Heterologous production of curcuminoids

Microbiology and Molecular Biology Reviews

Volumn 79, Issue 1, 2015, Pages 39-60

  Rodrigues, J L ^a,c,d   Prather, K L J ^b,c,d   Kluskens, L D ^a   Rodrigues, L R ^a,c,d  

^a UNIVERSITY OF MINHO   (Portugal)

^b Massachusetts Institute of Technology   (United States)

^c MASSACHUSETTS INSTITUTE OF TECHNOLOGY   (United States)

^d NONE   (Portugal)

Author keywords

[No Author keywords available]

Indexed keywords

ACYL COENZYME A; CAFFEIC ACID; CARBOXYLIC ACID; CURCUMINOID; FERULIC ACID; HERBACEOUS AGENT; MALONYL COENZYME A; PHENYLALANINE; POLYKETIDE SYNTHASE; TURMERIC; TYROSINE; UNCLASSIFIED DRUG; CURCUMIN; POLYKETIDE;

ANTIINFLAMMATORY ACTIVITY; ANTINEOPLASTIC ACTIVITY; ANTIOXIDANT ACTIVITY; BIOAVAILABILITY; BIOSYNTHESIS; CURCUMA LONGA; DRUG MANUFACTURE; ESCHERICHIA COLI; HOST; KINETICS; METABOLIC ENGINEERING; MINERAL SUPPLEMENTATION; NONHUMAN; REVIEW; SACCHAROMYCES CEREVISIAE; ANALOGS AND DERIVATIVES; CHEMISTRY; CURCUMA; GENETICS; METABOLISM;

CURCUMA LONGA; ESCHERICHIA COLI;

BIOLOGICAL AVAILABILITY; BIOSYNTHETIC PATHWAYS; CARBOXYLIC ACIDS; CURCUMA; CURCUMIN; ESCHERICHIA COLI; PHENYLALANINE; POLYKETIDES; TYROSINE;

EID: 84925275219     PISSN: 10922172     EISSN: 10985557     Source Type: Journal    
DOI: 10.1128/MMBR.00031-14     Document Type: Review

References (209)

