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Volumn 7, Issue 12, 2012, Pages 1677-1688

Cytotoxic agents of the crinane series of amaryllidaceae alkaloids

Author keywords

Alkaloids; Amaryllidaceae; Anticancer; Crinane; Cytotoxic

Indexed keywords

11 HYDROXYVITATTINE; 11 HYDROXYVITATTINE N OXIDE; 11 O ACETYLCRINAMINE; 11 O METHYLCRINAMINE; 4 METHOXY BENZOYL; 6 HYDROXYCRINAMINE; 8 O DEMETHYLMARITIDINE; ALKALOID; CRINAMINE; CRININE; CYTOTOXIC AGENT; DIHYDROCRINAMINE; GALANTAMINE; HAEMANTHAMINE; HAEMANTHIDINE; HAMAYNE; HOMOLYCORINE; ISMINE; LYCORINE; MONTANINE; NARCICLASINE; NARCIPRIMINE; NORBELLADINE; PANCRATISTATIN; PAPYRAMINE; PLANT MEDICINAL PRODUCT; TAZETTINE; TRIS PHAERIDINE; UNCLASSIFIED DRUG; UNINDEXED DRUG; VITATTINE; AMARYLLIDACEAE ALKALOID; ANTINEOPLASTIC AGENT; CRINANE;

EID: 84875037431     PISSN: 1934578X     EISSN: 15559475     Source Type: Journal    
DOI: 10.1177/1934578x1200701234     Document Type: Review
Times cited : (57)

References (81)
  • 1
    • 33749416245 scopus 로고    scopus 로고
    • Chemical and biological aspects of Narcissus alkaloids
    • Cordell GA (Ed). Elsevier, Amsterdam, Netherlands
    • (a) Bastida J, Lavilla R, Viladomat F. (2006) Chemical and biological aspects of Narcissus alkaloids. In The Alkaloids. Cordell GA (Ed). Elsevier, Amsterdam, Netherlands, 87-179;
    • (2006) The Alkaloids , pp. 87-179
    • Bastida, J.1    Lavilla, R.2    Viladomat, F.3
  • 3
    • 80052059081 scopus 로고    scopus 로고
    • Amaryllidaceae and Sceletium alkaloids
    • (c) Jin Z. (2011) Amaryllidaceae and Sceletium alkaloids. Natural Product Reports, 28, 1126-1142;
    • (2011) Natural Product Reports , vol.28 , pp. 1126-1142
    • Jin, Z.1
  • 5
    • 0028819939 scopus 로고
    • The pharmacology of galanthamine and its analogues
    • (a) Harvey AL. (1995) The pharmacology of galanthamine and its analogues. Pharmacology & Therapeutics, 68, 113-128;
    • (1995) Pharmacology & Therapeutics , vol.68 , pp. 113-128
    • Harvey, A.L.1
  • 6
    • 33645450644 scopus 로고    scopus 로고
    • Acetylcholinesterase inhibitors from plants and fungi
    • (b) Houghton PJ, Ren Y, Howes M-J. (2006) Acetylcholinesterase inhibitors from plants and fungi. Natural Product Reports, 23, 181-199;
    • (2006) Natural Product Reports , vol.23 , pp. 181-199
    • Houghton, P.J.1    Ren, Y.2    Howes, M.-J.3
  • 8
    • 0037063693 scopus 로고    scopus 로고
    • Acetylcholinesterase inhibitory activity of some Amaryllidaceae alkaloids and Narcissus extracts
    • (d) Lopez S, Bastida J, Viladomat F, Codina C. (2002) Acetylcholinesterase inhibitory activity of some Amaryllidaceae alkaloids and Narcissus extracts. Life Sciences, 71, 2521-2529;
    • (2002) Life Sciences , vol.71 , pp. 2521-2529
    • Lopez, S.1    Bastida, J.2    Viladomat, F.3    Codina, C.4
  • 9
    • 1842431888 scopus 로고    scopus 로고
    • Acetylcholinesterase enzyme inhibitory effects of Amaryllidaceae alkaloids
    • (e) Elgorashi EE, Stafford GI, Van Staden J. (2004) Acetylcholinesterase enzyme inhibitory effects of Amaryllidaceae alkaloids. Planta Medica, 70, 260-262;
    • (2004) Planta Medica , vol.70 , pp. 260-262
    • Elgorashi, E.E.1    Stafford, G.I.2    Van Staden, J.3
  • 10
    • 77955658321 scopus 로고    scopus 로고
    • Structure-activity relationship studies on acetylcholinesterase inhibition in the lycorine series of Amaryllidaceae alkaloids
    • (f) McNulty J, Nair JJ, Little JRL, Brennan JD, Bastida J. (2010) Structure-activity relationship studies on acetylcholinesterase inhibition in the lycorine series of Amaryllidaceae alkaloids. Bioorganic and Medicinal Chemistry Letters, 20, 5290-5294;
    • (2010) Bioorganic and Medicinal Chemistry Letters , vol.20 , pp. 5290-5294
    • McNulty, J.1    Nair, J.J.2    Little, J.R.L.3    Brennan, J.D.4    Bastida, J.5
  • 11
    • 84864703020 scopus 로고    scopus 로고
    • Acetylcholinesterase inhibition within the lycorine series of Amaryllidaceae alkaloids
    • (g) Nair JJ, Van Staden J. (2012) Acetylcholinesterase inhibition within the lycorine series of Amaryllidaceae alkaloids. Natural Product Communications, 7, 959-962.
