Hussein M. Ali, Salwa A. Eid, Hany A. Sharaf Eldeen, Mai E. H. Ebrahim
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To protect carotenes from oxidation and improve their use as food additives and pharmaceuticals, carrot carotenoids were encapsulated in a chitosan-TPP copolymer.</p><h3>Results</h3><p>The results revealed that the main carotene oxidation product from H<sub>2</sub>O<sub>2</sub> and HOCl was apo-13-carotenone-5,6-epoxide; LC–MS/MS also detected additional products for the first time. The kinetics study indicated that oxidation follows first-order kinetics in carotene and second-order kinetics in H2O2, with epoxidation of the ring double bonds and cleavage of the 13-double bond forming the major product, while cleavage of the single bond C10’–C11 resulted in the minor product, β-apo-12ʹ-carotenone-5,6-epoxide; proposed mechanisms were outlined. To protect carotenoids from oxidation, a chitosan-TPP complex was prepared and characterized. While free carotene stability decreased to 63% after 120 min and 34% after 30 min under H<sub>2</sub>O<sub>2</sub> and HOCl treatments, respectively, the complex remained stable at over 94% for 300 min. Additionally, the complex did not reduce the antioxidant activity of carotene against hydroxyl radicals but slightly lowered its reducing power. Carotene release followed first-order kinetics with an 88.33% recovery over nine days, mainly controlled by diffusion.</p><h3>Conclusion</h3><p>Producing apo-13-carotenone-5,6-epoxide as a major product in carotene oxidation by both oxidants suggests that it may serve as a potential biomarker. Other new products were identified that require further study to examine their activities. The prepared chitosan-TPP complex effectively stabilizes carotenes against both ROS while retaining most of their original antioxidant activities, indicating its potential applications in the pharmaceutical and food industries.</p><h3>Graphical Abstract</h3>\n<div><figure><div><div><picture><source><img></source></picture></div></div></figure></div></div>","PeriodicalId":512,"journal":{"name":"Chemical and Biological Technologies in Agriculture","volume":"12 1","pages":""},"PeriodicalIF":5.2000,"publicationDate":"2025-09-15","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"https://chembioagro.springeropen.com/counter/pdf/10.1186/s40538-025-00855-2","citationCount":"0","resultStr":"{\"title\":\"Oxidative degradation pathways of carrot carotenes and their protection via chitosan-TPP encapsulation\",\"authors\":\"Hussein M. Ali, Salwa A. Eid, Hany A. Sharaf Eldeen, Mai E. H. 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The kinetics study indicated that oxidation follows first-order kinetics in carotene and second-order kinetics in H2O2, with epoxidation of the ring double bonds and cleavage of the 13-double bond forming the major product, while cleavage of the single bond C10’–C11 resulted in the minor product, β-apo-12ʹ-carotenone-5,6-epoxide; proposed mechanisms were outlined. To protect carotenoids from oxidation, a chitosan-TPP complex was prepared and characterized. While free carotene stability decreased to 63% after 120 min and 34% after 30 min under H<sub>2</sub>O<sub>2</sub> and HOCl treatments, respectively, the complex remained stable at over 94% for 300 min. Additionally, the complex did not reduce the antioxidant activity of carotene against hydroxyl radicals but slightly lowered its reducing power. 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Oxidative degradation pathways of carrot carotenes and their protection via chitosan-TPP encapsulation
Background
Hydrogen peroxide and hypochlorous acid are reactive oxygen species that naturally occur in biological systems; the oxidation products of biological molecules, such as carotenoids, formed by these oxidants are found in foods and living organisms. This study aims to identify these metabolite products and propose the degradation mechanism based on the identified product structures and the obtained kinetic data. To protect carotenes from oxidation and improve their use as food additives and pharmaceuticals, carrot carotenoids were encapsulated in a chitosan-TPP copolymer.
Results
The results revealed that the main carotene oxidation product from H2O2 and HOCl was apo-13-carotenone-5,6-epoxide; LC–MS/MS also detected additional products for the first time. The kinetics study indicated that oxidation follows first-order kinetics in carotene and second-order kinetics in H2O2, with epoxidation of the ring double bonds and cleavage of the 13-double bond forming the major product, while cleavage of the single bond C10’–C11 resulted in the minor product, β-apo-12ʹ-carotenone-5,6-epoxide; proposed mechanisms were outlined. To protect carotenoids from oxidation, a chitosan-TPP complex was prepared and characterized. While free carotene stability decreased to 63% after 120 min and 34% after 30 min under H2O2 and HOCl treatments, respectively, the complex remained stable at over 94% for 300 min. Additionally, the complex did not reduce the antioxidant activity of carotene against hydroxyl radicals but slightly lowered its reducing power. Carotene release followed first-order kinetics with an 88.33% recovery over nine days, mainly controlled by diffusion.
Conclusion
Producing apo-13-carotenone-5,6-epoxide as a major product in carotene oxidation by both oxidants suggests that it may serve as a potential biomarker. Other new products were identified that require further study to examine their activities. The prepared chitosan-TPP complex effectively stabilizes carotenes against both ROS while retaining most of their original antioxidant activities, indicating its potential applications in the pharmaceutical and food industries.
期刊介绍：
Chemical and Biological Technologies in Agriculture is an international, interdisciplinary, peer-reviewed forum for the advancement and application to all fields of agriculture of modern chemical, biochemical and molecular technologies. The scope of this journal includes chemical and biochemical processes aimed to increase sustainable agricultural and food production, the evaluation of quality and origin of raw primary products and their transformation into foods and chemicals, as well as environmental monitoring and remediation. Of special interest are the effects of chemical and biochemical technologies, also at the nano and supramolecular scale, on the relationships between soil, plants, microorganisms and their environment, with the help of modern bioinformatics. Another special focus is the use of modern bioorganic and biological chemistry to develop new technologies for plant nutrition and bio-stimulation, advancement of biorefineries from biomasses, safe and traceable food products, carbon storage in soil and plants and restoration of contaminated soils to agriculture.
This journal presents the first opportunity to bring together researchers from a wide number of disciplines within the agricultural chemical and biological sciences, from both industry and academia. The principle aim of Chemical and Biological Technologies in Agriculture is to allow the exchange of the most advanced chemical and biochemical knowledge to develop technologies which address one of the most pressing challenges of our times - sustaining a growing world population.
Chemical and Biological Technologies in Agriculture publishes original research articles, short letters and invited reviews. Articles from scientists in industry, academia as well as private research institutes, non-governmental and environmental organizations are encouraged.
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