Papaver rhoeas

Rhoedans Rhoeadine (MD-Phe C90N Phe-MD) (Papaver rhoeas (red poppy) (Papaveraceae) narcotic). 

Franklin-Tong, VE., Drbak, B., Allan, A.C., Watkins, P.A.C. and Trewavas, A.J., 1996, Growth of pollen tubes of Papaver rhoeas is regulated by a slow-moving calcium wave propagated by inositol 1,4,5-trisphosphate. Plant Cell 1305-1321. 

Narcotine has been reported as present in Papaver rhoeas L. 33) and P. paeoniflorum Hort. 34). Some other sources are doubtful its occurrence in Rauwolfia heterophylla Roehm and Schult. 35) may be due to industrial impurities 36), and, for the same reason, the isolation of narcotine from Strychnos melinoniana Baillon is questionable 37). 

Papaver Rhoeas are often found on arable land, road sides, gravel pits and waste places. The corn poppy produces large red flowers The stalks are distinctive because of the coarse, spreading hairs. The leaves are stalkless with coarsely toothed lobes. The large solitary poppy-like flowers with bright red petals are produced during the summer. The seed capsule is hairless and more or less globular, often with a whitish bloom. 

Papaver rhoeas and hydrogen peroxide only gave a low yield of the hydroxy-derivative (37 R = OH)79 (see also Sections 3D and 31). 

The formation of ( )-/2-hydroxyreticuline by treatment of ( )-reticuline with homogenized Papaver rhoeas and hydrogen peroxide may offer an initial clue to the biosynthesis of the rhoeadine alkaloids79 (see also Section 3A). 

In 1837 E. Merck 346) discovered the presence of a substance in opium which turned deep red when treated with mineral acids. He named the substance porphyroxine and Berzelius (72) renamed it opine. In 1865 Hesse 212,213) reported the isolation of rhoeadine from Papaver rhoeas which he thought was identical with Merck s porphyroxine. However, 3 years later he recognized 214) that he was mistaken he assigned the name meconidine 215) to the substance which when treated with mineral acids was responsible for the red coloration. These findings showed that a... 

Glaucium flavum G. comiculatum Hydrastis canadensis Papaver rhoeas,... 

Eschscholtzia oregana, and E. califomica and the /3-form in Glaucium comiculatum, Papaver rhoeas, and P. syriacum. The alkaloid content of Argemone mexicana, and particularly the presence of four quaternary bases, namely (—)-/3-scoulerine methohydroxide, (-)-cheilanthifoline, and both the a- and /8-methohydroxides of (-)-stylopine, suggests a close relationship between this plant and A. ochroleuca and A. albiflora (cf Vol. 5). ° Similarly, the presence of (-)-scoulerine and the benzophenanthridine norchelerythrine in A. polyanthemos confirms its close biochemical relationship with A. albiflora. ... 

SophorOside, C27H3lCIOl6, mecocyanirt. From the flow ers of Papaver rhoeas L,P Papayeraceae Willstatter Weil,... 

Sensitive species are those, which are gradually eliminated from the polluted area, such as Capsella bursa-pastoris, Cardaria dvaba, Cichorium in-tybus, Dactylis glomerata, Stellaria media, Veronica hederifolia, Hypericum perforatum, Plantago major, Papaver rhoeas, Viola tricolor, Melilotus officinalis, Onopordum acanthium, Symphytum officinale. Ranunculus arven-... 

The isolation of (— )-iV-methylstylopinium chloride from Papaver rhoeas represents the first time that a quaternary tetrahydroprotoberberine alkaloid has been isolated from the Papaver genus. Treatment of this alkaloid with base in DMSO solution gave the Hofmann product (149). This type of product has not been obtained by Hofmann degradation of JV-methyltetrahydrober-berinium or iV-methyltetrahydropseudoprotoberberinium alkaloids. Of the alkaloids isolated from Thalictrum polygonum, only berberine was shown to exhibit weak antimicrobial activity.The alkaloid content of Chelidonium majus was studied as a function of the drying procedure of the plant. ... 

Berberine, coptisine, and /3-stylopine methohydroxide have been isolated from Papaver rhoeas L., berberine, berberubine, isocorypalmine, and thalifendine from Thalictrum dioicum, berberine from T. sachalinense, corydaline from Corydalis marschalliana, scoulerine, ophiocarpine, isocorypalmine, and cheilanthifoline from C. vaginans, C. gigantea, and C marschalliana, and ophiocarpine, stylopine, cheilanthifoline, isocorypalmine, and the chlorides of berberine, coptisine, and dehydrocheilanthifoline from C. ophiocarpa. The alkaloids of C. ophiocarpa were separated by droplet counter-current chromatography. ... 

Protopine and allocryptopine have been isolated from Papaver rhoeas, and protopine from Corydalis caua," C. gigantea, C. marschalliana, C. remota, C. rosea, and C. vaginans. The effect of protopine on induced cardiac arrhythmias has been studied." ... 

Rhoeadine and isorhoeagenine have been isolated from Papaver rhoeas L., as have smaller amounts of rhoeadine, isorhoeadine, rhoeagenine, and papaver-rubines A, C, D, and E rhoeadine has been obtained from P. tauricola. The LDso of rhoeadine has been determined, and five metabolites arising from its O-... 

Mecocyanin [ cyanidin 3-0- ophoroside, 3-(2-0-/ D-glucopyranosyl-j8-D-glucopyranosyloxy)-3, 4, 5,7-tetrahydroxyflavylium], CjvHjiOi, Mr 611.53, dark red crystals with a green luster. M. occurs in the fruits of sour cherry Prunus cerasus, Rosaceae) and in the flowers of the com poppy Papaver rhoeas, Papaver-aceae). 

R. a. are insoluble in water, chloroform, ether, poorly soluble in ethyl acetate and methylene chloride. Rhoeadine is weakly toxic [LD50 (rats i.p.) 530 mg/kg]. It effects dilatation of the pupils. Papaver rhoeas extracts are used as sedatives and expectorants, however, these uses are not attributed to the rhoeadine content. 

Ciral is a combination of flupyrsulfuron-methyl-sodium (33.3%) and metsulfuron-methyl (16.7%) for the control of Alopecurus myosuroides, Apera spica-venti, Poa annua and annual broadleaf weeds (except Galium aparine) such as Thlaspi arvense, Capsella hursa-pastoris, Galeopsis spp., Matricaria spp., Papaver rhoeas, Centaurea cyanus, Brassica napus, Viola arvensis, Lamium spp., Myosotis ar-... 

Budeyri N, Kazan D, Akbulut BS. Investigation of the antimicrobial effect of an alkaloid from Papaver rhoeas K. FEES J 2012 279(S1) 552. 

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