메뉴 건너뛰기




Volumn 22, Issue 9, 2012, Pages 977-997

Shikonin and its derivatives: A patent review

Author keywords

Anticancer; Cytotoxicity; Mechanism; Reactive oxygen species; Shikonin; Shikonin derivatives; Total synthesis

Indexed keywords

(DEXTRO) SHIKONIN; 5,8 DIACETOXYL 6(1' ACETOXYL 4' METHYL 3' PENTENYL) 1,4 NAPHTHAQUINONE; ACETYL SHIKONIN; ALKANIN; ALPHA METHYL N BUTYRYLSHIKONIN; ANTIINFLAMMATORY AGENT; ANTINEOPLASTIC AGENT; ARNEBIN 5; ARNEBINONE; BETA ACETOXYISOVALERYL SHIKONIN; BETA BETA DIMETHYLACRYLSHIKONIN; BETA HYDROXYISOVALERYL SHIKSONIN; FLUOROURACIL; HYPOXIA INDUCIBLE FACTOR 1; IMMUNOGLOBULIN ENHANCER BINDING PROTEIN; ISOBUTYRYLSHIKONIN; ISOVALERYLSHIKONIN; LITHOSPERMIDIN A; LITHOSPERMIDIN B; MITOGEN ACTIVATED PROTEIN KINASE; PROTEASOME; PROTEIN BAX; PROTEIN BCL XL; PROTEIN TYROSINE KINASE; REACTIVE OXYGEN METABOLITE; SHIKONIN; SHIKONIN DERIVATIVE; SHIKONIN GLUCOSAMINOSIDE; TERACRYL SHIKONIN; UNCLASSIFIED DRUG; UNINDEXED DRUG;

EID: 84865528891     PISSN: 13543776     EISSN: 17447674     Source Type: Journal    
DOI: 10.1517/13543776.2012.709237     Document Type: Review
Times cited : (78)

References (102)
  • 2
    • 0018824611 scopus 로고
    • Naturally occurring isohexenylnaphthazarin pigments: A new class of drugs
    • Papageorgiou VP. Naturally occurring isohexenylnaphthazarin pigments: A new class of drugs. Planta Med 1980;38:193-203 (Pubitemid 10065821)
    • (1980) Planta Medica , vol.38 , Issue.3 , pp. 193-203
    • Papageorgiou, V.P.1
  • 3
    • 0022450008 scopus 로고
    • A comparative study on anti-inflammatory activities of the enantiomers, shikonin and alkannin
    • Tanaka S, Tajima M. A comparative study on anti-inflammatory activities of the enantiomers, shikonin and alkannin. J Nat Prod 1986;49:466-9 (Pubitemid 16045809)
    • (1986) Journal of Natural Products , vol.49 , Issue.3 , pp. 466-469
    • Tanaka, S.1    Tajima, M.2    Tsukada, M.3    Tabata, M.4
  • 5
    • 0017462259 scopus 로고
    • Effect of topical application of the ether extracts and shiunko on inflammatory reactions
    • Hayashi M. Effect of topical application of the ether extracts and shiunko on inflammatory reactions. Nippon Yakurigaku Zasshi 1977;73:205-14
    • (1977) Nippon Yakurigaku Zasshi , vol.73 , pp. 205-214
    • Hayashi, M.1
  • 6
    • 0023830867 scopus 로고
    • In vitro stimulation of human granulocytes and lymphocytes by Pico- and Femtogram quantities of cytostastic agents
    • Wagner H, Kreher B, Jurcic K. In vitro stimulation of human granulocytes and lymphocytes by pico- and femtogram quantities of cytostastic agents. Arzneim Forsch Drug Res 1988;38:273-5 (Pubitemid 18045094)
    • (1988) Arzneimittel-Forschung/Drug Research , vol.38 , Issue.2 , pp. 273-275
    • Wagner, H.1    Kreher, B.2    Jurcic, K.3
  • 7
    • 0031867464 scopus 로고    scopus 로고
    • Shikonin, an ingredient of Lithospermum erythrorhizon, inhibits angiogenesis in vivo and in vitro
    • Hisa T, Kimura Y, Takada K, et al. Shikonin, an ingredient of lithospermum erythrorhizon, inhibits angiogenesis in vivo and in vitro. Anticaner Res 1998;18:783-90 (Pubitemid 28239595)
    • (1998) Anticancer Research , vol.18 , Issue.2 , pp. 783-790
    • Hisa, T.1    Kimura, Y.2    Takada, K.3    Suzuki, F.4    Takigawa, M.5
  • 8
    • 77955274349 scopus 로고    scopus 로고
    • Structure-radical scavenging activity relationship of alkannin/shikonin derivatives
    • Ordoudi AS, Tsermentseli SK, Nenadis N, et al. Structure-radical scavenging activity relationship of alkannin/shikonin derivatives. Food Chem 2011;124:171-6
    • (2011) Food Chem , vol.124 , pp. 171-176
    • Ordoudi, A.S.1    Tsermentseli, S.K.2    Nenadis, N.3
  • 9
    • 0027440561 scopus 로고
    • Inhibition of platelet aggregation by shikonin derivatives isolated from arnebia euchroma
    • Chang YS, Kuo SC, Weng SH, et al. Inhibition of platelet aggregation by shikonin derivatives isolated from arnebia euchroma. Planta Med 1993;59:401-3
    • (1993) Planta Med , vol.59 , pp. 401-403
    • Chang, Y.S.1    Kuo, S.C.2    Weng, S.H.3
  • 10
    • 84863115733 scopus 로고    scopus 로고
    • An efficient multigram synthesis of alkannin and shikonin
    • The first and most practical approach to obtain shikonin and its derivatives by chemical resolution
    • Wang R, Zhou S, Jiang HDGL, et al. An efficient multigram synthesis of alkannin and shikonin. Eur J Org Chem 2012;2012:1373-9. The first and most practical approach to obtain shikonin and its derivatives by chemical resolution.
