Bio-Availability, Anticancer Potential, and Chemical Data of Lycopene: An Overview and Technological Prospecting
Abstract
:1. Lycopene Bio-availability
2. Production and Extraction Process
3. Chemical Characterization
3.1. UV–Vis
3.2. Fluorescence
3.3. High-Performance Liquid Chromatography (HPLC)
3.4. Fourier Transform Infrared (FTIR)
3.5. Mass Spectrometry
3.6. Nuclear Magnetic Resonance (NMR)
3.7. X-ray Diffraction (XRD)
3.8. Differential Scanning Calorimetry (DSC)
4. Quantitative Analysis
4.1. Extraction
4.2. Biosynthesis
4.3. Supercritical Carbon Dioxide (SC-CO2)
4.4. UV–Vis and HPLC
5. Antioxidant Activity
6. Antimicrobial Activity
7. Anti-Inflammatory Assays
8. Anticancer Pathways
9. Lycopene Bio-accessibility and Bio-availability—Novel Technologies
10. Patent Databases
11. Conclusions
Author Contributions
Funding
Acknowledgments
Conflicts of Interest
References
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Technique | Solvent/Mobile Phase/Flow Rate | Device | Temperature/ Pressure/Time/ V/Hz/rpm | Lycopene Source/ Carotenoid Extracted | References |
---|---|---|---|---|---|
Extraction | Hexane | Soxhlet extractor | 37 °C/6 h | Tomato peel and seed/ cis and trans-lycopene | [19] |
* SC-CO2/1 mL·min−1 | SFT 110 extractor | 40 and 80 °C/30 and 50 MPa/30, 45, 60, 90, 120, 180, 240 min | |||
Hexane/Acetone/Ethanol (2:1:1) | Vortex | 2 h | |||
Washed in 0.1 M NaCl | Tomato peel and seed/ Lycopene and β-carotene | [22] | |||
OH pre-treatment | 55 °C/1 min | ||||
Water/Ethanol (70%) (1:6 w/v) & | Thermal extraction | 55 °C/15 min | |||
Water/Ethanol (1:6 w/v) & + OH solution | |||||
OH application | Ohmic heating (OH) technology (6–11 V·cm−1) pre-treatment | 0–100 °C/30 min/ 60–280 V/ 25 kHz | |||
* SC-CO2/1 L·min−1 | SFT 110 extractor | 60 °C and 40 MPa/ 30, 45, 60, 90, 120, 180, 240 min | Tomato peel and seed/ Highest cis-lycopene content | [23] | |
Hexane | Soxhlet extractor/0.22 µm hydrophobic PTFE | 12 h | Tomato peel and seed/ Lycopene | [24] | |
Olive oil | Maceration (15 to 150 min)/Magnetic stirrer/Box–Behnken | 40–80 °C/ 200–400 rpm | |||
Methanol/Ethyl acetate/ Petroleum ether (1:1:1, v/v/v) | Tomato peel and seed from 10 varieties/ Lycopene, β-carotene, and lutein | [25] | |||
30% Methanolic potassium hydroxide | Room temperature /6 h | ||||
Saturated saline solution/ Diethyl ether/ Distilled water | Washed | ||||
Dry over anhydrous sodium sulfate | Rotary evaporator R-124 | 35 °C | |||
PEF (pre-treatment)1,3; 5 kV·cm−1/0.012 kJ·kg−1, 0.160 kJ·kg−1, 0.475 kJ·kg−1/10 Hz/20 μs | 20 ± 2 °C | Tomato peels/ cis and all trans-lycopene | [26] | ||
Acetone (1:40 w/v) & | Extraction flask | 25 °C/0–24 h /160 rpm | |||
Ethyl lactate (1:40 w/v) & | |||||
Ethyl acetate | Thermal extraction | 75 °C/1 or 2 h | Plum tomato peels/ cis and all trans-lycopene | [27] | |
Ultrasounds | Approximately 0 °C/30 min | ||||
Magnesium carbonate (20%) (sample/solution 1:1) | Orbital shaker | 25 °C/2 h | Tomato peels/ Lycopene | [3] | |
n-hexane/Acetone (3:1) | Ultrasonic | 50 °C/30 min (10 times) | |||
Centrifuge | 10 °C/10 min | ||||
Reduced volume | 40 °C/Low pressure | ||||
Technique | Substrate | Device | Biological Strain | Carotenoid Produced | References |
Biosynthesis | Isopropyl-β-d-thiogalactoside (IPTG) as inducer | Shaking flask (37 °C and 200 rpm) | E. coli | Lycopene | [20] |
Glucose | Shake flask (30 °C, 300–600 rpm) | S. cerevisiae | Lycopene | [21] | |
Glucose + Glycerol | Shake flask (37 °C, pH = 7.2, 48 h) | Escherichia coli R122 | Lycopene | [1] | |
