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中国生物工程杂志

China Biotechnology
China Biotechnology
China Biotechnology  2020, Vol. 40 Issue (9): 62-68    DOI: 10.13523/j.cb.2004045
    
Advances in Biosynthesis of Phenyllactic Acid
DENG Ting-shan1,WU Guo-gan2,3,4,SUN Yu2,3,4,TANG Xue-ming2,3,4,***()
1 College of Food Science and Technology,Shanghai Ocean University,Shanghai 201306,China
2 Biotech Research Institute, Shanghai Academy of Agricultural Sciences,Shanghai 201106,China
3 Crops Ecological Environment Security Inspection and Supervision Center(Shanghai),Ministry of Agricultureand Rural Affairs,P.R.C., Shanghai 201106,China
4 Shanghai Academy of Agricultural Sciences,Key Laboratory of Agricultural Genetics and Breeding, Shanghai 201106,China
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Abstract  

Phenyllactic acid is a new biological preservative which is naturally nontoxic and has broad-spectrum bacteriostatic effect. It can be produced by a variety of different microorganisms, including most lactic acid bacteria. Phenyllactic acid is widely used, which can not only be used in food industry to inhibit a variety of pathogens, but also in medicine and chemical industry. The characteristics, applications and biosynthesis of phenyllactic acid were reviewed, in order to have a systematic understanding of phenyllactic acid and its biosynthesis.

Key words： Phenyllactic acid      Lactic acid bacteria      Biosynthesis     
Received: 22 April 2020      Published: 12 October 2020
ZTFLH:  Q819  
Corresponding Authors: Xue-ming TANG     E-mail: xueming70@foxmail.com
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Ting-shan DENG
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Xue-ming TANG
Cite this article:

DENG Ting-shan,WU Guo-gan,SUN Yu,TANG Xue-ming. Advances in Biosynthesis of Phenyllactic Acid. China Biotechnology, 2020, 40(9): 62-68.

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https://manu60.magtech.com.cn/biotech/10.13523/j.cb.2004045     OR     https://manu60.magtech.com.cn/biotech/Y2020/V40/I9/62

Fig.1 Structural formula of phenyllactic acid isomers
Strain Source YPLA(mg/L) Reference
Geotrichum candidum Cheese 600~1000 [10]
Propionibacterium DSMZ collection 1.0~15.1 [35]
Bacillus coagulans TQ33 Skimmed milk powder 726.1 [36]
Leuconostoc mesenteroides subsp. Sourdough and olive phylloplane 10.0~101.1 [37]
Lactobacillus plantarum strain 21B Sourdough breads 56.0 [34]
Lactobacillus ssp. SK007 Chinese pickle 91.0 [38]
L. plantarum A139 Biena collection 82.0 [39]
Table 1 A variety of strains that produce phenyllactic acid by their own metabolism
Fig.2 In vivo PLA synthesis pathway
Fig.3 Enzymatic synthesis of PLA
[1]   Shim S M, Seo S H, Lee Y, et al. Consumers’ knowledge and safety perceptions of food additives: evaluation on the effectiveness of transmitting information on preservatives. Food Cont, 2011,22(7):1054-1060.
[2]   黄晓冬, 庄勋, 仇梁林, 等. BHT 亚急性毒性及致肺巨噬细胞凋亡作用. 中国公共卫生, 2006,22(10):1216-1218.
[2]   Huang X D, Zhuang X, Qiu L L, et al. Apoptosis effect on pulmonary macrophage induced by butylhydroxytoluene under subacute toxic exposure in rats. Chinese Journal of Public Health, 2006,22(10):1216-1218.
[3]   赵俊杰. 生物防腐剂及其在食品防腐中的应用. 现代食品, 2018, (11):24-26.
[3]   Zhao J J. Biological preservatives and the application in food preservation. Modern Food, 2018,(11):24-26.
[4]   邓喜玲, 陈学敏, 周淑芳, 等. β-苯基乳酸的合成. 西北药学杂志, 2001,16(1):36-37.
[4]   Deng X L, Chen X M, Zhou S F, et al. Synthesis of β-phenyllactic acid. Northwest Pharmaceutical Journal, 2001,16(1):36-37.