    • (2012) Eur J Org Chem , vol.2012 , pp. 1373-1379
    • Wang, R.1    Zhou, S.2    Hdgl, J.3
  • 11
    • 34247109045 scopus 로고    scopus 로고
    • Natural products as sources of new drugs over the last 25 years
    • Newman DJ, Cragg GM. Natural products as sources of new drugs over the last 25 years. J Nat Prod 2007;70:461-7
    • (2007) J Nat Prod , vol.70 , pp. 461-467
    • Newman, D.J.1    Cragg, G.M.2
  • 12
    • 0028916381 scopus 로고
    • Acylshikonin analogs: Synthesis and inhibition of DNA topoisomerase-I
    • Ahn BZ, Baik KU, Kweon GR. Acylshikonin analogs: Synthesis and inhibition of DNA topoisomerase-I. J Med Chem 1995;38:1044-7
    • (1995) J Med Chem , vol.38 , pp. 1044-1047
    • Ahn, B.Z.1    Baik, K.U.2    Kweon, G.R.3
  • 13
    • 78649332634 scopus 로고    scopus 로고
    • Semi-synthesis and anti-tumor activity of 5,8-Odimethyl acylshikonin derivatives
    • Zhou W, Peng Y, Li S. Semi-synthesis and anti-tumor activity of 5,8-Odimethyl acylshikonin derivatives. Eur J Med Chem 2010;45:6005-11
    • (2010) Eur J Med Chem , vol.45 , pp. 6005-6011
    • Zhou, W.1    Peng, Y.2    Li, S.3
  • 14
    • 80052939147 scopus 로고    scopus 로고
    • Synthesis and antitumour activity of beta-hydroxyisovaleryl shikonin analogues
    • Rao Z, Liu X, Zhou W, et al. Synthesis and antitumour activity of beta-hydroxyisovaleryl shikonin analogues. Eur J Med Chem 2011;46:3934-41
    • (2011) Eur J Med Chem , vol.46 , pp. 3934-3941
    • Rao, Z.1    Liu, X.2    Zhou, W.3
  • 15
    • 80955179555 scopus 로고    scopus 로고
    • Semi-synthesis and antitumor activity of 6- isomers of 5,8-O-dimethyl acylshikonin derivatives
    • The modifications on the mother nucleus of shikonin to obtain related derivatives with higher selectivity and lower toxicity
    • Zhou W, Zhang X, Xiao L, et al. Semi-synthesis and antitumor activity of 6- isomers of 5,8-O-dimethyl acylshikonin derivatives. Eur J Med Chem 2011;46:3420-7. The modifications on the mother nucleus of shikonin to obtain related derivatives with higher selectivity and lower toxicity.
    • (2011) Eur J Med Chem , vol.46 , pp. 3420-3427
    • Zhou, W.1    Zhang, X.2    Xiao, L.3
  • 16
    • 79959955993 scopus 로고    scopus 로고
    • Cancer therapeutic agents targeting hypoxia-inducible factor-1
    • Wang R, Zhou S, Li S. Cancer therapeutic agents targeting hypoxia-inducible factor-1. Curr Med Chem 2011;18:3168-89
    • (2011) Curr Med Chem , vol.18 , pp. 3168-3189
    • Wang, R.1    Zhou, S.2    Li, S.3
  • 17
  • 18
    • 78149347324 scopus 로고    scopus 로고
    • An efficient synthesis of 1,4,5,8- tetrameth- oxy-2-naphthaldehyde
    • Wang RB, Zheng XG, Zhou W, et al. An efficient synthesis of 1,4,5,8- tetrameth- oxy-2-naphthaldehyde. J Chem Res 2010;34:520-1
    • (2010) J Chem Res , vol.34 , pp. 520-521
    • Wang, R.B.1    Zheng, X.G.2    Zhou, W.3
  • 20
    • 0008841335 scopus 로고
    • Cycloshikonin and its derivatives. A synthetic route of shikonin
    • Tanoue Y, Terada A, Sugyo Y. Cycloshikonin and its derivatives. A synthetic route of shikonin. J Org Chem 1987;52:1437-9
    • (1987) J Org Chem , vol.52 , pp. 1437-1439
    • Tanoue, Y.1    Terada, A.2    Sugyo, Y.3
  • 23
    • 0028841815 scopus 로고
    • Synthesis of dl-shikonin by vanadium (II)-assisted cross-coupling and electrooxidation of aromatic nuclei
    • Torii S, Akiyama K, Yamashita H, et al. Synthesis of dl-shikonin by vanadium (II)-assisted cross-coupling and electrooxidation of aromatic nuclei. Bull Chem Soc Jpn 1995;68:2917-22
    • (1995) Bull Chem Soc Jpn , vol.68 , pp. 2917-2922
    • Torii, S.1    Akiyama, K.2    Yamashita, H.3
  • 24
    • 0036002150 scopus 로고    scopus 로고
    • A simple synthesis of dl-shikonin
    • Lu Q, Duan W, Cai J. A simple synthesis of dl-shikonin. Chinese Chem Lett 2002;13:113-14
    • (2002) Chinese Chem Lett , vol.13 , pp. 113-114
    • Lu, Q.1    Duan, W.2    Cai, J.3
  • 25
    • 50149084698 scopus 로고    scopus 로고
    • Concise formal synthesis of (±)-shikonin via a highly alpha-regioselective prenylation of 1, 4, 5,8 - tetramethoxynaphthalene -2- carbaldehyde
    • Zhao LM, Xu DF, Zhou W, et al. Concise formal synthesis of (±)-shikonin via a highly alpha-regioselective prenylation of 1, 4, 5,8 - tetramethoxynaphthalene -2- carbaldehyde. Lett Org Chem 2008;5:234-6
    • (2008) Lett Org Chem , vol.5 , pp. 234-236
    • Zhao, L.M.1    Xu, D.F.2    Zhou, W.3
  • 26
    • 79953887253 scopus 로고    scopus 로고
    • General and highly alpha-regioselective zinc- mediated prenylation of aldehydes and ketones
    • Zhao LM, Jin HS, Wan LJ, et al. General and highly alpha-regioselective zinc- mediated prenylation of aldehydes and ketones. J Org Chem 2011;76:1831-7
    • (2011) J Org Chem , vol.76 , pp. 1831-1837
    • Zhao, L.M.1    Jin, H.S.2    Wan, L.J.3
