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Volumn 9, Issue 3, 2014, Pages

Evaluation and structure-activity relationship analysis of a new series of arylnaphthalene lignans as potential anti-tumor agents

Author keywords

[No Author keywords available]

Indexed keywords

6' HYDROXYJUSTICIDIN A; 6' HYDROXYJUSTICIDIN B; ANTINEOPLASTIC AGENT; ARYLNAPHTHALENE LIGNAN DERIVATIVE; CASPASE 3; CHINENSINAPHTHOL METHYL ETHER; ETOPOSIDE; JUSTICIDIN B; LIGNAN DERIVATIVE; PACLITAXEL; PODOPHYLLOTOXIN; SUPEROXIDE DISMUTASE; TAIWANIN E METHYL ETHER; UNCLASSIFIED DRUG; 1,3 DIOXOLANE DERIVATIVE; JUSTICIDIN A; LIGNAN; NAPHTHALENE DERIVATIVE;

EID: 84899870087     PISSN: None     EISSN: 19326203     Source Type: Journal    
DOI: 10.1371/journal.pone.0093516     Document Type: Article
Times cited : (31)

References (45)
  • 2
    • 33746669381 scopus 로고    scopus 로고
    • Cytotoxic arylnaphthalene lignans from Phyllanthus oligospermus
    • Tokyo
    • Wu SJ, Wu TS (2006) Cytotoxic arylnaphthalene lignans from Phyllanthus oligospermus. Chem Pharm Bull (Tokyo) 54: 1223-1225.
    • (2006) Chem Pharm Bull , vol.54 , pp. 1223-1225
    • Wu, S.J.1    Wu, T.S.2
  • 3
    • 0027288674 scopus 로고
    • Antitumor activity of a new low immunosuppressive derivative of podophyllotoxin (GP-11) and its mechanisms
    • Wang JZ, Tian X, Tsumura H, Shimura K, Ito H (1993) Antitumor activity of a new low immunosuppressive derivative of podophyllotoxin (GP-11) and its mechanisms. Anticancer Drug Des 8: 193-202. (Pubitemid 23198420)
    • (1993) Anti-Cancer Drug Design , vol.8 , Issue.3 , pp. 193-202
    • Wang, J.-Z.1    Tian, X.2    Tsumura, H.3    Shimura, K.4    Ito, H.5
  • 7
    • 0030989428 scopus 로고    scopus 로고
    • A one-pot, efficient synthesis of the potent cytotoxic podophyllotoxin derivative NPF
    • DOI 10.1016/S0040-4039(97)00450-4, PII S0040403997004504
    • Daley L, Meresse P, Bertounesque E, Monneret C (1997) A one-pot, efficient synthesis of the potent cytotoxic podophyllotoxin derivative NPF. Tetrahedron Lett 38: 2673-2676. (Pubitemid 27154363)
    • (1997) Tetrahedron Letters , vol.38 , Issue.15 , pp. 2673-2676
    • Daley, L.1    Meresse, P.2    Bertounesque, E.3    Monneret, C.4
  • 8
    • 0033583155 scopus 로고
    • A high yield preparation of 2-fluoropodophyllotoxin
    • Van Vliet DS, Lee KH (1990) A high yield preparation of 2-fluoropodophyllotoxin. Tetrahedron Lett 40: 2259-2262.
    • (1990) Tetrahedron Lett , vol.40 , pp. 2259-2262
    • Van Vliet, D.S.1    Lee, K.H.2
  • 10
    • 0034018817 scopus 로고    scopus 로고
    • In vitro evaluation of GL331's cancer cell killing and apoptosis- inducing activity in combination with other chemotherapeutic agents
    • DOI 10.1023/A:1009693811093
    • Huang TS, Shu CH, Lee CC, Chen LT, Whang-Peng J (2000) In vitro evaluation of GL331's cancer cell killing and apoptosis-inducing activity in combination with other chemotherapeutic agents. Apoptosis 5: 79-85. (Pubitemid 30146393)
    • (2000) Apoptosis , vol.5 , Issue.1 , pp. 79-85
    • Huang, T.-S.1    Shu, C.-H.2    Lee, C.-C.3    Chen, L.-T.4    Whang-Peng, J.5
  • 11
    • 0034858972 scopus 로고    scopus 로고
    • A novel topoisomerase II poison GL331 preferentially induces DNA cleavage at (C/G) T sites and can cause telomere DNA damage
    • Lee CC, Huang TS (2001) A novel topoisomerase II poison GL331 preferentially induces DNA cleavage at (C/G) T sites and can cause telomere DNA damage. Pharm Res 18: 846-851.
