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Inhibition of DNA topoisomerases I and II and cytotoxicity by lignans from Saururus chinensis

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Abstract

Thirteen lignans, erythro-austrobailignan-6 (1), meso-dihydroguaiaretic acid (2), sauchinone (3), 1′-epi-sauchinone (4), saucerneol D (5), manassantin B (6), manassantin A (7), nectandrin B (8), machilin D (9), saucerneol F (10), saucerneol G (11), saucerneol H (12) and saucerneol I (13), were isolated from the ethyl acetate extract of the roots of Saururus chinensis. Among these compounds, 5 showed potent inhibitory activities against DNA topoisomerase I and II, and 5, 6, 7 and 10 showed mild cytotoxicities against HT-29 (IC50 values; 13, 12, 11, and 10 µM, respectively) and HepG2 cell lines (IC50 values; 16, 11, 12, and 11 µM, respectively).

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References

  • Chattopadhyay, S. K. and Rao, K. V., Chemistry of Saururus cernuus, IV: Cyclooctadiene systems derived from austrobailignan-5. Tetrahedron, 43, 669–678 (1987).

    Article  CAS  Google Scholar 

  • Chen, A. Y. and Liu, L. F., DNA topoisomerase: essential enzymes and lethal targets. Annu. Rev. Pharmacol. Toxicol., 34, 191–218 (1994).

    Article  CAS  PubMed  Google Scholar 

  • Chung B. S. and Shin M. G., Dictionary of Korean Folk Medicine, Young Lim Sa, Seoul, p. 813 (1990).

    Google Scholar 

  • D’Arpa, P. and Liu, L. F., Topoisomerase-targeting antitumor drugs. Biochim. Biophys. Acta., 989, 163–177 (1989).

    PubMed  Google Scholar 

  • Filleur, F., Le Bail, J. C., Durous, J. L., Simon, A., and Chulia, A. J., Antiproliferative, anti-aromatase, anti-17β-HSD and antioxidant activies of lignans isolated from Myristica argentea. Planta Med., 67, 700–704 (2001).

    Article  CAS  PubMed  Google Scholar 

  • Fukuda, M., Nishio, K., Kanzawa, F., Ogasawara, H., Ishida, T., Arioka, H., Bojamowski, K., Oka, M., and Saijo, N., Synergism between cisplatin and topoisomerase I inhibitors, NB-506 and SN-38, in human small cell lung cancer cells. Cancer Res., 56, 789–793 (1996).

    CAS  PubMed  Google Scholar 

  • Hwang, B. Y., Lee, J. H., Nam, J. B., Hong, Y. S., and Lee, J. J., Lignans from Saururus chinensis inhibiting the transcription factor NF-êB. Phytochemistry, 64, 765–771 (2003).

    Article  CAS  PubMed  Google Scholar 

  • Hwang, B. Y., Lee, J. H., Nam, J. B., Kim, H. S., Hong, Y. S., and Lee, J. J., Two new furanoditerpenes from Saururus chinenesis and their effects on the activation of peroxisome proliferator-activated receptor γ. J. Nat. Prod., 65, 616–617 (2002).

    Article  CAS  PubMed  Google Scholar 

  • Ikeya, Y., Taguchi, I., and Yoshida, I., The constituents of Schizandra chinensis Baill. IV. The structures of two new lignans, pre-gomisin and gomisin J. Chem. Pharm. Bull., 27, 1583–1588 (1979).

    CAS  Google Scholar 

  • Kubanek, J., Fenical, W., Hay, M. E., Brown, P. J., and Lindquist, N., Two antifeedant lignans from the freshwater macrophyte Saururus cernuus. Phytochemistry, 54, 281–287 (2000).

    Article  CAS  PubMed  Google Scholar 

  • Liu, L. F., DNA topoisomerase poisons as antitumor drugs. Annu. Rev. Biochem., 58, 351–375 (1989).

    Article  CAS  PubMed  Google Scholar 

  • Nakatani, N., Ikeda, K., Kikuzaki, H., Kido, M., and Yamaguchi, Y., Diaryldimethylbutane lignans from Myristica argentea and their antimicrobial action against Streptococcus mutans. Phytochemistry, 27, 3127–3129 (1988).

    Article  CAS  Google Scholar 

  • Pommier, Y., DNA topoisomerase I and II in cancer chemotherapy: update and perspectives. Cancer Chemother. Pharmacol., 32, 103–108 (1993).

    Article  CAS  PubMed  Google Scholar 

  • Potmesil, M., Camptothecins: from bench research to hospital wards. Cancer Res., 54, 1431–1439 (1994).

    CAS  PubMed  Google Scholar 

  • Rajbhandari, I., Takamatsu, S., and Nagle, D. G., A new dehydrogeranylgeraniol antioxidant from Saururus cernuus that inhibits intracellular reactive oxygen species (ROS)-catalyzed oxidation within HL-60 cells. J. Nat. Prod., 64, 693–695 (2001).

