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A new benzylic diglycoside was isolated from the leaves of Milicia excelsa and identified as 3,4-dimethoxybenzyl ß-D-xylopyranosyl(1⃗2)-ß-D-glucopyranoside (1). It was oßtained together with four known secondary metaßolites including lupeol acetate (2), ursolic acid (3), triacontyl (E)- ferulate (4), and 2-(3,5-dihydroxyphenyl)ßenzofuran-5,6-diol (5). Their structures were determined ßased on their spectroscopic data and by comparison with those reported in the literature.

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A new flavonoid identified as 2-(2,4-dihydroxyphenyl)-5-hydroxy-8,8-dimethyl-4H,8H-pyrano[2,3-f]chromen-4-one (2'-hydroxyatalantoflavone) (1) was obtained from the roots of Milicia excelsa along with five known compounds including atalantoflavone (2), neocyclomorusin (3), 6-geranylnorartocarpetin (4), cudraxanthone I (5), and betulinic acid (6). The structures of the isolates were established on the basis of their spectral data and by comparison with those reported in the literature.

The chemical investigation of the total alkaloid extract (TAE) of the stem bark of Araliopsis soyauxii (Rutaceae) afforded an unreported indolopyridoquinazoline (compound 1) along with nine previously known alkaloids 2-10. In addition, six semi-synthetic derivatives 3a-c, 4b, 5a and 6a were prepared by allylation and acetonidation of soyauxinium nitrate (5), edulinine (3), ribalinine (4) and arborinine (6). The structures and spectroscopic data of five of them are reported herein for the first time. The suggested mechanism for the formation of the new N-allylindolopyridoquinazoline 5a is presented. The structures of natural and derived compounds were determined employing extensive NMR and MS techniques. The absolute configuration of stereogenic centers in compounds 2-4 were determined using NOESY technique and confirmed by the single-crystal X-ray diffraction (SC-XRD) technique. The use of SC-XRD further enabled us to carry out a structural revision of soyauxinium chloride recently isolated from the same plant to soyauxinium nitrate (5). The TAE, fractions, compounds 1-7 and 9, and semi-synthetic derivatives 3a-c, 4b, 5a and 6a were evaluated for their cytotoxic activity towards the cervix carcinoma cell line KB-3-1. No significant activity was recorded for most of the compounds except for 9, which showed moderate activity against the tested cancer cell lines.