Isolation, bioactivity, and production of ortho-hydroxydaidzein and ortho-hydroxygenistein

International Journal of Molecular Sciences

Volumn 15, Issue 4, 2014, Pages 5699-5716

  Chang, Te Sheng ^a  

^a NATIONAL UNIVERSITY OF TAINAN   (Taiwan)

Author keywords

Bioactivity; Cancer; Daidzein; Genistein; Hydroxylation; Isolation; Melanogenesis; Ortho hydroxydaidzein; Ortho hydroxygenistein; Production; Soy isoflavones

Indexed keywords

ALDOSE REDUCTASE INHIBITOR; ATR PROTEIN; CYCLIN DEPENDENT KINASE 1; CYCLIN DEPENDENT KINASE 2; CYCLOOXYGENASE 2; CYTOCHROME P450 REDUCTASE; DIMETHYLANILINE MONOOXYGENASE; EPIDERMAL GROWTH FACTOR; INTEGRASE INHIBITOR; ISOFLAVONE DERIVATIVE; ORTHO HYDROXY DAIDZEIN; ORTHO HYDROXY GENISTEIN; PHOSPHATIDYLINOSITOL 3 KINASE; PROTEIN P53; REDUCED NICOTINAMIDE ADENINE DINUCLEOTIDE PHOSPHATE; SOYBEAN PROTEIN; TECTORIGENIN; UNCLASSIFIED DRUG; 3'-HYDROXY-GENISTEIN; 3'-HYDROXYDAIDZEIN; 6-HYDROXYDAIDZEIN; 8-HYDROXYDAIDZEIN; CYTOCHROME P450; DAIDZEIN; GENISTEIN;

ANTIMELANOGENIC ACTIVITY; ANTINEOPLASTIC ACTIVITY; BIOLOGICAL ACTIVITY; DRUG ISOLATION; DRUG STRUCTURE; G2 PHASE CELL CYCLE CHECKPOINT; HIGH THROUGHPUT SCREENING; HUMAN; HYDROXYLATION; INDUCED MUTATION; MULTIDRUG RESISTANCE; NONHUMAN; PROTEIN EXPRESSION; REVIEW; ANALOGS AND DERIVATIVES; ASPERGILLUS; BIOSYNTHESIS; CHEMISTRY; ISOLATION AND PURIFICATION; METABOLISM; NEOPLASMS; SOYBEAN;

ASPERGILLUS; CYTOCHROME P-450 ENZYME SYSTEM; GENISTEIN; ISOFLAVONES; NEOPLASMS; SOY FOODS; SOYBEANS;

EID: 84898745139     PISSN: 16616596     EISSN: 14220067     Source Type: Journal    
DOI: 10.3390/ijms15045699     Document Type: Review

References (89)

