Overview of the Biotransformation of Limonene and α-Pinene from Wood and Citrus Residues by Microorganisms
Abstract
:1. Introduction
2. A Brief Description of Terpenes
3. Recent Advances in Biotransformation of Terpenes: Study Case of Limonene and Alpha Pinene
3.1. Limonene Biotransformation
3.2. Biotransformation of α-Pinene
4. Avenues and Approaches for Improving the Biotransformation of Limonene and Alpha Pinene
4.1. Application of Solid-State Fermentation for Biotransformation from Filamentous Fungi
4.2. Selection of Microorganisms
4.3. Pathways of Terpenes Biotransformation
4.3.1. Bicyclic Monoterpenes
4.3.2. Monocyclic Monoterpenes
4.4. Improvements in Physical Pretreatment of Wood and Citrus Residues
4.4.1. Pretreatment and Conditioning
4.4.2. Thermal Pretreatment
4.4.3. Chemical Pretreatment
4.4.4. Biological Pre-Treatments
4.4.5. Extrusion
5. Existing Technology for Terpenes Extraction
5.1. Steam Distillation
5.2. Solvent Extractions
5.3. New Extraction Methods
5.3.1. Microwave-Assisted Extraction
5.3.2. CO2 Extraction or Supercritical Fluid Extraction
5.3.3. Subcritical Water Extraction
Extraction Methods | Principle | Advantages and Disadvantages | Reference |
---|---|---|---|
Steam distillation | The forest or agricultural residue is in direct contact with steam, which is then condensed. Recovery takes place in a separator, where the volatile molecules are dispersed in water. | Méthode très simple Very simple method No energy expenditure | [74] |
Solvent extraction | The volatile molecules are separated from the solvent by evaporation of the solvent at high temperatures. | Efficient, slow and costly method Requires high temperatures (degradation of some constituents of volatile molecules) | [75] |
Hydrodistillation | The residual material is submerged in water, which is then heated to boiling point. After passing through the cooler, the mixture is collected in an essencier. | Efficient, but slow method for 100 g (4 h) High water consumption | [76] |
Supercritical fluid extraction | Extraction requires a supercritical fluid (CO2 in the presence of an organic solvent). | Efficient, low-cost method No oxidative degradation of lipids | [68] |
Ultrasonic extraction | Sound waves exert vibrations on plant cell walls, improving extraction. | Reduced extraction time | [63] |
Microwave extraction | The residual material is heated from the inside out, increasing the water pressure inside the cells and causing the cells to burst and spill their contents into the outside environment. | Environmental efficiency Fast method Saves time, water and residual solvent | [70] |
Hydrodistillation combined with microwaves | For 100 g of plant material, this method requires power (1200 watts) and duration 15 min | Good yield, fast (75 min), low cost | [69] |
6. Conclusions
Author Contributions
Funding
Institutional Review Board Statement
Informed Consent Statement
Data Availability Statement
Conflicts of Interest
References
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Essence | Parameters | Monoterpene | Oxygenated Monoterpene | Sesquiterpene | Esters | References |
---|---|---|---|---|---|---|
Balsam fir | Concentration | 84.9% | 1.3% | 0.6% | 9.1% | [10,11] |
major compound | α-Pinene | |||||
β-pinene | α-Tepeniol | β-caraphyllene | Bornyl acetate | |||
Limonene | ||||||
Black spruce | Concentration | 63.5% | 2.6% | β-caraphyllene | Bornyl acetate | [10,11] |
major compound | α-Pinene | |||||
β-pinene | α-tepeniol | |||||
ϒ-3-carene | 1,8-cineole | |||||
Jack pine | Concentration | 85.9% | 2.7% | 0.2% | 8.2% | [10,11] |
major compound | α-pinene | α-tepeniol | α-tepeniol | Bornyl acetate | ||
camphene | 1,8-cineole | 1,8-cineole | ||||
Citrus terpenes | major compounds | Limonene 95% | ||||
α-pinene 2.5% | [12] | |||||
camphene 2% | ||||||
β-myrcene 0.5% |
Terpene Substrate | Biotransformation Product | Strains | Chemical Name | Odour | Application | Reference |
---|---|---|---|---|---|---|
LIMONENE | α-Terpineol | Pseudomonas fluorescens | p-Menth-1-en-8-ol | lilac | Antioxidant activity, Anti-inflammatory activity, Antimicrobial activity: Activity against A.niger, Staphylococcus epidermidis, Cytostatic and cytocidal effects towards Goetrichum citri-aurantii. | [6] |
Carveol | Rhodococcus opacus; Rhodococcus erythropolis PWD8; Pleurotus sapidus; Aspergillus cellulosae M-77 | p-Mentha-6,8-dien-2-ol | spearmint | Flavouring agent; food additive. | [31] | |
Carvone | Rhodococcus opacus; Rhodococcus eythropolis PWD8; Penicilium digitarium; Pleurotus sapidus | p-mentha-1(6),8-dien-2-one | Mint aroma | Flavouring agent: flavour chewing gum and mint candies, provide aromas in personal-care products, air fresheners, and aromatherapy oils. | [31] | |
Perillic acid or perillyl alcohol | Pseudomonas putida DSM 12264; Aspergillus cellulosae M-77; Mycobacterium sp. HXN-150 | (4R)-4-prop-1-en-2-ylcyclohexene-1-carboxylic acid | Exhibit antimicrobial properties; Ingredients in cleaning products; Mosquito repellent when applied to the skin. | [31] | ||
Terpene Substrate | ||||||
α-PINENE | Verbenol | Aspergillus niger | 4,6,6-Trimethyl-bicyclo(3.1.1)hept-3-en-2-one | Balsamic aroma | used in fragrance formulation of soft drinks, soups used as important intermediates in cosmetics and pharmaceutical industries used as flavour in food, such as in meats, sausages and ice cream used as material to synthesise chemicals, such as citral. | [32] |
Verbenone | 4,6,6-Trimethylbicyclo [3.1.1]heptan-3-one | minty spicy aroma | Used for insect control particularly against beetles as Dendroctonus frontalis; Used also in perfumery, aromatherapy, herbal teas and herbal remedies. The L-isomer is used as a cough suppressant under the name of levoverbenone. Verbenone may also have had antimicrobial properties. |
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Ndao, A.; Adjallé, K. Overview of the Biotransformation of Limonene and α-Pinene from Wood and Citrus Residues by Microorganisms. Waste 2023, 1, 841-859. https://doi.org/10.3390/waste1040049
Ndao A, Adjallé K. Overview of the Biotransformation of Limonene and α-Pinene from Wood and Citrus Residues by Microorganisms. Waste. 2023; 1(4):841-859. https://doi.org/10.3390/waste1040049
Chicago/Turabian StyleNdao, Adama, and Kokou Adjallé. 2023. "Overview of the Biotransformation of Limonene and α-Pinene from Wood and Citrus Residues by Microorganisms" Waste 1, no. 4: 841-859. https://doi.org/10.3390/waste1040049