메뉴 건너뛰기




Volumn 515, Issue , 2012, Pages 189-206

Strategies for engineering plant natural products: The iridoid-derived monoterpene indole alkaloids of catharanthus roseus

Author keywords

Directed biosynthesis; Iridoid; Metabolic engineering; Monoterpene indole alkaloid; Mutasynthesis

Indexed keywords

AVIDIN; CAPTAVIDIN; INDOLE ALKALOID; IRIDOID; NATURAL PRODUCT; NAVELBINE; SECOLOGANIN; TERPENE; TOPOTECAN; UNCLASSIFIED DRUG; VINDOLINE; VINFLUNINE;

EID: 84866489051     PISSN: 00766879     EISSN: 15577988     Source Type: Book Series    
DOI: 10.1016/B978-0-12-394290-6.00009-4     Document Type: Chapter
Times cited : (23)

References (44)
  • 1
    • 0022575813 scopus 로고
    • Three alkaloids as selective destroyers of cancer cells in mice. Synergy with classic anticancer drugs
    • M. Beljanski, and M.S. Beljanski Three alkaloids as selective destroyers of cancer cells in mice. Synergy with classic anticancer drugs Oncology 43 1986 198 203 (Pubitemid 16121737)
    • (1986) Oncology , vol.43 , Issue.3 , pp. 198-203
    • Beljanski, M.1    Beljanski, M.S.2
  • 2
    • 34547927914 scopus 로고    scopus 로고
    • Rapid identification of enzyme variants for reengineered alkaloid biosynthesis in periwinkle
    • DOI 10.1016/j.chembiol.2007.07.008, PII S1074552107002475
    • P. Bernhardt, E. McCoy, and S.E. O'Connor Rapid identification of enzyme variants for reengineered alkaloid biosynthesis in periwinkle Chemistry & Biology 14 2007 888 897 (Pubitemid 47268778)
    • (2007) Chemistry and Biology , vol.14 , Issue.8 , pp. 888-897
    • Bernhardt, P.1    McCoy, E.2    O'Connor, S.E.3
  • 3
    • 0033843763 scopus 로고    scopus 로고
    • 1-deoxy-D-xylulose 5-phosphate synthase from periwinkle: CDNA identification and induced gene expression in terpenoid indole alkaloid-producing cells
    • K. Chahed, A. Oudin, N. Guivarc'h, S. Hamdi, J.C. Chénieux, and M. Rideau 1-deoxy-D-xylulose 5-phosphate synthase from periwinkle: cDNA identification and induced gene expression in terpenoid indole alkaloid-producing cells Plant Physiology and Biochemistry 38 2000 559 566
    • (2000) Plant Physiology and Biochemistry , vol.38 , pp. 559-566
    • Chahed, K.1    Oudin, A.2    Guivarc'H, N.3    Hamdi, S.4    Chénieux, J.C.5    Rideau, M.6
  • 4
    • 84857727692 scopus 로고    scopus 로고
    • Tubulin-based structure-affinity relationships for antimitotic vinca alkaloids
    • C. Coderch, A. Morreale, and F. Gago Tubulin-based structure-affinity relationships for antimitotic vinca alkaloids Anti-Cancer Agents in Medicinal Chemistry 12 3 2012 219 225
    • (2012) Anti-Cancer Agents in Medicinal Chemistry , vol.12 , Issue.3 , pp. 219-225
    • Coderch, C.1    Morreale, A.2    Gago, F.3
  • 5
    • 0036135661 scopus 로고    scopus 로고
    • Activity of the cytochrome P450 enzyme geraniol 10-hydroxylase and alkaloid production in plant cell cultures
    • DOI 10.1016/S0168-9452(01)00554-4, PII S0168945201005544
    • G. Collu, A. Alonso Garcia, R. van der Heijden, and R. Verpoorte Activity of the cytochrome P450 enzyme geraniol 10-hydroxylase and alkaloid production in plant cell cultures Plant Science 162 2002 165 172 (Pubitemid 34016337)
    • (2002) Plant Science , vol.162 , Issue.1 , pp. 165-172
    • Collu, G.1    Garcia, A.A.2    Van Der Heijden, R.3    Verpoorte, R.4
  • 6
    • 0035900382 scopus 로고    scopus 로고
    • Geraniol 10-hydroxylase, a cytochrome P450 enzyme involved in terpenoid indole alkaloid biosynthesis
