[KSCI] Korea Science Citation Index Service

http://dx.doi.org/10.4014/jmb.0901.0004

In Vitro Antioxidant Activity of 5-HMF Isolated from Marine Red Alga Laurencia undulata in Free Radical Mediated Oxidative Systems

Li, Yong-Xin (Department of Chemistry, Pukyong National University)
Li, Yong (Marine Bioprocess Research Center, Pukyong National University)
Qian, Zhong-Ji (Marine Bioprocess Research Center, Pukyong National University)
Kim, Moon-Moo (Department of Chemistry, Dong-Eui University)
Kim, Se-Kwon (Department of Chemistry, Pukyong National University)

Publication Information

Journal of Microbiology and Biotechnology / v.19, no.11, 2009 , pp. 1319-1327 More about this Journal

Abstract

Marine red algae of genus Laurencia are becoming the most important resources to produce unique natural metabolites with wide bioactivities. However, reports related to Laurencia undulata, an edible species used as folk herb, are rarely found to date. In this research, 5-hydroxymethyl-2-furfural (5-HMF) was isolated and characterized by nuclear magnetic resonance (NMR) from Laurencia undulata as well as other marine algae. The following characteristics of 5-HMF were systematically evaluated: its antioxidant activities, such as typical free-radicals scavenging in vitro by electron spin resonance spectrometry (ESR) and intracellular reactive oxygen species (ROS) scavenging; membrane protein oxidation; oxidative enzyme myeloperoxidase (MPO) inhibition; as well as expressions of antioxidative enzymes glutathione (GSH) and superoxide dismutase (SOD) on the gene level using the polymerase chain reaction (PCR) method. The results demonstrated that 5-HMF could be developed as a novel marine natural antioxidant or potential precursor for practical applications in the food, cosmetic, and pharmaceutical fields.

Keywords

Marine alga; Laurencia undulata; 5-HMF; antioxidation; PCR technique;

Citations & Related Records

Times Cited By KSCI : 2 (Citation Analysis)
Times Cited By Web Of Science : 11 (Related Records In Web of Science)

