Cytotoxic Benzophenanthridine and Benzylisoquinoline Alkaloids from Argemone mexicana

Abstract

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.

DNA Topoisomerase I Inhibitory Alkaloids from Corydalis saxicola

“…Pale yellow amorphous powder. 1 (11)). 13 C-NMR ((D 6 )DMSO): 39.4 (MeN); 56.6 (MeOÀC(8)); 61.6 (MeOÀC(7)); 84.6 (C(6)); 100.5 (C(4)); 101.9 (OCH 2 O); 105.1 (C(1)); 113.9 (C(9)); 119.4 (C(10)); 120.4 (C(11)); 122.8 (C(10b)); 123.9 (C(12)); 124.8 (C(10a)); 126.0 (C(4a)); 126.7 (C(6a)); 131.2 (C(12a)); 138.8 (C(4b)); 146.6 (C(7)); 147.8 (C(2)); 148.4 (C(3)); 152.…”

“…So far, seven quaternary alkaloids (i.e., dehydrocavidine (1), chelerythrine (10), berberine (2), palmatine (3), coptisine, dehydroapocavidine, and tetradehydroscoulerine) [1] [3] and ten tertiary alkaloids (i.e., cavidine (12), thalictrifoline, 13b-hydroxystilopine, scoulerine (11), tetrahydropalmatine (13), tetrahydrocolumbamine, protopine, oxyacanthine, allocryptopine, and 1-nitroapocavidine) were isolated from C. saxicola [1] [3] [4]. Furthermore, seven non-alkaloid compounds (i.e., oleanolic acid, daucosterol, b-sitosterol, betulin, cycloeucalenol, betulinic acid, and bamyrin acetate) were also isolated from this plant [3].…”

“…Tetrahydropalmatine (13) and cheilanthifoline (14) displayed inhibitory effects on EBV-EA (Epstein-Barr virus early antigen) activation induced by 12-O-tetradecanoylphorbol-13-acetate in Raji cells [9]. Chelerythrine (10) was shown to be inhibitory against SQ-20B [10], NUGC [11], HepG2 [12], KB [13], LNCaP, and DU-145 [14] cell lines. Berberine (2) is cytotoxic to many tumor cell lines including hepatoma cells, leukemia cells [15] [16], and HT-29, Hep-2 (larynx tumor), MCF-2 (breast cancer), MKN (gastric cancer) [17], SNU-5 (gastric cancer) [18], B16 (murine melanoma) [19], and EAC [20] cell lines.…”

Fusarium oxysporum homogenates and jasmonate induce limited sanguinarine accumulation in Argemone mexicana cell cultures

“…A. mexicana has been used for a long time in Mexican traditional medicine. The presence of benzylisoquinoline alkaloids (BIA), such as alocriptopine, berberine, coptisine, chelerythrine, dihydrochelerythrine, protopine, and sanguinarine, may explain some of the Argemone alleged medical properties (Chang et al 2003). We are interested in developing biotechnological tools for the study of this remarkable plant.…”

Bark Constituents from Mushroom-detoxifiedRhus vernicifluaSuppress Kainic Acid-induced Neuronal Cell Death in Mouse Hippocampus

“…Stigmasterol also has been reported to exhibit anti-osteoarthritic [4] and cytotoxic activities [5]. Although RVH-1 has been isolated from various natural plants such as Lawsonia inermis [6] and Typha latifolia [7] and RVH-2 from Argemone mexicana [8] and Stephania cepharantha [9], their biological activities have not been clearly elucidated.…”