    • (2001) Pharm Res , vol.18 , pp. 846-851
    • Lee, C.C.1    Huang, T.S.2
  • 12
    • 0034802324 scopus 로고    scopus 로고
    • GL331 induces down-regulation of cyclin D1 expression via enhanced proteolysis and repressed transcription
    • Lin SK, Huang HC, Chen LL, Lee CC, Huang TS (2001) GL331 induces down-regulation of cyclin D1 expression via enhanced proteolysis and repressed transcription. Mol Pharmacol 60: 768-775.
    • (2001) Mol Pharmacol , vol.60 , pp. 768-775
    • Lin, S.K.1    Huang, H.C.2    Chen, L.L.3    Lee, C.C.4    Huang, T.S.5
  • 13
    • 0036244606 scopus 로고    scopus 로고
    • F 11782, a novel catalytic inhibitor of topoisomerases I and II, induces atypical, yet cytotoxic DNA double-strand breaks in CHO-K1 cells
    • Barret JM, Etievant C, Baudouin C, Skov K, Charveron M, et al. (2002) F 11782, a novel catalytic inhibitor of topoisomerases I and II, induces atypical, yet cytotoxic DNA double-strand breaks in CHO-K1 cells. Anticancer Res 22: 187-192. (Pubitemid 34475296)
    • (2002) Anticancer Research , vol.22 , Issue.1 A , pp. 187-192
    • Barret, J.-M.1    Etievant, C.2    Baudouin, C.3    Skov, K.4    Charveron, M.5    Hill, B.T.6
  • 15
    • 0021882365 scopus 로고
    • Anti-inflammatory effect of neolignans newly isolated from the crude drug 'Shin-i' (Flos magnoliae)
    • Kimura M, Suzuki J, Yamada T, Yoshizaki M, Kikuchi T, et al. (1985) Anti-inflammatory effect of neolignans newly isolated from the crude drug "Shin-I" (Flos Magnoliae). Planta Med 51: 291-293. (Pubitemid 15014322)
    • (1985) Planta Medica , vol.NO. 4 , pp. 291-293
    • Kimura, M.1    Suzuki, J.2    Yamada, T.3
  • 16
    • 64649090292 scopus 로고    scopus 로고
    • Targeting DNA topoisomerase II in cancer chemotherapy
    • Nitiss JL (2009) Targeting DNA topoisomerase II in cancer chemotherapy. Nat Rev Cancer 9: 338-350.
    • (2009) Nat Rev Cancer , vol.9 , pp. 338-350
    • Nitiss, J.L.1
  • 18
    • 33646595001 scopus 로고    scopus 로고
    • Caspase-8 acts as a key upstream executor of mitochondria during justicidin A-induced apoptosis in human hepatoma cells
    • DOI 10.1016/j.febslet.2006.04.085, PII S0014579306005321
    • Su CL, Huang LL, Huang LM, Lee JC, Lin CN, et al. (2006) Caspase-8 acts as a key upstream executor of mitochondria during justicidin A-induced apoptosis in human hepatoma cells. FEBS Lett 580: 3185-3191. (Pubitemid 43729674)
    • (2006) FEBS Letters , vol.580 , Issue.13 , pp. 3185-3191
    • Su, C.-L.1    Huang, L.L.H.2    Huang, L.-M.3    Lee, J.-C.4    Lin, C.-N.5    Won, S.-J.6
  • 19
    • 0036196281 scopus 로고    scopus 로고
    • Potent cytotoxic lignans from Justicia procumbens and their effects on nitric oxide and tumor necrosis factor-alpha production in mouse macrophages
    • Day SH, Lin YC, Tsai ML, Tsao LT, Ko HH, et al. (2002) Potent cytotoxic lignans from Justicia procumbens and their effects on nitric oxide and tumor necrosis factor-alpha production in mouse macrophages. J Nat Prod 65: 379-381.
    • (2002) J Nat Prod , vol.65 , pp. 379-381
    • Day, S.H.1    Lin, Y.C.2    Tsai, M.L.3    Tsao, L.T.4    Ko, H.H.5
  • 20
    • 0022454593 scopus 로고
    • Antitumor agents, 81. Justicidin-A and diphyllin, two cytotoxic principles from Justicia procumbens
    • Fukamiya N, Lee KH (1986) Antitumor agents, 81. Justicidin-A and diphyllin, two cytotoxic principles from Justicia procumbens. J Nat Prod 49: 348-350. (Pubitemid 16068777)
    • (1986) Journal of Natural Products , vol.49 , Issue.2 , pp. 348-350
    • Fukamiya, N.1    Lee, K.-H.2
  • 21
  • 22
    • 77954357835 scopus 로고    scopus 로고
    • Effect of 6′-hydroxy justicidin A on cell proliferation and redox system in tumor cells
    • Zhang P, Zhou WQ, Dong XZ, Yang MH, Bi MG (2010) Effect of 6′-hydroxy justicidin A on cell proliferation and redox system in tumor cells. Chin J Pharmacol Toxicol 24: 207-213.
