Free Radical Scavenging and Ferrous Chelating Activities of Thai Marine Sponge Extracts
Abstract
Twenty-three samples of Thai marine sponges were evaluated for antioxidant activities by comparing the effect of three solvents on the antioxidant activities. Almost of methanolic extracts displayed high DPPH radical scavenging and ferrous chelating activity while methanolic and acetone extracts displayed high ABTS radical scavenging activity. Dichloromethane extracts almost displayed low antioxidant activities. The most significant ABTS and DPPH scavenging activity were determined for the methanolic extract from Hyrtios sp.1 at IC50 value of 77.14 and 228.9 µg/ml, respectively. The dichloromethane extract from Stylissa sp. had the most significant ferrous chelating activity at IC50 value of 159.4 µg/ml. Hyrtios sp.1 had the highest phenol content at the value of 124.27±3.73 mgGAE/g of extract which supposed to perform its radical scavenging activities.Keywords : sponge, free radical scavenging, DPPH, ABTS, ferrous chelatingReferences
Abdillah, S., Nurhayati, A.P.D., Nurhatika, S., Setiawan, E., & Heffen, W.L. (2013). Cytotoxic and antioxidant
activities of marine sponge diversity at Pecaron Bay Pasir Putih Situbondo East Java, Indonesia.
Journal of Pharmacy Research, 6(7), 685-689.
Aktas, N., Genc, Y., Gozcelioglu, B., Konuklugil, B., & Harput, U.S. (2013). Radical scavenging effect of different marine sponges from Mediterranean coasts. Records of Natural Products, 7(2), 96-104.
Chairman, K., Singh, A.R., & Alagumuthu, G. (2012). Cytotoxic and antioxidant activity of selected marine
sponges. Asian Pacific Journal of Tropical Disease, 2(3), 234-238.
Chang, C.C., Yang, M.H., Wen, H.M., & Chern, J.C. (2002). Estimation of total flavonoid content in
propolis by two complementary colorimetric methods. Journal of Food and Drug Analysis, 10, 178-182.
Chatatikun, M., & Chiabchalard, A. (2013). Phytochemical screening and free radical scavenging activities of orange baby carrot and carrot (Daucus carota Linn.) root crude extracts. Journal of Chemical and Pharmaceutical Research, 5(4), 97-102.
Hongpadharakiree, K., Hamin, N., & Sujirachato, P. (2011). Species diversity of marine sponges around Mu
Ko Kra, Nakhon Si Thammarat province, Gulf of Thailand, Thailand. In Proceedings of 49th Kasetsart University Annual Conferences : Fisheries. (pp. 426-435). Bangkok. (in Thai)
Hongpadharakiree, K., & Putchakarn, S. (2013). Species diversity of marine sponges around Mu Ko Surin,
Phangnga province, Thailand. In Proceedings of 51st Kasetsart University Annual Conferences
Verterinary medicine, Fisheries. (pp. 347-356). Bangkok. (in Thai)
Kellogg, J. & Lila, M.A. (2013). Chemical and in vitro assessment of Alaskan coastal vegetation antioxidant
capacity. Journal of Agricultural and Food Chemistry, 61(46), 11025-11032.
Kijjoa, A., Wattanadilok, R., Herz, V., Campos, V., Nascimento, V., & Pinto, M. (2007). Anticancer activity
evaluation of kuanoniamines A and C isolated from the marine sponge Oceanapia sagittaria. collected from the Gulf of Thailand. Marine Drugs, 5(2), 6-22.
Kim, S.K., & Dewapriya, P. (2012). Bioactive compounds from marine sponges and their symbiotic microbes:
a potential source of nutraceuticals. Advances in Food and Nutrition Research, 65, 137-151.
Kobayashi, M., Aoki, S., Sakai, H., Kawazoe, K., Kihara, N., Sasaki, T., & Kitagawa, I. (1993). Altohyrtins B and C and 5-desacetylalthyrtin A, potent cytotoxic macrolide congeners of altohyrtin A, from the Okinawan marine sponge Hyrtios altum. Chemical & Pharmarceutical Bulletin, 41, 989–991.
