Microbial Biosynthesis of Lactones: Gaps and Opportunities towards Sustainable Production
Source abstract
Abstract
Lactones are volatile organic compounds widely present in foods. These chemicals are applied as flavors and fragrances in the food, cosmetics and pharmaceutical industries. Recently, the potential of lactones as green solvents and fuel precursors reinforced their role as platform compounds of future bio-based economies. However, their current mode of production needs to change. Lactones are mainly obtained through chemical synthesis or microbial biotransformation of hydroxy fatty acids. The latter approach is preferred but still needs to use more sustainable substrates. Hydroxy fatty acids are non-abundant and non-sustainable substrates from environmental, health and economic points of view. Therefore, it is urgent to identify and engineer microorganisms with the rare ability to biosynthesize lactones from carbohydrates or renewable lipids. Here, we firstly address the variety and importance of lactones. Then, the current understanding of the biosynthetic pathways involved in lactone biosynthesis is presented, making use of the knowledge acquired in microorganisms and fruits. From there, we present and make the distinction between biotransformation processes and de novo biosynthesis of lactones. Finally, the opportunities and challenges towards more sustainable production in addition to the relevance of two well-known industrial microbes, the filamentous fungus Ashbya gossypii and the yeast Yarrowia lipolytica, are discussed.
Source: crossref · Quality: baseline
Research context
OpenAlex topics: Microbial Metabolic Engineering and Bioproduction · Biofuel production and bioconversion · Enzyme Catalysis and Immobilization
SciVX discovery tags are terminology-based. OpenAlex topics are source-provided classifications.
Affiliations
CEB—Centre of Biological Engineering, University of Minho, 4710-057 Braga, Portugal
Funding
European Regional Development Fund · Fundação para a Ciência e a Tecnologia
References (93)
Show source-provided references
1. Lactones with a Fragrance Properties
2. Microbial Lactone Synthesis Based on Renewable Resources10.1007/978-3-662-45209-7_10 ↗
3. Analytical Characterization of the Aroma of Tinta Negra Mole Red Wine: Identification of the Main Odorants Compounds10.1016/j.aca.2005.10.023 ↗
4. γ-Decalactone—One of Constituents of Volatiles in Cultured Broth of Sporobolomyces Odorus
5. Labuda, I. (2009). Flavor Compounds. Encyclopedia of Microbiology, Academic Press. [3rd ed.]. Applied Microbiology: Industrial.10.1016/B978-012373944-5.00148-6 ↗
6. Biotechnological production of flavour-active lactones10.1007/BFb0102067 ↗
7. Systematic Approach for the Development of Fruit Wines from Industrially Processed Fruit Concentrates, Including Optimization of Fermentation Parameters, Chemical Characterization and Sensory Evaluation10.1016/j.lwt.2015.02.020 ↗
8. Jackson, R.S. (2017). Chapter 3—Olfactory Sensations. Wine Tasting, Elsevier.10.1016/B978-0-12-801813-2.00003-3 ↗
9. Applied Biocatalysis for the Synthesis of Natural Flavour Compounds—Current Industrial Processes and Future Prospects10.1023/B:BILE.0000019576.80594.0e ↗
10. Industrial Riboflavin Fermentation Broths Represent a Diverse Source of Natural Saturated and Unsaturated Lactones10.1021/acs.jafc.9b01154 ↗
11. Biochemistry of Lactone Formation in Yeast and Fungi and Its Utilisation for the Production of Flavour and Fragrance Compounds10.1007/s00253-010-2945-0 ↗
12. Characterization and Evaluation of Coconut Aroma Produced by Trichoderma Viride EMCC-107 in Solid State Fermentation on Sugarcane Bagasse10.1016/j.ejbt.2014.10.006 ↗
13. Biosynthesis and Chemical Diversity of β-Lactone Natural Products10.1039/C8NP00052B ↗