1. Franke, A. A.; Custer, L. J.; Cerna, C. M.; Narala, K. K. Quantitation of phytoestrogens in legumes by HPLC. J. Agric. Food Chem. 1994, 42, 1905-1913.
2. Harborne, J. B.; Williams, C. A. Advances in flavonoid research since 1992. Phytochemistry 2000, 55, 481-504.
3. Vitale, D. C.; Piazza, C.; Melilli, B.; Drago, F.; Salomone, S. Isoflavones: Estrogenic activity, biological effect and bioavailability. Eur. J. Drug Metab. Pharmacokinet. 2013, 38, 15-25.
4. Scotti, L.; Bezerra Mendonça, F. J., Jr.; Magalhaes Moreira, D. R.; da Silva, M. S.; Pitta, I. R.; Scotti, M. T. SAR, QSAR and docking of anticancer flavonoids and variants: A review. Curr. Top. Med. Chem. 2012, 12, 2785-2809.
5. Roberts-Kirchhoff, E. S.; Crowley, J. R.; Hollenberg, P. F.; Kim, H. Metabolism of genistein by rat and human cytochrome P450s. Chem. Res. Toxicol. 1999, 12, 610-616.
6. Kulling, S. E.; Honig, D. M.; Simat, T. J.; Metzler, M. Oxidative in vitro metabolism of the soy phytoestrogens daidzein and genistein. J. Agric. Food Chem. 2000, 48, 4963-4972.
7. Kulling, S. E.; Honig, D. M.; Metzler, M. Oxidative metabolism of the soy isoflavones daidzein and genistein in humans in vitro and in vivo. J. Agric. Food Chem. 2001, 49, 3024-3033.
8. Xiao, J.; Högger, P. Metabolism of dietary flavonoids in liver microsomes. Curr. Drug Metab. 2013, 14, 381-391.
9. Barnes, S.; Prasain, J.; D'Alessandro, T.; Arabshahi, A.; Botting, N.; Lila, M. A.; Jackson, G.; Janle, E. M.; Weaver, C. M. The metabolism and analysis of isoflavones and other dietary polyphenols in foods and biological systems. Food Funct. 2011, 2, 235-244.
10. Chen, K. I.; Erh, M. H.; Su, N. W.; Liu, W. H.; Chou, C. C.; Cheng, K. C. Soyfoods and soybean products: From traditional use to modern applications. Appl. Microbiol. Biotechnol. 2012, 96, 9-22.
11. Naim, M.; Gestetner, B.; Zilkah, S.; Birk, Y.; Bondi, A. Soybean isoflavones, characterization, and antifungal activity. J. Agric. Food Chem. 1974, 22, 806-810.
12. Kudou, S.; Fleury, Y.; Welti, D.; Magnolato, D.; Uchida, T.; Kitamura, K.; Okubo, K. Malonyl isoflavone glycosides in soybean seeds (Glycine max Merril). Agric. Biol. Chem. 1991, 55, 2227-2233.
13. Esaki, H.; Watanabe, R.; Onozaki, H.; Kawakishi, S.; Osawa, T. Formation mechanism for potent antioxidative o-dihydroxyisoflavones in soybeans fermented with Aspergillus saitoi. Biosci. Biotechnol. Biochem. 1999, 63, 851-858.
14. Chang, T. S.; Ding, H. Y.; Tai, S. S. K.; Wu, C. Y. Metabolism of the soy isoflavone daidzein and genistein by the fungi used for the preparation of various fermented soybean foods. Biosci. Biotechnol. Biochem. 2007, 71, 1330-1333.
15. Nazir, K.; Ichinose, H.; Wariishi, H. Molecular characterization and isolation of cytochrome P450 genes from the filamentous fungus Aspergillus oryzae. Arch. Microbiol. 2010, 192, 395-408.
16. Nazir, N. H.; Ichinose, H.; Wariishi, H. Construction and application of a functional library of cytochrome P450 monooxygenases from the filamentous fungus Aspergillus oryzae. Appl. Environ. Microbiol. 2011, 77, 3147-3150.
