Twenty‐eight compounds including seven alkaloids, (+)‐3‐chloro‐N‐formylnornantenine (1), (+)‐N‐formylnornantenine (2), (+)‐boldine (3), (+)‐norboldine (4), (‐)‐norboldine (5), lycicamine (6), and tetrahydroberberine (7); four flavonoids, kaempferol (8), kaempferol‐3‐O‐arabinoside (9), quercetin (10), and quercetin‐3‐O‐rhamnoside (11); one butanolide, akolactone A (12); one p‐quinone, 2,6‐dimethoxy‐p‐quinone (13); one cyclohex‐2‐en‐1‐one, blumenol A (14); six benzenoids, methylparaben (15), p‐hydroxybenzoic acid (16), vanillic acid (17), syringic acid (18), 3,4,5‐trimethoxybenzoic acid (19), and 3‐(3,4‐dihydroxyphenyl) propionic acid (20); one diterpene, phytol (21); one triterpene, squalene (22); six steroids, (3‐sitosterol (23), β‐sitostenone (24), stigmasta‐4,22‐dien‐3‐one (25), 6β‐hydroxy‐β‐sitostenone (26), 6β‐hydroxystigmasterone (27), and β‐sitosteryl‐D‐glucoside (28) were isolated from the aerial part of Lindera glauca. These compounds were characterized and identified by physical and spectral method. All compounds were isolated for the first time from this plant. Among them, (+)‐3‐chloro‐N‐formylnornantenine (1) is a new one.
Two new protopine-type alkaloids, argemexicaine A (1) and argemexicaine B (2), along with thirteen known alkaloids, were isolated from MeOH extracts of Formosan Argemone mexicana L. (Papaveraceae). Physical and spectral analyses, particularly IR and thermo-modulated 1D and 2D NMR, were used to determine the transannular conformations of the isolated protopine-type alkaloids. The known benzo[ c]phenanthridine (+/-)-6-acetonyldihydrochelerythrine (5) exhibited significant anti-HIV activity in H9 lymphocytes with EC50 and TI (Therapeutic Index) values of 1.77 microg/mL and 14.6, respectively.
Fractionation of the chloroform extract from the aerial part of Argemone mexicana led to the isolation of two benzophenanthridine-type alkaloids, N-demethyloxysanguinarine and pancorine; three benzylisoquinoline-type alkaloids, (+)-1,2,3,4-tetrahydro-1-(2-hydroxymethyl- 3,4-dimethoxyphenylmethyl)-6,7-methylenedioxyisoquinoline, (+)-higenamine and (+)-reticuline. Among them, N-demethyloxysanguinarine is a new compound, and (+)-1,2,3,4- tetrahydro-1-(2-hydroxymethyl-3,4-dimethoxyphenylmethyl)-6,7-methylenedioxy-isoquinoline was isolated form a natural source for the first time, to which was assigned a trivial name, (+)-argenaxine. In addition, six known non-alkaloidal compounds were also isolated and identified. All compounds were characterized on the basis of their spectral data and chemical evidences. Some isolated alkaloids from this species were evaluated for their cytotoxicity to human nasopharyngeal carcinoma (HONE-1) and human gastric cancer (NUGC) cell lines. Chelerythrine was found to exhibit significant activity against NUGC cell line, while angoline inhibited both types. (+)-Argenaxine showed moderate activity against the NUGC cell line.
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