综述 |
|
|
|
|
微生物合成奇数链脂肪酸研究进展* |
白松,侯正杰,高庚荣,乔斌,程景胜() |
天津大学化工学院 教育部合成生物学前沿科学中心 系统生物工程教育部重点实验室 天津 300372 |
|
Advances in the Synthesis of Odd-chain Fatty Acids by Microorganisms |
BAI Song,HOU Zheng-jie,GAO Geng-rong,QIAO Bin,CHENG Jing-sheng() |
Frontiers Science Center for Synthetic Biology and Key Laboratory of Systems Bioengineering Ministry of Education, School of Chemical Engineering and Technology, Tianjin University, Tianjin 300372, China |
引用本文:
白松,侯正杰,高庚荣,乔斌,程景胜. 微生物合成奇数链脂肪酸研究进展*[J]. 中国生物工程杂志, 2022, 42(6): 76-85.
BAI Song,HOU Zheng-jie,GAO Geng-rong,QIAO Bin,CHENG Jing-sheng. Advances in the Synthesis of Odd-chain Fatty Acids by Microorganisms. China Biotechnology, 2022, 42(6): 76-85.
链接本文:
https://manu60.magtech.com.cn/biotech/CN/10.13523/j.cb.2201051
或
https://manu60.magtech.com.cn/biotech/CN/Y2022/V42/I6/76
|
[1] |
Lamont M, Amezquita E M, Ganuza T E. Food additive useful in processed food product or food component, and treating gene metabolic disorders comprises microalgal anaplerotic oil rich in saturated tridecanoic, pentadecanoic, and heptadecanoic odd-chain fatty acids: US20210051988A1. 2021-02-25. [2021-11-20]. https://www.webofscience.com/wos/alldb/full-record/DIIDW:202119412Q.
|
[2] |
Dornan K, Gunenc A, Oomah B D, et al. Odd chain fatty acids and odd chain phenolic lipids (alkylresorcinols) are essential for diet. Journal of the American Oil Chemists’ Society, 2021, 98(8): 813-824.
doi: 10.1002/aocs.12507
|
[3] |
Liu H B, Yu H Y, Xia J, et al. Topical azelaic acid, salicylic acid, nicotinamide, sulphur, zinc and fruit acid (alpha-hydroxy acid) for acne. The Cochrane Database of Systematic Reviews, 2020, 5(5): CD011368.
|
[4] |
Gillingham M B, Heitner S B, Martin J, et al. Triheptanoin versus trioctanoin for long-chain fatty acid oxidation disorders: a double blinded, randomized controlled trial. Journal of Inherited Metabolic Disease, 2017, 40(6): 831-843.
doi: 10.1007/s10545-017-0085-8
pmid: 28871440
|
[5] |
Imamura F, Sharp S J, Koulman A, et al. A combination of plasma phospholipid fatty acids and its association with incidence of type 2 diabetes: the EPIC-InterAct case-cohort study. PLoS Medicine, 2017, 14(10): e1002409.
doi: 10.1371/journal.pmed.1002409
|
[6] |
Weitkunat K, Schumann S, Nickel D, et al. Odd-chain fatty acids as a biomarker for dietary fiber intake: a novel pathway for endogenous production from propionate. The American Journal of Clinical Nutrition, 2017, 105(6): 1544-1551.
|
[7] |
黄霄霄. 从天然偶碳脂肪酸合成奇碳脂肪酸的研究. 无锡: 江南大学, 2013.
|
|
Huang X X. Synthesis of odd-numbered fatty acids from natural even-numbered fatty acids. Wuxi: Jiangnan University, 2013.
|
[8] |
Zhang L S, Liang S, Zong M H, et al. Microbial synthesis of functional odd-chain fatty acids: a review. World Journal of Microbiology & Biotechnology, 2020, 36(3): 35.
doi: 10.1007/s11274-020-02814-5
|
[9] |
Wu H, San K Y. Efficient odd straight medium chain free fatty acid production by metabolically engineered Escherichia coli. Biotechnology and Bioengineering, 2014, 111(11): 2209-2219.
doi: 10.1002/bit.25296
|
[10] |
Park Y K, Dulermo T, Ledesma-Amaro R, et al. Optimization of odd chain fatty acid production by Yarrowia lipolytica. Biotechnology for Biofuels, 2018, 11: 158.
doi: 10.1186/s13068-018-1154-4
|
[11] |
Park Y K, Ledesma-Amaro R, Nicaud J M. De novo biosynthesis of odd-chain fatty acids in Yarrowia lipolytica enabled by modular pathway engineering. Frontiers in Bioengineering and Biotechnology, 2020, 7: 484.
