ALGAE

  • 제26권2호
  • /
  • Pages.201-208
  • /
  • 2011
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  • 1226-2617(pISSN)
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  • 2093-0860(eISSN)
한국조류학회(藻類) (The Korean Society of Phycology)
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Antioxidant activity and cell protective effect of loliolide isolated from Sargassum ringgoldianum subsp. coreanum

  • Yang, Xiudong (Department of Marine Life Science, Jeju National University) ;
  • Kang, Min-Cheol (Department of Marine Life Science, Jeju National University) ;
  • Lee, Ki-Wan (Department of Marine Life Science, Jeju National University) ;
  • Kang, Sung-Myung (Department of Marine Life Science, Jeju National University) ;
  • Lee, Won-Woo (Department of Marine Life Science, Jeju National University) ;
  • Jeon, You-Jin (Department of Marine Life Science, Jeju National University)
  • 투고 : 2011.03.08
  • 심사 : 2011.05.25
  • 발행 : 2011.06.15
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초록

A monoterpene lactone, loliolide was successively isolated from brown seaweed, Sargassum ringgoldianum subsp. coreanum using column chromatography and high-performance liquid chromatography. The structure of the isolated compound was determined by comparison of EIMS and NMR spectral data with the previously published data. The antioxidant activities of loliolide were also evaluated by DPPH and $H_2O_2$ radical and intracellular reactive oxygen species scavenging assays, and it showed moderate activities in all antioxidant assays. Furthermore, loliolide was found to exert positive dose-dependent effects in the protective effects against $H_2O_2$-induced cell damage which were determined via MTT, Hoechst staining assays and cell cycle analysis. This is the first study on chemical constituent of this seaweed according to our best knowledge. These results clearly indicated that loliolide isolated from Sargassum ringgoldianum subsp. coreanum can protect the cells against $H_2O_2$-induced cell damage or apoptosis.