Glucose | |||||
Oleic acid | Bioreactor (37 °C, pH = 7.2, 48 h) | Escherichia coli FA03-PM | |||
Glucose | |||||
Glucose + oleic acid + yeast extract | |||||
Glucose + waste cooking oil + yeast extract | |||||
Lactic acid | Flask fermentation (120 h) | B. trispora NRRL 2895 (+) and N6 (−) | Lycopene and β-carotene | [8] |
Technique | Mobile Phase | Device | Carotenoid Results | References |
High-performance liquid chromatography (HPLC) | Acetonitrile/Methanol/ Hexane/Dichloromethane /Ammonium acetate (55:22:11.5:11.5:0.02) (v/v/v/v/w) Isocratic performance | C30 RPAQUEOUS (5 μm; 4.6 mm × 250 mm) DAD detector | all-trans-lycopene, 5cis, 13cis-lycopene, and β-carotene | [28] |
all-trans-lycopene, 5cis, and 13cis-lycopene | [16] | |||
all-trans-lycopene, and other carotenoids | [12] | |||
Methanol/ Methyl butyl ether/ Ethyl acetate (5:4:1) | C30 YMC (5 μm; 4.6 mm × 250 mm) | 15cis, 13cis, 9cis, 5cis, other cis isomers, and all-trans-lycopene | [19] | |
A: Ethyl acetate B: Acetonitrile/water (90:10) Gradient performance | C18 Vydac 201TP54 C (250 × 4.6 mmm) + C18 pre-column DAD detector | Total carotenoids in β-carotene and lycopene | [22] | |
Methanol/Methyl butyl ether/Ethyl acetate (50:40:10) | C30 YMC (5 μm; 4.6 mm × 250 mm) | cis and trans-lycopene | [23] | |
Acetonitrile/ Dichloromethane (75:25; v/v) | C18 Eclipse XDB (3.5 μm; 4.6 mm × 250 mm) DAD detector | Lycopene | [24] | |
A: Methanol/Water (98:2) B: Methanol/Water (95:5) C: MTBE Gradient performance | C30 YMC (3 μm, 250 × 4.6 mm) + C30 guard column (20 × 4.6 mm) Column heater at 20 °C DAD detector | 15cis, 13cis, 9cis, 5cis, di cis isomers, and all-trans-lycopene | [27] | |
A: Acetonitrile/water (9:1, v/v) + 0.25% Triethylamine B: Ethyl acetate + 0.25% Triethylamine Gradient performance | C18 Nucleodur 300-5 (5 μm; 4.6 × 250 mm) DAD detector | Lycopene, β-carotene, and lutein | [25] | |
Methanol (27%)/ Acetonitrile (23%)/ MTBE (50%) | C30 YMC | all-trans-lycopene,13cis, 9cis, and total cis-lycopene isomers | [6] | |
Acetonitrile/Methanol (10:90, v/v)/9 mM TEA (Triethylamine) | C18 reverse-phase ODS2 (5 μm; 4.6 mm × 150 mm) DAD detector | all-trans-lycopene Undefined carotenoid | [26] | |
A: Acetone/water (75:25, v/v) B: Acetone/Methanol (75:25, v/v) Gradient performance | C18 Zorbax (3 μm; 3 mm × 250 mm) DAD detector | Lycopene | [18] | |
Acetonitrile/Methanol/ Hexane/Dichloromethane /Ammonium acetate (55:22:11.5:11.5:0.02, v:v:v:v:w) | RPAQUEOUS Develosil-C30 (5 µm, 4.6 × 150 mm) | Lycopene isomer Lycopene Other carotenoids | [11] | |
Technique | Solvent | Device | Carotenoid Results | References |
UV–Vis | Chloroform:Ethanol (1:20) | UV–Vis spectrophotometer | all-trans-lycopene | [13] |
Chloroform:Ethanol | UV-1800 spectrophotometer | Lycopene | [16] | |
Water | Lycopene | |||
n-hexane:acetone (3:1) | Spectrophotometer | Lycopene | [3] | |
Acetone | Spectrophotometer | Lycopene | [1] | |
Acetone | V-650 UV–Vis spectrophotometer | Lycopene | [26] | |
Ethyl acetate | Lycopene | |||
Ethanol | UV–Vis spectrophotometer | Lycopene | [11] | |
Technique | Pellet/ATR Accessory | Device | Carotenoid Results | References |
Fourier Transform Infrared (FTIR) | KBr | FTIR | Lycopene | [9] |
KBr | IRAffinity-1 spectrometer | 5cis-lycopene | [28] | |
KBr | FTIR-ATR | Lycopene | [2] | |
Diamond crystal plate | FTIR-ATR | all-trans-lycopene | [13] | |
KBr | FTIR spectrometer | all-trans-lycopene | [6] | |