doi: 10.3389/fbioe.2019.00484
|
[12] |
Bhatia S K, Gurav R, Choi T R, et al. A clean and green approach for odd chain fatty acids production in Rhodococcus sp. YHY 01 by medium engineering. Bioresource Technology, 2019, 286: 121383.
doi: 10.1016/j.biortech.2019.121383
|
[13] |
Fontanille P, Kumar V, Christophe G, et al. Bioconversion of volatile fatty acids into lipids by the oleaginous yeast Yarrowia lipolytica. Bioresource Technology, 2012, 114: 443-449.
doi: 10.1016/j.biortech.2012.02.091
pmid: 22464419
|
[14] |
Ledesma-Amaro R, Dulermo R, Niehus X, et al. Combining metabolic engineering and process optimization to improve production and secretion of fatty acids. Metabolic Engineering, 2016, 38: 38-46.
doi: S1096-7176(16)30048-9
pmid: 27301328
|
[15] |
Degwert J, Jacob J, Steckel F. Use of cis-9-heptadecenoic acid for treating psoriasis and allergies: EP, EP19940912534. 1993-03-24[2021-11-20]. https://europepmc.org/article/PAT/EP0690710.
|
[16] |
Shirley M. Correction to: triheptanoin: first approval. Drugs, 2020, 80(17): 1873.
doi: 10.1007/s40265-020-01426-5
|
[17] |
Avis T J, Boulanger R R, Bélanger R R. Synthesis and biological characterization of (Z)-9-heptadecenoic and (Z)-6-methyl-9-heptadecenoic acids: fatty acids with antibiotic activity produced by Pseudozyma flocculosa. Journal of Chemical Ecology, 2000, 26(4): 987-1000.
doi: 10.1023/A:1005464326573
|
[18] |
Weitkunat K, Bishop C A, Wittmüss M, et al. Effect of microbial status on hepatic odd-chain fatty acids is diet-dependent. Nutrients, 2021, 13(5): 1546.
doi: 10.3390/nu13051546
|
[19] |
Toral P G, Hervás G, Badia A D, et al. Effect of dietary lipids and other nutrients on milk odd- and branched-chain fatty acid composition in dairy ewes. Journal of Dairy Science, 2020, 103(12): 11413-11423.
doi: 10.3168/jds.2020-18580
pmid: 33069404
|
[20] |
Aglago E K, Biessy C, Torres-Mejía G, et al. Association between serum phospholipid fatty acid levels and adiposity in Mexican women. Journal of Lipid Research, 2017, 58(7): 1462-1470.
doi: 10.1194/jlr.P073643
pmid: 28465289
|
[21] |
Park Y K, Nicaud J M. Metabolic engineering for unusual lipid production in Yarrowia lipolytica. Microorganisms, 2020, 8(12): 1937.
doi: 10.3390/microorganisms8121937
|
[22] |
沙莎, 郑玉斌. 利用奇数碳二元酸制备透明聚酰胺的研究. 塑料科技, 2016, 44(8): 37-41.
|
|
Sha S, Zheng Y B. Study on transparent polyamide with odd carbon dicarboxylic acid. Plastics Science and Technology, 2016, 44(8): 37-41.
|
[23] |
Blaskovich M A T, Elliott A G, Kavanagh A M, et al. In vitro antimicrobial activity of acne drugs against skin-associated bacteria. Scientific Reports, 2019, 9(1): 14658.
doi: 10.1038/s41598-019-50746-4
pmid: 31601845
|
[24] |
Searle T, Ali F R, Al-Niaimi F. The versatility of azelaic acid in dermatology. The Journal of Dermatological Treatment, 2022, 33(2): 722-732.
doi: 10.1080/09546634.2020.1800579
|
[25] |
Vockley J, Charrow J, Ganesh J, et al. Triheptanoin treatment in patients with pediatric cardiomyopathy associated with long chain-fatty acid oxidation disorders. Molecular Genetics and Metabolism, 2016, 119(3): 223-231.
doi: S1096-7192(16)30205-0
pmid: 27590926
|
[26] |
Prada M, Wittenbecher C, Eichelmann F, et al. Association of the odd-chain fatty acid content in lipid groups with type 2 diabetes risk: a targeted analysis of lipidomics data in the EPIC-Potsdam cohort. Clinical Nutrition, 2021, 40(8): 4988-4999.
doi: 10.1016/j.clnu.2021.06.006
|
[27] |
Jenkins B, Aoun M, Feillet-Coudray C, et al. The dietary total-fat content affects the in vivo circulating C15: 0 and C17: 0 fatty acid levels independently. Nutrients, 2018, 10(11): 1646.
