Current Status of Microbial Phenylethanoid Biosynthesis
1
조회
0
다운로드
1
인용
0
참고문헌
키워드
초록
Phenylethanoids, including 2-phenylethanol, tyrosol, and salidroside are a group of phenolic compounds with a C6-C2 carbon skeleton synthesized by plants. Phenylethanoids display a variety of biological activities, including antibacterial, anticancer, anti-inflammatory, neuroprotective, and anti-asthmatic activities. Recently, successful microbial synthesis of phenylethanoids through metabolic engineering and synthetic biology approaches has been reported and could allow phenylethanoid production from alternative microbial sources. Here, we review the recent achievements in the synthesis of phenylethanoids by microorganisms. The work done so far will contribute to the production of diverse phenylethanoids using various microbial systems and facilitate exploration of further diverse biological activities of phenylethanoids.
Abstract
Phenylethanoids, including 2-phenylethanol, tyrosol, and salidroside are a group of phenolic compounds with a C6-C2 carbon skeleton synthesized by plants. Phenylethanoids display a variety of biological activities, including antibacterial, anticancer, anti-inflammatory, neuroprotective, and anti-asthmatic activities. Recently, successful microbial synthesis of phenylethanoids through metabolic engineering and synthetic biology approaches has been reported and could allow phenylethanoid production from alternative microbial sources. Here, we review the recent achievements in the synthesis of phenylethanoids by microorganisms. The work done so far will contribute to the production of diverse phenylethanoids using various microbial systems and facilitate exploration of further diverse biological activities of phenylethanoids.
참고문헌 (57)
- Vogt T, "Phenylpropanoid biosynthesis", Mol. Plant., 3, pp.2~20 (2013)
- Vermerris W, "Families of phenolic compounds and means of classification. In Phenolic compound biochemistry", pp.1~34 (2008), Springer
- Kobayashi S, "Enzymatic polymer synthesis: an opportunity for green polymer chemistry", Chem. Rev., 109, pp.5288~5353 (2009)[DOI]
- Cheynier V, "Phenolic compounds: from plants to foods", Phytochem. Rev., 11, pp.153~177 (2012)[DOI]
- Hollman PCH, "Evidence for health benefits of plant phenols: local or systemic effects?", J. Sci. Food Agric., 81, pp.842~852 (2001)[DOI]
- Kumar S, "Chemistry and biological activity of flavonoids: an overview", Sci. World J., 2013, pp.1627504~ (2013)
- Cheynier V, "Phenolic compounds: from plants to foods", Phytochem. Rev., 11, pp.153~177 (2012)[DOI]
- Agrawal AD, "Pharmacological activities of flavonoids: a review", Int. J. Pharm. Sci. Nanotech., 4, pp.1394~1398 (2011)
- Rimando AM, "Biological", chemopreventive activity of stilbenes and their effect on colon cancer, 2008, pp.74, 1635~1643
- Fu G, "Naturally occurring phenylethanoid glycosides: potential leads for new theraperutics", Cur. Med. Chem., 15, pp.2592~2613 (2008)[DOI]
- Xue Z, "Phenylethanoid glycosides: research advances in their phytochemistry, pharmacological activity and pharmacokinetics", Molecules, 21, pp.991~ (2016)[DOI]
- Cifani C, "Effect of salidroside, active principle of Rhodiolarosea extract, on binge eating", Physiol. Behav., 101, pp.555~562 (2010)[DOI]
- Viuda-Martos M, "Functional properties of honey, propolis and royal jelly", J. Food Sci., 73, pp.R117~R124 (2008)[DOI]
- Piroddi M, "Nutrigenomics of extra-virgin olive oil: a review", Biofactors, 43, pp.17~41 (2017)[DOI]