Longeon, A., Copp, B.R., Quévrain, E., Roué, M., Kientz, B., Cresteil, T., Petek, S., Debitus, C., & Bourguet-Kondracki, M.L. (2011). Bioactive indole derivatives from the South Pacific marine sponges Rhopaloeides odorabile and Hyrtios sp. Marine Drugs, 9(5), 879-888.
Mahidol, C., Prawat, H., Sangpetsiripan, S., & Ruchirawat, S. (2009). Bioactive scalaranes from the Thai
sponge Hyrtios gumminae. Journal of Natural Products, 72(10), 1870–1874.
Mehbub, M.F., Lei, J., Franco, C., & Zhang, W. (2014). Marine sponge derived natural products between
2001 and 2010: Trends and opportunities for discovery of bioactives. Marine drugs, 12(8), 4539-4577.
Nguyen, T., Nguyen, X.C., Longeon, A., Keryhuel, A., Le, M.H., Kim, Y.H., Chau, V.M., & Bourguet- Kondracki, M (2012). Antioxidant benzylidene 2-aminoimidazolones from the Mediteranean sponge
Phorbas toptensi. Tetrahedron, 68(45), 9256-9259.
Nukoolkarn, V.S., Saen-oon, S., Rungrotmongkol, T., Hannongbua, S., Ingkaninan, K., & Suwanborirux, K.
(2008). Petrosamine, a potent anticholinesterase pyridoacridine alkaloid from a Thai marine
sponge Petrosia n. sp. Bioorganic & Medicinal Chemistry, 16(13), 6560-6567.
Papas, A.M. (1999). Antioxidant status, diet, nutrition, and health. CRC Press, Boca Raton.
Pedpradab, P., Molex, W., Nukoolkarn, V.S., & Darumas, U. (2010). Biological activities of extracts from
Andaman Sea sponges, Thailand. European Journal of Biological Sciences, 4, 63-69.
Phuwapraisirisan, P., Matsunaga, S., Fusetani, N., Chaitanawisuti, N., Kritsanapuntu, S., & Menasveta, P.
(2003). Mycaperoxide H, a new cytotoxic norsesterterpene peroxide from a Thai marine sponge Mycale sp. Journal of Natural Products, 66(2), 289–291.
Prawat, H., Mahidol, C., Wittayalai, S., Intachote, P., Kanchanapoom, V., & Ruchirawat, S. (2011).
Nitrogenous sesquiterpenes from the Thai marine sponge Halichondria sp. Tetrahedron, 67(31),
5651-5655.
Qiu, Y., Deng, Z., Pei, Y., Fu, H., Li, J., Proksh, P., & Lin, W. (2004). Sesterterpenoids from the marine sponge
Hyrtios erectus. Journal of Natural Products, 67, 921–924.
Re, R., Pellegrini, N., Proteggente, A., Pannala, A., Yang, M., & Rice-Evans, C. (1999). Antioxidant
activity applying an improved ABTS radical cation decolorization assay. Free Radical Biology and Medicine, 26(9-10), 1231-1237.
Rivera, A.P., & Uy, M.M. (2012). In vitro antioxidant and cytotoxic activities of some marine sponge collected off misamis oriental coast, Philippines. E-Journal of Chemistry, 9(1), 354-358.
Roopesh, J., & Archana, T. (2007). Sponges: an invertebrate of bioactive potential. Current Science, 93, 444-445.
Salmoun, M., Devijver, C., Daloze, D., Braekman, J.C., & van Soest, R.W.M. (2002). 5-Hydroxytryptamine-
derived alkaloids from two marine sponges of the genus Hyrtios. Journal of Natural Products, 65, 1173–1176.
Selvin, J., & Lipton, A.P. (2004). Biopotential of secondary metabolites isolated from marine sponges.
Hydrobiologia, 51, 231-238.
Taheri, A., & Jalalinezhad, V. (2015) Antioxidative and cytotoxic effect of marine sponge (Geodia perarmata)
extracts against breast and colorectal cancer cells. In The 2nd Int'l Conference on Advances in
Environment, Agriculture & Medical Sciences. (pp. 54-57). Antalya, Turkey.
