Highly efficient trans–cis isomerization of lycopene catalyzed by iodine-doped TiO<sub>2</sub>nanoparticles

Sun, Qingjie; Yang, Cheng; Li, Jing; Aboshora, Waleed; Raza, Husnain; Zhang, Lianfu

doi:10.1039/c5ra24074c

Cited by 19 publications

(25 citation statements)

References 34 publications

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“…From an industrial perspective lycopene isomerization with the I‐TiO 2 catalyst in refluxing ethyl acetate could be a convenient procedure. The prominent advantage is that ethyl acetate is already approved for use in the manufacture of lycopene products from tomato extracts and therefore extraction and catalytic configuration transformation can be achieved in a continuous production manner (Sun and others ). Besides, most of the I‐TiO 2 solid catalyst after reaction can be removed by centrifugation or filtration, which will contribute to the safety of the isomerized lycopene product applied in foods, dietary supplements, and medical fields.…”

Section: Resultsmentioning

confidence: 99%

“…At given time intervals, the reaction suspension was sampled and centrifuged (12000 rpm, 10 min) to remove the I‐TiO 2 catalyst particles. The lycopene isomers profile was analyzed according to the method of our previous study (Sun and others ). Briefly, the analysis was performed at a column temperature of 30 °C by HPLC (Agilent 1200; Agilent Technologies Inc., Waldbronn, Germany), equipped with an analytical reversed‐phase C30‐column (YMC Carotenoid S, 5 μm, 250 × 4.6 mm; YMC Co., Ltd., Shanghai, China) and diode array detector.…”

Section: Methodsmentioning

confidence: 99%

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Lycopene: Heterogeneous Catalytic E/Z Isomerization and In Vitro Bioaccessibility Assessment Using a Diffusion Model

Sun

Yang

et al. 2016

Journal of Food Science

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Highly efficient heterogeneous catalytic E/Z isomerization of lycopene was achieved using an iodine-doped titanium dioxide (I-TiO ) catalyst prepared by sol-gel method. The effects of reaction temperature and reaction time were investigated in detail. The maximum total Z-ratio of lycopene exceeded 78% after 2 h of refluxing at 75 °C in ethyl acetate. Moreover, lycopene samples with a series of total Z-ratios were prepared and the bioaccessibility of these samples was estimated using a diffusion model, the results showed that the bioaccessibility of lycopene markedly increased conforming to a linear regression model with increasing of the total Z-ratio of lycopene from 3.6% to 78.5%. Furthermore, the specific role of the microstructure and melting point of 3.6% and 78.5% total Z-ratio of lycopene was also investigated to understand the probable mechanism for the enhanced bioaccessbility of (Z)-lycopenes.

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Section: Resultsmentioning

confidence: 99%

Section: Methodsmentioning

confidence: 99%

Lycopene: Heterogeneous Catalytic E/Z Isomerization and In Vitro Bioaccessibility Assessment Using a Diffusion Model

Sun

Yang

et al. 2016

Journal of Food Science

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“…Employing photoisomerization with suppressed degradation of lycopene, Honda et al achieved the highest isomerization efficiency of 80.4% using the sensitizer erythrosine in hexane under 480–600 nm light irradiation. Similarly, a high (60.5%) conversion of all- E -lycopene to 5-Z-, 9-Z-, and 13-Z-lycopene was achieved using an iodine-doped titanium dioxide (I-TiO2) catalyst reaction for 2 h in ethyl acetate at 75 °C …”

Section: Processing and Storage Of Lycopene-containing Foodsmentioning

confidence: 99%

“…Similarly, a high (60.5%) conversion of all-E-lycopene to 5-Z-, 9-Z-, and 13-Z-lycopene was achieved using an iodine-doped titanium dioxide (I-TiO2) catalyst reaction for 2 h in ethyl acetate at 75 °C. 49 Interestingly, photoinduced isomerization of lycopene can be utilized to authenticate field-grown and greenhouse-grown tomatoes. Both 5-Z-and 7-Z-lycopene isomers were found to be expressed differently under photoinduced isomerization.…”

Section: Lycopene-containing Foodsmentioning

confidence: 99%

Chemical Stability of Lycopene in Processed Products: A Review of the Effects of Processing Methods and Modern Preservation Strategies

Saini

Bekhit

Roohinejad

et al. 2019

J. Agric. Food Chem.

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Lycopene, one of the most dominant carotenoids in a person’s diet, is a well-known natural compound that has protective effects against chronic diseases. Industrial and domestic processing and storage conditions significantly influence retention and isomerization of lycopene; thus, in recent years, great attention has been given for their preservative effects of lycopene. This review highlights recent strategies that have been developed to preserve lycopene in processed products, especially in tomato pulp, puree, paste, and juice. The key factors influencing lycopene degradation and isomerization, such as ingredients and intensity of thermal treatments, are also discussed. Special attention was paid to the crystalline structures of lycopene which facilitate its resistance to degradation and isomerization. Emerging non-thermal processing methods, such as ultrasound and high-pressure processing (HPP), are critically evaluated for their preservation of thermo-labile compounds. Novel trends to improve lycopene stability by micro- and nanoencapsulation and addition of antioxidants are also included to examine their efficacy to protect against light, heat, oxygen, and other oxidative processes. Finally, recommended processing and storage conditions are discussed to provide strategies to retain the highest possible amount of bioactive lycopene until consumption.