[5]   Bubl E C, Butts J S. A method of synthesis of phenyllactic acid and substituted phenyllactic acids. Journal of the American Chemical Society, 1951,73(10):4972.
[6]   三菱人造丝株式会社. 苯基乳酸衍生物的生产方法: 中国,CN95109050.X. 2002-04-24[2020-08-19]. http://cprs.patentstar.com.cn/Search/Detail?ANE=9CAC9AHD9BHA9ICB9GBH2ACA9FDE9DHB.
[6]   Mitsubishi Rayon Co Ltd. Production methods of phenyllactic acid derivatives: China,CN95109050.X. 2002-04-24[2020-08-19]. http://cprs.patentstar.com.cn/Search/Detail?ANE=9CAC9AHD9BHA9ICB9GBH2ACA9FDE9DHB.
[7]   Nitto Chemical Industry Co Ltd. Process for production of phenyllactic acid derivative: US, US5684186A, 1997-11-04[2020-08-19]. http://pss-system.cnipa.gov.cn/sipopublicsearch/patentsearch/showViewList-jumpToView.shtml.
[8]   van Draanen N A, Hengst S. The conversion of L-phenylalanine to (S)-2-hydroxy-3-phenylpropanoic acid: a simple, visual example of a stereospecific SN2 reaction. Journal of Chemical Education, 2010,87(6):623-624.
doi: 10.1021/ed100167k
[9]   孙大庆, 李芬, 李洪飞. 苯乳酸微生物代谢研究进展. 农产品加工, 2018,(5):55-56,59.
[9]   Shun D Q, Li F, Li H F. Research progress of phenyllactic acid microbial metabolism. Farm Products Processing, 2018,(5):55-56,59.
[10]   Dieuleveux V V D P D, Chataud J, Gueguen M. Purification and characterization of anti-listeria compounds produced by Geotrichum candidum. Applied and Environmental Microbiology, 1998,64(2):800-803.
[11]   Gupta R K, Prasad D N. Antibiotic activity of Nisin in food preservation,. Microbiol Aliment Nutrit, 1989, (7):19-208.
[12]   Stevens K A, Sheldon B W, Klapes N A, et al. Nisin treatment for inactivation of Salmonella species and other gram-negative bacteria. Applied and Environmental Microbiology, 1991,57(12):3613-3615.
[13]   Ohhira I, Kuwaki S, Morita H, et al. Identification of 3-phenyllactic acid as a possible antibacterial substance produced by Enterococcus faecalis TH10. Biocontrol Science, 2010,9(3):77-81.
[14]   Lavermicocca P, Valerio F, Visconti A. Antifungal activity of phenyllactic acid against molds isolated from bakery products. Applied and Environmental Microbiology, 2003,69(1):634-640.
pmid: 12514051
[15]   韩德强, 丁宏标, 乔宇. 乳酸链球菌素的分子结构、抗菌活性及基因工程研究. 生物技术通报, 2005, (5):35-38.
[15]   Han D Q, Ding H B, Qiao Y. The molecular structure,antibiotic activties and genetic engineering of nisin. Biotechnology Bulletin, 2005,(5):35-38.
[16]   吕淑霞, 白泽朴, 代义, 等. 乳酸链球菌素(Nisin)抑菌作用及其抑菌机理的研究. 中国酿造, 2008,27(5):91-95.
[16]   Lu S X, Bei Z P, Dai Y, et al. Study of antibacterial function and mechanism of Nisin. China Brewing, 2008,27(5):91-95.
[17]   Punyauppapath S, Phumkhachorn P, Rattanachaikunsopon P. Nisin: production and mechanism of antimicrobial action. International Journal of Current Research & Review, 2015,7(2):47-53.
[18]   刘韵昕. 苯乳酸的抑菌活性及抑菌机理研究. 临汾:山西师范大学, 2017.
[18]   Liu Y X. Antibacterial activity and mechanism of action of phenyllactic acid. Linfen: Shanxi Normal University, 2017.
[19]   宁亚维, 闫爱红, 王世杰, 等. 苯乳酸与食品防腐剂联合抑菌效果. 食品与机械, 2017,33(9):117-120.