doi: 10.3390/nu10111646
|
[28] |
Poppitt S D. Cow’s milk and dairy consumption: is there now consensus for cardiometabolic health. Frontiers in Nutrition, 2020, 7: 574725.
doi: 10.3389/fnut.2020.574725
|
[29] |
To N B, Nguyen Y T K, Moon J Y, et al. Pentadecanoic acid, an odd-chain fatty acid, suppresses the stemness of MCF-7/SC human breast cancer stem-like cells through JAK2/STAT3 signaling. Nutrients, 2020, 12(6): 1663.
doi: 10.3390/nu12061663
|
[30] |
Venn-Watson S, Lumpkin R, Dennis E A. Efficacy of dietary odd-chain saturated fatty acid pentadecanoic acid parallels broad associated health benefits in humans: could it be essential. Scientific Reports, 2020, 10: 8161.
doi: 10.1038/s41598-020-64960-y
pmid: 32424181
|
[31] |
Ediriweera M K, To N B, Lim Y, et al. Odd-chain fatty acids as novel histone deacetylase 6 (HDAC6) inhibitors. Biochimie, 2021, 186: 147-156.
|
[32] |
Dowd M K, Farve M C. Fatty acid composition of Tilia spp. seed oils. Grasas Y Aceites, 2013, 64(3): 243-249.
doi: 10.3989/gya.096012
|
[33] |
Wen J, Hu C Q, Fan S G. Chemical composition and nutritional quality of sea cucumbers. Journal of the Science of Food and Agriculture, 2010, 90(14): 2469-2474.
doi: 10.1002/jsfa.4108
|
[34] |
Zhang L S, Xu P, Chu M Y, et al. Using 1-propanol to significantly enhance the production of valuable odd-chain fatty acids by Rhodococcus opacus PD630. World Journal of Microbiology & Biotechnology, 2019, 35(11): 164.
doi: 10.1007/s11274-019-2748-0
|
[35] |
Buitenhuis B, Lassen J, Noel S J, et al. Impact of the rumen microbiome on milk fatty acid composition of Holstein cattle. Genetics, Selection, Evolution: GSE, 2019, 51(1): 23.
doi: 10.1186/s12711-019-0464-8
pmid: 31142263
|
[36] |
Kolouchová I, Schreiberová O, Sigler K, et al. Biotransformation of volatile fatty acids by oleaginous and non-oleaginous yeast species. FEMS Yeast Research, 2015, 15(7): fov076.
|
[37] |
Wang F Z, Bi Y L, Diao J J, et al. Metabolic engineering to enhance biosynthesis of both docosahexaenoic acid and odd-chain fatty acids in Schizochytrium sp. S31. Biotechnology for Biofuels, 2019, 12: 141.
doi: 10.1186/s13068-019-1484-x
|
[38] |
Price N P J, Jackson M A, Hartman T M, et al. Branched chain lipid metabolism as a determinant of the N-acyl variation of Streptomyces natural products. ACS Chemical Biology, 2021, 16(1): 116-124.
doi: 10.1021/acschembio.0c00799
pmid: 33411499
|
[39] |
Adli M. The CRISPR tool kit for genome editing and beyond. Nature Communications, 2018, 9(1): 1911.
doi: 10.1038/s41467-018-04252-2
|
[40] |
Shi T Q, Huang H, Kerkhoven E J, et al. Advancing metabolic engineering of Yarrowia lipolytica using the CRISPR/Cas system. Applied Microbiology and Biotechnology, 2018, 102(22): 9541-9548.
doi: 10.1007/s00253-018-9366-x
|
[41] |
Wu H, San K Y. Engineering Escherichia coli for odd straight medium chain free fatty acid production. Applied Microbiology and Biotechnology, 2014, 98(19): 8145-8154.
doi: 10.1007/s00253-014-5882-5
|
[42] |
Maurer S, Schewe H, Schrader J, et al. Investigation of fatty aldehyde and alcohol synthesis from fatty acids by αDox- or CAR-expressing Escherichia coli. Journal of Biotechnology, 2019, 305: 11-17.
doi: 10.1016/j.jbiotec.2019.08.011
|
[43] |
Cao Y X, Xiao W H, Liu D, et al. Biosynthesis of odd-chain fatty alcohols in Escherichia coli. Metabolic Engineering, 2015, 29: 113-123.
doi: 10.1016/j.ymben.2015.03.005
|
[44] |
Jin Z, Wong A, Foo J L, et al. Engineering Saccharomyces cerevisiae to produce odd chain-length fatty alcohols. Biotechnology and Bioengineering, 2016, 113(4): 842-851.