    Article  CAS  PubMed  Google Scholar 

  • Rao, K. V. and Alvarez, F. M., Chemistry of Saururus cernuus. I. Saucernetin, a new neolignan. J. Nat. Prod., 45, 393–397 (1982).

    Article  CAS  Google Scholar 

  • Rao, K. V. and Alvarez F. M., Chemistry of Saururus cernuus III: Some reactions the diarylbutane-type neolignans. J. Nat. Prod., 48, 592–597 (1985).

    Article  CAS  Google Scholar 

  • Rao, K. V. and Alvarez, F. M., Manassantins A/B and saucerneol: novel biologically active lignoids from Saururus cernuus. Tetrahedron Lett., 24, 4947–4950 (1983).

    Article  CAS  Google Scholar 

  • Rao, K. V., Puri, V. N., Diwan, P. K., and Alvarez, F. M., Preliminary evaluation of manassantin A, a potential neuroleptic agent from Saururus cernuus. Pharmacol. Res. Commun., 19, 629–638 (1987).

    Article  CAS  PubMed  Google Scholar 

  • Rao, K. V. and Rao, N. S. P., Chemistry of Saururus cernuus, VI: Three new neolignans J. Nat. Prod., 53, 212–215 (1990).

    Article  CAS  PubMed  Google Scholar 

  • Rao, K. V. and Reddy, G. C. S., Chemistry of Saururus cernuus, V. Sauristolactam and other nitrogenous constituents. J. Nat. Prod., 53, 309–312 (1990).

    Article  CAS  PubMed  Google Scholar 

  • Rao, K. V. and Oruganty, R. S., An improved method for the isolation of the lignan constituents of Saururus cernuus by reverse phase column chromatography. J. Liq. Chrom. & Rel. Technol., 20, 3121–3134 (1997).

    Article  CAS  Google Scholar 

  • Rubinstein, L. V., Shoemaker, R. H., Paul, K. D., Simon, R. M., Tosini, S., Skehan, P., Scudiero, D. A., Monks, A., and Boyd, M. R., Comparison of in vitro anticancer drug screening data generated with a tetrazolium assay versus a protein assay against a diverse panel of human tumor cell lines. J. Nat. Cancer Inst., 82, 1113–1118 (1990).

    Article  CAS  PubMed  Google Scholar 

  • Seo, C. S., Lee, Y. K., Kim, Y. J., Jung, J. S., Jahng, Y. D., Chang, H. W., Song, D. K., and Son, J. K., Protective effect of lignans against sepsis from the roots of Saururus chinensis. Biol. Pharm. Bull., 31, 523–526 (2008).

    Article  CAS  PubMed  Google Scholar 

  • Seo, C. S., Zheng, M. S., Woo, M. H., Lee, C. S., Lee, S. H., Jeong, B. S., Chang, H. W., Jahng, Y. D., Lee, E. S., and Son, J. K., Lignans from the roots of Saururus chinensis. J. Nat. Prod., 71, 1771–1774 (2008).

    Article  CAS  PubMed  Google Scholar 

  • Shimomura, H., Sashida, Y., and Oohara, M., Lignans from Machilus thunbergii. Phytochemistry, 26, 1513–1515 (1987).

    Article  CAS  Google Scholar 

  • Shimomura, H., Sashida, Y., and Oohara M., Lignans from Machilus thunbergii. Phytochemistry, 27, 634–636 (1988).

    Article  CAS  Google Scholar 

  • Slichenmyer, W. J., Rowinsky, E. K., Donehower, R. C., and Kaufmann, S. H., The current status of camptothecin analogues as antitumor agents. J. Natl. Cancer Inst., 85, 271–291 (1993).

    Article  CAS  PubMed  Google Scholar 

  • Sung, S. H. and Kim, Y. C., Hepatoprotective diastereomeric lignans from Saururus chinensis herbs. J. Nat. Prod., 63, 1019–1021 (2000).

    Article  CAS  PubMed  Google Scholar 

  • Sung, S. H., Kwon, S. H., Cho, N. J., and Kim, Y. C., Hepatoprotective flavonol glycosides of Saururus chinensis herbs. Phytother. Res., 11, 500–503 (1997).

    Article  CAS  Google Scholar 

  • Wang, E. C., Shih, M. H., Liu, M. C., Chen, M. T., and Lee, G. H., Studies on constituents of Saururus chinensis. Heterocycles, 43, 969–975 (1996).

    Article  CAS  Google Scholar 

  • Wang, J. C., DNA topoisomerases. Annu. Rev. Biochem., 65, 635–692 (1996).

    Article  CAS  PubMed  Google Scholar 

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Correspondence to Jong-Keun Son.

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Yeun-Kyung Lee and Chang-Seob Seo contribated equally to this work.

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Lee, YK., Seo, CS., Lee, CS. et al. Inhibition of DNA topoisomerases I and II and cytotoxicity by lignans from Saururus chinensis . Arch. Pharm. Res. 32, 1409–1415 (2009). https://doi.org/10.1007/s12272-009-2010-7

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  • DOI: https://doi.org/10.1007/s12272-009-2010-7

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