Protopine genera

Table 5 summarizes results of protopine alkaloid isolation studies. The structures assigned to the two alkaloids isolated from both Fumaria parviflora and F. vaillantii are of immediate interest and concern.221 The detailed study of the Papaver genus is of general chemotaxonomic interest.69... 

Another possibility might be that the rhoeadine alkaloids arise from protopine alkaloids (see Scheme 20) which are always found present in the plants of the genus Papaver. 

These alkaloids, chelidonine, homochelidonine, methoxychelidonine, chelerythrine, and sanguinarine, are found in the Chelidonieae tribe of the Papaveraceae family as well as in the genus Glaudum of the same family (tribe-—Papavereae). They are always accompanied by protopine, and sometimes by allocryptopine and the protoberberines. 

The species of the genus Glaucium Toum. are characterized by the presence of aporphine and protopine alkaloids in addition to protoberberines and benzophe-nanthridines (Tables XVII and XVIII). Platonova et al. (110) isolated corydine (136) from G. squamigerum as the major alkaloid in addition to a smaller amount of protopine (309) and allocryptopine (310). In G. oxylobum, the major alkaloid was corydine together with protopine and allocryptopine (107). In contrast, Slavik et al. (108) isolated allocryptopine (310) and protopine (303) as the... 

The genus Roemeria Medic, comprises approximately 10 species, of which only R. hybrida (L.) DC. and R. refracta (Stev.) DC. have been studied for their alkaloid content (Tables XIX and XX). From R. hybrida, Platonova et al. (110) isolated protopine (309) as the major alkaloid together with roemeridine. In contrast to Soviet authors, Slavik et al. (Ill) were not able to detect the presence of protopine (309) in their plant material. They isolated roemeridine as the main component. In two herbal samples of R. hybrida from Iraq, the major alkaloid was roehybrine (103) (57). 

The only representative of the genus Hunnemannia A. Juss., which is closely related to the genera Eschscholtzia, Dendromecon, and Petromecon, is Hunnemannia fumariaefolia Sweet, native to Central America. In the aerial part of this plant, the major alkaloid is hunnemanine (312) (Tables XXXVIII and XXXIX) and in the roots, protopine (309), hunnemanine, and allocryptopine (310). Cyclanoline (245) represents the main component of the quaternary alkaloid fraction of the aerial part and the roots. 

Almost all of the studied plants have been found to contain protoberberines, protopines, and phthalideisoquinolines. The occurrence of aporphines and ben-zophenanthridines is frequent. The secoberbines have been isolated from C. incisa and C. ochotensis. The cularines, which are characteristic of some plants of the genus Corydalis, are also found in the genera Dicentra and Sarcocapnos. 

Fumaria chemically resembles Corydalis. Similarly, the genus Fumaria also contains protoberberines, protopines, and phthalideisoquinolines, and more frequently, secophthalideisoquinolines and spirobenzylisoquinolines. They also yield indenobenzazepines, which cannot be demonstrated in the genus Corydalis (Table LVI), but no aporphines and cularines, which have been isolated from the plants of the genus Corydalis. 

Only in one species of the genus Adlumia Rafin. have protopines and phtha-lideisoquinolines been found (Tables LXI and LXII). 

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. ... 

The following groups of alkaloids occur in the plant family of the Papaveraceae benzylisoquinoline, cularine, aporphine, proaporphine, morphine, protoberberine, protopine, narceine, benzophenanthridine, phthalide-isoquinoline, rhoeadine, papaverrubine, pavine, isopavine and ochotensimine. Many of these alkaloid groups are formed by one genus only, whereas others occur in many genera and even in plants of other families. Alkaloids of all these groups must thus be taken into considera-... 

Protopine is the second most cited alkaloid in this review, with 85 citations (11.5%), from plants of four different families and 16 genera. The genus Corydalis with 22 citations (25.9%) has the largest contribution, followed by Papaver with 19 (22.4%) and Fumaria with 11 citations (12.9%). 

Plants of the subfamily Hypecoideae differ chemotaxonomically from the plants of the subfamily Papaveroideae. Species of the genus Hypecoum contain secoberbine alkaloids (37-39) in addition to protopine (3), protoberberine (5) and benzophenanthridine (6) alkaloids. The presence of secoberbines (37-39) is indicative of a close relationship between Hypecoum and some species of Fumariaceae. 

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