- St-Laurent-Thibault C, "Tyrosol and hydroxytyrosol, two main components of olive oil, protect N2a cells against amyloid-<TEX>${\beta}$<", TEX>-induced toxicity. Involvement of the NF-<TEX>$\kappa$<, Curr. AlzheimerRes., pp.2011, 8[DOI]
- Ristagno G, "Hydroxytyrosolattenuates peripheral neuropathy in streptozotocin-induced diabetes in rats", J. Agric. Food Chem., 60, pp.5859~5865 (2012)[DOI]
- Tripoli E, "The phenolic compounds of olive oil: structure, biological activity and beneficial effects on human health", Nutr. Res. Rev., 18, pp.98~112 (2005)[DOI]
- Vilaplana-Perez C, "Hydroxytyrosol and potential uses in cardiovascular diseases, cancer, and AIDS", Front. Nutr., 1, pp.18~ (2014)
- Palumbo DR, "Rhodiolarosea extract protects human cortical neurons against glutamate and hydrogen peroxide-induced cell death through reduction in the accumulation of intracellular calcium", Phytother. Res., 26, pp.878~883 (2012)[DOI]
- Zhang JK, "Protection by salidroside against bone loss via inhibition of oxidative stress and bone-resorbing mediators", PLoS One, 8, pp.e57251~ (2013)[DOI]
- Zhang H, "Protective effects of salidroside on epirubicin-induced early left ventricular regional systolic dysfunction in patients with breast cancer", Drugs R. D., 12, pp.101106~ (2012)
- Huang M-T, "Inhibitory effects of caffeic acid phenethyl ester (CAPE) on12-0-tetradecanoylphorbol-13-acetate-induced tumor promotion inmouse skin and the synthesis of DNA, RNA and protein in HeL", Carcinogcnesis, 17, pp.761~765 (1996)[DOI]
- Murtaza G, "Caffeic acid phenethyl ester and therapeutic potentials", BioMed Res. Int., 2014, pp.145342~ (2014)
- Boudreau LH, "Caffeic acid phenethyl ester and its amide analogue are potent inhibitors of leukotriene biosynthesis in human polymorphonuclear leukocytes", PLoS One, 7, pp.e31833~ (2012)[DOI]
- Son S, "Caffeic acid phenethyl ester (CAPE): synthesis and X-ray crystallographic analysis", Chem. Pharm. Bull., 49, pp.236~238 (2001)[DOI]
- Shi H, "Synthesis of caffeic acid phenethyl ester derivatives, and their cytoprotective and neuritogenic activities in PC12 cells", J. Agric. Food Chem., 62, pp.5046~5053 (2014)[DOI]
- Zhang P, "Bioactivity and chemical synthesis of caffeic acid phenethyl ester and its derivatives", Molecules, 19, pp.16458~16476 (2014)[DOI]
- Hua D, "Recent advances in biotechnological production of 2-phenylethanol", Biotechnol. Adv., 29, pp.654~660 (2011)[DOI]
- Kim T-Y, "Biosynthesis of 2- phenylethanol from glucose with genetically engineered Kluyveomycesmarxianus", Enzyme Microbial. Technol., 61-62, pp.44~47 (2014)[DOI]
- Ma LQ, "Molecular cloning and overexpression of a novel UDP-glucosyltransferase elevating salidroside levels in Rhodiolasachalinensis", Plant Cell Rep., 26, pp.989~999 (2007)[DOI]
- Kaminaga Y, "Plant phenylacetaldehyde synthase is a bifunctional homotetrameric enzyme that catalyzes phenylalanine decarboxylation and oxidation", J. Biol. Chem., 281, pp.23357~23366 (2006)[DOI]
- Torrens-Spence M, "Biochemical evaluation of a parsley tyrosine decarboxylase results in a novel 4-hydroxyphenylacetaldehyde synthase enzyme", Biochem. Biophys. Res. Commun., 418, pp.211~216 (2012)[DOI]
- Torrens-Spence M, "Biochemical evaluation of the decarboxylationdeamination activities of plant aromatic amino acid decarboxylase", J. Biol. Chem., 288, pp.2376~2387 (2013)[DOI]
- Lester G, "Inhibition of growth, synthesis, and permeability in Neurospora crassa byphenethyl alcohol", J. Bacteriol., 90, pp.29~37 (1965)
- Huang C J, "Production and molar yield of 2-phenylethanol by Pichia fermentans L-5 as affected by some medium components", J. Biosci. Bioeng., 90, pp.142~147 (2000)[DOI]