  • 27
    • 84865476508 scopus 로고    scopus 로고
    • Total synthesis of racemic shikonin
    • Li SS, Xu DF. Total synthesis of racemic shikonin. CN100336792; 2007
    • (2007) CN100336792
    • Li, S.S.1    Xu, D.F.2
  • 29
    • 0031954665 scopus 로고    scopus 로고
    • Concise and efficient total syntheses of alkannin and shikonin
    • DOI 10.1002/(SICI)1521-3773 (19980403)37:6< 839::AID-ANIE839>3.0. CO;2-J
    • Nicolaou KC, Hepworth D. Concise and efficient total syntheses of alkannin and shikonin. Angew Chem Int Edit 1998;37:839-41. The shortest synthesis of shikonin. (Pubitemid 28214100)
    • (1998) Angewandte Chemie - International Edition , vol.37 , Issue.6 , pp. 839-841
    • Nicolaou, K.C.1    Hepworth, D.2
  • 30
    • 77952780077 scopus 로고    scopus 로고
    • An efficient improvement on total synthesis of shikonin
    • Rao Z, Zhou W, Peng Y, et al. An efficient improvement on total synthesis of shikonin. J Chem Res 2010;11:237-8
    • (2010) J Chem Res , vol.11 , pp. 237-238
    • Rao, Z.1    Zhou, W.2    Peng, Y.3
  • 31
    • 0037090424 scopus 로고    scopus 로고
    • A new efficient route for multigram asymmetric synthesis of alkannin and shikonin
    • DOI 10.1002/1521-3765 (20020415)8:8< 1795::AID-CHEM1795>3.0.CO;2-V
    • Couladouros EA, Strongilos AT, Papageorgiou VP, et al. A new efficient route for multigram asymmetric synthesis of alkannin and shikonin. Chem Eur J 2002;8:1795-803 (Pubitemid 34438312)
    • (2002) Chemistry - A European Journal , vol.8 , Issue.8 , pp. 1795-1803
    • Couladouros, E.A.1    Strongilos, A.T.2    Papageorgiou, V.P.3    Plyta, Z.F.4
  • 32
    • 84862669960 scopus 로고    scopus 로고
    • A novel and efficient total synthesis of shikonin
    • Wang R, Guo H, Cui JH, et al. A novel and efficient total synthesis of shikonin. Tetrahedron Lett 2012;53:3977-80
    • (2012) Tetrahedron Lett , vol.53 , pp. 3977-3980
    • Wang, R.1    Guo, H.2    Cui, J.H.3
  • 33
    • 84865476511 scopus 로고    scopus 로고
    • Method for preparation of high-optical purity shikonin via asymmetric synthesis
    • Li SS, Wang RB. Method for preparation of high-optical purity shikonin via asymmetric synthesis. CN102199080; 2011
    • (2011) CN102199080
    • Li, S.S.1    Wang, R.B.2
  • 34
    • 84872881591 scopus 로고    scopus 로고
    • Ruthenocene diphosphine ligand with C2 symmetry and sole planar chirality
    • Zhang WB, Xie F, Liu DL, et al. Ruthenocene diphosphine ligand with C2 symmetry and sole planar chirality. WO2007140717; 2007
    • (2007) WO2007140717
    • Zhang, W.B.1    Xie, F.2    Liu, D.L.3
  • 35
    • 84865513905 scopus 로고    scopus 로고
    • Method for preparation of high optical purity shikonin alkannin and their derivatives
    • Li SS, Wang RB. Method for preparation of high optical purity shikonin, alkannin and their derivatives. CN102399139; 2012
    • (2012) CN102399139
    • Li, S.S.1    Wang, R.B.2
  • 36
    • 84856678408 scopus 로고    scopus 로고
    • Synthesis and human telomeric G-quadruplex DNA - binding activity of glucosaminosides of shikonin/alkannin
    • He H, Bai LP, Jiang ZH. Synthesis and human telomeric G-quadruplex DNA - binding activity of glucosaminosides of shikonin/alkannin. Bioorg Med Chem Lett 2012;22:1582-6
    • (2012) Bioorg Med Chem Lett , vol.22 , pp. 1582-1586
    • He, H.1    Bai, L.P.2    Jiang, Z.H.3
  • 37
  • 38
    • 33645972957 scopus 로고    scopus 로고
    • Analytical methods for the determination of alkannins and shikonins
    • Papageorgiou VP, Assimopoulou AN, Samanidou VF. Analytical methods for the determination of alkannins and shikonins. Curr Org Chem 2006;10:583-622
    • (2006) Curr Org Chem , vol.10 , pp. 583-622
    • Papageorgiou, V.P.1    Assimopoulou, A.N.2    Samanidou, V.F.3
  • 39
    • 78650814206 scopus 로고    scopus 로고
    • Tigloylshikonin, a new minor shikonin derivative, from the roots and the commercial root extract of lithospermum erythrorhizon
    • Ito Y, Onobori K, Yamazaki T, et al. Tigloylshikonin, a new minor shikonin derivative, from the roots and the commercial root extract of lithospermum erythrorhizon. Chem Pharm Bull 2011;59:117-19
    • (2011) Chem Pharm Bull , vol.59 , pp. 117-119
    • Ito, Y.1    Onobori, K.2    Yamazaki, T.3
  • 40
    • 84872880976 scopus 로고    scopus 로고
    • Preparation of saccharide acetate derivatives of shikonin as antitumor agents
    • Wang YG, Su YH, Xie JS, et al. Preparation of saccharide acetate derivatives of shikonin as antitumor agents. CN101671376; 2010
    • (2010) CN101671376
    • Wang, Y.G.1    Su, Y.H.2    Xie, J.S.3
  • 41
    • 84872886345 scopus 로고    scopus 로고
    • Preparation of saccharide derivative of shikonin as antitumor agents
    • Yang YH, Wang XM, Liu SH, et al. Preparation of saccharide derivative of shikonin as antitumor agents. CN101392010; 2011