Technique | Collision Gas (Energy)/ Gas Flow/Temperature /Flow Rate/Capillary Potential | Device/m/z | Carotenoid Results | References |
Mass spectrometry (MS) | 5–18 eV/180 °C/ 4 L·min−1/4 kV | MS/MS Mass spectrometer Electrospray source [M]+ m/z 50–3000 | 5cis-lycopene | [28] |
all-trans-lycopene | ||||
15 eV/180 µL·h−1 Nitrogen gas/200 °C/ 4 L·min−1/4.5 kV | Mass spectrometer ESI source [M]+ m/z 50–1500 | all-trans-lycopene | [13] | |
HRMS ESI [M]+ m/z 100–1000 | Lycopene | [12] | ||
Technique | Solvent/Temperature | Device/ppm | Carotenoid Results | References |
CDCl3 | Discovery Studio 3.5 + B3LYP + 6-311G (d, p) Theoretical NMR + (GIAO)z +TMSa | 5cis-lycopene | [28] | |
400 MHz 1H NMR/0–10 ppm | ||||
400 MHz 13C NMR/0–150 ppm | ||||
D2O/25 ± 0.5 °C | Self-diffusion 1H NMR Avance III 600 MHz | Lycopene | [2] | |
CDCl3 | 1H NMR | all-trans-lycopene | [4] | |
Technique | Å/kV/A | Device/2θ/Steps | Carotenoid Results | Reference |
X-ray diffraction (XRD) | 0.154 nm/40 kV/40 mA | D8 XRD diffractometer/ 4°–45°/0.1° (4°/min) | Lycopene | [10] |
50 kV/100 mA | X-ray diffractometer/ 5°–50°/5 s/step | cis-lycopene isomers | [28] | |
1.54 Å/45 kV/40 mA | D8 XRD diffractometer/ 5°–45°/2°/min | all-trans-lycopene | [6] | |
cis-lycopene | ||||
50 kV/100 mA | X-ray diffractometer/ 3°–50°/5 s/step | cis-lycopene | [16] |
Extract/Structure | Microorganisms | Results | References |
---|---|---|---|
Lycopene (5 µg/mL) from tomato | C. albicans | Antifungal effects against C. albicans by inducing apoptosis via ROS production and mitochondria dysfunction. | [41] |
Carotenoids within PLGA nanoparticles | L. innocua (NRRL B-33076) | The nanoparticles were effective in preventing L. innocua growth. | [42] |
Lycopene oleoresin | E. coli, S. aureus, Salmonella typhi, L. monocytogenes, Bacillus cereus, and B. licheniformis. | Oleoresin can inhibit and prevent the growth of relevant foodborne bacteria. | [43] |
Lycopene extracts from guava and tomato | E. coli, S. aureus, and L. innocua | Extract of lycopene presents MBC values of 20 mg·mL−1. | [28] |
cis/trans-lycopene microsphere from tomato | Salmonella spp., L. monocytogenes, and generic E. coli | The microbial quality of the food samples was not highly affected (< 0.8 log units) during the storage period after the incorporation of lycopene microspheres. | [27] |
Lycopene extract from tomato | Gram (+): S. aureus, B. subtilis, and L. monocytogenes. Gram (-): Pseudomonas aeruginosa, S. typhimurium, E. coli, and Klebsiella pneumonia | Extracts of all cultivars were more effective against S. aureus, moderate antimicrobial activity against K. pneumoniae, P. aeruginosa, E. coli, and S. typhimurium, but Tiny Tim cultivar was the most effective against S. aureus, B. subtilis, L. monocytogenes, and K. pneumonia | [25] |
Delivery System | Encapsulation Method | Results | References |
---|---|---|---|
β-cyclodextrins | A mixture of methylene chloride solution of lycopene with ethanol at 37 °C. | Higher stability against oxidizing agents (AAPH and H2O2). | [52] |
β-cyclodextrins | Lycopene inclusion complexes with β-cyclodextrin were prepared by the precipitation method. | Increased thermal stability, photostability, and antioxidant activity. | [38] |
Nanoliposomes | Sonication of lycopene, soybean phosphatidylcholine, cholesterol, and aqueous solution. | Neuronal protection against cerebral ischemia/reperfusion. Improved therapeutic efficacy and attenuated the cardiotoxicity of the chemotherapy drug doxorubicin. | [53] |