    • (2012) Natural Product Communications , vol.7 , pp. 959-962
    • Nair, J.J.1    Van Staden, J.2
  • 13
    • 10044221979 scopus 로고    scopus 로고
    • Effects of lycorine on HL-60 cells via arresting cell cycle and inducing apoptosis
    • (b) Liu J, Hu W, He L, Ye M, Li Y. (2004) Effects of lycorine on HL-60 cells via arresting cell cycle and inducing apoptosis. FEBS letters, 578, 245-250;
    • (2004) FEBS Letters , vol.578 , pp. 245-250
    • Liu, J.1    Hu, W.2    He, L.3    Ye, M.4    Li, Y.5
  • 16
    • 67651155818 scopus 로고    scopus 로고
    • Anticancer evaluation of structurally diverse Amaryllidaceae alkaloids and their synthetic derivatives
    • (e) Evidente A, Kornienko A. (2009) Anticancer evaluation of structurally diverse Amaryllidaceae alkaloids and their synthetic derivatives. Phytochemistry Reviews, 8, 449-459;
    • (2009) Phytochemistry Reviews , vol.8 , pp. 449-459
    • Evidente, A.1    Kornienko, A.2
  • 17
    • 67651157036 scopus 로고    scopus 로고
    • Biological evaluation of structurally diverse Amaryllidaceae alkaloids and their synthetic derivatives: Discovery of novel leads for anticancer drug design
    • (f) Evidente A, Kireev AS, Jenkins AR, Romero AE, Steelant WFA, Van Slambrouck S, Kornienko A. (2009) Biological evaluation of structurally diverse Amaryllidaceae alkaloids and their synthetic derivatives: discovery of novel leads for anticancer drug design. Planta Medica, 75, 501-507;
    • (2009) Planta Medica , vol.75 , pp. 501-507
    • Evidente, A.1    Kireev, A.S.2    Jenkins, A.R.3    Romero, A.E.4    Steelant, W.F.A.5    Van Slambrouck, S.6    Kornienko, A.7
  • 18
    • 67249134952 scopus 로고    scopus 로고
    • Structure-activity studies on the lycorine pharmacophore: A potent inducer of apoptosis in human leukemia cells
    • (g) McNulty J, Nair JJ, Bastida J, Pandey S, Griffin C. (2009) Structure-activity studies on the lycorine pharmacophore: a potent inducer of apoptosis in human leukemia cells. Phytochemistry, 70, 913-919;
    • (2009) Phytochemistry , vol.70 , pp. 913-919
    • McNulty, J.1    Nair, J.J.2    Bastida, J.3    Pandey, S.4    Griffin, C.5
  • 24
    • 47249124531 scopus 로고    scopus 로고
    • Chemistry, biology and medicinal potential of narciclasine and its congeners
    • (d) Kornienko A, Evidente A. (2008) Chemistry, biology and medicinal potential of narciclasine and its congeners. Chemical Reviews, 108, 1982-2014;
    • (2008) Chemical Reviews , vol.108 , pp. 1982-2014
    • Kornienko, A.1    Evidente, A.2
  • 25
    • 70350085648 scopus 로고    scopus 로고
    • Amaryllidaceae isocarbostyril alkaloids and their derivatives as promising antitumor agents
