全部 标题 作者
关键词 摘要

OALib Journal期刊
ISSN: 2333-9721
费用:99美元

查看量下载量

相关文章

更多...
Marine Drugs  2013 

Cellular Antioxidant Effect of Four Bromophenols from the Red Algae, Vertebrata lanosa

DOI: 10.3390/md11082769

Keywords: marine algae, macro algae, bioactivity, cellular antioxidant assay, ORAC

Full-Text   Cite this paper   Add to My Lib

Abstract:

Three known bromophenols, 2,3-dibromo-4,5-dihydroxybenzylaldehyde ( 1), 2,2′,3-tribromo-3′,4,4′,5-tetrahydroxy-6′-hydroxymethyldiphenylmethane ( 2) and bis(2, 3-dibromo-4,5-dihydroxylbenzyl) ether ( 3), and one new one, 5,5″-oxybis(methylene)bis (3-bromo-4-(2′,3′-dibromo-4′,5′-dihydroxylbenzyl)benzene-1,2-diol) ( 4), were isolated from an extract of the red alga, Vertebrata lanosa. The antioxidant activity of these four bromophenols was examined using one biochemical and two cellular assays: Oxygen Radical Absorbance Capacity (ORAC), Cellular Antioxidant Activity (CAA) and Cellular Lipid Peroxidation Antioxidant Activity (CLPAA) assays. Compound 2 distinguished itself by showing potent activity, having a better antioxidant effect than luteolin in both the CAA and CLPAA assays and of quercetin in the CLPAA assay. Although several bromophenols are known to be potent antioxidants in biochemical assays, this is the first time their cellular antioxidant activity has been demonstrated.

