Antioxidant Activity of Planar Catechin Conjugated with Trolox

Shimizu, Wakana; Shoji, Yoshimi; Ohkubo, Kei; Ito, Hiromu; Nakanishi, Ikuo; Fukuhara, Kiyoshi

doi:10.3390/antiox13101165

Open AccessArticle

Antioxidant Activity of Planar Catechin Conjugated with Trolox

by

Wakana Shimizu

^1,2,†,

Yoshimi Shoji

^2,†,

Kei Ohkubo

^2,3

,

Hiromu Ito

²,

Ikuo Nakanishi

^2,*

and

Kiyoshi Fukuhara

^1,2,*

¹

Division of Organic and Medicinal Chemistry, Showa University School of Pharmacy, Shinagawa-ku, Tokyo 142-8555, Japan

²

Quantum RedOx Chemistry Team, Quantum Life Spin Group, Institute for Quantum Life Science (iQLS), National Institutes for Quantum Science and Technology (QST), Chiba-shi, Chiba 263-8555, Japan

³

Institute for Open and Transdisciplinary Research Initiatives (OTRI), Osaka University, Suita, Osaka 565-0871, Japan

^*

Authors to whom correspondence should be addressed.

^†

These authors contributed equally to this work.

Antioxidants 2024, 13(10), 1165; https://doi.org/10.3390/antiox13101165

Submission received: 21 August 2024 / Revised: 18 September 2024 / Accepted: 23 September 2024 / Published: 25 September 2024

(This article belongs to the Special Issue Bioactive Compounds: Antioxidant, Antibacterial, Anti-inflammatory Modulation)

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Abstract

Planar catechin (PCat), a natural antioxidant with a fixed 3D catechin structure on a plane, exhibits radical-scavenging activity approximately five times stronger than the conventional catechin. We synthesized a compound, PCat-TrOH, by binding Trolox (TrOH), an α-tocopherol analog, to PCat to enhance its antioxidant effect against oxidative stress, such as lipid peroxidation. TrOH shows radical-scavenging activity about 6.5 times greater than PCat, and PCat-TrOH exhibited a similar level of radical-scavenging activity to TrOH. Additionally, PCat-TrOH demonstrated twice the radical-scavenging activity against reactive oxygen species compared to PCat or TrOH. This compound is also expected to exhibit an excellent antioxidant effect against lipid peroxidation caused by radical chain reactions, through interactions with vitamin C, similar to that in the case of α-tocopherol.

Keywords: catechin; trolox; tocopherol; antioxidant activity

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MDPI and ACS Style

Shimizu, W.; Shoji, Y.; Ohkubo, K.; Ito, H.; Nakanishi, I.; Fukuhara, K. Antioxidant Activity of Planar Catechin Conjugated with Trolox. Antioxidants 2024, 13, 1165. https://doi.org/10.3390/antiox13101165

AMA Style

Shimizu W, Shoji Y, Ohkubo K, Ito H, Nakanishi I, Fukuhara K. Antioxidant Activity of Planar Catechin Conjugated with Trolox. Antioxidants. 2024; 13(10):1165. https://doi.org/10.3390/antiox13101165

Chicago/Turabian Style

Shimizu, Wakana, Yoshimi Shoji, Kei Ohkubo, Hiromu Ito, Ikuo Nakanishi, and Kiyoshi Fukuhara. 2024. "Antioxidant Activity of Planar Catechin Conjugated with Trolox" Antioxidants 13, no. 10: 1165. https://doi.org/10.3390/antiox13101165

APA Style

Shimizu, W., Shoji, Y., Ohkubo, K., Ito, H., Nakanishi, I., & Fukuhara, K. (2024). Antioxidant Activity of Planar Catechin Conjugated with Trolox. Antioxidants, 13(10), 1165. https://doi.org/10.3390/antiox13101165

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Antioxidant Activity of Planar Catechin Conjugated with Trolox

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