综述 |
|
|
|
|
桉叶素生物合成研究进展 |
匙占库,文孟良,赵江源,李铭刚,韩秀林() |
云南生物资源保护与利用国家重点实验室 西南微生物多样性教育部重点实验室 云南省微生物研究所 云南大学生命科学学院 昆明 650091 |
|
Recent Advances in Biosynthesis of 1,8-Cineole |
Zhan-ku SHI,Meng-liang WEN,Jiang-yuan ZHAO,Ming-gang LI,Xiu-lin HAN() |
State Key Laboratory for Conservation and Utilization of Bio-Resources in Yunnan,Key Laboratory of Microbial Diversity in Southwest of China, Ministry of Education,Yunnan Institute of Microbiology, School of Life Sciences, Yunnan University, Kunming 650091, China |
引用本文:
匙占库,文孟良,赵江源,李铭刚,韩秀林. 桉叶素生物合成研究进展[J]. 中国生物工程杂志, 2018, 38(11): 92-102.
Zhan-ku SHI,Meng-liang WEN,Jiang-yuan ZHAO,Ming-gang LI,Xiu-lin HAN. Recent Advances in Biosynthesis of 1,8-Cineole. China Biotechnology, 2018, 38(11): 92-102.
链接本文:
https://manu60.magtech.com.cn/biotech/CN/10.13523/j.cb.20181112
或
https://manu60.magtech.com.cn/biotech/CN/Y2018/V38/I11/92
|
[1] |
Viturro C I, Molina A C, Heit C I . Volatile components of Eucalyptus globulus Labill ssp. bicostata from Jujuy, Argentina. J Essent Oil Res, 2003,15(3):206-208.
doi: 10.1080/10412905.2003.9712115
|
[2] |
Tizianabaratta M, Damiendorman H J, Deans S , et al. Chemical composition, antimicrobial and antioxidative activity of laurel, sage, rosemary, oregano and coriander essential oils. J Essent Oil Res, 1998,10(6):618-627.
doi: 10.1080/10412905.1998.9700989
|
[3] |
Hussain A I, Anwar F, Nigam P S , et al. Antibacterial activity of some Lamiaceae essential oils using resazurin as an indicator of cell growth. LWT- Food Sci Technol, 2011,44(4):1199-1206.
doi: 10.1016/j.lwt.2010.10.005
|
[4] |
Wang K Y, Strobel G A, Yan D H . The production of 1,8-cineole, a potential biofuel, from an endophytic strain of Annulohypoxylon sp. FPYF3050 when grown on agricultural residues. J Sustain Bioenergy Syst, 2017,7(2):65-84.
doi: 10.4236/jsbs.2017.72006
|
[5] |
Hu Z, Chen Z, Yin Z , et al. In vitro acaricidal activity of 1,8-cineole against Sarcoptes scabiei var. cuniculi and regulating effects on enzyme activity. Parasitol Res, 2015,114(8):2959-2567.
doi: 10.1007/s00436-015-4498-8
pmid: 25924796
|
[6] |
Caldas G F R, Oliveira A R D S, Araújo A V , et al. Gastroprotective mechanisms of the monoterpene 1,8-cineole (eucalyptol). PLoS One, 2015,10(8):e0134558.
doi: 10.1371/journal.pone.0134558
pmid: 26244547
|
[7] |
Juergens U R . Anti-inflammatory properties of the monoterpene 1.8-cineole: current evidence for co-medication in inflammatory airway diseases. Drug Res (Stuttg), 2014,64(12):638-646.
doi: 10.1055/s-0034-1372609
pmid: 24831245
|
[8] |
Khan A, Vaibhav K, Javed H , et al. 1,8-cineole (eucalyptol) mitigates inflammation in amyloid beta toxicated PC12 cells: relevance to Alzheimer’s disease. Neurochem Res, 2014,39(2):344-352.
doi: 10.1007/s11064-013-1231-9
pmid: 24379109
|
[9] |
Moon H K, Kang P, Lee H S , et al. Effects of 1,8-cineole on hypertension induced by chronic exposure to nicotine in rats. J Pharm Pharmacol, 2014,66(5):688-693.
doi: 10.1111/jphp.12195
|
[10] |
Santos F A, Silva R M, Tome A R , et al. 1,8-Cineole protects against liver failure in an in-vivo murine model of endotoxemic shock. J Pharm Pharmacol, 2001,53(4):505-511.
