메뉴 건너뛰기




Volumn 4, Issue 9, 2008, Pages 564-573

Production of benzylisoquinoline alkaloids in Saccharomyces cerevisiae

Author keywords

[No Author keywords available]

Indexed keywords

ALKALOID DERIVATIVE; BENZYLISOQUINOLINE ALKALOID; BENZYLISOQUINOLINE DERIVATIVE; BERBERINE; CYTOCHROME P450; MORPHINAN DERIVATIVE; RETICULINE; SALUTARIDIN; SANGUINARINE; UNCLASSIFIED DRUG;

EID: 49949088247     PISSN: 15524450     EISSN: 15524469     Source Type: Journal    
DOI: 10.1038/nchembio.105     Document Type: Article
Times cited : (278)

References (44)
  • 1
    • 28544451327 scopus 로고    scopus 로고
    • Foundations for engineering biology
    • Endy, D. Foundations for engineering biology. Nature 438, 449-453 (2005).
    • (2005) Nature , vol.438 , pp. 449-453
    • Endy, D.1
  • 2
    • 23444461901 scopus 로고    scopus 로고
    • Advances in synthetic biology: On the path from prototypes to applications
    • McDaniel, R. & Weiss, R. Advances in synthetic biology: on the path from prototypes to applications. Curr. Opin. Biotechnol. 16, 476-483 (2005).
    • (2005) Curr. Opin. Biotechnol , vol.16 , pp. 476-483
    • McDaniel, R.1    Weiss, R.2
  • 3
    • 33645870422 scopus 로고    scopus 로고
    • Production of the antimalarial drug precursor artemisinic acid in engineered yeast
    • Ro, D.K. et al. Production of the antimalarial drug precursor artemisinic acid in engineered yeast. Nature 440, 940-943 (2006).
    • (2006) Nature , vol.440 , pp. 940-943
    • Ro, D.K.1
  • 4
    • 0031905709 scopus 로고    scopus 로고
    • Production of a polyketide natural product in nonpolyketide-producing prokaryotic and eukaryotic hosts
    • Kealey, J.T., Liu, L., Santi, D.V., Betlach, M.C. & Barr, P.J. Production of a polyketide natural product in nonpolyketide-producing prokaryotic and eukaryotic hosts. Proc. Natl. Acad. Sci. USA 95, 505-509 (1998).
    • (1998) Proc. Natl. Acad. Sci. USA , vol.95 , pp. 505-509
    • Kealey, J.T.1    Liu, L.2    Santi, D.V.3    Betlach, M.C.4    Barr, P.J.5
  • 5
    • 0037313962 scopus 로고    scopus 로고
    • Total biosynthesis of hydrocortisone from a simple carbon source in yeast
    • Szczebara, F.M. et al. Total biosynthesis of hydrocortisone from a simple carbon source in yeast. Nat. Biotechnol. 21, 143-149 (2003).
    • (2003) Nat. Biotechnol , vol.21 , pp. 143-149
    • Szczebara, F.M.1
  • 6
    • 0027472156 scopus 로고
    • Antispasmodic activity of benzylisoquinoline alkaloids analogous to papaverine
    • Martin, M.L. et al. Antispasmodic activity of benzylisoquinoline alkaloids analogous to papaverine. Planta Med. 59, 63-67 (1993).
    • (1993) Planta Med , vol.59 , pp. 63-67
    • Martin, M.L.1
  • 7
    • 0032146194 scopus 로고    scopus 로고
    • Central depressant effects of reticuline extracted from Ocotea duckei in rats and mice
    • Morais, L.C., Barbosa-Filho, J.M. & Almeida, R.N. Central depressant effects of reticuline extracted from Ocotea duckei in rats and mice. J. Ethnopharmacol. 62, 57-61 (1998).
