Formation of phytosterol photooxidation products: A chemical reaction mechanism for light-induced oxidation. 2020

Bo-Wen Yang, and Bai-Yi Lu, and Ya-Jing Zhao, and Jin-Yang Luo, and Xin Hong
College of Biosystems Engineering and Food Science, National-Local Joint Engineering Laboratory of Intelligent Food Technology and Equipment, Key Laboratory for Agro-Products Nutritional Evaluation of Ministry of Agriculture and Rural Affairs, Key Laboratory of Agro-Products Postharvest Handling of Ministry of Agriculture and Rural Affairs, Zhejiang Key Laboratory for Agro-Food Processing, Zhejiang International Scientific and Technological Cooperation Base of Health Food Manufacturing and Quality Control, Zhejiang University, Hangzhou 310058, China; Fuli Institute of Food Science, Zhejiang University, Hangzhou 310058, China; Ningbo Research Institute, Zhejiang University, Ningbo 315100, China.

Phytosterols (PS) are a group of sterols distributed in foods and plants, where it is prone to oxidation. In this work, we studied the reaction mechanism of phytosterols, using density functional theory (DFT) calculation and experimental methods to study the photooxidation of phytosterols. Under LED light illumination, experimental photooxidation of these phytosterols gives rise to the prior three kind oxides of phytosterol: 6α-OH, 7α-OH, and 7β-OH. The mechanistic investigations by DFT suggest that singlet oxygen (1O2)-mediated photooxidation (Type II mechanism) generated radical adds to the C5 and C6 on the B Ring of steroid nucleus and reaction in C7 initiated from C5 products through rearrangement pathway. Furthermore, the stereoselectivity at C5, C6 and C7 provides a mechanistic guide for phytosterols photooxidation. These efforts are expected to serve as an essential exploratory study for the oxidation mechanism of phytosterols in the complex food matrix and antioxidation technology for phytosterols.

UI MeSH Term Description Entries
D008027 Light That portion of the electromagnetic spectrum in the visible, ultraviolet, and infrared range. Light, Visible,Photoradiation,Radiation, Visible,Visible Radiation,Photoradiations,Radiations, Visible,Visible Light,Visible Radiations
D010083 Oxidants, Photochemical Compounds that accept electrons in an oxidation-reduction reaction. The reaction is induced by or accelerated by exposure to electromagnetic radiation in the spectrum of visible or ultraviolet light. Photochemical Oxidants
D010084 Oxidation-Reduction A chemical reaction in which an electron is transferred from one molecule to another. The electron-donating molecule is the reducing agent or reductant; the electron-accepting molecule is the oxidizing agent or oxidant. Reducing and oxidizing agents function as conjugate reductant-oxidant pairs or redox pairs (Lehninger, Principles of Biochemistry, 1982, p471). Redox,Oxidation Reduction
D010087 Oxides Binary compounds of oxygen containing the anion O(2-). The anion combines with metals to form alkaline oxides and non-metals to form acidic oxides. Oxide
D010840 Phytosterols A class of organic compounds known as sterols or STEROIDS derived from plants. Plant Sterols,Phytosteroid,Phytosteroids,Phytosterol,Plant Steroid,Plant Steroids,Plant Sterol,Steroid, Plant,Steroids, Plant,Sterol, Plant,Sterols, Plant
D006859 Hydrogen The first chemical element in the periodic table with atomic symbol H, and atomic number 1. Protium (atomic weight 1) is by far the most common hydrogen isotope. Hydrogen also exists as the stable isotope DEUTERIUM (atomic weight 2) and the radioactive isotope TRITIUM (atomic weight 3). Hydrogen forms into a diatomic molecule at room temperature and appears as a highly flammable colorless and odorless gas. Protium,Hydrogen-1
D000077318 Density Functional Theory A theory that is used to describe the electronic ground state properties of matter. It forms the basis of methods in obtaining a solution to the Schrodinger equation for a many-body system, and to investigate the structural, magnetic, and electronic properties of molecules and materials. Density Functional Calculations,Density Functional Computations,Density Functional Theory Calculations,Density Functional Theory Computations,Td-DFT,Td-DFT Calculations,Td-DFT Computations,Time-Dependent Density Functional Theory,Time-Dependent Density Functional Theory Calculations,Time-Dependent Density Functional Theory Computations,DFT Calculations,KS-DFT,Kohn-Sham Density Functional Theory,Calculation, Density Functional,Calculation, Td-DFT,Computation, Density Functional,Computation, Td-DFT,DFT Calculation,Density Functional Calculation,Density Functional Computation,Density Functional Theories,Functional Calculation, Density,Functional Calculations, Density,Functional Computation, Density,Kohn Sham Density Functional Theory,Td DFT Calculations,Td DFT Computations,Td-DFT Calculation,Td-DFT Computation,Time Dependent Density Functional Theory,Time Dependent Density Functional Theory Calculations,Time Dependent Density Functional Theory Computations
D000475 Alkenes Unsaturated hydrocarbons of the type Cn-H2n, indicated by the suffix -ene. (Grant & Hackh's Chemical Dictionary, 5th ed, p408) Alkene,Olefin,Olefins,Pentene,Pentenes
D013256 Steroids A group of polycyclic compounds closely related biochemically to TERPENES. They include cholesterol, numerous hormones, precursors of certain vitamins, bile acids, alcohols (STEROLS), and certain natural drugs and poisons. Steroids have a common nucleus, a fused, reduced 17-carbon atom ring system, cyclopentanoperhydrophenanthrene. Most steroids also have two methyl groups and an aliphatic side-chain attached to the nucleus. (From Hawley's Condensed Chemical Dictionary, 11th ed) Steroid,Catatoxic Steroids,Steroids, Catatoxic
D055668 Photochemical Processes Chemical reactions effected by light. Processes, Photochemical

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