氧化葡萄糖酸杆菌生物制造吡咯喹啉醌进展
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摘要
吡咯喹啉醌(PQQ)是继黄素核苷酸和吡啶核苷酸之后,在膜束缚的细菌脱氢酶中发现的第三种辅基,具有抗氧化、抗病毒和提高免疫力等多种生理功能,在食品、医药及农业等行业具有广泛的应用前景。该文综述了氧化葡萄糖酸杆菌(Gluconobacter oxydans)中PQQ的生理作用及生物合成的分子机制,表明了氧化葡萄糖酸杆菌作为出发菌株生产PQQ具有潜在优势,对今后工业化生产PQQ具有积极的指导意义。
Pyrroloquinoline quinone(PQQ), a third prosthetic group, was found in membrane-bound bacterial dehydrogenase following riboflavin and pyridine nucleotide. It was wildly used in food, medicine and agriculture industry for its various physiological functions, such as antioxidant,anti-virus and immune function. In this article, the physiological role and molecular mechanism of biosynthesis of PQQ in Gluconobacter oxydans were reviewed. Results showed that G. oxydans had the potential advantages for PQQ production. Hence, it has positive guidance significance for the future PQQ industrial production.
Pyrroloquinoline quinone(PQQ), a third prosthetic group, was found in membrane-bound bacterial dehydrogenase following riboflavin and pyridine nucleotide. It was wildly used in food, medicine and agriculture industry for its various physiological functions, such as antioxidant,anti-virus and immune function. In this article, the physiological role and molecular mechanism of biosynthesis of PQQ in Gluconobacter oxydans were reviewed. Results showed that G. oxydans had the potential advantages for PQQ production. Hence, it has positive guidance significance for the future PQQ industrial production.
引文
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[21]唐靓,张岭,李林子,等.吡咯喹啉醌研究新进展[J].食品科学,2015,36(19):287-291.
[22]GUO Z,MURPHY L,STEIN V,et al.Engineered PQQ-glucose dehydrogenase as a universal biosensor platform[J].J Am Chem Soc,2016,138(32):10108-10111.
[23]司振军.微生物高效生产吡咯喹啉醌和聚苹果酸的研究[D].杭州:浙江大学,2017.
[24]王朝绚.吡咯喹啉醌工程菌构建及关键基因研究[D].北京:北京化工大学,2013.
[25]PRUST C,HOFFMEISTER M,LIESEGANG H,et al.Complete genome sequence of the acetic acid bacterium Gluconobacter oxydans[J].Nature Biotechnol,2005,23:195-200.
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[27]KLEEF M A,DUINE J A.L-tyrosine is the precursor of PQQ biosynthesis in Hyphomicrobium X[J].FEBS Lett,1988,237:91-97.
[28]SHEN Y Q,BONNOT F,IMSAND E M,et al.Distribution and properties of the genes encoding the biosynthesis of the bacterial cofactor,pyrroloquinoline quinone[J].Biochem,2012,51(11):2265-2275.
[29]VELTEROP J S,SELLINK E,MEULENBERG J J,et al.Synthesis of pyrroloquinoline quinone in vivo and in vitro and detection of an intermediate in the biosynthetic pathway[J].J Bacteriol,1995,177:5088-5098.
[30]MEYER J B,FRAPOLLI M,KEEL C,et al.Pyrroloquinoline quinone biosynthesis gene pqq C,a novel molecular marker for studying the phylogeny and diversity of phosphate-solubilizing pseudomonads[J].Appl Environ Microbiol,2011,77(20):7345-7354.
[31]HOUCK D R,HANNERS J L,UNKEFER C C.Biosynthesis of pyrroloquinoline quinine.Identification of biosynthetic precursors using13Clabeling and NMR spectroscopy[J].J Am Chem Soc,1988,110:6020-6021.