    • (1998) J. Ethnopharmacol , vol.62 , pp. 57-61
    • Morais, L.C.1    Barbosa-Filho, J.M.2    Almeida, R.N.3
  • 8
    • 0030913319 scopus 로고    scopus 로고
    • Norreticuline and reticuline as possible new agents for hair growth acceleration
    • Nakaoji, K., Nayeshiro, H. & Tanahashi, T. Norreticuline and reticuline as possible new agents for hair growth acceleration. Biol. Pharm. Bull. 20, 586-588 (1997).
    • (1997) Biol. Pharm. Bull , vol.20 , pp. 586-588
    • Nakaoji, K.1    Nayeshiro, H.2    Tanahashi, T.3
  • 9
    • 33746310059 scopus 로고    scopus 로고
    • Apoptotic response of uveal melanoma cells upon treatment with chelidonine, sanguinarine and chelerythrine
    • Kemeny-Beke, A. et al. Apoptotic response of uveal melanoma cells upon treatment with chelidonine, sanguinarine and chelerythrine. Cancer Lett. 237, 67-75 (2006).
    • (2006) Cancer Lett , vol.237 , pp. 67-75
    • Kemeny-Beke, A.1
  • 10
    • 0028938214 scopus 로고
    • Structure-antioxidative activity relationships in benzylisoquinoline alkaloids
    • Cassels, B.K. et al. Structure-antioxidative activity relationships in benzylisoquinoline alkaloids. Pharmacol. Res. 31, 103-107 (1995).
    • (1995) Pharmacol. Res , vol.31 , pp. 103-107
    • Cassels, B.K.1
  • 11
    • 30644458311 scopus 로고    scopus 로고
    • Evaluation of benzyltetrahydroisoquinolines as ligands for neuronal nicotinic acetylcholine receptors
    • Exley, R. et al. Evaluation of benzyltetrahydroisoquinolines as ligands for neuronal nicotinic acetylcholine receptors. Br. J. Pharmacol. 146, 15-24 (2005).
    • (2005) Br. J. Pharmacol , vol.146 , pp. 15-24
    • Exley, R.1
  • 12
    • 20844441926 scopus 로고    scopus 로고
    • Anti-HIV benzylisoquinoline alkaloids and flavonoids from the leaves of Nelumbo nucifera, and structure-activity correlations with related alkaloids
    • Kashiwada, Y. et al. Anti-HIV benzylisoquinoline alkaloids and flavonoids from the leaves of Nelumbo nucifera, and structure-activity correlations with related alkaloids. Bioorg. Med. Chem. 13, 443-448 (2005).
    • (2005) Bioorg. Med. Chem , vol.13 , pp. 443-448
    • Kashiwada, Y.1
  • 13
    • 0036901923 scopus 로고    scopus 로고
    • Immunomodulatory effects and mechanisms of plant alkaloid tetrandrine in autoimmune diseases
    • Lai, J.H. Immunomodulatory effects and mechanisms of plant alkaloid tetrandrine in autoimmune diseases. Acta Pharmacol. Sin. 23, 1093-1101 (2002).
    • (2002) Acta Pharmacol. Sin , vol.23 , pp. 1093-1101
    • Lai, J.H.1
  • 14
    • 0036902138 scopus 로고    scopus 로고
    • Tetrandrine and related bis-benzylisoquinoline alkaloids from medicinal herbs: Cardiovascular effects and mechanisms of action
    • Kwan, C.Y. & Achike, F.I. Tetrandrine and related bis-benzylisoquinoline alkaloids from medicinal herbs: cardiovascular effects and mechanisms of action. Acta Pharmacol. Sin. 23, 1057-1068 (2002).
    • (2002) Acta Pharmacol. Sin , vol.23 , pp. 1057-1068
    • Kwan, C.Y.1    Achike, F.I.2
  • 15
    • 0030882744 scopus 로고    scopus 로고
    • Relationships between structure and vascular activity in a series of benzylisoquinolines
    • Chulia, S. et al. Relationships between structure and vascular activity in a series of benzylisoquinolines. Br. J. Pharmacol. 122, 409-416 (1997).