doi: 10.1002/bit.25856
|
[45] |
Liu H, Marsafari M, Wang F, et al. Engineering acetyl-CoA metabolic shortcut for eco-friendly production of polyketides triacetic acid lactone in Yarrowia lipolytica. Metabolic Engineering, 2019, 56: 60-68.
doi: 10.1016/j.ymben.2019.08.017
|
[46] |
Lee G J, Haliburton J R, Hu Z H, et al. Production of odd chain fatty acid derivatives in recombinant microbial cells: US, US20210324431A1. 2021-10-21[2021-11-20]. https://appft.uspto.gov/netacgi/nph-Parser?Sect1=PTO1&Sect2=HITOFF&p=1&u=/netahtml/PTO/srchnum.html&r=1&f=G&l=50&d=PG01&s1=20210324431.PGNR.
|
[47] |
Tseng H C, Prather K L J. Controlled biosynthesis of odd-chain fuels and chemicals via engineered modular metabolic pathways. Proceedings of the National Academy of Sciences of the United States of America, 2012, 109(44): 17925-17930.
|
[48] |
Ingram L O, Chevalier L S, Gabba E J, et al. Propionate-induced synthesis of odd-chain-length fatty acids by Escherichia coli. Journal of Bacteriology, 1977, 131(3): 1023-1025.
doi: 10.1128/jb.131.3.1023-1025.1977
pmid: 330493
|
[49] |
Park Y K, Bordes F, Letisse F, et al. Engineering precursor pools for increasing production of odd-chain fatty acids in Yarrowia lipolytica. Metabolic Engineering Communications, 2021, 12: e00158.
doi: 10.1016/j.mec.2020.e00158
|
[50] |
Han J, Hou J, Zhang F, et al. Multiple propionyl coenzyme A-supplying pathways for production of the bioplastic poly(3-hydroxybutyrate-co-3-hydroxyvalerate) in Haloferax mediterranei. Applied and Environmental Microbiology, 2013, 79(9): 2922-2931.
doi: 10.1128/AEM.03915-12
|
[51] |
Imatoukene N, Verbeke J, Beopoulos A, et al. A metabolic engineering strategy for producing conjugated linoleic acids using the oleaginous yeast Yarrowia lipolytica. Applied Microbiology and Biotechnology, 2017, 101(11): 4605-4616.
doi: 10.1007/s00253-017-8240-6
pmid: 28357546
|
[52] |
Ledesma-Amaro R, Nicaud J M. Yarrowia lipolytica as a biotechnological chassis to produce usual and unusual fatty acids. Progress in Lipid Research, 2016, 61: 40-50.
doi: 10.1016/j.plipres.2015.12.001
pmid: 26703186
|
[53] |
Ghogare R, Chen S L, Xiong X C. Metabolic engineering of oleaginous yeast Yarrowia lipolytica for overproduction of fatty acids. Frontiers in Microbiology, 2020, 11: 1717.
doi: 10.3389/fmicb.2020.01717
|
[54] |
Ferreira R, Teixeira P G, Gossing M, et al. Metabolic engineering of Saccharomyces cerevisiae for overproduction of triacylglycerols. Metabolic Engineering Communications, 2018, 6: 22-27.
doi: 10.1016/j.meteno.2018.01.002
pmid: 29896445
|
[55] |
Fang L, Fan J, Luo S, et al. Genome-scale target identification in Escherichia coli for high-titer production of free fatty acids. Nature Communications, 2021, 12(1): 4976.
doi: 10.1038/s41467-021-25243-w
|
[56] |
Xu P, Gu Q, Wang W, et al. Modular optimization of multi-gene pathways for fatty acids production in E. coli. Nature Communications, 2013, 4: 1409.
doi: 10.1038/ncomms2425
|
[57] |
Howard T P, Middelhaufe S, Moore K, et al. Synthesis of customized petroleum-replica fuel molecules by targeted modification of free fatty acid pools in Escherichia coli. Proceedings of the National Academy of Sciences of the United States of America, 2013, 110(19): 7636-7641.
|
[58] |
Řezanka T, Kolouchová I, Sigler K, Precursor directed biosynthesis of odd-numbered fatty acids by different yeasts. Folia Microbiologica, 2013, 110(19): 7636-7641.
|
[59] |
Zhuang Q Q, Qi Q S. Engineering the pathway in Escherichia coli for the synthesis of medium-chain-length polyhydroxyalkanoates consisting of both even- and odd-chain monomers. Microbial Cell Factories, 2019, 18(1): 135.
doi: 10.1186/s12934-019-1186-x
|
|
Viewed |
|
|
|
Full text
|
|
|
|
|
Abstract
|
|
|
|
|
Cited |
|
|
|
|
|
Shared |
|
|
|
|
|
Discussed |
|
|
|
|