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Ishigoside, a new glyceroglycolipid isolated from the brown alga Ishige okamurae

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Abstract

A new glyceroglycolipid, ishigoside (1, 2-di-O-palmitoyl-3-O-(6-deoxy-6-amino)-α-D-glucopyranosyl-glycerol, 1), along with two known compounds were isolated from the brown alga Ishige okamurae. The structure of the new compound was determined on the basis of spectroscopic analysis, including 1D and 2D NMR, MS techniques and chemical methods. Moreover, direct free radical scavenging activities of ishigoside were investigated by electron spin resonance spectrometry (ESR) technique. The results suggested that ishigoside was a potential free-radical scavenger against DPPH, hydroxyl, alkyl, and superoxide radicals with the EC50 of 31.2, 16.7, 22.7, and 26.8 μM, respectively.

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References

  1. Squadrito, G.L. and W. A. Pryor (1998) Oxidative chemistry of nitric oxide: the roles of superoxide, peroxynitrite, and carbon dioxide. Free Radic. Biol. Med. 25: 392–403.

    Article  CAS  Google Scholar 

  2. Halliwell, B. (1994) Free radicals, antioxidants, and human disease: curiosity, cause, or consequence? Lancent 344: 721–724.

    Article  CAS  Google Scholar 

  3. Moskovitz, J., M. B. Yim, and P. B. Chock (2002) Free radicals and disease. Arch. Biochem. Biophys. 397: 354–359.

    Article  CAS  Google Scholar 

  4. Stohs, S. J. (1995) The role of free radicals in toxicity and disease. J. Basic Clin. Physiol. Pharmacol. 6: 205–228.

    CAS  Google Scholar 

  5. Castro, L. and B. A. Freeman (2001) Reactive oxygen species in human health and disease. Nutrition 17: 161–165.

    Article  CAS  Google Scholar 

  6. Choi, D. B., S. S. Park, J. L. Ding, and W. S. Cha (2007) Effects of Fomitopsis pinicola extracts on antioxidant and antitumor activities. Biotechnol. Bioprocess Eng. 12: 516–524.

    Article  CAS  Google Scholar 

  7. Koga, T., K. Moro, K. Nakamori, J. Yamakoshi, H. Hosoyama, S. Kataoka, and T. Ariga (1999) Increase of antioxidative potential of rat plasma by oral administration of proanthocyanidin-rich extract from grape seeds. J. Agric. Food Chem. 47: 1892–1897.

    Article  CAS  Google Scholar 

  8. Kang, K. S., I. D. Kim, R. H. Kwon, and B. J. Ha (2008) Undaria pinnatifida fucoidan extract protects against CCl4-induced oxidative stress. Biotechnol. Bioprocess Eng. 13: 168–173.

    Article  CAS  Google Scholar 

  9. Kim, J. S., Y. H. Kim, Y. W. Seo, and S. Park (2007) Quorum sensing inhibitors from the red alga, Ahnfeltiopsis flabelliformis. Biotechnol. Bioprocess Eng. 12:308–311.

    Article  CAS  Google Scholar 

  10. Lee, H. J., Y. A. Kim, J. W. Ahn, H. J. Na, H. M. Kim, and Y. W. Seo (2006) Screening of Korean marine plants for their inhibitory effect on histamine release from RPMC in vitro. Biotechnol. Bioprocess Eng. 11:80–83.

    Article  CAS  Google Scholar 

  11. Cho, J. Y., J. S. Choi, S. E. Kang, J. K. Kim, H. W. Shin, and Y. K. Hong (2005) Isolation of antifouling active pyroglutamic acid, triethyl citrate and di-n-octylphthalate from the brown seaweed Ishige okamurae. J. Appl. Phycol. 17: 431–435.

    Article  Google Scholar 

  12. Tang, H. F., Y. H. Yi, X. S. Yao, Q. Z. Xu, T. S. Lv, and S. Y. Zhang (2002) Sterol constituents from marine brown alga Ishige okamurae. Chin. J. Mar. Drugs 21: 1–4.

    Google Scholar 

  13. Tang, H. F., Y. H. Yi, X. S. Yao, S. Y. Zhang, Q. Z. Xu, and S. L. Mao (2003) Studies on chemical constituents from marine brown alga Ishige okamurae (II). Chin. J. Mar. Drugs 22: 8–12.

    CAS  Google Scholar 

  14. Tang, H. F., Y. H. Yi, X. S. Yao, J. H. Wu, S. Y. Zhang, and Q. Z. Xu (2002) Studies on chemical constituents from marine brown alga Ishige okamurae (III). China J. Chin. Mater. Med. 27: 269–273.

