메뉴 건너뛰기




Volumn 18, Issue , 2013, Pages 69-77

Combinatorial biosynthesis of plant-specific coumarins in bacteria

Author keywords

Combinatorial biosynthesis; Coumarin; Plant metabolites; Scopoletin; Umbelliferone

Indexed keywords

COMBINATORIAL BIOSYNTHESIS; COUMARIN; PLANT METABOLITES; SCOPOLETIN; UMBELLIFERONE;

EID: 84878364563     PISSN: 10967176     EISSN: 10967184     Source Type: Journal    
DOI: 10.1016/j.ymben.2013.04.004     Document Type: Article
Times cited : (83)

References (59)
  • 2
    • 77952517931 scopus 로고    scopus 로고
    • Biosynthesis: is it time to go retro?
    • Bachmann B.O. Biosynthesis: is it time to go retro?. Nat. Chem. Biol. 2010, 6:390-393.
    • (2010) Nat. Chem. Biol. , vol.6 , pp. 390-393
    • Bachmann, B.O.1
  • 3
    • 27844474247 scopus 로고    scopus 로고
    • Drug discovery from medicinal plants
    • Balunas M..J., Kinghorn A..D. Drug discovery from medicinal plants. Life Sci. 2005, 78:431-441.
    • (2005) Life Sci. , vol.78 , pp. 431-441
    • Balunas, M..J.1    Kinghorn, A..D.2
  • 4
    • 33845445814 scopus 로고    scopus 로고
    • Biosynthesis of coumarins in plants: a major pathway still to be unravelled for cytochrome P450 enzymes
    • Bourgaud F., Hehn A., Larbat R., Doerper S., Gontier E., Kellner S., Matern U. Biosynthesis of coumarins in plants: a major pathway still to be unravelled for cytochrome P450 enzymes. Phytochem. Rev. 2006, 5:293-308.
    • (2006) Phytochem. Rev. , vol.5 , pp. 293-308
    • Bourgaud, F.1    Hehn, A.2    Larbat, R.3    Doerper, S.4    Gontier, E.5    Kellner, S.6    Matern, U.7
  • 5
    • 11344292132 scopus 로고    scopus 로고
    • The role of natural product chemistry in drug discovery
    • Butler M.S. The role of natural product chemistry in drug discovery. J. Nat. Prod. 2004, 67:2141-2153.
    • (2004) J. Nat. Prod. , vol.67 , pp. 2141-2153
    • Butler, M.S.1
  • 6
    • 44249098800 scopus 로고    scopus 로고
    • Natural products to drugs: natural product-derived compounds in clinical trials
    • Butler M.S. Natural products to drugs: natural product-derived compounds in clinical trials. Nat. Prod. Rep. 2008, 25:475-516.
    • (2008) Nat. Prod. Rep. , vol.25 , pp. 475-516
    • Butler, M.S.1
  • 7
    • 57649100762 scopus 로고    scopus 로고
    • Metabolic engineering for plant natural product biosynthesis in microbes
    • Chemler J.A., Koffas M.A. Metabolic engineering for plant natural product biosynthesis in microbes. Curr. Opin. Biotechnol. 2008, 19:597-605.
    • (2008) Curr. Opin. Biotechnol. , vol.19 , pp. 597-605
    • Chemler, J.A.1    Koffas, M.A.2
  • 9
    • 78049450967 scopus 로고    scopus 로고
    • Genetic alterations for increased coumarin production lead to metabolic changes in the medicinally important Pelargonium sidoides DC (Geraniaceae)
    • Colling J., Groenewald J.H., Makunga N.P. Genetic alterations for increased coumarin production lead to metabolic changes in the medicinally important Pelargonium sidoides DC (Geraniaceae). Metab. Eng. 2010, 12:561-572.
    • (2010) Metab. Eng. , vol.12 , pp. 561-572
    • Colling, J.1    Groenewald, J.H.2    Makunga, N.P.3
  • 10
    • 0031028432 scopus 로고    scopus 로고
    • Natural products in drug discovery and development
    • Cragg G.M., Newman D.J., Snader K.M. Natural products in drug discovery and development. J. Nat. Prod. 1997, 60:52-60.
