Glycosmis citrifolia

Several hydroxylated and methoxylated acronycine analogues were isolated from Citrus depressa (Rutaceae), a Chinese drug Chen-pi used for treating heartache, abdominal pain, diarrhoea, tussis, vomiting, inappetence, and as an expectorant, and from Glycosmis citrifolia (Willd.) Lindl. (G. cochinchinensis Pierre), a wild shrub used in the treatment of scabies, boils and ulcers [289-291]. None of these compounds was reported to possess antineoplastic activity. 

Related to these structures is the natural "dimer" glycobismine A (54) first isolated from Glycosmis citrifolia by H. Furukawa et al., (Chem.pharm.Bull., 1984, 32, 1647). 

A fully dehydrogenated furoacridine (furacridone = furofoline-l) 345 was detected for the first time in Ruta graveolens by Reisch et al. (77P151) as a mixture with l-hydroxy-3-methoxy-10-methylacridin-9(10//)-one. Wu et al. [83JCS(P1)1681] were able to isolate furofoline-I 345 and furofoline II 346 from Glycosmis citrifolia (willd.) Lindl. 

The report of these semisynthetic derivatives preceded the report of the isolation of glycobismine A, the first naturally occurring bis-acridone alkaloid isolated from the bark and root bark of Glycosmis citrifolia collected in Taiwan [7]. Oligomers of noracronycine and related alkaloid derivatives, dimers and trimers, tetramers, and pentamers were also reported [8], and these oligomers and the chemical reactions concerning acronycine and related compounds were reviewed [9,10]. 

Alkaloid from leaves of Glycosmis citrifolia (Rutaceae). Needles. Mp 174-175°. 

Glycosolone 1-Me, 3-CH2CH = CMe2,4-OMe, 8-OH Glycosmis citrifolia [34], G. pentaphylla [44]... 

Evomeliaefolin 3-CH(OH)CH2COMe, 4,7,8-triOMe Glycosmis citrifolia [30], Tetradium glabrifolium (= Euodia meliaefolia) [30]... 

Glycocitrine-II 1,3-diOH, 4-CH2CH = CMe2, 10-Me Glycosmis citrifolia [16]... 

Glycocitrine-I 1,5-diOH, 3-OMe, 4-CH2CH = CMez Citrus grandis [22], C. hybrid Yalaha XC. paradisi x C. tangerina) [30], C. maxima [40], C. paradisi [32], Glycosmis citrifolia [16], Severinia huxifolia [34]... 

Glycocitrine-VI 1-OH, 3- = 0,4-diCH2CH = CMez, 10-Me, 4,5-dihydro Glycosmis citrifolia [34]... 

Des-A-methyl- Noracronycine I 1-OH, 10-H Glycosmis citrifolia [18], G. trichanthera (G. calcicold) [33], Murraya paniculata [44]... 

Des-A-methyl- Acronycine I 1-OMe, 10-H Acrortychia baueri [18], Glycosmis citrifolia [18], G. mauritiana [24], G. pentalhylla [42], Medicosma subsessilis [3S], Murraya paniculata [44], Sacomelicope dogniensis [22], S. follicidaris [38], S. megistophylla [34]... 

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