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

Apocarotenals of Phenolic Carotenoids for Superior Antioxidant Activities

Gaosheng Shi  1 , Lina Gu  1   2 , Hyunuk Jung  1 , Wook-Jin Chung  1 , Sangho Koo  1   2   3
Affiliations

Apocarotenals of Phenolic Carotenoids for Superior Antioxidant Activities

Gaosheng Shi et al. ACS Omega. .

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.

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Conflict of interest statement

The authors declare no competing financial interest.

Figures

Figure 1
Figure 1
Proposed carotenes 1 and apo-12′-carotenals 2 with phenol end group(s) for superior antioxidant activities.
Scheme 1
Scheme 1. Preparation of Protected 4-Hydroxybenzaldehydes 4 for the Phenol-Ending Carotenoids
Scheme 2
Scheme 2. Synthetic Routes for the Phenol-Ending Carotenes 1 and Apo-12′-carotenals 2
Figure 2
Figure 2
Carotenes 1 and apo-12′-carotenals 2 with para-phenol end group(s) and their UV absorption values (λmax) in DMSO.
See this image and copyright information in PMC

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