14. Generation of Flavors and Fragrances Through Biotransformation and De Novo Synthesis10.1007/s11947-018-2180-8 ↗
15. Merillon, J.-M., and Ramawat, K.G. (2015). Lactone Formation in Yeast and Fungi. Fungal Metabolites, Springer International Publishing.10.1007/978-3-319-19456-1 ↗
16. Gamma-Valerolactone, a Sustainable Platform Molecule Derived from Lignocellulosic Biomass10.1039/c3gc37065h ↗
17. Biotechnological Production of γ-Decalactone, a Peach like Aroma, by Yarrowia Lipolytica10.1007/s11274-016-2116-2 ↗
18. Ricin Poisoning: A Comprehensive Review10.1001/jama.294.18.2342 ↗
19. Castor Oil: Properties, Uses, and Optimization of Processing Parameters in Commercial Production10.4137/LPI.S40233 ↗
20. A Single-Host Fermentation Process for the Production of Flavor Lactones from Non-Hydroxylated Fatty Acids10.1016/j.ymben.2019.08.009 ↗
21. Sánchez, G., Venegas-Calerón, M., Salas, J.J., Monforte, A., Badenes, M.L., and Granell, A. (2013). An Integrative “Omics” Approach Identifies New Candidate Genes to Impact Aroma Volatiles in Peach Fruit. BMC Genom., 14.10.1186/1471-2164-14-343 ↗
22. Sánchez-Sevilla, J.F., Cruz-Rus, E., Valpuesta, V., Botella, M.A., and Amaya, I. (2014). Deciphering Gamma-Decalactone Biosynthesis in Strawberry Fruit Using a Combination of Genetic Mapping, RNA-Seq and EQTL Analyses. BMC Genom., 15.10.1186/1471-2164-15-218 ↗
23. Metabolic Engineering of Ashbya Gossypii for Deciphering the de Novo Biosynthesis of γ-Lactones10.1186/s12934-019-1113-1 ↗
24. Catabolism of Hydroxyacids and Biotechnological Production of Lactones by Yarrowia Lipolytica10.1007/s00253-002-1207-1 ↗
25. Production of γ-Decalactone and 4-Hydroxy-Decanoic Acid in the Genus Sporidiobolus10.1016/S0922-338X(98)80056-1 ↗
26. The Use of the Lactone Motif in Chemical Communication10.1039/C5NP00006H ↗
27. Ward, R.S., and Jones, R.L. (2017). Polyurethanes and Silicone Polyurethane Copolymers. Comprehensive Biomaterials II., Elsevier.10.1016/B978-0-08-100691-7.00179-8 ↗
28. γ-Valerolactone—A Sustainable Liquid for Energy and Carbon-Based Chemicals10.1039/B712863K ↗
29. Singh, G.S. (2020). Carbohydrate-based antibiotics: Opportunities and challenges. Carbohydrates in Drug Discovery and Development, Elsevier.10.1016/B978-0-12-816675-8.00013-0 ↗
30. A Rapid Esterification by Means of Mixed Anhydride and Its Application to Large-Ring Lactonization10.1246/bcsj.52.1989 ↗
31. An Effective Method for the Synthesis of Carboxylic Esters and Lactones Using Substituted Benzoic Anhydrides with Lewis Acid Catalysts10.1016/j.tet.2003.12.013 ↗
32. Efficient and Mild Lactonization Method for the Synthesis of Macrolides10.1021/ja00824a073 ↗
33. A New Environmentally Benign Catalytic Process for the Asymmetric Synthesis of Lactones: Synthesis of the Flavouringδ-Decalactone Molecule10.1002/adsc.200303234 ↗
34. Production of Odoriferous γ Lactones by Fusarium Poae
35. Characterization of the Major Aroma Constituent of the Fungus Trichoderma Viride10.1021/jf60180a010 ↗
36. Microbial Production of Natural δ-Decalactone and δ-Dodecalactone from the Corresponding α, β- Unsaturated Lactones in Massoi Bark Oil10.1007/BF00172180 ↗
37. Biosynthesis of Flavor Compounds by Microorganisms Odorous Constituents of Polyporus durus (Basidiomycetes)
38. Neutral Constituents of Volatiles in Cultured Broth of Sporobolomyces odurus10.1080/00021369.1973.10861068 ↗
39. δ-Lactones Produced by Sporobolomyces odorus
40. Chirality of the γ-Lactones Produced by Sporidiobolus salmonicolor Grown in Two Different Media10.1002/(SICI)1520-636X(1997)9:7<667::AID-CHIR5>3.0.CO;2-4 ↗
41. Microbial Biocatalysis in the Generation of Flavor and Fragrance Chemicals10.1146/annurev.mi.48.100194.004013 ↗
