Abstract
A series of novel bergenin derivatives based on alcoholic hydroxyl group(s) modifications have been designed, synthesized and their cytotoxic activities against two human cancer cell lines including K562 and HL60 were evaluated. Over half of the tested derivatives, mainly with nitrogen containing moieties, displayed strong activities against K562 and HL60 cell lines.
Graphical Abstract
Similar content being viewed by others
References
Chen JB, Sun ZX, Zhang YL, Zeng XH, Qing C, Liu JP, Li L, Zhang HB (2009) Synthesis of gibberellin derivatives with anti-tumor bioactivities. Bioorg Med Chem Lett 19:5496–5499
De Silva SL, De Oliveira VG (2009) Antimicrobial activity of bergenin from Endopleura uchi (huber) cuatrec. Acta Amazonica 39:187–192
DeOliveira CM, Nonato FR, DeLima FO, Couto RD, David JP, David JM, Soares MBP, Villarreal CF (2011) Antinociceptive properties of bergenin. J Nat Prod 74:2062–2068
Goel RK, Maiti RN, Manickam M, Ray AB (1997) Antiulcer activity of naturally occurring pyrano-coumarin and isocoumarins and their effect on prostanoid synthesis using human colonic mucosa. Indian J Exp Biol 35:1080–1083
Jahromi MAF, Chansouria JPN, Ray AB (1992) Hypolipidaemic activity in rats of bergenin, the major constituent of Flueggea microcarpa. Phytother Res 6:180–183
Jung JC, Lim E, Kim SH, Kim NS, Jung M, Oh S (2011) Practical synthesis and biological evaluation of bergenin analogs. Chem Biol Drug Des 78:725–729
Kashima Y, Miyazawa M (2012) Synthesis and biological evaluation of bergenin analogues as mushroom tyrosinase inhibitors. Arch Pharm Res 35:1533–1541
Kim DK, Ryu DH, Lee JY, Lee N, Kim YW, Kim JS, Chang K, Im GJ, Kim TK, Choi WS (2012) Synthesis and biological evaluation of novel A-ring modified hexacyclic camptothecin analogues. J Med Chem 44:1594–1602
Kumar TV, Tiwari AK, Robinson A, Babu KS, Kumar RSC, Kumar DA, Zehra A, Rao JM (2011) Synthesis and antiglycation potentials of bergenin derivatives. Bioorg Med Chem Lett 21:4928–4931
Lim HK, Kim HS, Choi HS, Oh S, Choi J (2000) Hepatoprotective effects of bergenin, a major constituent of mallotus japonicus, on carbon tetrachloride-intoxicated rats. J Ethnopharmacol 72:469–474
Mishima S, Matsumoto K, Futamura Y, Araki Y, Ito T, Tanaka T, Iinuma M, Nozawa Y, Akao Y (2003) Antitumor effect of stilbenoids from Vateria indica against allografted sarcoma S-180 in animal model. J Exp Ther Oncol 3:283–288
Nazir N, Koul S, Qurishi MA, Taneja SC, Ahmad SF, Bani S, Qazi GN (2007) Immunomodulatory effect of bergenin and norbergenin against adjuvant-induced arthritis: a flow cytometric study. J Ethnopharmacol 112:401–405
Nazir N, Koul S, Qurishi MA, Najar MH, Zargar MI (2011) Evaluation of antioxidant and antimicrobial activities of bergenin and its derivatives obtained by chemoenzymatic synthesis. Eur J Med Chem 46:2415–2420
Nunomura RCS, Oliveira VG, Da Silva SL, Nunomura SM (2009) Characterization of bergenin in Endopleura uchi bark and its anti-infammatory activity. J Braz Chem Soc 20:1060–1064
Piacente S, Pizza C, Detommasi N, Mahmood N (1996) Constituents of Ardisia japonica and their in vitro anti-HIV activity. J Nat Prod 59:565–569
Popov SV, Popova GY, Nikolaeva SY, Golovchenko VV, Ovodova RG (2005) Immunostimulating activity of pectic polysaccharide from Bergenia crassifolia. Phytother Res 19:1052–1056
Pu HL, Huang X, Zhao JH, Hong A (2002) Bergenin is the antiarrhythmic principle of Fluggea virosa. Planta Med 68:372–374
Swarnalakshmi T, Sethuraman MG, Sulochana N, Arivudainambi R (1984) A note on the antiinflammatory activity of bergenin. Curr Sci 53:917–919
Takahashi H, Kosaha M, Watanabe Y, Nakade K, Fukuyama Y (2003) Synthesis and neuroprotective activity of bergenin derivatives with antioxidant activity. Bioorg Med Chem 11:1781–1788
Wang R, Shi HF, Zhao JF, He YP, Zhang HB, Liu JP (2013) Design, synthesis and aromatase inhibitory activities of novel indole–imidazole derivatives. Bioorg Med Chem Lett 23:1760–1762
Acknowledgments
This research was supported by the National Natural Science Foundation of China (Grant No. 20562012, 21162033).
Author information
Authors and Affiliations
Corresponding author
Additional information
Na–Na Liu and Fu-Kai Bao have contributed equally to this paper.
Rights and permissions
About this article
Cite this article
Liu, NN., Bao, FK., Chen, JB. et al. Synthesis and cytotoxic activities of novel bergenin derivatives. Med Chem Res 23, 4803–4813 (2014). https://doi.org/10.1007/s00044-014-1050-9
Received:
Accepted:
Published:
Issue Date:
DOI: https://doi.org/10.1007/s00044-014-1050-9