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2013 , Vol. 33 >Issue 06: 1279 - 1283

DOI: https://doi.org/10.6023/cjoc201303035

研究论文

白藜芦醇衍生物的合成及抑制宫颈癌HeLa细胞肿瘤活性

  • 杜成 ,
  • 任玉杰 ,
  • 王庆伟 ,
  • 金鹭
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  • a 上海应用技术学院化学与环境工程学院 上海 201418;
    b 中国科学院上海有机化学研究所 天然产物有机合成化学重点实验室 上海 200032

收稿日期: 2013-03-23

  修回日期: 2013-04-26

  网络出版日期: 2013-05-06

基金资助

上海市教委科研创新重点(No.12ZZ188);上海市科委(No.11430502500);上海高校特聘教授(东方学者)岗位计划(No.405ZK110060002)资助项目.

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Synthesis and Anti-tumor Activities of Resveratrol Derivatives on Cervical Cancer HeLa Cells

  • Du Cheng ,
  • Ren Yujie ,
  • Wang Qingwei ,
  • Jin Lu
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  • a School of Chemical and Environmental Engineering, Shanghai Institute of Technology, Shanghai 201418;
    b Key Laboratory Synthetic Chemistry of Natural Substances, Shanghai Institute of Organic Chemistry, Chinese Academy of Sciences, Shanghai 200032

Received date: 2013-03-23

  Revised date: 2013-04-26

  Online published: 2013-05-06

Supported by

Project Supported by the Innovation Program of Shanghai Municipal Education Commission (No.12ZZ188), the Science and Technology Commission of Shanghai Municipal (No.11430502500), the Professor of Special Appointment (Eastern Scholar) at Shanghai Institutions of Higher Learning (No.405ZK110060002).

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摘要

以白藜芦醇、氯乙酰氯、对甲苯磺酰氯、对甲苯甲酰氯为原料, 合成9种新的白藜芦醇衍生物, 其结构经IR, 1H NMR, 13C NMR和HRMS所表征.用3-(4,5-二甲基噻唑-2)-2,5-二苯基四氮唑溴盐(MTT)法测试了目标化合物抑制宫颈癌HeLa细胞的肿瘤活性, 结果表明: 化合物4a, 6a, 7b, 8b和11c对HeLa细胞的抑制活性比白藜芦醇高, 其中化合物6a和8b的抑制效果最明显, 其IC50值分别为22.7和18.0 μmol/L, 活性高于白藜芦醇(IC50=114 μmol/L), 且在150 μmol/L浓度下对HeLa细胞的抑制率达95.5%和87.7%.

关键词： 白藜芦醇; 衍生物; 合成; HeLa细胞; 抗肿瘤活性

本文引用格式

杜成 , 任玉杰 , 王庆伟 , 金鹭 . 白藜芦醇衍生物的合成及抑制宫颈癌HeLa细胞肿瘤活性[J]. 有机化学, 2013 , 33(06) : 1279 -1283 . DOI: 10.6023/cjoc201303035

Abstract

Nine novel resveratrol derivatives were synthesized from resveratrol, chloroacetyl chloride, p-toluenesulfonyl chloride and p-methyl benzoyl chloride.These structures were confirmed by IR, 1H NMR, 13C NMR and HR-MS techniques.The target compounds were evaluated for their anti-tumor activities against cervical cancer HeLa cells by 3-(4,5-dimethylthi- azol-2-yl)-2,5-diphenyltetrazolium bromide (MTT) method, and the results indicated that compounds 4a, 6a, 7b, 8b and 11c of all the derivatives displayed better activities than resveratrol against HeLa cells, the compounds 6a and 8b displayed excellent inhibition effect, with IC50 values of 22.7 and 18.0 μmol/L, respectively, even higher than that of resveratrol (IC50=114 μmol/L).The inhibitory ratio of compounds 6a and 8b were 95.5% and 87.7% against HeLa cells at the concentration of 150 μmol/L.

Key words： resveratrol; derivative; synthesis; HeLa cell; anti-tumor activities

参考文献

[1] Pan, M.H.; Lin, C.L.; Tsai, J.H.; Ho, C.T.; Chen, W.J.J.Agric.Food Chem.2010, 58, 226.
[2] Juan, M.E.; Wenzel, U.; Daniel, H.; Planas, J.M.J.Agric.Food Chem.2008, 56, 4813.
[3] Kundu, J.K.; Surh, Y.J.Cancer Lett.2008, 269, 243.
[4] Selvaraj, S.; Mohan, A.; Narayanan, S.; Sethuraman, S.; Krishnan, U.M.J.Med.Chem.2013, 56, 970.
[5] Agrawal, M.; Kumar, V.; Singh, A.K.; Kashyap, M.P.; Khanna, V.K.; Siddiqui, M.A.; Pant, A.B.ACS Chem.Neurosci.2013, 4, 285.
[6] Udenigwe, C.C.; Ramprasath, V.R.; Aluko, R.E.; Jones, P.J.H.Nutr.Rev.2008, 66, 445.
[7] Li, L.; Henry, G.E.; Seeram, N.P.J.Agric.Food Chem.2009, 57, 7282.
[8] Yap, S.; Qin, C.X.; Woodman, O.L.Biofactors 2010, 36, 350.
[9] Albani, D.; Polito, L.; Signorini, A.; Forloni, G.Biofactors 2010, 36, 370.
[10] Bishayee, A.; Darvesh, A.S.; Politis, T.; McGory, R.Liver Int.2010, 30, 1103.
[11] Joseph, J.A.Fisher D.R.; Cheng, V.; Rimando, A.M.; Shukitt-Hale, B.J.Agric.Food Chem.2008, 56, 10544.
[12] Mouchiroud, L.; Molin, L.; Dallière, N.; Solari, F.Biofactors 2010, 36, 377.
[13] Chen, W.P.; Hung, L.M.; Hsueh, C.H.; Lai, L.P.; Su, M.J.Br.J.Pharmacol.2009, 157, 381.
[14] Zhu, Z.Q.; Zhang, X.Y.; Chen, J.W.; Xia, J.; Zhai, W.G.; Hu, T.X.J.East China Normal Univ.(Nat.Sci) 2002, 2, 98 (in Chinese).(朱振勤, 张小轶, 陈季武, 夏晶, 翟万垠, 胡天喜, 华东师范大学学报(自然科学版), 2002, 2, 98.)
[15] Liu, S.J.; Hu, Y.L.; Wang, X.L.; Zhong, J.; Lin, Z.P.J.Agric.Food Chem.2006, 54, 8082.
[16] Reddy, M.A.; Jain, N.; Yada, D.; Kishore, C.; Vangala, J.R.; P.Surendra R.; Addlagatta, A.; Kalivendi, S.V.; Sreedhar, B.J.Med.Chem.2011, 54, 6751.
[17] Lv, Y.J.; Zhou, N.; Meng, Q.G.J.Int.Pharm.Res.2008, 35, 377.(in Chinese).(吕玉健, 周宁, 孟庆国, 国际药学杂志, 2008, 35, 377.)
[18] Liu, H.C.; Dong, A.J.; Gao, C.M.; Jiang, Y.Y.Prog.Chem.2009, 21, 1500 (in Chinese).(刘华臣, 董爱君, 高春梅, 蒋宇扬, 化学进展, 2009, 21, 1500.)
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