[19]   Ning Y W, Yan A H, Wang S J, et al. Study on antibacterial activity of phenyllactic acid combined with food preservatives. Food & Machinery, 2017,33(9):117-120.
[20]   Lavermicocca P, Valerio F A. Antifungal activity of phenyllactic acid against molds isolated from bakery products. Applied and Environmental Microbiology, 2003,69(1):634-640.
pmid: 12514051
[21]   Schnürer J, Magnusson J. Antifungal lactic acid bacteria as biopreservatives. Trends in Food Science & Technology, 2005,16(1):70-78.
[22]   Yanina B A, Graciela F D V, Luciana G C. Optimization of phenyllactic acid production by Pediococcus acidilactici, CRL 1753:Application of the formulated bio-preserver culture in bread. Biological Control, 2018,123:137-143.
[23]   Wang J P, Lee J H, Yoo J S, et al. Effects of phenyllactic acid on growth performance,intestinal microbiota, relative organ weight,blood characteristics,and meat quality of broiler chicks. Poultry Science, 2010,89(7):1549-1555.
pmid: 20548086
[24]   Wang J P, Yoo J S, Lee J H, et al. Effects of phenyllactic acid on growth performance,nutrientdigestibility, microbial shedding,and blood profile in pigs. Journal of Animal Science, 2009,87(10):3235-3243.
pmid: 19542505
[25]   Wang J P, Yoo J S, Lee J H, et al. Effects of phenyllactic acid on production performance,egg quality parameters,and blood characteristics in laying hens. Journal of Applied Poultry Research, 2009,18(2):203-209.
[26]   于晓倩, 张成林, 李晴, 等. 苯乳酸纳米粒保鲜膜对冷藏鲟鱼保鲜效果研究. 包装工程. 2020,41(9):17-22.
[26]   Yu X Q, Zhang C L, Li Q, et al. Study on the preservation effect of benzoate nanoparticles on frozen sturgeon fish. Packaging Engineering. 2020,41(9):17-22.
[27]   Fan W, Ren H, Wang Y, et al. Orthogonal array design for optimization of phenyllactic acid-sodium alginate blend coating and its effect on the browning and quality of minimally processed lily bulbs. Journal of the Science of Food & Agriculture, 2019,99(11):2835-2845.
[28]   Nguyen H D, Jin X, Kaneko D, et al. Syntheses of high molecular weight poly(L-phenyllactic acid)s by a direct polycondensation in the presence of stable lewis acid. Chemistry Letters, 2011,40(6):584-585.
doi: 10.1246/cl.2011.584
[29]   Sun H L, Chuai J, Wei H Q. Multi-functional organic gelator derived from phenyllactic acid for phenol removal and oil recovery, Journal of Hazardous Materials, 2019,366:46-53.
doi: 10.1016/j.jhazmat.2018.11.095
[30]   王庭芳, 郑莉萍, 张宁, 等. 丹参素衍生物的研究进展. 药学实践杂志, 2011,29(2):83-88.
[30]   Wang T F, Zhen L P, Zhang N, et al. Progress on Danshensu derivatives. Journal of Pharmaceutical Practice, 2011,29(2):83-88.
[31]   Urban F J, Moore B S. Synthesis of optically active 2-benzyldihydrobenzopyrans for the hypoglycemic agent englitazone. Cheminform, 2010,23(38):31-34.
[32]   Weckwerth W, Miyamoto K, Iinuma K, et al. Biosynthesis of PF1022A and related cyclooctadepsipeptides. Journal of Biological Chemistry, 2000,275(23):17909-17915.
doi: 10.1074/jbc.M001084200 pmid: 10751395
[33]   Kano S, Yuasa Y, Yokomatsu T, et al. Highly stereocontrolled synthesis of the four individual stereoisomers of statine. Cheminform, 1989,20(6):67-70.
[34]   Lavermicocca P, Valerio F, Evidente A, et al. Purification and characterization of novel antifungal compounds from the sourdough Lactobacillus plantarum strain 21B. Applied and Environmental Microbiology, 2000,66(9):4084-4090.
doi: 10.1128/aem.66.9.4084-4090.2000 pmid: 10966432
[35]   Lind H, Sjögren J, Gohil S, et al. Antifungal compounds from cultures of dairy propionibacteria type strains. FEMS Microbiology Letters, 2007,271(2):310-315.
pmid: 17456184
[36]   王海宽, 高雪芹, 张淑丽, 等. 底物对凝结芽孢杆菌TQ33产苯乳酸的影响. 天津科技大学学报, 2014,(6):11-15.