[32]MAGNUSSON O T,TOYAMA H,SAEKI M,et al.Quinone biogenesis:Structure and mechanism of PqqC,the final catalyst in the production of pyrroloquinoline quinone[J].P Natl Acad Sci USA,2004,101(21):7913-7918.
[33]PUEHRINGER S,METLITZKY M,SCHWARZENBACHER R.The pyrroloquinoline quinone biosynthesis pathway revisited:A structural approach[J].BMC Biochem,2008,9:8-17.
[34]GAO L L,HU Y D,LIU J,et al.Stepwise metabolic engineering of Gluconobacter oxydans WSH-003 for the direct production of 2-keto-L-gulonic acid from D-sorbitol[J].Metab Eng,2014,24:30-37.
[35]YUAN J F,WU M B,LIN J P,et al.Combinatorial metabolic engineering of industrial Gluconobacter oxydans DSM2343 for boosting 5-ketoD-gluconic acid accumulation[J].BMC Biotechnol,2016,16(1):42.
[36]孙继国.利用不同启动子在大肠杆菌与肺炎克雷伯氏中合成PQQ的研究[D].北京:北京化工大学,2013.
[37]李盼盼.氧化葡萄糖酸杆菌合成吡咯喹啉醌的研究[D].郑州:郑州轻工业学院,2016.
[38]MEULENBERG J J M,SELLINK E,RIEGMAN N H,et al.Nucleotide sequence and structure of the Klebsiella pneumoniae pqq operon[J].Mol General Genetics Mgg,1992,232(2):284-294.
[39]URAKAMI T,YASHIMA K,KOBAYASHI H,et al.Production of pyrroloquinoline quinone by using methanol-utilizing bacteria[J].%Appl Environ Microbiol,1992,58(12):3970-3976.
[40]杨诗颖,陈佳,柯崇榕,等.吡咯喹啉醌产生菌的筛选及其培养基优化[J].药物生物技术,2014(5):429-432.
[41]钟杉杉.吡咯喹啉醌高产菌的筛选、诱变、发酵及基因克隆[D].北京:北京化工大学,2013.
[42]郑璞,姚红涛.一种甲基营养菌及其发酵生产吡咯喹啉醌的方法:CN201410087026.4[P].2014-07-02.
[43]XIONG X H,ZHAO Y,GE X,et al.Production and radioprotective effects of pyrroloquinoline quinone[J].Int J Mol Sci,2011,12(12):8913-8923.
[2]YASUSHISA N,TAKESHI K,ISAMU K,et al.Effects of pyrroloquinoline quinone(PQQ)and PQQ-oxazole on DNA synthesis[J].Life Sci,1993,52:1909-1915.
[3]AMEYAMA M,SHINAGAWA E,MATSUSHITA K,et al.Growth stimulating activity for microorganisms in naturally occurring substances and partial characterization of the substance for the activity as pyrroloquinoline quinone[J].Agr Biol Chem,1985,49:699-709.
[4]KUMAZAWA T,SATO K,SENO H,et al.Levels of pyrroloquinoline quinone in various foods[J].Biochem J,1995,307(2):331-333.
[5]STEINBERG F,STITES T E,ANDERSON P,et al.Pyrroloquinoline quinone improves growth and reproductive performance in mice fed chemically defined diets[J].Exp Biol Med,2003,228(2):160-166.
[6]KUMAZAWA T,SENO H,URAKAMI T,et al.Trace levels of pyrroloquinoline quinone in human and rat samples edteceted by gas chromatoraphy/mass spectrometry[J].BBA-Gen Subj,1992,1156(1):62-66.
[7]MITCHELL A E,JONES A D,MERCER R S,et al.Characterization of pyrroloquinoline quinone amino acid derivatives by electrospray ionization mass spectrometry and detection in human milk[J].%Anal Biochem,1999,269(2):317-325.
[8]AKIHARU W,NORIO H,TAKAO T.Protective effect of pyrroloquinoline quinone against experimental liver injury in rats[J].%Curr Therap Res,1988,44:896-901.
