ISSN print edition: 0366-6352 ISSN electronic edition: 1336-9075 Registr. No.: MK SR 9/7 Published monthly

Theoretical and kinetic study of the singlet oxygen quenching reaction by hesperidin isolated from mandarin (Citrus reticulata) fruit peels

Carlos Diaz-Uribe, William Vallejo, Teylis De la Hoz, Jiress Florez, Amner Muñoz-Acevedo, Ximena Zarate, and Eduardo Schott

Grupo de Investigación en Fotoquímica Y Fotobiología, Programa de Química, Facultad de Ciencias Básicas,, Universidad del Atlántico, Puerto Colombia, Atlántico, Colombia

E-mail: williamvallejo@mail.uniatlantico.edu.co

Received: 12 June 2021  Accepted: 16 August 2021

Abstract:

Antioxidants act as quenchers or scavengers of oxidative free radicals and singlet oxygen (¹O₂); these compounds are effective in the treatment of diseases associated with oxidative stress and food preservation. We studied the antioxidant activity of hesperidin which was isolated from mandarin (Citrus reticulata) fruit peels against singlet oxygen (¹O₂). High-performance liquid chromatography with diode array detection was used for chemical characterization. The total singlet oxygen quenching rate constants of the hesperidin was measured by using the Stern–Volmer model. Results showed an overall quenching rate constant with a value of 6.43 × 10⁷ M⁻¹ s⁻¹ for ¹O₂, which for the best of our knowledge has not been reported before. Furthermore, quantum chemical calculations were performed to get insight into the molecular and electronic structure properties of this antioxidant, which confirms that the quenching mechanism through energy transfer is rarely probable and that ¹O₂ could interact with the methoxy phenyl charge rich fragment of the molecule.

Keywords: Singlet oxygen; Antioxidant; Hesperidin; Stern–Volmer model; Citrus reticulata

Full paper is available at www.springerlink.com.

DOI: 10.1007/s11696-021-01825-2

Chemical Papers 76 (1) 169–178 (2022)