    • (2011) CN101392010
    • Yang, Y.H.1    Wang, X.M.2    Liu, S.H.3
  • 42
    • 84872882052 scopus 로고    scopus 로고
    • Simple method for synthesis of shikonin carbamate derivative and its medical application
    • Wang YG, Su YH, Xie JS, et al. Simple method for synthesis of shikonin carbamate derivative and its medical application. CN101671278; 2010
    • (2010) CN101671278
    • Wang, Y.G.1    Su, Y.H.2    Xie, J.S.3
  • 43
    • 84872884355 scopus 로고    scopus 로고
    • Method for preparation of beta-hydroxyisovalerylalkannin derivatives and medical application as antitumor agent
    • Li SS, Rao Z, Yi J, et al. Method for preparation of beta- hydroxyisovalerylalkannin derivatives and medical application as antitumor agent. CN101863766; 2010
    • (2010) CN101863766
    • Li, S.S.1    Rao, Z.2    Yi, J.3
  • 44
    • 84872883022 scopus 로고    scopus 로고
    • Method for synthesis of alkannin dimethyl ether derivatives
    • Li SS, Zhou W, Xu DF, et al. Method for synthesis of alkannin dimethyl ether derivatives. CN101139287; 2010
    • (2010) CN101139287
    • Li, S.S.1    Zhou, W.2    Xu, D.F.3
  • 45
    • 84872879929 scopus 로고    scopus 로고
    • Alkannin dimethyl ether with 6-side chain isomer and its derivative and synthetic method
    • Li SS, Zhou W, Xu DF, et al. Alkannin dimethyl ether with 6-side chain isomer, and its derivative and synthetic method. CN101182290; 2010
    • (2010) CN101182290
    • Li, S.S.1    Zhou, W.2    Xu, D.F.3
  • 46
    • 84872877721 scopus 로고    scopus 로고
    • Use of shikonin derivatives extracted from lithospermum erythrorhizon as anticancer agent for treating cancers
    • Zeng JZ, Zhang XK, Liu J, et al. Use of shikonin derivatives extracted from lithospermum erythrorhizon as anticancer agent for treating cancers. CN101683331; 2010
    • (2010) CN101683331
    • Zeng, J.Z.1    Zhang, X.K.2    Liu, J.3
  • 47
    • 84872880961 scopus 로고    scopus 로고
    • Water-soluble alkylated shikonin naphthazarin nucleus derivatives useful in the treatment leukemia and their preparation
    • Li SS, Zhou W, Wang RB, et al. Water-soluble alkylated shikonin naphthazarin nucleus derivatives useful in the treatment leukemia and their preparation. CN101863786; 2010
    • (2010) CN101863786
    • Li, S.S.1    Zhou, W.2    Wang, R.B.3
  • 48
    • 84872882057 scopus 로고    scopus 로고
    • Pharmaceutical composition comprising shikonin derivatives from lithospermum erythrorhizon for treating or preventing diabetes mellitus
    • Park JH, Kim SY, Kang TH, et al. Pharmaceutical composition comprising shikonin derivatives from Lithospermum erythrorhizon for treating or preventing diabetes mellitus. WO200807279; 2009
    • (2009) WO200807279
    • Park, J.H.1    Kim, S.Y.2    Kang, T.H.3
  • 49
    • 0037532632 scopus 로고    scopus 로고
    • Anti-inflammatory activity of shikonin derivatives from Arnebia hispidissima
    • DOI 10.1078/0944-7113-00262
    • Singh B, Sharma MK, Meghwal PR, et al. Anti-inflammatory activity of shikonin derivatives from arnebia hispidissima. Phytomedicine 2003;10:375-80 (Pubitemid 36745159)
    • (2003) Phytomedicine , vol.10 , Issue.5 , pp. 375-380
    • Singh, B.1    Sharma, M.K.2    Meghwal, P.R.3    Sahu, P.M.4    Singh, S.5
  • 50
    • 84865513906 scopus 로고    scopus 로고
    • Application of shikonin and its derivative in medicine
    • Wang F. Application of shikonin and its derivative in medicine. WO2004073699; 2004
    • (2004) WO2004073699
    • Wang, F.1
  • 51
    • 0036613943 scopus 로고    scopus 로고
    • Alkannin and shikonin: Effect on free radical processes and on inflammation - A preliminary pharmacochemical investigation
    • DOI 10.1002/1521-4184 (200208)335:6<262:: AID-ARDP262>3.0.CO;2-Y
    • Kourounakis AP, Assimopoulou AN, Papageorgiou VP, et al. Alkannin and shikonin: Effect on free radical processes and on inflammation-a preliminary pharmacochemical investigation. Arch Pharm 2002;335:262-6 (Pubitemid 34951600)
    • (2002) Archiv der Pharmazie , vol.335 , Issue.6 , pp. 262-266
    • Kourounakis, A.P.1    Assimopoulou, A.N.2    Papageorgiou, V.P.3    Gavalas, A.4    Kourounakis, P.N.5
  • 52
    • 79953795868 scopus 로고    scopus 로고
    • Shikonin extracted from medicinal chinese herbs exerts anti-inflammatory effect via proteasome inhibition
    • That proteasome inhibition by shikonin contributes to its anti-inflammatory effect was demonstrated for the first time
    • Lu L, Qin A, Huang H, et al. Shikonin extracted from medicinal chinese herbs exerts anti-inflammatory effect via proteasome inhibition. Eur J Pharmacol 2011;658:242-7. That proteasome inhibition by shikonin contributes to its anti-inflammatory effect was demonstrated for the first time.
