Alkaloids angostura bark

Galipoline, C19H19O3N. A process for the extraction and separation of the angostura bark alkaloids was described by Spath and Eberstaller,i and from the phenolic bases obtained Spath and Papaioanou isolated this alkaloid. It crystallises from water, has m.p. 193°, contains two methoxyl groups, and on methylation by diazomethane yields galipine. 

From a spurious angostura bark, Troger isolated an unnamed alkaloid, ( jjHjgOjNj, m.p. 167°, soluble in alkali or acid and giving a a ystallinc perchlorate and methiodide. 

Esenbeckia febrifuga Juss. Brazilian angostura bark (cf., p. 415) contains 3-9 per cent, of alkaloids. (Hartwich and Gamper, Arch. Pharm., 1900, 238, 568.)... 

Alkaloids containing quinoline as the principal nucleus include anemonine from Anemone tha-lietroides, galipine from Angostura bark (Galipea officinalis), and the cinchona alkaloids, quinine, quinidine, cinchonine, and cinchonidine (Figure 11.8). 

A number of simple quinolines and quinolones have been isolated from various rutaceous plants, e.g., from angostura bark (Volume III, p. 80) and from Lunasia amara Blanco (Volume VII, p. 241 this chapter Section IV,A). The leaves of Haplophyllum dubium Eug. Kor (15, 16) contain dubamine (mp 96°-97°) which has been identified (17) as 2-(3,4-methylenedioxyphenyl)quinoline (I). Ruta graveolens L. contains, in addition to furoquinolines, the alkaloids graveoline (mp 205°) (18,19), and graveolinine (mp 115°-116°) (20), the latter (II) is also found in L. amara, and the former is the related l-methyl-4-quinolone (III). 

All the principal alkaloids of both groups possess as a common structural feature the 4-methoxyquinoline unit, in consequence of which they undergo a typical isomerization to iV-methyl-4-quinolones on vigorous treatment with methyl iodide. This reaction, which has been of considerable assistance in the elucidation of the structures of the alkaloids, also provides a chemical relationship with the alkaloid of Eehinopa species (Compositae), which was shown to be W-methyl-4-quinolone itself. The isomeric lV-methyl-2-quinolone occurs in Angostura bark. 

Alkaloid from bark of Angostura aupare, Roem. Sohnlt. Needles. M.p. 91-2°. Sd. EtOH, Et20. 

Houghton PJ, Woldemariam TZ, Watanabe Y, Yates W (1999) Activity Against Mycobacterium tuberculosis of Alkaloid Constituents of Angostura Bark, Galipea officinalis. Planta Med 65 250... 

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