CLI.—The alkaloids of ipecacuanha

Carr, Francis H.; Pyman, Frank Lee

doi:10.1039/ct9140501591

Cited by 24 publications

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“…For feeding purposes, labeled tyrosine, dopamine, Ndesacetylisoipecoside (15) and N-desacetylipecoside (16) were dissolved in H 2 O (1ml), labeled emetine (1), cephaeline (2) and psychotrine (3) were dissolved in H 2 O (1ml) containing DMSO (0.2ml). Labeled precursors were fed to young A. lamarckii Thw.…”

Section: Feeding Experimentsmentioning

confidence: 99%

“…Emetine (1), the well known antiamoebic 1 alkaloid and its relatives such as cephaeline (2), and psychotrine (3) were isolated from the dried rhizomes and roots of Cephaelis ipecacuanha 2 (Rubiaceae) and Alangium lamarckii Thw. (Alangiaceae) plant 3 .…”

Section: Introductionmentioning

confidence: 99%

“…The chemistry of these alkaloids has been reviewed 2 . The structure and stereochemistry of cephaeline, emetine and psychotrine as shown in 2, 1 and 3 respectively is well established.…”

Section: Introductionmentioning

confidence: 99%

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Late stages in the biosynthesis of ipecac alkaloids - cephaeline, emetine and psychotrine in Alangium lamarckii Thw. (Alangiaceae)

2012

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The bioconversion of tyrosine, dopamine, N- desacetylisoipecoside (15) and N- desacetylipecoside (16) into cephaeline (2), emetine (1), and psychotrine (3) into Alangium lamarckii Thw. (Alangiaceae) plant has been studied. Stereospecific incorporation of N- desacetylisoipecoside (15) into 1,2 and 3 has been demonstrated. Further it has been shown that reduction of C1’ – C2’ takes place after O-methylation of psychotrine (3). Feeding results further showed that cephaeline was poorly metabolized in the plants to form psychotrine (3) thus demonstrating that dehydrogenation of C1’ – C2’ does not take place. The efficient incorporation of cephaeline into emetine (1) further showed that O- methylation is the terminal step in the biosynthesis of emetine. Emetine (1) was poorly metabolized by the plants to form cephaeline (2) and psychotrine (3). The experiments thus demonstrated that dehydrogenation and O-demethylation of emetine (1) does not occur to give cephaeline (2) and psychotrine (3). Scientific World, Vol. 10, No. 10, July 2012 p24-28 DOI: http://dx.doi.org/10.3126/sw.v10i10.6857

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Section: Feeding Experimentsmentioning

confidence: 99%

Section: Introductionmentioning

confidence: 99%

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Late stages in the biosynthesis of ipecac alkaloids - cephaeline, emetine and psychotrine in Alangium lamarckii Thw. (Alangiaceae)

2012

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“…82 N-functionalities of alkaloids are methylated by HMeSO 4 under reflux in aqueous NaOH or in fusel oils. 83 NaMeSO 4 methylates NaNH 2 and acetamide when they are ground together dry (or in a small amount of benzene) between 180 and 200 C. 84 Heating, to 200 C, anhydrous salts of organic acids in the presence of HMeSO 4 or KMeSO 4 produces methyl esters. 85 Phenoxide is methylated in the presence of basic NaMeSO 4 and KMeSO 4 .…”

Section: Methylation Chemistrymentioning

confidence: 99%

One-step conversion of dipicolinic acid to its dimethyl ester using monomethyl sulfate salts for GC-MS detection of bacterial endospores

et al. 2011

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“…Non-toxic derivatives, at all events, appear to * See especially, on the chemistry of the ipecacuanha alkaloids, Carr and Pyman (1914) and Pyman (1917Pyman ( , 1918.…”

Section: |mentioning

confidence: 99%

The intestinal protozoa of man /

Dobell¹,

O'connor²

1921

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See Dobell (1920), where these observations are considered in detail. * The discovery was reported by Virchow in i860. See Dobell (1919) for further details.f This discovery is usually incorrectly attributed to Lambl (i860). Cf. Dobell (1919 a, pp. 8-9, and 71 et seq. ) where additional details will be found.(2) The Phylum Mastigophora consists of all those Protozoa which move, in their fully developed and typical condition, by means of whip-like filaments or flagella-familiar to all who have studied Euglena, or any other common flagellate.(3) The Phylum SPOROZOA contains a number of exclusively parasitic forms, which in their motile stages-when present-move without the aid of any special external locomotory organs. The several common species of Monocystis, parasitic in earthworms, supply familiar examples-with their slow, worm-like motions, performed by the body as a whole.(4) The Phylum Ciliophora contains all the Protozoa which move, in their typical active stages, by the agency of many little hair-like threads or cilia -exemplified in the familiar Paramecium and other common ciliates.Each of these Phyla contains a vast array of species, variously collected into genera, families, orders, and higher groups. It will be unnecessary, however, to discuss their classification in detail here, and we shall limit ourselves to a consideration of the systematic position of those species alone with which the present work is concerned. It will suffice to note the general grouping of our forms, and their more obvious relations to one another.The human intestine harbours protozoa belonging to all the four Phyla just enumerated. As these groups contain organisms as different * See especially Yorke, Carter, Mackinnon, Matthews, and Smith (1917), Smith (1919, 1919a), Dobell (1921).tSee Dobell (1921). % Among more recent contributions to this subject the reader may be referred to the following : Galliard and Brumpt (1912), Paviot and Garin (1913), Landouzy and Debrd (1914), Bloch (1916) -French cases; Kuenen (1918) -Dutch cases; Fischer (1920) -German cases; Yakimoff (1917)-Russian cases; Kofoid, Kornhauser, and Plate (1919), Cort and McDonald (1919) -United States cases. There are also numerous other works dealing with the occurrence of intestinal protozoa in the inhabitants of temperate climates, but it would lead us too far to discuss-or even to attempt to citeall of them. See also the papers on French cases of Balantidiosis cited on p. 119 infra.* Numerous references will be found in the Tropical Diseases Bulletin. The reader interested in this subject may be referred to the following recent works, which will also supply him with numerous further references to the immense literature dealing with the incidence of intestinal protozoal infections :

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CLI.—The alkaloids of ipecacuanha

Cited by 24 publications

References 0 publications

Late stages in the biosynthesis of ipecac alkaloids - cephaeline, emetine and psychotrine in Alangium lamarckii Thw. (Alangiaceae)

Late stages in the biosynthesis of ipecac alkaloids - cephaeline, emetine and psychotrine in Alangium lamarckii Thw. (Alangiaceae)

One-step conversion of dipicolinic acid to its dimethyl ester using monomethyl sulfate salts for GC-MS detection of bacterial endospores

The intestinal protozoa of man /

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