    • (1997) Br. J. Pharmacol , vol.122 , pp. 409-416
    • Chulia, S.1
  • 16
    • 33744954743 scopus 로고    scopus 로고
    • β-Phenylethylamines and the isoquinoline alkaloids
    • Bentley, K.W. β-Phenylethylamines and the isoquinoline alkaloids. Nat. Prod. Rep. 23, 444-463 (2006).
    • (2006) Nat. Prod. Rep , vol.23 , pp. 444-463
    • Bentley, K.W.1
  • 17
    • 0035780976 scopus 로고    scopus 로고
    • Alkaloid biosynthesis in plants: Biochemistry, cell biology, molecular regulation, and metabolic engineering applications
    • Facchini, P.J. Alkaloid biosynthesis in plants: biochemistry, cell biology, molecular regulation, and metabolic engineering applications. Annu. Rev. Plant Physiol. Plant Mol. Biol. 52, 29-66 (2001).
    • (2001) Annu. Rev. Plant Physiol. Plant Mol. Biol , vol.52 , pp. 29-66
    • Facchini, P.J.1
  • 18
    • 34548313705 scopus 로고    scopus 로고
    • Metabolic engineering in isoquinoline alkaloid biosynthesis
    • Sato, F., Inui, T. & Takemura, T. Metabolic engineering in isoquinoline alkaloid biosynthesis. Curr. Pharm. Biotechnol. 8, 211-218 (2007).
    • (2007) Curr. Pharm. Biotechnol , vol.8 , pp. 211-218
    • Sato, F.1    Inui, T.2    Takemura, T.3
  • 19
    • 36849084099 scopus 로고    scopus 로고
    • Metabolic engineering of morphinan alkaloids by over-expression and RNAi suppression of salutaridinol 7-O-acetyltransferase in opium poppy
    • Allen, R.S. et al. Metabolic engineering of morphinan alkaloids by over-expression and RNAi suppression of salutaridinol 7-O-acetyltransferase in opium poppy. Plant Biotechnol. J. 6, 22-30 (2008).
    • (2008) Plant Biotechnol. J , vol.6 , pp. 22-30
    • Allen, R.S.1
  • 20
    • 11144352099 scopus 로고    scopus 로고
    • RNAi-mediated replacement of morphine with the nonnarcotic alkaloid reticuline in opium poppy
    • Allen, R.S. et al. RNAi-mediated replacement of morphine with the nonnarcotic alkaloid reticuline in opium poppy. Nat. Biotechnol. 22, 1559-1566 (2004).
    • (2004) Nat. Biotechnol , vol.22 , pp. 1559-1566
    • Allen, R.S.1
  • 21
    • 0035793046 scopus 로고    scopus 로고
    • Metabolic engineering of plant alkaloid biosynthesis
    • Sato, F. et al. Metabolic engineering of plant alkaloid biosynthesis. Proc. Natl. Acad. Sci. USA 98, 367-372 (2001).
    • (2001) Proc. Natl. Acad. Sci. USA , vol.98 , pp. 367-372
    • Sato, F.1
  • 22
    • 33947217953 scopus 로고    scopus 로고
    • Gene transcript and metabolite profiling of elicitor-induced opium poppy cell cultures reveals the coordinate regulation of primary and secondary metabolism
    • Zulak, K.G. et al. Gene transcript and metabolite profiling of elicitor-induced opium poppy cell cultures reveals the coordinate regulation of primary and secondary metabolism. Planta 225, 1085-1106 (2007).
    • (2007) Planta , vol.225 , pp. 1085-1106
    • Zulak, K.G.1
  • 23
    • 44949247292 scopus 로고    scopus 로고
    • Microbial production of plant benzylisoquinoline alkaloids
    • Minami, H. et al. Microbial production of plant benzylisoquinoline alkaloids. Proc. Natl. Acad. Sci. USA 105, 7393-7398 (2008).
