Chemical Transformation of Astaxanthin from Improves Its Antioxidative and Anti-inflammatory Activities

Overview

Journal ACS Omega

Publisher American Chemical Society

Specialty Chemistry

Date 2020 Aug 11

PMID 32775914

Citations 7

Authors

Sung Hyun Hwang

Ji Min Kim

Seokjoon Kim

Min Jin Yoon

Ki Soo Park

Affiliations

Soon will be listed here.

Abstract

Astaxanthin is a strong antioxidant, but the effect of esterification on its biological activities remains unclear. Here, we chemically synthesized three forms of astaxanthin (nonesterified (Ast-N), monoesterified (Ast-mE), and diesterified (Ast-dE) forms) using esterified astaxanthin (Ast-E) in natural extract from and characterized them by spectrophotometry and high-performance liquid chromatography (HPLC). Additionally, the antioxidant and anti-inflammatory activities of the samples containing three forms of astaxanthin at different ratios were evaluated. The sample containing the maximum level of Ast-mE compared to those of Ast-N and Ast-dE showed the highest antioxidant and anti-inflammatory activities. We also observed the greatest increase in expression of genes related to antioxidant and anti-inflammatory effects in samples containing the highest Ast-mE. These results provide a foundation for in-depth investigation of astaxanthin and other antioxidant molecules, allowing for the development of a practical and cost-effective strategy to improve antioxidant or anti-inflammatory activities of natural extracts that can be used as dietary supplements.

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References

Lockwood S, Gross G . Disodium disuccinate astaxanthin (Cardax): antioxidant and antiinflammatory cardioprotection. Cardiovasc Drug Rev. 2005; 23(3):199-216. DOI: 10.1111/j.1527-3466.2005.tb00166.x. View

Naguib Y . Antioxidant activities of astaxanthin and related carotenoids. J Agric Food Chem. 2000; 48(4):1150-4. DOI: 10.1021/jf991106k. View

Gorrini C, Harris I, Mak T . Modulation of oxidative stress as an anticancer strategy. Nat Rev Drug Discov. 2013; 12(12):931-47. DOI: 10.1038/nrd4002. View

Cho B, Ryu H, So Y, Lee C, Jin C, Yook H . Anti-Inflammatory Effect of Mangostenone F in Lipopolysaccharide-Stimulated RAW264.7 Macrophages by Suppressing NF-κB and MAPK Activation. Biomol Ther (Seoul). 2014; 22(4):288-94. PMC: 4131528. DOI: 10.4062/biomolther.2014.052. View

Yoon S, Lee Y, Park S, Kim H, Bae H, Kim H . Anti-inflammatory effects of Scutellaria baicalensis water extract on LPS-activated RAW 264.7 macrophages. J Ethnopharmacol. 2009; 125(2):286-90. DOI: 10.1016/j.jep.2009.06.027. View

Liu X, Osawa T . Cis astaxanthin and especially 9-cis astaxanthin exhibits a higher antioxidant activity in vitro compared to the all-trans isomer. Biochem Biophys Res Commun. 2007; 357(1):187-93. DOI: 10.1016/j.bbrc.2007.03.120. View

Dose J, Matsugo S, Yokokawa H, Koshida Y, Okazaki S, Seidel U . Free Radical Scavenging and Cellular Antioxidant Properties of Astaxanthin. Int J Mol Sci. 2016; 17(1). PMC: 4730345. DOI: 10.3390/ijms17010103. View

Taciak B, Bialasek M, Braniewska A, Sas Z, Sawicka P, Kiraga L . Evaluation of phenotypic and functional stability of RAW 264.7 cell line through serial passages. PLoS One. 2018; 13(6):e0198943. PMC: 5995401. DOI: 10.1371/journal.pone.0198943. View

Nishigaki I, Rajendran P, Venugopal R, Ekambaram G, Sakthisekaran D, Nishigaki Y . Cytoprotective role of astaxanthin against glycated protein/iron chelate-induced toxicity in human umbilical vein endothelial cells. Phytother Res. 2009; 24(1):54-9. DOI: 10.1002/ptr.2867. View

10.