- Chung H Jr, "Production and molar yield of 2-phenylethanol by Pichia fermentans L-5 as affected by some medium components", J. Biosci. Bioeng., 90, pp.142~147 (2000)[DOI]
- Kim B, "Metabolic engineering of Saccharomyces cerevisiae for the production of 2-phenylethanol via Ehrlich pathway", Biotechnol. Bioeng., 111, pp.115~124 (2013)
- Rodriguez A, "Engineering Escherichia coli to overproduce aromatic amino acids and derived compounds", Microb. Cell Fact., 13, pp.126~ (2014)
- Ikeda M, "Towards bacterial strains overproducing L-tryptophan and other aromatics by metabolic engineering", Appl. Microbiol. Biotechnol., 69, pp.615~626 (2006)[DOI]
- Lutke-Eversloh T, "L-Tyrosine production by deregulated strains of Escherichia coli", Appl. Microbiol. Biotechnol., 75, pp.103~110 (2007)[DOI]
- Sprenger GA, "From scratch value; engineering Escherichia coli wild type cells to the production of L-phenylalanine and other fine chemicals derived from chorismite", Appl. Microbial. Biotechnol., 75, pp.1628~1634 (2007)
- Kang Z, "Metabolic engineering of Escherichia coli for production of 2-phenylethanol from renewable glucose", Appl. Biochem. Biotechnol., 172, pp.2012~2021 (2013)
- Satoh Y, "Engineering of L-tyrosine oxidation in Escherichia coli and microbial production of hydroxytyrosol", Met. Eng., 14, pp.603~610 (2012)[DOI]
- Xue Y, "Engineering Escherichia coli for enhanced tyrosol production", J. Agric. Food Chem., 65, pp.4708~4714 (2017)[DOI]
- Chung D, "Production of three phenylethanoids, tyrosol, hydroxytyrosol, and salidroside, using plant genes expressing in Escherichia coli", Sci. Rep., 7, pp.2578~ (2017)[DOI]
- Bai Y, "Production of salidroside in metabolically engineered Escherichia coli", Sci. Rep., 4, pp.6640~ (2014)
- Wei T, "Genome engineering Escherichia coli for L-DOPA overproduction from glucose", Sci. Rep., 6, pp.30080~ (2016)[DOI]
- Eudes A, "Production of hydroxycinnamoyl anthranilates from glucose in Escherichia coli", Microb. Cell Fact., 12, pp.62~ (2013)[DOI]
- 안대균, "Bacterial synthesis of four hydroxycinnamic acids", Applied Biological Chemistry, 59(2), pp.173~179 (2016), 한국응용생명화학회
- 추혜정, "Microbial synthesis of hydroxytyrosol and hydroxysalidroside", Applied Biological Chemistry, 61(3), pp.295~301 (2018), 한국응용생명화학회
- Yu HS, "Characterization of glycosyltransferases responsible for salidroside biosynthesis in Rhodiolasachalinensis", Phytochemistry, 72, pp.862~870 (2011)[DOI]
- Fan B, "Mining of efficient microbial UDP-glycosyltransferases by motif evolution cross plant kingdom for application in biosynthesis of salidroside", Sci. Rep., 7, pp.463~ (2017)[DOI]
- Berner M, "Genes and enzymes involved in caffeic acid biosynthesis in the actinomycete Saccharothrixespanaensis", J. Bacteriol., 188, pp.2666~2673 (2006)[DOI]
- Jendresen CB, "Highly active and specific tyrosine ammonia-lyases from diverse origins enable enhanced production of aromatic compounds in bacteria and Saccharomyces cerevisiae", Appl. Environ. Microbiol., 81, pp.4458~4476 (2015)[DOI]
- Schoch G, "CYP98A3 from Arabidopsis thaliana is a 3'-hydroxylase of phenolic esters, a missing link in the phenylpropanoid pathway", J. Biol. Chem., 276, pp.36566~36574 (2001)[DOI]
- Widjaja A, "Enzymatic synthesis of caffeic acid phenethyl ester", J. Chin. Inst. Chem. Eng., 39, pp.13~418 (2008)[DOI]
- Wang J, "Engineering a bacterial platform for total biosynthesis of caffeic acid derived phenethyl esters and amides", Met. Eng., 44, pp.89~99 (2017)[DOI]