    • (2011) Eur J Pharmacol , vol.658 , pp. 242-247
    • Lu, L.1    Qin, A.2    Huang, H.3
  • 53
    • 77950790743 scopus 로고    scopus 로고
    • Naturally occurring isohexenylnaphthazarins and wound healing: Experimental study in dogs
    • Karayannopoulou M, Loukopoulos P, Papazogiou LG, et al. Naturally occurring isohexenylnaphthazarins and wound healing: Experimental study in dogs. J Cutan Med Surg 2010;14:62-70
    • (2010) J Cutan Med Surg , vol.14 , pp. 62-70
    • Karayannopoulou, M.1    Loukopoulos, P.2    Papazogiou, L.G.3
  • 54
    • 79959693881 scopus 로고    scopus 로고
    • Evaluation of the effectiveness of an ointment based on alkannins/shikonins on second intention wound healing in the dog
    • Karayannopoulou M, Tsioli V, Loukopoulos P, et al. Evaluation of the effectiveness of an ointment based on alkannins/shikonins on second intention wound healing in the dog. Can J Vet Res 2011;75:42-8
    • (2011) Can J Vet Res , vol.75 , pp. 42-48
    • Karayannopoulou, M.1    Tsioli, V.2    Loukopoulos, P.3
  • 55
    • 1642545128 scopus 로고    scopus 로고
    • P53-Mediated Cell Cycle Arrest and Apoptosis Induced by Shikonin via a Caspase-9-Dependent Mechanism in Human Malignant Melanoma A375-S2 Cells
    • DOI 10.1254/jphs.94.166
    • Wu Z, Wu LJ, Li L, et al. P53-mediated cell cycle arrest and apoptosis induced by shikonin via a caspase-9-dependent mechanism in human malignant melanoma A375-S2 cells. J Pharmacol Sci 2004;94:166-76 (Pubitemid 38405131)
    • (2004) Journal of Pharmacological Sciences , vol.94 , Issue.2 , pp. 166-176
    • Wu, Z.1    Wu, L.2    Li, L.3    Tashiro, S.-I.4    Onodera, S.5    Ikejima, T.6
  • 56
    • 55349095348 scopus 로고    scopus 로고
    • Modulation of orphan nuclear receptor Nur77-mediated apoptotic pathway by acetylshikonin and analogues
    • Liu J, ZhouW, Li SS, et al. Modulation of orphan nuclear receptor Nur77-mediated apoptotic pathway by acetylshikonin and analogues. Cancer res 2008;68:8871-80
    • (2008) Cancer res , vol.68 , pp. 8871-8880
    • Liu, J.1    Zhou, W.2    Li, S.S.3
  • 57
    • 0035976040 scopus 로고    scopus 로고
    • Antitumor activities of a newly synthesized shikonin derivative, 2-hyim-DMNQ-S-33
    • DOI 10.1016/S0304-3835(01)00665-6, PII S0304383501006656
    • Kim SH, Kang IC, Yoon TJ, et al. Antitumor activities of a newly synthesized shikonin derivative, 2-hyim- DMNQ-S-33. Cancer lett 2001;172:171-5 (Pubitemid 32889713)
    • (2001) Cancer Letters , vol.172 , Issue.2 , pp. 171-175
    • Kim, S.H.1    Kang, I.-C.2    Yoon, T.J.3    Park, Y.M.4    Kang, K.-S.5    Song, G.Y.6    Ahn, B.Z.7
  • 58
    • 0642335056 scopus 로고    scopus 로고
    • Shikonin modulates cell proliferation by inhibiting epidermal growth factor receptor signaling in human epidermoid carcinoma cells
    • DOI 10.1016/S0304-3835(03)00239-8, PII S0304383503002398
    • Singh F, Gao D, Lebwohl MG, et al. Shikonin modulates cell proliferation by inhibiting epidermal growth factor receptor signaling in human epidermoid carcinoma cells. Cancer lett 2003;200:115-21 (Pubitemid 38366091)
    • (2003) Cancer Letters , vol.200 , Issue.2 , pp. 115-121
    • Singh, F.1    Gao, D.2    Lebwohl, M.G.3    Wei, H.4
  • 59
    • 77952397814 scopus 로고    scopus 로고
    • Shikonin induces apoptosis through reactive oxygen species/extracellular signal-regulated kinase pathway in osteosarcoma cells
    • Chang IC, Huang YJ, Chiang TI, et al. Shikonin induces apoptosis through reactive oxygen species/extracellular signal-regulated kinase pathway in osteosarcoma cells. Biol Pharm Bull 2010;33:816-24
    • (2010) Biol Pharm Bull , vol.33 , pp. 816-824
    • Chang, I.C.1    Huang, Y.J.2    Chiang, T.I.3
  • 60
    • 58549085575 scopus 로고    scopus 로고
    • Synthesis and biological activity of novel shikonin analogues
    • The significant biological activities of shikonin and its analogues relating to HIF-1 pathway was reported firstly
    • Wang WJ, Dai M, Zhu CH, et al. Synthesis and biological activity of novel shikonin analogues. Bioorg Med Chem Lett 2009;19:735-7. The significant biological activities of shikonin and its analogues relating to HIF-1 pathway was reported firstly.
