4-quinolone alkaloids

Hamasaki N, Ishii E, Tominaga K, Tezuka Y, Nagaoka T, Kadota S, Kuroki T, Yano 1. (2000) Highly selective antibacterial activity of novel alkyl quinolone alkaloids from a Chinese herbal medicine, Gosyuyu (Wu-Chu-Yu), against Helicobacter pylori in vitro. Microbiol Immunol 44 9-15. 

Oliva A, Meepagala KM, Wedge DE, Hale AL, Harries D, Aliotta G, Duke SO, Natural fungicides from Ruta graveolens L. leaves, including a new quinolone alkaloid, y Food Chem 51 890—896, 2003. 

H. S. and Kim, Y. K. 2002. Quinolone alkaloids, diacylglycerol acyltransferase inhibitors from the fruits of Evodia rutaecarpa. Planta Medica, 68 1131-1133. 

Evodia rutaecarpa (Juss.) Berth Wu Zhu Yu (Evodia) (fruit) Alkyl methyl quinolone alkaloids, evodiamine, limonin, evocarpine, rutaecarpine, N-methyl anthranilic acid, evodol, hydroxyevodiamine, N-methylanthranflamide, N,N-dimethyl-5 -methoxytryptamine, dehydroevodiamine.32,33,237 Antiemetic, analgesic, lower blood pressure, antibacterial. 

Abe I, Abe T, Wanibuchi K, Noguchi H (2006) Enzymatic formation of quinolone alkaloids by a plant type III polyketide synthase. Org Lett 8 6063-6065... 

Oliva, A., Meepagala, K. M. Wedge, D. E. Hale, A. L., Harries, D., Aliotta, G, Duke, S.O. Natural Fungicides from Ruta graveolens L. leaves, including anew quinolone alkaloid. J Agric Food Chem 2003 51 890-896... 

Providing rapid multiresidue analytical profiling is a first step toward effective quality control of herbal preparations. For example, Luo et al. [5] developed a method for the simultaneous analysis of protoberberine alkaloids, indolequinoline alkaloids, and quinolone alkaloids (Figure 13.1) extracted from the traditional Chinese medicinal... 

B indolequinoline alkaloids, and C quinolone alkaloids where R is one of various long-chain alkanes, alkenes, and dienes. 

In earlier reports, evidence for the structure of ptelefoline (authors code number Pt/13) (7) and related iV-methyl-2-quinolone alkaloids from Ptelea trifoliata had been presented.13 A somewhat confusing situation has arisen as a result of ascribing the same name to another alkaloid isolated from the same species which, however, possesses the structure (4) and code number Pt/22.9 The structure (4) of Pt/22 was established by spectral means importantly, the mass spectrum of (4) showed a base peak at M - 15 which was attributed to the benzopyrylium ion (8). It is to be hoped that either Pt/13 or Pt/22 will be re-named in the near future. 

A known quinolone alkaloid, integriquinolone (5), has been reported from Limonia acidissima (L.) Swingle (syn Feronia limonia Feronia elephan-... 

L. leaves, including a new quinolone alkaloid. Journal of Agricultural and Food Chemistry, 51, 890—896. 

Flindersine and a new quinolone alkaloid, 3-dimethylallyl-4-dimethyl-allyloxy-2-quinolone, C19H23O2N (mp 114°-115°) were isolated. Mass and NMR spectroscopy indicated structure LXVIIa for this base. Minor chemical reactions served to confirm this structure, particularly catalytic hydrogenation, which induced rapid hydrogenolysis of the ether linkage 102). 

Data for 2-alkyl- and 2-aryl-4-quinolone alkaloids are given in Table VIII (3, 69, 134, 208-217). 

New quinolone alkaloids and alkaloids of established constitution obtained from new sources are listed in Table 1/ ... 

QURESHI, A.A., HUANBIAO, M., PACKER, L., PETERSON, D. Isolation and identification of novel tocotrienols from rice bran with hypocholesteremic, antioxidant and antitumor properties, J. Agric. Food Chem., 2000, 48, 3130-3140. CHUNG, H.S., WOO, W.S., A quinolone alkaloid with antioxidant activity from the aleurone layer of anthocyanin-pigmented rice, J. Nat. Prod., 2001, 64, 1579-1580. 

Evidence from a number of incorporation studies indicates that quinolone alkaloids are derived from anthranilic acid and acetate or malonate. The structure of casimiroine (13) requires only the usual processes of hydroxylation, methylation, and closure of the methylenedioxy ring at appropriate stages of the pathway. 

Quinolone alkaloids are found most commonly in the Rutaceae, but occasionally are encountered in other families. Alkaloids with a quinoline ring structure occur in four of the seven subfamilies of the Rutaceae (Aurantioideae, Flin-dersioideae, Rutoideae, and Toddalioideae) (in addition, a pyranoquinolone, A -methylflindersine, occurs in the Spathelioideae). Quinolone alkaloids are found in the subfamilies Rutoideae, Toddalioideae, and Aurantioideae, but also have been reported from Xylocarpus (Meliaceae). 

Many quinolone alkaloids are subject to prenylation and give rise to the furoquinoline or pyranoquinoline alkaloids. The furan rings of furoquinoline alkaloids arise by a similar process to thos of furanocoumarins that have been previously discussed (Fig. 31.8). see also Chapter 9) (Geissman and Crout, 1969 Grundon, 1979, 1983). 

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