    • (1997) J. Nat. Prod. , vol.60 , pp. 52-60
    • Cragg, G.M.1    Newman, D.J.2    Snader, K.M.3
  • 11
    • 0039552100 scopus 로고    scopus 로고
    • Three 4-coumarate:coenzyme A ligases in Arabidopsis thaliana represent two evolutionarily divergent classes in angiosperms
    • Ehlting J., Buttner D., Wang Q., Douglas C.J., Somssich I.E., Kombrink E. Three 4-coumarate:coenzyme A ligases in Arabidopsis thaliana represent two evolutionarily divergent classes in angiosperms. Plant J. 1999, 19:9-20.
    • (1999) Plant J. , vol.19 , pp. 9-20
    • Ehlting, J.1    Buttner, D.2    Wang, Q.3    Douglas, C.J.4    Somssich, I.E.5    Kombrink, E.6
  • 12
    • 0034024497 scopus 로고    scopus 로고
    • Improving lycopene production in Escherichia coli by engineering metabolic control
    • Farmer W.R., Liao J.C. Improving lycopene production in Escherichia coli by engineering metabolic control. Nat. Biotechnol. 2000, 18:533-537.
    • (2000) Nat. Biotechnol. , vol.18 , pp. 533-537
    • Farmer, W.R.1    Liao, J.C.2
  • 14
    • 0016176230 scopus 로고
    • The 2-hydroxylation of trans-cinnamic acid by chloroplasts from Melilotus alba Desr
    • Gestetner B., Conn E.E. The 2-hydroxylation of trans-cinnamic acid by chloroplasts from Melilotus alba Desr. Arch. Biochem. Biophys. 1974, 163:617-624.
    • (1974) Arch. Biochem. Biophys. , vol.163 , pp. 617-624
    • Gestetner, B.1    Conn, E.E.2
  • 16
    • 0023715078 scopus 로고
    • A new coumarin synthesis and its utilization for the synthesis of polycyclic coumarin compounds with anticarcinogenic properties
    • Harvey R.G., Cortez C., Ananthanarayan T.P., Schmolka S. A new coumarin synthesis and its utilization for the synthesis of polycyclic coumarin compounds with anticarcinogenic properties. J. Org. Chem. 1988, 53:3936-3943.
    • (1988) J. Org. Chem. , vol.53 , pp. 3936-3943
    • Harvey, R.G.1    Cortez, C.2    Ananthanarayan, T.P.3    Schmolka, S.4
  • 17
    • 4143147424 scopus 로고
    • Light-induced trans to cis conversion of beta-d-glucosyl o-hydroxycinnamic acid in Melilotus alba leaves
    • Haskins F.A., Williams L.G., Gorz H.J. Light-induced trans to cis conversion of beta-d-glucosyl o-hydroxycinnamic acid in Melilotus alba leaves. Plant Physiol. 1964, 39:777-781.
    • (1964) Plant Physiol. , vol.39 , pp. 777-781
    • Haskins, F.A.1    Williams, L.G.2    Gorz, H.J.3
  • 18
    • 49949088247 scopus 로고    scopus 로고
    • Production of benzylisoquinoline alkaloids in Saccharomyces cerevisiae
    • Hawkins K.M., Smolke C.D. Production of benzylisoquinoline alkaloids in Saccharomyces cerevisiae. Nat. Chem. Biol. 2008, 4:564-573.
    • (2008) Nat. Chem. Biol. , vol.4 , pp. 564-573
    • Hawkins, K.M.1    Smolke, C.D.2
  • 19
    • 0034838359 scopus 로고    scopus 로고
    • Engineering Escherichia coli for the synthesis of taxadiene, a key intermediate in the biosynthesis of taxol
    • Huang Q., Roessner C.A., Croteau R., Scott A.I. Engineering Escherichia coli for the synthesis of taxadiene, a key intermediate in the biosynthesis of taxol. Bioorg. Med. Chem. 2001, 9:2237-2242.