doi: 10.1211/0022357011775604
pmid: 11341367
|
[11] |
Moteki H, Hibasami H, Yamada Y , et al. Specific induction of apoptosis by 1,8-cineole in two human leukemia cell lines, but not a in human stomach cancer cell line. Oncol Rep, 2002,9(4):757-760.
doi: 10.3892/or.9.4.757
pmid: 12066204
|
[12] |
Dhakad A K, Pandey V V, Beg S , et al. Biological, medicinal and toxicological significance of Eucalyptus leaf essential oil: a review. J Sci Food Agric, 2017,98(3):833-848.
doi: 10.1002/jsfa.8600
pmid: 28758221
|
[13] |
Lahlou S, Figueiredo A F, Magalh?es P J , et al. Cardiovascular effects of 1,8-cineole, a terpenoid oxide present in many plant essential oils, in normotensive rats. Can J Physiol Pharmacol, 2002,80(12):1125-1131.
doi: 10.1139/y02-142
pmid: 12564637
|
[14] |
Verma P, Sharma M P, Dwivedi G . Potential use of eucalyptus biodiesel in compressed ignition engine. Egypt J Pet, 2016,25(1):91-95.
doi: 10.1016/j.ejpe.2015.03.008
|
[15] |
Zebec Z, Wilkes J, Jervis A J , et al. Towards synthesis of monoterpenes and derivatives using synthetic biology. Curr Opin Chem Biol, 2016,34:37-43.
doi: 10.1016/j.cbpa.2016.06.002
pmid: 27315341
|
[16] |
Tholl D . Terpene synthases and the regulation, diversity and biological roles of terpene metabolism. Curr Opin Plant Biol, 2006,9(3):297-304.
doi: 10.1016/j.pbi.2006.03.014
|
[17] |
Croteau R, Alonso W R, Koepp A E , et al. Biosynthesis of monoterpenes: partial purification, characterization, and mechanism of action of 1,8-cineole synthase. Arch Biochem Biophys, 1994,309(1):184-192.
doi: 10.1006/abbi.1994.1101
pmid: 8117108
|
[18] |
Kampranis S C, Ioannidis D, Purvis A , et al. Rational conversion of substrate and product specificity in a Salvia monoterpene synthase: structural insights into the evolution of terpene synthase function. Plant Cell, 2007,19(6):1994-2005.
doi: 10.1105/tpc.106.047779
|
[19] |
Karuppiah V, Ranaghan K E ,Leferink N G H, , et al. Structural basis of catalysis in the bacterial monoterpenesynthases linalool synthase and 1,8-cineole synthase. ACS Catal, 2017,7(9):6268-6282.
doi: 10.1021/acscatal.7b01924
pmid: 5617326
|
[20] |
Wise M L, Savage T J, Katahira E , et al. Monoterpene synthases from common sage (Salvia officinalis). cDNA isolation, characterization, and functional expression of (+)-sabinene synthase, 1,8-cineole synthase, and (+)-bornyl diphosphate synthase. J Biol Chem, 1998,273(24):14891-14899.
doi: 10.1074/jbc.273.24.14891
|
[21] |
Chen F, Ro D K, Petri J , et al. Characterization of a root-specific Arabidopsis terpene synthase responsible for the formation of the volatile monoterpene 1,8-cineole. Plant Physiol, 2004,135(4):1956-1966.
doi: 10.1104/pp.104.044388
pmid: 15299125
|
[22] |
Shimada T, Endo T, Fujii H , et al. Isolation and characterization of (E)-beta-ocimene and 1,8 cineole synthases in Citrus unshiu Marc. Plant Sci, 2005,168(4):987-995.
doi: 10.1016/j.plantsci.2004.11.012
|
[23] |
Roeder S, Hartmann A M, Effmert U , et al. Regulation of simultaneous synthesis of floral scent terpenoids by the 1,8-cineole synthase of Nicotiana suaveolens. Plant Mol Biol, 2007,65(1-2):107-124.
doi: 10.1007/s11103-007-9202-7
pmid: 17611797
|
[24] |
Fahnrich A, Brosemann A, Teske L , et al. Synthesis of ‘cineole cassette’ monoterpenes in Nicotiana section Alatae: gene isolation, expression, functional characterization and phylogenetic analysis. Plant Mol Biol, 2012,79(6):537-553.