    • (2010) Chin J Pharmacol Toxicol , vol.24 , pp. 207-213
    • Zhang, P.1    Zhou, W.Q.2    Dong, X.Z.3    Yang, M.H.4    Bi, M.G.5
  • 23
    • 84866249017 scopus 로고    scopus 로고
    • In vitro anti-tumor mechanism of JR6 on human colon cancer cell HT-29
    • Deng JY, Yang MH, Bi MG (2009) In vitro anti-tumor mechanism of JR6 on human colon cancer cell HT-29. Chin Pharmacol Bull 25: 190-191.
    • (2009) Chin Pharmacol Bull , vol.25 , pp. 190-191
    • Deng, J.Y.1    Yang, M.H.2    Bi, M.G.3
  • 24
    • 18744407303 scopus 로고    scopus 로고
    • In vitro antileishmanial activity of diphyllin isolated from Haplophyllum bucharicum
    • DOI 10.1055/s-2005-864106
    • Di Giorgio C, Delmas F, Akhmedjanova V, Ollivier E, Bessonova I, et al. (2005) In vitro antileishmanial activity of diphyllin isolated from Haplophyllum bucharicum. Planta Med 71: 366-369. (Pubitemid 40676465)
    • (2005) Planta Medica , vol.71 , Issue.4 , pp. 366-369
    • Di, G.C.1    Delmas, F.2    Akhmedjanova, V.3    Ollivier, E.4    Bessonova, I.5    Riad, E.6    Timon-David, P.7
  • 25
    • 0001364671 scopus 로고    scopus 로고
    • Antiviral activity of lignans and their glycosides from Justicia procumbens
    • DOI 10.1016/0031-9422(96)00024-6
    • Asano J, Chiba K, Tada M, Yoshii T (1996) Antiviral activity of lignans and their glycosides from Justicia procumbens. Phytochemistry 42: 713-717. (Pubitemid 27096873)
    • (1996) Phytochemistry , vol.42 , Issue.3 , pp. 713-717
    • Asano, J.1    Chiba, K.2    Tada, M.3    Yoshii, T.4
  • 26
    • 0030444099 scopus 로고    scopus 로고
    • Antiplatelet arylnaphthalide lignans from Justicia procumbens
    • Chen CC, Hsin WC, Ko FN, Huang YL, Ou JC, et al. (1996) Antiplatelet arylnaphthalide lignans from Justicia procumbens. J Nat Prod 59: 1149-1150.
    • (1996) J Nat Prod , vol.59 , pp. 1149-1150
    • Chen, C.C.1    Hsin, W.C.2    Ko, F.N.3    Huang, Y.L.4    Ou, J.C.5
  • 27
    • 84868198917 scopus 로고    scopus 로고
    • JR6, a new compound isolated from Justicia procumbens, induces apoptosis in human bladder cancer EJ cells through caspase-dependent pathway
    • He XL, Zhang P, Dong XZ, Yang MH, Chen SL, et al. (2012) JR6, a new compound isolated from Justicia procumbens, induces apoptosis in human bladder cancer EJ cells through caspase-dependent pathway. J Ethnopharmacol 144: 284-292.
    • (2012) J Ethnopharmacol , vol.144 , pp. 284-292
    • He, X.L.1    Zhang, P.2    Dong, X.Z.3    Yang, M.H.4    Chen, S.L.5
  • 28
    • 33745726015 scopus 로고    scopus 로고
    • 13C NMR data for seven arylnaphthalide lignans from Justicia procumbens
    • 13C NMR data for seven arylnaphthalide lignans from Justicia procumbens. Magn Reson Chem 44: 727-730.
    • (2006) Magn Reson Chem , vol.44 , pp. 727-730
    • Yang, M.1    Wu, J.2    Cheng, F.3    Zhou, Y.4
  • 29
    • 33645997053 scopus 로고    scopus 로고
    • A new lignan from the Jian-er syrup and its content determination by RP-HPLC
    • Yang M, Wu J, Xu X, Jin Y, Guo Y, et al. (2006b) A new lignan from the Jian-er syrup and its content determination by RP-HPLC. J Pharm Biomed Anal 41: 662-666.
