Catalytic Antioxidant Activity of Two Diterpenoid Polyphenols of Rosemary, Carnosol and Isorosmanol, against Lipid Oxidation in the Presence of Cysteine Thiol

07 November 2023, Version 1
This content is a preprint and has not undergone peer review at the time of posting.

Abstract

Lamiaceae herbs such as rosemary have excellent antioxidant properties, and lipidic diterpenoid constituents, such as carnosol, are known as characteristic components to exhibit strong antioxidant activity. This study investigates the effect of thiol compounds on the antioxidant properties of diterpenoid polyphenols. The results concerning the antioxidant activity of polyphenols in the presence of thiol showed that two polyphenols, namely carnosol and isorosmanol, enhanced antioxidant capacity against the radical-induced oxidation of lipids. Further examination of the mechanism revealed that both polyphenols exhibit excellent catalytic antioxidant activity by using the thiol group as a reduction source. Using density functional theory calculations, we attempted to explain why only these two polyphenols exhibit catalytic antioxidant properties. The calculation results and the assumed reaction mechanism suggested that the orthoquinones produced in the antioxidant reactions of carnosol and isorosmanol are more unstable than the others, and that the regioselectivity of their reactions with thiols contributes to their catalytic antioxidant properties.

Keywords

Catalytic Antioxidant
Rosemary
Cysteine Thiol
Carnosol

Supplementary materials

Title
Description
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Title
Data for strucure identification and 3D structures for DFT calculation
Description
1. Analytical Data for Identification of isoROS, ROS, and epiROS. 2. Analytical Data for Structure Determination of Compounds 1 and 2. 3. Figure S1. Drawing of the Optimized Stereostrucures of Rosemary Polyphenols, Their Quinone Derivatives, BCysM, and (BCysM)2.
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