Papaver orientate

Pansy. See Viola Papaver, 160 Papaver alpinum, 160 Papaver nudicaule, 160 Papaver orientate, 160 Parasitic plants, 343,344,354-55 Parasitoids, 258 Parsley, 160... 

From the root and whole plant of Papaver orientate L., Papaveraceae. collected in late autumn. Isoln Gadamer, Arch, Pharm. 249, 39 (1911). Structure Bentley. Blues, J. Chem. Soc. 1956, 1732 Bentley, Dyke, J. Org. Chem, 22,429 (1957). Synthesis of di-form Battersby, Brown, Proc. Chem. Soc. (London) 1964, 85 H. Hara etal.. Chem. pharm. Bull 29, 1083 (1981), Synthesis of natural and racemic forms Battersby et of.. J, Chem. Soc. 1965, 4550. Biosyn -thesis eidem, Chem. Commun. 1965, 230,... 

Aristolochiaceae, Euphorbiaceae, Fabaceae, Lilia-ceae, Magnoliaceae, Menispermaceae, Papaveraceae, Ranunculaceae). Anonaine is found mainly in Annona reticulata (Annonaceae), bulbocapnine in Corydalis cava (Fumariaceae), isothebaine especially in Papaver orientate and P. bracteatum, magnoflorine in Magnolia obovata (Magnoliaceae) and Aquilegia hybrida (Ranunculaceae), and roemerine in Roemeria refracta (Papaveraceae) and Nelumbo nucifera (Nelumbona-ceae). A. a. are soluble in chloroform, alcohol, and ether, poorly soluble in water. 

Cherylline, an unusual tetrahydroisoqulnoline alkaloid, was isolated from Crinum powellii.23 Structure 16 was assigned to it from spectral and degradative evidence and was confirmed by an unambiguous synthesis.2 The structures of two unnamed pseudoprotoberberine alkaloids from Papaver orientals have been assigned as J7 and 18.2 Cancentrine, from Dicentra canadensis. is a new type of dimeric benzylisoquinoline... 

Although the mechanisms above were postulated before compounds resembling the proposed intermediates were known, compounds such as orientalinone (50) were later isolated. Both (- )-orientaline (29) and (+ )-orientalinone (50) (a proaporphine alkaloid) serve as precursors for isothebaine (49) in Papaver orientate (Fig, 32.12) (Geissman and Grout, 1969). 

In an important series of experiments involving and doubly labeled precursors, Wilson and Coscia have shown that in Papaver orientate L., dopa may be metabolized in at least two ways to yield dopamine and 3,4-dihydroxy-phenylpyruvic acid. Decarboxylation of dopa to yield dopamine is actually favored over transamination to the substituted pyruvic acid. Norlaudanosoline carboxylic acid is the first tetrahydrobenzylisoquinoline alkaloid to be formed, and it is readily converted to norlaudanosoline through the presumed intermediacy of an imine (see Scheme 2.10). ... 

A minor constituent of P. somniferum is the aporphine alkaloid isoboldine. Other species of poppy, e.g., Papaver orientate and P. pseudoorientale, are known to synthesize aporphine alkaloids as principal constituents rather than morphinan structures. (5)-lsoboldine 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. Some... 

Roberts MF, McCarthay D, Kutchan TM, Coscia CJ (1983) Localization of enzymes and alkaloi-dal metabolites in Papaver latex. Arch Biochem Biophys 222 599-609 Schuchmann R, Wellmann E (1983) Somatic embryogenesis of tissue cultures of Papaver somniferum and Papaver orientate and its relationship to alkaloid and lipid metabolism. Plant Cell Rep 2 88-91... 

Roberts MF, Antoun MD (1978) The relationship between L-DOPA decarboxylase in the latex of Papaver somniferum and alkaloid formation. Ph3rtochemistry 17 1083-1087 Roberts MF, McCarthy D, Kutchan TM, Coscia CJ (1983) Localization of enzyme and alkaloidal metabolites in Papaver latex. Arch Biochem Biophys 222 599-609 Rueffer M, El-Shagi H, Nagakura N, Zenk MH (1981) (S)-Norlaudanosoline synthetase the first enzyme in the benzylisoquinoline biosynthetic pathway. FEBS Lett 129 5-9 Sasse F, Backs-Hiisemann D, Barz W (1979) Isolation and characterization of vacuoles from cell suspension cultures of Daucus carota. Z Naturforsch 34 848-853 Schuchmann R, Wellmann E (1983) Somatic embryogenesis of tissue cultures of Papaver somniferum and Papaver orientate and its relationship to alkaloid and lipid metabolism. Plant Cell Rep 2 88-91... 

---