    • DOI 10.1016/S0014-5793(01)03045-9, PII S0014579301030459
    • G. Collu, N. Unver, A.M. Peltenburg-Looman, R. van der Heijden, R. Verpoorte, and J. Memelink Geraniol 10-hydroxylase, a cytochrome P450 enzyme involved in terpenoid indole alkaloid biosynthesis FEBS Letters 508 2001 215 220 (Pubitemid 33079248)
    • (2001) FEBS Letters , vol.508 , Issue.2 , pp. 215-220
    • Collu, G.1    Unver, N.2    Peltenburg-Looman, A.M.G.3    Van Der Heijden, R.4    Verpoorte, R.5    Memelink, J.6
  • 7
    • 0032423802 scopus 로고    scopus 로고
    • The iridoid glucoside secologanin is derived from the novel triose phosphate/pyruvate pathway in a Catharanthus roseus cell culture
    • DOI 10.1016/S0014-5793(98)01022-9, PII S0014579398010229
    • A. Contin, R. van der Heijden, A.W.M. Lefeber, and R. Verpoorte The iridoid glucoside secologanin is derived from the novel triose phosphate/pyruvate pathway in a Catharanthus roseus cell culture FEBS Letters 434 1998 413 416 (Pubitemid 29052267)
    • (1998) FEBS Letters , vol.434 , Issue.3 , pp. 413-416
    • Contin, A.1    Van Der Heijden, R.2    Lefeber, A.W.M.3    Verpoorte, R.4
  • 9
    • 38949166148 scopus 로고    scopus 로고
    • Molecular cloning and characterization of a vacuolar class III peroxidase involved in the metabolism of anticancer alkaloids in Catharanthus roseus
    • DOI 10.1104/pp.107.107060
    • M.M. Costa, F. Hilliou, P. Duarte, L.G. Pereira, I. Almeida, and M. Leech Molecular cloning and characterization of a vacuolar class III peroxidase involved in the metabolism of anticancer alkaloids in Catharanthus roseus Plant Physiology 146 2008 403 417 (Pubitemid 351230770)
    • (2008) Plant Physiology , vol.146 , Issue.2 , pp. 403-417
    • Costa, M.M.R.1    Hilliou, F.2    Duarte, P.3    Pereira, L.G.4    Almeida, I.5    Leech, M.6    Memelink, J.7    Barcelo, A.R.8    Sottomayor, M.9
  • 10
    • 23044490704 scopus 로고    scopus 로고
    • Plants as a source of anti-cancer agents
    • DOI 10.1016/j.jep.2005.05.011, PII S0378874105003259, Perspectives of Ethnopharmacology
    • G. Cragg, and D. Newman Plants as a source of anti-cancer agents Journal of Ethnopharmacology 100 2005 72 79 (Pubitemid 41073525)
    • (2005) Journal of Ethnopharmacology , vol.100 , Issue.1-2 , pp. 72-79
    • Cragg, G.M.1    Newman, D.J.2
  • 12
    • 0034717060 scopus 로고    scopus 로고
    • Plant aromatic L-amino acid decarboxylases: Evolution, biochemistry, regulation, and metabolic engineering applications
    • DOI 10.1016/S0031-9422(00)00050-9, PII S0031942200000509
    • P.J. Facchini, K.L. Huber-Allanach, and L.W. Tari Plant aromatic L-amino acid decarboxylases: Evolution, biochemistry, regulation, and metabolic engineering applications Phytochemistry 54 2000 121 138 (Pubitemid 30350847)
    • (2000) Phytochemistry , vol.54 , Issue.2 , pp. 121-138
    • Facchini, P.J.1    Huber-Allanach, K.L.2    Tari, L.W.3
  • 13
    • 77953847340 scopus 로고    scopus 로고
    • Vinflunine
    • J.E. Frampton, and M.D. Moen Vinflunine Drugs 70 2010 1283 1293
    • (2010) Drugs , vol.70 , pp. 1283-1293
    • Frampton, J.E.1    Moen, M.D.2
  • 14
    • 34547610198 scopus 로고    scopus 로고
    • Chemoselective derivatization of alkaloids in periwinkle
    • DOI 10.1039/b708919h
    • M.C. Galan, E. McCoy, and S.E. O'Connor Chemoselective derivatization of alkaloids in periwinkle Chemical Communications 2007 3249 3251 (Pubitemid 47197857)
    • (2007) Chemical Communications , Issue.31 , pp. 3249-3251
    • Galan, M.C.1    McCoy, E.2    O'Connor, S.E.3