    • (2001) Bioorg. Med. Chem. , vol.9 , pp. 2237-2242
    • Huang, Q.1    Roessner, C.A.2    Croteau, R.3    Scott, A.I.4
  • 21
    • 51449121245 scopus 로고    scopus 로고
    • Scopoletin is biosynthesized via ortho-hydroxylation of feruloyl CoA by a 2-oxoglutarate-dependent dioxygenase in Arabidopsis thaliana
    • Kai K., Mizutani M., Kawamura N., Yamamoto R., Tamai M., Yamaguchi H., Sakata K., Shimizu B. Scopoletin is biosynthesized via ortho-hydroxylation of feruloyl CoA by a 2-oxoglutarate-dependent dioxygenase in Arabidopsis thaliana. Plant J. 2008, 55:989-999.
    • (2008) Plant J. , vol.55 , pp. 989-999
    • Kai, K.1    Mizutani, M.2    Kawamura, N.3    Yamamoto, R.4    Tamai, M.5    Yamaguchi, H.6    Sakata, K.7    Shimizu, B.8
  • 22
    • 0346328227 scopus 로고    scopus 로고
    • Metabolic engineering for drug discovery and development
    • Khosla C., Keasling J.D. Metabolic engineering for drug discovery and development. Nat. Rev. Drug Discov. 2003, 2:1019-1025.
    • (2003) Nat. Rev. Drug Discov. , vol.2 , pp. 1019-1025
    • Khosla, C.1    Keasling, J.D.2
  • 23
    • 0342635722 scopus 로고
    • Trans-o-hydroxycinnamic acid glucosylation in cell-free extracts of Melilotus alba
    • Kleinhofs A., Haskins F.A., Gorz H.J. Trans-o-hydroxycinnamic acid glucosylation in cell-free extracts of Melilotus alba. Phytochemistry 1967, 6:1313-1318.
    • (1967) Phytochemistry , vol.6 , pp. 1313-1318
    • Kleinhofs, A.1    Haskins, F.A.2    Gorz, H.J.3
  • 25
    • 33645235123 scopus 로고    scopus 로고
    • Structure-activity relationships of synthetic coumarins as HIV-1 inhibitors
    • Kostova I., Raleva S., Genova P., Argirova R. Structure-activity relationships of synthetic coumarins as HIV-1 inhibitors. Bioinorg. Chem. Appl. 2006, 68274.
    • (2006) Bioinorg. Chem. Appl. , pp. 68274
    • Kostova, I.1    Raleva, S.2    Genova, P.3    Argirova, R.4
  • 26
    • 6944237046 scopus 로고    scopus 로고
    • Studies on coumarins and coumarin-related compounds to determine their therapeutic role in the treatment of cancer
    • Lacy A., O'Kennedy R. Studies on coumarins and coumarin-related compounds to determine their therapeutic role in the treatment of cancer. Curr. Pharm. Des. 2004, 10:3797-3811.
    • (2004) Curr. Pharm. Des. , vol.10 , pp. 3797-3811
    • Lacy, A.1    O'Kennedy, R.2
  • 27
    • 34250849659 scopus 로고    scopus 로고
    • Engineering central metabolic pathways for high-level flavonoid production in Escherichia coli
    • Leonard E., Lim K.H., Saw P.N., Koffas M.A. Engineering central metabolic pathways for high-level flavonoid production in Escherichia coli. Appl. Environ. Microbiol. 2007, 73:3877-3886.
    • (2007) Appl. Environ. Microbiol. , vol.73 , pp. 3877-3886
    • Leonard, E.1    Lim, K.H.2    Saw, P.N.3    Koffas, M.A.4
  • 29
    • 84938746622 scopus 로고    scopus 로고
    • Biosynthesis of caffeic acid in Escherichia coli using its endogenous hydroxylase complex
    • Lin Y., Yan Y. Biosynthesis of caffeic acid in Escherichia coli using its endogenous hydroxylase complex. Microb. Cell. Fact. 2012, 11:42.