1. Jayaprakasha GK, Jagan Mohan Rao L, Sakariah KK. 2005. Chemistry and biological activities of C. longa. Trends Food Sci Technol 16: 533-548. http://dx.doi.org/10.1016/j.tifs.2005.08.006.
2. Sharma RA, Gescher AJ, Steward WP. 2005. Curcumin: The story so far. Eur J Cancer 41: 1955-1968. http://dx.doi.org/10.1016/j.ejca.2005.05.009.
3. Tayyem RF, Heath DD, Al-Delaimy WK, Rock CL. 2006. Curcumin content of turmeric and curry powders. Nutr Cancer 55: 126-131. http://dx.doi.org/10.1207/s15327914nc5502-2.
4. Srinivasan KR. 1953. A chromatographic study of the curcuminoids in Curcuma longa, L. J Pharm Pharmacol 5: 448-457. http://dx.doi.org/10.1111/j.2042-7158.1953.tb14007.x.
5. Tohda C, Nakayama N, Hatanaka F, Komatsu K. 2006. Comparison of anti-inflammatory activities of six Curcuma rhizomes: A possible curcuminoid-independent pathway mediated by Curcuma phaeocaulis extract. Evid Based Complement Alternat Med 3: 255-260. http://dx.doi.org/10.1093/ecam/nel008.
6. Abas F, Lajis NH, Shaari K, Israf DA, Stanslas J, Yusuf UK, Raof SM. 2005. A labdane diterpene glucoside from the rhizomes of Curcuma mangga. J Nat Prod 68: 1090-1093. http://dx.doi.org/10.1021/np0500171.
7. Malek SNA, Lee GS, Hong SL, Yaacob H, Wahab NA, Faizal Weber J-F, Shah SAA. 2011. Phytochemical and cytotoxic investigations of Curcuma mangga rhizomes. Molecules 16: 4539-4548. http://dx.doi.org/10.3390/molecules16064539.
8. Ruslay S, Abas F, Shaari K, Zainal Z, Sirat H, Israf DA, Lajis NH. 2007. Characterization of the components present in the active fractions of health gingers Curcuma xanthorrhiza and Zingiber zerumbet. by HPLCDAD-ESIMS. Food Chem 104: 1183-1191. http://dx.doi.org/10.1016/j.foodchem.2007.01.067.
9. Uehara S-I, Yasuda I, Akiyama K, Morita H, Takeya K, Itokawa H. 1987. Diarylheptanoids from the rhizomes of Curcuma xanthorrhiza and Alpinia officinarum. Chem Pharm Bull 35: 3298-3304. http://dx.doi.org/10.1248/cpb.35.3298.
10. Syu W-J, Shen C-C, Don M-J, Ou J-C, Lee G-H, Sun C-M. 1998. Cytotoxicity of curcuminoids and some novel compounds from Curcuma zedoaria. J Nat Prod 61: 1531-1534. http://dx.doi.org/10.1021/np980269k.
11. Lobo R, Prabhu KS, Shirwaikar A, Shirwaikar A. 2009. Curcuma zedoaria Rosc. white turmeric): A review of its chemical, pharmacological and ethnomedicinal properties. J Pharm Pharmacol 61: 13-21. http://dx.doi.org/10.1211/jpp/61.01.0003.
12. Mohamad H, Lajis NH, Abas F, Ali AM, Sukari MA, Kikuzaki H, Nakatani N. 2005. Antioxidative constituents of Etlingera elatior. J Nat Prod 68: 285-288. http://dx.doi.org/10.1021/np040098l.
13. Masuda T, Jitoe A. 1994. Antioxidative and antiinflammatory compounds from tropical gingers: Isolation, structure determination, and activities of cassumunins A, B, and C, new complex curcuminoids from Zingiber cassumunar. J Agric Food Chem 42: 1850-1856. http://dx.doi.org/10.1021/jf00045a004.
14. Masuda T, Jitoe A, Mabry TJ. 1995. Isolation and structure determination of cassumunarins A, B, and C: New anti-inflammatory antioxidants from a tropical ginger, Zingiber cassumunar. J Am Oil Chem Soc 72: 1053-1057. http://dx.doi.org/10.1007/BF02660721.
15. Bagchi A. 2012. Extraction of curcumin. J Environ Sci Toxicol Food Technol 1: 1-16.
16. Ravindran P, Babu KN, Sivaraman K. 2007. Turmeric: The genus Curcuma. CRC Press, Boca Raton, FL.
17. Aggarwal BB, Kumar A, Bharti AC. 2003. Anticancer potential of curcumin: Preclinical and clinical studies. Anticancer Res 23: 363-398.
18. Goel A, Kunnumakkara AB, Aggarwal BB. 2008. Curcumin as "cure-cumin": From kitchen to clinic. Biochem Pharmacol 75: 787-809. http://dx.doi.org/10.1016/j.bcp.2007.08.016.
19. Vogel A, Pelletier J. 1815. Examen chimique de la racine de Curcuma. J Pharmacol 1: 289-300.
20. Schraufstätter E, Bernt H. 1949. Antibacterial action of curcumin and related compounds. Nature 164: 456-457. http://dx.doi.org/10.1038/164456a0.
21. Negi P, Jayaprakasha G, Jagan Mohan Rao L, Sakariah K. 1999. Antibacterial activity of turmeric oil: A byproduct from curcumin manufacture. J Agric Food Chem 47: 4297-4300. http://dx.doi.org/10.1021/jf990308d.
22. Kim M-K, Choi G-J, Lee H-S. 2003. Fungicidal property of Curcuma longa L. rhizome-derived curcumin against phytopathogenic fungi in a greenhouse. J Agric Food Chem 51: 1578-1581. http://dx.doi.org/10.1021/jf0210369.
23. Reddy RC, Vatsala PG, Keshamouni VG, Padmanaban G, Rangarajan PN. 2005. Curcumin for malaria therapy. Biochem Biophys Res Commun 326: 472-474. http://dx.doi.org/10.1016/j.bbrc.2004.11.051.
24. Strimpakos AS, Sharma RA. 2008. Curcumin: Preventive and therapeutic properties in laboratory studies and clinical trials. Antioxid Redox Signal 10: 511-546. http://dx.doi.org/10.1089/ars.2007.1769.
25. Shimatsu A, Kakeya H, Imaizumi A, Morimoto T, Kanai M, Maeda S. 2012. Clinical application of "curcumin," a multi-functional substance. Anti-Aging Med 9: 43-51.
26. Liu D, Chen Z. 2013. The effect of curcumin on breast cancer cells. J Breast Cancer 16: 133-137. http://dx.doi.org/10.4048/jbc.2013.16.2.133.
27. Bisht K, Wagner K-H, Bulmer AC. 2010. Curcumin, resveratrol and flavonoids as anti-inflammatory, cyto-And DNA-protective dietary compounds. Toxicology 278: 88-100. http://dx.doi.org/10.1016/j.tox.2009.11.008.
28. Aggarwal BB, Sung B. 2009. Pharmacological basis for the role of curcumin in chronic diseases: An age-old spice with modern targets. Trends Pharmacol Sci 30: 85-94. http://dx.doi.org/10.1016/j.tips.2008.11.002.
29. Prasad S, Gupta SC, Tyagi AK, Aggarwal BB. 2014. Curcumin, a component of golden spice: From bedside to bench and back. Biotechnol Adv 32: 1053-64. http://dx.doi.org/10.1016/j.biotechadv.2014.04.004.
30. Kuttan R, Bhanumathy P, Nirmala K, George MC. 1985. Potential anticancer activity of turmeric Curcuma longa). Cancer Lett 29: 197-202. http://dx.doi.org/10.1016/0304-3835(85)90159-4.
31. Ruby A, Kuttan G, Dinesh Babu K, Rajasekharan K, Kuttan R. 1995. Anti-Tumour and antioxidant activity of natural curcuminoids. Cancer Lett 94: 79-83. http://dx.doi.org/10.1016/0304-3835(95)03827-J.
32. Anto RJ, Mukhopadhyay A, Denning K, Aggarwal BB. 2002. Curcumin diferuloylmethane. induces apoptosis through activation of caspase-8, BID cleavage and cytochrome c release: Its suppression by ectopic expression of Bcl-2 and Bcl-xl. Carcinogenesis 23: 143-150. http://dx.doi.org/10.1093/carcin/23.1.143.
33. Bharti AC, Donato N, Singh S, Aggarwal BB. 2003. Curcumin diferuloylmethane. down-regulates the constitutive activation of nuclear factor-κB and IB kinase in human multiple myeloma cells, leading to suppression of proliferation and induction of apoptosis. Blood 101: 1053-1062. http://dx.doi.org/10.1182/blood-2002-05-1320.