  • 15
    • 31944449179 scopus 로고    scopus 로고
    • Semi-synthesis of secologanin analogues
    • DOI 10.1016/j.tetlet.2006.01.009, PII S0040403906000414
    • M.C. Galan, and S.E. O'Connor Semi-synthesis of secologanin analogues Tetrahedron Letters 47 2006 1563 1565 (Pubitemid 43187956)
    • (2006) Tetrahedron Letters , vol.47 , Issue.10 , pp. 1563-1565
    • Galan, M.C.1    O'Connor, S.E.2
  • 16
    • 0039596881 scopus 로고    scopus 로고
    • Molecular cloning and analysis of strictosidine -D-glucosidase, an enzyme in terpenoid indole alkaloid biosynthesis in Catharanthus roseus
    • DOI 10.1074/jbc.275.5.3051
    • A. Geerlings, M.M.-L. Ibanez, J. Memelink, R. Van der Heijden, and R. Verpoorte Molecular cloning and analysis of strictosidine b-D-glucosidase, an enzyme in terpenoid indole alkaloid biosynthesis in Catharanthus roseus The Journal of Biological Chemistry 275 2000 3051 3056 (Pubitemid 30082999)
    • (2000) Journal of Biological Chemistry , vol.275 , Issue.5 , pp. 3051-3056
    • Geerlings, A.1    Ibanez, M.M.-L.2    Memelink, J.3    Van Der Heijden, R.4    Verpoorte, R.5
  • 17
    • 0036233184 scopus 로고    scopus 로고
    • Heterologous expression of a Rauvolfia cDNA encoding strictosidine glucosidase, a biosynthetic key to over 2000 monoterpenoid indole alkaloids
    • DOI 10.1046/j.1432-1033.2002.02878.x
    • I. Gerasimenko, Y. Sheludko, X. Ma, and J. Stockigt Heterologous expression of a Rauvolfia cDNA encoding strictosidine glucosidase, a biosynthetic key to over 2000 monoterpenoid indole alkaloids European Journal of Biochemistry 269 2002 2204 2213 (Pubitemid 34437864)
    • (2002) European Journal of Biochemistry , vol.269 , Issue.8 , pp. 2204-2213
    • Gerasimenko, I.1    Sheludko, Y.2    Ma, X.3    Stockigt, J.4
  • 19
    • 0038725902 scopus 로고    scopus 로고
    • Constructs and methods for high-throughput gene silencing in plants
    • DOI 10.1016/S1046-2023(03)00036-7
    • C. Helliwell, and P. Waterhouse Constructs and methods for high-throughput gene silencing in plants Methods 30 2003 289 295 (Pubitemid 36793965)
    • (2003) Methods , vol.30 , Issue.4 , pp. 289-295
    • Helliwell, C.1    Waterhouse, P.2
  • 20
    • 2242492677 scopus 로고    scopus 로고
    • Characterization of an inducible promoter system in Catharanthus roseus hairy roots
    • DOI 10.1021/bp025603o
    • E.H. Hughes, S.B. Hong, J.V. Shanks, K.-Y. San, and S.I. Gibson Characterization of an inducible promoter system in Catharanthus roseus hairy roots Biotechnology Progress 18 2002 1183 1186 (Pubitemid 35450873)
    • (2002) Biotechnology Progress , vol.18 , Issue.6 , pp. 1183-1186
    • Hughes, E.H.1    Hong, S.-B.2    Shanks, J.V.3    San, K.-Y.4    Gibson, S.I.5
  • 21
    • 0034490132 scopus 로고    scopus 로고
    • Indole alkaloid biosynthesis in Catharanthus roseus: New enzyme activities and identification of cytochrome P450 CYP72A1 as secologanin synthase
    • DOI 10.1046/j.1365-313X.2000.00922.x
    • S. Irmler, G. Schroder, B. St-Pierre, N.P. Crouch, M. Hotze, and J. Schmidt Indole alkaloid biosynthesis in Catharanthus roseus: New enzyme activities and identification of cytochrome P450 CYP72A1 as secologanin synthase The Plant Journal 24 2000 797 804 (Pubitemid 32100477)
    • (2000) Plant Journal , vol.24 , Issue.6 , pp. 797-804
    • Irmler, S.1    Schroder, G.2    St-Pierre, B.3    Crouch, N.P.4    Hotze, M.5    Schmidt, J.6    Strack, D.7    Matern, U.8    Schroder, J.9
  • 22
