Pelargonidin 3-malonylsophoroside from the red Iceland poppy, Papaver nudicaule

Cornuz, Georges; Wyler, Hugo; Lauterwein, Jürgen

doi:10.1016/0031-9422(81)80075-1

Cited by 28 publications

(12 citation statements)

References 8 publications

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“…White petals from this species contain flavonols 1-8, and red petals are colored by the pelargonidin derivatives, pelargonidin 3-O-b-sophoroside-7-O-bglucoside (9), pelargonidin 3-O-b-sophoroside (12) and pelargonidin 3-O-b-[(6-malonyl)-sophoroside] (13) ( Fig. 2) as reported earlier (Cornuz et al, 1981). Nudicaulins were not found in white and red petals.…”

Section: Identification Of Compoundssupporting

confidence: 80%

Occurrence of nudicaulin structural variants in flowers of papaveraceous species

Tatsis

Böhm²,

Schneider

2013

Phytochemistry

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The intense color of yellow Papaver nudicaule flowers is conferred by the presence of nudicaulins, a group of alkaloids with a unique pentacyclic skeleton composed of an indole ring and a polyphenolic moiety. Petals from eight different Papaveraceae species composed of different color varieties were probed for the presence of nudicaulins. In addition to their occurrence in yellow P. nudicaule flowers, nudicaulins I-VIII were detected and quantified in orange flowers of P. nudicaule, and in yellow and orange Papaver alpinum flowers. Meconopsis cambrica petals showed a divergent nudicaulin spectrum, with compounds having an attached 3-hydroxy-3-methyl-glutaryl group (HMG) instead of a malonyl unit at one of the glucose units. Flavonols and anthocyanins that accompany nudicaulins were identified. The taxonomical significance of the occurrence of nudicaulins is briefly discussed.

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Section: Identification Of Compoundssupporting

confidence: 80%

Occurrence of nudicaulin structural variants in flowers of papaveraceous species

Tatsis

Böhm²,

Schneider

2013

Phytochemistry

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“…All vicinal coupling constants of H-2" -H-5" were around 9 Hz, in agreement with a 4C1 conformation of the sugar residue (see Table l). The sugar proton data obtained differ from data reported for 3-diglycoside substituted anthocyanins [8]. Although in the latter case an external glucose is linked in position 2" to an internal glucose and the aglycon carries a psotive charge, and effect of the aqueous acidic solvent used by these authors could not be excluded.…”

Section: Nuclear Magnetic Resonance Investigationscontrasting

confidence: 73%

“…These signals represent the AB part of an ABX system formed with H-5". Such signals were to be expected for 6"-O-acyl derivatives [8,. Irradiation at 4.40 pprn (H-6") or 3.84 ppm (H-5", see Table 1) led to either a broad doublet with J = 8 Hz or an AB system for the respective coupling partners.…”

Section: Of the Carbon Atoms In Nuclear Magnetic Resonance Spectra Qfmentioning

confidence: 58%

Conformational Changes of Apigenin 7‐O‐(6‐O‐malonylglucoside), a Vacuolar Pigment from Parsley, with Solvent Composition and Proton Concentration

Matern

Heller

Himmelspach

1983

European Journal of Biochemistry

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Malonylated apigenin 7-0-glucoside was prepared from malonyl-CoA and apigenin 7-0-glucoside using a malonyltransferase from parsley cell cultures. The enzyme product, as well as the flavonoid substrate, was analyzed by high-resolution nuclear magnetic resonance spectroscopy, confirming that malonic acid had been attached to the primary hydroxyl of the glucose moiety of apigenin 7-0-glucoside. During these studies in several solvents, it became apparent that, in particular, the chemical shift of H-6"A and the coupling constants J5.,,6..A and J5rf,6ffB were dependent on solvent composition and proton concentration. Similar changes of sugar proton resonance frequencies were also observed with methyl 6-O-malonyl-~-~-glucopyranoside, but not with apigenin 7-0-[6-0-(4-coumaroyl)glucoside]. The change of coupling constants is ascribed to a conformational modification of the sugar portion in the malonylglucosides.Malonylated flavonoid glycosides are exclusively located within the vacuoles of parsley cells. We propose that acylation of flavonoid glycosides which are synthesized in the cytoplasm facilitates transport of the substrates into the vacuole. The conformational modification which is induced by changes in proton concentration may provide a mechanism to trap flavonoids in situ.

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“…Identical acylated carbohydrate units are attached not only to the mentioned aglycones, but also to pelargonidin in the red cultivar of P. nudicaule. [18] Hence, several constituents of the flavonoid pathway Nudicaulins are ag roup of indole alkaloid glycosides responsible for the color of yellow petals of Papaver nudicaule (Iceland poppy). The unique aglycone scaffold of these alkaloids attracted our interest as one of the most unusualf lavonoid-indole hybrid structures that occur in nature.…”

Section: Introductionmentioning

confidence: 99%

Unprecedented Utilization of Pelargonidin and Indole for the Biosynthesis of Plant Indole Alkaloids

et al. 2016

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Nudicaulins are a group of indole alkaloid glycosides responsible for the color of yellow petals of Papaver nudicaule (Iceland poppy). The unique aglycone scaffold of these alkaloids attracted our interest as one of the most unusual flavonoid‐indole hybrid structures that occur in nature. Stable isotope labeling experiments with sliced petals identified free indole, but not tryptamine or l‐tryptophan, as one of the two key biosynthetic precursors of the nudicaulin aglycone. Pelargonidin was identified as the second key precursor, contributing the polyphenolic unit to the nudicaulin molecule. This finding was inferred from the temporary accumulation of pelargonidin glycosides in the petals during flower bud development and a drop at the point in time when nudicaulin levels start to increase. The precursor‐directed incorporation of cyanidin into a new 3′‐hydroxynudicaulin strongly supports the hypothesis that anthocyanins are involved in the biosynthesis of nudicaulins.

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Pelargonidin 3-malonylsophoroside from the red Iceland poppy, Papaver nudicaule

Cited by 28 publications

References 8 publications

Occurrence of nudicaulin structural variants in flowers of papaveraceous species

Occurrence of nudicaulin structural variants in flowers of papaveraceous species

Conformational Changes of Apigenin 7‐O‐(6‐O‐malonylglucoside), a Vacuolar Pigment from Parsley, with Solvent Composition and Proton Concentration

Unprecedented Utilization of Pelargonidin and Indole for the Biosynthesis of Plant Indole Alkaloids

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