17. Bernhardt, R. Cytochromes P450 as versatile biocatalysts. J. Biotechnol. 2006, 124, 128-145.
18. Peng, W. X.; Wang, L. S.; Li, H. D.; Abd El-Aty, A. M.; Chen, G. L.; Zhou, H. H. Evidence for the involvement of human liver microsomes CYP1A2 in the mono-hydroxylation of daidzein. Clin. Chim. Acta 2003, 334, 77-85.
19. Hu, M.; Krausz, K.; Chen, J.; Ge, X.; Li, J.; Gelboin, H. L.; Gonzalez, F. J. Identification of CYP1A2 as the main isoform for the phase I hydroxylated metabolism of genistein and a prodrug converting enzyme of methylated isoflavones. Drug Metab. Dispos. 2003, 31, 924-931.
20. Breinholt, V. M.; Rasmussen, S. E.; Brøsen, K.; Friedberg, T. H. In vitro metabolism of genistein and tangeretin by human and murine cytochrome P450s. Pharmacol. Toxicol. 2003, 93, 14-22.
21. Pandey, B. P.; Lee, N.; Choi, K. Y.; Jung, E.; Jeong, D. H.; Kim, B. G. Screening of bacterial cytochrome P450s responsible for regiospecific hydroxylation of (iso)flavonoids. Enzym. Microbial. Technol. 2011, 48, 386-392.
22. Charaux, C.; Rabate, J. Constitution chimique de I'orobol. Bull. Soc. Chim. Biol. 1939, 21, 1330-1333.
23. Ma, C. H.; Chen, B.; Qi, H. Y.; Li, B. G.; Zhang, G. L. Two pyranocoumarins from the seeds of Calophyllum polyanthum. J. Nat. Prod. 2004, 67, 1598-1600.
24. Matsuda, H.; Morikawa, T.; Xu, F.; Ninomiya, K.; Yoshikawa, M. New isoflavones and pterocarpane with hepatoprotective activity from the stems of Erycibe expansa. Planta Med. 2004, 70, 1201-1209.
25. Tewtrakul, S.; Subhadhirasakul, S.; Cheenpracha, S.; Karalai, C. HIV-1 protease and HIV-1 integrase inhibitory substances from Eclipta prostrata. Phytother. Res. 2007, 21, 1092-1095.
26. Chen, Q. C.; Zhang, W. Y.; Jin, W.; Lee, I. S.; Min, B. S.; Jung, H. J.; Na, M.; Lee, S.; Bae, K. Flavonoids and isoflavonoids from Sophorae Flos improve glucose uptake in vitro. Planta Med. 2010, 76, 79-81.
27. Kiriakidis, S.; Högemeier, O.; Starcke, S.; Dombrowski, F.; Hahne, J. C.; Pepper, M.; Jha, H. C.; Wernert, N. Novel tempeh (fermented soyabean) isoflavones inhibit in vivo angiogenesis in the chicken chorioallantoic membrane assay. Br. J. Nutr. 2005, 93, 317-323.
28. Umezawa, H.; Tobe, H.; Shibamoto, N.; Nakamura, F.; Nakamura, K.; Matsuzaki, M.; Takeuchi, T. Isolation of isoflavones inhibiting dopa decarboxylase from fungi and Streptomyces. J. Antibiot. 1975, 28, 947-952.
29. De Oliveira, A. B.; Gottlieb, O. R.; Ollis, W. D. A quimica de leguminosas Brasileiras. XVII. Constituents do Machaerium villosum. Anais Acad. Brasil. Cienc. 1968, 40, 147-150.
30. Chan, S. C.; Chang, Y. S.; Wang, J. P.; Chen, S. C.; Kuo, S. C. Three new flavonoids and antiallergic, anti-inflammatory constituents from the heartwood of Dalbergia odorifera. Planta Med. 1998, 64, 153-158.
31. Kite, G. K.; Veitch, N. C.; Boalch, M. E.; Lewis, G. P.; Leon, C. J.; Simmonds, M. S. J. Flavonol tetraglycosides from fruits of Styphnolobium japonicum (Leguminosae) and the authentication of Fructus Sophorae and Flos Sophorae. Phytochemistry 2009, 70, 785-794.
32. Gyoergy, P.; Murata, K.; Ikehata, H. Antioxidants isolated from fermented soybeans (tempeh). Nature 1964, 203, 870-872.