[9]AKAIKE T.PQQ as a generator and a scavenger of oxygen radicals determination with ESR spectroscopy using a spin trap agent.In:FUKUI,T,et al.Enzymes dependent on pyridoxal phosphate and other carbonyl compounds as factor.Oxford,New York,Seoul,Tokyo:Pergamon Press,1991:511-513.
[10]MA K,CUI J Z,YE J B,et al.Pyrroloquinoline quinone from Gluconobacter oxydans fermentation broth enhances superoxide anion-scavenging capacity of Cu/Zn-SOD[J].Food Chem,2017,230:291.
[11]AIZENMAN E,KAREN A H,ZHONG C,et al.Interaction of the putative essential nutrient PQQ with the N-methyl-D-aspartate receptor redox modulatory site[J].J Neurosci,1992,12:2362-2369.
[12]KOHJI Y,AKERI S,TEIZI U,et al.Stimulation of nerve growth factor production by pyrroloquinoline quinone and its derivatives in vitro and in vivo[J].Biosci Biotech Biochem,1993,57:1231-1233.
[13]KUMAZAWA T,HIWASA T,TAKIGUCHI M,et al.Activation of ras signaling pathways by pyrroloquinoline quinone in NIH3T3 mouse fibroblasts[J].Int J Mol Med,2007,19(5):765-770.
[14]李皓桓,贺斌,彭昊,等.吡咯喹啉醌对许旺细胞增殖及c-fos、c-jun、CREB和PCNA表达的影响[J].中华整形外科杂志,2011,27(4):298-301.
[15]贺斌,陶海鹰,卫爱林,等.吡咯喹啉醌对氧化应激诱导雪旺细胞凋亡的保护作用及其机制[J].中华整形外科杂志,2014,30(2):111-117.
[16]KHAIRNAR N P,KAMBLE V A,MANGOLI S H,et al.Involvement of a periplasmic protein kinase in DNA strand break repair and homologous recombination in Escherichia coli[J].Mol Microbiol,2007,65(2):294-304.
[17]RAJPUROHIT Y S,GOPALAKROSHNAN R,MISRA H S.Involvement of a protein kinase activity inducer in DNA double strand break repair and radioresistance of Deinococcus radiodurans[J].%J Bacteriol,2008,190(11):3948-3954.
[18]TANNE C,GOBEL G,LISDAT F,et al.Development of a PQQ-GDH-anode based on MWCNT modified gold and its application in a glucose/O2-biofuel cell[J].Biosens Bioelect,2010,26(2):530-535.
[19]YUHASHI N,TOMIYAMA M,OKUDA J,et al.Development of a novel glucose enzyme fuel cell system employing protein engineered PQQglucose dehydrogenase[J].Biosens Bioelect,2005,20(10):2145-2150.
[20]新思界.吡咯喹啉醌市场前景分析[EB/OL].http://www.newsijie.com/chanye/huagong/jujiao/2017/0830/11241280.html.
[21]唐靓,张岭,李林子,等.吡咯喹啉醌研究新进展[J].食品科学,2015,36(19):287-291.
[22]GUO Z,MURPHY L,STEIN V,et al.Engineered PQQ-glucose dehydrogenase as a universal biosensor platform[J].J Am Chem Soc,2016,138(32):10108-10111.
[23]司振军.微生物高效生产吡咯喹啉醌和聚苹果酸的研究[D].杭州:浙江大学,2017.
[24]王朝绚.吡咯喹啉醌工程菌构建及关键基因研究[D].北京:北京化工大学,2013.
[25]PRUST C,HOFFMEISTER M,LIESEGANG H,et al.Complete genome sequence of the acetic acid bacterium Gluconobacter oxydans[J].Nature Biotechnol,2005,23:195-200.