Phospholipid nanoliposomes | Nanospheres of phospholipids with lycopene produced by evaporation and nanoliposomes produced by sonication with the presence of buffer and recovered by centrifugation. | Enhanced antioxidant activity. Prevented reactive oxygen species-induced kidney tissue damage. | [54] |
Double-loaded liposomes | Lycopene, β-cyclodextrins encapsulated with soy lecithin and cholesterol. | Prolonged-release. Improvement of lycopene solubility. Cardioprotective activity tested in vivo. | [55] |
Oil-in-water nano-emulsions | Octenyl succinate anhydride-modified starch mixed with lycopene using high-pressure homogenization and medium-chain triglycerides as carrier oils. | Stable nano-emulsions system with potential application for functional foods. | [2] |
Oil-in-water emulsions | Emulsion of water, pure whey isolate, citric acid, triglycerides, and lycopene created with pressure homogenizer. | Increased lycopene bio-accessibility. System critical for the delivery of lipophilic bioactive compounds in functional drinks. | [56] |
Nanodispersions | Homogenization of lycopene dissolved in dichloromethane, aqueous phase, and Tween 20. | Small-size lycopene nanodispersions. Good stability for application in beverage products. | [57] |
Feed emulsions | Homogenization of tomato powders, maltodextrin, and gum Arabic in aqueous solution and encapsulation made by spray-drying. | Increased lycopene stability. | [58] |
Solid lipid nanoparticles (SLN) | Lycopene-loaded solid lipid nanoparticles using Precirol® ATO 5, Compritol® 888 ATO, and myristic acid by hot homogenization. | Stable after 2 months in an aqueous medium (4 °C). | [59] |
Solid lipid nanoparticles (SLN) | Cold homogenization technique with glyceryl monostearate and lycopene. | Gel with a promising antioxidant therapy in periodontal defects. | [60] |
Solid lipid nanoparticles (SLN) | Homogenization-evaporation technique of lycopene-loaded SLN with different ratios of biocompatible Compritol® 888 ATO and gelucire. | Particles showed in vitro anticancer activity. | [61] |
Nanostructure lipid carriers (NLCs) | Ultrasonication of lycopene with Tween 80 and Poloxamer 188. | Enhanced oral bio-availability. Increased cytotoxicity against human breast tumor cells. | [62] |
Nanostructure lipid carriers (NLCs) | Homogenization and ultrasonication method (aqueous phase with Tween 80, lecithin, and lycopene). | Increased lycopene aqueous solubility. Improved solubility masking tomato aftertaste. Increased homogeneity of fortified orange drink. | [63] |
Nanostructure lipid carriers (NLCs) | Emulsion created with lycopene, a lipid mixture, Tween 80 followed by pressure homogenization. | Biphasic release pattern with fast release initially and a slower afterward. | [6] |
Whey protein isolate nanoparticles | Lycopene loaded whey protein isolate nanoparticles. | Enhance the oral bio-availability of lycopene. Controlled release. Facilitated absorption through the lymphatic pathway. | [17] |
Gelatin nanofibers | A mixture of gelatin from bovine skin and tomato extract is used in electrospinning. | Better retention of lycopene. Better antioxidant activity during 14-days storage. | [64] |
Ionic gelation | Lycopene watermelon concentrate mixed with sodium alginate or pectin. Encapsulation by dipping in CaCl2 and drying under vacuum. | More stable lycopene-rich beads. Good application as natural colorants/antioxidants in different types of food products. | [65] |