    • (2009) Bioorg Med Chem Lett , vol.19 , pp. 735-737
    • Wang, W.J.1    Dai, M.2    Zhu, C.H.3
  • 61
    • 34247392337 scopus 로고    scopus 로고
    • 6-(1-Oxobutyl)-5,8-dimethoxy-1,4-naphthoquinone inhibits Lewis lung cancer by antiangiogenesis and apoptosis
    • DOI 10.1002/ijc.22486
    • Lee H J, Lee H-J, Song Y, et al. 6 - (1 - Oxobutyl) - 5, 8 - dimethoxy - 1, 4 - naphthoquinone inhibits lewis lung cancer by antiangiogenesis and apoptosis. Int J cancer 2007;120:2481-90 (Pubitemid 46642138)
    • (2007) International Journal of Cancer , vol.120 , Issue.11 , pp. 2481-2490
    • Hyo, J.L.1    Lee, H.-J.2    Song, G.-Y.3    Li, G.4    Lee, J.-H.5    Lu, J.6    Kim, S.-H.7
  • 62
    • 77954966630 scopus 로고    scopus 로고
    • Growth inhibitory effect of beta-hydroxyisovalerylshikoninon prostate cancer cells and related mechanism
    • Liu X, Niu X, Zhou W, et al. Growth inhibitory effect of beta-hydroxyisovalerylshikoninon prostate cancer cells and related mechanism. J Shanghai Jiaotong Univ (Medical Science) 2010;30:527-30
    • (2010) J Shanghai Jiaotong Univ (Medical Science , vol.30 , pp. 527-530
    • Liu, X.1    Niu, X.2    Zhou, W.3
  • 64
    • 49149088537 scopus 로고    scopus 로고
    • Cell research: Induction of apoptosis by shikonin through a ROS/JNK-mediated process in Bcr/Abl-positive chronic myelogenous leukemia (CML) cells
    • Mao X, Yu CR, Li WH, et al. Cell research: Induction of apoptosis by shikonin through a ROS/JNK-mediated process in Bcr/Abl-positive chronic myelogenous leukemia (CML) cells. Cell Res 2008;18:879-88
    • (2008) Cell Res , vol.18 , pp. 879-888
    • Mao, X.1    Yu, C.R.2    Li, W.H.3
  • 65
    • 4744374011 scopus 로고    scopus 로고
    • Induction of apoptosis by shikonin through coordinative modulation of the Bcl-2 family, p27, and p53, release of cytochrome c, and sequential activation of caspases in human colorectal carcinoma cells
    • Hsu PC, Huang YT, Tsai ML, et al. Induction of apoptosis by shikonin through coordinative modulation of the Bcl-2 family, p27, and p53, release of cytochrome c, and sequential activation of caspases in human colorectal carcinoma cells. J Agric Food Chem 2004;52:6330-7
    • (2004) J Agric Food Chem , vol.52 , pp. 6330-6337
    • Hsu, P.C.1    Huang, Y.T.2    Tsai, M.L.3
  • 66
    • 79251482173 scopus 로고    scopus 로고
    • DNA damage induced by shikonin in the presence of Cu (II) ions: Potential mechanism of its activity to apoptotic cell death
    • Cheng HM, Qiu YK, Wu Z, et al. DNA damage induced by shikonin in the presence of Cu (II) ions: Potential mechanism of its activity to apoptotic cell death. J Asian Nat Prod Res 2011;13:12-19
    • (2011) J Asian Nat Prod Res , vol.13 , pp. 12-19
    • Cheng, H.M.1    Qiu, Y.K.2    Wu, Z.3
  • 67
    • 84863682134 scopus 로고    scopus 로고
    • Role of NF-kappaB pathway in shikonin induced apoptosis in oral squamous cell carcinoma Tca-8113 cells
    • Ruan M, Yan M, Yang WJ, et al. Role of NF-kappaB pathway in shikonin induced apoptosis in oral squamous cell carcinoma Tca-8113 cells. Shanghai kou qiang yi xue 2010;19:66-71
    • (2010) Shanghai kou qiang yi xue , vol.19 , pp. 66-71
    • Ruan, M.1    Yan, M.2    Yang, W.J.3
  • 68
    • 84872884248 scopus 로고    scopus 로고
    • Shikonin derivatives as tyrosine kinase inhibitors and antitumor agents
    • Nakaya K, Kajimoto Y, Hsu M, et al. Shikonin derivatives as tyrosine kinase inhibitors and antitumor agents. JP2002212065; 2002
    • (2002) JP2002212065
    • Nakaya, K.1    Kajimoto, Y.2    Hsu, M.3
  • 69
    • 40949115796 scopus 로고    scopus 로고
    • Beta-Hydroxyisovalerylshikonin has a profound anti-growth activity in human endometrial and ovarian cancer cells
    • Takai N, Ueda T, Nishida M, et al. beta-Hydroxyisovalerylshikonin has a profound anti-growth activity in human endometrial and ovarian cancer cells. Gynecol Oncol 2008;109:107-14
    • (2008) Gynecol Oncol , vol.109 , pp. 107-114
    • Takai, N.1    Ueda, T.2    Nishida, M.3
  • 70
    • 0037455717 scopus 로고    scopus 로고
    • β-Hydroxyisovalerylshikonin induces apoptosis in human leukemia cells by inhibiting the activity of a polo-like kinase 1 (PLK1)
    • DOI 10.1038/sj.onc.1206200
    • Masuda Y, Nishida A, Hori K, et al. beta-Hydroxyisovalerylshikonin induces apoptosis in human leukemia cells by inhibiting the activity of a polo-like kinase 1 (PLK1). Oncogene 2003;22:1012-23 (Pubitemid 36313145)
    • (2003) Oncogene , vol.22 , Issue.7 , pp. 1012-1023
    • Masuda, Y.1    Nishida, A.2    Hori, K.3    Hirabayashi, T.4    Kajimoto, S.5    Nakajo, S.6    Kondo, T.7    Asaka, M.8    Nakaya, K.9
  • 71
    • 64249097600 scopus 로고    scopus 로고
    • Shikonin exerts antitumor activity via proteasome inhibition and cell death induction in vitro and in vivo
    • Yang HJ, Zhou P, Huang HB, et al. Shikonin exerts antitumor activity via proteasome inhibition and cell death induction in vitro and in vivo. Int J Cancer 2009;124:2450-9
    • (2009) Int J Cancer , vol.124 , pp. 2450-2459
    • Yang, H.J.1    Zhou, P.2    Huang, H.B.3
  • 72
    • 34250748014 scopus 로고    scopus 로고
    • Shikonin circumvents cancer drug resistance by induction of a necroptotic death
    • DOI 10.1158/1535-7163.MCT-06-0511
    • Han W, Li L, Qiu S, et al. Shikonin circumvents cancer drug resistance by induction of a necroptotic death. Mol Cancer Ther 2007;6:1641-9 (Pubitemid 46954031)
    • (2007) Molecular Cancer Therapeutics , vol.6 , Issue.5 , pp. 1641-1649
    • Han, W.1    Li, L.2    Qiu, S.3    Lu, Q.4    Pan, Q.5    Gu, Y.6    Luo, J.7    Hu, X.8
  • 73
    • 58149316180 scopus 로고    scopus 로고
    • Naturally-occurring shikonin analogues-A class of necroptotic inducers that circumvent cancer drug resistance
    • Xuan YY, Hu X. Naturally-occurring shikonin analogues-a class of necroptotic inducers that circumvent cancer drug resistance. Cancer Lett 2009;274:233-42
    • (2009) Cancer Lett , vol.274 , pp. 233-242
    • Xuan, Y.Y.1    Hu, X.2
  • 74
    • 80054883247 scopus 로고    scopus 로고
    • Shikonin and its analogs inhibit cancer cell glycolysis by targeting tumor pyruvate kinase-M2
    • Shikonin and alkannin are the most potent and specific inhibitors to PKM2 reported so far
    • Chen J, Xie J, Jiang Z, et al. Shikonin and its analogs inhibit cancer cell glycolysis by targeting tumor pyruvate kinase-M2. Oncogene 2011;30:4297-306. Shikonin and alkannin are the most potent and specific inhibitors to PKM2 reported so far.