34. Aoki H, Takada Y, Kondo S, Sawaya R, Aggarwal BB, Kondo Y. 2007. Evidence that curcumin suppresses the growth of malignant gliomas in vitro and in vivo through induction of autophagy: Role of Akt and extracellular signal-regulated kinase signaling pathways. Mol Pharmacol 72: 29-39. http://dx.doi.org/10.1124/mol.106.033167.
35. Anuchapreeda S, Tima S, Duangrat C, Limtrakul P. 2008. Effect of pure curcumin, demethoxycurcumin, and bisdemethoxycurcumin on WT1 gene expression in leukemic cell lines. Cancer Chemother Pharmacol 62: 585-594. http://dx.doi.org/10.1007/s00280-007-0642-1.
36. Dhillon N, Aggarwal BB, Newman RA, Wolff RA, Kunnumakkara AB, Abbruzzese JL, Ng CS, Badmaev V, Kurzrock R. 2008. Phase II trial of curcumin in patients with advanced pancreatic cancer. Clin Cancer Res 14: 4491-4499. http://dx.doi.org/10.1158/1078-0432.CCR-08-0024.
37. Yallapu MM, Ebeling MC, Khan S, Sundram V, Chauhan N, Gupta BK, Puumala SE, Jaggi M, Chauhan SC. 2013. Novel curcumin loaded magnetic nanoparticles for pancreatic cancer treatment. Mol Cancer Ther 12: 1471-1480. http://dx.doi.org/10.1158/1535-7163.MCT-12-1227.
38. Yallapu MM, Maher DM, Sundram V, Bell MC, Jaggi M, Chauhan SC. 2010. Curcumin induces chemo/radio-sensitization in ovarian cancer cells and curcumin nanoparticles inhibit ovarian cancer cell growth. J Ovarian Res 3: 11. http://dx.doi.org/10.1186/1757-2215-3-11.
39. Skommer J, Wlodkowic D, Pelkonen J. 2006. Cellular foundation of curcumin-induced apoptosis in follicular lymphoma cell lines. Exp Hematol 34: 463-474. http://dx.doi.org/10.1016/j.exphem.2005.12.015.
40. Singh S, Aggarwal BB. 1995. Activation of transcription factor NF-κB is suppressed by curcumin diferuloylmethane). J Biol Chem 270: 24995-25000. http://dx.doi.org/10.1074/jbc.270.42.24995.
41. Rao DS, Sekhara NC, Satyanarayana M, Srinivasan M. 1970. Effect of curcumin on serum and liver cholesterol levels in the rat. J Nutr 100: 1307-1315.
42. Kim M, Kim Y. 2010. Hypocholesterolemic effects of curcumin via up-regulation of cholesterol 7a-hydroxylase in rats fed a high fat diet. Nutr Res Pract 4: 191-195. http://dx.doi.org/10.4162/nrp.2010.4.3.191.
43. Arun N, Nalini N. 2002. Efficacy of turmeric on blood sugar and polyol pathway in diabetic albino rats. Plant Foods Hum Nutr 57: 41-52. http://dx.doi.org/10.1023/A: 1013106527829.
44. Peeyush KT, Gireesh G, Jobin M, Paulose C. 2009. Neuroprotective role of curcumin in the cerebellum of streptozotocin-induced diabetic rats. Life Sci 85: 704-710. http://dx.doi.org/10.1016/j.lfs.2009.09.012.
45. Kumar TP, Antony S, Gireesh G, George N, Paulose C. 2010. Curcumin modulates dopaminergic receptor, CREB and phospholipase c gene expression in the cerebral cortex and cerebellum of streptozotocin induced diabetic rats. J Biomed Sci 17: 43. http://dx.doi.org/10.1186/1423-0127-17-43.
46. Kim T, Davis J, Zhang AJ, He X, Mathews ST. 2009. Curcumin activates AMPK and suppresses gluconeogenic gene expression in hepatoma cells. Biochem Biophys Res Commun 388: 377-382. http://dx.doi.org/10.1016/j.bbrc.2009.08.018.
47. Srimal R, Dhawan B. 1973. Pharmacology of diferuloyl methane curcumin), a non-steroidal anti-inflammatory agent. J Pharm Pharmacol 25: 447-452. http://dx.doi.org/10.1111/j.2042-7158.1973.tb09131.x.
48. Mukhopadhyay A, Basu N, Ghatak N, Gujral P. 1982. Antiinflammatory and irritant activities of curcumin analogues in rats. Agents Actions 12: 508-515. http://dx.doi.org/10.1007/BF01965935.
49. Motterlini R, Foresti R, Bassi R, Green CJ. 2000. Curcumin, an antioxidant and anti-inflammatory agent, induces heme oxygenase-1 and protects endothelial cells against oxidative stress. Free Radical Biol Med 28: 1303-1312. http://dx.doi.org/10.1016/S0891-5849(00)00294-X.
50. Sandur SK, Ichikawa H, Pandey MK, Kunnumakkara AB, Sung B, Sethi G, Aggarwal BB. 2007. Role of pro-oxidants and antioxidants in the anti-inflammatory and apoptotic effects of curcumin diferuloylmethane). Free Radical Biol Med 43: 568-580. http://dx.doi.org/10.1016/j.freeradbiomed.2007.05.009.
51. Menon VP, Sudheer AR. 2007. Antioxidant and anti-inflammatory properties of curcumin, p 105-125. In Aggarwal BB, Surh Y-J, Shishodia S ed), The molecular targets and therapeutic uses of curcumin in health and disease. Springer, New York, NY.
52. Huang M-T, Lysz T, Ferraro T, Abidi TF, Laskin JD, Conney AH. 1991. Inhibitory effects of curcumin on in vitro lipoxygenase and cyclooxygenase activities in mouse epidermis. Cancer Res 51: 813-819.
53. Sharma O. 1976. Antioxidant activity of curcumin and related compounds. Biochem Pharmacol 25: 1811-1812. http://dx.doi.org/10.1016/0006-2952(76)90421-4.
54. Toda S, Miyase T, Arichi H, Tanizawa H, Takino Y. 1985. Natural antioxidants. III. Antioxidative components isolated from rhizome of Curcuma longa L. Chem Pharm Bull 33: 1725-1728.
55. Ahsan H, Parveen N, Khan NU, Hadi SM. 1999. Pro-oxidant, antioxidant and cleavage activities on DNA of curcumin and its derivatives demethoxycurcumin and bisdemethoxycurcumin. Chem Biol Interact 121: 161-175. http://dx.doi.org/10.1016/S0009-2797(99)00096-4.
56. Lim GP, Chu T, Yang F, Beech W, Frautschy SA, Cole GM. 2001. The curry spice curcumin reduces oxidative damage and amyloid pathology in an Alzheimer transgenic mouse. J Neurosci 21: 8370-8377.
57. Ringman JM, Frautschy SA, Cole GM, Masterman DL, Cummings JL. 2005. A potential role of the curry spice curcumin in Alzheimer's disease. Curr Alzheimer Res 2: 131-136. http://dx.doi.org/10.2174/1567205053585882.
58. Ryu EK, Choe YS, Lee K-H, Choi Y, Kim B-T. 2006. Curcumin and dehydrozingerone derivatives: Synthesis, radiolabeling, and evaluation for β-Amyloid plaque imaging. J Med Chem 49: 6111-6119. http://dx.doi.org/10.1021/jm0607193.
59. Garcia-Alloza M, Borrelli L, Rozkalne A, Hyman B, Bacskai B. 2007. Curcumin labels amyloid pathology in vivo, disrupts existing plaques, and partially restores distorted neurites in an Alzheimer mouse model. J Neurochem 102: 1095-1104. http://dx.doi.org/10.1111/j.1471-4159.2007.04613.x.
60. Jordan W, Drew C. 1996. Curcumin-A natural herb with anti-HIV activity. J Natl Med Assoc 88: 333.
61. Sui Z, Salto R, Li J, Craik C, Ortiz de Montellano PR. 1993. Inhibition of the HIV-1 and HIV-2 proteases by curcumin and curcumin boron complexes. Biorg Med Chem 1: 415-422. http://dx.doi.org/10.1016/S0968-0896(00)82152-5.
62. Gandapu U, Chaitanya R, Kishore G, Reddy RC, Kondapi AK. 2011. Curcumin-loaded apotransferrin nanoparticles provide efficient cellular uptake and effectively inhibit HIV-1 replication in vitro. PLoS One 6: E23388. http://dx.doi.org/10.1371/journal.pone.0023388.
63. Sidhu GS, Mani H, Gaddipati JP, Singh AK, Seth P, Banaudha KK, Patnaik GK, Maheshwari RK. 1999. Curcumin enhances wound healing in streptozotocin induced diabetic rats and genetically diabetic mice. Wound Repair Regen 7: 362-374. http://dx.doi.org/10.1046/j.1524-475X.1999.00362.x.