    • (2006) J Pharm Biomed Anal , vol.41 , pp. 662-666
    • Yang, M.1    Wu, J.2    Xu, X.3    Jin, Y.4    Guo, Y.5
  • 30
    • 84873704641 scopus 로고    scopus 로고
    • Simultaneous determination of seven lignans in Justicia procumbens by high performance liquid chromatography-photodiode array detection using relative response factors
    • Luo Z, Kong W, Qiu F, Yang M, Li Q, et al. (2013) Simultaneous determination of seven lignans in Justicia procumbens by high performance liquid chromatography-photodiode array detection using relative response factors. J Sep Sci 36: 699-705.
    • (2013) J Sep Sci , vol.36 , pp. 699-705
    • Luo, Z.1    Kong, W.2    Qiu, F.3    Yang, M.4    Li, Q.5
  • 31
    • 0032575752 scopus 로고    scopus 로고
    • Mitochondria and apoptosis
    • Green DR, Reed JC (1998) Mitochondria and apoptosis. Science 281: 1309-1312. (Pubitemid 28406816)
    • (1998) Science , vol.281 , Issue.5381 , pp. 1309-1312
    • Green, D.R.1    Reed, J.C.2
  • 32
    • 0034614637 scopus 로고    scopus 로고
    • The hallmarks of cancer
    • Hanahan D, Weinberg RA (2000) The hallmarks of cancer. Cell 100: 57-70. (Pubitemid 30046295)
    • (2000) Cell , vol.100 , Issue.1 , pp. 57-70
    • Hanahan, D.1    Weinberg, R.A.2
  • 33
    • 0036130889 scopus 로고    scopus 로고
    • Apoptosis and cancer: When Bax is TRAILing away
    • DOI 10.1038/nm0302-216
    • Roth W, Reed JC (2002) Apoptosis and cancer: When BAX is TRAILing away. Nat Med 8: 216-218. (Pubitemid 34250094)
    • (2002) Nature Medicine , vol.8 , Issue.3 , pp. 216-218
    • Roth, W.1    Reed, J.C.2
  • 34
    • 0036086130 scopus 로고    scopus 로고
    • Free radicals in the physiological control of cell function
    • Droge W (2002) Free radicals in the physiological control of cell function. Physiol Rev 82: 47-95.
    • (2002) Physiol Rev , vol.82 , pp. 47-95
    • Droge, W.1
  • 35
    • 60749108379 scopus 로고    scopus 로고
    • Regulation of autophagy by reactive oxygen species (ROS): Implications for cancer progression and treatment
    • Azad MB, Chen Y, Gibson SB (2009) Regulation of autophagy by reactive oxygen species (ROS): implications for cancer progression and treatment. Antioxid Redox Signal 11: 777-790.
    • (2009) Antioxid Redox Signal , vol.11 , pp. 777-790
    • Azad, M.B.1    Chen, Y.2    Gibson, S.B.3
  • 36
    • 0029068871 scopus 로고
    • Identification and inhibition of the ICE/CED-3 protease necessary for mammalian apoptosis
    • Nicholson DW, Ali A, Thornberry NA, Vaillancourt JP, Ding CK, et al. (1995) Identification and inhibition of the ICE/CED-3 protease necessary for mammalian apoptosis. Nature 376: 37-43.
    • (1995) Nature , vol.376 , pp. 37-43
    • Nicholson, D.W.1    Ali, A.2    Thornberry, N.A.3    Vaillancourt, J.P.4    Ding, C.K.5
  • 37
    • 33747432610 scopus 로고    scopus 로고
    • Production of justicidin B, a cytotoxic arylnaphthalene lignan from genetically transformed root cultures of Linum leonii
    • Vasilev N, Elfahmi, Bos R, Kayser O, Momekov G, et al. (2006) Production of justicidin B, a cytotoxic arylnaphthalene lignan from genetically transformed root cultures of Linum leonii. J Nat Prod 69: 1014-1017.
    • (2006) J Nat Prod , vol.69 , pp. 1014-1017
    • Vasilev, N.1    Elfahmi2    Bos, R.3    Kayser, O.4    Momekov, G.5
  • 38
    • 84899842955 scopus 로고    scopus 로고
    • Linum narbonense: A new valuable tool for biotechnological production of a potent anticancer lignan Justicidine B
    • Ionkova I, Sasheva P, Ionkov T, Momekov G (2013) Linum narbonense: A new valuable tool for biotechnological production of a potent anticancer lignan Justicidine B. Pharmacogn Mag 9: 39-44.