    • (2011) Oncogene , vol.30 , pp. 4297-4306
    • Chen, J.1    Xie, J.2    Jiang, Z.3
  • 75
    • 56049098575 scopus 로고    scopus 로고
    • Shikonin, acetylshikonin, and isobutyroylshikonin inhibit VEGF-induced angiogenesis and suppress tumor growth in lewis lung carcinoma-bearing mice
    • Lee HJ, Magesh V, Nam D, et al. Shikonin, acetylshikonin, and isobutyroylshikonin inhibit VEGF-induced angiogenesis and suppress tumor growth in lewis lung carcinoma-bearing mice. Yakugaku Zasshi 2008;128:1681-8
    • (2008) Yakugaku Zasshi , vol.128 , pp. 1681-1688
    • Lee, H.J.1    Magesh, V.2    Nam, D.3
  • 76
    • 79953756477 scopus 로고    scopus 로고
    • Shikonin inhibits tumor invasion via down-regulation of NF-kappaB-mediated MMP-9 expression in human ACC-M cells
    • Min R, Zun Z, Min Y, et al. Shikonin inhibits tumor invasion via down-regulation of NF-kappaB-mediated MMP-9 expression in human ACC-M cells. Oral Dis 2011;17:362-9
    • (2011) Oral Dis , vol.17 , pp. 362-369
    • Min, R.1    Zun, Z.2    Min, Y.3
  • 78
    • 63149129655 scopus 로고    scopus 로고
    • Bcl-2 inhibitors: Targeting mitochondrial apoptotic pathways in cancer therapy
    • Kang MH, Reynolds CP. Bcl-2 inhibitors: Targeting mitochondrial apoptotic pathways in cancer therapy. Clin cancer res 2009;15:1126-32
    • (2009) Clin cancer res , vol.15 , pp. 1126-1132
    • Kang, M.H.1    Reynolds, C.P.2
  • 79
    • 0032575752 scopus 로고    scopus 로고
    • Mitochondria and apoptosis
    • Green DR, Reed JC. Mitochondria and apoptosis. Science 1998;281:1309-12 (Pubitemid 28406816)
    • (1998) Science , vol.281 , Issue.5381 , pp. 1309-1312
    • Green, D.R.1    Reed, J.C.2
  • 80
    • 0032796797 scopus 로고    scopus 로고
    • Shikonin, an ingredient of lithospermum erythrorhizon induced apoptosis in hl60 human premyelocytic leukemia cell line
    • Yoo Y, Kim YO, Lim NY, et al. Shikonin, an ingredient of lithospermum erythrorhizon induced apoptosis in hl60 human premyelocytic leukemia cell line. Planta Med 1999;65:532-5
    • (1999) Planta Med , vol.65 , pp. 532-535
    • Yoo, Y.1    Kim, Y.O.2    Lim, N.Y.3
  • 81
    • 4744374011 scopus 로고    scopus 로고
    • Induction of apoptosis by shikonin through coordinative modulation of the bcl-2 family, p27, and p53, release of cytochrome c, and sequential activation of caspases in human colorectal carcinoma cells
    • Hsu PC, Huang TY, Tsai ML, et al. Induction of apoptosis by shikonin through coordinative modulation of the bcl-2 family, p27, and p53, release of cytochrome c, and sequential activation of caspases in human colorectal carcinoma cells. J Agric Food Chem 2004;52:6330-7
    • (2004) J Agric Food Chem , vol.52 , pp. 6330-6337
    • Hsu, P.C.1    Huang, T.Y.2    Tsai, M.L.3
  • 82
    • 0036637164 scopus 로고    scopus 로고
    • Direct reaction between shikonin and thiols induces apoptosis in HL60 cells
    • DOI 10.1248/bpb.25.827
    • Gao D, Hiromura M, Yasui H, et al. Direct reaction between shikonin and thiols induces apoptosis in hl60 cells. Biol Pharm Bull 2002;25:827-32 (Pubitemid 40022107)
    • (2002) Biological and Pharmaceutical Bulletin , vol.25 , Issue.7 , pp. 827-832
    • Gao, D.1    Hiromura, M.2    Yasui, H.3    Sakurai, H.4
  • 83
    • 33846150667 scopus 로고    scopus 로고
    • Effect of Shikonin on human breast cancer cells proliferation and apoptosis In vitro
    • DOI 10.1248/yakushi.126.1383
    • Hou Y, Guo T, Wu C, et al. Effect of shikonin on human breast cancer cells proliferation and apoptosis in vitro. Yakugaku Zasshi 2006;126:1383-6 (Pubitemid 46089900)
    • (2006) Yakugaku Zasshi , vol.126 , Issue.12 , pp. 1383-1386
    • Hou, Y.1    Guo, T.2    Wu, C.3    He, X.4    Zhao, M.5
  • 84
    • 37349073187 scopus 로고    scopus 로고
    • Shikonin-induced apoptosis involves caspase-3 activity in a human bladder cancer cell line
    • Yen CC, Kuo HM, Li TM, et al. Shikonin-induced apoptosis involves caspase-3 activity in a human bladder cancer cell line. In Vivo 2007;21:1011-20
    • (2007) Vivo , vol.21 , pp. 1011-1020
    • Yen, C.C.1    Kuo, H.M.2    Li, T.M.3
  • 86
    • 0030931876 scopus 로고    scopus 로고
    • Caspases: The executioners of apoptosis
    • Cohen GM. Caspases: The executioners of apoptosis. Biochem J 1997;326:1-16 (Pubitemid 27386911)
    • (1997) Biochemical Journal , vol.326 , Issue.1 , pp. 1-16
    • Cohen, G.M.1
  • 87
    • 0032575688 scopus 로고    scopus 로고
    • The Bcl-2 protein family: Arbiters of cell survival
    • Adam JM, Cory S. The bcl-2 protein family: Arbiters of cell survival. Science 1998;281:1322-6 (Pubitemid 28406819)