    • (2008) Proc. Natl. Acad. Sci. USA , vol.105 , pp. 7393-7398
    • Minami, H.1
  • 24
    • 33749241876 scopus 로고    scopus 로고
    • Comparative transcript and alkaloid profiling in Papaver species identifies a short chain dehydrogenase/reductase involved in morphine biosynthesis
    • Ziegler, J. et al. Comparative transcript and alkaloid profiling in Papaver species identifies a short chain dehydrogenase/reductase involved in morphine biosynthesis. Plant J. 48, 177-192 (2006).
    • (2006) Plant J , vol.48 , pp. 177-192
    • Ziegler, J.1
  • 25
    • 0028086426 scopus 로고
    • Purification and characterization of S-adenosyl-L-methionine: Norcoclaurine 6-O-methyltransferase from cultured Coptis japonica cells
    • Sato, F., Tsujita, T., Katagiri, Y., Yoshida, S. & Yamada, Y. Purification and characterization of S-adenosyl-L-methionine: norcoclaurine 6-O-methyltransferase from cultured Coptis japonica cells. Eur. J. Biochem. 225, 125-131 (1994).
    • (1994) Eur. J. Biochem , vol.225 , pp. 125-131
    • Sato, F.1    Tsujita, T.2    Katagiri, Y.3    Yoshida, S.4    Yamada, Y.5
  • 26
    • 0347317979 scopus 로고    scopus 로고
    • (R,S)-Reticuline 7-O-methyltransferase and (R,S)-norcoclaurine 6-O-methyltransferase of Papaver somniferum - cDNA cloning and characterization of methyl transfer enzymes of alkaloid biosynthesis in opium poppy
    • Ounaroon, A., Decker, G., Schmidt, J., Lottspeich, F. & Kutchan, T.M. (R,S)-Reticuline 7-O-methyltransferase and (R,S)-norcoclaurine 6-O-methyltransferase of Papaver somniferum - cDNA cloning and characterization of methyl transfer enzymes of alkaloid biosynthesis in opium poppy. Plant J. 36, 808-819 (2003).
    • (2003) Plant J , vol.36 , pp. 808-819
    • Ounaroon, A.1    Decker, G.2    Schmidt, J.3    Lottspeich, F.4    Kutchan, T.M.5
  • 27
    • 33744955253 scopus 로고    scopus 로고
    • The regulatory roles of the galactose permease and kinase in the induction response of the GAL network in Saccharomyces cerevisiae
    • Hawkins, K.M. & Smolke, C.D. The regulatory roles of the galactose permease and kinase in the induction response of the GAL network in Saccharomyces cerevisiae. J. Biol. Chem. 281, 13485-13492 (2006).
    • (2006) J. Biol. Chem , vol.281 , pp. 13485-13492
    • Hawkins, K.M.1    Smolke, C.D.2
  • 28
    • 33747376106 scopus 로고    scopus 로고
    • Engineering of promoter replacement cassettes for fine-tuning of gene expression in Saccharomyces cerevisiae
    • Nevoigt, E. et al. Engineering of promoter replacement cassettes for fine-tuning of gene expression in Saccharomyces cerevisiae. Appl. Environ. Microbiol. 72, 5266-5273 (2006).
    • (2006) Appl. Environ. Microbiol , vol.72 , pp. 5266-5273
    • Nevoigt, E.1
  • 29
    • 0028785275 scopus 로고
    • Characterization and mechanism of the berberine bridge enzyme, a covalently flavinylated oxidase of benzophenanthridine alkaloid biosynthesis in plants
    • Kutchan, T.M. & Dittrich, H. Characterization and mechanism of the berberine bridge enzyme, a covalently flavinylated oxidase of benzophenanthridine alkaloid biosynthesis in plants. J. Biol. Chem. 270, 24475-24481 (1995).
    • (1995) J. Biol. Chem , vol.270 , pp. 24475-24481
    • Kutchan, T.M.1    Dittrich, H.2
  • 30
    • 0034778031 scopus 로고    scopus 로고
    • Berberine bridge enzyme, a key branch-point enzyme in benzylisoquinoline alkaloid biosynthesis, contains a vacuolar sorting determinant
    • Bird, D.A. & Facchini, P.J. Berberine bridge enzyme, a key branch-point enzyme in benzylisoquinoline alkaloid biosynthesis, contains a vacuolar sorting determinant. Planta 213, 888-897 (2001).