64. Gopinath D, Ahmed MR, Gomathi K, Chitra K, Sehgal P, Jayakumar R. 2004. Dermal wound healing processes with curcumin incorporated collagen films. Biomaterials 25: 1911-1917. http://dx.doi.org/10.1016/S0142-9612(03)00625-2.
65. Pandey N, Strider J, Nolan WC, Yan SX, Galvin JE. 2008. Curcumin inhibits aggregation of β-synuclein. Acta Neuropathol 115: 479-489. http://dx.doi.org/10.1007/s00401-007-0332-4.
66. Pan J, Li H, Ma J-F, Tan Y-Y, Xiao Q, Ding J-Q, Chen S-D. 2012. Curcumin inhibition of JNKs prevents dopaminergic neuronal loss in a mouse model of Parkinson's disease through suppressing mitochondria dysfunction. Transl Neurodegen 1: 1-9. http://dx.doi.org/10.1186/2047-9158-1-1.
67. Sreejayan Rao MNA. 1997. Nitric oxide scavenging by curcuminoids. J Pharm Pharmacol 49: 105-107. http://dx.doi.org/10.1111/j.2042-7158.1997.tb06761.x.
68. Thapliyal R, Maru G. 2001. Inhibition of cytochrome P450 isozymes by curcumins in vitro and in vivo. Food Chem Toxicol 39: 541-547. http://dx.doi.org/10.1016/S0278-6915(00)00165-4.
69. Majeed M, Badmaev V, Rajendran R. November 2002. Bioprotectant composition, method of use and extraction process of curcuminoids. EP patent 0,839,037.
70. Hsu C-H, Cheng A-L. 2007. Clinical studies with curcumin, p 471-480. In Aggarwal BB, Surh Y-J, Shishodia S ed), The molecular targets and therapeutic uses of curcumin in health and disease. Springer, New York, NY.
71. Li R, Qiao X, Li Q, He R, Ye M, Xiang C, Lin X, Guo D. 2011. Metabolic and pharmacokinetic studies of curcumin, demethoxycurcumin and bisdemethoxycurcumin in mice tumor after intragastric administration of nanoparticle formulations by liquid chromatography coupled with tandem mass spectrometry. J Chromatogr B 879: 2751-2758. http://dx.doi.org/10.1016/j.jchromb.2011.07.042.
72. Cheng A-L, Hsu C-H, Lin J-K, Hsu M-M, Ho Y-F, Shen T-S, Ko J-Y, Lin J-T, Lin B, Wu M-S, Yu H, Jee S-H, Chen G, Chen T, Chen C, Lai M, Pu Y, Pan M, Wang Y, Tsai C, Hsieh C. 2001. Phase I clinical trial of curcumin, a chemopreventive agent, in patients with high-risk or premalignant lesions. Anticancer Res 21: 2895-2900.
73. Sharma RA, Euden SA, Platton SL, Cooke DN, Shafayat A, Hewitt HR, Marczylo TH, Morgan B, Hemingway D, Plummer SM. 2004. Phase I clinical trial of oral curcumin biomarkers of systemic activity and compliance. Clin Cancer Res 10: 6847-6854. http://dx.doi.org/10.1158/1078-0432.CCR-04-0744.
74. Vareed SK, Kakarala M, Ruffin MT, Crowell JA, Normolle DP, Djuric Z, Brenner DE. 2008. Pharmacokinetics of curcumin conjugate metabolites in healthy human subjects. Cancer Epidemiol Biomarkers Prevention 17: 1411-1417. http://dx.doi.org/10.1158/1055-9965.EPI-07-2693.
75. Thomas J, Tarka S, Soni M. 2013. Expert panel statement: Determination of the generally recognized as safe GRAS. status of curcumin Curcumin C3 Complex. as a food ingredient. GRAS notice GRN. no. 460. Accessed 17 June 2014. http://www.fda.gov/Food/IngredientsPackaging Labeling/GRAS/.
76. Anand P, Kunnumakkara AB, Newman RA, Aggarwal BB. 2007. Bioavailability of curcumin: Problems and promises. Mol Pharm 4: 807-818. http://dx.doi.org/10.1021/mp700113r.
77. Cruz-Correa M, Shoskes DA, Sanchez P, Zhao R, Hylind LM, Wexner SD, Giardiello FM. 2006. Combination treatment with curcumin and quercetin of adenomas in familial adenomatous polyposis. Clin Gastroenterol Hepatol 4: 1035-1038. http://dx.doi.org/10.1016/j.cgh.2006.03.020.
78. Shoba G, Joy D, Joseph T, Majeed M, Rajendran R, Srinivas P. 1998. Influence of piperine on the pharmacokinetics of curcumin in animals and human volunteers. Planta Med 64: 353-356. http://dx.doi.org/10.1055/s-2006-957450.
79. Li L, Ahmed B, Mehta K, Kurzrock R. 2007. Liposomal curcumin with and without oxaliplatin: Effects on cell growth, apoptosis, and angiogenesis in colorectal cancer. Mol Cancer Ther 6: 1276-1282. http://dx.doi.org/10.1158/1535-7163.MCT-06-0556.
80. Li L, Braiteh FS, Kurzrock R. 2005. Liposome-encapsulated curcumin. In vitro and in vivo effects on proliferation, apoptosis, signaling, and angiogenesis. Cancer 104: 1322-1331. http://dx.doi.org/10.1002/cncr.21300.
81. Kunwar A, Barik A, Pandey R, Priyadarsini KI. 2006. Transport of liposomal and albumin loaded curcumin to living cells: An absorption and fluorescence spectroscopic study. Biochim Biophys Acta 1760: 1513-1520. http://dx.doi.org/10.1016/j.bbagen.2006.06.012.
82. Suresh D, Srinivasan K. 2007. Studies on the in vitro absorption of spice principles-curcumin, capsaicin and piperine in rat intestines. Food Chem Toxicol 45: 1437-1442. http://dx.doi.org/10.1016/j.fct.2007.02.002.
83. Ma Z, Shayeganpour A, Brocks DR, Lavasanifar A, Samuel J. 2007. High-performance liquid chromatography analysis of curcumin in rat plasma: Application to pharmacokinetics of polymeric micellar formulation of curcumin. Biomed Chromatogr 21: 546-552. http://dx.doi.org/10.1002/bmc.795.
84. Letchford K, Liggins R, Burt H. 2008. Solubilization of hydrophobic drugs by methoxy poly(ethylene glycol)-block-polycaprolactone diblock copolymer micelles: Theoretical and experimental data and correlations. J Pharm Sci 97: 1179-1190. http://dx.doi.org/10.1002/jps.21037.
85. Bisht S, Feldmann G, Soni S, Ravi R, Karikar C, Maitra A, Maitra A. 2007. Polymeric nanoparticle-encapsulated curcumin "nanocurcumin"): A novel strategy for human cancer therapy. J Nanobiotechnol 5: 1-18. http://dx.doi.org/10.1186/1477-3155-5-1.
86. Tiyaboonchai W, Tungpradit W, Plianbangchang P. 2007. Formulation and characterization of curcuminoids loaded solid lipid nanoparticles. Int J Pharm 337: 299-306. http://dx.doi.org/10.1016/j.ijpharm.2006.12.043.
87. Shaikh J, Ankola D, Beniwal V, Singh D, Kumar M. 2009. Nanoparticle encapsulation improves oral bioavailability of curcumin by at least 9-fold when compared to curcumin administered with piperine as absorption enhancer. Eur J Pharm Sci 37: 223-230. http://dx.doi.org/10.1016/j.ejps.2009.02.019.
88. Anand P, Nair HB, Bokyung S, Kunnumakkara AB, Yadav VR, Tekmal RR, Aggarwal BB. 2010. Design of curcumin-loaded PLGA nanoparticles formulation with enhanced cellular uptake, and increased bioactivity in vitro and superior bioavailability in vivo. Biochem Pharmacol 79: 330-338. http://dx.doi.org/10.1016/j.bcp.2009.09.003.
89. Mulik RS, Mönkkönen J, Juvonen RO, Mahadik KR, Paradkar AR. 2010. Transferrin mediated solid lipid nanoparticles containing curcumin: Enhanced in vitro anticancer activity by induction of apoptosis. Int J Pharm 398: 190-203. http://dx.doi.org/10.1016/j.ijpharm.2010.07.021.
90. Kim TH, Jiang HH, Youn YS, Park CW, Tak KK, Lee S, Kim H, Jon S, Chen X, Lee KC. 2011. Preparation and characterization of watersoluble albumin-bound curcumin nanoparticles with improved antitumor activity. Int J Pharm 403: 285-291. http://dx.doi.org/10.1016/j.ijpharm.2010.10.041.
91. Basniwal RK, Buttar HS, Jain V, Jain N. 2011. Curcumin nanoparticles: Preparation, characterization, and antimicrobial study. J Agric Food Chem 59: 2056-2061. http://dx.doi.org/10.1021/jf104402t.
