From the embryos of the seeds of Nelumbo nucifera, three bisbenzylisoquinoline alkaloids, nelumboferine and nelumborines A and B, were isolated along with four known compounds, neferine, liensinine, isoliensinine and anisic acid. The structures of the new alkaloids were determined mainly by spectroscopic methods.

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From the dried roots of Rauwolfia serpentina were isolated five new indole alkaloids, N(b)-methylajmaline (1), N(b)-methylisoajmaline (2), 3-hydroxysarpagine (3), yohimbinic acid (4), isorauhimbinic acid (5), a new iridoid glucoside, 7-epiloganin (6), and a new sucrose derivative, 6'-O-(3,4,5-trimethoxybenzoyl)glomeratose A (7), together with 20 known compounds. The structures of the new compounds were determined by spectroscopic and chemical means. The inhibitory activities of the selected alkaloids on topoisomerase I and II and their cytotoxicity against the human promyelocytic leukemia (HL-60) cell lines were assessed.

Reinvestigation of the fruits ofdiangium iamarckii has led to the isolation and structural determination of five new tetrahydroisoquinoline-monoterpene glucosides, methylisoalangiside 151, isoalangiside 161, 3-0-demethyl-2-0-methylisoalangiside 1 7 , demethylneoalangiside 181, and neoalangiside 191, as well as a novel tetrahydro-P-carbolinemonoterpene glucoside, 1 0-hydroxyvincoside lactam 1101. Demethylalangiside, sweroside, and phenethyl alcohol xylopyranosyl(l-16) glucopyranoside were also isolated for the first time from this plant. The structures of the new compounds were elucidated by spectroscopic and chemical methods. The biogenesis of these glucosides is also discussed.Alangium lamarckii Thwaites (Alangiaceae) is a deciduous shrub that is widely distributed throughout India and southeast Asia. The root bark of this plant finds extensive usage in folk medicine as an anthelmintic, purgative, emetic, and febrifuge, as well as in the treatment of leprosy and other skin diseases. Previous phytochemical studies on this plant focused mainly on its alkaloidal constituents, which include ipecac alkaloids, represented by emetine 111 and cephaeline E27 (2). The glucosidal constituents, by contrast, remained to be examined except for alangiside 137 and loganic acid (3), although the alkaloids were shown to be biosynthesized via a glucosidal intermediate. In the course of our phytochemical studies on nitrogenous glycosides (4), we have recently investigated the constituents of the fruits of A. lamarckii and isolated 3-0demethyl-2-0-methylalangiside 141 (5). Re-examination of the plant material was undertaken, since a preliminary study showed the presence of various nitrogenous glycosides. In this paper we describe the isolation and characterization of five new unusual tetrahydroisoquinoline-monoterpene glucosides and a tetrahydro-p-carbolinemonoterpene glucoside, and discuss the biogenesis of these compounds. RESULTS AND DISCUSSIONDried and crushed fruits ofA. lamarckii were extracted with hot MeOH. The MeOH extract was successively partitioned between H 2 0 and CHC1, and between H20 and n-BuOH. The n-BuOH-soluble fraction was fractionated by open-column chromatography on Si gel and reversed-phase mplc and then purified by reversed-phase hplc and prep. tlc, affording five novel tetrahydroisoquinoline-monoterpene glucosides 15-91 and a tetrahydro-p-carboline monoterpene glucoside 1101, along with the known glycosides alangiside 131, 3-0-demethyl-2-0-methylalangiside 141, demethylalangiside 1117 (4), sweroside (6), and phenethyl alcohol xylopyranosyl (1 +6) glucopyranoside (7). The latter three glycosides were isolated for the first time from this plant species.Compound 5 was isolated as an amorphous powder, analyzed for C,,H,,NO,, from its hrsims. It showed uv maxima at 235,282, and 292 (sh) nm, and ir bands at 3406