ENDOGENIC LOLIOLIDE, PHENYLETHYLAMINE AND EXOGENICCOMPOUNDS IN MARINE ALGAE

Endogenic loliolide, phenylethylamine and exogeniccompounds in marine algae

Kasım Cemal Güven, Burak Coban, Sumru Özkırımlı, Huseyin Erdugan, Ekrem Sezik

Turkish Marine Research Foundation (TUDAV),Beykoz, Istanbul, TURKEY
Faculty of Science and Letters,Department of Chemistry, Bulent Ecevit University, 67100, Zonguldak, TURKEY
Faculty of Pharmacy, Department of Pharmaceutical Chemistry, Istanbul University, Istanbul, TURKEY and Faculty of Pharmacy, University of Yeniyuzyil, Istanbul, TURKEY
Department of Biology, Faculty of Science, 18 Mart University, Çanakkale, TURKEY
Department of Pharmacognosy, Faculty of Pharmacy, Gazi University, Ankara, TURKEY

Abstract

Endogenic compound loliolide in marine algae Laurencia obtusa var. pyramidata, Chondria capillaris, Ceramium rubrum, Cystaseira barbata, Ulva rigida, and Ulva intestinalis and phenylethylamine in Chondria capillaris were found. Exogenic compounds were mainly petroleum components and phthalate derivatives. These findings are reported for the first time for the examined algae. These algae are eaten in some eastern Asian countries but its human consumption is not recommended because they potentially absorb many pollutants from the aquatic environment.

Keywords: Algae, loliolide, phenylethylamine, exogenic, GC-MS

References

Ali, M.S., Pervez, M.K., Saleem, M., Ahmed, F. (2003) Dichotenone-A and –B: two enones from the marine brown alga Dictyota dichotoma (Hudson) Lamour. Nat. Prod. Res. 17: 301-306.

Attaurrahman, S.Z., Choudhary, M.I., Abbas, S.A., Shameel, M. (1991) Stockerine – a novel linear metabolite from Stockeyia indica. Fitoterapia 62: 77- 80.

Crotti, A.E.M., Fonseca, T., Hong, H., Staunton, J., Galembeck, S.E., Lopes, N., Gates, P.J. (2004) The fragmentation mechanism of five-membered lactones by electrospray ionisation tandem mass spectrometry. Int. J. Mass Spect. 232: 271- 276.

Duan, H., Takaishi, Y., Momota, H., Ohmoto, Y., Taki, T. (2002) Immunosuppressive constituents from Saussurea medusa. Phytochem. 59: 85- 90.

El Hattab, M., Culioli, G., Valls, R., Richou, M., Piovetti, L. (2008) Apofucoxanthinoids and loliolide from the brown alga Cladostephus spongiosus f. verticillatus (Heterokonta, Sphacelariales). Biochem. Syst. Ecol. 36: 447-451.

George, M. (1961) Oil pollution in marine organisms. Nature 192:1209.

Guven, K.C., Nesimigil, F., Cumalı, S. (2009) Oil pollution in the Black Sea marine organisms during 2003-2006: mussel, shellfish and algae. J. Black Sea/Mediterranean Environ. 15: 165-178.

Hiraga, Y., Taino, K., Kurokawa, M., Takagi, R., Ohkata, K. (1997) (-)-Loliolide and other germination inhibitory active constituents in Equisetum arvense. Nat. Prod. Letters 10: 181-186.

Ishiwatari, S., Ono, T. (2008) Melanogenesis inhibitor. Jpn. Kokai Tokkyo Koho. (Accessed in May 2015, http://www.j-tokkyo.com/2008/A61K/JP2008- 056616.shtml). (In Japanese).

Kato, T., Imai, T., Kashimura, K., Saito, N., Masaya, K. (2003) Germination response in wheat grains to dihydroactinidiolide, a germination inhibitor in wheat husks, and related compounds. J. Agric. Food Chem. 51: 2161-2167.

Khan, A.M., Noreen, S., Imran, Z.P., Rahman, A., Choudhary, M.I. (2011) A new compound, jolynamine, from marine brown alga Jolyna laminarioides. Nat. Prod. Res. 25: 898.

Kimura, J., Maki, N. (2002) New loliolide derivatives from the brown alga Undaria pinnatifida. J. Nat. Prod. 6: 57-58.

Klock, F., Baas, M., Cox, H.C., DeLeeaw, F.W., Scheuk, P.A. (1984) Loliolides and dihydroactinidiolide in recent marine sediment probably indicate a major transformation pathway of carotenoids. Tet. Lett. 25: 5577-5580.

Kuniyoshi, M. (1985) Germination inhibitors from the brown alga Sargassum crassifolium (Phacophyta, Sargassaceae). Bot. Mar. 28: 501-503.

Liu, S.Q., Pezzuto, J.M., Kinghorn, A.D. (1988) Additional biologically active constituents of the Chinese tallow tree (Sapium sebiferum). J. Nat. Prod. 51: 619-620.

Lu, H., Xie, H., Gong, Y., Wang, Q., Yang, Y. (2011) Secondary metabolites from the seaweed Gracilaria lemaneiformis and their allelopathic effects on Skeletonema costatum. Biochem. Syst. Ecol. 39: 397-400.