Kim C, Ji J, Baek S, Lee J, Ha I, Lim S . Fermented dried peel extracts exert anti-inflammatory activities in LPS-induced RAW264.7 macrophages and improve skin moisturizing efficacy in immortalized human HaCaT keratinocytes. Pharm Biol. 2019; 57(1):392-402. PMC: 6566750. DOI: 10.1080/13880209.2019.1621353. View

11.

de Torre M, Cavero R, Calvo M, Vizmanos J . A Simple and a Reliable Method to Quantify Antioxidant Activity In Vivo. Antioxidants (Basel). 2019; 8(5). PMC: 6562907. DOI: 10.3390/antiox8050142. View

12.

Galasso C, Orefice I, Pellone P, Cirino P, Miele R, Ianora A . On the Neuroprotective Role of Astaxanthin: New Perspectives?. Mar Drugs. 2018; 16(8). PMC: 6117702. DOI: 10.3390/md16080247. View

13.

Ceron M, Garcia-Malea M, Rivas J, Acien F, Fernandez J, Del Rio E . Antioxidant activity of Haematococcus pluvialis cells grown in continuous culture as a function of their carotenoid and fatty acid content. Appl Microbiol Biotechnol. 2006; 74(5):1112-9. DOI: 10.1007/s00253-006-0743-5. View

14.

Yang Y, Kim B, Park Y, Koo S, Lee J . Astaxanthin prevents TGFβ1-induced pro-fibrogenic gene expression by inhibiting Smad3 activation in hepatic stellate cells. Biochim Biophys Acta. 2014; 1850(1):178-85. DOI: 10.1016/j.bbagen.2014.10.014. View

15.

Hahn H, Kim K, An I, Ahn K, Han H . Protective effects of rosmarinic acid against hydrogen peroxide‑induced cellular senescence and the inflammatory response in normal human dermal fibroblasts. Mol Med Rep. 2017; 16(6):9763-9769. DOI: 10.3892/mmr.2017.7804. View

16.

Fassett R, Coombes J . Astaxanthin: a potential therapeutic agent in cardiovascular disease. Mar Drugs. 2011; 9(3):447-65. PMC: 3083660. DOI: 10.3390/md9030447. View

17.

Hseu Y, Chen X, Gowrisankar Y, Yen H, Chuang J, Yang H . The Skin-Whitening Effects of Ectoine via the Suppression of α-MSH-Stimulated Melanogenesis and the Activation of Antioxidant Nrf2 Pathways in UVA-Irradiated Keratinocytes. Antioxidants (Basel). 2020; 9(1). PMC: 7022695. DOI: 10.3390/antiox9010063. View

18.

Dong J, Li J, Cui L, Wang Y, Lin J, Qu Y . Cortisol modulates inflammatory responses in LPS-stimulated RAW264.7 cells via the NF-κB and MAPK pathways. BMC Vet Res. 2018; 14(1):30. PMC: 5789647. DOI: 10.1186/s12917-018-1360-0. View

19.

Zhao Y, Guan F, Wang G, Miao L, Ding J, Guan G . Astaxanthin preparation by lipase-catalyzed hydrolysis of its esters from Haematococcus pluvialis algal extracts. J Food Sci. 2012; 76(4):C643-50. DOI: 10.1111/j.1750-3841.2011.02119.x. View

20.

Nita M, Grzybowski A . The Role of the Reactive Oxygen Species and Oxidative Stress in the Pathomechanism of the Age-Related Ocular Diseases and Other Pathologies of the Anterior and Posterior Eye Segments in Adults. Oxid Med Cell Longev. 2016; 2016:3164734. PMC: 4736974. DOI: 10.1155/2016/3164734. View