    • (e) Ingrassia L, Lefranc F, Mathieu V, Darro F, Kiss R. (2008) Amaryllidaceae isocarbostyril alkaloids and their derivatives as promising antitumor agents. Translational Oncology, 1, 1-13;
    • (2008) Translational Oncology , vol.1 , pp. 1-13
    • Ingrassia, L.1    Lefranc, F.2    Mathieu, V.3    Darro, F.4    Kiss, R.5
  • 28
    • 21244439798 scopus 로고    scopus 로고
    • Pancratistatin causes early activation of caspase-3 and the flipping of phosphatidyl serine followed by rapid apoptosis specifically in human lymphoma cells
    • (a) Kekre N, Griffin C, McNulty J, Pandey S. (2005) Pancratistatin causes early activation of caspase-3 and the flipping of phosphatidyl serine followed by rapid apoptosis specifically in human lymphoma cells. Cancer Chemotherapy & Pharmacology, 56, 29-38;
    • (2005) Cancer Chemotherapy & Pharmacology , vol.56 , pp. 29-38
    • Kekre, N.1    Griffin, C.2    McNulty, J.3    Pandey, S.4
  • 29
    • 21244484687 scopus 로고    scopus 로고
    • Pancratistatin: A natural anticancer compound that targets mitochondria specifically in cancer cells to induce apoptosis
    • (b) McLachlan A, Kekre N, McNulty J, Pandey S. (2005) Pancratistatin: A natural anticancer compound that targets mitochondria specifically in cancer cells to induce apoptosis. Apoptosis, 10, 619-630.
    • (2005) Apoptosis , vol.10 , pp. 619-630
    • McLachlan, A.1    Kekre, N.2    McNulty, J.3    Pandey, S.4
  • 30
    • 0002530666 scopus 로고    scopus 로고
    • Design constraints in practical syntheses of complex molecules: Current status, case studies with carbohydrates and alkaloids, and future perspectives
    • (a) Hudlicky T. (1996) Design constraints in practical syntheses of complex molecules: current status, case studies with carbohydrates and alkaloids, and future perspectives. Chemical Reviews, 96, 3-30;
    • (1996) Chemical Reviews , vol.96 , pp. 3-30
    • Hudlicky, T.1
  • 31
    • 14644422595 scopus 로고    scopus 로고
    • Synthesis of Amaryllidaceae constituents-an update
    • (b) Rinner U, Hudlicky T. (2005) Synthesis of Amaryllidaceae constituents-an update. Synlett, 3, 365-387;
    • (2005) Synlett , vol.3 , pp. 365-387
    • Rinner, U.1    Hudlicky, T.2
  • 35
    • 79951527897 scopus 로고    scopus 로고
    • Human cytochrome P450 liability studies of trans-dihydronarciclasine: A readily available, potent and selective cancer cell growth inhibitor
    • (f) McNulty J, Thorat A, Vurgun N, Nair JJ, Makaji E, Crankshaw DJ, Holloway AC, Pandey S. (2011) Human cytochrome P450 liability studies of trans-dihydronarciclasine: a readily available, potent and selective cancer cell growth inhibitor. Journal of Natural Products, 74, 106-108.