92. Liu A, Lou H, Zhao L, Fan P. 2006. Validated LC/MS/MS assay for curcumin and tetrahydrocurcumin in rat plasma and application to pharmacokinetic study of phospholipid complex of curcumin. J Pharm Biomed Anal 40: 720-727. http://dx.doi.org/10.1016/j.jpba.2005.09.032.
93. Maiti K, Mukherjee K, Gantait A, Saha BP, Mukherjee PK. 2007. Curcumin-phospholipid complex: Preparation, therapeutic evaluation and pharmacokinetic study in rats. Int J Pharm 330: 155-163. http://dx.doi.org/10.1016/j.ijpharm.2006.09.025.
94. Ohori H, Yamakoshi H, Tomizawa M, Shibuya M, Kakudo Y, Takahashi A, Takahashi S, Kato S, Suzuki T, Ishioka C. 2006. Synthesis and biological analysis of new curcumin analogues bearing an enhanced potential for the medicinal treatment of cancer. Mol Cancer Ther 5: 2563-2571. http://dx.doi.org/10.1158/1535-7163.MCT-06-0174.
95. Mosley CA, Liotta DC, Snyder JP. 2007. Highly active anticancer curcumin analogues, p 77-103. In Aggarwal BB, Surh Y-J, Shishodia S ed), The molecular targets and therapeutic uses of curcumin in health and disease Springer, New York, NY.
96. Helson L. 2013. Curcumin diferuloylmethane. delivery methods: A review. BioFactors 39: 21-26. http://dx.doi.org/10.1002/biof.1080.
97. Katsuyama Y, Kita T, Funa N, Horinouchi S. 2009. Curcuminoid biosynthesis by two type III polyketide synthases in the herb Curcuma longa. J Biol Chem 284: 11160-11170. http://dx.doi.org/10.1074/jbc.M900070200.
98. Ramirez-Ahumada M, Timmermann BN, Gang DR. 2006. Biosynthesis of curcuminoids and gingerols in turmeric Curcuma longa. and ginger Zingiber officinale): Identification of curcuminoid synthase and hydroxycinnamoyl-CoA thioesterases. Phytochemistry 67: 2017-2029. http://dx.doi.org/10.1016/j.phytochem.2006.06.028.
99. Dixon RA, Paiva NL. 1995. Stress-induced phenylpropanoid metabolism. Plant Cell 7: 1085-1097.
100. Katsuyama Y, Matsuzawa M, Funa N, Horinouchi S. 2007. In vitro synthesis of curcuminoids by type III polyketide synthase from Oryza sativa. J Biol Chem 282: 37702-37709. http://dx.doi.org/10.1074/jbc.M707569200.
101. Katsuyama Y, Miyazono K-I, Tanokura M, Ohnishi Y, Horinouchi S. 2011. Structural and biochemical elucidation of mechanism for decarboxylative condensation of β-keto acid by curcumin synthase. J Biol Chem 286: 6659-6668. http://dx.doi.org/10.1074/jbc.M110.196279.
102. Katsuyama Y, Kita T, Horinouchi S. 2009. Identification and characterization of multiple curcumin synthases from the herb Curcuma longa. FEBS Lett 583: 2799-2803. http://dx.doi.org/10.1016/j.febslet.2009.07.029.
103. Resmi M, Soniya E. 2012. Molecular cloning and differential expressions of two cDNA encoding type III polyketide synthase in different tissues of Curcuma longa L. Gene 491: 278-283. http://dx.doi.org/10.1016/j.gene.2011.09.025.
104. Xie Z, Ma X, Gang DR. 2009. Modules of co-regulated metabolites in turmeric Curcuma longa. rhizome suggest the existence of biosynthetic modules in plant specialized metabolism. J Exp Bot 60: 87-97. http://dx.doi.org/10.1093/jxb/ern263.
105. Kita T, Imai S, Sawada H, Seto H. 2009. Isolation of dihydrocurcuminoids from cell clumps and their distribution in various parts of turmeric Curcuma longa). Biosci Biotech Biochem 73: 1113-1117. http://dx.doi.org/10.1271/bbb.80871.
106. Katsuyama Y, Matsuzawa M, Funa N, Horinouchi S. 2008. Production of curcuminoids by Escherichia coli carrying an artificial biosynthesis pathway. Microbiology 154: 2620-2628. http://dx.doi.org/10.1099/mic.0.2008/018721-0.
107. Horinouchi S. 2009. Combinatorial biosynthesis of plant medicinal polyketides by microorganisms. Curr Opin Chem Biol 13: 197-204. http://dx.doi.org/10.1016/j.cbpa.2009.02.004.
108. Horinouchi S. 2008. Combinatorial biosynthesis of non-bacterial and unnatural flavonoids, stilbenoids and curcuminoids by microorganisms. J Antibiot 61: 709-728. http://dx.doi.org/10.1038/ja.2008.85.
109. Lussier F-X, Colatriano D, Wiltshire Z, Page JE, Martin VJ. 2012. Engineering microbes for plant polyketide biosynthesis. Comput Struct Biotechnol J 3: 1-11. http://dx.doi.org/10.5936/csbj.201210020.
110. Chemler JA, Koffas MA. 2008. Metabolic engineering for plant natural product biosynthesis in microbes. Curr Opin Biotechnol 19: 597-605. http://dx.doi.org/10.1016/j.copbio.2008.10.011.
111. Jeandet P, Delaunois B, Aziz A, Donnez D, Vasserot Y, Cordelier S, Courot E. 2012. Metabolic engineering of yeast and plants for the production of the biologically active hydroxystilbene, resveratrol. J Biomed Biotechnol 2012: 579089. http://dx.doi.org/10.1155/2012/579089.
112. Halls C, Yu O. 2008. Potential for metabolic engineering of resveratrol biosynthesis. Trends Biotechnol 26: 77-81. http://dx.doi.org/10.1016/j.tibtech.2007.11.002.
113. Miyazono Ki. Um J, Imai FL, Katsuyama Y, Ohnishi Y, Horinouchi S, Tanokura M. 2011. Crystal structure of curcuminoid synthase CUS from Oryza sativa. Proteins 79: 669-673. http://dx.doi.org/10.1002/prot.22888.
114. Morita H, Wanibuchi K, Nii H, Kato R, Sugio S, Abe I. 2010. Structural basis for the one-pot formation of the diarylheptanoid scaffold by curcuminoid synthase from Oryza sativa. Proc Natl Acad Sci U S A 107: 19778-19783. http://dx.doi.org/10.1073/pnas.1011499107.
115. Katsuyama Y, Ohnishi Y, Horinouchi S. 2010. Production of dehydrogingerdione derivatives in Escherichia coli by exploiting a curcuminoid synthase from Oryza sativa and a β-oxidation pathway from Saccharomyces cerevisiae. Chembiochem 11: 2034-2041. http://dx.doi.org/10.1002/cbic.201000379.
116. Miyahisa I, Kaneko M, Funa N, Kawasaki H, Kojima H, Ohnishi Y, Horinouchi S. 2005. Efficient production of 2S)-flavanones by Escherichia coli containing an artificial biosynthetic gene cluster. Appl Microbiol Biotechnol 68: 498-504. http://dx.doi.org/10.1007/s00253-005-1916-3.
117. Hwang EI, Kaneko M, Ohnishi Y, Horinouchi S. 2003. Production of plant-specific flavanones by Escherichia coli containing an artificial gene cluster. Appl Environ Microbiol 69: 2699-2706. http://dx.doi.org/10.1128/AEM.69.5.2699-2706.2003.
118. Katsuyama Y, Funa N, Horinouchi S. 2007. Precursor-directed biosynthesis of stilbene methyl ethers in Escherichia coli. Biotechnol J 2: 1286-1293. http://dx.doi.org/10.1002/biot.200700098.
119. Katsuyama Y, Funa N, Miyahisa I, Horinouchi S. 2007. Synthesis of unnatural flavonoids and stilbenes by exploiting the plant biosynthetic pathway in Escherichia coli. Chem Biol 14: 613-621. http://dx.doi.org/10.1016/j.chembiol.2007.05.004.
120. Kikuzaki H., Hisamoto M., Hirose K., Akiyama K., Taniguchi H. Antioxidant properties of ferulic acid and its related compounds.