References

[1]  El Gamal, A.A. Biological importance of marine algae. Saudi Pharm. J. 2010, 18, 1–25, doi:10.1016/j.jsps.2009.12.001.
[2]  Whitfield, F.B.; Helidoniotis, F.; Shaw, K.J.; Svoronos, D. Distribution of bromophenols in species of marine algae from eastern Australia. J. Agric. Food Chem. 1999, 47, 2367–2373, doi:10.1021/jf981080h.
[3]  Liu, M.; Hansen, P.E.; Lin, X. Bromophenols in marine algae and their bioactivities. Mar. Drugs 2011, 9, 1273–1292, doi:10.3390/md9071273.
[4]  Flodin, C.; Helidoniotis, F.; Whitfield, F.B. Seasonal variation in bromophenol content and bromoperoxidase activity in Ulva lactuca. Phytochemistry 1999, 51, 135–138.
[5]  Li, K.; Li, X.M.; Gloer, J.B.; Wang, B.G. Isolation, characterization, and antioxidant activity of bromophenols of the marine red alga Rhodomela confervoides. J. Agric. Food Chem. 2011, 59, 9916–9921, doi:10.1021/jf2022447.
[6]  Duan, X.-J.; Li, X.-M.; Wang, B.-G. Highly brominated mono- and bis-phenols from the marine red alga Symphyocladia latiuscula with radical-scavenging activity. J. Nat. Prod. 2007, 70, 1210–1213, doi:10.1021/np070061b.
[7]  Li, K.; Li, X.-M.; Ji, N.-Y.; Wang, B.-G. Natural bromophenols from the marine red alga Polysiphonia urceolata (Rhodomelaceae): Structural elucidation and DPPH radical-scavenging activity. Bioorganic Med. Chem. 2007, 15, 6627–6631, doi:10.1016/j.bmc.2007.08.023.
[8]  Li, K.; Li, X.-M.; Ji, N.-Y.; Wang, B.-G. Bromophenols from the marine red alga Polysiphonia urceolata with DPPH radical scavenging activity. J. Nat. Prod. 2008, 71, 28–30, doi:10.1021/np070281p.
[9]  Lee, J.-H.; Lee, T.-K.; Kang, R.-S.; Shin, H.-J.; Lee, H.-S. The in vitro antioxidant activities of the bromophenols from the red alga Tichocarpus crinitus and phenolic derivatives. J. Korean Magn. Reson. Soc. 2007, 11, 56–63.
[10]  Saito, T.; Ando, Y. Bromine compounds in sea-weeds. I. On a bromophenolic compound obtained from the red algae, Polysiphonia Morrowii Harv. Nippon Kagaku Zassi 1955, 76, 478–479.
[11]  Zhao, J.; Fan, X.; Wang, S.; Li, S.; Shang, S.; Yang, Y.; Xu, N.; Lü, Y.; Shi, J. Bromophenol derivatives from the red alga Rhodomela confervoides. J. Nat. Prod. 2004, 67, 1032–1035, doi:10.1021/np030546+.
[12]  Guiry, M.D.; Guiry, G.M. World-wide Electronic Publication: National University of Ireland, Galway, Ireland. Available online: http://www.algaebase.org (accessed on 7 March 2012).
[13]  Zubia, M.; Fabre, M.S.; Kerjean, V.; Deslandes, E. Antioxidant and cytotoxic activities of some red algae (Rhodophyta) from Brittany coasts (France). Bot. Mar. 2009, 52, 268–277.
[14]  Devasagayam, T.; Tilak, J.; Boloor, K.; Sane, K.S. Free radicals and antioxidants in human health: Current status and future prospects. J. Assoc. Physicians India 2004, 52, 794–804.
[15]  Wu, D.F.; Cederbaum, A.I. Alcohol, oxidative stress and free radical damage. Alcohol Res. Health 2003, 27, 277–284.
[16]  Mallick, N.; Mohn, F.H. Reactive oxygen species: Response of algal cells. J. Plant Physiol. 2000, 157, 183–193, doi:10.1016/S0176-1617(00)80189-3.
[17]  Kamalakar, G.; Komura, K.; Kubota, Y.; Sugi, Y. Friedel–Crafts benzylation of aromatics with benzyl alcohols catalyzed by heteropoly acids supported on mesoporous silica. J. Chem. Technol. Biotechnol. 2006, 81, 981–988, doi:10.1002/jctb.1488.
[18]  Huang, D.; Ou, B.; Prior, R.L. The Chemistry behind Antioxidant Capacity Assays. J. Agric. Food Chem. 2005, 53, 1841–1856, doi:10.1021/jf030723c.
[19]  Huang, D.; Ou, B.; Hampsch-Woodill, M.; Flanagan, J.A.; Prior, R.L. High-Throughput assay of oxygen radical absorbance capacity (orac) using a multichannel liquid handling system coupled with a microplate fluorescence reader in 96-well format. J. Agric. Food Chem. 2002, 50, 4437–4444, doi:10.1021/jf0201529.
[20]  Wolfe, K.L.; Liu, R.H. Structure–Activity relationships of flavonoids in the cellular antioxidant activity assay. J. Agric. Food Chem. 2008, 56, 8404–8411, doi:10.1021/jf8013074.
[21]  Hofer, T.; Eriksen, T.E.; Hansen, E.; Varmedal, I.; Jensen, I.-J.; Hammer-Andersen, J.; Olsen, R.L. Cellular and Chemical Assays for Discovery of Novel Antioxidants in Marine Organisms. In Studies on Experimental Models; Basu, S., Wiklund, L., Eds.; Humana Press: New York, NY, USA, 2011; pp. 637–657.
[22]  Wolfe, K.L.; Liu, R.H. Cellular antioxidant activity (CAA) assay for assessing antioxidants, foods, and dietary supplements. J. Agric. Food Chem. 2007, 55, 8896–8907, doi:10.1021/jf0715166.
[23]  Pap, E.H.W.; Drummen, G.P.C.; Winter, V.J.; Kooij, T.W.A.; Rijken, P.; Wirtz, K.W.A.; Op den Kamp, J.A.F.; Hage, W.J.; Post, J.A. Ratio-fluorescence microscopy of lipid oxidation in living cells using C11-BODIPY581/591. FEBS Lett. 1999, 453, 278–282, doi:10.1016/S0014-5793(99)00696-1.
[24]  Drummen, G.P.C.; van Liebergen, L.C.M.; Op den Kamp, J.A.F.; Post, J.A. C11-BODIPY581/591, an oxidation-sensitive fluorescent lipid peroxidation probe: (micro)Spectroscopic characterization and validation of methodology. Free Radic. Biol. Med. 2002, 33, 473–490, doi:10.1016/S0891-5849(02)00848-1.
[25]  Liu, R.H.; Finley, J. Potential cell culture models for antioxidant research. J. Agric. Food Chem. 2005, 53, 4311–4314, doi:10.1021/jf058070i.
[26]  Fan, X.; Xu, N.J.; Shi, J.G. Two new bromophenols from red alga Rhodomela confervoides. Chinese Chem. Lett. 2003, 14, 939–941.
[27]  Gottlieb, H.E.; Kotlyar, V.; Nudelman, A. NMR Chemical Shifts of Common Laboratory Solvents as Trace Impurities. J. Org. Chem. 1997, 62, 7512–7515, doi:10.1021/jo971176v.
[28]  Katsui, N.; Suzuki, Y.; Kitamura, S.; Irie, T. 5,6-Dibromoprotocatechualdehyde and 2,3-dibromo-4, 5-dihydroxybenzyl methyl ether: New dibromophenols from Rhodomela larix. Tetrahedron 1967, 23, 1185–1188, doi:10.1016/0040-4020(67)85068-3.
[29]  Kurihara, H.; Mitani, T.; Kawabata, J.; Takahashi, K. Two new bromophenols from the red alga Odonthalia corymbifera. J. Nat. Prod. 1999, 62, 882–884, doi:10.1021/np980324p.
[30]  Choi, J.S.; Park, H.J.; Jung, H.A.; Chung, H.Y.; Jung, J.H.; Choi, W.C. A cyclohexanonyl bromophenol from the red alga Symphyocladia latiuscula. J. Nat. Prod. 2000, 63, 1705–1706, doi:10.1021/np0002278.
[31]  Zhao, W.; Feng, X.; Ban, S.; Lin, W.; Li, Q. Synthesis and biological activity of halophenols as potent antioxidant and cytoprotective agents. Bioorg. Med. Chemi. Lett. 2010, 20, 4132–4134, doi:10.1016/j.bmcl.2010.05.068.
[32]  Chen, L.; Fang, Y.; Zhu, T.; Gu, Q.; Zhu, W. Gentisyl alcohol derivatives from the marine-derived fungus Penicillium terrestre. J. Nat. Prod. 2008, 71, 66–70, doi:10.1021/np070421v.
[33]  Gentry, C.L.; Egleton, R.D.; Gillespie, T.; Abbruscato, T.J.; Bechowski, H.B.; Hruby, V.J.; Davis, T.P. The effect of halogenation on blood-brain barrier permeability of a novel peptide drug. Peptides 1999, 20, 1229–1238, doi:10.1016/S0196-9781(99)00127-8.

Full-Text

Contact Us

service@oalib.com

QQ:3279437679

WhatsApp +8615387084133