Bocconia frutescens

Protopine has been isolated from Bocconia frutescens,110 Fumaria judaica,111 F. schleicheri,112 and Papaver bracteatum,146 cryptopine from F. schleicheri,112 and allocryptopine from B. frutescens110 and Zanthoxylum nitidum.141 The protopine ring-system has been prepared from tetrahydrobenzindenoazepines (75) by photo-oxidation to the amides (76) followed by reduction with lithium aluminium hydride and re-oxidation with manganese dioxide.148-150 The tetrahydrobenzindenoazepines have been prepared from A-chloroacetyl-/ -phenylethylamines (73) by cyclization to the lactam (74) followed by reaction with a benzyl bromide and phosphorus oxychloride. -Protopine (77 R R2 — CH2)148 and fagarine II (77 R1 = R2 = Me)149 have been synthesized in this way. 

Rhoeadine has been isolated from Bocconia frutescens,110 alpinigenine from Papaver bracteatum,146 and rhoeadine, rhoeagenine, glaucamine, glaudine, epi-glaudine, oreodine, and oreogenine from P. tauricola.108... 

Reports have appeared on t.l.c. methods of detection of benzophenanthridine alkaloids in Bocconia frutescens, Macleaya microcarpa, and M. cordata and in Fumaria capreolata. A colorimetric method of determining the alkaloids in B. cordata has been described. ... 

Formerly, rhoeadine and papaverrubine alkaloids were known to occur only in the plants of the genus Papaver. Recently, Slavik et al. have shown that rhoeadine and papaverrubine E are present in Bocconia frutescens and papaverrubine D in Meconopsis betonicifolia, M. horridula, M. napaulensis, M. paniculata, M. robusta, M. rudis, and M. sinuata (33, 50). The genus Meconopsis is botanically closely related to the genus Papaver, a relation thus confirmed chemotaxonomically (see structures 152-154 in Table V). 

Slavik and Slavikova showed that the content of alkaloids in Glaucium fimbrilligerum is closely related to the species G. elegans, G. oxylobum, and G. squamigerum (205). (—)-Isocorypalmin (58r) was found not only in O. fimbrilligerum but in Bocconia frutescens and Roemeria hybrida (see Table II). Until now it was only isolated from P. somniferum as a minor component. This alkaloid is, however, commonly found in the botanically and biochemically closely related tribe Fumarieae. 

Rhoeadine and papaverrubine (norrhoeadine) alkaloids which were previously believed to occur only within the genus Papaver have now been found to be present in two other Papaveraceae genera, namely Bocconia and Meconopsis. In Bocconia frutescens L. rhoeadine alkaloids accompany a variety of protopine, protoberberine, and benzophenanthridine bases. ... 

Notholirion hyacinthium, Veratrum stenophyllum (Liliaceae), Solanum chacoense, S. nigrum, S. tuberosum (potato) (Solanaceae) [tuber] Argemone mexicana, Bocconia arborea, B.frutescens, Chelidonium majus, Eschscholfa californica, Glaucium flamm, Sanguinaria canadensis (Papaveraceae), fanthoxylum americanum (Rutaceae)... 

The genus Bocconia of the tribe Chelidonieae comprises some 10 species which are native to tropical and subtropical areas of Central and South America. Bocconia, which is closely related to the East Asian germs Macleaya, does not appear to contain alkaloids which are taxonomicaUy significant although it may be noted that rhoeadine (18) and papaverrubine E have been isolated from B. frutescens L. (Slavik and Slavikova 1975). 

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