121. Kikuzaki H, Hisamoto M, Hirose K, Akiyama K, Taniguchi H. 2002. Antioxidant properties of ferulic acid and its related compounds. J Agric Food Chem 50: 2161-2168. http://dx.doi.org/10.1021/jf011348w. 121. Katsuyama Y, Hirose Y, Funa N, Ohnishi Y, Horinouchi S. 2010. Precursor-directed biosynthesis of curcumin analogs in Escherichia coli. Biosci Biotech Biochem 74: 641-645. http://dx.doi.org/10.1271/bbb.90866.
122. Wang S, Zhang S, Zhou T, Zeng J, Zhan J. 2013. Design and application of an in vivo reporter assay for phenylalanine ammonia-lyase. Appl Microbiol Biotechnol 97: 7877-7885. http://dx.doi.org/10.1007/s00253-013-5122-4.
123. Trantas E, Panopoulos N, Ververidis F. 2009. Metabolic engineering of the complete pathway leading to heterologous biosynthesis of various flavonoids and stilbenoids in Saccharomyces cerevisiae. Metab Eng 11: 355-366. http://dx.doi.org/10.1016/j.ymben.2009.07.004.
124. Beekwilder J, Wolswinkel R, Jonker H, Hall R, de Vos CR, Bovy A. 2006. Production of resveratrol in recombinant microorganisms. Appl Environ Microbiol 72: 5670-5672. http://dx.doi.org/10.1128/AEM.00609-06.
125. Becker JV, Armstrong GO, Merwe MJ, Lambrechts MG, Vivier MA, Pretorius IS. 2003. Metabolic engineering of Saccharomyces cerevisiae for the synthesis of the wine-related antioxidant resveratrol. FEMS Yeast Res 4: 79-85. http://dx.doi.org/10.1016/S1567-1356(03)00157-0.
126. Jiang H, Wood KV, Morgan JA. 2005. Metabolic engineering of the phenylpropanoid pathway in Saccharomyces cerevisiae. Appl Environ Microbiol 71: 2962-2969. http://dx.doi.org/10.1128/AEM.71.6.2962-2969.2005.
127. Yan Y, Kohli A, Koffas MA. 2005. Biosynthesis of natural flavanones in Saccharomyces cerevisiae. Appl Environ Microbiol 71: 5610-5613. http://dx.doi.org/10.1128/AEM.71.9.5610-5613.2005.
128. Leonard E, Yan Y, Lim KH, Koffas MA. 2005. Investigation of two distinct flavone synthases for plant-specific flavone biosynthesis in Saccharomyces cerevisiae. Appl Environ Microbiol 71: 8241-8248. http://dx.doi.org/10.1128/AEM.71.12.8241-8248.2005.
129. Zhang Y, Li S-Z, Li J, Pan X, Cahoon RE, Jaworski JG, Wang X, Jez JM, Chen F, Yu O. 2006. Using unnatural protein fusions to engineer resveratrol biosynthesis in yeast and mammalian cells. J Am Chem Soc 128: 13030-13031. http://dx.doi.org/10.1021/ja0622094.
130. Wang Y, Halls C, Zhang J, Matsuno M, Zhang Y, Yu O. 2011. Stepwise increase of resveratrol biosynthesis in yeast Saccharomyces cerevisiae by metabolic engineering. Metab Eng 13: 455-463. http://dx.doi.org/10.1016/j.ymben.2011.04.005.
131. Shin S-Y, Jung S-M, Kim M-D, Han NS, Seo J-H. 2012. Production of resveratrol from tyrosine in metabolically engineered Saccharomyces cerevisiae. Enzyme Microb Technol 51: 211-216. http://dx.doi.org/10.1016/j.enzmictec.2012.06.005.
132. Koopman F, Beekwilder J, Crimi B, van Houwelingen A, Hall RD, Bosch D, van Maris AJ, Pronk JT, Daran J-M. 2012. De novo production of the flavonoid naringenin in engineered Saccharomyces cerevisiae. Microb Cell Fact 11: 155. http://dx.doi.org/10.1186/1475-2859-11-155.
133. Sahdev S, Khattar SK, Saini KS. 2008. Production of active eukaryotic proteins through bacterial expression systems: A review of the existing biotechnology strategies. Mol Cell Biochem 307: 249-264.
134. Popuri AK, Pagala B. 2013. Extraction of curcumin from turmeric roots. Int J Innovative Res Stud 2: 289-299.
135. Paulucci VP, Couto RO, Teixeira CC, Freitas LAP. 2013. Optimization of the extraction of curcumin from Curcuma longa rhizomes. Brazil J Pharmacog 23: 94-100. http://dx.doi.org/10.1590/S0102-695X2012005000117.
136. Gaikar VG, Dandekar DV. May 2001. Process for extraction of curcuminoids from curcuma species. US patent 6,224,877.
137. Xu P, Ranganathan S, Fowler ZL, Maranas CD, Koffas MAG. 2011. Genome-scale metabolic network modeling results in minimal interventions that cooperatively force carbon flux towards malonyl-CoA. Metab Eng 13: 578-587. http://dx.doi.org/10.1016/j.ymben.2011.06.008.
138. Leonard E, Yan Y, Fowler ZL, Li Z, Lim C-G, Lim K-H, Koffas MA. 2008. Strain improvement of recombinant Escherichia coli for efficient production of plant flavonoids. Mol Pharm 5: 257-265. http://dx.doi.org/10.1021/mp7001472.
139. Sydor T, Schaffer S, Boles E. 2010. Considerable increase in resveratrol production by recombinant industrial yeast strains with use of rich medium. Appl Environ Microbiol 76: 3361-3363. http://dx.doi.org/10.1128/AEM.02796-09.
140. Lin Y, Yan Y. 2012. Biosynthesis of caffeic acid in Escherichia coli using its endogenous hydroxylase complex. Microb Cell Fact 11: 42. http://dx.doi.org/10.1186/1475-2859-11-42.
141. Kang S-Y, Choi O, Lee JK, Hwang BY, Uhm T-B, Hong Y-S. 2012. Artificial biosynthesis of phenylpropanoic acids in a tyrosine overproducing Escherichia coli strain. Microb Cell Fact 11: 153. http://dx.doi.org/10.1186/1475-2859-11-153.
142. Sprenger GA. 2007. From scratch to value: Engineering Escherichia coli wild type cells to the production of L-phenylalanine and other fine chemicals derived from chorismate. Appl Microbiol Biotechnol 75: 739-749. http://dx.doi.org/10.1007/s00253-007-0931-y.
143. Pittard J, Camakaris H, Yang J. 2005. The TyrR regulon. Mol Microbiol 55: 16-26. http://dx.doi.org/10.1111/j.1365-2958.2004.04385.x.
144. Bongaerts J, Krämer M, Müller U, Raeven L, Wubbolts M. 2001. Metabolic engineering for microbial production of aromatic amino acids and derived compounds. Metab Eng 3: 289-300. http://dx.doi.org/10.1006/mben.2001.0196.
145. Lütke-Eversloh T, Stephanopoulos G. 2005. Feedback inhibition of chorismate mutase/prephenate dehydrogenase TyrA. of Escherichia coli: Generation and characterization of tyrosine-insensitive mutants. Appl Environ Microbiol 71: 7224-7228. http://dx.doi.org/10.1128/AEM.71.11.7224-7228.2005.
146. Berry A. 1996. Improving production of aromatic compounds in Escherichia coli by metabolic engineering. Trends Biotechnol 14: 250-256. http://dx.doi.org/10.1016/0167-7799(96)10033-0.
147. Draths K, Pompliano D, Conley D, Frost J, Berry A, Disbrow G, Staversky R, Lievense J. 1992. Biocatalytic synthesis of aromatics from D-glucose: The role of transketolase. J Am Chem Soc 114: 3956-3962. http://dx.doi.org/10.1021/ja00036a050.
148. Lütke-Eversloh T, Stephanopoulos G. 2007. L-Tyrosine production by deregulated strains of Escherichia coli. Appl Microbiol Biotechnol 75: 103-110. http://dx.doi.org/10.1007/s00253-006-0792-9.
149. Juminaga D, Baidoo EE, Redding-Johanson AM, Batth TS, Burd H, Mukhopadhyay A, Petzold CJ, Keasling JD. 2012. Modular engineering of L-Tyrosine production in Escherichia coli. Appl Environ Microbiol 78: 89-98. http://dx.doi.org/10.1128/AEM.06017-11.
150. Santos CNS, Koffas M, Stephanopoulos G. 2011. Optimization of a heterologous pathway for the production of flavonoids from glucose. Metab Eng 13: 392-400. http://dx.doi.org/10.1016/j.ymben.2011.02.002.
151. Huang Q, Lin Y, Yan Y. 2013. Caffeic acid production enhancement by engineering a phenylalanine over-producing Escherichia coli strain. Biotechnol Bioeng 110: 3188-3196. http://dx.doi.org/10.1002/bit.24988.
