Magnoflorine and N,N-Dimethyllindcarpine

Stermitz, Frank R.; Castedo, Luís; Domı́nguez, Domingo

doi:10.1021/np50007a013

Cited by 14 publications

(9 citation statements)

References 6 publications

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“…The uv spectrum of the major morphinandienone alkaloid exhibited a reversible bathochromic shift with alkali, indicating that it was a phenolic compound. The presence in the ms of a molecular ion of m/e 327 was consistent with the alkaloid being salutaridine, isosalutaridine (7) or flavinantine (8). The nmr spectrum confirmed the presence of two methoxyl groups, an A-methyl group and four uncoupled aromatic protons with signals between 6.32 and 6.93.…”

Section: Resultsmentioning

confidence: 59%

“…As indicated previously, biogenetic speculation would infer that reticuline, the precursor of magnoflorine, would also yield the morphinandienone isosalutaridine (7) instead of flavinantine (8) and the proaporphine glaziovine (5) instead of Nmethylcrotonosine (6). However, it has been reported in the literature that flavinantine is probably biosynthesized from reticuline-type precursors by parapara phenolic oxidative coupling followed by demethylation and then re-methylation at the adjacent position in the morphinandienone A ring (16).…”

Section: Resultsmentioning

confidence: 85%

“…Tic Rf values of reference flavinantine and the Meconopsis alkaloid were identical (table 1), but isosalutaridine was not available for direct comparison. Confirmation of identification as flavinantine (8) was obobtained when it was shown that the O-acetyl derivative differed on tic from reference O-acetyl isosalutaridine. Flavinantine has been isolated previously from Croton flavescens.…”

Section: Resultsmentioning

confidence: 99%

“…The position has now been substantially clarified by a recent paper by Stermitz et al (8) in which magnoflorine (1) was prepared by selective O-demethylation of A'-methylisocorydine isolated from a Zanthoxylum species, and ', '-dimethyllindcarpine was prepared by A'-methylation of A'-methyllindcarpine isolated from a Glaucium species. The two quaternary alkaloids (1) and ( 2) separated readily by tic on silica gel, in longwave uv light ', '-dimethyllindcarpine did not show the characteristic intense blue fluorescence exhibited by magnoflorine, and the nmr were clearly different.…”

Section: Resultsmentioning

confidence: 99%

“…text of this paper has not been published until now because of subsequent serious doubts about the correct identification of magnoflorine. These doubts have now been removed because of the recent publication of an elegant piece of work by Stermitz et al (8) in which it was clearly demonstrated that magnoflorine (1) and its isomer T,T-dimethyllindcarpine (2) can readily be distinguished chromatographically and by nmr spectroscopy.…”

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confidence: 99%

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Meconopsis cambrica Alkaloids

Hemingway¹,

Phillipson²,

Verpoorte³

1981

J. Nat. Prod.

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The major alkaloid of the roots oí Meconopsis cámbrica was identified as the quaternary aporphine alkaloid ( + )-magnoflorine (1). The tertiary proaporphine alkaloids (-)-meeambrine (3), (-)-pronuciferine ( 4), (-)-.Y-methylerotonosine (6j, the morphinandienone alkaloids ( -)-flavinantine ( 8), (-)-amurine (9), the tetrahydroprotoberberine alkaloid (-)-mecambridine (10) and the benzophenanthridine alkaloid sanguinarine (11) were also isolated. The total tertiary alkaloid extracts of the roots, stems, flowers and fruits were shown to be qualitatively similar by tic.The genus Papaier has been investigated extensively for the presence of alkaloids in its many species but, in comparison, the closely related genus Meconopsis Vig. has received relatively little attention. Meconopsis is the second largest genus after Papaver in the tribe Papaverae and some 40 species, which are mainly indigenous to the Himalayas and China, are recognized. Protopine and sanguinarine have been reported from M. aculeata Royle, M. betonicifolia Franch., M. horridula Hook. f. and Thoms, M. latijolia Prain and M. ruáis Prain (1). In addition, M. ruáis yielded allocryptopine and magnoflorine (2), M. paniculada, coptisine (protoberberine-type) and M. dhwojii G. Taylor, sanguinarine (1). The only European representative of the genus, M. cámbrica Vig. (the Welsh Poppy), has yielded mecambrine (proaporphine-type) (3, 4), mecambroline (aporphinetype) (3, 4) and mecambridine (tetrahydroprotoberberine-type (3, ). The presence of sanguinarine has been indicated by paper chromatography (6), although another investigation failed to detect either this alkaloid or protopine or coptisine (3). It has been suggested, as a result of these previous investigations, that the alkaloidal-types found in the one European species of the genus are different from those of the Asiatic species (4). The abstract (7) of a short communication which was presented at the British Pharmaceutical Conference in 1975 reported briefly that magnoflorine was identified as the major alkaloid of the roots of M. cámbrica growing in the U.K.; the presence of other alkaloids was also reported. The full

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Section: Resultsmentioning

confidence: 59%

Section: Resultsmentioning

confidence: 85%

Section: Resultsmentioning

confidence: 99%

Section: Resultsmentioning

confidence: 99%

mentioning

confidence: 99%

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