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Phlorotannins as Radical Scavengers from the Extract of Sargassum ringgoldianum

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Abstract

To screen algal phlorotannins with antioxidative activities, 50% ethanol extracts of 25 Japanese marine algae were evaluated. Scavenging activity against superoxide anion radicals was frequently found with a high content of total phenolic compounds. Among these, the extract from the brown seaweed, Sargassum ringgoldianum, showed the strongest scavenging activity. The active fraction contained a mixture of high molecular weight polyphenols, phlorotannins that were found to be polymerized bifuhalol, as analyzed by matrix-assisted laser desorption/ionization time-of-flight mass spectrometry (MALDI-TOF MS). The scavenging activity of the fraction against superoxide anion radicals was estimated to be 1.0 μg/ml (IC50), which were approximately five times stronger than that of catechin.

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References

  • Y Abe S Okada R Nakao T Horii H Inoue S Taniguchi S Yamabe (1992) ArticleTitleA molecular orbital study on the reactivity of L-ascorbic acid towards OH radical J Chem Soc Perkin Trans 2 2221–2232

    Google Scholar 

  • IFF Benzie YT Szeto (1999) ArticleTitleTotal antioxidant capacity of teas by the ferric reducing/antioxidant power assay J Agric Food Chem 47 633–636 Occurrence Handle10.1021/jf9807768

    Article  Google Scholar 

  • BHJ Bielski (1982) Chemistry of ascorbic acid radicals PA Seib BM Tolbert (Eds) Ascorbic Acid: Chemistry, Metabolism and Users, Advances in Chemistry Series, Vol. 200 American Chemical Society Washington, DC 81–100

    Google Scholar 

  • M Colon P Guevara WH Gerwick D Ballantine (1987) ArticleTitle5′-Hydroxyisoavrainvilleol, a new diphenylmethane derivative from the tropical green alga Avrainvillea nigricans J Nat Prod 50 368–374 Occurrence Handle10.1021/np50051a005

    Article  Google Scholar 

  • H Fujiki M Suganuma S Okabe N Sueoka A Komori E Sueoka T Kozu Y Tada K Suga K Imai K Nakachi (1998) ArticleTitleCancer inhibition by green tea Mutat Res 402 307–310

    Google Scholar 

  • F Galli M Piroddi C Annetti C Aisa E Floridi A Floridi (2005) ArticleTitleOxidative stress and reactive oxygen species Contrib Nephrol 149 240–260 Occurrence Handle10.1159/000085686

    Article  Google Scholar 

  • KW Glombitza M Keusgen (1995) ArticleTitleFuhalols and deshydroxyfuhalols from the brown alga Sargassum spinuligerum Phytochemistry 38 987–995 Occurrence Handle10.1016/0031-9422(94)00735-C

    Article  Google Scholar 

  • KW Glombitza HU Rosener (1974) ArticleTitleBifhalol: Ein diphenylather aus Bifurcaria bifurcata Phytochemistry 13 1245–1247 Occurrence Handle10.1016/0031-9422(74)80110-X

    Article  Google Scholar 

  • F Hashimoto M Ono C Masuoka Y Ito Y Sakata K Shimizu G Nonaka I Nishioka T Nohara (2003) ArticleTitleEvaluation of the anti-oxidative effect (in vitro) of tea polyphenols Biosci Biotechnol Biochem 67 396–401 Occurrence Handle10.1271/bbb.67.396

    Article  Google Scholar 

  • E Haslam (1989) Plant Polyphenols: Vegetable Tannins Revisited Cambridge University Press Cambridge, UK

    Google Scholar 

  • RA Larson (1988) ArticleTitleThe antioxidants of higher plants Phytochemistry 27 969–978 Occurrence Handle10.1016/0031-9422(88)80254-1

    Article  Google Scholar 

  • JH Lee JC Park JS Choi (1996) ArticleTitleThe antioxidant activity of Ecklonia stolonifera Arch Pharm Res 19 223–227 Occurrence Handle10.1007/BF02976894

    Article  Google Scholar 

  • SN Lim PCK Cheung VEC Ooi PO Ang (2002) ArticleTitleEvaluation of antioxidative activity of extracts from a brown seaweed, Sargassum siliquastrum J Agric Food Chem 50 3862–3866 Occurrence Handle10.1021/jf020096b

    Article  Google Scholar 

  • PD Maldonado I Rivero-Cruz R Mata J Pedraza-Chaverri (2005) ArticleTitleAntioxidant activity of A-type proanthocyanidins from Geranium niveum (Geraniaceae) J Agric Food Chem 53 1996–2001 Occurrence Handle10.1021/jf0483725

    Article  Google Scholar 

  • JM McCord I Fridovich (1969) ArticleTitleThe utility of superoxide dismutase in studying free radical reactions. I. Radicals generated by the interaction of sulfite, dimethyl sulfoxide, and oxygen J Biol Chem 244 6056–6063

    Google Scholar 

  • S Miura J Watanabe T Tomita M Sano I Tomita (1994) ArticleTitleThe inhibitory effects of tea polyphenols (flavan-3-ol derivatives) on Cu2+-mediated oxidative modification of low-density lipoprotein Biol Pharm Bull 17 1567–1572