키워드

참고문헌

  1. Athukorala, Y. & Jeon, Y. -J. 2005. Screening for angiotensin 1-converting enzyme inhibitory activity of Ecklonia cava. J. Food Sci. Nutr. 10:134-139. https://doi.org/10.3746/jfn.2005.10.2.134
  2. Athukorala, Y., Lee, K. -W., Kim, S. -K. & Jeon, Y. -J. 2007. Anticoagulant activity of marine green and brown algae collected from Jeju Island in Korea. Bioresour. Technol. 98:1711-1716. https://doi.org/10.1016/j.biortech.2006.07.034
  3. Blois, M. S. 1958. Antioxidant determination by the use of a stable free radical. Nature 181:1199-1200. https://doi.org/10.1038/1811199a0
  4. Chang, H. W., Jang, K. H., Lee, D., Kang, H. R., Kim, T. -Y., Lee, B. H., Choi, B. W., Kim, S. & Shin, J. 2008. Monoglycerides from the brown alga Sargassum sagamianum: isolation, synthesis, and biological activity. Bioorg. Med. Chem. Lett. 18:3589-3592. https://doi.org/10.1016/j.bmcl.2008.05.008
  5. Gschwind, M. & Huber, G. 1995. Apoptotic cell death induced by β-amyloid 1-42 peptide is cell type dependent. J. Neurochem. 65:292-300.
  6. Heo, S. -J., Cha, S. -H., Lee, K. -W., Cho, S. K. & Jeon, Y. -J. 2005a. Antioxidant activities of chlorophyta and phaeophyta from Jeju Island. Algae 20:251-260. https://doi.org/10.4490/ALGAE.2005.20.3.251
  7. Heo, S. -J., Park, E. -J., Lee, K. -W. & Jeon, Y. -J. 2005b. Antioxidant activities of enzymatic extracts from brown seaweeds. Bioresour. Technol. 96:1613-1623. https://doi.org/10.1016/j.biortech.2004.07.013
  8. Hodges, R. & Porte, A. L. 1964. The structure of loliolide: A terpene from Lolium perenne. Tetrahedron 20:1463-1467. https://doi.org/10.1016/S0040-4020(01)99140-9
  9. Kim, D. -S. & Park, Y. -H. 1985. Uronic acid composition, block structure and some related properties of alginic acid: (3) on alginic acid prepared from Sargassum ringgoldianum. Bull. Korean Fish. Soc. 18:29-36.
  10. Kimura, J. & Maki, N. 2002. New loliolide derivatives from the brown alga Undaria pinnatifida. J. Nat. Prod. 65:57-58. https://doi.org/10.1021/np0103057
  11. Ko, S. -C., Kang, S. -M., Ahn, G., Yang, H. -P., Kim, K. -N. & Jeon, Y. -J. 2010. Antioxidant activity of enzymatic extracts from Sargassum coreanum. J. Korean Soc. Food Sci. Nutr. 39:494-499. https://doi.org/10.3746/jkfn.2010.39.4.494
  12. Kuniyoshi, M. 1985. Germination inhibitors from the brown alga Sargassum crassifolium (Phaeophyta, Sargassaceae). Bot. Mar. 28:501-503. https://doi.org/10.1515/botm.1985.28.11.501
  13. Li, Y., Qian, Z. -J., Ryu, B., Lee, S. -H., Kim, M. -M. & Kim, S. -K. 2009. Chemical components and its antioxidant properties in vitro: an edible marine brown alga, Ecklonia cava. Bioorg. Med. Chem. 17:1963-1973. https://doi.org/10.1016/j.bmc.2009.01.031
  14. Lizard, G., Fournel, S., Genestier, L., Dhedin, N., Chaput,C., Flacher, M., Mutin, M., Panaye, G. & Revillard, J. -P. 1995. Kinetics of plasma membrane and mitochondrial alterations in cells undergoing apoptosis. Cytometry 21:275-283. https://doi.org/10.1002/cyto.990210308
  15. Mosman, T. 1983. Rapid colorimetric assay for cellular growth and survival: application to proliferation and cytotoxicity assays. J. Immunol. Methods 65:55-63. https://doi.org/10.1016/0022-1759(83)90303-4
  16. Muller, H. E. 1985. Detection of hydrogen peroxide produced by microorganism on ABTS-peroxidase medium. Zentrabl. Bakteriol. Mikrobiol. Hyg. A 259:151-154.
  17. Nicoletti, I., Migliorati, G., Pagliacci, M. C., Grignani, F. & Riccardi, C. 1991. A rapid and simple method for measuring thymocyte apoptosis by propidium iodide staining and flow cytometry. J. Immunol. Methods 139:271-279. https://doi.org/10.1016/0022-1759(91)90198-O
  18. Okada, N., Shirata, K., Niwano, M., Koshino, H. & Uramoto, M. 1994. Immunosuppressive activity of a monoterpene from Eucommia ulmoides. Phytochemistry 37:281-282. https://doi.org/10.1016/0031-9422(94)85042-9
  19. Okunade, A. L. & Wiemer, D. F. 1985. (-)-loliolide, an antrepellent compound from Xanthoxyllum setulosum. J. Nat. Prod. 48:472-473. https://doi.org/10.1021/np50039a020
  20. Rosenkranz, A. R., Schmaldienst, S., Stuhlmeier, K. M., Chen, W., Knapp, W. & Zlabinger, G. J. 1992. A microplate assay for the detection of oxidative products using 2′,7′-dichlorefluorescein-diacetate. J. Immunol. Methods 156:39-45. https://doi.org/10.1016/0022-1759(92)90008-H
  21. Valdes, L. J. 3rd. 1986. Loliolide from Salvia divinorum. J. Nat. Prod. 49:171. https://doi.org/10.1021/np50043a031
  22. Wang, X. W., Zhan, Q., Coursen, J. D., Khan, M. A., Kontny, H. U., Yu, L., Hollander, M. C., O'Connor, P. M., Fornace, A. J. J. & Harris, C. C. 1999. GADD45 induction of a G2/M cell cycle checkpoint. Proc. Natl. Acad. Sci. U. S. A. 96:3706-3711. https://doi.org/10.1073/pnas.96.7.3706
  23. Zhang, X. -P., Pei, Y. -H., Liu, M. -S., Kang, S. -L. & Zhang, J. -Q. 2010. Chemical constituents from the leaves of Cerbera manghas. Asian Pac. J. Trop. Med. 3:109-111. https://doi.org/10.1016/S1995-7645(10)60046-6