Reference
Cited By KSCI

1	Grune, T., L. Klotz, J. Gieche, M. Rudeck, and H. Sies. 2001. Protein oxidation and proteolysis by the nonradical oxidants singlet oxygen or peroxynitrite. Free Rad. Biol. Med. 30: 1243-1253 DOI ScienceOn
2	Jung, W.K., I. Choi, S. Oh, S. G. Park, S. K. Seo, S. W. Lee, et al. 2008. Anti-asthmatic effect of marine red alga (Laurencia undulata) polyphenolic extracts in a murine model of asthma. Food Chem. Toxicol. 47: 293-297 PUBMED ScienceOn
3	Reed, D. J. and M. W. Farris. 1984. Glutathion depletion and susceptibility. Pharmacol. Rev. 36: 25S-33S PUBMED
4	Silva, B. A., F. Ferreres, J. O. Malva, and A. C. P. Dias. 2005. Phytochemical and antioxidant characterization of Hypericum perforatum alcoholic extracts. Food Chem. 90: 157-167 DOI ScienceOn
5	Suzuki, M., E. Kurosawa, and K. Kurata. 1987. (E)-2-Tridecyl-2-heptadecenal, an unusual metabolite from the red alga Laurencia species. Bull. Chem. Soc. Jpn. 60: 3793-3794 DOI
6	Zhong, X. Y., W. Holzgreve, and D. J. Huang. 2008. Isolation of cell-free RNA from maternal plasma. Methods Mol. Biol. 444: 269-273 DOI PUBMED ScienceOn
7	Baik, J. S., S. S. Kim, J. A. Lee, T. R. Oh, J. Y. Kim, N. H. Lee, and C. G. Hyun, 2008. Chemical composition and biological activities of essential oils extracted from Korean endemic citrus species. J. Microbiol. Biotechnol. 18: 74-79 PUBMED ScienceOn
8	Bradly, P. P., D. A. Priebat, R. D. Christensen, and G. Rothstein. 1982. Measurement of cutaneous inflammation: Estimation of neutrophil content with an enzyme marker. J. Invest. Dermatol. 78: 206-209 DOI ScienceOn
9	Pan, Y. M., J. C. Zhu, H. S. Wang, X. P. Y. Zhang, C. H. He, X. W. Ji, and H. Y. Li. 2007. Antioxidant activity of ethanolic extract of Cortex fraxini and use in peanut oil. Food Chem. 103: 913-918 DOI ScienceOn
10	Odetti, P., S. Garibaldi, G. Noberasco, I. Aragno, S. Valentini, N. Traverso, and U. M. Marinari. 1999. Levels of carbonyl groups in plasma proteins of type 2 diabetes mellitus subjects. Acta Diabetol. 36: 179-183 DOI ScienceOn
11	Davies, K. J., A. T. Quintanilha, G. A. Brooks, and L. Packer. 1982. Free radicals and tissue damage produced by exercise. Biochem. Biophys. Res. Commun. 107: 1198-1205 DOI ScienceOn
12	Guo, Q., B. Zhao, S. Shen, J. Hou, J. Hu, and W. Xin. 1999. ESR study on the structure-antioxidant activity relationship of tea catechins and their epimers. Biochem. Biophys. Acta 1427: 13-23 DOI
13	Reo, S. J., J. P. Kim, W.K. Jung, N. H. Lee, H. S. Kang, E. M. Jun, et al. 2008. Identification of chemical structure and free radical scavenging activity of diphlorethohydroxycarmalol isolated from a brown alga, Ishige okamurae. J. Microbiol. Biotechnol. 18: 676-681 PUBMED ScienceOn
14	Hiramoto, K., H. Johkoh, K. I. Sako, and K. Kikugawa. 1993. DNA breaking activity of the carbon-centered radical generated from 2,2'-azobis(2-amidinopropane) hydrochloride (AAPH). Free Radical Res. Commun. 19: 323-332 DOI
15	Ji, N. Y., X. M. Li, K. Li, L. P. Ding, J. B. Gloer, and B. G. Wang. 2007. Diterpenes, sesquiterpenes, and a $C_{15}$ -acetogenin from the marine red alga Laurencia mariannensis. J. Nat. Prod. 70: 1901-1905 DOI ScienceOn
16	Liang, H., J. He, A. G. Ma, P. H. Zhang, S. L. Bi, and D. Y. Shi. 2007. Effect of ethanol extract of alga Laurencia supplementation on DNA oxidation and alkylation damage in mice. Asia Pac. J. Clin. Nutr. 16(Suppl): 164-168 PUBMED
17	Antolovich, M., P. D. Prenzler, E. Patsalides, S. McDonald, and K. Robards. 2002. Methods for testing antioxidant activity. Analyst 127: 183-198 DOI ScienceOn
18	Xu, Q., Y. H. Li, and X. Y. Lu. 2007. Investigation on influencing factors of 5-HMF content in Schisandra. J. Zhejiang Univ. Sci. B 8: 439-445 DOI ScienceOn
19	Rosen, G M. and E. J. Rauckman. 1984. Spin trapping of superoxide and hydroxyl radicals. Methods Enzymol. 105: 198-209 DOI PUBMED ScienceOn
20	Winterbourn, C. C., M. C. M. Vissers, and A. J. Kettle. 2000. Myeloperoxidase. Curr. Opin. Hematol. 7: 53-58 DOI ScienceOn
21	Rajapakse, N., M. M. Kim, E. Mendis, and S. K. Kim. 2007. Inhibition of free radical-mediatedoxidation of cellular biomolecules by carboxylated chitooligosaccharides. Bioorg. Med. Chem. 15: 997-1003 DOI ScienceOn
22	Nanjo, F., K. Goto, R. Seto, M. Suzuki, M. Sakai, and Y. Hara. 1996. Scavenging effects of tea catechins and their derivatives on 1,1-diphenyl-2-picrylhydrazyl radical. Free Radical Biol. Med. 21: 895-902 DOI ScienceOn
23	Sun, J., D. Y. Shi, M. Ma, S. Li, S. J. Wang, L. J. Han, et al. 2005. Sesquiterpenes from the red alga Laurencia tristicha. J. Nat. Prod. 68: 915-919 DOI ScienceOn
24	Fu, Z. Q., M. Y. Wang, and B. C. Cai. 2008. Discussion of 5-hydroxymethylfurfural (5-HMF) in 'Chinese Native Medicine Research Presents.' Zhongguo Zhong Yao Za Zhi 26: 3
25	Levine, R. L., D. Garland, C. N. Oliver, A. Amici, I. Climent, A. G. Lenz, B. W. Ahn, S. Shaltiel, and E. R. Stadtrnan. 1990. Determination of carbonyl content in oxidatively modified proteins. Methods Enzymol. 186: 464-478 DOI PUBMED
26	Beckman, J. S., T. W. Beckman, J. Chen, P. A. Marshall, and B. A. Freeman. 1990. Apparent hydroxyl radical productionby peroxynitrite: Implications for endothelial injury from nitric oxide and superoxide. Proc. Natl. Acad. Sci. U.S.A. 87: 1620-1624 DOI ScienceOn
27	Pec, M. K., K. Moser-Thier, J. J. Fernandez, M. L. Souto, and E. Kubista. 1999. Growth inhibition by dehydrothyrsiferol - a non-Pgp modulator, derived from a marine red alga - in human breast cancer cell lines. Int. J. Oncol. 14: 739-743 PUBMED ScienceOn
28	Ding, X., M. Y. Wang, Z. L. Yu, W. Hu, and B. C. Cai. 2008. Studies on separation, appraisal and the biological activity of 5-HMF in Comus officinalis. Zhongguo Zhong Yao Za Zhi 3: 4
29	Liu, C. L., Y. S. Chen, J. H. Yang, B. H. Chiang, and C. K. Hsu. 2007. Trace element water improves the antioxidant activity of buckwheat (Fagopyrum esculentum Moench) sprouts. J. Agric. Food Chem. 55: 8934-8940 DOI ScienceOn

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9	Yeonwoo Song. (2009) 한국식품영양과학회지 감귤박 에탄올추출물과 열수추출물의 영양성분 및 항산화 활성 / 42 (9) , 1345
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