    • (2011) Journal of Natural Products , vol.74 , pp. 106-108
    • McNulty, J.1    Thorat, A.2    Vurgun, N.3    Nair, J.J.4    Makaji, E.5    Crankshaw, D.J.6    Holloway, A.C.7    Pandey, S.8
  • 38
    • 0035917342 scopus 로고    scopus 로고
    • Antineoplastic agents. 450. Synthesis of (+)-pancratistatin from (+)-narciclasine as relay
    • (c) Pettit GR, Melody N, Herald DL. (2001) Antineoplastic agents. 450. Synthesis of (+)-pancratistatin from (+)-narciclasine as relay. Journal of Organic Chemistry, 66, 2583-2587;
    • (2001) Journal of Organic Chemistry , vol.66 , pp. 2583-2587
    • Pettit, G.R.1    Melody, N.2    Herald, D.L.3
  • 39
    • 0037073868 scopus 로고    scopus 로고
    • Total synthesis and biological evaluation of Amaryllidaceae alkaloids: Narciclasine, ent-7-deoxypancratistatin, regioisomer of 7-deoxypancratistatin, 10b-epi-deoxypancratistatin, and truncated derivatives
    • (d) Hudlicky T, Rinner U, Gonzales D, Akgun H, Schilling S, Siengalewicz P, Martinot TA, Pettit GR. (2002) Total synthesis and biological evaluation of Amaryllidaceae alkaloids: narciclasine, ent-7-deoxypancratistatin, regioisomer of 7-deoxypancratistatin, 10b-epi-deoxypancratistatin, and truncated derivatives. Journal of Organic Chemistry, 67, 8726-8743;
    • (2002) Journal of Organic Chemistry , vol.67 , pp. 8726-8743
    • Hudlicky, T.1    Rinner, U.2    Gonzales, D.3    Akgun, H.4    Schilling, S.5    Siengalewicz, P.6    Martinot, T.A.7    Pettit, G.R.8
  • 41
    • 7244260408 scopus 로고    scopus 로고
    • A P-carboline-1-one mimic of the anticancer Amaryllidaceae constituent pancratistatin: Synthesis and biological evaluation
    • (f) Rinner U, Hudlicky T, Gordon H, Pettit GR. (2004) A P-carboline-1-one mimic of the anticancer Amaryllidaceae constituent pancratistatin: synthesis and biological evaluation. Angewandte Chemie International Edition in English, 43, 5342-5346;
    • (2004) Angewandte Chemie International Edition in English , vol.43 , pp. 5342-5346
    • Rinner, U.1    Hudlicky, T.2    Gordon, H.3    Pettit, G.R.4
  • 42
    • 26844546931 scopus 로고    scopus 로고
    • A synthesis of 3-deoxydihydrolycoricidine: Refinement of a structurally minimum pancratistatin pharmacophore
    • (g) McNulty J, Larichev V, Pandey S. (2005) A synthesis of 3-deoxydihydrolycoricidine: refinement of a structurally minimum pancratistatin pharmacophore. Bioorganic & Medicinal Chemistry Letters, 15, 5315-5318;
    • (2005) Bioorganic & Medicinal Chemistry Letters , vol.15 , pp. 5315-5318
    • McNulty, J.1    Larichev, V.2    Pandey, S.3
  • 44
    • 42249111889 scopus 로고    scopus 로고
    • Synthesis and biological evaluation of fully functionalized seco-pancratistatin analogues
    • (i) McNulty J, Nair JJ, Griffin C, Pandey S. (2008) Synthesis and biological evaluation of fully functionalized seco-pancratistatin analogues. Journal of Natural Products, 71, 357-363.
    • (2008) Journal of Natural Products , vol.71 , pp. 357-363
    • McNulty, J.1    Nair, J.J.2    Griffin, C.3    Pandey, S.4
  • 45
    • 0000427207 scopus 로고
    • Crinum alkaloids: Their chemistry and biology
    • (a) Ghosal S, Saini KS, Razdan S. (1985) Crinum alkaloids: their chemistry and biology. Phytochemistry, 24, 2141-2156;
    • (1985) Phytochemistry , vol.24 , pp. 2141-2156
    • Ghosal, S.1    Saini, K.S.2    Razdan, S.3
  • 48
    • 0014199791 scopus 로고
    • Narciclasine: An antimitotic substance from Narcissus bulbs
    • (a) Ceriotti G. (1967) Narciclasine: an antimitotic substance from Narcissus bulbs. Nature, 213, 595-596;
    • (1967) Nature , vol.213 , pp. 595-596
    • Ceriotti, G.1
  • 49
    • 0017258099 scopus 로고
    • Inhibitors of protein synthesis in eukaryotic cells. Comparative effects of some Amaryllidaceae alkaloids
    • (b) Jimenez A, Santos A, Alonso G, Vazquez D. (1976) Inhibitors of protein synthesis in eukaryotic cells. Comparative effects of some Amaryllidaceae alkaloids. Biochimica et Biophysica Acta, 425, 342-348.
    • (1976) Biochimica et Biophysica Acta , vol.425 , pp. 342-348
    • Jimenez, A.1    Santos, A.2    Alonso, G.3    Vazquez, D.4
  • 50
    • 0018907876 scopus 로고
    • Therapeutic activity of pretazettine on Rauscher leukemia: Comparison with the related Amaryllidaceae alkaloids
    • Furusawa E, Irie H, Combs D, Wildman WC. (1980) Therapeutic activity of pretazettine on Rauscher leukemia: comparison with the related Amaryllidaceae alkaloids. Experimental Chemotherapy, 26, 36-45.