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  8. Hydroxy lactones with the gem-dimethylcyclohexane system – Synthesis and antimicrobial activity 2015, https://doi.org/10.1016/j.arabjc.2015.02.018
  9. Towards a better understanding of medicinal uses of the brown seaweed Sargassum in Traditional Chinese Medicine: A phytochemical and pharmacological review vol.142, pp.3, 2012, https://doi.org/10.1016/j.jep.2012.05.046
  10. In Vitro and In Vivo Studies on Quercus acuta Thunb. (Fagaceae) Extract: Active Constituents, Serum Uric Acid Suppression, and Xanthine Oxidase Inhibitory Activity vol.2017, 2017, https://doi.org/10.1155/2017/4097195
  11. Protective effect of a marine polyphenol, dieckol against carbon tetrachloride-induced acute liver damage in mouse vol.35, pp.3, 2013, https://doi.org/10.1016/j.etap.2013.02.013
  12. Loliolide - the most ubiquitous lactone vol.0, pp.0, 2015, https://doi.org/10.1515/fobio-2015-0001
  13. Purification of antioxidative peptide from peptic hydrolysates of Mideodeok (Styela clava) flesh tissue vol.22, pp.2, 2013, https://doi.org/10.1007/s10068-013-0112-y
  14. Taraxerol 4-Methoxybenzoate, anin vitroInhibitor of Photosynthesis Isolated fromPavonia multifloraA.St-Hil. (Malvaceae) vol.13, pp.3, 2016, https://doi.org/10.1002/cbdv.201500049
  15. In vitroAnti-diabetic Activity and Chemical Characterization of an Apolar Fraction ofMorus albaLeaf Water Extract vol.27, pp.6, 2013, https://doi.org/10.1002/ptr.4803
  16. Isolation and identification of a phytotoxic substance from the emergent macrophyte Centrostachys aquatica vol.55, pp.1, 2014, https://doi.org/10.1186/s40529-014-0059-1
  17. Carpesium macrocephalum Attenuates Lipopolysaccharide-Induced Inflammation in Macrophages by Regulating the NF-κB/IκB-α, Akt, and STAT Signaling Pathways vol.41, pp.04, 2013, https://doi.org/10.1142/S0192415X13500626
  18. Preparative isolation of sargachromanol E from Sargassum siliquastrum by centrifugal partition chromatography and its anti-inflammatory activity vol.62, 2013, https://doi.org/10.1016/j.fct.2013.08.010
  19. Acanthus ebracteatus leaf extract provides neuronal cell protection against oxidative stress injury induced by glutamate vol.18, pp.1, 2018, https://doi.org/10.1186/s12906-018-2340-4
  20. Antioxidant and anti-inflammatory functionality of ten Sri Lankan seaweed extracts obtained by carbohydrase assisted extraction pp.2092-6456, 2018, https://doi.org/10.1007/s10068-018-0406-1
  21. Lam. vol.68, pp.4, 2018, https://doi.org/10.1080/09064710.2017.1401114
  22. Microbial Asymmetric Functionalization of β-Cyclocitral-Derived Tetramethyl-Substituted γ-Lactone vol.24, pp.4, 2019, https://doi.org/10.3390/molecules24040666
  23. Loliolide Presents Antiapoptosis and Antiscratching Effects in Human Keratinocytes vol.20, pp.3, 2019, https://doi.org/10.3390/ijms20030651
  24. Phytochemical Investigations of Lonchocarpus Bark Extracts from Monteverde, Costa Rica vol.9, pp.4, 2011, https://doi.org/10.1177/1934578x1400900421
  25. A New Macrolactone, Racemolide Along With Seven Known Compounds With Biological Activities From Mangrove Plant,Lumnitzera racemosa vol.14, pp.6, 2011, https://doi.org/10.1177/1934578x19861255
  26. Monoterpenoid Loliolide Regulates Hair Follicle Inductivity of Human Dermal Papilla Cells by Activating the AKT/β-Catenin Signaling Pathway vol.29, pp.11, 2011, https://doi.org/10.4014/jmb.1908.08018
  27. LEMNA MINOR L. AS A SOURCE OF ANTIOXIDANTS vol.18, pp.1, 2011, https://doi.org/10.15547/tjs.2020.s.01.029
  28. Profiling of antiviral and antioxidant phytochemicals of Pterocephalus frutescens hochist. using high-resolution ultra-performance liquid chromatography/quadrupole time-of-flight mass spectrometer vol.16, pp.71, 2011, https://doi.org/10.4103/pm.pm_558_19
  29. (−)-Loliolide Isolated from Sargassum horneri Protects against Fine Dust-Induced Oxidative Stress in Human Keratinocytes vol.9, pp.6, 2011, https://doi.org/10.3390/antiox9060474
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  32. Antioxidant efficacy of (−)-loliolide isolated from Sargassum horneri against AAPH-induced oxidative damage in Vero cells and zebrafish models in vivo vol.32, pp.5, 2011, https://doi.org/10.1007/s10811-020-02154-9
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  34. Isolation, characterization, in vitro anticancer activity, dft calculations, molecular docking, bioactivity score, drug-likeness and admet studies of eight phytoconstituents from brown alga sargassum vol.1225, pp.None, 2011, https://doi.org/10.1016/j.molstruc.2020.129245
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