Nano-encapsulation | CPCs (Chlorella pyrenoidosa cells) loaded with lycopene into a complex nutraceutical and exogenous. | Feasibility of lycopene encapsulation in the CPCs. Combined the activities of both materials. Novel nutraceuticals to reduce cellular oxidative stress. | [10] |
Nano-emulsion | Lycopene from guava on nanoemulsifying system of natural oils. | Lycopene nano-emulsion with high stability. Significant inhibition of edema formation, suggesting a potential candidate for anti-inflammatory therapy. | [16] |
Lipid-core Nanocapsules | Nano-encapsulation process mixed lycopene extract from guava with polycaprolactone polymer in acetone sorbitan monostearate. | The nanostructure was cytotoxic against cancer cells (human breast adenocarcinoma line MCF-7). | [12] |
Nanoparticle | Polymer nanoparticle fucan-coated based on acetylated cashew gum and lycopene extract from guava. | Promising results for applicability in hydrophobic compounds carrying systems as lycopene with cytotoxic effect on the breast cancer cell. | [11] |
Microencapsulation | Microencapsulation of lycopene from tomato peels by complex coacervation and freeze-drying. | The fine orange-yellow powder could be micro-encapsulated as stable lycopene applied to the food industry with properties against metabolic syndrome. | [3] |
Keywords | INPI (Portugal) | INPI (Brazil) | USPTO (USA) | EPO (European) | WIPO (International) |
---|---|---|---|---|---|
Lycopene | 11 | 58 | 5532 | 29,979 | 30,220 |
Guava | 1 | 45 | 3315 | 14,051 | 18,396 |
Tomato | 34 | 187 | 38,236 | 150,308 | 171,583 |
Psidium guajava | 0 | 14 | 978 | 2007 | 4568 |
Lycopene and tomato | 5 | 7 | 1290 | 8113 | 8390 |
Lycopene and tomato and extract | 0 | 1 | 881 | 5265 | 7313 |
Lycopene and guava | 0 | 2 | 235 | 1496 | 1467 |
Lycopene and guava and extract | 0 | 0 | 207 | 1317 | 1355 |
Lycopene and nano | 0 | 0 | 543 | 2638 | 2689 |
Lycopene and nano-emulsion | 0 | 0 | 111 | 482 | 930 |
Lycopene and nano-emulsion and tomato | 0 | 0 | 23 | 105 | 173 |
Lycopene and nano-emulsion and guava | 0 | 0 | 21 | 31 | 81 |
Antimicrobial and Lycopene | 0 | 0 | 1440 | 4018 | 7289 |
Antimicrobial and Lycopene and extract | 0 | 0 | 1069 | 3054 | 6785 |
Antimicrobial and Lycopene and rich and extract | 0 | 0 | 491 | 1192 | 2615 |
Antimicrobial and Lycopene and rich and extract and tomato | 0 | 0 | 126 | 402 | 1026 |
Antimicrobial and Lycopene and rich and extract and guava | 0 | 0 | 51 | 105 | 181 |
Total | 51 | 314 | 54,549 | 224,563 | 265,061 |
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Amorim, A.d.G.N.; Vasconcelos, A.G.; Souza, J.; Oliveira, A.; Gullón, B.; de Souza de Almeida Leite, J.R.; Pintado, M. Bio-Availability, Anticancer Potential, and Chemical Data of Lycopene: An Overview and Technological Prospecting. Antioxidants 2022, 11, 360. https://doi.org/10.3390/antiox11020360
Amorim AdGN, Vasconcelos AG, Souza J, Oliveira A, Gullón B, de Souza de Almeida Leite JR, Pintado M. Bio-Availability, Anticancer Potential, and Chemical Data of Lycopene: An Overview and Technological Prospecting. Antioxidants. 2022; 11(2):360. https://doi.org/10.3390/antiox11020360
Chicago/Turabian StyleAmorim, Adriany das Graças Nascimento, Andreanne Gomes Vasconcelos, Jessica Souza, Ana Oliveira, Beatriz Gullón, José Roberto de Souza de Almeida Leite, and Manuela Pintado. 2022. "Bio-Availability, Anticancer Potential, and Chemical Data of Lycopene: An Overview and Technological Prospecting" Antioxidants 11, no. 2: 360. https://doi.org/10.3390/antiox11020360