Metabolic engineering and synthetic biology for the production of isoquinoline alkaloids

Biotechnology for Medicinal Plants: Micropropagation and Improvement

Volumn 9783642299742, Issue , 2013, Pages 327-343

  Chow, Yit Lai ^a   Sato, Fumihiko ^a  

^a KYOTO UNIVERSITY   (Japan)

Author keywords

[No Author keywords available]

Indexed keywords

METABOLIC ENGINEERING; METABOLISM; METABOLITES; PLANTS (BOTANY);

DRUG DEVELOPMENT; ISOQUINOLINES; LARGE-SCALES; LOW-YIELD; MOLECULAR LEVELS; PLANT ALKALOIDS; PLANT TISSUES; SECONDARY METABOLITES; SYNTHETIC BIOLOGY; SYNTHETIC CHEMISTRY;

ALKALOIDS;

EID: 84949177207     PISSN: None     EISSN: None     Source Type: Book    
DOI: 10.1007/978-3-642-29974-2_14     Document Type: Chapter

References (76)

1. Ajikumar PK, Xiao W-H, Tyo KEJ, Wang Y, Simeon F, Leonard E, Mucha O, Phon TH, Pfeifer B, Stephanopoulos G (2010) Isoprenoid pathway optimization for taxol precursor overproduction in Escherichia coli. Science 330:70-74
2. Allen RS, Millgate AG, Chitty JA, Thistleton J, Miller JAC, Fist AJ, Gerlach WL, Larkin PJ (2004) RNAi-mediated replacement of morphine with the non narcotic alkaloid reticuline in opium poppy. Nat Biotechnol 22:1559-1566
3. Allen RS, Miller JAC, Chitty JA, Fist AJ, Gerlach WL, Larkin PJ (2008) Metabolic engineering of morphinan alkaloids by overexpression and RNAi suppression of salutaridinol 7-Oacetyltransferase in opium poppy. Plant Biotechnol J 6:22-30
4. Alper H, Moxley J, Nevoigt E, Fink GR, Stephanopoulos G (2006) Engineering yeast transcription machinery for improved ethanol tolerance and production. Science 314: 1565-1568
5. Apuya NR, Park JH, Zhang L, Ahyow M, Davidow P, Van Fleet J et al (2008) Enhancement of alkaloid production in opium and California poppy by transactivation using heterologous regulatory factors. Plant Biotechnol J 6(2):160-175
6. Bayer T (2010) Transforming biosynthesis into an information science. Nat Chem Biol 6:859-861
7. Borgio J (2009) RNA interference (RNAi) technology: a promising tool for medicinal plant research. J Med Plant Res 3:1176-1183
8. Bungard C, Morris J (2006) Total synthesis of the 7, 30-linked naphthylisoquinoline alkaloid ancistrocladidine. J Org Chem 71(19):7354-7363
9. Cheong BE, Takemura T, Yoshimatsu K, Sato F (2011) Molecular cloning of an Omethyltransferase from adventitious roots of Carapichea ipecacuanha. Biosci Biotechnol Biochem 75(1):107-113
10. Choi KB, Morishige T, Shitan N, Yazaki K, Sato F (2002) Molecular cloning and characterization of coclaurine N-methyltransferase from cultured cells of Coptis japonica. J Biol Chem 277:830-835
11. Croteau R, Kutchan TM, Lewis NG (2000) Natural products (Secondary metabolites). In: Buchanan BB, Gruissem W, Jones RL (eds) Biochemistry and molecular biology of plants. American Society of Plant Physiologists, Maryland
12. Desgagné-Penix I, Khan MF, Schriemer DC, Cram D, Nowak J, Facchini PJ (2010) Integration of deep transcriptome and proteome analyses reveals the components of alkaloid metabolism in opium poppyopium poppy cell cultures. BMC Plant Biol 10:252-268
13. Dittrich H, Kutchan TM (1991) Molecular cloning, expression, and induction of berberine bridge enzyme, an enzyme essential to the formation of benzophenanthridine alkaloids in the response of plants to pathogenic attack. Proc Natl Acad Sci U S A 88:9969-9973
14. Dubouzet JG, Morishige T, Fujii N, An CI, Fukusaki E, Ifuku K et al (2005) Transient RNA silencing of scoulerine 9-O-methyltransferase expression by double stranded RNA in Coptis japonica protoplasts. Biosci Biotechnol Biochem 69:63-70
15. Endo T, Ishida S, Ishikawa N, Sato F (2008) Chloroplastic NAD(P)H dehydrogenase complex and cyclic electron transport around photosystem I. Mol Cells 25(2):1-6
16. Freedonia Group (2009) Study #2565, World Nutraceutical Ingredients Industry Study with Forecasts for 2012 & 2018. The Freedonia Group, USA. http://www.freedoniagroup.com/brochure/25xx/2565smwe.pdf
