Papaver section Miltantha

The alkaloids of the arm epavine type were detected in the genus Papaver (section Miltantha) and in the form of a glycoside (latericine) in the sections Orthorhoeades and Pilosa. From this it follows that only these sections elaborate enzymes which are ahle to cleave the phenol group from the C-3 atom or to use tyrosine for the biosynthesis of armepavine alkaloids. 

Plants of Papaver Section Miltantha and Their Alkaloids... 

Figure 1.19. Tyrosine-derived alkaloids in the Rhoeadales, Berberidales, and Ranales. The first compound synthesized is norlaudanosoline, and nine distinct types of alkaloids are encountered either in restricted taxa or widely distributed A—salutaridine B— morphine pathway restricted to Papaver section Mecones C—isothebaine pathway, characteristic of Papaver section Macrantha D—Papaver section Miltantha E—Papaver section Scapiflora F-encountered in Chelidonium (Papaveraceae-Rhoeadales) and Berberis G—characteristic for Papaver section Orthoroedes, the Corydalis dicentra and Chelidonium spp. H—cryptowoline I—Papaver section Scapiflora, genus Escholtzia, and Argemone J—Papaver sections Orthoroedes and Pilosa, Data are compiled from publications by Stermitz (1968, 1974), Santavy (1966), Santavy et al. (1965, 1966) Slavik (1955), Slavik et al. (1963), Pfeifer (1962), and Tetenyi and co-workers (1961, 1965, 1967, 1968), Bandoni, et al. (1972, 1975). The reaction pathways are according to Barton and Widdowson (1972). Only pathways A, B, and C are shown in detail the others are only suggestions. The pathways leading to the dimeric (bis) alkaloids are not shown.

The promorphinane alkaloids were found in the sections Miltantha, Pilosa, Macrantha, and Scapiflora, and thebaine in some plants of the sections Orthorhoeades, Mecones, Pilosa, and Macrantha (genus Papaver). Codeine and morphine could be detected only in the plants... 

XII) (56-60). The alkaloid armepavine was not found in any other section of the genus Papaver, which makes it a chemotaxonomic characteristic of the section Miltantha. 

The investigation of the herbarium samples from Iraq was carried out (65). Papaver acrochaetum yielded rhoeagenine 404) as the major alkaloid. The major alkaloids of P. curviscapum were protopine (309) and allocryptopine (310). The major alkaloid of Iraqi P. persicum and of P. armeniacum was identified as the glycosidic alkaloid floripavidine (119), which had been first reported from P. floribundum. For the infraspecific variation of the alkaloids of the section Miltantha, see also Ref. 64. 

Interesting is the finding of ( + )-armepavine (12) in A. turnerae. This is the only finding of a (-l-)-enantiomer of armepavine in the Papaveraceae. The presence of the (—)-enantiomer is characteristic of the section Miltantha (genus Papaver). 

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