Shi Gaosheng, Gu Lina, Jung Hyunuk, Chung Wook-Jin, Koo Sangho
Department of Energy Science and Technology, Myongji University, Myongji-Ro 116, Cheoin-Gu, Yongin, Gyeonggi-Do 17058, Korea.
School of Pharmacy, East China University of Science and Technology, Meilong Road 130, Shanghai 200237, P. R. China.
ACS Omega. 2021 Sep 16;6(38):25096-25108. doi: 10.1021/acsomega.1c04432. eCollection 2021 Sep 28.
A series of -phenolic carotenes 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 were devised to improve the conjugation effect of the -phenolic radical with the polyene chain by the conjugated aldehyde group. Apo-12'-carotenals and without -substituents exhibited superior antioxidant activities to their corresponding symmetrical carotenes 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.
利用苯磺酰保护法分别制备了一系列具有邻位和间位取代基的-酚类胡萝卜素，通过其紫外吸收值评估表明环取代基对其有效共轭的重要性。设计相应的脱辅基-12'-视黄醛以通过共轭醛基提高-酚基与多烯链的共轭效果。在2,2'-偶氮二（3-乙基苯并噻唑啉-6-磺酸）（ABTS）和1,1-二苯基-2-苦基肼（DPPH）自由基清除试验中，无-取代基的脱辅基-12'-视黄醛及其相应的对称类胡萝卜素表现出比β-胡萝卜素和脱辅基-12'-β-视黄醛更强的抗氧化活性。