    • (2012) Microb. Cell. Fact. , vol.11 , pp. 42
    • Lin, Y.1    Yan, Y.2
  • 30
    • 0030861452 scopus 로고    scopus 로고
    • Independent and tight regulation of transcriptional units in Escherichia coli via the LacR/O, the TetR/O and AraC/I1-I2 regulatory elements
    • Lutz R., Bujard H. Independent and tight regulation of transcriptional units in Escherichia coli via the LacR/O, the TetR/O and AraC/I1-I2 regulatory elements. Nucleic Acids Res. 1997, 25:1203-1210.
    • (1997) Nucleic Acids Res. , vol.25 , pp. 1203-1210
    • Lutz, R.1    Bujard, H.2
  • 31
    • 0026214247 scopus 로고
    • Phase I evaluation of coumarin (1,2-benzopyrone) and cimetidine in patients with advanced malignancies
    • Marshall M.E., Butler K., Fried A. Phase I evaluation of coumarin (1,2-benzopyrone) and cimetidine in patients with advanced malignancies. Mol. Biol. Ther. 1991, 3:170-178.
    • (1991) Mol. Biol. Ther. , vol.3 , pp. 170-178
    • Marshall, M.E.1    Butler, K.2    Fried, A.3
  • 32
    • 84855941192 scopus 로고    scopus 로고
    • Molecular cloning and functional analysis of the ortho-hydroxylases of p-coumaroyl coenzyme A/feruloyl coenzyme A involved in formation of umbelliferone and scopoletin in sweet potato, Ipomoea batatas (L.) Lam
    • Matsumoto S., Mizutani M., Sakata K., Shimizu B. Molecular cloning and functional analysis of the ortho-hydroxylases of p-coumaroyl coenzyme A/feruloyl coenzyme A involved in formation of umbelliferone and scopoletin in sweet potato, Ipomoea batatas (L.) Lam. Phytochemistry 2012, 74:49-57.
    • (2012) Phytochemistry , vol.74 , pp. 49-57
    • Matsumoto, S.1    Mizutani, M.2    Sakata, K.3    Shimizu, B.4
  • 33
    • 34447096207 scopus 로고    scopus 로고
    • Plant natural products: back to the future or into extinction?
    • McChesney J.D., Venkataraman S.K., Henri J.T. Plant natural products: back to the future or into extinction?. Phytochemistry 2007, 68:2015-2022.
    • (2007) Phytochemistry , vol.68 , pp. 2015-2022
    • McChesney, J.D.1    Venkataraman, S.K.2    Henri, J.T.3
  • 35
    • 79961008636 scopus 로고    scopus 로고
    • Natural products from synthetic biology
    • Mitchell W. Natural products from synthetic biology. Curr. Opin. Chem. Biol. 2011, 15:505-515.
    • (2011) Curr. Opin. Chem. Biol. , vol.15 , pp. 505-515
    • Mitchell, W.1
  • 37
    • 61749102591 scopus 로고    scopus 로고
    • A review of coumarin derivatives in pharmacotherapy of breast cancer
    • Musa M.A., Cooperwood J.S., Khan M.O. A review of coumarin derivatives in pharmacotherapy of breast cancer. Curr. Med. Chem. 2008, 15:2664-2679.
    • (2008) Curr. Med. Chem. , vol.15 , pp. 2664-2679
    • Musa, M.A.1    Cooperwood, J.S.2    Khan, M.O.3
  • 39
    • 34247109045 scopus 로고    scopus 로고
    • Natural products as sources of new drugs over the last 25 years
    • Newman D.J., Cragg G.M. Natural products as sources of new drugs over the last 25 years. J. Nat. Prod. 2007, 70:461-477.
    • (2007) J. Nat. Prod. , vol.70 , pp. 461-477
    • Newman, D.J.1    Cragg, G.M.2
  • 40
    • 0034082239 scopus 로고    scopus 로고
    • The influence of natural products upon drug discovery
    • Newman D.J., Cragg G.M., Snader K.M. The influence of natural products upon drug discovery. Nat. Prod. Rep. 2000, 17:215-234.
