New alkaloids from Glycosmis mauritiana

Chemical investigation of the roots of G. mauritiana resulted in the isolation of two new alkaloids; 1-hydroxy-3-methoxy-2-(3-methylbut-2-enyl)-N-methylacridan-9-one (1) and 4,8-dimethoxy-3-(3-methylbut-2-enyl)-N-methyl-2-quinolone (6). The structures of these new bases have been established by chemical and spectroscopic methods and confirmed in the case of 6 by its synthesis. Interestingly, the formic acid-catalysed cyclisation of 1 gave the dealkylated product 3 along with the pyrano-[2, 3-a]-acridine (4).     

Alkaloids from Haplophyllum buxbaumii

In addition to the known alkaloids kokusaginine, skimmianine, γ-fagarine and a lignan, justicin B, the aerial parts of Haplophyllum buxbaumii afforded three new alkaloids: 4,5,6-trimethoxyfuroquinoline, 4,5,7-trimethoxyfuroquinoline and N-hydroxymethylflindersine. The structures of the known and the new compounds were assigned by spectral methods.     

Alkaloids of the leaves of Glycosmis bilocularis

Six alkaloids have been isolated from the leaves of Glycosmis bilocularis, 5 of which are known compounds viz. arborine, arborinine, glycorine, kokusaginine and skimmianine, all previously isolated from other species of Glycosmis. The sixth alkaloid was identified as 1,5-dihydroxy-2,3-dimethoxy-10-methyl-9-acridone (5-hydroxy-arborinine).     

Alkaloids of some Mexican Zanthoxylum species

Two new 4-quinazolone alkaloids have been isolated from seed husks of Zanthoxylum arborescens. Based on their spectroscopic properties they have been assigned structures, 1-methyl-3-(2′-phenylethyl)-1H,3H-quinazoline-2,4-dione and 1-methyl-3-[2′-(4″-methoxyphenyl)ethyl]-1H,3H-quinazoline-2,4-dione. These structural assignments have been confirmed by synthesis. Skimmianine has been obtained from leaf extracts of Z. dimoncillo and Z. caribaeum while skimmianine and scopeletin have been isolated from leaf extracts of Z. fagara.