Takamatsu, S., Hodges, T.W., Rajbhandari, I., Gerwick, W.H., Hamann, M.T., & Nagle, D.G. (2003). Marine natural products as novel antioxidant prototypes. Journal of Natural Products, 66(5), 605-608.
Touchstone, J.C., & Dobbins, M.F. (1978). Practice of thin layer chromatography. John Wiley & Sons, Inc., New York.
Utkina, N.K., Makarchenko, A.E., Shchelokova, O.V., & Virovaya, M.V. (2004). Antioxidant activity of phenolic
metabolites from marine sponges. Chemistry of Natural Compounds, 40(4), 373-377.
Utkina, N.K. (2009). Antioxidant activity of aromatic alkaloids from the marine sponges Aaptos aaptos and Hyrtios sp. Chemistry of Natural Compounds., 45(6), 849-853.
Utkina, N.K. (2013). Antioxidant activity of zyzzyanones and makaluvamines from the marine sponge Zyzzya
fuliginosa. Natural Product Communication, 8(11), 1551-1552.
Valko, M., Leibfritz, D., Moncol, J., Cronin, M.T.D., Mazur, M., & Telser, J. (2007). Free radicals and
antioxidants in normal physiological functions and human disease. The International Journal of Biochemistry & Cell biology, 39(1), 44-84.
Wagner, H., & Bladt, S. (1996). Plant drug analysis : a thin layer chromatography atlas, second edition.
Springer-Verlag, Berlin.
Wattanadilok, R., Sawangwong, P., Rodrigues, V., Cidade, V., Pinto, M., Pinto, E., Silva, A., & Kijjoa, A.
(2007). Antifungal activity evaluation of the constituents of Haliclona baeri and Haliclona
cymaeformis, collected from the Gulf of Thailand. Marine Drugs, 5(2), 40–51.
Yamazaki, K., Hashimoto, A., Kokusenya, Y., Miyamoto, T., & Sato, T. (1994). Electrochemical method for
estimating the antioxidative effect of methanol extracts of crude drugs, Chemical and Pharmaceutical Bulletin, 42, 1663-1665.
Youssef, D.T.A., Yamaki, R.K., Kelly, M., & Scheuer, P.J. (2002). Salmahyrtisol A, a novel cytotoxic
sesterterpene from a Red Sea sponge Hyrtios erecta. Journal of Natural Products, 65, 2–6.
Youssef, D.T.A., Shaala, L.A., & Emara, S. (2005). Antimycobacterial scalarane-based sesterterpenes from
the Red Sea sponge Hyrtios erecta. Journal of Natural Products, 68, 1782–1784.
Youssef, D.T.A., Shaala, L.A., & Asfour, H.Z. (2013). Bioactive compounds from the Red Sea marine sponge
Hyrtios species. Marine Drugs, 11(4), 1061–1070.
activities of marine sponge diversity at Pecaron Bay Pasir Putih Situbondo East Java, Indonesia.
Journal of Pharmacy Research, 6(7), 685-689.
Aktas, N., Genc, Y., Gozcelioglu, B., Konuklugil, B., & Harput, U.S. (2013). Radical scavenging effect of different marine sponges from Mediterranean coasts. Records of Natural Products, 7(2), 96-104.
Chairman, K., Singh, A.R., & Alagumuthu, G. (2012). Cytotoxic and antioxidant activity of selected marine
sponges. Asian Pacific Journal of Tropical Disease, 2(3), 234-238.
Chang, C.C., Yang, M.H., Wen, H.M., & Chern, J.C. (2002). Estimation of total flavonoid content in
propolis by two complementary colorimetric methods. Journal of Food and Drug Analysis, 10, 178-182.
Chatatikun, M., & Chiabchalard, A. (2013). Phytochemical screening and free radical scavenging activities of orange baby carrot and carrot (Daucus carota Linn.) root crude extracts. Journal of Chemical and Pharmaceutical Research, 5(4), 97-102.
