Flavonols and an indole alkaloid skeleton bearing identical acylated glycosidic groups from yellow petals of Papaver nudicaule.
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.
Schliemann
Willibald
W
Department of Secondary Metabolism, Leibniz Institute of Plant Biochemistry, Weinberg 3, D-06120 Halle (Saale), Germany. willibald.schliemann@ipb-halle.de
Schneider
Bernd
B
Wray
Victor
V
Schmidt
Jürgen
J
Nimtz
Manfred
M
Porzel
Andrea
A
Böhm
Hartmut
H
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
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