Current Advances in the Bacterial Toolbox for the Biotechnological Production of Monoterpene-Based Aroma Compounds
Abstract
:1. The Importance of Aroma Compounds in Industry
1.1. Scope of the Review
1.2. Aroma Compounds in Nature: Monoterpenes and Monoterpenoids
2. Catalysis Mediated by Biological Systems
2.1. Bacterial Adaptation to the Hydrophobicity of Monoterpene Substrates
- I.
- II.
- III.
- They may alter the profile of phospholipid head groups, which is predicted to influence the physical and chemical properties of the membrane (e.g., charge and melting point) [31].
- IV.
- They may swiftly increase cell surface hydrophobicity by altering the composition of the lipopolysaccharide layer (e.g., complete loss of B band lipopolysaccharide), and generate outer membrane vesicles (OMVs). Although this ubiquitous mechanism has not been extensively reported as a response to hydrophobic stress, several studies with solvent-tolerant P. putida strains have shown the induction of vesiculation mediated by alkanes and alkanols ([36] and references therein). This strategy may provide an enhanced ability for protective cell attachment, aggregation and biofilm formation, as well as for partitioning the hydrocarbon stressor in vesicles ([37] and references therein).
- V.
- Several bacterial strains (e.g., Pseudomonas spp., Vibrio spp., strains of Methylococcus capsulatus, Alcanivorax borkumensis and Colwellia psychrerythraea) employ a fifth adaptive mechanism by isomerizing cis-unsaturated fatty acids to trans-unsaturated acyl chains ([37] and references therein). Cis-unsaturated acyl chains comprise a bend of 30°, which disturbs the ordered fatty acid packing, increasing fluidity, allowing denser packing and promoting an increase in membrane stiffness to counteract excessive fluidity ([37] and references therein). This membrane cis-to-trans isomerization is performed by cis/trans isomerases, and since it is dependent on neither energy nor on the de novo synthesis of fatty acid molecules, this mechanism is considered a rapid short-term response to chemical stress.
2.2. Mechanisms for the Bacterial Transformation of the Hydrocarbon Backbone
2.2.1. Molecular Mechanism for the Catabolism of the Unsaturated Hydrocarbon Backbone
2.2.2. Molecular Mechanism for the Catabolism of the Branched Hydrocarbon Backbone
2.3. Nature’s Reservoir of Bacterial Biocatalysts for Industrially Relevant Monoterpenes
2.3.1. Pinene Isomers: A Bicyclic Precursor
2.3.2. Limonene: The Monocyclic Precursor
2.3.3. β-Myrcene: The Versatile Acyclic Precursor
3. Exploiting the Biotechnological Potential of Monoterpene-Catabolizing Enzymes
3.1. Metagenomics Approaches May Expand the Bacterial Toolbox for the Production of Monoterpene-Based Aroma Compounds
3.2. Holistic Approaches Are the Framework for Monoterpene Biocatalysis À La Carte
3.3. Coupling the Bacterial Synthesis of Monoterpene Precursors with the Oxidative Biocatalysis into Aroma Compounds
4. Outlook and Final Considerations
Supplementary Materials
Author Contributions
Funding
Institutional Review Board Statement
Informed Consent Statement
Data Availability Statement
Conflicts of Interest
References
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Compound | Aroma | Observations of Biotech Production |
---|---|---|
Phenolic aldehydes | ||
vanillin | vanilla aroma | biotech production established by, e.g., Evolva-IFF, Solvay, Mane, Shangai Apple, BASF, Isobionics |
safranal | saffron aroma, sweet, spicy, floral odor with a bitter taste | biotech production announced by, e.g., Evolva |
Lactones | ||
γ-decalactone | fruity, peach-like aroma | biotech production established by, e.g., BASF, Symrise |
γ-undecalactone | fruity, sweat peach-like aroma | - |
Ketones | ||
2-heptanone | fruity, cinnamon, banana-like | - |
α- and β-Ionone | woody, raspberry-type, floral, violet-like odor | - |
