Abstract
Chromatographic separation of the MeOH extract from the stems and rhizomes ofSinomemium acutum led to the isolation of nine alkaloids and a lignan. Their structures were determined to be dauriporphine (1), bianfugecine (2), dauriporphinoline (3), menisporphine (4), (−)-syringaresinol (5), N-feruloyltyramine (6), acutumine (7), dauricumine (8), sinomenine (9), and magnoflorine (10) by spectroscopic means. These compounds were examined for their P-gp mediated MDR reversal activity in human cancer cells. Compound1 showed the most potent P-gp MDR inhibition activity with an ED50 value 0.03 μg/mL and 0.00010 μg/mL in the MES-SA/DX5 and HCT15 cells, respectively.
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Al-Howiriny, T. A., Zemaitis, M. A., Gao, C., Hadden, C. E., and Martin, G. E., Thalibealine, a novel tetrahydroprotoberberine-aporphine dimeric alkaloid fromThalictrum wangii.J. Nat. Prod., 64, 819–822 (2001).
Choi, S. U., Kim, N. Y., Choi, E. J., Kim, K. H., and Lee, J. O., Establishment of doxorubicin-resistant subline derived from HCT15 human colorectal cancer cells.Arch. Pharm. Res., 19, 342–347 (1996).
Fukuda, N., Yonemitsu, M., and Kimura, T., Studies on the constituents of the stems ofTinospora tuberculata BEUMEE I.N-trans- andN-cis-feruloyl tyramine, and a new phenolic glucoside, tinotuberide.Chem. Pharm. Bull., 31, 156–161 (1983).
Hou, C.-Y. and Xue, H., Studies on the chemical constituents ofMenispermum dauricum DC.,Acta. Pharm. Sinica., 20, 112–117 (1985).
Kunitomo, J. and Satoh, M., Structure of menisporphine: a new type of isoquinoline alkaloid.Chem. Pharm. Bull., 30, 2659–2660 (1982).
Kunitomo, J. and Satoh, M., Structure and synthesis of menisporphine, a new type of isoquinoline alkaloid: alkaloids ofMenispermum dauricum DC (9).Tetrahedron, 39, 3261–3265 (1983).
Kunitomo, J., Kaede, S., and Satoh, M., The structure of 2,3-dihydro menisporphine and the synthesis of dauriporphine, oxoisoaporphine alkaloids fromMenispermum Dauricum DC.,Chem. Pharm. Bull., 33, 2778–2782 (1985).
Marsaioli, A. J., Reis, F. de A. M., Magalhaes, A. F., and Ruveda, E. A., 13C-NMR analysis of aporphine alkaloids.Phytochemistry, 18, 165–169 (1979).
Otsuka, H., Ito, A., Fujioka, N., Kawamata, I., Kasai, R., Yamasaki, K., and Satoh, T., Butenolides fromSinomenium acutum.Phytochemistry, 33, 389–392 (1993).
Saxena, N. K. and Bhakuni, D. S., The quaternary alkaloids ofCocculus laurifolius DC.J. of Indian Chem. Soc., LVI, 1020–1023 (1979).
Shouxun, Z., Wencai, Y., Ninghua, T., Haoru, Z., and Zuncheng, X., Anovel oxoisoaporphine alkaloid from the rhizome ofMenispermum dauricum.J. China Pharmaceutical University, 20, 312 (1989).
Skehan, P., Storeng, R., Scudiero, D., Monks, A., McMahon, J., Vistica, D., Warren, J. T., Bokesch, H., Kenney, S., and Boyd, M. R., New colorimetric cytotoxicity assat for anticancer-drug screening.J. Natl. Cancer Inst., 82, 1107–1112 (1990).
Sugimoto, Y., Babiker, H. A. A., Inanaga, S., Kato, M., and Isogai, A., Oxoisoaporphines fromMenispermum dauricum.Phytochemistry, 52, 1431–1435 (1999).
Sugimoto, Y., Babiker, H. A. A., Saisho, T., Furumoto, T., Inanaga, S., and Kato, M., Chloriated alkaloids inMenispermum dauricum DC. root culture.J. Org. Chem., 66, 3299–3302 (2001).
Vermes, B., Seligmann, O., and Wagner, H., Synthesis of biologically actibe tetrahydrofurofuranlignan-(syringin, pinoresinol)-mono-and bis-glucosides.Phytochemistry, 30, 3098–3089 (1991).
Wang, Y., Zhou, L., and Li, R., Study progress inSinomenium acutum (Thunb.) Rehd. et Wils.,Zhong Yao Cai, 25, 209–211 (2002).
Yan X., Zhou, J., and Xie, G., Traditional chinese medicines: molecular structures, natural sources and applications. Ashgate, pp. 738 (1999).
Yoshihiro, T., Kazuo, T., Shin, M., and Yoshiro, K., C-13 NMR spectra of morphine alkaloids, codeine thebaine, and sinomenine, and reated compounds.Tetrahedron Lett., 33, 2853–2856 (1975).
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Min, Y.D., Choi, S.U. & Lee, K.R. Aporphine alkaloids and their reversal activity of multidrug resistance (MDR) from the stems and rhizomes ofSinomenium acutum . Arch Pharm Res 29, 627–632 (2006). https://doi.org/10.1007/BF02968246
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DOI: https://doi.org/10.1007/BF02968246