    • 40149110727 scopus 로고    scopus 로고
    • Direct coupling of catharanthine and vindoline to provide vinblastine: Total synthesis of (+)- and ent-(-)-vinblastine
    • DOI 10.1021/ja078192m
    • H. Ishikawa, D.A. Colby, and D.L. Boger Direct coupling of catharanthine and vindoline to provide vinblastine: Total synthesis of (+)- and ent-(-)-vinblastine Journal of the American Chemical Society 130 2008 420 421 (Pubitemid 351455538)
    • (2008) Journal of the American Chemical Society , vol.130 , Issue.2 , pp. 420-421
    • Ishikawa, H.1    Colby, D.A.2    Boger, D.L.3
  • 26
    • 34548694786 scopus 로고    scopus 로고
    • Structure-based engineering of strictosidine synthase: Auxiliary for alkaloid libraries
    • DOI 10.1016/j.chembiol.2007.08.009, PII S1074552107002888
    • E.A. Loris, S. Panjikar, M. Ruppert, L. Barleben, M. Unger, and H. Schubel Structure-based engineering of strictosidine synthase: Auxiliary for alkaloid libraries Chemistry & Biology 14 2007 979 985 (Pubitemid 47411614)
    • (2007) Chemistry and Biology , vol.14 , Issue.9 , pp. 979-985
    • Loris, E.A.1    Panjikar, S.2    Ruppert, M.3    Barleben, L.4    Unger, M.5    Schubel, H.6    Stockigt, J.7
  • 27
    • 33745473834 scopus 로고    scopus 로고
    • The structure of Rauvolfia serpentina strictosidine synthase is a novel six-bladed propeller fold in plant proteins
    • DOI 10.1105/tpc.105.038018
    • X. Ma, S. Panjikar, J. Koepke, E. Loris, and J. Stockigt The structure of Rauvolfia serpentina strictosidine synthase is a novel six-bladed beta-propeller fold in plant proteins The Plant Cell 18 2006 907 920 (Pubitemid 43956144)
    • (2006) Plant Cell , vol.18 , Issue.4 , pp. 907-920
    • Ma, X.1    Panjikar, S.2    Koepke, J.3    Loris, E.4    Stockigt, J.5
  • 29
    • 33750728402 scopus 로고    scopus 로고
    • Directed biosynthesis of alkaloid analogs in the medicinal plant Catharanthus roseus
    • DOI 10.1021/ja066787w
    • E. McCoy, and S.E. O'Connor Directed biosynthesis of alkaloid analogs in the medicinal plant Catharanthus roseus Journal of the American Chemical Society 128 2006 14276 14277 (Pubitemid 44707735)
    • (2006) Journal of the American Chemical Society , vol.128 , Issue.44 , pp. 14276-14277
    • McCoy, E.1    O'Connor, S.E.2
  • 30
    • 48249155450 scopus 로고    scopus 로고
    • The leaf epidermome of Catharanthus roseus reveals its biochemical specialization
    • DOI 10.1105/tpc.107.056630
    • J. Murata, J. Roepke, H. Gordon, and V. De Luca The leaf epidermome of Catharanthus roseus reveals its biochemical specialization The Plant Cell 20 2008 524 542 (Pubitemid 352843990)
    • (2008) Plant Cell , vol.20 , Issue.3 , pp. 524-542
    • Murata, J.1    Roepke, J.2    Gordon, H.3    De Luca, V.4
  • 31
    • 0034665163 scopus 로고    scopus 로고
    • Novel actions of the antitumor drugs vinflunine and vinorelbine on microtubules
    • V.K. Ngan, K. Bellman, D. Panda, B.T. Hill, M.A. Jordan, and L. Wilson Novel actions of the antitumor drugs vinflunine and vinorelbine on microtubules Cancer Research 60 2000 5045 5051
    • (2000) Cancer Research , vol.60 , pp. 5045-5051
    • Ngan, V.K.1    Bellman, K.2    Panda, D.3    Hill, B.T.4    Jordan, M.A.5    Wilson, L.6
  • 32
    • 0025641040 scopus 로고
    • The discovery of the vinca alkaloids-chemotherapeutic agents against cancer
    • R.L. Noble The discovery of the vinca alkaloids-chemotherapeutic agents against cancer Biochimie Et Biologie Cellulaire 68 1990 1344 1351