nootkatone | citrusy notes and grapefruit-like aroma | biotech production established by, e.g., Allylix (Evolva), Isobionics, Oxford Biotrans |
Alcohols | ||
1-octen-3-ol | sweet, earthy, herbaceous floral notes, reminiscent of lavender | - |
Carboxylic acids | ||
citric acid | acid taste; odorless | - |
Esters | ||
ethyl butanoate | sweet and pineapple-like aroma | - |
Essential Oils | ||
orange peel oil | orange aroma | - |
lemon peel oil | lemon aroma | - |
eucalyptus oil | camphoraceous odor, spicy, cooling taste | - |
peppermint oil | odor of peppermint, cooling, minty, menthol, sweet taste | - |
spearmint oil | minty, carvone-like, cooling, candy, spicy | - |
Monoterpenes | ||
α-pinene | terpy, citrus and spicy, woody pine and turpentine-like with a slight cooling camphoraceous nutmeg-like note | - |
β-pinene | cooling, woody, piney and turpentine-like with a fresh minty, eucalyptus and camphoraceous note | - |
1,8-cineole | cooling, fresh, oily, green, spicy, pine-like | - |
limonene | (+)-limonene has an orange-like odor (−)-limonene has a more harsh turpentine-like odor with a lemon note | - |
(−)-menthol | minty, coolant odor | - |
menthone | minty, cooling, sweet, peppermint, camphoraceous aroma with a green herbal anise nuance | - |
carvone | (R)-(−)-carvone has a spearmint aroma (S)-(+)-carvone has a caraway aroma | - |
α-terpineol | pine odor, floral aroma | - |
β-myrcene | terpy, herbaceous, woody odor with a mango-like nuance. | - |
linalool | floral, fresh, sweet, citrus-like aroma | - |
citronellol | rose-like scent | - |
citral | lemon, peely, citrus, floral with woody and candy notes. | - |
geraniol | rose-like, sweet, fruity aroma | - |
Sesquiterpenes | ||
α-farnesene | dry woody, green leafy, herbal and floral nuance | biotech production established by, e.g., Amyris-Antibióticos S.A |
(+)-valencene | sweet, fresh, grapefruit-like aroma | biotech production established by, e.g., Allylix (Evolva), Isobionics |
Whole-Cell Biocatalyst | Substrate | Product | Ref. |
---|---|---|---|
Pseudomonas sp. TK2102 | Eugenol | vanillin | [42] |
(JP patent 5227980) | |||
Pseudomonas putida ATCC55180 | Eugenol | vanillin | [43] |
(US patent 5128253) | Ferulic acid | ||
Pseudomonas sp. NCIB 11671 | α- and β-Pinene | (−)-carvone (spearmint aroma) | [44] |
(US patent 4495284) | |||
Enzymatic Biocatalyst | Substrate | Product | Ref. |
Commercial lipase AK from Pseudomonas fluorescens (Amano Enzyme Inc.) | (±)-menthol, | (−)-menthyl acetate for the production of (−)-menthol | [45] |
(±)-neomenthol, | |||
(±)-neoisomenthol, | |||
(±)-isomenthol | |||
Commercial lipase PS from Burkholderia cepacia (Amano Enzyme Inc.) | (±)-isopulegol isomers and vinyl acetate | (−)-isopulegol acetate for the production of (−)-isopulegol | [46] |
Commercial lipase PS from Burkholderia cepacia (Amano Enzyme Inc.) | (±)-mentholand vinyl acetate | (+)-menthol and(−)-menthyl acetate for the production of (−)-menthol | [46] |
Commercial esterase from Bacillus subtilis ECU0554 | (±)-menthol esters | (−)-menthol | [47] |
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Soares-Castro, P.; Soares, F.; Santos, P.M. Current Advances in the Bacterial Toolbox for the Biotechnological Production of Monoterpene-Based Aroma Compounds. Molecules 2021, 26, 91. https://doi.org/10.3390/molecules26010091
Soares-Castro P, Soares F, Santos PM. Current Advances in the Bacterial Toolbox for the Biotechnological Production of Monoterpene-Based Aroma Compounds. Molecules. 2021; 26(1):91. https://doi.org/10.3390/molecules26010091
Chicago/Turabian StyleSoares-Castro, Pedro, Filipa Soares, and Pedro M. Santos. 2021. "Current Advances in the Bacterial Toolbox for the Biotechnological Production of Monoterpene-Based Aroma Compounds" Molecules 26, no. 1: 91. https://doi.org/10.3390/molecules26010091