Metabolic engineering of Yarrowia lipolytica for liquiritigenin production

Chemical Engineering Science - Tập 230 - Trang 116177 - 2021
Muhammad Akram1, Aamir Rasool1, Ting An1, Xudong Feng1, Chun Li1,2,3
1Institute of Biochemical Engineering, Department of Chemical Engineering, School of Chemistry and Chemical Engineering, Beijing Institute of Technology, Beijing 100081, China
2Key Lab for Industrial Biocatalysis, Ministry of Education, Department of Chemical Engineering, Tsinghua University, Beijing 100084, China
3Center for Synthetic & Systems Biology, Tsinghua University, Beijing 100084, China

Tài liệu tham khảo

Akashi, 1997, Anthocyanin-producing dandelion callus as a chalcone synthase source in recombinant polyketide reductase assay, Phytochemistry, 46, 283, 10.1016/S0031-9422(97)00298-7 Andersen, 2007, High levels of linkage disequilibrium and associations with forage quality at a phenylalanine ammonia Lyase locus in European maize (Zea mays L.) inbreds, Theor. Appl. Genet., 114, 307, 10.1007/s00122-006-0434-8 Baba, 2000, Saponins isolated from Allium chinense G. DON and antitumor-promoting activities of isoliquiritigenin and laxogenin from the same drug, Biol. Pharm. Bull., 23, 660, 10.1248/bpb.23.660 Ballance, 1995, Medicago sativa cDNAs encoding chalcone reductase, Plant Physiol., 107, 1027, 10.1104/pp.107.3.1027 Blazeck, 2015, Metabolic engineering of Yarrowia lipolytica for itaconic acid production, Metab. Eng., 32, 66, 10.1016/j.ymben.2015.09.005 Cochrane, 2004, The Arabidopsis phenylalanine ammonia lyase gene family: Kinetic characterization of the four PAL isoforms, Phytochemistry, 65, 1557, 10.1016/j.phytochem.2004.05.006 Cui, 2014, Biotechnological production and applications of microbial phenylalanine ammonia lyase: A recent review, Crit. Rev. Biotechnol., 34, 258, 10.3109/07388551.2013.791660 Druka, 2003, Chalcone isomerase gene from rice (Oryza sativa) and barley (Hordeum vulgare): Physical, genetic and mutation mapping, Gene, 302, 171, 10.1016/S0378-1119(02)01105-8 Dulermo, 2017, Using a vector pool containing variable-strength promoters to optimize protein production in Yarrowia lipolytica, Microb. Cell Fact., 16, 31, 10.1186/s12934-017-0647-3 Ehlting, 1999, Three 4-coumarate:coenzyme A ligases in Arabidopsis thaliana represent two evolutionarily divergent classes in angiosperms, Plant J., 19, 9, 10.1046/j.1365-313X.1999.00491.x Ekiert, 2012, Possibilities of arbutin production using plant biotechnology methods, Pol. J. Cosmetol., 15, 151 Feinbaum, 1988, Transcriptional regulation of the Arabidopsis thaliana chalcone synthase gene, Mol. Cell. Biol., 8, 1985, 10.1128/MCB.8.5.1985 Ferrer, 1999, Structure of chalcone synthase and the molecular basis of plant polyketide biosynthesis, Nat. Struct. Biol., 6, 775, 10.1038/11553 Frank, 1991, Sequence and structure of a phenylalanine ammonia lyase gene from Glycine max, Mitochondrial DNA, 1, 335 Franken, 1991, The duplicated chalcone synthase genes C2 and Whp (white pollen) of Zea mays are independently regulated; evidence for translational control of Whp expression by the anthocyanin intensifying gene in, EMBO J., 10, 2605, 10.1002/j.1460-2075.1991.tb07802.x Furuya, 2012, Biotechnological production of