Antioxidant Activity of Planar Catechin Conjugated with Trolox
Wakana Shimizu,
Yoshimi Shoji,
Kei Ohkubo,
Hiromu Ito,
Ikuo Nakanishi,
Kiyoshi Fukuhara
Affiliations
Wakana Shimizu
Division of Organic and Medicinal Chemistry, Showa University School of Pharmacy, Shinagawa-ku, Tokyo 142-8555, Japan
Yoshimi Shoji
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
Kei Ohkubo
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
Hiromu Ito
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
Ikuo Nakanishi
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
Kiyoshi Fukuhara
Division of Organic and Medicinal Chemistry, Showa University School of Pharmacy, Shinagawa-ku, Tokyo 142-8555, Japan
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.
