Studies on the Alkaloids of Fumariaces Plants. XII. : Alkaloids of Corydalis platycarpa MAKINO (3) : On the Tertiary Base

Tani, Chiaki; Imanishi, Isamu; Nishijo, Juziro

doi:10.1248/yakushi1947.90.8_1028

Cited by 3 publications

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“…Typically, in TFA-J, C-5 appears at 25 ppm, C-6 at 56 ppm, C-8 at 59 ppm, 013 at 41 ppm and C-14 at 95 ppm, while the N-methyl carbon is near 46 ppm (131). (15) SOURCES: BERBERIDACEAE: Berberís (16) FUMARIACEAE: Corydalis (30,33,34,38,40,42,43,44,49,50,51,54,55,58,59,60,64,65,66,67,76,86,88,91,118,119,120,121) Dactylicapnos (61) Dicentra (38,52,56) Fumaria (1,29,47,57,68,69) P APA VE RACE AE: Argemone (2,25,26,114,115,116) Bocconia (103,122) Chelidonium (36,…”

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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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