    • (1980) Experimental Chemotherapy , vol.26 , pp. 36-45
    • Furusawa, E.1    Irie, H.2    Combs, D.3    Wildman, W.C.4
  • 52
  • 53
    • 0000975424 scopus 로고
    • Chemical constituents of Amaryllidaceae. Part 24. Crinafoline and crinafolidine, two antitumor alkaloids from Crinum latifolium
    • Ghosal S. (1986) Chemical constituents of Amaryllidaceae. Part 24. Crinafoline and crinafolidine, two antitumor alkaloids from Crinum latifolium. Journal of Chemical Research (S), 312-313.
    • (1986) Journal of Chemical Research (S) , pp. 312-313
    • Ghosal, S.1
  • 54
    • 0025991554 scopus 로고
    • Cytotoxic activity of Amaryllidaceae alkaloids from Crinum augustum and Crinum bulbispermum
    • Abd El Hafiz MA, Ramadan MA, Jung ML, Beck JP, Anton R. (1991) Cytotoxic activity of Amaryllidaceae alkaloids from Crinum augustum and Crinum bulbispermum. Planta Medica, 57, 437-439.
    • (1991) Planta Medica , vol.57 , pp. 437-439
    • Abd El Hafiz, M.A.1    Ramadan, M.A.2    Jung, M.L.3    Beck, J.P.4    Anton, R.5
  • 63
    • 0036277049 scopus 로고    scopus 로고
    • Antiproliferative Amaryllidaceae alkaloids isolated from the bulbs of Sprekelia formosissima and Hymenocallis x festalis
    • Hohmann J, Forgo P, Molnár J, Wolfard K, Molnár A, Thalhammer T, Mathé I, Sharples D. (2002) Antiproliferative Amaryllidaceae alkaloids isolated from the bulbs of Sprekelia formosissima and Hymenocallis x festalis. Planta Medica, 68, 454-457.
    • (2002) Planta Medica , vol.68 , pp. 454-457
    • Hohmann, J.1    Forgo, P.2    Molnár, J.3    Wolfard, K.4    Molnár, A.5    Thalhammer, T.6    Mathé, I.7    Sharples, D.8
  • 64
    • 33645997535 scopus 로고    scopus 로고
    • Investigation of antimicrobial and cytotoxic properties of alkaloids from some species of Crinum in Vietnam
    • Phan TS, Tran BD, Bach D, Phan MG, Nguyen TM, Hoang TH, Le MH. (2003) Investigation of antimicrobial and cytotoxic properties of alkaloids from some species of Crinum in Vietnam. Tap Chi Duoc Hoc, 4, 18-21.
    • (2003) Tap Chi Duoc Hoc , vol.4 , pp. 18-21
    • Phan, T.S.1    Tran, B.D.2    Bach, D.3    Phan, M.G.4    Nguyen, T.M.5    Hoang, T.H.6    Le, M.H.7
  • 67
    • 34250849599 scopus 로고    scopus 로고
    • Selective cytotoxicity of pancratistatin-related natural Amaryllidaceae alkaloids: Evaluation of the activity of two new compounds
    • (b) Griffin C, Sharda N, Sood, D, Nair JJ, McNulty J, Pandey S. (2007) Selective cytotoxicity of pancratistatin-related natural Amaryllidaceae alkaloids: evaluation of the activity of two new compounds. Cancer Cell International, 7, 10-16.
    • (2007) Cancer Cell International , vol.7 , pp. 10-16
    • Griffin, C.1    Sharda, N.2    Sood, D.3    Nair, J.J.4    McNulty, J.5    Pandey, S.6
  • 78
    • 84866018618 scopus 로고    scopus 로고
    • Cytotoxicity and acetylcholinesterase inhibitory activity of an isolated crinine alkaloid from Boophone disticha (Amaryllidaceae)
    • Adewusi EA, Fouche G, Steenkamp V. (2012) Cytotoxicity and acetylcholinesterase inhibitory activity of an isolated crinine alkaloid from Boophone disticha (Amaryllidaceae). Journal of Ethnopharmacology, 143, 572-578.
    • (2012) Journal of Ethnopharmacology , vol.143 , pp. 572-578
    • Adewusi, E.A.1    Fouche, G.2    Steenkamp, V.3


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