caffeic acid by bacterial cytochrome P450 CYP199A2, Appl. Environ. Microbiol., 78, 6087, 10.1128/AEM.01103-12 Gan, 2010, Simultaneous determination of eight major constituents in the traditional Chinese medicine Shaoyao-Gancao - Tang by UPLC-PDA, J. Med. Plants Res., 4, 2615 Gao, 2020, Efficient Biosynthesis of (2 S)-Naringenin from p-Coumaric Acid in Saccharomyces cerevisiae, J. Agric. Food Chem., 68, 1015, 10.1021/acs.jafc.9b05218 Gao, 2017, Iterative integration of multiple-copy pathway genes in Yarrowia lipolytica for heterologous β-carotene production, Metab. Eng., 41, 192, 10.1016/j.ymben.2017.04.004 Gaur, 2014, In vivo anti-diabetic activity of derivatives of isoliquiritigenin and liquiritigenin, Phytomedicine, 21, 415, 10.1016/j.phymed.2013.10.015 Grotewold, 1994, Isolation and characterization of a maize gene encoding chalcone flavonone isomerase, Mol. Gen. Genet., 242, 1, 10.1007/BF00277341 Gui, 2011, Functional characterization of evolutionarily divergent 4-coumarate: Coenzyme A ligases in rice, Plant Physiol., 157, 574, 10.1104/pp.111.178301 Hajirahimkhan, 2013, Evaluation of Estrogenic Activity of Licorice Species in Comparison with Hops Used in Botanicals for Menopausal Symptoms, PLoS One, 8, 10.1371/journal.pone.0067947 Hamberger, 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, 10.1073/pnas.0307307101 Hong, 2011, Phytoestrogenic compounds in alfalfa sprout (Medicago sativa) beyond coumestrol, J. Agric. Food Chem., 59, 131, 10.1021/jf102997p Hu, 2010, Synthesis and antitumor activity of liquiritigenin thiosemicarbazone derivatives, Eur. J. Med. Chem., 45, 3453, 10.1016/j.ejmech.2010.04.036 Jez, 2000, Dissection of malonyl-coenzyme A decarboxylation from polyketide formation in the reaction mechanism of a plant polyketide synthase, Biochemistry, 39, 890, 10.1021/bi991489f Jiao, Y.S., Zhao, Y., Chen, W.F., 2018. Duplications and functional specialization force distinct evolution of isoflavonoid biosynthetic genes in legumes. bioRxiv 361386. Kallscheuer, 2016, Construction of a Corynebacterium glutamicum platform strain for the production of stilbenes and (2S)-flavanones, Metab. Eng., 38, 47, 10.1016/j.ymben.2016.06.003 Kaneko, 2003, Cinnamate:coenzyme A ligase from the filamentous bacterium Streptomyces coelicolor A3(2), J. Bacteriol., 185, 20, 10.1128/JB.185.1.20-27.2003 Khamsan, S., Liawruangrath, S., Teerawutkulrag, A., Pyne, S., Garson, M., Liawruangrath, B., 2012. The isolation of bioactive flavonoids from Jacaranda obtusifolia H. B. K. ssp. rhombifolia (G. F. W. Meijer) Gentry. Acta Pharm. 62 (2), 181-190. Kim, 2014, Biosynthesis of pinocembrin from glucose using engineered Escherichia coli, J. Microbiol. Biotechnol., 24, 1536, 10.4014/jmb.1406.06011 Kim, 2004, Cytoprotective effects of Glycyrrhizae radix extract and its active component liquiritigenin against cadmium-induced toxicity (effects on bad translocation and cytochrome c-mediated PARP cleavage), Toxicology, 197, 239, 10.1016/j.tox.2004.01.010 Kim, 2008, Anti-inflammatory effects of liquiritigenin as a consequence of the inhibition of NF-κB-dependent iNOS and proinflammatory cytokines production, Brazilian J. Pharmacogn., 154, 165 Kuittinen, 2000, Nucleotide variation at the chalcone isomerase