    • (1998) Science , vol.281 , Issue.5381 , pp. 1322-1326
    • Adams, J.M.1    Cory, S.2
  • 89
    • 0028206341 scopus 로고
    • BH1 and BH2 domains of Bcl-2 are required for inhibition of apoptosis and heterodimerization with Bax
    • DOI 10.1038/369321a0
    • Yinxm XM, Oltwvi ZN, Korsmeyer SJ. BH1 and BH2 domains of Bcl-2 are required for inhibition of apoptosis and heterodimerization with Bax. Nature 1994;369:321-3 (Pubitemid 24159542)
    • (1994) Nature , vol.369 , Issue.6478 , pp. 321-323
    • Yin, X.-M.1    Oltvai, Z.N.2    Korsmeyer, S.J.3
  • 91
    • 43549097825 scopus 로고    scopus 로고
    • During negative selection, Nur77 family proteins translocate to mitochondria where they associate with Bcl-2 and expose its proapoptotic BH3 domain
    • DOI 10.1084/jem.20080101
    • Thompson J, Winoto A. During negative selection, Nur77 family proteins translocate to motochondria where they associate with Bcl-2 and expose its proapoptotic BH3 domain. J Exp Med 2008;205:1029-36 (Pubitemid 351679679)
    • (2008) Journal of Experimental Medicine , vol.205 , Issue.5 , pp. 1029-1036
    • Thompson, J.1    Winoto, A.2
  • 92
    • 0037032817 scopus 로고    scopus 로고
    • Mitogen-activated protein kinase pathways mediated by ERK, JNK, and p38 protein kinases
    • DOI 10.1126/science.1072682
    • Johnson GL, Lapadat R.Mitogen-activated protein kinase pathways mediated by erk, jnk, and p38 protein kinases. Science 2002;298:1911-12 (Pubitemid 35425238)
    • (2002) Science , vol.298 , Issue.5600 , pp. 1911-1912
    • Johnson, G.L.1    Lapadat, R.2
  • 93
    • 0029011218 scopus 로고
    • The MAPK signaling cascade
    • Seger R, Krebs EG. The MAPK signaling cascade. Faseb J 1995;9:726-35
    • (1995) Faseb J , vol.9 , pp. 726-735
    • Seger, R.1    Krebs, E.G.2
  • 95
    • 80052939147 scopus 로고    scopus 로고
    • Synthesis and antitumor activity of beta-hydroxyisovalerylshikonin analogues
    • Rao Z, Liu X, Zhou W, et al. Synthesis and antitumor activity of beta-hydroxyisovalerylshikonin analogues. Eur J Med Chem 2011;46:3934-41
    • (2011) Eur J Med Chem , vol.46 , pp. 3934-3941
    • Rao, Z.1    Liu, X.2    Zhou, W.3
  • 96
    • 0029900295 scopus 로고    scopus 로고
    • The tumor necrosis factor ligand and receptor families
    • DOI 10.1056/NEJM199606273342607
    • Bazzoni F, Beutler B. The tumor necrosis factor ligand and receptor families. N Engl J Med 1996;334:1717-25 (Pubitemid 26193625)
    • (1996) New England Journal of Medicine , vol.334 , Issue.26 , pp. 1717-1725
    • Bazzoni, F.1    Beutler, B.2
  • 97
    • 0025343230 scopus 로고
    • Signal transduction by receptors with tyrosine kinase activity
    • Ullrich A, Schlessinger J. Signal transduction by receptors with tyrosine kinase activity. Cell 1990;61:203-12
    • (1990) Cell , vol.61 , pp. 203-212
    • Ullrich, A.1    Schlessinger, J.2
  • 98
    • 0026674221 scopus 로고
    • Characterization of protein tyrosine kinases from human breast cancer: Involvement of the c-src oncogene product
    • Ottenhoff-kalff AE, Rijksen G, Van Beurden EACM, et al. Characterization of protein tyrosine kinases from human breast cancer: Involvement of the c-src oncogene product. Cancer Res 1992;52:4773-8
    • (1992) Cancer Res , vol.52 , pp. 4773-4778
    • Ottenhoff-kalff, A.E.1    Rijksen, G.2    Van Beurden, E.A.C.M.3
  • 99
    • 66249108601 scopus 로고    scopus 로고
    • Understanding the warburg effect: The metabolic requirements of cell proliferation
    • Vander Heiden MG, Cantley LC, Thompson CB. Understanding the warburg effect: The metabolic requirements of cell proliferation. Science 2009;324:1029-33
    • (2009) Science , vol.324 , pp. 1029-1033
    • Vander Heiden, M.G.1    Cantley, L.C.2    Thompson, C.B.3
  • 100
    • 33344472286 scopus 로고    scopus 로고
    • Antiangiogenesis in cancer therapy - Endostatin and its mechanisms of action
    • DOI 10.1016/j.yexcr.2005.11.015, PII S0014482705005458
    • Folkman J. Antiangiogenesis in cancer therapy-endostatin and its mechanisms of action. Exp Cell Res 2006;312:594-607 (Pubitemid 43290336)
    • (2006) Experimental Cell Research , vol.312 , Issue.5 , pp. 594-607
    • Folkman, J.1
  • 102
    • 0036512208 scopus 로고    scopus 로고
    • New functions for the matrix metalloproteinases in cancer progression
    • Egeblad M, Werb Z. New functions for the matrix metalloproteinases in cancer progression. Nat Rev Cancer 2002;2:161-74 (Pubitemid 37328786)
    • (2002) Nature Reviews Cancer , vol.2 , Issue.3 , pp. 161-174
    • Egeblad, M.1    Werb, Z.2


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.