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The spectral, especially fluorescence properties, of seven selected quaternary benzo[ c]phenantridine alkaloids ( sanguinarine, chelerythrine, chelirubine, sanguirubine, chelilutine, sanguilutine, and macarpine) were studied in presence and in absence of double-stranded DNA. This study has proved dramatic differences in fluorescence emission of all studied alkaloids in presence of calf thymus DNA in comparison to fluorescence of free alkaloids. The most remarkable are changes in emission spectra of macarpine, chelirubine, and sanguirubine. Association constants (log K) for interaction of all studied alkaloids with CT DNA were calculated. [ABSTRACT FROM AUTHOR]

Abstract: The content of the seven quaternary benzo[c]phenanthridine alkaloids (QBA) sanguinarine (SA), chelerythrine (CHE), chelirubine (CHR), chelilutine (CHL), sanguilutine (SL), sanguirubine (SR) and macarpine (MA) was determined in the underground part of six plant species of the family Papaveraceae (Sanguinaria canadensis L., Dicranostigma lactucoides HOOK.f.et THOMS, Chelidonium majus L., Macleaya cordata (Willd.), Macleaya microcarpa (Maxim) and Stylophorum lasiocarpum (Oliv.)). HPLC method with reversed phase column Synergi™ Max-RP C-12 Phenomenex was used, mobile phase consisted of heptanesulfonic acid (0.01mol/l) with triethanolamine (0.1mol/l) in redistilled water, pH 2.5, acetonitrile gradient 25–60% during 25min. Detection was performed at 280nm. The highest content of SA and CHE was found in the roots of D. lactucoides (1.99%, resp. 3.43% of the dried roots). In rhizomes of S. canadensis was their content more then two times lower. [Copyright &y& Elsevier]

Quaternary benzo(c)phenanthridine alkaloids are a relatively small group of isoquinoline alkaloids with attractive biological activities. They are produced by a number of plant species of the Papaveraceae, Fumariaceae, and Rutaceae families. Differential cytotoxicity of minor, naturally occurring derivatives sanguirubine, chelirubine, and macarpine and better known benzophenanthridines sanguinarine and chelerythrine in cancer and normal cells was assessed in vitro by MTT assay using a panel consisting of either transformed cell lines (HeLa; A431; HL60) or primary fibroblasts of human origin. IC50 values were determined 72 h after addition of the alkaloids. A wide range (0.01-1.44 µg/mL) of IC50 was observed, and the highest toxicity was determined for macarpine. Human promyelocytic leukemia line HL60 has been documented to be the most sensitive to alkaloid treatment followed by human skin fibroblasts, while human cervix adenocarcinoma HeLa cells and epidermal carcinoma cells A431 appeared more resistant. The most sensitive cell line HL60 was selected for demonstrating the ability of the alkaloids to induce apoptosis by analyzing morphologic changes upon DAPI staining, ultrastructural changes, and annexin V versus propidium iodide staining assay. Apoptosis was induced by sanguirubine, chelirubine, chelerythrine, and macarpine at a concentration of 1 µg/mL. The results show that the alkaloids tested have a strong antiproliferative effect in vitro due predominately to apoptosis. [ABSTRACT FROM AUTHOR]

Abstract: Extracts from Himalayan herb Dicranostigma lactucoides containing alkaloid chelirubine have been used for centuries in Chinese herbal medicine. We have found a new utilization for the alkaloid: it can be used as a DNA fluorescent probe showing blue (free form) and red (intercalated to DNA) luminescence emission after irradiation by near-UV light. Besides quantification of DNA (LOD=6ngml−1) it can also be used as a supravital cell probe because chelirubine molecules can effectively enter into the living cell through the cell membrane. [Copyright &y& Elsevier]