locus in Arabidopsis thaliana, Genetics, 155, 863, 10.1093/genetics/155.2.863 Leonard, 2006, Expression of a soluble flavone synthase allows the biosynthesis of phytoestrogen derivatives in Escherichia coli, Appl. Microbiol. Biotechnol., 70, 85, 10.1007/s00253-005-0059-x Li, Yan, Xi, Y., Zhongkai, Huang, X., Li, Y., 2001. Co-suppression in transgenic Petunia hybrida expressing chalcone synthase A (CHSA). Sci. China, Ser. C Life Sci. 44 (6), 661-668. Li, 2017, Engineering Yarrowia lipolytica for poly-3-hydroxybutyrate production, J. Ind. Microbiol. Biotechnol., 44, 605, 10.1007/s10295-016-1864-1 Liu, 2019, Engineering acetyl-CoA metabolic shortcut for eco-friendly production of polyketides triacetic acid lactone in Yarrowia lipolytica, Metab. Eng., 56, 60, 10.1016/j.ymben.2019.08.017 Liu, 2015, Overexpression of artificially fused bifunctional enzyme 4CL1-CCR: A method for production of secreted 4-hydroxycinnamaldehydes in Escherichia coli, Microb. Cell Fact., 14, 118, 10.1186/s12934-015-0309-2 Liu, 2016, Construction of CHI gene expression vector of safflower and its transformation in Arabidopsis thaliana, Chinese Tradit. Herb. Drugs, 47, 3279 Lv, 2019, Optimizing oleaginous yeast cell factories for flavonoids and hydroxylated flavonoids biosynthesis, ACS Synth. Biol., 8, 2514, 10.1021/acssynbio.9b00193 Mameda, 2018, Involvement of chalcone reductase in the soybean isoflavone metabolon: identification of GmCHR5, which interacts with 2-hydroxyisoflavanone synthase, Plant J., 96, 56, 10.1111/tpj.14014 Markham, 2018, Synthetic Biology Expands the Industrial Potential of Yarrowia lipolytica, Trends Biotechnol., 36, 1085, 10.1016/j.tibtech.2018.05.004 Martinez, 2013, 2013 Matsumoto, 2005, The map-based sequence of the rice genome, Nature., 436, 793, 10.1038/nature03895 McKhann, 1994, Isolation of chalcone synthase and chalcone isomerase cDNAs from alfalfa (Medicago sativa L.): highest transcript levels occur in young roots and root tips, Plant Mol. Biol., 24, 767, 10.1007/BF00029858 Mersereau, 2008, Liquiritigenin is a plant-derived highly selective estrogen receptor β agonist, Mol. Cell. Endocrinol., 283, 49, 10.1016/j.mce.2007.11.020 Minami, 1989, Structure and some characterization of the gene for phenylalanine ammonia lyase from rice plants, Eur. J. Biochem., 185, 19, 10.1111/j.1432-1033.1989.tb15075.x Miyahisa, 2005, Efficient production of (2S)-flavanones by Escherichia coli containing an artificial biosynthetic gene cluster, Appl. Microbiol. Biotechnol., 68, 498, 10.1007/s00253-005-1916-3 Muhammad, 2020, Production of plant natural products through engineered Yarrowia lipolytica, Biotechnol. Adv., 43, 107555, 10.1016/j.biotechadv.2020.107555 Palmer, 2020, Engineering 4-coumaroyl-CoA derived polyketide production in Yarrowia lipolytica through a β-oxidation mediated strategy, Metab. Eng., 57, 174, 10.1016/j.ymben.2019.11.006 Rodrigues, 2015, Heterologous production of caffeic acid from tyrosine in Escherichia coli, Enzyme Microb. Technol., 71, 36, 10.1016/j.enzmictec.2015.01.001 Rodriguez, 2015, Establishment of a yeast platform strain for production of p-coumaric acid through metabolic engineering of aromatic amino acid biosynthesis, Metab. Eng., 31, 10.1016/j.ymben.2015.08.003 