    Google Scholar 

  • M Nakai M Harada K Nakahara K Akimo H Shibata W Miki Y Kiso (2003) ArticleTitleNovel antioxidative metabolites in rat liver with ingested sesamin J Agric Food Chem 51 1666–1670 Occurrence Handle10.1021/jf0258961

    Article  Google Scholar 

  • C Ogino Y Taki (1957) ArticleTitleStudies on the tannin of brown alga, Sargassum ringgoldianum Harv J Tokyo Univ Fish 43 1–5

    Google Scholar 

  • T Okuda (1999) ArticleTitleNovel aspects of tannins—renewed concepts and structure-activity relationships Curr Org Chem 3 609–622

    Google Scholar 

  • T Okuda (2005) ArticleTitleSystematics and health effects of chemically distinct tannins in medicinal plants Phytochemistry 66 2012–2013 Occurrence Handle10.1016/j.phytochem.2005.04.023

    Article  Google Scholar 

  • T Okuda T Yoshida K Mori T Hatano (1981) ArticleTitleTannins of medical plants and drugs Heterocycles 15 1323–1348 Occurrence Handle10.3987/S-1981-02-1323

    Article  Google Scholar 

  • MA Ragan JS Craigie (1976) ArticleTitlePhysodes and the phenolic compounds of brown algae. Isolation and characterization of phloroglucinol polymers from Fucus vesiculosus (L.) Can J Biochem 54 66–73 Occurrence Handle10.1139/v76-012

    Article  Google Scholar 

  • MA Ragan JS Craigie (1978) Phenolic compounds in brown and red algae JA Hellebust JS Craigie (Eds) Handbook of Phycological Methods—Physiological and Biochemical Methods Cambridge University Press Cambridge, UK 157–179

    Google Scholar 

  • CS Rice-Evans NJ Miller G Paganga (1996) ArticleTitleStructure-antioxidant activity relationships of flavonoids and phenolic acids Free Radic Biol Med 20 933–956 Occurrence Handle10.1016/0891-5849(95)02227-9

    Article  Google Scholar 

  • ZH Shao LB Becker TL Hoek ParticleVanden PT Schumacker CQ Li D Zhao K Wojcik T Anderson Y Qin L Dey CS Yuan (2003) ArticleTitleGrape seed proanthocyanidin extract attenuates oxidant injury in cardiomyocytes Pharmacol Res 47 463–469 Occurrence Handle10.1016/S1043-6618(03)00041-0

    Article  Google Scholar 

  • VL Singleton JA Rossi (1965) ArticleTitleColorimetry of total phenolics with phosphomolybdic-phosphotungstic acid reagents Am J Enol Vitic 16 144–158

    Google Scholar 

  • Surh YJ, Chun KS, Cha HH, Han SS, Keum YS, Park KK, Lee SS (2001) Molecular mechanisms underlying chemopreventive activities of anti-inflammatory phytochemicals: down-regulation of COX-2 and iNOS through suppression of NF-κB activation. Mutat Res Sept 1, 243–268

    Google Scholar 

  • S Takamatsu DG Nagle WH Gerwick (2004) ArticleTitleSecondary metabolites from marine cyanobacteria and algae inhibit LFA-1/ICAM-1-mediated cell adhesion Planta Med 70 127–131 Occurrence Handle10.1055/s-2004-815488

    Article  Google Scholar 

  • FB Whitfield F Helidoniotis KJ Shaw D Svoronos (1999) ArticleTitleDistribution of bromophenols in species of marine algae from eastern Australia J Agric Food Chem 47 2367–2373 Occurrence Handle10.1021/jf981080h

    Article  Google Scholar 

  • X Xu F Song S Wang S Li F Xiao J Zhao Z Yang S Shang L Yang J Shi (2004) ArticleTitleDibenzyl bromophenols with diverse dimerization patterns from the brown alga Leathesia nana J Nat Prod 67 1661–1666 Occurrence Handle10.1021/np0400609

    Article  Google Scholar 

  • XJ Yan XC Li CX Zhou X Fan (1996) ArticleTitlePrevention of fish oil rancidity by phlorotannins from Sargassum kjellmanianum J Appl Phycol 8 201–203 Occurrence Handle10.1007/BF02184972

    Article  Google Scholar 

  • T Yoshida T Hatano H Ito T Okuda (1999) ArticleTitleHighly oxidized ellagitannins and their biological activity Basic Life Sci 66 127–144

    Google Scholar 

  • J Zhao X Fan S Wang S Li S Shang Y Yang N Xu Y Lu J Shi (2004) ArticleTitleBromophenol derivatives from the red alga Rhodomela confervoides J Nat Prod 67 1032–1035 Occurrence Handle10.1021/np030546+

    Article  Google Scholar 

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Correspondence to Masaaki Nakai.

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Nakai, M., Kageyama, N., Nakahara, K. et al. Phlorotannins as Radical Scavengers from the Extract of Sargassum ringgoldianum . Mar Biotechnol 8, 409–414 (2006). https://doi.org/10.1007/s10126-005-6168-9

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