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Vol. 27 No. 6 (2015): Vol 27 Issue 6

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Potent Antifouling Metabolites from Red Sea Organisms

https://doi.org/10.14233/ajchem.2015.18701
Sultan S. Al-Lihaibi
Department of Marine Chemistry, Faculty of Marine Sciences, King Abdulaziz University, P.O. Box 80207, Jeddah 21589, Saudi Arabia
Ahmed Abdel-Lateff
Department of Natural Products and Alternative Medicine, Faculty of Pharmacy, King Abdulaziz University, Jeddah 21589, P.O. Box 80260, Saudi Arabia; Department of Pharmacognosy, Faculty of Pharmacy, Minia University, Minia 61519, Egypt
Walied M. Alarif
Department of Marine Chemistry, Faculty of Marine Sciences, King Abdulaziz University, P.O. Box 80207, Jeddah 21589, Saudi Arabia
Yasuyuki Nogata
Central Research Institute of Electric Power Industry, Abiko, Japan
Seif-Eldin N. Ayyad
Department of Chemistry, Faculty of Science, King Abdulaziz University, P.O. Box 80203, Jeddah 21589, Saudi Arabia
Tatsufumi Okino
Faculty of Environmental Earth Science, Hokkaido University, Sapporo 060-0810, Japan

Corresponding Author(s) : Sultan S. Al-Lihaibi

sallihaibi@kau.edu.sa

Asian Journal of Chemistry, Vol. 27 No. 6 (2015): Vol 27 Issue 6

Abstract

Forty two marine macro-organisms include; algae, corals and sponges were collected from the Saudi Red Sea territorial water. The methanolic extracts of all the samples were evaluated towards their antifouling effects cyprid larvae of Balanus amphitrite. Fifteen crude extracts showed antifouling activity at 10 μg/mL, eleven of which considered to be promising for isolation targets from the results of low mortality. Two marine species of sponge Siphonochalina siphonella and red alga Laurencia obtusa were selected further chemical investigation.The extract of S. siphonella, was partially fractionated and led to isolation of two known triterpenoidal metabolites; sipholenol A (1) and sipholenone A (2). Three compounds; 2,10-dibromo-3-chloro-7-chamigrene (3) and 12-hydroxyisolaurene (4) and (12E)-cis-maneonene-E (5), were isolated from L. obtusa. All the compounds (1-5) were evaluated for their antifouling activities. Compounds 1, 3 and 4 showed potent effects with 48 h EC50, 0.2, 0.14 and 1.34 μg/mL, respectively. Compounds 1 and 3 were more potent than the positive control CuSO4 (EC50 = 0.34 μg/mL), while compound 2 showed moderate activity at 10 μg/mL.