Okada, N., Shirata, K., Niwano, M., Koshino, H., Uramoto, M. (1994) Immunosuppressive activity of a monoterpene from Eucommia ulmoides. Phytochem. 37: 281-282.

Okunade, L., Wiemer, D.F. (1985) (-)-Loliolide, an ant-repellent compound from Xanthoxyllum setulosum. J. Nat. Prod. 48: 472-473.

Parameswaran, P.S., Naik, C.G., Das, B., Kamat, S.Y., Bose, A.K., Nair, M.S.R. (1996) Constituents of the brown alga Padina tetrastromatica (Hauck)-II. Ind. J. Chem. Sec. B. 35B: 463-467.

Park, K.E., Kim, Y.A., Jung, H.A. Lee, H.J. Ahn, J.W., Lee, B.J., Seo, Y. (2004) Three norisoprenoids from the brown alga Sargassum thunbergii. J. Korean Chem. Soc. 48: 394-400.

Percot, A., Yalcin, A., Aysel, V., Erdugan, H., Dural, B., Guven, K.C. (2009a) Alkaloids in marine algae. Nat. Prod. Res. 23: 460-465.

Percot, A., Yalcin, A., Aysel, V., Erdugan, H., Durel, B., Guven, K.C. (2009b) Phenylethylamine content in marine alga around Turkish coast. Bot. Mar. 52: 87-90.

Qin, M., Li, X., Yin, S., Wang, C., Wang, B. (2007) Chemical constituents from Sargassum thunbergii. Haiyang Kexue (Marine Sciences) 31: 47-50.

Ragasa, C Y., DeLuna, R.D., Hofilena, J.G. (2005) Antimicrobial terpenoids from Pterocarpus indicus. Nat. Prod. Res. 19: 305-309.

Rao, B.CH., Pullaiah, K.CH. (1980) Chemical examination of marine algae off Visakhapatnam Coast: Part II – Constituents of Padina tetrastromatica Hauck. Ind. J. Chem. 21B: 605-606.

Rasher, D.B., Stout, E.P., Engel, S., Kubanek, J., Hay, M.E. (2011) Macroalgal terpenes function as allelopathic agents against reef corals. Proc. Nat. Acad. Sci. 108: 17726-17731.

Ravi, B.N. Murphy, P.T. Lidgard, R.O. Warren, R.G., Wells, R.J. (1982) C18 terpenoid metabolites of the brown alga Cystophora moniliformis. Aust. J. Chem. 35: 171-182.

Rocha, O.P., DeFelicio, R., Rodrigues, A.H.B., Ambrosio, D.L., Cicarelli, R.M.B., DeAlbuquerque, S., Young, M.C.M., Yokoya, N.S., Debonsi, H.M. (2011) Chemical profile and biological potential of non-polar fractions from Centroceras clavulatum (C. Agardh) Montagne (Ceramiales, Rhodophyta). Molecules 16: 7105-7114.

Sabelli, H., Fink, P., Fawceit, F., Tom, C. (1996) Sustained effect of PEA replacement. J. Neuropsyc 8: 168-171.

Shah, Z. (1990) Studies on the Chemical Constituents of Stokeyia indica, Ervatamia coronaria and Caplophyllum Species. PhD Thesis, H.E.J Research Institute of Chemistry, University of Karachi.

Shaikh, W. (1993) Taxanomic and Phycochemical Studies of Certain Brown Algae from the Coast of Karachi. PhD Thesis, Department of Botany, University of Karachi.

Shi, D.Y., Han, L.J., Sun, J., Yang, Y.C., Shi, J.G., Fun, X. (2005) Studies on chemical constitutes of green alga Chaetomorpha basiretorsa and their bioactivity. Zhongguo Zhongyao Zazhi 30: 1162-1165.

Smith, T.A. (1977) Phenylethylamine and related compounds in plants. Phytochem. 16: 9-18.

Steiner, M., Hartmann, T. (1968) The occurrence and distribution of volatile amines in marine algae. Planta 79: 113–121.

Takemoto, T., Takeshita, Y. (1970) Studies on the constituents of Undaria pinnatifida. I: methanol soluble constituents. J. Pharm. Soc. Japan 90: 1057- 1060.

Xian, Q., Chen, H., Liu, H., Zou, H., Yin, D. (2006) Isolation and identification of antialgal compounds from the leaves of Vallisneria spiralis L. by activityguided fractionation. Environ. Sci. Pollut. Res. 13: 233-237.

Yang, X., Kang, M.C., Lee, K.W., Kang, S.M., Leo, W.W., Jean, Y.J. (2011) Antioxidant activity and cell protective effect of loliolide isolated from Sargassum ringgoldianum Subsp. coreanum. Algae 26: 201-208.

Yuan, Z.H., Han, L.J., Fan, X., Li, S., Shi, D.Y., Sun, J., Ma, M., Yang, Y.C., Shi, J.G. (2006) Chemical constituents from red alga Corallina pilulifera. Zhongguo Zhongyao Zazhi 31: 1787-1790.