Comparative Evaluation of the Radical-Scavenging Activities of Fucoxanthin and Its Stereoisomers

Abstract

Fucoxanthin (Fuco) is a characteristic carotenoid of brown seaweeds. In the present study, Fuco and its stereoisomers 9'Z-Fuco, 13Z-and 13'Z-Fuco were extracted from Laminaria japonica Aresch. They were isolated and purified by silica gel column chromatography, Sephadex LH-20, and reversed-phase HPLC. The radical-scavenging activities of the three stereoisomers were evaluated toward 1,1-diphenyl-2-picrylhydrazyl (DPPH) radical, 2-2'-azinobis-(3-ethylbenzothiazoline-6-sulfonic acid) (ABTS) radical, hydroxyl radical, and superoxide radical. The order of 1,1-diphenyl-2-picrylhydrazyl (DPPH) radical-scavenging activity was 13Z-and 13'Z-Fuco > (all-E)-Fuco > 9'Z-Fuco. The order of 2-2'-azinobis-(3-ethylbenzothiazoline-6-sulfonic acid) (ABTS) and hydroxyl radical-scavenging activities were 9'Z-Fuco > (all-E)-Fuco > 13Z-and 13'Z-Fuco. The order of superoxide radical-scavenging activity was 13Z-and 13'Z-Fuco > (all-E)-Fuco > 9'Z-Fuco. The scavenging activities of Fuco and its stereoisomers toward the four radical types were all dose-dependent. The ABTS, DPPH, and superoxide radical-scavenging activities were all weaker than that of tocopherol (VE), while their hydroxyl radical-scavenging activities were stronger than that of VE. The results confirmed that Fuco and its stereoisomers have potent antioxidant activities.

Effects of Antioxidant, Anti-Collagenase, Anti-Elastase, Anti-Tyrosinase of The Extract and Fraction From Turbinaria decurrens Bory.

“…The major bioactive compound that responsible for antioxidant activity in macroalgae was identified as the carotenoid fucoxanthin (Kelman et al, 2012). Another study also reported that fucoxanthin and its stereoisomers from Laminaria japonica Aresch had stronger scavenging hydroxyl radical activities than αtocopherol, while the radical-scavenging activities of the fucoxanthin stereoisomers were not significantly different (Zhang et al, 2014). The study indicated that ETD and FTD have potent antioxidant activities in vitro which in line with the previous studies and fucoxanthin was thought to be responsible for the activity.…”

Isolation of Fucoxanthin from Brown Algae and Its Antioxidant Activity: In Vitro and 5% Fish Oil‐In‐Water Emulsion

“…Our results are in agreement with earlier studies on the radical-scavenging activity of fucoxanthin isolated from Hyaleucerea fusisformis (Yan, Chuda, Suzuki, & Nagata, 1999) and marine Diatom Odontella aurita (Xia et al, 2013). Similarly, the studies conducted by Zhang et al (2014) also found a concentration dependency of radical-scavenging activity of fucoxanthin and its isomers. Fucoxanthin was reported to have higher DPPH radical scavenging than other carotenoids such as β-carotene, β-cryptoxanthin, zeaxanthin, and lutein under anoxic conditions than under aerobic conditions; however, it always had a lower activity than α-tocopherol (Nomura, Kikuchi, Kubodera, & Kawakami, 1997).…”

Marine natural products

“…Confocal laser microscopy determined that the labeled dieckol was mainly located in the endoplasmic reticulum and studies showed that the anti-inammatory activity of the conjugate was considerably greater than that of dieckol itself. 471 The potential therapeutic properties of fucoxanthin and derivatives have been studied, 472,473 as have those of polyphenols such as octaphlorethol, [474][475][476] and mono-and diacylglycerols. 477 6 Red algae There continues to be a marked variation in the number of new compounds obtained from red algae and reported each year, with 42 for 2014 compared to 9 for 2013.…”