Apocarotenals of Phenolic Carotenoids for Superior Antioxidant Activities

Gaosheng Shi; Lina Gu; Hyunuk Jung; Wook-Jin Chung; Sangho Koo

doi:10.1021/acsomega.1c04432

Apocarotenals of Phenolic Carotenoids for Superior Antioxidant Activities

ACS Omega. 2021 Sep 16;6(38):25096-25108. doi: 10.1021/acsomega.1c04432. eCollection 2021 Sep 28.

Authors

Gaosheng Shi¹, Lina Gu^{1

2}, Hyunuk Jung¹, Wook-Jin Chung¹, Sangho Koo^{1

2

3}

Affiliations

¹ Department of Energy Science and Technology, Myongji University, Myongji-Ro 116, Cheoin-Gu, Yongin, Gyeonggi-Do 17058, Korea.
² School of Pharmacy, East China University of Science and Technology, Meilong Road 130, Shanghai 200237, P. R. China.
³ Department of Chemistry, Myongji University, Myongji-Ro 116, Cheoin-Gu, Yongin, Gyeonggi-Do 17058, Korea.

Abstract

A series of para-phenolic carotenes 1 with ortho- and meta-substitutions were respectively prepared utilizing the benzenesulfonyl protection method, which demonstrated the importance of the ring substituents on their effective conjugation, evaluated by their UV absorption values. The corresponding apo-12'-carotenals 2 were devised to improve the conjugation effect of the para-phenolic radical with the polyene chain by the conjugated aldehyde group. Apo-12'-carotenals 2b and 2c without ortho-substituents exhibited superior antioxidant activities to their corresponding symmetrical carotenes 1 as well as β-carotene and apo-12'-β-carotenal in 2,2'-azino-bis(3-ethylbenzothiazoline-6-sulfonic acid) (ABTS) and 1,1-diphenyl-2-picryl-hydrazyl (DPPH) radical scavenging assays.