17. Fujii N, Inui T, Iwasa K, Morishige T, Sato F (2007) Knockdown of berberine bridge enzyme by RNAi accumulates (S)-reticuline and activates a silent pathway in cultured California poppy cells. Transgenic Res 16:363-375
18. Fujita Y (1988/2007) Industrial production of shikonin and berberine, in Ciba Foundation Symposium 137. In: Bock G, Marsh J (eds) Applications of plant cell and tissue culture (Ciba Foundation Symposium 137), Wiley, Chichester, pp 228-238
19. Gaich T, Baran P (2010) Aiming for the ideal synthesis. J Org Chem 75:4657-4673
20. Gesell A, Rolf M, Ziegler J, Luisa Díaz Chávez ML, Huang F-C, Kutchan TM (2009) CYP719B1 is salutaridine synthase, the C-C phenol-coupling enzyme of morphine biosynthesis in opium poppy. J Biol Chem 284:24432-24442
21. Gesell A, Díaz Chávez ML, Kramell R, Piotrowski M, Macheroux P, Kutchan TM (2011) Heterologous expression of two FAD-dependent oxidases with (S)-tetrahydroprotoberberine oxidase activity from Argemone mexicana and Berberis wilsoniae in insect cells. Planta 233:1185-1197
22. Grothe T, Lenz R, Kutchan TM (2001) Molecular characterization of the salutaridinol-7-Oacetyltransferase involved in morphine biosynthesis in opium poppy Papaver somniferum. J Biol Chem 276:30717-30723
23. Hagel JM, Facchini PJ (2010) Dioxygenases catalyze the O-demethylation steps of morphine biosynthesis in opium poppy. Nat Chem Biol 6(4):273-275
24. Hartenfeller M, Schneider G (2011) De novo drug design. Methods Mol Biol 672:299-323
25. Hartmann T (2004) Plant-derived secondary metabolites as defensive chemicals in herbivorous insects: a case study in chemical ecology. Planta 219:1-4
26. Hawkins K, Smolke C (2008) Production of benzylisoquinoline alkaloids in Saccharomyces cerevisiae. Nat Chem Biol 4:564-573
27. Hendrickson J (1975) Systematic synthesis design. IV. Numerical codification of construction reactions. J Am Chem Soc 97(20):5784-5800
28. Ikezawa N, Tanaka M, Nagayoshi M, Shinkyo R, Sakaki T, Inouye K, Sato F (2003) 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
29. Ikezawa N, Iwasa K, Sato F (2007) Molecular cloning and characterization of methylenedioxy bridge-forming enzymes involved in stylopine biosynthesis in Eschscholzia californica. FEBS J 274:1019-1035
30. Ikezawa N, Iwasa K, Sato F (2008) Molecular cloning and characterization of CYP80G2, a cytochrome P450 that catalyzes an intramolecular C-C phenol coupling of (S)-reticuline in magnoflorine biosynthesis, from cultured Coptis japonica cells. J Biol Chem 283:8810-8821
31. Ikezawa N, Iwasa K, Sato F (2009) CYP719A subfamily of cytochrome p450 oxygenase and isoquinoline alkaloid biosynthesis in Eschscholzia californica. Plant Cell Rep 28(1):123-133
32. Inui T, Tamura K, Fujii N, Morishige T, Sato F (2007) Overexpression of Coptis japonica norcoclaurine 6-O-methyltransferase overcomes the rate-limiting step in benzylisoquinoline alkaloid biosynthesis in cultured Eschscholzia californica. Plant Cell Physiol 48:252-262
33. Itoh T, Miyazaki M, Fukuoka H, Nagata K, Ohsawa A (2006) Formal total synthesis of (-)-emetine using catalytic asymmetric allylation of cyclic imines as a key step. Org Lett 8: 1295-1297
34. Kato N, Dubouzet E, Kokabu Y, Yoshida S, Taniguchi Y, Dubouzet JG et al (2007) Identification of a WRKY protein as a transcriptional regulator of benzylisoquinoline alkaloid biosynthesis in Coptis japonica. Plant Cell Physiol 48:8-18
35. Katsumoto Y, Fukuchi-Mizutani M, Fukui Y, Brugliera F, Holton TA, Karan M et al (2007) Engineering of the rose flavonoid biosynthetic pathway successfully generated blue-hued flowers accumulating delphinidin. Plant Cell Physiol 48:1589-1600
36. Kim Y, Wyslouzil B, Weathers P (2002) Secondary metabolism of hairy root cultures in bioreactors. In Vitro Cell Dev Biol Plant 38:1-10