Rodriguez, 2017, Metabolic engineering of yeast for fermentative production of flavonoids, Bioresour. Technol., 245, 1645, 10.1016/j.biortech.2017.06.043 Sallaud, 1995, Nucleotide sequences of three chalcone reductase genes from alfalfa, Plant Physiol., 108, 869, 10.1104/pp.108.2.869 Santos, 2010 Santos, 2011, Optimization of a heterologous pathway for the production of flavonoids from glucose, Metab. Eng., 13, 392, 10.1016/j.ymben.2011.02.002 Sayre, 2013, Chiral analytical method development of liquiritigenin with application to a pharmacokinetic study, Biomed. Chromatogr., 27, 404 Schmutz, 2010, Genome sequence of the palaeopolyploid soybean, Nature., 463, 178, 10.1038/nature08670 Shabbir Hussain, 2016, Engineering Promoter Architecture in Oleaginous Yeast Yarrowia lipolytica, ACS Synth. Biol., 5, 213, 10.1021/acssynbio.5b00100 Shimomura, M., Kanamori, H., Komatsu, S., Namiki, N., Mukai, Y., Kurita, K., Kamatsuki, K., Ikawa, H., Yano, R., Ishimoto, M., Kaga, A., Katayose, Y., 2015. The Glycine max cv. Enrei Genome for Improvement of Japanese Soybean Cultivars. Int. J. Genomics 2015. Spagnuolo, 2018, Alternative substrate metabolism in Yarrowia lipolytica, Front. Microbiol., 9, 1077, 10.3389/fmicb.2018.01077 Stahlhut, 2015, Assembly of a novel biosynthetic pathway for production of the plant flavonoid fisetin in Escherichia coli, Metab. Eng., 31, 84, 10.1016/j.ymben.2015.07.002 Verde, 2013, The high-quality draft genome of peach (Prunus persica) identifies unique patterns of genetic diversity, domestication and genome evolution, Nat. Genet., 45, 487, 10.1038/ng.2586 Wei, 2003, Studies on chemical constituents from the root of Mirablis jalapa, Zhongguo Zhongyao Zazhi, 28, 1151 Welle, 1991, Induced plant responses to pathogen attack: Analysis and heterologous expression of the key enzyme in the biosynthesis of phytoalexins in soybean (Glycine max L. Merr. cv. Harosoy 63), Eur. J. Biochem., 196, 423, 10.1111/j.1432-1033.1991.tb15833.x Wong, 2017, YaliBricks, a versatile genetic toolkit for streamlined and rapid pathway engineering in Yarrowia lipolytica, Metab. Eng. Commun., 5, 68, 10.1016/j.meteno.2017.09.001 Wu, 2014, Modular optimization of heterologous pathways for de Novo synthesis of (2S)-Naringenin in Escherichia coli, PLoS One, 9, e101492, 10.1371/journal.pone.0101492 Yan, 2007, Biosynthesis of 5-deoxyflavanones in microorganisms, Biotechnol. J., 2, 1250, 10.1002/biot.200700119 Yi, 2010, Differential expression of CHS7 and CHS8 genes in soybean, Planta., 231, 741, 10.1007/s00425-009-1079-z Yin, 2019, The Research Progress of Chalcone Isomerase (CHI) in Plants, Mol. Biotechnol., 61, 32, 10.1007/s12033-018-0130-3 Yu, 2015, Anti-inflammatory activities of licorice extract and its active compounds, glycyrrhizic acid, liquiritin and liquiritigenin, in BV2 cells and mice liver, Molecules, 20, 13041, 10.3390/molecules200713041 Zhang, 2004, GC-MS Determination of Flavonoids and Phenolic and Benzoic Acids in Human Plasma after Consumption of Cranberry Juice, J. Agric. Food Chem., 52, 222, 10.1021/jf035073r Zhou, 2019, Fine-tuning the (2S)-naringenin synthetic pathway using an iterative high-throughput balancing strategy, Biotechnol. Bioeng., 116, 1392, 10.1002/bit.26941