirmed as 3-O-[2-O-(6-O-(trans-caffeoyl)-beta-D-glucopyranosyl)-beta-D-glucopyranoside]-5-O-beta-D-glucopyranoside, and 3-O-[2-O-(6-O-(trans-caffeoyl)-beta-D-glucopyranosyl)-6-O-(4-O-(6-O-(3-O-(beta-D-glucopyranosyl)-trans-caffeoyl)-beta-D-glucopyranosyl)-trans-caffeoyl)-beta-D-glucopyranoside]-5-O-beta-D-glucopyranoside of peonidin. The mutation affecting glycosylation and acylation in anthocyanin biosynthesis of Japanese morning glory was discussed.
authors.affiliation: Chemical Laboratory, Meiji-Gakuin University, Totsuka, Yokohama 244-8539, Japan.
authors.forename: Norio
authors.initials: N
authors.lastname: Saito
authors.forename: Kenjiro
authors.initials: K
authors.lastname: Toki
authors.forename: Yasumasa
authors.initials: Y
authors.lastname: Morita
authors.forename: Atsushi
authors.initials: A
authors.lastname: Hoshino
authors.forename: Shigeru
authors.initials: S
authors.lastname: Iida
authors.forename: Atsushi
authors.initials: A
authors.lastname: Shigihara
authors.forename: Toshio
authors.initials: T
authors.lastname: Honda
mesh_terms: D000215:Acylation; D000872:Anthocyanins / Q000737:chemistry* / Q000302:isolation & purification; D035264:Flowers / Q000235:genetics*; D006027:Glycosides / Q000737:chemistry* / Q000302:isolation & purification; D019657:Solanaceae / Q000737:chemistry* / Q000235:genetics*
chemical_list: D000872:Anthocyanins; D006027:Glycosides; C473205:peonidin