Hongpadharakiree, K., Hamin, N., & Sujirachato, P. (2011). Species diversity of marine sponges around Mu
Ko Kra, Nakhon Si Thammarat province, Gulf of Thailand, Thailand. In Proceedings of 49th Kasetsart University Annual Conferences : Fisheries. (pp. 426-435). Bangkok. (in Thai)
Hongpadharakiree, K., & Putchakarn, S. (2013). Species diversity of marine sponges around Mu Ko Surin,
Phangnga province, Thailand. In Proceedings of 51st Kasetsart University Annual Conferences
Verterinary medicine, Fisheries. (pp. 347-356). Bangkok. (in Thai)
Kellogg, J. & Lila, M.A. (2013). Chemical and in vitro assessment of Alaskan coastal vegetation antioxidant
capacity. Journal of Agricultural and Food Chemistry, 61(46), 11025-11032.
Kijjoa, A., Wattanadilok, R., Herz, V., Campos, V., Nascimento, V., & Pinto, M. (2007). Anticancer activity
evaluation of kuanoniamines A and C isolated from the marine sponge Oceanapia sagittaria. collected from the Gulf of Thailand. Marine Drugs, 5(2), 6-22.
Kim, S.K., & Dewapriya, P. (2012). Bioactive compounds from marine sponges and their symbiotic microbes:
a potential source of nutraceuticals. Advances in Food and Nutrition Research, 65, 137-151.
Kobayashi, M., Aoki, S., Sakai, H., Kawazoe, K., Kihara, N., Sasaki, T., & Kitagawa, I. (1993). Altohyrtins B and C and 5-desacetylalthyrtin A, potent cytotoxic macrolide congeners of altohyrtin A, from the Okinawan marine sponge Hyrtios altum. Chemical & Pharmarceutical Bulletin, 41, 989–991.
Longeon, A., Copp, B.R., Quévrain, E., Roué, M., Kientz, B., Cresteil, T., Petek, S., Debitus, C., & Bourguet-Kondracki, M.L. (2011). Bioactive indole derivatives from the South Pacific marine sponges Rhopaloeides odorabile and Hyrtios sp. Marine Drugs, 9(5), 879-888.
Mahidol, C., Prawat, H., Sangpetsiripan, S., & Ruchirawat, S. (2009). Bioactive scalaranes from the Thai
sponge Hyrtios gumminae. Journal of Natural Products, 72(10), 1870–1874.
Mehbub, M.F., Lei, J., Franco, C., & Zhang, W. (2014). Marine sponge derived natural products between
2001 and 2010: Trends and opportunities for discovery of bioactives. Marine drugs, 12(8), 4539-4577.
Nguyen, T., Nguyen, X.C., Longeon, A., Keryhuel, A., Le, M.H., Kim, Y.H., Chau, V.M., & Bourguet- Kondracki, M (2012). Antioxidant benzylidene 2-aminoimidazolones from the Mediteranean sponge
Phorbas toptensi. Tetrahedron, 68(45), 9256-9259.
Nukoolkarn, V.S., Saen-oon, S., Rungrotmongkol, T., Hannongbua, S., Ingkaninan, K., & Suwanborirux, K.
(2008). Petrosamine, a potent anticholinesterase pyridoacridine alkaloid from a Thai marine
sponge Petrosia n. sp. Bioorganic & Medicinal Chemistry, 16(13), 6560-6567.
Papas, A.M. (1999). Antioxidant status, diet, nutrition, and health. CRC Press, Boca Raton.
Pedpradab, P., Molex, W., Nukoolkarn, V.S., & Darumas, U. (2010). Biological activities of extracts from
Andaman Sea sponges, Thailand. European Journal of Biological Sciences, 4, 63-69.
Phuwapraisirisan, P., Matsunaga, S., Fusetani, N., Chaitanawisuti, N., Kritsanapuntu, S., & Menasveta, P.
(2003). Mycaperoxide H, a new cytotoxic norsesterterpene peroxide from a Thai marine sponge Mycale sp. Journal of Natural Products, 66(2), 289–291.
Prawat, H., Mahidol, C., Wittayalai, S., Intachote, P., Kanchanapoom, V., & Ruchirawat, S. (2011).