    • (2000) Nat. Prod. Rep. , vol.17 , pp. 215-234
    • Newman, D.J.1    Cragg, G.M.2    Snader, K.M.3
  • 41
    • 0042844744 scopus 로고    scopus 로고
    • Natural products as sources of new drugs over the period 1981-2002
    • Newman D.J., Cragg G.M., Snader K.M. Natural products as sources of new drugs over the period 1981-2002. J. Nat. Prod. 2003, 66:1022-1037.
    • (2003) J. Nat. Prod. , vol.66 , pp. 1022-1037
    • Newman, D.J.1    Cragg, G.M.2    Snader, K.M.3
  • 42
    • 0010258055 scopus 로고
    • Subcellular localization of 2-(beta-d-glucosyloxy)-cinnamic acids and the related beta-glucosidase in leaves of Melilotus alba Desr
    • Oba K., Conn E.E., Canut H., Boudet A.M. Subcellular localization of 2-(beta-d-glucosyloxy)-cinnamic acids and the related beta-glucosidase in leaves of Melilotus alba Desr. Plant Physiol. 1981, 68:1359-1363.
    • (1981) Plant Physiol. , vol.68 , pp. 1359-1363
    • Oba, K.1    Conn, E.E.2    Canut, H.3    Boudet, A.M.4
  • 43
    • 27144547510 scopus 로고    scopus 로고
    • The renaissance of natural products as drug candidates
    • Paterson I., Anderson E.A. The renaissance of natural products as drug candidates. Science 2005, 310:451-453.
    • (2005) Science , vol.310 , pp. 451-453
    • Paterson, I.1    Anderson, E.A.2
  • 44
    • 33750994151 scopus 로고
    • Intracellular localization of two enzymes involved in coumarin biosynthesis in Melilotus alba
    • Poulton J.E., McRee D.E., Conn E.E. Intracellular localization of two enzymes involved in coumarin biosynthesis in Melilotus alba. Plant Physiol. 1980, 65:171-175.
    • (1980) Plant Physiol. , vol.65 , pp. 171-175
    • Poulton, J.E.1    McRee, D.E.2    Conn, E.E.3
  • 47
    • 79958715193 scopus 로고    scopus 로고
    • Optimization of a heterologous pathway for the production of flavonoids from glucose
    • Santos C.N., Koffas M., Stephanopoulos G. Optimization of a heterologous pathway for the production of flavonoids from glucose. Metab. Eng. 2011, 13:392-400.
    • (2011) Metab. Eng. , vol.13 , pp. 392-400
    • Santos, C.N.1    Koffas, M.2    Stephanopoulos, G.3
  • 48
    • 54349114978 scopus 로고    scopus 로고
    • Metabolic engineering of Escherichia coli for 1-butanol and 1-propanol production via the keto-acid pathways
    • Shen C.R., Liao J.C. Metabolic engineering of Escherichia coli for 1-butanol and 1-propanol production via the keto-acid pathways. Metab. Eng. 2008, 10:312-320.
    • (2008) Metab. Eng. , vol.10 , pp. 312-320
    • Shen, C.R.1    Liao, J.C.2
  • 49
    • 41349091302 scopus 로고    scopus 로고
    • Synthesis, computational study and cytotoxic activity of new 4-hydroxycoumarin derivatives
    • Stanchev S., Momekov G., Jensen F., Manolov I. Synthesis, computational study and cytotoxic activity of new 4-hydroxycoumarin derivatives. Eur. J. Med. Chem. 2008, 43:694-706.
    • (2008) Eur. J. Med. Chem. , vol.43 , pp. 694-706
    • Stanchev, S.1    Momekov, G.2    Jensen, F.3    Manolov, I.4
  • 50
    • 0040454756 scopus 로고
    • The biosynthesis of coumarin in Melilotus alba
    • Stoker J.R., Bellis D.M. The biosynthesis of coumarin in Melilotus alba. J. Biol. Chem. 1962, 237:2303-2305.