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“…On heating at 250 °C, the total Z ‐isomer content reached ≈80% within a short time (5 min) in both the heating methods. Several studies also obtained ≈80% Z ‐isomer in lycopene; however, these studies used toxic organic solvents and catalysts and required considerable time to obtain such high amount of the Z ‐isomers . When tomato powder was heated above 240 °C, lycopene in tomato powder was decomposed in both the heating methods (Figure 3b).…”

Section: Resultsmentioning

confidence: 99%

Chemical‐Free Approach for Z‐Isomerization of Lycopene in Tomato Powder: Hot Air and Superheated Steam Heating above the Melting Point of Lycopene

Honda

Kageyama

Hibino

et al. 2019

Euro J Lipid Sci & Tech

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Z‐isomers of lycopene exhibit higher bioavailability and antioxidant capacity than those of the all‐E‐isomer. Therefore, it is important to develop an efficient and environmentally friendly procedure for Z‐isomerization. The current methods for Z‐isomerization of (all‐E)‐lycopene use toxic chemicals such as organic solvents and catalysts. This study is aimed to develop a chemical‐free method for Z‐isomerization of (all‐E)‐lycopene in tomato powder by hot air and superheated steam heating. The Z‐isomerization reaction is promoted by heating above the melting point of lycopene. When heated with superheated steam, the thermal decomposition of lycopene is suppressed compared to that when heated with hot air. When tomato powder is heated at 240 °C for 5 min by superheated steam, the total Z‐isomer content and remaining lycopene are 69.0% and 90.7%, respectively, while with hot air heating, the total Z‐isomer content and remaining lycopene are 69.9% and 68.0%, respectively. These results indicate that the thermal Z‐isomerization of lycopene occurs in the molten state and heating in a low oxygen atmosphere suppresses the thermal decomposition of lycopene. Practical Applications: Tomato powder rich in lycopene Z‐isomers is an important ingredient for the food and animal feed industries. Since Z‐isomers of lycopene are more soluble in solvents including ethanol which is a low‐toxicity and environmentally friendly solvent, the efficiency of lycopene extraction with ethanol can be improved by using the Z‐isomer‐rich tomato powder as a raw material. The obtained Z‐isomer‐rich extract has a high added value because the Z‐isomers have higher bioavailability and antioxidant capacity than those of the all‐E‐isomer. In addition, since lycopene Z‐isomers exhibit higher accumulation efficiency and better color improvement in hen egg yolks than those of the all‐E‐isomer, Z‐isomer‐rich tomato powder is an effective animal feed.

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Highly efficient trans–cis isomerization of lycopene catalyzed by iodine-doped TiO₂nanoparticles

Abstract: Highly efficienttrans–cisisomerization of lycopene was achieved in the presence of a novel iodine-doped titanium dioxide (I-TiO2) catalyst.

Cited by 19 publications

References 34 publications

Lycopene: Heterogeneous Catalytic E/Z Isomerization and In Vitro Bioaccessibility Assessment Using a Diffusion Model

Lycopene: Heterogeneous Catalytic E/Z Isomerization and In Vitro Bioaccessibility Assessment Using a Diffusion Model

Chemical Stability of Lycopene in Processed Products: A Review of the Effects of Processing Methods and Modern Preservation Strategies

Chemical‐Free Approach for Z‐Isomerization of Lycopene in Tomato Powder: Hot Air and Superheated Steam Heating above the Melting Point of Lycopene

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Highly efficient trans–cis isomerization of lycopene catalyzed by iodine-doped TiO2nanoparticles

Abstract: Highly efficienttrans–cisisomerization of lycopene was achieved in the presence of a novel iodine-doped titanium dioxide (I-TiO2) catalyst.

Cited by 19 publications

References 34 publications

Lycopene: Heterogeneous Catalytic E/Z Isomerization and In Vitro Bioaccessibility Assessment Using a Diffusion Model

Lycopene: Heterogeneous Catalytic E/Z Isomerization and In Vitro Bioaccessibility Assessment Using a Diffusion Model

Chemical Stability of Lycopene in Processed Products: A Review of the Effects of Processing Methods and Modern Preservation Strategies

Chemical‐Free Approach for Z‐Isomerization of Lycopene in Tomato Powder: Hot Air and Superheated Steam Heating above the Melting Point of Lycopene

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Highly efficient trans–cis isomerization of lycopene catalyzed by iodine-doped TiO₂nanoparticles