33. Esaki, H.; Onozaki, H.; Morimitsu, Y. Potent antioxidative isoflavones isolated from soybean fermented with Aspergillus saitoi. Biosci. Biotechnol. Biochem. 1998, 62, 740-746.
34. Esaki, H.; Kawakishi, S.; Morimitsu, Y.; Osawa, T. New potent antioxidative o-dihydroxyisoflavones in fermented Japanese soybean products. Biosci. Biotechnol. Biochem. 1999, 63, 1637-1639.
35. Hirota, A.; Taki, S.; Kawaii, S.; Yano, M.; Abe, N. 1, 1-Diphenyl-2-picrylhydrazyl radical-scavenging compounds from soybean miso and antiproliferative activity of isoflavones from soybean miso toward the cancer cell lines. Biosci. Biotechnol. Biochem. 2000, 64, 1038-1040.
36. Chen, Y. C.; Inaba, M.; Abe, N.; Hirota, A. Antimutagenic activity of 8-hydroxyisoflavones and 6-hydroxydaidzein from soybean miso. Biosci. Biotechnol. Biochem. 2003, 67, 903-906.
37. Hirota, A.; Inaba, M.; Chen, Y. C.; Abe, N.; Taki, S.; Yano, M.; Kawaii, S. Isolation of 8-hydroxyglycitein and 6-hydroxydaidzein from soybean miso. Biosci. Biotechnol. Biochem. 2004, 68, 1372-1374.
38. Sugiyama, Y.; Sakurai, Y.; Hirota, A. Isolation of 2, 4, 4'-trihydroxydeoxybenzoin and 3'-hydroxydaidzein from soybean miso. Biosci. Biotechnol. Biochem. 2010, 74, 1293-1294.
39. Chen, Y. C.; Sugiyama, Y.; Abe, N.; Kuruto-Niwa, R.; Nozawa, R.; Hirota, A. DPPH radical-scavenging compounds from dou-chi, a soybean fermented food. Biosci. Biotechnol. Biochem. 2005, 69, 999-1006.
40. Park, J. S.; Park, H. Y.; Kim, D. H.; Kim, D. H.; Kim, H. K. ortho-Dihydroxyisoflavone derivatives from aged Doenjang (Korean fermented soypaste) and its radical scavenging activity. Bioorg. Med. Chem. Lett. 2008, 18, 5006-5009.
41. Klus, K.; Borger-Papendorf, G.; Barz, W. Formation of 6, 7, 4'-trihydroxyisoflavone (factor 2) from soybean seed isoflavones by bacteria isolated from tempe. Phytochemistry 1993, 34, 979-981.
42. Klus, K.; Barz, W. Formation of polyhydroxylated isoflavones from the soybean seed isoflavones daidzein and glycitein by bacteria isolated from tempe. Arch. Microbiol. 1995, 164, 428-434.
43. Funayama, S.; Anraku, Y.; Mita, A.; Komiyama, K.; Omura, S. Structure study of isoflavonoids possessing antioxidant activity from the fermentation broth of Streptomyces sp. J. Antibiot. 1989, 42, 1350-1355.
44. Komiyama, K.; Funayama, S.; Anraku, Y.; Mita, A.; Takahashi, Y.; Omura, S. Isolation of isoflavonoids possessing antioxidant activity from the fermentation broth of Streptomyces sp. J. Antibiot. 1989, 42, 1344-1349.
45. Klus, K.; Barz, W. Formation of polyhydroxylated isoflavones from the isoflavones genistein and biochanin A by bacteria isolated from tempe. Phytochemistry 1998, 47, 1045-1048.
46. Tsuchihashi, R.; Kodera, M.; Sakamoto, S.; Nakajima, Y.; Yamazaki, T.; Niiho, Y.; Nohara, T.; Kinjo, J. Microbial transformation and bioconversion of isoflavones from Pueraria flowers by human intestinal bacterial strains. J. Nat. Med. 2009, 63, 254-260.
47. Goto, H.; Terao, Y.; Akai, S. Synthesis of various kinds of isoflavones, isoflavanes, and biphenyl-ketones and their 1, 1-diphenyl-2-picrylhydrazyl radical-scavenging activities. Chem. Pharm. Bull. 2009, 57, 346-360.