[36]   Wang H K, Gao X Q, Zhang S L, et al. Effect of substrates on the production of phenyllactic acid of Bacillus coagulans TQ33. Journal of Tianjin University of Science & Technology, 2014,(6):11-15.
[37]   Valerio F, Lavermicocca P, Pascale M, et al. Production of phenyllactic acid by lactic acid bacteria:an approach to the selection of strains contributing to food quality and preservation. FEMS Microbiology Letters, 2004,233(2):289-295.
doi: 10.1016/j.femsle.2004.02.020 pmid: 15063498
[38]   Li X F, Jiang B, Pan B L. Biotransformation of phenylpyruvic acid to phenyllactic acid by growing and resting cells of a Lactobacillus sp. Biotechnology Letters, 2007,29(4):593-597.
doi: 10.1007/s10529-006-9275-4 pmid: 17333468
[39]   Fernandez B, Vimont A, Desfossés-Foucault é, et al. Antifungal activity of lactic and propionic acid bacteria and their potential as protective culture in cottage cheese. Food Control, 2017,78:350-356.
[40]   李兴峰, 江波, 潘蓓蕾, 等. 苯丙氨酸及苯丙酮酸对Lactobacillus sp.SK007合成苯乳酸的影响. 过程工程学报, 2007,7(6):152-156.
[40]   Li X F, Jiang B, Pan B L, et al. Effects of phenylalanine and phenylpyruvic acid on biosynthesis of phenyllactic acid with Lactobacillus sp. SK007. Process Engineering, 2007,7(6):152-156.
[41]   芦夏霏, 刘毕琴, 柳陈坚, 等. 乳酸菌苯乳酸的合成及其代谢调控机制研究进展. 食品与发酵工业, 2014,40(11):177-181.
[41]   Lu X F, Liu B Q, Liu C J, et al. Progress in the synthesis of lactic acid bacteria and its metabolic regulation mechanism. Food and Fermentation Industries, 2014,40(11):177-181.
[42]   Xu G C, Zhang L L, Ni Y. Enzymatic preparation of D-phenyllactic acid at high space-time yield with a novel phenylpyruvate reductase identified from Lactobacillus sp. CGMCC 9967. Journal of Biotechnology, 2016,222:29-37.
pmid: 26712480
[43]   Amin M R, Onodera R. Synthesis of phenylalanine and production of other related compounds from phenylpyruvic acid and phenylacetic acid by ruminal bacteria, protozoa, and their mixture in vitro. Journal of General and Applied Microbiology, 1997,43(1):9-15.
doi: 10.2323/jgam.43.9 pmid: 12501348
[44]   Nicoline Vermeulen, Michael G.Gánzle, Rudi F. Vogel,influence of peptide supply and cosubstrates on phenylalanine metabolism of Lactobacillus sanfranciscensis DSM20451T and Lactobacillus plantarum TMW1.468. Journal of Agricultural and Food Chemistry, 2006,54(11):3832-3839.
pmid: 16719504
[45]   张建志. 代谢工程改造大肠杆菌、酪丁酸梭菌生产苯乳酸和正丁醇. 北京:中国农业大学, 2017.
[45]   Zhang J Z. Metabolic engineering of Escherichia coli, Clostridium tyrobutyricum for phenyllactic acid and n-butanol production. Beijing: China Agricultural University, 2017.
[46]   Zhao W R, Ding H R, Lv C J, et al. Two-step biocatalytic reaction using recombinant Escherichia coli cells for efficient production of phenyllactic acid from l-phenylalanine. Process Biochemistry, 2018,64:31-37.