doi: 10.1007/s11103-012-9933-y
|
[25] |
Fahnrich A, Neumann M, Piechulla B . Characteristic alatoid ‘cineole cassette’ monoterpene synthase present in Nicotiana noctiflora. Plant Mol Biol, 2014,85(1-2):135-145.
doi: 10.1007/s11103-014-0176-y
pmid: 24493662
|
[26] |
Nakano C, Kim H K, Ohnishi Y . Identification of the first bacterial monoterpene cyclase, a 1,8-cineole synthase, that catalyzes the direct conversion of geranyl diphosphate. Chembiochem, 2011,12(13):1988-1991.
doi: 10.1002/cbic.201100330
pmid: 21726035
|
[27] |
Demissie Z A, Cella M A, Sarker L S , et al. Cloning, functional characterization and genomic organization of 1,8-cineole synthases from Lavandula. Plant Mol Biol, 2012,79(4-5):393-411.
doi: 10.1007/s11103-012-9920-3
pmid: 22592779
|
[28] |
Shaw J J, Berbasova T, Sasaki T , et al. Identification of a fungal 1,8-cineole synthase from Hypoxylon sp. with specificity determinants in common with the plant synthases. J Biol Chem, 2015,290(13):8511-8526.
doi: 10.1074/jbc.M114.636159
pmid: 25648891
|
[29] |
Ruan J X, Li J X, Fang X , et al. Isolation and characterization of three new monoterpene synthases from Artemisia annua. Front Plant Sci, 2016,7(45):638.
doi: 10.3389/fpls.2016.00638
pmid: 4861830
|
[30] |
Keszei A, Brubaker C L, Carter R , et al. Functional and evolutionary relationships between terpene synthases from Australian Myrtaceae. Phytochemistry, 2010,71(8-9):844-852.
doi: 10.1016/j.phytochem.2010.03.013
pmid: 20399476
|
[31] |
Balacs T . Cineole-rich eucalyptus. Int J Aromather, 1997,8(8):15-21.
doi: 10.1016/S0962-4562(97)80020-3
|
[32] |
Williams D C, Mcgarvey D J, Katahira E J , et al. Truncation of limonene synthase preprotein provides a fully active ‘pseudomature’ form of this monoterpene cyclase and reveals the function of the amino-terminal arginine pair. Biochemistry, 1998,37(35):12213-12220.
doi: 10.1021/bi980854k
pmid: 9724535
|
[33] |
Whittington D A, Wise M L, Urbansky M , et al. Bornyl diphosphate synthase: structure and strategy for carbocation manipulation by a terpenoid cyclase. Proc Natl Acad Sci USA, 2002,99(24):15375-15380.
doi: 10.1073/pnas.232591099
|
[34] |
Degenhardt J, Köllner T G, Gershenzon J . Monoterpene and sesquiterpene synthases and the origin of terpene skeletal diversity in plants. Phytochemistry, 2009,70(15):1621-1637.
doi: 10.1016/j.phytochem.2009.07.030
|
[35] |
Starks C M, Noel J P . Structural basis for cyclic terpene biosynthesis by tobacco 5-epi-aristolochene synthase. Science, 1997,277(5333):1815-1820.
doi: 10.1126/science.277.5333.1815
|
[36] |
Gao Y, Honzatko R B, Peters R J . Terpenoid synthase structures: A so far incomplete view of complex catalysis. Nat Prod Rep, 2012,29(10):1153-1175.
doi: 10.1039/c2np20059g
pmid: 3448952
|
[37] |
Piechulla B, Bartelt R, Brosemann A , et al. The α-terpineol to 1,8-cineole cyclization reaction of tobacco terpene synthases. Plant Physiol, 2016,172(4):2120-2131.
doi: 10.1104/pp.16.01378
pmid: 27729471
|
[38] |
Tomsheck A R, Strobel G A, Booth E , et al. Hypoxylon sp. an endophyte of Persea indica producing 1,8-cineole and other bioactive volatiles with fuel potential. Microb Ecol, 2010,60(4):903-914.
doi: 10.1007/s00248-010-9759-6
pmid: 20953951
|
[39] |
Mends M T, Yu E, Strobel G A , et al. An endophytic Nodulisporium sp. producing volatile organic ccompounds having bioactivity and fuel potential. J Pet Environ Biotechnol, 2012,3(Supplement S1):S33-S47.
|
[40] |
Riyaz-Ul-Hassan S, Strobel G, Geary B , et al. An endophytic Nodulisporium sp. from central America producing volatile organic compounds with both biological and fuel potential. J Microbiol Biotechnol, 2013,23(1):29-35.