152. Zhang H, Stephanopoulos G. 2013. Engineering E. Coli for caffeic acid biosynthesis from renewable sugars. Appl Microbiol Biotechnol 97: 3333-3341. http://dx.doi.org/10.1007/s00253-012-4544-8.
153. Kim M-J, Kim B-G, Ahn J-H. 2013. Biosynthesis of bioactive O-methylated flavonoids in Escherichia coli. Appl Microbiol Biotechnol 97: 7195-7204. http://dx.doi.org/10.1007/s00253-013-5020-9.
154. Berner M, Krug D, Bihlmaier C, Vente A, Müller R, Bechthold A. 2006. Genes and enzymes involved in caffeic acid biosynthesis in the actinomycete Saccharothrix espanaensis. J Bacteriol 188: 2666-2673. http://dx.doi.org/10.1128/JB.188.7.2666-2673.2006.
155. Choi O, Wu C-Z, Kang SY, Ahn JS, Uhm T-B, Hong Y-S. 2011. Biosynthesis of plant-specific phenylpropanoids by construction of an artificial biosynthetic pathway in Escherichia coli. J Ind Microbiol Biotechnol 38: 1657-1665. http://dx.doi.org/10.1007/s10295-011-0954-3.
156. Furuya T, Arai Y, Kino K. 2012. Biotechnological production of caffeic acid by bacterial cytochrome P450 CYP199A2. Appl Environ Microbiol 78: 6087-6094. http://dx.doi.org/10.1128/AEM.01103-12.
157. Vannelli T, Xue Z, Breinig S, Qi WW, Sariaslani FS. 2007. Functional expression in Escherichia coli of the tyrosine-inducible tyrosine ammonia-lyase enzyme from yeast Trichosporon cutaneum for production of p-hydroxycinnamic acid. Enzyme Microb Technol 41: 413-422. http://dx.doi.org/10.1016/j.enzmictec.2007.03.013.
158. Watts KT, Lee PC, Schmidt-Dannert C. 2006. Biosynthesis of plantspecific stilbene polyketides in metabolically engineered Escherichia coli. BMC Biotechnol 6: 22. http://dx.doi.org/10.1186/1472-6750-6-22.
159. Leonard E, Yan Y, Koffas MAG. 2006. Functional expression of a P450 flavonoid hydroxylase for the biosynthesis of plant-specific hydroxylated flavonols in Escherichia coli. Metab Eng 8: 172-181. http://dx.doi.org/10.1016/j.ymben.2005.11.001.
160. Leonard E, Chemler J, Lim KH, Koffas MA. 2006. Expression of a soluble flavone synthase allows the biosynthesis of phytoestrogen derivatives in Escherichia coli. Appl Microbiol Biotechnol 70: 85-91. http://dx.doi.org/10.1007/s00253-005-0059-x.
161. Watts KT, Lee PC, Schmidt-Dannert C. 2004. Exploring recombinant flavonoid biosynthesis in metabolically engineered Escherichia coli. Chembiochem 5: 500-507. http://dx.doi.org/10.1002/cbic.200300783.
162. Miyahisa I, Funa N, Ohnishi Y, Martens S, Moriguchi T, Horinouchi S. 2006. Combinatorial biosynthesis of flavones and flavonols in Escherichia coli. Appl Microbiol Biotechnol 71: 53-58. http://dx.doi.org/10.1007/s00253-005-0116-5.
163. Mori H, Iwahashi H. 2009. Antioxidant activity of caffeic acid through a novel mechanism under uva irradiation. J Clin Biochem Nutr 45: 49-55. http://dx.doi.org/10.3164/jcbn.08-258.
164. Chao P, Hsu C, Yin M. 2009. Anti-inflammatory and anti-coagulatory activities of caffeic acid and ellagic acid in cardiac tissue of diabetic mice. Nutr Metab 6: 1-8. http://dx.doi.org/10.1186/1743-7075-6-1.
165. Prasad NR, Karthikeyan A, Karthikeyan S, Reddy BV. 2011. Inhibitory effect of caffeic acid on cancer cell proliferation by oxidative mechanism in human HT-1080 fibrosarcoma cell line. Mol Cell Biochem 349: 11-19. http://dx.doi.org/10.1007/s11010-010-0655-7.
166. Mulert U, Luzhetskyy A, Hofmann C, Mayer A, Bechthold A. 2004. Expression of the landomycin biosynthetic gene cluster in a PKS mutant of Streptomyces fradiae is dependent on the coexpression of a putative transcriptional activator gene. FEMS Microbiol Lett 230: 91-97. http://dx.doi.org/10.1016/S0378-1097(03)00861-9.
167. Park SR, Yoon JA, Paik JH, Park JW, Jung WS, Ban Y-H, Kim EJ, Yoo YJ, Han AR, Yoon YJ. 2009. Engineering of plant-specific phenylpropanoids biosynthesis in Streptomyces venezuelae. J Biotechnol 141: 181-188. http://dx.doi.org/10.1016/j.jbiotec.2009.03.013.
168. Hotze M, Schröder G, Schröder J. 1995. Cinnamate 4-hydroxylase from Catharanthus roseus and a strategy for the functional expression of plant cytochrome P450 proteins as translational fusions with P450 reductase in Escherichia coli. FEBS Lett 374: 345-350. http://dx.doi.org/10.1016/0014-5793(95)01141-Z.
169. Kneusel RE, Matern U, Nicolay K. 1989. Formation of trans-caffeoyl-CoA from trans-4-coumaroyl-CoA by Zn2-dependent enzymes in cultured plant cells and its activation by an elicitor-induced pH shift. Arch Biochem Biophys 269: 455-462. http://dx.doi.org/10.1016/0003-9861(89)90129-X.
170. Xue Z, McCluskey M, Cantera K, Sariaslani FS, Huang L. 2007. Identification, characterization and functional expression of a tyrosine ammonia-lyase and its mutants from the photosynthetic bacterium Rhodobacter sphaeroides. J Ind Microbiol Biotechnol 34: 599-604. http://dx.doi.org/10.1007/s10295-007-0229-1.
171. Xue Z, McCluskey M, Cantera K, Ben-Bassat A, Sariaslani FS, Huang L. 2007. Improved production of p-hydroxycinnamic acid from tyrosine using a novel thermostable phenylalanine/tyrosine ammonia lyase enzyme. Enzyme Microb Technol 42: 58-64. http://dx.doi.org/10.1016/j.enzmictec.2007.07.025.
172. Kim YH, Kwon T, Yang HJ, Kim W, Youn H, Lee JY, Youn B. 2011. Gene engineering, purification, crystallization and preliminary X-ray diffraction of cytochrome P450 p-coumarate-3-hydroxylase C3H), the Arabidopsis membrane protein. Protein Expr Purif 79: 149-155. http://dx.doi.org/10.1016/j.pep.2011.04.013.
173. Gatenby AA, Sariaslani S, Tang X-S, Qi WW, Vannelli T. April 2002. Bioproduction of para-hydroxycinnamic acid. US patent 6,368,837.
174. Vannelli T, Wei Qi W, Sweigard J, Gatenby AA, Sariaslani FS. 2007. Production of p-hydroxycinnamic acid from glucose in Saccharomyces cerevisiae and Escherichia coli by expression of heterologous genes from plants and fungi. Metab Eng 9: 142-151. http://dx.doi.org/10.1016/j.ymben.2006.11.001.
175. Lin Y, Sun X, Yuan Q, Yan Y. 2013. Combinatorial biosynthesis of plant-specific coumarins in bacteria. Metab Eng 18: 69-77. http://dx.doi.org/10.1016/j.ymben.2013.04.004.
176. Beuerle T, Pichersky E. 2002. Enzymatic synthesis and purification of aromatic coenzyme A esters. Anal Biochem 302: 305-312. http://dx.doi.org/10.1006/abio.2001.5574.
177. Furuya T, Kino K. 2014. Catalytic activity of the two-component flavindependent monooxygenase from Pseudomonas aeruginosa toward cinnamic acid derivatives. Appl Microbiol Biotechnol 98: 1145-1154. http://dx.doi.org/10.1007/s00253-013-4958-y.
178. Kaneko M, Ohnishi Y, Horinouchi S. 2003. Cinnamate: Coenzyme A ligase from the filamentous bacterium Streptomyces coelicolor A3 2). J Bacteriol 185: 20-27. http://dx.doi.org/10.1128/JB.185.1.20-27.2003.
179. Knobloch K-H, Hahlbrock K. 1977. 4-Coumarate: CoA ligase from cell suspension cultures of Petroselinum hortense Hoffm: Partial purification, substrate specificity, and further properties. Arch Biochem Biophys 184: 237-248. http://dx.doi.org/10.1016/0003-9861(77)90347-2.
