title: Flavonols and an indole alkaloid skeleton bearing identical acylated glycosidic groups from yellow petals of Papaver nudicaule.
abstract: From yellow petals of Iceland poppy, besides the known flavonoid gossypitrin, seven kaempferol derivatives were isolated. In addition to kaempferol 3-O-beta-sophoroside and kaempferol 3-O-beta-sophoroside-7-O-beta-glucoside, known from other plants, the mono- and dimalonyl conjugates of the latter were identified by MS and NMR spectroscopy. Structure analyses of a set of co-occurring pigments, the nudicaulins, revealed that they have the identical acylated glycoside moieties attached to a pentacyclic indole alkaloid skeleton for which the structure of 19-(4-hydroxyphenyl)-10H-1,10-ethenochromeno[2,3-b]indole-6,8,18-triol was deduced from MS and NMR as well as chemical and chiroptical methods.
authors.affiliation: Department of Secondary Metabolism, Leibniz Institute of Plant Biochemistry, Weinberg 3, D-06120 Halle (Saale), Germany. willibald.schliemann@ipb-halle.de
authors.forename: Willibald
authors.initials: W
authors.lastname: Schliemann
authors.forename: Bernd
authors.initials: B
authors.lastname: Schneider
authors.forename: Victor
authors.initials: V
authors.lastname: Wray
authors.forename: Jürgen
authors.initials: J
authors.lastname: Schmidt
authors.forename: Manfred
authors.initials: M
authors.lastname: Nimtz
authors.forename: Andrea
authors.initials: A
authors.lastname: Porzel
authors.forename: Hartmut
authors.initials: H
authors.lastname: Böhm
mesh_terms: D000470:Alkaloids / Q000737:chemistry* / Q000302:isolation & purification; D002851:Chromatography, High Pressure Liquid; D044948:Flavonols / Q000737:chemistry* / Q000302:isolation & purification; D035264:Flowers / Q000737:chemistry*; D005960:Glucosides / Q000737:chemistry / Q000302:isolation & purification; D006027:Glycosides / Q000737:chemistry* / Q000302:isolation & purification; D006868:Hydrolysis; D026121:Indole Alkaloids / Q000737:chemistry; D007211:Indoles / Q000737:chemistry* / Q000302:isolation & purification; D044949:Kaempferols / Q000737:chemistry / Q000302:isolation & purification; D009682:Magnetic Resonance Spectroscopy / Q000379:methods / Q000592:standards; D013058:Mass Spectrometry / Q000379:methods; D015394:Molecular Structure; D010207:Papaver / Q000737:chemistry* / Q000145:classification; D012015:Reference Standards
chemical_list: D000470:Alkaloids; D044948:Flavonols; D005960:Glucosides; D006027:Glycosides; D026121:Indole Alkaloids; D007211:Indoles; D044949:Kaempferols; C509452:kaempferol 3-O-sophoroside-7-O-glucoside; C064309:kaempferol 3-O-sophoroside