doi: 10.1051/jp4:1993112
pmid: 23314364
|
[41] |
Goldstein J L, Brown M S . Regulation of the mevalonate pathway. Nature, 1990,343(6257):425-430.
doi: 10.1038/343425a0
|
[42] |
Ignea C, Cvetkovic I, Loupassaki S , et al. Improving yeast strains using recyclable integration cassettes, for the production of plant terpenoids. Microb Cell Fact, 2011,10(1):4.
doi: 10.1186/1475-2859-10-4
pmid: 21276210
|
[43] |
Erhardt H, Dempwolff F, Pfreundschuh M , et al. Organization of the Escherichia coli aerobic enzyme complexes of oxidative phosphorylation in dynamic domains within the cytoplasmic membrane. Microbiologyopen, 2014,3(3):316-326.
doi: 10.1002/mbo3.163
pmid: 24729508
|
[44] |
Mendez-Perez D, Alonsogutierrez J, Hu Q , et al. Production of jet fuel precursor monoterpenoids from engineered Escherichia coli. Biotechnol Bioeng, 2017,114(8):1703-1712.
doi: 10.1002/bit.26296
|
[45] |
Martin V J, Pitera D J, Withers S T , et al. Engineering a mevalonate pathway in Escherichia coli for production of terpenoids. Nat Biotechnol, 2003,21(7):796-802.
doi: 10.1038/nbt833
pmid: 12778056
|
[46] |
Guan Z, Xue D, Abdallah I I , et al. Metabolic engineering of Bacillus subtilis, for terpenoid production. Appl Microbiol Biotechnol, 2015,99(22):9395-9406.
doi: 10.1007/s00253-015-6950-1
pmid: 4628092
|
[47] |
Formighieri C, Melis A . Sustainable heterologous production of terpene hydrocarbons in cyanobacteria. Photosynth Res, 2016,130(1-3):1-13.
doi: 10.1007/s11120-015-0207-9
pmid: 26650229
|
[48] |
Paddon C J, Westfall P J, Pitera D J , et al. High-level semi-synthetic production of the potent antimalarial artemisinin. Nature, 2013,496(7446):528-532.
doi: 10.1038/nature12051
pmid: 23575629
|
[49] |
Westfall P J, Pitera D J, Lenihan J R , et al. Production of amorphadiene in yeast, and its conversion to dihydroartemisinic acid, precursor to the antimalarial agent artemisinin. Proc Natl Acad Sci USA, 2012,109(3):111-118.
doi: 10.1073/pnas.1110740109
pmid: 22247290
|
[50] |
Ro D K, Paradise E M, Ouellet M , et al. Production of the antimalarial drug precursor artemisinic acid in engineered yeast. Nature, 2006,440(7086):940-943.
doi: 10.1038/nature04640
pmid: 16612385
|
[51] |
Han G H, Kim S K, Yoon P K , et al. Fermentative production and direct extraction of (-)-α-bisabolol in metabolically engineered Escherichia coli. Microb Cell Fact, 2016,15(1):185.
doi: 10.1186/s12934-016-0588-2
pmid: 5282890
|
[52] |
You S, Yin Q, Zhang J , et al. Utilization of biodiesel by-product as substrate for high-production of β-farnesene via relatively balanced mevalonate pathway in Escherichia coli. Bioresour Technol, 2017,243:228.
doi: 10.1016/j.biortech.2017.06.058
pmid: 28672185
|
[53] |
Fischer M J, Meyer S, Claudel P , et al. Metabolic engineering of monoterpene synthesis in yeast. Biotechnol Bioeng, 2011,108(8):1883-1892.
doi: 10.1002/bit.23129
pmid: 21391209
|
[54] |
Carrau F M, Medina K, Boido E , et al. De novo synthesis of monoterpenes by Saccharomyces cerevisiae wine yeasts. FEMS Microbiol Lett, 2005,243(1):107-115.
doi: 10.1016/j.femsle.2004.11.050
pmid: 15668008
|
[55] |
Banerjee A, Sharkey T D . Methylerythritol 4-phosphate (MEP) pathway metabolic regulation. Nat Prod Rep, 2014,31(8):1043-1055.
doi: 10.1039/c3np70124g
pmid: 24921065
|
[56] |
Rodwell V W, Nordstrom J L, Mitschelen J J . Regulation of HMG-CoA reductase. Adv Lipid Res, 1976,14:1-74.
