Haplophyllum dubium

Non-hemiterpenoid Quinolines.—A re-examination of the alkaloids of Haplophyllum dubium resulted in the isolation of two members of the 2-aryl-4-quinolone group, i.e. graveoline (2 R = Me) and the new alkaloid norgraveoline (2 R = H).5 A new bacterial pseudan (3) has been obtained from Pseudomonas aeruginosa.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). 

Acridone Alkaloids.—No general review on this group has appeared for at least five years, but discoveries of individual alkaloids have been recorded" and a discussion of antitumour properties of certain bases has been published." Alkaloids have been isolated from Acronychia baueri Bauerella australiana), A. haplophylla, " Haplophyllum dubium, and Teclea natalensis With the exception of T. natalensis, which has yielded the first known acridone type with oxygenation in ring a (24), all other plant species have been shown to contain known alkaloids. 

Dubamine 3 -0CH20-4 Haplophyllum dubium [3, 41], H. latifolium [59], Dictamnus alhus [42]... 

Lunasia amara Blanco (leaves) (2,129) Galipea longiflora K. Krause (stem bark) (45,128) Haplophyllum dubium Korovin (leaves) (3, 130-132) Haplophyllum latifolium Kar. Kir. (leaves, roots, and seeds) (133) Dictamnus albus L. (39)... 

R. graveolens, Lunasia amara, Haplophyllum dubium, H. latifolium, and the microbial species P. aeruginosa, P. cepacia, P. fluorescens, Pseudonocardia sp., Arthrobacter sp.,... 

Methoxy-l-methyl-2-quinolone (1) was isolated from Hesperethusa crenulata M. Roem. (12) and from the wood of Fagara boninensis (13). The alkaloid folimine from Haplophyllum foliosum Vved. (14) was identified as 4,8-dimethoxy-l-methyl-2-quinolone (2), which had been obtained earlier during the degradation of foliosine (Volume IX, p. 225). Folifidine from H. dubium Eug. Kor (15) and from H. foliosum (16) is the 8-hydroxy-2-quinolone 3. 

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