    CAS  Google Scholar 

  15. Toume, K., M. Miyata, K. Egawa, K. Nose, M. Hayashi, K. Komiyama, and M. Ishibashi (2004) Isolation of diphlorethohydroxycarmalol from a brown alga Ishige okamurae. Nat. Med. 58: 79–80.

    CAS  Google Scholar 

  16. 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 Radic. Biol. Med. 21: 895–902.

    Article  CAS  Google Scholar 

  17. Rosen, G. M. and E. J. Rauckman (1984) Spin trapping of superoxide andhydroxyl radicals. pp. 198–209. In: L. Packer (eds.). Methods in Enzymology. Academic Press, Orlando, FL, USA.

    Google Scholar 

  18. Hiramoto, K., H. Johkoh, K. Sako, and K. Kikugawa (1993) DNA breaking activity of the carbon-centered radical generated from 2, 2′-azobis(2-amidinopropane) hydrochloride (AAPH). Free Radic. Res. Commun. 19:323–332.

    Article  CAS  Google Scholar 

  19. 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. Biochim. Biophys. Acta 1427: 13–23.

    CAS  Google Scholar 

  20. Lee, C. K., P. H. Lee, and Y. H. Kuo (2001) The chemical constituents from the aril of Cassia fistula L. J. Chin. Chem. Soc. 48: 1053–1058.

    CAS  Google Scholar 

  21. Yamaoka, N., T. Usui, H. Sugiyama, and S. Seto (1974) 13C NMR spectra of some aminosugars and sugarantibiotics, neomycin and kanamycin. Chem. Pharm. Bull. 22: 2196–2200.

    CAS  Google Scholar 

  22. Andersen, R. J. and O. Taglialatela-Scafati (2005) Avrainvilloside, a 6-deoxy-6-aminoglucoglycerolipid from the green alga Avrainvillea nigricans. J. Nat. Prod. 68:1428–1430.

    Article  CAS  Google Scholar 

  23. Schwender, J., M. Seemann, H. K. Lichtenthaler, and M. Rohmer (1996) Biosynthesis of isoprenoids (carotenoids, sterols, prenyl side-chains of chlorophylls and plastoquinone) via a novel pyruvate/glyceraldehyde 3-phosphate non-mevalonate pathway in the green alga Scenedesmus obliquus. Biochem. J. 316: 73–80.

    CAS  Google Scholar 

  24. Kim, J. D. and C. G. Lee (2005) Systemic optimization of microalgae for bioactive compound production. Biotechnol. Bioprocess Eng. 10: 418–424.

    Article  CAS  Google Scholar 

  25. Khotimchenko, S. V. (2002) Distribution of glycerolglycolipids in marine algae and grasses. Chem. Nat. Comp. 38: 223–229.

    Article  CAS  Google Scholar 

  26. Zhou, B. N., S. Tang, R. K. Johnson, M. P. Mattern, J. S. Lazo, E. R. Sharlow, K. Harich, and D. G. I. Kingston (2005) New glycolipid inhibitors of Myt1 kinase. Tetrahedron 61: 883–887.

    Article  CAS  Google Scholar 

  27. Sachindra, N. M., E. Sato, H. Maeda, M. Hosokawa, Y. Niwano, M. Kohno, and K. Miyashita (2007) Radical scavenging and singlet oxygen quenching activity of marine carotenoid fucoxanthin and its metabolites. J. Agric. Food Chem. 55: 8516–8522.

    Article  CAS  Google Scholar 

  28. Antolovich, M., P. D. Prenzler, E. Patsalides, S. McDonald, and K. Robards (2002) Methods for testing antioxidant activity. Analyst 127: 183–198.

    Article  CAS  Google Scholar 

  29. Makino, K., T. Hagiwara, and A. Murakami (1991) A mini review: fundamental aspects of spin trapping with DMPO. Radiat. Phys. Chem. 37: 657–665.

    CAS  Google Scholar 

  30. Noguchi, N., A. Watanabe, and H. Shi (2000) Diverse functions of antioxidants. Free Radic. Res. 33: 809–817.

    Article  CAS  Google Scholar 

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Correspondence to Se-Kwon Kim.

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Zou, Y., Li, Y., Kim, MM. et al. Ishigoside, a new glyceroglycolipid isolated from the brown alga Ishige okamurae . Biotechnol Bioproc E 14, 20–26 (2009). https://doi.org/10.1007/s12257-008-0131-3

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