doi: 10.1016/B978-0-12-024914-5.50008-5
|
[57] |
Fujisaki S, Hara H, Nishimura Y , et al. Cloning and nucleotide sequence of the ispA gene responsible for farnesyl diphosphate synthase activity in Escherichia coli. J Biochem, 1990,108(6):995-1000.
doi: 10.1016/0141-8130(90)90047-E
pmid: 2089044
|
[58] |
Anderson M S, Yarger J G, Burck C L , et al. Farnesyl diphosphate synthetase. Molecular cloning, sequence, and expression of an essential gene from Saccharomyces cerevisiae. J Biol Chem, 1989,264(32):19176-19184.
doi: 10.1016/0006-291X(89)91832-9
pmid: 2681213
|
[59] |
Donald K A, Hampton R Y, Fritz I B . Effects of overproduction of the catalytic domain of 3-hydroxy-3-methylglutaryl coenzyme A reductase on squalene synthesis in Saccharomyces cerevisiae. Appl Environ Microbiol, 1997,63(9):3341-3344.
doi: 10.1016/S0027-5107(97)00112-7
pmid: 168639
|
[60] |
Engels B, Dahm P, Jennewein S . Metabolic engineering of taxadiene biosynthesis in yeast as a first step towards Taxol (Paclitaxel) production. Metab Eng, 2008,10(3-4):201-206.
doi: 10.1016/j.ymben.2008.03.001
pmid: 18485776
|
[61] |
Li Q, Sun Z, Li J , et al. Enhancing beta-carotene production in Saccharomyces cerevisiae by metabolic engineering. FEMS Microbiol Lett, 2013,345(2):94-101.
doi: 10.1111/1574-6968.12187
pmid: 23718229
|
[62] |
Fischer M J, Meyer S, Claudel P , et al. Metabolic engineering of monoterpene synthesis in yeast. Biotechnol Bioeng, 2011,108(8):1883-1892.
doi: 10.1002/bit.23129
pmid: 21391209
|
[63] |
Ignea C, Pontini M, Maffei M E , et al. Engineering monoterpene production in yeast using a synthetic dominant negative geranyl diphosphate synthase. ACS Synth Biol, 2014,3(5):298-306.
doi: 10.1021/sb400115e
pmid: 24847684
|
[64] |
Tashiro M, Kiyota H, Kawainoma S , et al. Bacterial production of pinene by a laboratory-evolved pinene-synthase. ACS Synth Biol, 2016,5(9):1011-1120.
doi: 10.1021/acssynbio.6b00140
pmid: 27247193
|
[65] |
Brennan T C R, Turner C D, Krömer J O , et al. Alleviating monoterpene toxicity using a two-phase extractive fermentation for the bioproduction of jet fuel mixtures in Saccharomyces cerevisiae. Biotechnol Bioeng, 2012,109(10):2513-3522.
doi: 10.1002/bit.24536
pmid: 22539043
|
[66] |
Zhang L, Xiao W H, Wang Y , et al. Chassis and key enzymes engineering for monoterpenes production. Biotechnol Adv, 2017,35(8):1022-1031.
doi: 10.1016/j.biotechadv.2017.09.002
pmid: 28888552
|
[67] |
Denby C M, Li R A, Vu V T , et al. Industrial brewing yeast engineered for the production of primary flavor determinants in hopped beer. Nat Commun., 2018,9(1):965-974.
doi: 10.1038/s41467-018-03293-x
pmid: 29559655
|
[68] |
Baadhe R R, Mekala N K, Parcha S R , et al. Combination of ERG9 repression and enzyme fusion technology for improved production of amorphadiene in Saccharomyces cerevisiae. J anal Methods Chem, 2013,2013(12):140469-140476.
doi: 10.1155/2013/140469
pmid: 24282652
|
[69] |
Jiang G Z, Yao M D, Wang Y , et al. Manipulation of GES and ERG20 for geraniol overproduction in Saccharomyces cerevisiae. Metab Eng, 2017,41:57-66.
doi: 10.1016/j.ymben.2017.03.005
pmid: 28359705
|
|
Viewed |
|
|
|
Full text
|
|
|
|
|
Abstract
|
|
|
|
|
Cited |
|
|
|
|
|
Shared |
|
|
|
|
|
Discussed |
|
|
|
|