Two new benzylisoquinoline alkaloids from Papaver triniifolium.

From the aerial parts of Papaver triniifolium Boiss. (Papaveraceae) collected from Erzincan (Eastern Anatolia), two new benzylisoquinoline alkaloids, miltanthoridine and miltanthoridinone were isolated. Their structures were established through the use of UV, EIMS, and NMR techniques.

A new dehydroaporphine alkaloid from Papaver fugax.

A new dehydroaporphine alkaloid (-)-6a,7-dehydrofloripavidine has been isolated from the aerial parts of Papaver fugax Poir. (Papaveraceae) collected from Erzurum (Eastern Anatolia). (-)-Floripavidine (aporphine) and (-)-mecambrine (proaporphine) were isolated as major alkaloids. Other bases present were (+)-salutaridine (promorphinane) and argentinine (phenanthrene). The presence of argentinine has been shown for the first time in the Papaveraceae.

Isolation of triniifoline, miltanthaline and some medicinally important alkaloids from Papaver triniifolium.

New alkaloids, (+)-triniifoline, (+)-O-ethyltriniifoline (rhoeadine type), and (+)-miltanthaline (benzylisoquinoline type) have been isolated from aerial parts of Papaver triniifolium Boiss, (Papaveraceae). The major alkaloids were medicinally important (-)-alpha-narcotine and papaverine together with (-)-mecambrine in the species whereas narceine and (-)-N-methylcrotonosine were minor alkaloids. The known (-)-alpha-narcotine, narceine and (-)-N-methylcrotonosine have been isolated for the first time from P. triniifolium.

Alkaloids from Papaver triniifolium of Turkish Origin1.

The major alkaloids of PAPAVER TRINIIFOLIUM collected in two different parts of Anatolia have proved to be of the aporphine, morphinane and rhoeadine types. The two collections possessed different major alkaloids and the existence of chemical strains is indicated. In addition to the aporphine-(floripavidine), the morphinandienone-(amurine and salutaridine), benzylisoquinoline-(papaverine), proaporphine-(mecambrine) and tetrahydroprotoberberine-(sinactine, scoulerine and cheilanthifoline) type alkaloids have been isolated as minor alkaloids.

Alkaloids from Papaver cylindricum.

The major alkaloids obtained from Papaver cylindricum Cullen were oripavine, narcotine, thebaine and rhoeadine. Floripavidine, papaverine, salutaridine, armepavine, N-methylasimilobine, scoulerine and cheilanthifoline were obtained as minor alkaloids. There have been no previous reports of alkaloids from P. cylindricum.

Alkaloids from Turkish samples of Papaver orientale and P. pseudo-orientale.

The alkaloids obtained from the capsules of five different collections of wild P. orientale and sixteen different collections of wild P. pseudo-orientale have been investigated and the chromosome numbers of some of the samples determined. Oripavine was the major alkaloid obtained from four of the P. orientale collections, two of which had a diploid chromosome number of 28. These four samples contained isothebaine and alpinigenine as minor alkaloids whereas two contained mecambridine and orientalidine and the other two contained thebaine and salutaridine. The remaining sample of P. orientale contained mecambridine as the major alkaloid and also some orientalidine. Thirteen of the sixteen samples of P. pseudo-orientale contained isothebaine, mecambridine and orientalidine as their major alkaloids with thebaine and salutaridine as minor alkaloids. Alpinigenine was detected in three samples. The diploid chromosome number of four of the thirteen samples was determined as 42. Two samples of P. pseudo-orientale contained salutaridine and thebaine as major alkaloids and had a diploid chromosome number of 14 whereas the remaining sample yielded salutaridine as the major alkaloid with isothebaine, mecambridine and orientalidine as minor alkaloids and a diploid chromosome number of 28.

Alkaloids from Papaver armeniacum, P. fugax and P. tauricola.

Species from the section Miltantha are reviewed in the context of their contained alkaloids. Thebaine was isolated as the major alkaloid from a sample of P. fugax together with narcotine, pronuciferine, alpinigenine, O-ethylalpinigenine, amurensinine, N-methyl-crotonosine, armepavine, isocorydine and salutaridine as minor alkaloids. A second sample of P. fugax contained glaucamine and glaudine as major alkaloids with rhoeadine, oreogenine, oreodine and O-ethyl-glaucamine as minor alkaloids. Pronuciferine and armepavine were isolated as the major alkaloids from a sample of P. tauricola with narcotine, roemerine, nuciferine, nantenine and protopine as minor alkaloids. Another sample of P. tauricola yielded pronuciferine and mecambrine as major alkaloids with armepavine, lirinidine, thebaine and cryptopine as minor alkaloids. A sample of P. armeniacum contained rhoeadine and rhoeagenine as major alkaloids with lirinidine, cryptopine, glaudine and O-ethylrhoeagenine as minor alkaloids. Some 25 alkaloids representing 9 different alkaloidal-types were obtained from extracts of the three Miltantha species. The results show that at least three different chemical races of P. fugax and P. armeniacum exist in which either 1-benzyltetrahydroisoquinoline-, proaporphine-, aporphine- or morphinane- or rhoeadine- types are the major alkaloids. There are at least two different chemical strains of P. tauricola which contain either 1-beuzyltetrahydroisoquinoline-, proaporphine-, aporphine- or rhoeadine- types as the major alkaloids.