Simple quinolines and 4-quinolinones

Simple quinolines and quinolin-4-ones often occur outside of the Rutacae plant family, thus the brominated quinoline (1) is metabolised by the marine bryozoan Flustra foliacea (P. Wulff, J.S. Carle and C. Christophersen, Comp.Biochem.Physiol.B, 1982, 71, 525) and an unusual 

Ephedralone (3) is claimed as an alkaloid from the Egyptian plant Ephedra alata (M.A.M. Nawar et al., Phytochera., 1985, 24, 878).  

4-Quinolones ( 1) with long alkyl chains attached to position 2 are metabolised by bacteria and have been given the name pseudanes to denote their Initial discovery in the 

Malatyamlne (5), in the form of its ethyl ester, has been obtained from Haplophyllum oappadocioum indigenous to Turkey (G. Arar et al., J.nat.Prod., 1985, 48, 642). Since ethyl 

Another new quinolinone norgraveoline (9,R = H), is accompanied by graveoline (9, R = Me) in Haplophyllum dubiwn (Razakova, Bessonova and S.Yu.Yunusov, ibid., 1979, 8l0 C.A., 1980, 9Z, 22586). The latter alkaloid is a common constituent of Rutaceous plants. Unusual structures are provided by melochinone (10) (G.J. Kapadia et al., 

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