[26]HOLSCHER T,GORISCH H.Knockout and overexpression of pyrroloquinoline quinone biosynthetic genes in Gluconobacter oxydans 621H[J].J Bacteriol,2006,188:7668-7676.
[27]KLEEF M A,DUINE J A.L-tyrosine is the precursor of PQQ biosynthesis in Hyphomicrobium X[J].FEBS Lett,1988,237:91-97.
[28]SHEN Y Q,BONNOT F,IMSAND E M,et al.Distribution and properties of the genes encoding the biosynthesis of the bacterial cofactor,pyrroloquinoline quinone[J].Biochem,2012,51(11):2265-2275.
[29]VELTEROP J S,SELLINK E,MEULENBERG J J,et al.Synthesis of pyrroloquinoline quinone in vivo and in vitro and detection of an intermediate in the biosynthetic pathway[J].J Bacteriol,1995,177:5088-5098.
[30]MEYER J B,FRAPOLLI M,KEEL C,et al.Pyrroloquinoline quinone biosynthesis gene pqq C,a novel molecular marker for studying the phylogeny and diversity of phosphate-solubilizing pseudomonads[J].Appl Environ Microbiol,2011,77(20):7345-7354.
[31]HOUCK D R,HANNERS J L,UNKEFER C C.Biosynthesis of pyrroloquinoline quinine.Identification of biosynthetic precursors using13Clabeling and NMR spectroscopy[J].J Am Chem Soc,1988,110:6020-6021.
[32]MAGNUSSON O T,TOYAMA H,SAEKI M,et al.Quinone biogenesis:Structure and mechanism of PqqC,the final catalyst in the production of pyrroloquinoline quinone[J].P Natl Acad Sci USA,2004,101(21):7913-7918.
[33]PUEHRINGER S,METLITZKY M,SCHWARZENBACHER R.The pyrroloquinoline quinone biosynthesis pathway revisited:A structural approach[J].BMC Biochem,2008,9:8-17.
[34]GAO L L,HU Y D,LIU J,et al.Stepwise metabolic engineering of Gluconobacter oxydans WSH-003 for the direct production of 2-keto-L-gulonic acid from D-sorbitol[J].Metab Eng,2014,24:30-37.
[35]YUAN J F,WU M B,LIN J P,et al.Combinatorial metabolic engineering of industrial Gluconobacter oxydans DSM2343 for boosting 5-ketoD-gluconic acid accumulation[J].BMC Biotechnol,2016,16(1):42.
[36]孙继国.利用不同启动子在大肠杆菌与肺炎克雷伯氏中合成PQQ的研究[D].北京:北京化工大学,2013.
[37]李盼盼.氧化葡萄糖酸杆菌合成吡咯喹啉醌的研究[D].郑州:郑州轻工业学院,2016.
[38]MEULENBERG J J M,SELLINK E,RIEGMAN N H,et al.Nucleotide sequence and structure of the Klebsiella pneumoniae pqq operon[J].Mol General Genetics Mgg,1992,232(2):284-294.
[39]URAKAMI T,YASHIMA K,KOBAYASHI H,et al.Production of pyrroloquinoline quinone by using methanol-utilizing bacteria[J].%Appl Environ Microbiol,1992,58(12):3970-3976.
[40]杨诗颖,陈佳,柯崇榕,等.吡咯喹啉醌产生菌的筛选及其培养基优化[J].药物生物技术,2014(5):429-432.
[41]钟杉杉.吡咯喹啉醌高产菌的筛选、诱变、发酵及基因克隆[D].北京:北京化工大学,2013.
[42]郑璞,姚红涛.一种甲基营养菌及其发酵生产吡咯喹啉醌的方法:CN201410087026.4[P].2014-07-02.
[43]XIONG X H,ZHAO Y,GE X,et al.Production and radioprotective effects of pyrroloquinoline quinone[J].Int J Mol Sci,2011,12(12):8913-8923.