Papaver orientale

The Apomorphine-derived alkaloid PO-3 (129) was isolated as violet needles after crystallization from acetone and ether from Papaver orientale (66MI2), but was not found in the green solutions of autoxidized apomorhine hydrochloride (62M941, 68HCA683) (Scheme 51). No anion was detected by elemental analysis. The pA"a of PO-3 is 3.88 0.02 in 50% ethanol. The IR spectrum displays no carbonyl absorption between 1650 and 1700 cm (69MI2). The UV absorption maxima of PO-3 are in agreement with the formulation of a mesomeric betaine [T-max (EtOH) = 310... 

Papaver atlanticum (Papaveraceae) cccc 51,2232 86 Papaver bracteatum (Papaveraceae) pm 32, 60 77 Papaver nudicaule (Papaveraceae) zpf 114,361 84 Papaver orientale (Papaveraceae) jps 66,1050 77 Papaver pseudo-orientale (Papaveraceae) paz 13,50 77 Papaver setigerum (Papaveraceae) zpf 114,361 84 Papaver somniferum (Papaveraceae) zpf 114,361 84... 

Glaucium flavum (Papaveraceae) phy 27,1021 88 Glaucium spp. (Papaveraceae) jnp 61,1564 98 Papaver bracteatum (Papaveraceae) cccc 50,1215 85 Papaver fugax (Papaveraceae) jsiri 7,263 96 Papaver orientale (Papaveraceae) book 4 Papaver pseudo-orientale (Papaveraceae) cccc 51,1752 86 Papaver somniferum (Papaveraceae) book 4 Papaver triniifolium (Papaveraceae) pm 49,43 83 Papaver spp. (Papaveraceae) dsa 7,93 83 Sarcocapnos crassifolia (Papaveraceae) phy 30,1175 91 Sarcocapnos saetabensis (Papaveraceae) phy 30,1175 91... 

A minor constituent of P. somniferum is the aporphine alkaloid isoboldine (Figure 6.58). Other species of poppy, e.g. Papaver orientale and P. pseudoorientale, are known to synthesize aporphine alkaloids as principal constituents rather than morphinan structures. (Aj-Isoboldinc is readily appreciated to be the product of oxidative coupling of (5)-reticuline, coupling ortho to the phenol group in the tetrahydroisoquinoline, and para to the phenol of the benzyl substituent... 

In 1935 an alkaloid named oripavine having the composition Ci8H2i03N was isolated from Papaver orientale [124] and subsequently from Papaver bracteatum [125], It was shown to contain one —OMe, one —NMo, and one phenolic —OH group [124], and was eventually converted to thebaine [v] by methylation with diazomethane [126] and is in fact 3-0-desmethylthebaine [xxxvn] it bears the same relationship to morphine as thebaine does to codeine. On boiling with... 

During the period of growth of the oriental poppy, Papaver orientale, the plant contains appreciable amounts of thebaine, but during late fall, after ripening and dying of the aerial plant, little, if any, of this alkaloid is to be found, but at this time an optically active base, isomeric with thebaine, may be isolated from the root of the poppy. This base, called isothebaine, was first isolated by Gadamer [1-2] as an unidentified phenolic alkaloid and subsequently examined by Klee [3]. It has also been shown to be present in Papaver bracteatum [4],... 

Isothebaine, C19H21O3N, was first isolated from Papaver orientale L. by Gadamer and Kies (79) and properly characterized and further examined by Klee (80), who showed that the plant during active grow th contained almost exclusively thebaine but as it reached maturity the plant, and particularly the roots of it, contained very little thebaine but mostly isothebaine. It was postulated that the plant converted the thebaine into isothebaine. 

Papaver Alkaloids.—Biosynthesis of benzylisoquinoline alkaloids involves the amino-acid dopa, which is in part implicated through decarboxylation to dopamine. The presence of L-dopa decarboxylase in Papaver orientale latex has recently been demonstrated. ... 

Traditional use Juice from the petals is used as a drink to treat heatstroke (in children) and as a rinse for eye ailments. The dried petals of related species, Papaver rhoeas, Papaver orientale, and Papaver bracteatum, are used to prepare a tea to treat coughs (Khahnatov 1964 Seredin and Sokolov 1969). 

A new glycosidic benzylisoquinollne base Is veronamlne, where the carbohydrate moiety Is rhamnose. The oxoaporphine alkaloid lirlodenlne has shown significant cytotoxic activity, and the first quaternary oxoaporphine alkaloid has been found in Papaver orientale. An aporphine and an oxoaporphine oxygenated at C-4 are steporphlne and Inenine respectively, ... 

Saxton JE (1971-1975) The alkaloids, vols 1-5. Chem Soc, Burlington House, London Shaflee A, Lalezari I, Nasseri-Nouri P, Asgharian R (1975) Alkaloids of Papaver orientale and P. pseudo-orientale. J Pharm Sci 64 1570-1572 Shafiee A, Lalezari I, Assadi F, Khalafi F (1977) J Pharm Sci 66 1050 Shamma M (1972) The isoquinoline alkaloids. Academic Press, London New York Shamma M, Moniot JL (1978) Isoquinoline alkaloids research, 1972-1977. Plenum Press, New York London... 

The importance of a particular 0-methylation pattern in deciding the product of coupling is illustrated in an excellent way by the results of a study on the biosynthesis of thebaine (35) and isothebaine (39) in Papaver orientale. Thebaine (35) is formed via reticuline (25) but not via orientaline (36), whereas the reverse is true for isothebaine (39) it is derived exclusively via orientaline (36) (Battersby et al. 1965) (Fig. 7). 

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