37. Korkina L, Kostyuk V (2012) Biotechnologically produced secondary plant metabolites for cancer treatment and prevention. Curr Pharm Biotechnol 13:265-275
38. Kraus PF, Kutchan TM (1995) Molecular-cloning and heterologous expression of a cDNAencoding berbamunine synthase, a C-O-phenol-coupling cytochrome-P450 from the higherplant Berberis stolonifera. Proc Natl Acad Sci U S A 92(6):2071-2075
39. Le Flem-Bonhomme V, Laurain-Mattar D, Fliniaux MA (2004) Hairy root induction of Papaver somniferum var. album, a difficult-to-transform plant, by A. rhizogenes LBA 9402. Planta 218(5):890-893
40. Lee EJ, Facchini P (2010) Norcoclauine synthase is a member of the pathogenesis-related 10/Bet v1 protein family. Plant Cell 22:3489-3503
41. Lee E-K, Jin Y-W, Park JH, Yoo YM, Hong SM, Amir R et al (2010) Cultured cambial meristematic cells as a source of plant natural products. Nat Biotechnol 28:1213-1217
42. Leonard E, Runguphan W, O'Connor S, Prather KJ (2009) Opportunities in metabolic engineering to facilitate scalable alkaloid production. Nat Chem Biol 5:291-300
43. Lv P, Huang K, Xie L, Xu X (2011) Palladium-catalyzed tandem reaction to construct benzo[c]phenanthridine: application to the total synthesis of benzo[c]phenanthridine alkaloids. Org Biomol Chem 9:3133-3135
44. Minami H, Dubouzet E, Iwasa K, Sato F (2007) Functional analysis of norcoclaurine synthase in Coptis japonica. J Biol Chem 282(9):6274-6282
45. Minami H, Kim J-S, Ikezawa N, Takemura T, Katayama T, Kumagai H, Sato F (2008) Microbial production of plant benzylisoquinoline alkaloids. Proc Natl Acad Sci U S A 105:7393-7398
46. Morishige T, Tsujita T, Yamada Y, Sato F (2000) Molecular characterization of the S-Adenosyl-Lmethionine: 30-hydroxy-N-methylcoclaurine 40-O-methyltransferase involved in isoquinoline alkaloid biosynthesis in Coptis japonica. J Biol Chem 275:23398-23405
47. Nakagawa A, Minami H, Kim JS, Koyanagi T, Katayama T, Sato F, Kumagai H (2011) A bacterial platform for fermentative production of plant alkaloids. Nat Commun 2, Article number: 326
48. Newman D, Cragg G (2007) Natural products as sources of new drugs over the last 25 years. J Nat Prod 70:461-477
49. Nomura T, Kutchan TM (2010) Three new O-methyltransferases are sufficient for all Omethylation reactions of Ipecac alkaloid biosynthesis in root culture of Psychotria ipecacuanha. J Biol Chem 285:7722-7738
50. Park S, Yu M, Facchini P (2002) Antisense RNA-mediated suppression of benzophenanthridine alkaloid biosynthesis in transgenic cell cultures of California poppy. Plant Physiol 128:696-706
51. Park S, Yu M, Facchini P (2003) Modulation of berberine bridge enzyme levels in transgenic root cultures of California poppy alters the accumulation of benzophenanthridine alkaloids. Plant Mol Biol 51(2):153-164
52. Pauli H, Kutchan TM (1998) Molecular cloning and functional heterologous expression of two alleles encoding (S)-N-methylcoclaurine 30-hydroxylase (CYP80B1), a new methyl jasmonate-inducible cytochrome P-450-dependent mono-oxygenase of benzylisoquinoline alkaloid biosynthesis. Plant J 13:793-801
53. Ro DK, Paradise EM, Ouellet M, Fisher KJ, Newman KL, Ndungu JM et al (2006) Production of the antimalarial drug precursor artemisinic acid in engineered yeast. Nature 440:940-943
54. Samanani N, Liscombe DK, Facchini PJ (2004) Molecular cloning and characterization of norcoclaurine synthase, an enzyme catalyzing the first committed step in benzylisoquinoline alkaloid biosynthesis. Plant J 40:302-313
55. Sato F (2005) RNAi and functional genomics. Plant Biotech 22:431-442
56. Sato F, Yamada Y (2008) Engineering formation of medicinal compounds in cell cultures. In: Bohnert HJ, Nguyen H, Lewis NG (eds) Advances in plant biochemistry and molecular biology, vol 1. Elsevier Ltd., Amsterdam, pp 311-345
