Alpinigenine

Alkaloids from Turkish samples of Papaver orientale and P. pseudo-orientale.[Pubmed:17402043]

Planta Med. 1981 Nov;43(11):261-71.

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.[Pubmed:17401828]

Planta Med. 1981 Feb;41(2):105-18.

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.

High pressure liquid chromatographic determination of the five major alkaloids in Papaver somniferum L. and thebaine in Papaver bracteatum Lindl. capsular tissue.[Pubmed:447604]

J Assoc Off Anal Chem. 1979 Mar;62(2):310-4.

A high pressure liquid chromatographic isocratic procedure is described for determining and quantitating the 5 major alkaloids narcotine, papaverine, thebaine, codeine, and morphine in Papaver somniferum L. and thebaine in Papaver bracteatum Lindl. Other papaveraceous alkaloids, including salutaridine, oripavine, laudanosine, isothebaine, cryptopine, Alpinigenine, narceine, protopine, and gnoscopine, were also quantitated. The values for morphine, codeine, and thebaine in P. somniferum were in agreement within 5--9% with values obtained by the United Nations Narcotics Laboratory by other methods. In contrast to previously reported procedures, the advantage of this method is that no precolumn or other purification other than solvent extraction of the capsular tissue is necessary. Isocratic chromatography alone on a single column resolved the 5 major alkaloids.

Alkaloids of Papaver orientale L.[Pubmed:886446]

J Pharm Sci. 1977 Jul;66(7):1050-2.

According to the alkaloid profiles, five different chemotypes (A, B, C, D, and E) were classified in Papaver orientale L. with haploid chromosome number n = 14. Chemotype A had only oripavine; chemotype B contained oripavine and thebaine; chemotype C had isothebaine in addition to oripavine; chemotype D contained oripavine and Alpinigenine; and chemotype E had oripavine, thebaine, and Alpinigenine. In all chemotypes, oripavine was either the sole alkaloid or the single major alkaloid.

[Inhibition of the respiratory chain by the alkaloids berberine sulfate, alpinigenine, and tetrahydropalmatine].[Pubmed:189537]

Acta Biol Med Ger. 1976;35(7):1019-21.

The three alcaloids inhibited the NADH oxidase system of electron transfer particles from beef heart up to 90--100 percent. The concentrations of half-inhibition amounted to 50 muM for berberine sulphate and tetrahydropalmatine and 0.55 mM for Alpinigenine. All three compounds showed comparable inhibitions on the succinate-cytochrome c oxidoreductase system only at concentrations 20--25 times as high. The site of action may be the iron sulphur region of the complex I of the electron transfer system. The biological importance of this respiratory inhibitions should be taken into account.