Flavonols and an indole alkaloid skeleton bearing identical acylated glycosidic groups from yellow petals of Papaver nudicaule

Characterization and determination of trace alkaloids in seeds extracts fromPeganum harmalalinn. Using LC-ESI-MS and HPLC

“…The observation of [M+H−162] + and [M+H−162−162] + ion corresponding to the successive loss of two 162 Da, provided clear evidence of existing two deoxyhexoses linking to the sole hydroxyl group at C-3 in the structure. Similar cleavages of glycosidic bonds had been reported in alkaloids previously [30]. Peak 1 presented the similar UV spectra with vasicine which had maximum absorptions at 219 and 285 nm, respectively.…”

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

“…This is because the nudicaulins naturally occurring in the petals of P. nudicaule each possess a hydroxy group in the 4′‐position of the phenylpropanoid‐derived phenyl ring. With the exception of gossypitrin, no 3′,4′‐dihydroxy substitution (catechol moiety) or 3′,4′,5′‐trihydroxy substitution of phenolics has so far been detected in this plant,11 probably because corresponding precursors are not utilized in the biosynthesis of the nudicaulins or do not exist in P. nudicaule . Hence, in the latter case, the successful incorporation into nudicaulins of a precursor possessing such an unusual substitution pattern would strongly indicate that the suggested pathway proceeds through an anthocyanidin.…”

“…The flavonoid fraction was eluted with MeOH (6 mL), followed by nudicaulin elution with concentrated aqueous NH 3 /methanol (1:3, v / v , 6 mL). Six out of the eight nudicaulins that have been identified in flowers of P. nudicaule exist in the form of acylated glucosides 11. In order to simplify the structural diversity to that of nudicaulin diastereomers I and II, the acyl units were removed by basic hydrolysis.…”

“…It is interesting in this context that some kaempferol derivatives and gossypitrin co‐occur with nudicaulins in the yellow petals of P. nudicaule 11. Moreover, the nudicaulins and the kaempferols in these petals are identically glycosylated and malonylated.…”

Anti-Diabetic Effects of a Kaempferol Glycoside-Rich Fraction from Unripe Soybean (Edamame,Glycine maxL. Merrill. ‘Jindai’) Leaves on KK-AyMice

“…A cross peak between an anomeric proton at 4.31 (1H, bs) and C-6 00 at 66.08 of the core sugar moiety indicates that the other moiety with the anomeric proton at 4.31 (rhamnose) was attached to C-6 00 of the core sugar (glucose) moiety via the 1 0000 -hydroxyl group. Chemical shifts due to two-molecule sugar moieties (the core sugar moiety þ sugar moiety with the anomeric proton at 4.58 (1H, d, J ¼ 7:8 Hz)) of compound b in the 13 C-NMR spectrum were very similar to those of kaempferol 3-O-sophoroside, 18) except for the downfield shift of C-6 00 of the core sugar moiety, indicating that compound b was kaempferol 3-O-sophoroside attached to a sugar moiety at its C-6 00 position. The chemical shifts of the sugar moiety attached to C-6 00 were almost the same as those of compound a, indicating that the sugar moiety was rhamnose.…”