Acronychia baueri

In regard to the antineoplastic properties of Rutaceae, this family has attracted a great deal of interest for its ability to elaborate series of cytotoxic benzo[c]phenanthri-dine and acridin alkaloids. Examples of acridin alkaloid are pyrano-acridone and acronycine characterized from Acronychia baueri Scott. 

SE-54) for the separation of nine alkaloids Of Acronychia baueri Bauerella australiana). ... 

When [4- H]anthranilic acid was administered to Acronychia baueri, skimmianine (38) and acronidine (40) showed approximately 10% and 20% tritium retention respectively when compared to the radioactivity incorporated into the acridone alkaloids of this plant.These results were taken to indicate a partial NIH shift on hydroxylation, in which one of the ortho positions was favoured over the other. However, the results for acronycidine (41) do not satisfactorily support this view the incorporations as well as the retention of tritium in skimmianine and acronidine are low and the sites of tritium labelling were not... 

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. 

Acronycine (57), isolated in the Lilly laboratories from different Acronychia spp. (Rutaceae), has shown the broadest experimental tumour activity of any alkaloid studied. It was first isolated from Acronychia baueri Its activity against C-I498 myelogenous leukaemia, X-5563 plasma cell myeloma, and adenocarcinoma 755 was found by the Lilly group.Acronycine has been obtained by different syntheses however, no evidence for clinical trials with acronycine has yet been found in the literature. 

Details of the previously outlined32 synthesis of acronycine (58), an alkaloid isolated from Acronychia baueri which showed anti-tumour activity, have now appeared.33 In this paper, it is shown that unequivocal confirmation of structure (58) for acronycine may also be obtained from n.m.r. and nuclear Overhauser effect studies. 

Acronycine (1.) is a natural alkaloid which was first isolated in 1948 from the bark of a small Australian Rutaceous tree, Acronychia baueri Schott (1). Since that time, the status of this plant within the Rutaceae family has been revised several times, in the course of successive taxonomic studies (2-5). It is now widely accepted that the plant belongs to the genus Sarcomelicope and should be named Sarcomelicope simplicifolia (Endl.) Hartley ssp. simplicifolia (4). 

Several groups have studied the hydroxylation of furoquinoline alkaloids. Anthranilic acid is a specific precursor of acronidine (195, Section IV,A,7) in Acronychia baueri (187). Hall and Prager (232) fed [4-3H]anthranilic acid to the plant and estimated that, during hydroxylation to acronidine and skimmianine, migration of tritium occurred to the extent of... 

Acronycine was isolated from the bark of the Australian scrub ash, Baurella simplicifolia =Acronychia baueri) (Rutaceae), together with related alkaloids [1]. Acronycine is classified as an acridone alkaloid, and acridone is an oxidized derivative of acridine. Acridine itself was isolated from coal tar in the nineteenth century, but the isolation of acronycine and related alkaloids was the first occasion that the acridine (acridone) unit was isolated from a higher plant. 

Acronycidine I 4,5,7,8-tetraOMe Acronychia baueri [42, 44], Bauerella simplicifolia ssp. neo-scotica [44], Medicosma subsessilis [38], Melicope foreana [42], Sarcomelicope leiocarpa [19], S. megistophylla [29]... 

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