[47]   Tamura Y, Ohkubo A, Iwai S, et al. Two forms of NAD-dependent D-mandelate dehydrogenase in Enterococcus faecalis IAM 10071. Applied & Environmental Microbiology, 2002,68(2):947-951.
doi: 10.1128/aem.68.2.947-951.2002 pmid: 11823242
[48]   Wada Y, Iwai S, Tamura Y, et al. A new family of D-2-hydroxyacid dehydrogenases that comprises D-mandelate dehydrogenases and 2-ketopantoate reductases. Bioscience Biotechnology and Biochemistry, 2008,72(4):1087-1094.
[49]   Yamamoto H, Mitsuhashi K, Kimoto N, et al. Robust NADH-regenerator: improved α-haloketone-resistant formate dehydrogenase, Appl Microbiol Biot, 2005,67:33-39.
doi: 10.1007/s00253-004-1728-x
[50]   Pham S Q, Gao P, Li Z. Engineering of recombinant E. coli cells co-expressing P450pyrTM monooxygenase and glucose dehydrogenase for highly regio- and stereoselective hydroxylation of alicycles with cofactor recycling, Biotechnol. Bioeng. 2013,110:363-373.
pmid: 22886996
[51]   郭明, 胡昌华 .生物转化: 从全细胞催化到代谢工程. 中国生物工程杂志, 2010,30(4):110-115.
[51]   Guo M, Hu C H. Biotransformation: from whole-cell catalysis to metabolic engineering. China Biotechnology, 2010,30(4):110-115.
[52]   Yibo Z, Ying W, Jiayuzi X, et al. Enantioselective biosynthesis of L-phenyllactic acid by whole cells of recombinant Escherichia coli. Molecules, 2017,22(11):1966.
[53]   王秀婷. 重组大肠杆菌全细胞转化L-苯丙氨酸合成苯乳酸的研究. 无锡:江南大学, 2018.
[53]   Wang X T. Study of biosynthesis of phenyllactic acid by recombinant E. coli whole-cell biotransformation of L-phenylalanine. Wuxi: Jiangnan University, 2018.
[54]   刘长建, 刘秋, 姜波, 等. 产苯乳酸乳酸菌的筛选鉴定. 食品工业科技, 2012,33(21):192-195.
[54]   Liu C J, Liu Q, Jiang B, et al. Isolation and identification of phenyllactic acid-producing LAB. Science and Technology of Food Industry, 2012,33(21):192-195.
[55]   Zhang X Q, Zhang S L, Shi Y, et al. A new high phenyllactic acid-yielding Lactobacillus plantarum IMAU10124 and a comparative analysis of lactate dehydrogenase gene. FEMS Microbiology Letters. 2014,356(1):89-96.
doi: 10.1111/1574-6968.12483 pmid: 24861375
[56]   李兴峰, 江波, 潘蓓蕾, 等. 产苯乳酸的乳酸菌分离筛选及菌种鉴定. 食品与发酵工业, 2007,32(2):1-4.
[56]   Li X F, Jiang B, Pan B L, et al. Screening and identification of phenyllactic acid-producing lactic acid bacteria. Food and Fermentation Industries, 2007,32(2):1-4.
[57]   柴虹宇, 张莉力, 王玉田. 苯乳酸高产菌株的诱变育种. 食品工业科技, 2010,31(8):154-156.
[57]   Chai H Y, Zhang L L, Wang Y T. Mutation and screening for the production of phenyllactic acid. Food and Technology of Food Industry, 2010,31(8):154-156.
[58]   刘晨, 张丽萍. 亚硝基胍-紫外复合诱变筛选高产苯乳酸菌株. 中国食品学报, 2015,15(9):41-46.
[58]   Liu C, Zhang L P. Screening of benzoic lactobacillus strains by mutagenesis of nitrosoguanidine - ultraviolet. Journal of Chinese Institute of Food Science and Technology, 2015,15(9):41-46.
[59]   Dao Y, Zhang K, Lu X, et al. Role of glucose and 2-oxoglutarate/malate translocator (omt1) in the production of phenyllactic acid and p-hydroxyphenyllactic acid, Two Food-Borne Pathogen Inhibitors. Agric Food Chem. 2019; 67(20):5820-5826.
[60]   Song X, Huang H, Xiong Z, et al. CRISPR-Cas9D10A nickase-assisted genome editing in Lactobacillus casei. Applied and Environmental Microbiology, 2017,83(22):1259-1276.
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