    • (1962) J. Biol. Chem. , vol.237 , pp. 2303-2305
    • Stoker, J.R.1    Bellis, D.M.2
  • 52
    • 33847252518 scopus 로고    scopus 로고
    • Production of p-hydroxycinnamic acid from glucose in Saccharomyces cerevisiae and Escherichia coli by expression of heterologous genes from plants and fungi
    • Vannelli T., Wei Qi W., Sweigard J., Gatenby A.A., Sariaslani F.S. Production of p-hydroxycinnamic acid from glucose in Saccharomyces cerevisiae and Escherichia coli by expression of heterologous genes from plants and fungi. Metab. Eng. 2007, 9:142-151.
    • (2007) Metab. Eng. , vol.9 , pp. 142-151
    • Vannelli, T.1    Wei Qi, W.2    Sweigard, J.3    Gatenby, A.A.4    Sariaslani, F.S.5
  • 53
    • 84859561004 scopus 로고    scopus 로고
    • A 2-oxoglutarate-dependent dioxygenase from Ruta graveolens L. exhibits p-coumaroyl CoA 2'-hydroxylase activity (C2'H): a missing step in the synthesis of umbelliferone in plants
    • Vialart G., Hehn A., Olry A., Ito K., Krieger C., Larbat R., Paris C., Shimizu B., Sugimoto Y., Mizutani M., Bourgaud F. A 2-oxoglutarate-dependent dioxygenase from Ruta graveolens L. exhibits p-coumaroyl CoA 2'-hydroxylase activity (C2'H): a missing step in the synthesis of umbelliferone in plants. Plant J. 2012, 70:460-470.
    • (2012) Plant J. , vol.70 , pp. 460-470
    • Vialart, G.1    Hehn, A.2    Olry, A.3    Ito, K.4    Krieger, C.5    Larbat, R.6    Paris, C.7    Shimizu, B.8    Sugimoto, Y.9    Mizutani, M.10    Bourgaud, F.11
  • 55
    • 25144431998 scopus 로고    scopus 로고
    • Biosynthesis of natural flavanones in Saccharomyces cerevisiae
    • Yan Y., Kohli A., Koffas M.A. Biosynthesis of natural flavanones in Saccharomyces cerevisiae. Appl. Environ. Microbiol. 2005, 71:5610-5613.
    • (2005) Appl. Environ. Microbiol. , vol.71 , pp. 5610-5613
    • Yan, Y.1    Kohli, A.2    Koffas, M.A.3
  • 56
    • 35748974224 scopus 로고    scopus 로고
    • Biosynthesis of 5-deoxyflavanones in microorganisms
    • Yan Y., Huang L., Koffas M.A. Biosynthesis of 5-deoxyflavanones in microorganisms. Biotechnol. J. 2007, 2:1250-1262.
    • (2007) Biotechnol. J. , vol.2 , pp. 1250-1262
    • Yan, Y.1    Huang, L.2    Koffas, M.A.3
  • 57
    • 42549160385 scopus 로고    scopus 로고
    • High-yield anthocyanin biosynthesis in engineered Escherichia coli
    • Yan Y., Li Z., Koffas M.A. High-yield anthocyanin biosynthesis in engineered Escherichia coli. Biotechnol. Bioeng. 2008, 100:126-140.
    • (2008) Biotechnol. Bioeng. , vol.100 , pp. 126-140
    • Yan, Y.1    Li, Z.2    Koffas, M.A.3
  • 59
    • 57049185719 scopus 로고    scopus 로고
    • Engineering natural products using combinatorial biosynthesis and biocatalysis
    • Zhou H., Xie X., Tang Y. Engineering natural products using combinatorial biosynthesis and biocatalysis. Curr. Opin. Biotechnol. 2008, 19:590-596.
    • (2008) Curr. Opin. Biotechnol. , vol.19 , pp. 590-596
    • Zhou, H.1    Xie, X.2    Tang, Y.3


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.