Alkaloids of the Papaveraceae. LII. Alkaloids from some plant species of the section Orthorhoeades

Němečková, A.; Šantavý, F.; Walterová, Daniela

doi:10.1135/cccc19701733

Cited by 14 publications

(3 citation statements)

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“…There have been numerous investigations into the alkaloidal constituents of P. rhoeas [2,3] and over thirty alkaloids have been isolated from this one species. It appears from the chemical literature that P. rhoeas is variable in its contained alkaloids and that different chemotypes exist [4]. In previous studies on Egyptian P. rhoeas, the macroscopic and microscopic characters of the plant have been reported in some detail [5] and rhoeadine has been tentatively identified (TLC only) as one of the twelve alkaloids detected by TLC [6].…”

Section: Introductionmentioning

confidence: 99%

Alkaloids from Egyptian Papaver rhoeas

El-Masry¹,

El–Ghaz;ooly²,

Omar³

et al. 1981

Planta Med

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Section: Introductionmentioning

confidence: 99%

Alkaloids from Egyptian Papaver rhoeas

El-Masry¹,

El–Ghaz;ooly²,

Omar³

et al. 1981

Planta Med

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“…MP: 222-223°(CHClrEtOH) (99) UV: (MeOH) 234 (4.20), 286 (3.95) (99) »»C NMR: (73) SOURCES: PAPAVERACEAE: Argemone (109, 114, 115) Glaucium (97) Papaver (7, 13, 22, 70, 71,75,89,90) …”

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The Protopine Alkaloids

Guinaudeau¹,

Shamma²

1982

J. Nat. Prod.

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Sixteen naturally occurring protopines are known. The prototype for these bases is the widely distributed alkaloid protopine (1) wrhose numbering system is indicated in expression 1. The listing for the occurrence of this alkaloid as well as of allocryptopine (2) emphasizes the more recent findings. For an older listing of the occurrence of protopine (1) and allocryptopine (2) in plants, the reader should refer to H.-G. Boit's Ergebnisse der Alkaloid-Chemie Bis 1960, Akademie Verlag, Berlin (1961), pp. 349-351. Protopines are optically inactive, except in the case of C-13 substitution. The absolute configuration of the 13-methylated base corycavine (13) has been recently determined by correlation with a 13-methylated berbine of established absolute configuration (37).The alkaloid oreophiline is not a protopine base as long believed, but is instead a berbine (81).Among the Rutaceae, the genera Fagara and Zanthoxylum are generally considered to be identical. Neverthless, in the present listing, they have been kept apart to reflect the botanical names cited in the literature. It will be noted also that pseudoprotopine (9) and fagarine II (10) are the only two protopines substituted at C-10,11 rather than at the more common C-9,10 sites. Significantly, both of these alkaloids are found only among the Rutaceae.Uv wave lengths are in nm, and ir frequencies in cm-1. The solvent is always given whenever it has been indicated in the original literature. nmr chemical shifts are in CDCh solution unless indicated otherwise. In instances where chemical shift assignments were changed from those made in the original literature, this has been indicated with a double asterisk (**) as a superscript immediately after the appropriate reference. The H-l absorption in the protopines is found further downfield than that due to H-4 because of deshielding by the carbonyl function (5). The C-5 methylene protons are found near 52.6 4 5

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“…coptisine. protopine and sanguinarine (7)(8)(9)(10)(11). In view of the variable alkaloid constituents reported from several species of the section Papaver, the possibility of chemical races of it would be of interest to investigate further samples of P. lacerum from other parts of Turkey and Soviet Armenia for the presence of alkaloids.…”

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confidence: 99%