|
|
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 |
|
|
Abstract Odd-chain fatty acids (OCFAs) are widely distributed in nature, while their level is low. OCFA has huge application potential in the fields of medicine, health, and industry. The current methods of obtaining OCFA are mainly included in the extraction and chemical synthesis, which limits its application due to the higher-cost and the lower-efficiency. Microbial fermentation is one of the most promising strategies for large-scale industrial production. This article briefly discusses the scope of application of OCFA, summarizes the microorganisms that can naturally synthesize OCFA, introduces in detail the related metabolic pathways involved in microbial synthesis of OCFA, and reviews the current strategies of genetic engineering and fermentation regulation for improving OCFA production. Taken together, this summary aims to provide a more systematic and comprehensive theoretical basis for improving OCFA production of microorganism by synthetic biology strategies.
|
Received: 27 January 2022
Published: 07 July 2022
|
|
Corresponding Authors:
Jing-sheng CHENG
E-mail: jscheng@tju.edu.cn
|
|
|
[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.
|
|
|
[7] |
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.
|
|
|
[22] |
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 |
|
|
|
|