    • (2013) Pharmacogn Mag , vol.9 , pp. 39-44
    • Ionkova, I.1    Sasheva, P.2    Ionkov, T.3    Momekov, G.4
  • 39
    • 84866247911 scopus 로고    scopus 로고
    • LC-ESI-MS/MS analysis and pharmacokinetics of 6′-hydroxy justicidin A, a potential antitumor active component isolated from Justicia procumbens, in rats
    • Qiu F, Zhou S, Fu S, Kong W, Yang S, et al. (2012) LC-ESI-MS/MS analysis and pharmacokinetics of 6′-hydroxy justicidin A, a potential antitumor active component isolated from Justicia procumbens, in rats. J Pharm Biomed Anal 70: 539-543.
    • (2012) J Pharm Biomed Anal , vol.70 , pp. 539-543
    • Qiu, F.1    Zhou, S.2    Fu, S.3    Kong, W.4    Yang, S.5
  • 40
    • 84864927798 scopus 로고    scopus 로고
    • Application of a sensitive and specific LC-MS/MS method for determination of chinensinaphthol methyl ether in rat plasma for a bioavailability study
    • Zhou S, Qiu F, Tong Z, Yang S, Yang M (2012) Application of a sensitive and specific LC-MS/MS method for determination of chinensinaphthol methyl ether in rat plasma for a bioavailability study. J Chromatogr B Analyt Technol Biomed Life Sci 903: 75-80.
    • (2012) J Chromatogr B Analyt Technol Biomed Life Sci , vol.903 , pp. 75-80
    • Zhou, S.1    Qiu, F.2    Tong, Z.3    Yang, S.4    Yang, M.5
  • 41
    • 0027979832 scopus 로고
    • BCR-ABL maintains resistance of chronic myelogenous leukemia cells to apoptotic cell death
    • McGahon A, Bissonnette R, Schmitt M, Cotter KM, Green DR, et al. (1994) BCR-ABL maintains resistance of chronic myelogenous leukemia cells to apoptotic cell death. Blood 83: 1179-1187. (Pubitemid 24062839)
    • (1994) Blood , vol.83 , Issue.5 , pp. 1179-1187
    • McGahon, A.1    Bissonnette, R.2    Schmitt, M.3    Cotter, K.M.4    Green, D.R.5    Cotter, T.G.6
  • 42
    • 33847136330 scopus 로고    scopus 로고
    • Matrine upregulates the cell cycle protein E2F-1 and triggers apoptosis via the mitochondrial pathway in K562 cells
    • DOI 10.1016/j.ejphar.2006.12.017, PII S0014299907000040
    • Jiang H, Hou C, Zhang S, Xie H, Zhou W, et al. (2007) Matrine upregulates the cell cycle protein E2F-1 and triggers apoptosis via the mitochondrial pathway in K562 cells. Eur J Pharmacol 559: 98-108. (Pubitemid 46295409)
    • (2007) European Journal of Pharmacology , vol.559 , Issue.2-3 , pp. 98-108
    • Jiang, H.1    Hou, C.2    Zhang, S.3    Xie, H.4    Zhou, W.5    Jin, Q.6    Cheng, X.7    Qian, R.8    Zhang, X.9
  • 43
    • 75149138984 scopus 로고    scopus 로고
    • Modulation of intercellular ROS signaling of human tumor cells
    • Bechtel W, Bauer G (2009) Modulation of intercellular ROS signaling of human tumor cells. Anticancer Res 29: 4559-4570.
    • (2009) Anticancer Res , vol.29 , pp. 4559-4570
    • Bechtel, W.1    Bauer, G.2
  • 44
    • 0038018530 scopus 로고    scopus 로고
    • Apoptosis triggered redistribution of caspase-9 from cytoplasm to mitochondria
    • DOI 10.1016/S0014-5793(03)00494-0
    • Potokar M, Milisav I, Kreft M, Stenovec M, Zorec R (2003) Apoptosis triggered redistribution of caspase-9 from cytoplasm to mitochondria. FEBS Lett 544: 153-159. (Pubitemid 36628053)
    • (2003) FEBS Letters , vol.544 , Issue.1-3 , pp. 153-159
    • Potokar, M.1    Milisav, I.2    Kreft, M.3    Stenovec, M.4    Zorec, R.5
  • 45
    • 0031730202 scopus 로고    scopus 로고
    • Antiviral activity of lignans
    • Charlton JL (1998) Antiviral activity of lignans. J Nat Prod 61: 1447-1451.
    • (1998) J Nat Prod , vol.61 , pp. 1447-1451
    • Charlton, J.L.1


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