57. Sato F, Hashimoto T, Hachiya A, Tamura K-i, Choi K-B, Morishige T, Fumimoto H, Yamada Y (2001) Metabolic engineering of plant alkaloid biosynthesis. Proc Natl Acad Sci U S A 98:367-372
58. Sato F, Inai K, Hashimoto T (2007a) Metabolic engineering in alkaloid biosynthesis: case study in tyrosine- and putrescine-derived alkaloids. In: Verpoorte R et al (eds) Applications of plant metabolic engineering. Springer, The Netherlands
59. Sato F, Inui T, Takemura T (2007b) Metabolic engineering in isoquinoline alkaloid biosynthesis. Curr Pharm Biotechnol 8:211-218
60. Shanks J, Morgan J (1999) Plant 'hairy root' culture. Curr Opin Biotechnol 10:151-155
61. Singla D, Sharma A, Kaur J, Panwar B, Raghava GP (2010) BIAdb: a curated database of benzylisoquinoline alkaloids. BMC Pharmacol 10:4
62. Takemura T, Ikezawa N, Iwasa K, Sato F (2010) Metabolic diversification of benzylisoquinoline alkaloid biosynthesis through the introduction of a branch pathway in Eschscholzia californica. Plant Cell Physiol 51:949-959
63. Takemura T, Ikezawa N, Iwasa K, Sato F (2012) Molecular cloning and characterization of a cytochrome P450 in sanguinarine biosynthesis from Eschscholzia californica cells. Phytochem doi:10.1016/j.phytochem.2012.02.013
64. Takeshita N, Fujiwara H, Mimura H, Fitchen J, Yamada Y, Sato F (1995) Molecular cloning and characterization of S-Adenosyl-L-methionine: scoulerine-9-O-methyltransferase from cultured cells of Coptis japonica. Plant Cell Physiol 36:29-36
65. Tietze L, Rackelmann N, Sekar G (2003) Catalyst-controlled stereoselective combinatorial synthesis. Angew Chem Int Ed 42:4254-4257
66. Unterlinner B, Lenz R, Kutchan TM (1999) Molecular cloning and functional expression of codeinone reductase: the penultimate enzyme in morphine biosynthesis in the opium poppy Papaver somniferum. Plant J 18(5):465-475
67. Veerasham C (2004) Medicinal plant biotechnology. CBS, New Delhi, pp 377-419
68. Verpoorte R, Van Der Heijden R, Van Gulik WM, Ten Hoopen HJG (1991) Plant biotechnology for the production of alkaloids: present status and prospects. In: Brossi A (ed) The Alkaloids: chemistry and pharmacology, vol 40. Academic, New York, pp 1-187
69. Vogel M, Lawson M, Sippl W, Conarad U, Roos W (2010) Structure and mechanism of sanguinarine reductase, an enzyme of alkaloid detoxification. J Biol Chem 285:18397-18406
70. Yamada Y, Kokabu Y, Chaki K, Yoshimoto T, Ohgaki M, Yoshida S, Kato N, Koyama T, Sato F (2011) Isoquinoline alkaloid biosynthesis is regulated by a unique bHLH-type transcription factor in Coptis japonica. Plant Cell Physiol 52:1131-1141
71. Yukimune Y, Tabata H, Higashi Y, Hara Y (1996) Methyl jasmonate-induced overproduction of paclitaxel and baccatin III in taxus cell suspension cultures. Nat Biotechnol 14:1129-1132
72. Zhang L, Yang B, Lu BB, Kai GY, Wang ZN, Xia Y et al (2007) Tropane alkaloids production in transgenic Hyoscyamus niger hairy root cultures over-expressing putrescine N-methyltransferase is methyl jasmonate-dependent. Planta 225:887-896
73. Zhang L, Jing F, Li F, Li M, Wang Y, Wang G, Sun X, Tang K (2009) Development of transgenic Artemisia annua (Chinese wormwood) plants with an enhanced content of artemisinin, an effective antimalarial drug, by hairpin-RNA mediated gene silencing. Biotechnol Appl Biochem 52:199-207
74. Zhou M, Zhu ZM, Shao JR, Tang YX, Wu YM (2011) Production and metabolic engineering of bioactive substances in plant hairy root culture. Appl Microbiol Biotechnol 90:1229-1239
75. Zhou M, Shao JR, Tang YX (2010) Transcriptional response of the catharanthine biosynthesis pathway to methyl jasmonate/nitric oxide elicitation in Catharanthus roseus hairy root culture. Appl Microbiol Biotechnol 88:737-750
76. Zhou M, Shao J, Tang Y (2009) Production and metabolic engineering of terpenoid indole alkaloids in cell cultures of the medicinal plant Catharanthus roseus (L) G. Don (Madagascar periwinkle). Biotechnol Appl Biochem 52:313-323