    • (1990) Biochimie et Biologie Cellulaire , vol.68 , pp. 1344-1351
    • Noble, R.L.1
  • 33
    • 33746520558 scopus 로고    scopus 로고
    • Chemistry and biology of monoterpene indole alkaloid biosynthesis
    • DOI 10.1039/b512615k
    • S.E. O'Connor, and J.J. Maresh Chemistry and biology of monoterpene indole alkaloid biosynthesis Natural Product Reports 23 2006 532 547 (Pubitemid 44141692)
    • (2006) Natural Product Reports , vol.23 , Issue.4 , pp. 532-547
    • O'Connor, S.E.1    Maresh, J.J.2
  • 34
    • 81355135430 scopus 로고    scopus 로고
    • Combinatorial biosynthesis in plants: A (p)review on its potential and future exploitation
    • J. Pollier, T. Moses, and A. Goossens Combinatorial biosynthesis in plants: A (p)review on its potential and future exploitation Natural Product Reports 28 2011 1897 1916
    • (2011) Natural Product Reports , vol.28 , pp. 1897-1916
    • Pollier, J.1    Moses, T.2    Goossens, A.3
  • 35
    • 0012044432 scopus 로고
    • Interconversion of corynanthe, aspidosperma and iboga alkaloids a model for indole alkaloid biosynthesis
    • A.A. Qureshi, and A.I. Scott Interconversion of corynanthe, aspidosperma and iboga alkaloids a model for indole alkaloid biosynthesis Chemical Communications 1968 945 946
    • (1968) Chemical Communications , pp. 945-946
    • Qureshi, A.A.1    Scott, A.I.2
  • 37
    • 60249093108 scopus 로고    scopus 로고
    • Metabolic reprogramming of periwinkle plant culture
    • W. Runguphan, and S.E. O'Connor Metabolic reprogramming of periwinkle plant culture Nature Chemical Biology 5 2009 151 153
    • (2009) Nature Chemical Biology , vol.5 , pp. 151-153
    • Runguphan, W.1    O'Connor, S.E.2
  • 39
    • 0037462106 scopus 로고    scopus 로고
    • Activity-based protein profiling in vivo using a copper(I)-catalyzed azide-alkyne [3 + 2] cycloaddition
    • DOI 10.1021/ja034490h
    • A.E. Speers, G.C. Adam, and B.F. Cravatt Activity-based protein profiling in vivo using a copper(i)-catalyzed azide-alkyne [3 + 2] cycloaddition Journal of the American Chemical Society 125 2003 4686 4687 (Pubitemid 36505343)
    • (2003) Journal of the American Chemical Society , vol.125 , Issue.16 , pp. 4686-4687
    • Speers, A.E.1    Adam, G.C.2    Cravatt, B.F.3
  • 40
    • 0029310653 scopus 로고
    • Combinatorial biosynthesis of 'unnatural' natural products: The polyketide example
    • C.J. Tsoi, and C. Khosla Combinatorial biosynthesis of 'unnatural' natural products: The polyketide example Chemistry & Biology 2 1995 355 362
    • (1995) Chemistry & Biology , vol.2 , pp. 355-362
    • Tsoi, C.J.1    Khosla, C.2
  • 43
    • 33947160920 scopus 로고    scopus 로고
    • Mutasynthesis - uniting chemistry and genetics for drug discovery
    • DOI 10.1016/j.tibtech.2007.02.004, PII S0167779907000273
    • K.J. Weissman Mutasynthesis - Uniting chemistry and genetics for drug discovery Trends in Biotechnology 25 2007 139 142 (Pubitemid 46413365)
    • (2007) Trends in Biotechnology , vol.25 , Issue.4 , pp. 139-142
    • Weissman, K.J.1
  • 44
    • 44949127129 scopus 로고    scopus 로고
    • Alkaloid biosynthesis: Metabolism and trafficking
    • DOI 10.1146/annurev.arplant.59.032607.092730
    • J. Ziegler, and P.J. Facchini Alkaloid biosynthesis: Metabolism and trafficking Annual Review of Plant Biology 59 2008 735 769 (Pubitemid 351813049)
    • (2008) Annual Review of Plant Biology , vol.59 , pp. 735-769
    • Ziegler, J.1    Facchini, P.J.2


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.