    • (2001) Planta , vol.213 , pp. 888-897
    • Bird, D.A.1    Facchini, P.J.2
  • 31
    • 0141755310 scopus 로고    scopus 로고
    • Molecular cloning and characterization of CYP719, a methylenedioxy bridge-forming enzyme that belongs to a novel P450 family, from cultured Coptis japonica cells
    • Ikezawa, N. et al. Molecular cloning and characterization of CYP719, a methylenedioxy bridge-forming enzyme that belongs to a novel P450 family, from cultured Coptis japonica cells. J. Biol. Chem. 278, 38557-38565 (2003).
    • (2003) J. Biol. Chem , vol.278 , pp. 38557-38565
    • Ikezawa, N.1
  • 32
    • 2142751582 scopus 로고    scopus 로고
    • 1,2-Dehydroreticuline synthase, the branch point enzyme opening the morphinan biosynthetic pathway
    • Hirata, K., Poeaknapo, C., Schmidt, J. & Zenk, M.H. 1,2-Dehydroreticuline synthase, the branch point enzyme opening the morphinan biosynthetic pathway. Phytochemistry 65, 1039-1046 (2004).
    • (2004) Phytochemistry , vol.65 , pp. 1039-1046
    • Hirata, K.1    Poeaknapo, C.2    Schmidt, J.3    Zenk, M.H.4
  • 33
    • 28244474541 scopus 로고    scopus 로고
    • Human white blood cells synthesize morphine: CYP2D6 modulation
    • Zhu, W., Cadet, P., Baggerman, G., Mantione, K.J. & Stefano, G.B. Human white blood cells synthesize morphine: CYP2D6 modulation. J. Immunol. 175, 7357-7362 (2005).
    • (2005) J. Immunol , vol.175 , pp. 7357-7362
    • Zhu, W.1    Cadet, P.2    Baggerman, G.3    Mantione, K.J.4    Stefano, G.B.5
  • 34
    • 42249097714 scopus 로고    scopus 로고
    • Evolutionary and cellular webs in benzylisoquinoline alkaloid biosynthesis
    • Liscombe, D.K. & Facchini, P.J. Evolutionary and cellular webs in benzylisoquinoline alkaloid biosynthesis. Curr. Opin. Biotechnol. 19, 173-180 (2008).
    • (2008) Curr. Opin. Biotechnol , vol.19 , pp. 173-180
    • Liscombe, D.K.1    Facchini, P.J.2
  • 35
    • 3242655621 scopus 로고    scopus 로고
    • Metabolic channeling in plants
    • Winkel, B.S. Metabolic channeling in plants. Annu. Rev. Plant Biol. 55, 85-107 (2004).
    • (2004) Annu. Rev. Plant Biol , vol.55 , pp. 85-107
    • Winkel, B.S.1
  • 36
    • 0004262043 scopus 로고    scopus 로고
    • 3rd edn, Cold Spring Harbor Laboratory Press, Cold Spring Harbor, New York, USA
    • Sambrook, J. & Russell, D.W. Molecular Cloning 3rd edn. (Cold Spring Harbor Laboratory Press, Cold Spring Harbor, New York, USA, 2001).
    • (2001) Molecular Cloning
    • Sambrook, J.1    Russell, D.W.2
  • 37
    • 0028977906 scopus 로고
    • Expression of cytochrome P450 2D6 in Escherichia coli, purification, and spectral and catalytic characterization
    • Gillam, E.M., Guo, Z., Martin, M.V., Jenkins, C.M. & Guengerich, F.P. Expression of cytochrome P450 2D6 in Escherichia coli, purification, and spectral and catalytic characterization. Arch. Biochem. Biophys. 319, 540-550 (1995).