48. Bennink, M. R. Dietary soy reduces colon carcinogenesis in human and rats. Soy and colon cancer. Adv. Exp. Med. Biol. 2001, 492, 11-17.
49. Farina, H. G.; Pomies, M.; Alonso, D. F.; Gomez, D. E. Antitumor and antiangiogenic activity of soy isoflavone genistein in mouse models of melanoma and breast cancer. Oncol. Rep. 2006, 16, 885-891.
50. Hewitt, A. L.; Singletary, K. W. Soy extract inhibits mammary adenocarcinoma growth in a syngeneic mouse model. Cancer Lett. 2003, 192, 133-143.
51. Jian, L. Soy, isoflavones, and prostate cancer. Mol. Nutr. Food Res. 2009, 53, 217-226.
52. Nguyen, D. T.; Hernandez-Montes, E.; Vauzour, D.; Schonthal, A. H.; Rice-Evans, C.; Cadenas, E.; Spencer, J. P. E. The intracellular genistein metabolite 5, 7, 3', 4'-tetrahydroxyisoflavone mediates G2-M cell cycle arrest in cancer cells via modulation of the p38 signaling pathway. Free Radic. Biol. Med. 2006, 41, 1225-1239.
53. Vauzour, D.; Vafeiadou, K.; Rice-Evans, C.; Cadenas, E.; Spencer, J. P. E. Inhibition of cellular proliferation by the genistein metabolite 5, 7, 30, 40-tetrahydroxyisoflavone is mediated by DNA damage and activation of the ATR signalling pathway. Arch. Biochem. Biophy. 2007, 468, 159-166.
54. Lee, D. E.; Lee, K. W.; Jung, S. K.; Lee, E. J.; Hwang, J. A.; Lim, T. G.; Kim, B. Y.; Bode, A. M.; Lee, H. J.; Dong, Z. 6, 7, 4'-Trihydroxyisoflavone inhibits HCT-116 human colon cancer cell proliferation by targeting CDK1 and CDK2. Carcinogenesis 2011, 32, 629-635.
55. Lee, D. E.; Lee, K. W.; Byun, S.; Jung, S. K.; Song, N.; Lim, S. H.; Heo, Y. S.; Kim, J. E.; Kang, N. J.; Kim, B. Y.; et al. 7, 3', 4'-Trihydroxyisoflavone, a metabolite of the soy isoflavone daidzein, suppresses ultraviolet B-induced skin cancer by targeting Cot and MKK4. J. Biol. Chem. 2011, 286, 14246-14256.
56. Lee, D. E.; Lee, K. W.; Song, N. R.; Seo, S. K.; Heo, Y. S.; Kang, N. J.; Bode, A. M.; Lee, H. J.; Dong, Z. 7, 3', 4'-Trihydroxyisoflavone inhibits epidermal growth factor-induced proliferation and transformation of JB6 P+ mouse epidermal cells by suppressing cyclin-dependent kinases and phosphatidylinositol 3-kinase. J. Biol. Chem. 2010, 285, 21458-21466.
57. Lo, Y. L.; Wang, W.; Ho, C. T. 7, 3', 4'-Trihydroxyisoflavone modulates multidrug resistance transporters and induces apoptosis via production of reactive oxygen species. Toxicology 2012, 302, 221-232.
58. Lo, Y. L. A potential daidzein derivative enhances cytotoxicity of epirubicin on human colon adenocarcinoma caco-2 cells. Int. J. Mol. Sci. 2012, 14, 158-176.
59. Chang, T. S. An updated review of tyrosinase inhibitors. Int. J. Mol. Sci. 2009, 10, 2440-2475.
60. Chang, T. S.; Ding, H. Y.; Lin, H. C. Identifying 6, 7, 4'-trihydroxyisoflavone as a potent tyrosinase inhibitor. Biosci. Biotechnol. Biochem. 2005, 69, 1999-2001.
61. Chang, T. S.; Ding, H. Y.; Tai, S. S. K.; Wu, C. Y. Tyrosinase inhibitors isolated from soygerm koji fermented with Aspergillus oryzae BCRC 32288. Food Chem. 2007, 105, 1430-1438.