42. Studies on the Biosynthesis of Aliphatic Lactones in Sporobolomyces odorus. Conversion of (S)- and (R,S)-13-Hydroxy-(Z,E)-9,11-Octadecadienoic Acid into Optically Pure (R)-.Delta.-Decalactone10.1021/jo00033a007 ↗
43. Biosynthesis of ?-Jasmin Lactone ( = (Z)-Dec-7-Eno-5-Lactone) and (Z,Z)-Dodeca-6,9-Dieno-4-Lactone in the Yeast Sporobolomyces odorus10.1002/hlca.19960790806 ↗
44. Biosynthesis of (R)-γ-Decanolactone in the Yeast Sporobolomyces Odorus10.1021/jf950570w ↗
45. Tressl, R., Haffner, T., Lange, H., and Nordsieck, A. (1996). Formation of γ- δ-lactones by different biochemical pathways. Flavour Science, Elsevier.10.1533/9781845698232.3.139 ↗
46. Stereospecific Metabolism of Isomeric Epoxyoctadecanoic Acids in the Lactone-Producing Yeast Sporidiobolus salmonicolor10.1007/s11745-998-0179-9 ↗
47. Production, Identification, and Toxicity of (Gamma)-Decalactone and 4-Hydroxydecanoic Acid from Sporidiobolus spp.10.1128/aem.62.8.2826-2831.1996 ↗
48. Biosynthesis of Dodecano-4-Lactone in Ripening Fruits: Crucial Role of an Epoxide-Hydrolase in Enantioselective Generation of Aroma Components of the Nectarine (Prunus Persica Var. Nucipersica) and the Strawberry (Fragaria ananassa)10.1002/hlca.19960790521 ↗
49. An Oleate 12-Hydroxylase from Ricinus Communis, L. Is a Fatty Acyl Desaturase Homolog10.1073/pnas.92.15.6743 ↗
50. Metabolism of Hydroxy Fatty Acids: II. Intermediates of the Oxidative Breakdown of Ricinoleic Acid by Genus Candida10.1093/oxfordjournals.jbchem.a127827 ↗
51. Biotechnological Production of Flavours and Fragrances10.1007/s002530051129 ↗
52. Yeast: A New Oil Producer?10.1051/ocl.2012.0426 ↗
53. Peroxisomal Beta-Oxidation Activities and Gamma-Decalactone Production by the Yeast Yarrowia Lipolytica10.1007/s002530051172 ↗
54. Evaluation of Acyl Coenzyme A Oxidase (Aox) Isozyme Function in the n -Alkane-Assimilating Yeast Yarrowia Lipolytica10.1128/JB.181.17.5140-5148.1999 ↗
55. Involvement of Acyl Coenzyme a Oxidase Isozymes in Biotransformation of Methyl Ricinoleate into Gamma-Decalactone by Yarrowia Lipolytica10.1128/AEM.66.3.1233-1236.2000 ↗
56. Role of β-Oxidation Enzymes in γ-Decalactone Production by the Yeast Yarrowia Lipolytica10.1128/AEM.67.12.5700-5704.2001 ↗
57. Optimization of Yarrowia Lipolytica’s β-Oxidation Pathway for γ-Decalactone Production
58. Expression of POX2 Gene and Disruption of POX3 Genes in the Industrial Yarrowia Lipolytica on the γ-Decalactone Production10.1016/j.micres.2011.10.003 ↗
59. Lipase Induction in Yarrowia Lipolytica for Castor Oil Hydrolysis and Its Effect on γ-Decalactone Production10.1007/s11746-011-1987-5 ↗
60. Impact of Lipase-Mediated Hydrolysis of Castor Oil on γ-Decalactone Production by Yarrowia Lipolytica10.1007/s11746-013-2231-2 ↗
61. Interaction of Odorous Lactones with Phospholipids: Implications in Toxicity towards Producing Yeast Cells10.1023/A:1021129800080 ↗
62. Interaction of an Odorant Lactone with Model Phospholipid Bilayers and Its Strong Fluidizing Action in Yeast Membrane10.1016/S0168-1605(02)00150-2 ↗
63. Mechanisms Underlying the Toxicity of Lactone Aroma Compounds towards the Producing Yeast Cells10.1046/j.1365-2672.2003.01828.x ↗
64. Fed-Batch versus Batch Cultures of Yarrowia Lipolytica for γ-Decalactone Production from Methyl Ricinoleate10.1007/s10529-011-0824-0 ↗
65. Production of γ-Decalactone by Yarrowia lipolytica: Insights into Experimental Conditions and Operating Mode Optimization: Production of γ-Decalactone by Yarrowia Lipolytica10.1002/jctb.4349 ↗
66. Decalactone Production by Yarrowia Lipolytica under Increased O2 Transfer Rates10.1007/s10529-005-2517-z ↗
67. Oxygen Mass Transfer in a Biphasic Medium: Influence on the Biotransformation of Methyl Ricinoleate into γ-Decalactone by the Yeast Yarrowia lipolytica10.1016/j.bej.2007.02.002 ↗
68. γ-Decalactone Production by Trichoderma Harzianum in Stirred Bioreactors10.1021/bp960096u ↗