180. Ehlting J, Büttner D, Wang Q, Douglas CJ, Somssich IE, Kombrink E. 1999. Three 4-coumarate: Coenzyme A ligases in Arabidopsis thaliana represent two evolutionarily divergent classes in angiosperms. Plant J 19: 9-20. http://dx.doi.org/10.1046/j.1365-313X.1999.00491.x.
181. Hamberger B, Hahlbrock K. 2004. The 4-coumarate: CoA ligase gene family in Arabidopsis thaliana comprises one rare, sinapate-Activating and three commonly occurring isoenzymes. Proc Natl Acad Sci U S A 101: 2209-2214. http://dx.doi.org/10.1073/pnas.0307307101.
182. Schneider K, Hövel K, Witzel K, Hamberger B, Schomburg D, Kombrink E, Stuible H-P. 2003. The substrate specificity-determining amino acid code of 4-coumarate: CoA ligase. Proc Natl Acad Sci USA100: 8601-8606. http://dx.doi.org/10.1073/pnas.1430550100.
183. Schneider K. 2005. Mechanismus der Substratselektion durch Adenylat bildende Enzyme: Analyse der 4-Cumarat: CoA-Ligase 4CL. und ausgewählter 4CL-Ähnlicher Enzyme aus Arabidopsis thaliana. Ph.D. thesis. Cuvillier Verlag, Göttingen, Germany.
184. Gui J, Shen J, Li L. 2011. Functional characterization of evolutionarily divergent 4-coumarate: Coenzyme A ligases in rice. Plant Physiol 157: 574-586. http://dx.doi.org/10.1104/pp.111.178301.
185. Lozoya E, Hoffmann H, Douglas C, Schulz W, Scheel D, Hahlbrock K. 1988. Primary structures and catalytic properties of isoenzymes encoded by the two 4-coumarate: CoA ligase genes in parsley. Eur J Biochem 176: 661-667. http://dx.doi.org/10.1111/j.1432-1033.1988.tb14328.x.
186. Shin S-Y, Han NS, Park Y-C, Kim M-D, Seo J-H. 2011. Production of resveratrol from p-coumaric acid in recombinant Saccharomyces cerevisiae expressing 4-coumarate: Coenzyme A ligase and stilbene synthase genes. Enzyme Microb Technol 48: 48-53. http://dx.doi.org/10.1016/j.enzmictec.2010.09.004.
187. Brand S, Hölscher D, Schierhorn A, Svatoš A, Schröder J, Schneider B. 2006. A type III polyketide synthase from Wachendorfia thyrsiflora and its role in diarylheptanoid and phenylphenalenone biosynthesis. Planta 224: 413-428. http://dx.doi.org/10.1007/s00425-006-0228-x.
188. Leonard E, Lim K-H, Saw P-N, Koffas MA. 2007. Engineering central metabolic pathways for high-level flavonoid production in Escherichia coli. Appl Environ Microbiol 73: 3877-3886. http://dx.doi.org/10.1128/AEM.00200-07.
189. Takamura Y, Nomura G. 1988. Changes in the intracellular concentration of acetyl-CoA and malonyl-CoA in relation to the carbon and energy metabolism of Escherichia coli K12. J Gen Microbiol 134: 2249-2253.
190. Xu P, Gu Q, Wang W, Wong L, Bower AG, Collins CH, Koffas MA. 2013. Modular optimization of multi-gene pathways for fatty acids production in E. Coli. Nat Commun 4: 1-8. http://dx.doi.org/10.1038/ncomms2425.
191. Xu P, Vansiri A, Bhan N, Koffas MA. 2012. ePathBrick: A synthetic biology platform for engineering metabolic pathways in E. Coli. ACS Synthet Biol 1: 256-266. http://dx.doi.org/10.1021/sb300016b.
192. Malla S, Koffas MA, Kazlauskas RJ, Kim B-G. 2012. Production of 7-O-methyl aromadendrin, a medicinally valuable flavonoid, in Escherichia coli. Appl Environ Microbiol 78: 684-694. http://dx.doi.org/10.1128/AEM.06274-11.
193. Fowler ZL, Gikandi WW, Koffas MA. 2009. Increased malonyl coenzymeAbiosynthesis by tuning the Escherichia coli metabolic network and its application to flavanone production. Appl Environ Microbiol 75: 5831-5839. http://dx.doi.org/10.1128/AEM.00270-09.
194. Luli GW, Strohl WR. 1990. Comparison of growth, acetate production, and acetate inhibition of Escherichia coli strains in batch and fed-batch fermentations. Appl Environ Microbiol 56: 1004-1011.
195. El-Mansi E, Holms W. 1989. Control of carbon flux to acetate excretion during growth of Escherichia coli in batch and continuous cultures. J Gen Microbiol 135: 2875-2883.
196. Prüss BM, Wolfe AJ. 1994. Regulation of acetyl phosphate synthesis and degradation, and the control of flagellar expression in Escherichia coli. Mol Microbiol 12: 973-984. http://dx.doi.org/10.1111/j.1365-2958.1994.tb01085.x.
197. Wu J, Du G, Zhou J, Chen J. 2013. Metabolic engineering of Escherichia coli for 2S)-pinocembrin production from glucose by a modular metabolic strategy. Metab Eng 16: 48-55. http://dx.doi.org/10.1016/j.ymben.2012.11.009.
198. Neidhardt FC, Bloch PL, Smith DF. 1974. Culture medium for enterobacteria. J Bacteriol 119: 736-747.
199. Keasling JD. 2008. Synthetic biology for synthetic chemistry. ACS Chem Biol 3: 64-76. http://dx.doi.org/10.1021/cb7002434.
200. Pósfai G, Plunkett G, Fehér T, Frisch D, Keil GM, Umenhoffer K, Kolisnychenko V, Stahl B, Sharma SS, De Arruda M. 2006. Emergent properties of reduced-genome Escherichia coli. Science 312: 1044-1046. http://dx.doi.org/10.1126/science.1126439.
201. Kolisnychenko V, Plunkett G, Herring CD, Fehér T, Pósfai J, Blattner FR, Pósfai G. 2002. Engineering a reduced Escherichia coli genome. Genome Res 12: 640-647. http://dx.doi.org/10.1101/gr.217202.
202. Sharma SS, Blattner FR, Harcum SW. 2007. Recombinant protein production in an Escherichia coli reduced genome strain. Metab Eng 9: 133-141. http://dx.doi.org/10.1016/j.ymben.2006.10.002.
203. Sharma SS, Campbell JW, Frisch D, Blattner FR, Harcum SW. 2007. Expression of two recombinant chloramphenicol acetyltransferase variants in highly reduced genome Escherichia coli strains. Biotechnol Bioeng 98: 1056-1070. http://dx.doi.org/10.1002/bit.21491.
204. Keasling JD. 2012. Synthetic biology and the development of tools for metabolic engineering. Metab Eng 14: 189-195. http://dx.doi.org/10.1016/j.ymben.2012.01.004.
205. Furuya T, Kino K. 2009. Discovery of 2-naphthoic acid monooxygenases by genome mining and their use as biocatalysts. Chemsuschem 2: 645-649. http://dx.doi.org/10.1002/cssc.200900054.
206. McNulty DE, Claffee BA, Huddleston MJ, Kane JF. 2003. Mistranslational errors associated with the rare arginine codon CGG in Escherichia coli. Protein Expr Purif 27: 365-374. http://dx.doi.org/10.1016/S1046-5928(02)00610-1.
207. Valdivia E, Isaksson LA. 2004. A codon window in mRNA downstream of the initiation codon where NGG codons give strongly reduced gene expression in Escherichia coli. Nucleic Acids Res 32: 5198-5205. http://dx.doi.org/10.1093/nar/gkh857.
208. Stenström CM, Jin H, Major LL, Tate WP, Isaksson LA. 2001. Codon bias at the 3=-side of the initiation codon is correlated with translation initiation efficiency in Escherichia coli. Gene 263: 273-284. http://dx.doi.org/10.1016/S0378-1119(00)00550-3.
209. Stenström CM, Isaksson LA. 2002. Influences on translation initiation and early elongation by the messengerRNAregion flanking the initiation codon at the 3= side. Gene 288: 1-8. http://dx.doi.org/10.1016/S0378-1119(02)00501-2.