On alkaloids from the aerial parts of three Eschscholtzia species

Abstract

In the aerial parts of Eschscholtzia californica CHAM., E. dougla.lii (HOOK. et ARN.) WALP. and E. g/auca GREENE the main alkaloidal component is the quaternary base californidine. Eschscholtzine, allocryptopine, and protopine belong among the dominant tertiary alkaloids, which are accompanied by a small amount of N-methyllaurotetanine and the quaternary benzophenanthridines (sanguinarine, chelerythrine, chelirubine, chelilutine, and macarpine). The pavinane alkaloids isonorargemonine, caryachine, norargemonine, and bisnorargemonine and the aporphine alkaloids corydine and isocorydine were isolated from the aerial part of the E. douglasii species for the first time. These alkaloids were also detected in E. californica and E. glauca. Corytuberine was also isolated from all three species. From the fraction of quaternary alkaloids after conversion to iodides, in addition to californidine, escholamidine iodide was isolated from E. californica and E. douglasii species. From E. douglasii N-methyIcaryachininium iodide and from E. glauca magnoflorine iodide were also isolated. The presence of a small amount of the mentioned quaternary alkaloids, as well as traces of escholamine were also detectable in all three species.

HPLC Analysis of the main alkaloids from Eschscholtzia Californica cham

“…Sanguinarine (6) and chelerythrine (7) are the dominant components of a complicated * Author to whom corrcspondencc should bc addressed mixture of quaternary bases with a lesser amount of escholidine, magnoflorine (esholine), escholinine and the N-methyl salt of (-)-u-canadine (Gertig, 1965a, c;Slavik and Slavikova, 1971;Slavik et al 1970). The main alkaloid of the aerial parts is the quaternary base californidine (5) (Gertig, 19653;Slavik and Slavikova, 1986). The dominant components are the phenolic tertiary base, N-methyllaurotetanine (lauroscholtzine) (1) and the tertiary non-phenolic bases eschscholtzine (4), protopine and allocryptopine Slavik and Slavikova, 1986).…”

“…The main alkaloid of the aerial parts is the quaternary base californidine (5) (Gertig, 19653;Slavik and Slavikova, 1986). The dominant components are the phenolic tertiary base, N-methyllaurotetanine (lauroscholtzine) (1) and the tertiary non-phenolic bases eschscholtzine (4), protopine and allocryptopine Slavik and Slavikova, 1986). The pavine alkaloids, eschscholtzine and its N-methyl derivative (californidine), are the typical components of the aerial parts although the former is not found in the roots (Gertig, 1965b;Manske et u f .…”

Identification of Pavinane Alkaloids in the Genera Argemone and Eschscholzia by GC-MS

“…(Papaveraceae) includes a large number of taxa. Taxonomically, this genus is a heterogeneous group, the species representing a very plastic and polytypical group with a large number of ecotypes [1]. The plants are annual to perennial and are native to California and adjacent regions of North America.…”

“…The biological activity of Argemone and Eschscholzia species is mostly associated with the presence of isoquinoline alkaloids. Both genera produce a wide range of pavinane type isoquinoline alkaloids [1,[3][4][5][6], some of which have been isolated and their NMR data made available in the literature [3,6]. Nevertheless, details of their EI mass spectra, which can be used for fast identification of these compounds in crude plant extracts, have not been reported yet.…”

“…All alkaloidal extracts were dominated by either pavine or protopine alkaloids that had already been isolated from selected species [1,5,[7][8][9]. Pavines are derived biogenetically from either the tetrahydrobenzylisoquinoline alkaloid (+)-reticuline or a close analogue thereof [10].…”