69. Growth of and Production of γ-Decalactone by Sporobolomyces Odorus in Jar Fermentors as Affected by PH, Aeration and Fed-Batch Technique10.1016/0922-338X(95)93219-A ↗
70. Fatty Acid Accumulation in the Yeast Sporidiobolus salmonicolor during Batch Production of γ-Decalactone10.1016/S0378-1097(97)00048-7 ↗
71. Isolation and Characterisation of 8-Hydroxy-3Z,5Z-Tetradecadienoic Acid, a Putative Intermediate in Pichia Guilliermondii γ-Decalactone Biosynthesis from Ricinoleic Acid10.1016/S0378-1097(02)00488-3 ↗
72. Stereochemistry of the Biogeneration of C-10 and C-12 Gamma Lactones in Yarrowia lipolytica and Pichia ohmeri10.1007/BF01021639 ↗
73. Improvement of γ-Decalactone Production by Stimulating the Import of Ricinoleic Acid and Suppressing the Degradation of γ-Decalactone in Saccharomyces Cerevisiae10.1080/10242422.2017.1289182 ↗
74. Production of γ-Decalactone by a Psychrophilic and a Mesophilic Strain of the Yeast Rhodotorula aurantiaca10.1007/s12010-008-8297-x ↗
75. The Utilization of Gum Tragacanth to Improve the Growth of Rhodotorula aurantiaca and the Production of γ-Decalactone in Large Scale10.1007/s12010-009-8739-0 ↗
76. Engineered High Content of Ricinoleic Acid in Fission Yeast Schizosaccharomyces pombe10.1007/s00253-012-3959-6 ↗
77. Production of 10-Hydroxystearic Acid from Oleic Acid by Whole Cells of Recombinant Escherichia Coli Containing Oleate Hydratase from Stenotrophomonas maltophilia10.1016/j.jbiotec.2012.01.002 ↗
78. New Biotransformation Process for Production of the Fragrant Compound γ-Dodecalactone from 10-Hydroxystearate by Permeabilized Waltomyces Lipofer Cells10.1128/AEM.02602-12 ↗
79. Increased Production of γ-Lactones from Hydroxy Fatty Acids by Whole Waltomyces Lipofer Cells Induced with Oleic Acid10.1007/s00253-013-5089-1 ↗
80. Biochemical Characterization and FAD-Binding Analysis of Oleate Hydratase from Macrococcus caseolyticus10.1016/j.biochi.2011.12.011 ↗
81. γ-Decalactone Production by Yarrowia Lipolytica and Lindnera Saturnus in Crude Glycerol10.1080/10826068.2017.1286601 ↗
82. Chiral γ-Lactones from Fusarium Poae10.1007/BF01192012 ↗
83. Chirality of the γ-Lactones Formed by Fusarium Poae INRA10.1002/chir.530050520 ↗
84. Enantiodifferentiation of Four γ-Lactones Produced by Penicillium roqueforti10.1002/(SICI)1520-636X(1998)10:9<786::AID-CHIR2>3.0.CO;2-8 ↗
85. Major Contribution of the Ehrlich Pathway for 2-Phenylethanol/Rose Flavor Production in Ashbya Gossypii10.1111/1567-1364.12172 ↗
86. Tuning Single-Cell Oil Production in Ashbya Gossypii by Engineering the Elongation and Desaturation Systems: Engineering of Single-Cell Oil in Ashbya Gossypii10.1002/bit.25245 ↗
87. Ashbya gossypii beyond Industrial Riboflavin Production: A Historical Perspective and Emerging Biotechnological Applications10.1016/j.biotechadv.2015.10.001 ↗
88. New Biotechnological Applications for Ashbya Gossypii: Challenges and Perspectives10.1080/21655979.2016.1234543 ↗
89. Microbial Lipids from Industrial Wastes Using Xylose-Utilizing Ashbya gossypii Strains10.1016/j.biortech.2019.122054 ↗
90. β-Lactone Synthetase Found in the Olefin Biosynthesis Pathway10.1021/acs.biochem.6b01199 ↗
91. Hiblot, J., Gotthard, G., Elias, M., and Chabriere, E. (2013). Differential Active Site Loop Conformations Mediate Promiscuous Activities in the Lactonase SsoPox. PLoS ONE, 8.10.1371/journal.pone.0075272 ↗
92. The Emergence of Adaptive Laboratory Evolution as an Efficient Tool for Biological Discovery and Industrial Biotechnology10.1016/j.ymben.2019.08.004 ↗
93. Improved Riboflavin Production with Ashbya Gossypii from Vegetable Oil Based on 13C Metabolic Network Analysis with Combined Labeling Analysis by GC/MS, LC/MS, 1D, and 2D NMR10.1016/j.ymben.2018.04.005 ↗