62. Chang, T. S. Two potent suicide substrates of mushroom tyrosinase: 7, 8, 4'-Trihydroxyisoflavone and 5, 7, 8, 4'-tetrahydroxyisoflavone. J. Agric. Food Chem. 2007, 55, 2010-2015.
63. Tai, S. S. K.; Lin, C. G.; Wu, M. H.; Chang, T. S. Evaluation of depigmenting activity by 8-hydroxydaidzein in mouse B16 melanoma cells and human volunteers. Int. J. Mol. Sci. 2009, 10, 4257-4266.
64. Park, J. S.; Kim, D. H.; Lee, J. K.; Lee, J. Y.; Kim, D. H.; Kim, H. K.; Lee, H. J.; Kim, H. C. Natural ortho-dihydroxyisoflavone derivatives from aged Korean fermented soybean paste as potent tyrosinase and melanin formation inhibitors. Bioorg. Med. Chem. Lett. 2010, 20, 1162-1164.
65. Goh, M. J.; Park, J. S.; Bae, J. H.; Kim, D. H.; Kim, H. K.; Na, Y. J. Effects of ortho-dihydroxyisoflavone derivatives from Korean fermented soybean paste on melanogenesis in B16 melanoma cells and human skin equivalents. Phytother. Res. 2012, 26, 1107-1112.
66. Chang, T. S. Natural melanogenesis inhibitors acting through the down-regulation of tyrosinase activity. Materials 2012, 5, 1661-1685.
67. Kim, E. S.; Shin, J. H.; Seok, S. H.; Kim, J. B.; Chang, H.; Park, S. J.; Jo, Y. K.; Choi, E. S.; Park, J. S.; Yeom, M. H.; et al. Autophagy mediates anti-melanogenic activity of 30-ODI in B16F1 melanoma cells. Biochem. Biophy. Res. Commun. 2013, 442, 165-170.
68. Tewtrakul, S.; Subhadhirasakul, S.; Tansakul, P.; Cheenpracha, S.; Karalai, C. Antiinflammatory constituents from Eclipta prostrata using RAW264. 7 macrophage cells. Phytother. Res. 2011, 25, 1313-1316.
69. Fujita, T.; Funako, T.; Hayashi, H. 8-Hydroxydaidzein, an aldose reductase inhibitor from okara fermented with Aspergillus sp. HK-388. Biosci. Biotechnol. Biochem. 2004, 68, 1588-1590.
70. Seo, S. G.; Yang, H.; Shin, S. H.; Min, S.; Kim, Y. A.; Yu, J. G.; Lee, D. E.; Chung, M. Y.; Heo, Y. S.; Kwon, J. Y.; et al. A metabolite of daidzein, 6, 7, 4'-trihydroxyisoflavone, suppresses adipogenesis in 3T3-L1 preadipocytes via ATP-competitive inhibition of PI3K. Mol. Nutr. Food Res. 2013, 57, 1446-1455.
71. Chen, L.; Li, Q. Y.; Shi, X. J.; Mao, S. L.; Du, Y. L. 6-Hydroxydaidzein enhances adipocyte differentiation and glucose uptake in 3T3-L1 cells. J. Agric. Food Chem. 2013, 61, 10714-10719.
72. Tasdemir, D.; Kaiser, M.; Brun, R.; Yardley, V.; Schmidt, T. J.; Tosun, F.; Ruedi, P. Antitrypanosomal and antileishmanial activities of flavonoids and their analogues: In vitro, in vivo, structure-activity relationship, and quantitative structure-activity relationship studies. Antimicrob. Agents Chemother. 2006, 50, 1352-1364.
73. Salem, M. M.; Werbovetz, K. A. Isoflavonoids and other compounds from Psorothamnus arborescens with antiprotozoal activities. J. Nat. Prod. 2006, 69, 43-49.
74. Kim, B. B.; Kim, J. R.; Kim, J. H.; Kim, Y. A.; Park, J. S.; Yeom, M. H.; Lee, H.; Lee, K. W.; Kang, N. J. 7, 3', 4'-Trihydroxyisoflavone ameliorates the development of dermatophagoides farinae-induced atopic dermatitis in NC/Nga Mice. Evid. Based Complement. Alternat. Med. 2013, 2013, 636597.