    • (1995) Arch. Biochem. Biophys , vol.319 , pp. 540-550
    • Gillam, E.M.1    Guo, Z.2    Martin, M.V.3    Jenkins, C.M.4    Guengerich, F.P.5
  • 38
    • 0030852872 scopus 로고    scopus 로고
    • Cloning, yeast expression, and characterization of the coupling of two distantly related Arabidopsis thaliana NADPH-cytochrome P450 reductases with P450 CYP73A5
    • Urban, P., Mignotte, C., Kazmaier, M., Delorme, F. & Pompon, D. Cloning, yeast expression, and characterization of the coupling of two distantly related Arabidopsis thaliana NADPH-cytochrome P450 reductases with P450 CYP73A5. J. Biol. Chem. 272, 19176-19186 (1997).
    • (1997) J. Biol. Chem , vol.272 , pp. 19176-19186
    • Urban, P.1    Mignotte, C.2    Kazmaier, M.3    Delorme, F.4    Pompon, D.5
  • 39
    • 0027158167 scopus 로고
    • Mammalian PC-12 cell genetically engineered for human cytochrome P450 2E1 expression
    • Mapoles, J., Berthou, F., Alexander, A., Simon, F. & Menez, J.F. Mammalian PC-12 cell genetically engineered for human cytochrome P450 2E1 expression. Eur. J. Biochem. 214, 735-745 (1993).
    • (1993) Eur. J. Biochem , vol.214 , pp. 735-745
    • Mapoles, J.1    Berthou, F.2    Alexander, A.3    Simon, F.4    Menez, J.F.5
  • 40
    • 33644792045 scopus 로고    scopus 로고
    • Yeast transformation by the LiAc/SS Carrier DNA/PEG method
    • Gietz, R.D. & Woods, R.A. Yeast transformation by the LiAc/SS Carrier DNA/PEG method. Methods Mol. Biol. 313, 107-120 (2006).
    • (2006) Methods Mol. Biol , vol.313 , pp. 107-120
    • Gietz, R.D.1    Woods, R.A.2
  • 41
    • 0024977417 scopus 로고
    • Elevated recombination rates in transcriptionally active DNA
    • Thomas, B.J. & Rothstein, R. Elevated recombination rates in transcriptionally active DNA. Cell 56, 619-630 (1989).
    • (1989) Cell , vol.56 , pp. 619-630
    • Thomas, B.J.1    Rothstein, R.2
  • 42
    • 0029994841 scopus 로고    scopus 로고
    • A new efficient gene disruption cassette for repeated use in budding yeast
    • Guldener, U., Heck, S., Fielder, T., Beinhauer, J. & Hegemann, J.H. A new efficient gene disruption cassette for repeated use in budding yeast. Nucleic Acids Res. 24, 2519-2524 (1996).
    • (1996) Nucleic Acids Res , vol.24 , pp. 2519-2524
    • Guldener, U.1    Heck, S.2    Fielder, T.3    Beinhauer, J.4    Hegemann, J.H.5
  • 43
    • 44649092127 scopus 로고    scopus 로고
    • Analysis of major alkaloids in Rhizoma coptidis by capillary electrophoresis-electrospray-time of flight mass spectrometry with different background electrolytes
    • Chen, J. et al. Analysis of major alkaloids in Rhizoma coptidis by capillary electrophoresis-electrospray-time of flight mass spectrometry with different background electrolytes. Electrophoresis 29, 2135-2147 (2008).
    • (2008) Electrophoresis , vol.29 , pp. 2135-2147
    • Chen, J.1
  • 44
    • 0142257918 scopus 로고    scopus 로고
    • Electrospray tandem mass spectrometric investigations of morphinans
    • Raith, K. et al. Electrospray tandem mass spectrometric investigations of morphinans. J. Am. Soc. Mass Spectrom. 14, 1262-1269 (2003).
    • (2003) J. Am. Soc. Mass Spectrom , vol.14 , pp. 1262-1269
    • Raith, K.1


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.