Keywords

Red Sea Antifoulants Algae Soft corals Sponge Siphonochalina siphonella Laurencia obtusa
S. Al-Lihaibi, S., Abdel-Lateff, A., M. Alarif, W., Nogata, Y., N. Ayyad, S.-E., & Okino, T. (2015). Potent Antifouling Metabolites from Red Sea Organisms. Asian Journal of Chemistry, 27(6), 2252–2256. https://doi.org/10.14233/ajchem.2015.18701
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References
  1. E. Ralston and G. Swain, Bioinspir. Biomim., 4, 015007 (2009); doi:10.1088/1748-3182/4/1/015007.
  2. M. Wahl, Biofouling, 24, 427 (2008); doi:10.1080/08927010802339772.
  3. A. Turner, N. Singh and J.P. Richards, Environ. Pollut., 157, 1526 (2009); doi:10.1016/j.envpol.2009.01.008.
  4. Z.J. Mudryk, Pol. J. Environ. Stud., 11, 401 (2002).
  5. J.F. Schumacher, N. Aldred, M.E. Callow, J.A. Finlay, J.A. Callow, A.S. Clare and A.B. Brennan, Biofouling, 23, 307 (2007); doi:10.1080/08927010701393276.
  6. C.D. Amsler, Algal Chemical Ecology, Springer-Verlag: Berlin, Germany; edn 2, pp. 314 (2009).
  7. E. Marris, Nature, 443, 904 (2006); doi:10.1038/443904a.
  8. C. Hellio, J.-P. Maréchal, B.A.P. Da Gama, R.C. Pereira and A.S. Clare, in eds.: C. Hellio and D.M.Y. Yebra, Natural Marine Products with Antifouling Activities, In: Advances in Marine Antifouling Coatings and Technologies, Woodshead Publishing: Cambridge, UK, pp. 572-622 (2009).
  9. G.M. Konig and A.D. Wright, J. Nat. Prod., 60, 967 (1997); doi:10.1021/np970181r.
  10. C.S. Vairappan, M. Daitoh, M. Suzuki, T. Abe and M. Masuda, Phytochemistry, 58, 291 (2001); doi:10.1016/S0031-9422(01)00243-6.
  11. V.P.L. Mol, T.V. Raveendran and P.S. Parameswaran, Int. Biodeterior. Biodegrad., 63, 67 (2009); doi:10.1016/j.ibiod.2008.07.001.
  12. M. Daoudi, S. Bakkas, G. Culioli, A. Ortalo-Magné, L. Piovetti and M.D. Guiry, Biochem. Syst. Ecol., 29, 973 (2001); doi:10.1016/S0305-1978(01)00030-8.
  13. N. Fusetani, Nat. Prod. Rep., 21, 94 (2004); doi:10.1039/b302231p.
  14. U. Shmueli, S. Carmely, A. Groweiss and Y. Kashman, Tetrahedron Lett., 22, 709 (1981); doi:10.1016/S0040-4039(01)92531-6.
  15. B.M. Howard and W. Fenical, Tetrahedron Lett., 16, 1687 (1975);
  16. doi:10.1016/S0040-4039(00)72233-7.
  17. W.M. Alarif, S.S. Al-Lihaibi, S.-E.N. Ayyad, M.H. Abdel-Rhman and F.B. Badria, Eur. J. Med. Chem., 55, 462 (2012); doi:10.1016/j.ejmech.2012.06.060.
  18. S.Z. Abou-Elnaga, W.M. Alarif and S.S. Al-Lihaibi, Clean – Soil, Air Water, 39, 787 (2011); doi:10.1002/clen.201000597.
  19. Z. Xi, W. Bie, W. Chen, D. Liu, L. Ofwegen, P. Proksch and W. Lin, Mar. Drugs, 11, 3186 (2013); doi:10.3390/md11093186.
  20. R. Duffy, C. Wade and R. Chang, Drug Discov. Today, 17, 942 (2012); doi:10.1016/j.drudis.2012.03.013.
  21. M.-E.F. Hegazy, A.M.G. Eldeen, A.A. Shahat, F.F. Abdel-Latif, T.A. Mohamed, B.R. Whittlesey and P.W. Paré, Mar. Drugs, 10, 209 (2012); doi:10.3390/md10010209.
  22. G.R. Pettit, R. Tan and Z.A. Cichacz, J. Nat. Prod., 68, 1253 (2005); doi:10.1021/np0402221.
  23. M. Salmoun, C. Devijver, D. Daloze, J.-C. Braekman, R. Gomez, M. de Kluijver and R.W.M. Van Soest, J. Nat. Prod., 63, 452 (2000); doi:10.1021/np9903346.
  24. P. Sauleau, M. Martin, M.T.H. Dau, D.T.A. Youssef and M. Bourguet-Kondracki, J. Nat. Prod., 69, 1676 (2006); doi:10.1021/np060132r.
  25. F.R. Angawi, E. Saqur, A. Abdel-Lateff, F.A. Badria and S.N. Ayyad, Pharm. Mag., 38, 334 (2014).
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