75. Roh, C.; Choi, K. Y.; Pandey, B. P.; Kim, B. G. Hydroxylation of daidzein by CYP107H1 from Bacillus subtilis 168. J. Mol. Catal. B Enzym. 2009, 59, 248-253.
76. Choi, K. Y.; Kim, T. J.; Koh, S. K.; Roh, C. H.; Pandey, B. P.; Lee, N.; Kim, B. G. A-ring ortho-specific monohydroxylation of daidzein by cytochrome P450s of Nocardia farcinica IFM10152. Biotechnol. J. 2009, 4, 1586-1595.
77. Choi, K. Y.; Park, H. Y.; Kim, B. G. Characterization of bi-functional CYP154 from Nocardia farcinica IFM10152 in the O-deakylation and ortho-hydroxylation of formononetin. Enzym. Microb. Technol. 2010, 47, 327-334.
78. Choi, K. Y.; Jung, E. O.; Jung, D. H.; Pandey, B. P.; Yun, H.; Park, H. Y.; Kazlauskas, R. J.; Kim, B. G. Cloning, expression and characterization of CYP102D1, a self-sufficient P450 monooxygenase from Streptomyces avermitilis. FEBS J. 2012, 279, 1650-1662.
79. Choi, K. Y.; Jung, E. O.; Jung, D. H.; An, B. R.; Pandey, B. P.; Yun, H.; Sung, C.; Park, H. Y.; Kim, B. G. Engineering of daidzein 3'-hydroxylase P450 enzyme into catalytically self-sufficient cytochrome P450. Microb. Cell Fact. 2012, 11, 81.
80. Pandey, B. P.; Roh, C.; Choi, K. Y. Regioselective hydroxylation of daidzein using P450 (CYP105D7) from Streptomyces avermitilis MA4680. Biotechnol. Bioeng. 2010, 105, 697-704.
81. Choi, K. Y.; Jung, E. O.; Kazlauskas, R.; Kim, B. G. Development of colorimetric HTS assay of cytochrome P450 for ortho-specific hydroxylation and engineering of CYP102D1 with enhanced catalytic activity and regioselectivity. Chembiochem 2013, 14, 1231-1238.
82. Lee, H.; Kim, B. G.; Ahn, J. H. Production of bioactive hydroxyflavones by using monooxygenase from Saccharothrix espanaensis. J. Biotechnol. 2014, 176, 11-17.
83. Kim, H. J.; Choi, K. Y.; Jung, D. H.; Jung, J. Y.; Jung, E. O.; Yang, Y. H.; Kim, B. G.; Oh, M. K. Transcriptomic study for screening genes involved in the oxidative bioconversions of Streptomyces avermitilis. Bioprocess Biosyst. Eng. 2013, 36, 1621-1630.
84. Pandey, B. P.; Lee, N.; Choi, K. Y.; Kim, J. N.; Kim, E. J.; Kim, B. G. Identification of the specific electron transfer proteins, ferredoxin, and ferredoxin reductase, for CYP105D7 in Streptomyces avermitilis MA4680. Appl. Microbiol. Biotechnol. 2014, doi: 10. 1007/s00253-014-5525-x.
85. Jung, S. T.; Lauchli, R.; Arnold, F. H. Cytochrome P450: Taming a wild type enzyme. Curr. Opin. Biotechnol. 2011, 22, 1-9.
86. Hlavica, P. Assembly of non-natural electron transfer conduits in the cytochrome P450 system: A critical assessment and update of artificial redox constructs amenable to exploitation in biotechnological areas. Biotechnol. Adv. 2009, 27, 103-121.
87. Chang, T. S.; Chao, S. Y.; Chen, Y. C. Production of ortho-hydroxydaidzein derivatives by a recombinant strain of Pichia pastoris harboring a cytochrome P450 fusion gene. Process Biochem. 2013, 48, 426-429.
88. Chang, T. S. Department of Biological Science and Technology. National University of Tainan. Unpublished observation. 2014.
89. Chang, T. S. Department of Biological Science and Technology. National University of Tainan. Unpublished observation. 2014.