Glycosmis mauritiana

Prenyl-quinolones and Related Tricyclic Alkaloids.—The l-methyI-3-prenyl-2-quinolone (6 R1 = H, R2 = OMe), already known as a synthetic compound, has been isolated from the roots of Glycosmis mauritiana it is converted into a mixture of the dihydropyrano-quinolones (8 R1 = H, R2 = OMe) and (9 R1 = H, R2 = OMe) by formic acid (Scheme 2).4 A new l-methyl-3-prenyl-2-quinolone, 7V-methylpreskimmianine (6 R1 = R2 = OMe), was obtained from the stem bark of Vepris louisii-, its structure was established by spectroscopy and by its preparation from preskimmianine (7) (Scheme 2).11 A second new alkaloid of Vepris louisii, named veprisine, was shown by spectroscopic studies and by its synthesis from A-methylpreskimmianine to be the pyrano-quinolone (10) (Scheme 2).11 Five furoquinoline alkaloids were found in the wood of Esenbeckia flava (see Table 1) and a non-crystalline bisprenyl compound (11) was also isolated from this source the new alkaloid, which was first obtained as a synthetic compound,17 is readily converted into the dihydropyrano-4-quinolone (9 R1 = R2 = H) (Scheme 2).1... 

In addition to quinoline alkaloids (see Table 1), Glycosmis mauritiana contains 5-hydroxy-2,3-dimethoxy-A7-methylacridone (arborinine) and a new prenyl-acridone (28).4 The structure of the latter alkaloid was indicated by spectroscopy, by the presence of a peri-hydroxyl group, and by heating it with formic acid to give the cyclization product (29), thus showing that the prenyl group was at C-2, i.e. adjacent to the hydroxyl group, rather than at C-4. An unexpected by-product of the reaction with formic acid was the acridone (22). 

From leaves of Glycosmis mauritiana (Rutaceae). Mp 83-84°. Originally reported as a cinnamic acid deriv. (rZ,2E)-form [152135-60-9]... 

Veprisine ni 7,8-diOMe, 1-Me Araliopsis tabouensis (A. soyauxii) [23], Glycosmis mauritiana [43], Oricia renieri [44], Stauranthus perforatus [35], Vepris louisii [44], V. stolzii [44]... 

OH, 10-Me Boenninghausenia albiflora [44], Boronia lanceolata [28], Glycosmis mauritiana [43], Ruta chalepensis [25], R. chalepensis var. latifolia [23], R. graveolens [42], Thamnosrtut rhodesica [38]... 

Intekhab J, Aslant M, Khalid H (2011) Phytochemical Study of Glycosmis Mauritiana. Am J Plant Sci 2 657-659... 

Rastogi K, Kapil RS, Popli SP 1980 New alkaloids from Glycosmis mauritiana. Phytochemistry 19 945-948... 

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