Nitrogenous sesquiterpenes from the Thai marine sponge Halichondria sp. Tetrahedron, 67(31),
5651-5655.
Qiu, Y., Deng, Z., Pei, Y., Fu, H., Li, J., Proksh, P., & Lin, W. (2004). Sesterterpenoids from the marine sponge
Hyrtios erectus. Journal of Natural Products, 67, 921–924.
Re, R., Pellegrini, N., Proteggente, A., Pannala, A., Yang, M., & Rice-Evans, C. (1999). Antioxidant
activity applying an improved ABTS radical cation decolorization assay. Free Radical Biology and Medicine, 26(9-10), 1231-1237.
Rivera, A.P., & Uy, M.M. (2012). In vitro antioxidant and cytotoxic activities of some marine sponge collected off misamis oriental coast, Philippines. E-Journal of Chemistry, 9(1), 354-358.
Roopesh, J., & Archana, T. (2007). Sponges: an invertebrate of bioactive potential. Current Science, 93, 444-445.
Salmoun, M., Devijver, C., Daloze, D., Braekman, J.C., & van Soest, R.W.M. (2002). 5-Hydroxytryptamine-
derived alkaloids from two marine sponges of the genus Hyrtios. Journal of Natural Products, 65, 1173–1176.
Selvin, J., & Lipton, A.P. (2004). Biopotential of secondary metabolites isolated from marine sponges.
Hydrobiologia, 51, 231-238.
Taheri, A., & Jalalinezhad, V. (2015) Antioxidative and cytotoxic effect of marine sponge (Geodia perarmata)
extracts against breast and colorectal cancer cells. In The 2nd Int'l Conference on Advances in
Environment, Agriculture & Medical Sciences. (pp. 54-57). Antalya, Turkey.
Takamatsu, S., Hodges, T.W., Rajbhandari, I., Gerwick, W.H., Hamann, M.T., & Nagle, D.G. (2003). Marine natural products as novel antioxidant prototypes. Journal of Natural Products, 66(5), 605-608.
Touchstone, J.C., & Dobbins, M.F. (1978). Practice of thin layer chromatography. John Wiley & Sons, Inc., New York.
Utkina, N.K., Makarchenko, A.E., Shchelokova, O.V., & Virovaya, M.V. (2004). Antioxidant activity of phenolic
metabolites from marine sponges. Chemistry of Natural Compounds, 40(4), 373-377.
Utkina, N.K. (2009). Antioxidant activity of aromatic alkaloids from the marine sponges Aaptos aaptos and Hyrtios sp. Chemistry of Natural Compounds., 45(6), 849-853.
Utkina, N.K. (2013). Antioxidant activity of zyzzyanones and makaluvamines from the marine sponge Zyzzya
fuliginosa. Natural Product Communication, 8(11), 1551-1552.
Valko, M., Leibfritz, D., Moncol, J., Cronin, M.T.D., Mazur, M., & Telser, J. (2007). Free radicals and
antioxidants in normal physiological functions and human disease. The International Journal of Biochemistry & Cell biology, 39(1), 44-84.
Wagner, H., & Bladt, S. (1996). Plant drug analysis : a thin layer chromatography atlas, second edition.
Springer-Verlag, Berlin.
Wattanadilok, R., Sawangwong, P., Rodrigues, V., Cidade, V., Pinto, M., Pinto, E., Silva, A., & Kijjoa, A.
(2007). Antifungal activity evaluation of the constituents of Haliclona baeri and Haliclona
cymaeformis, collected from the Gulf of Thailand. Marine Drugs, 5(2), 40–51.
Yamazaki, K., Hashimoto, A., Kokusenya, Y., Miyamoto, T., & Sato, T. (1994). Electrochemical method for
estimating the antioxidative effect of methanol extracts of crude drugs, Chemical and Pharmaceutical Bulletin, 42, 1663-1665.
Youssef, D.T.A., Yamaki, R.K., Kelly, M., & Scheuer, P.J. (2002). Salmahyrtisol A, a novel cytotoxic
sesterterpene from a Red Sea sponge Hyrtios erecta. Journal of Natural Products, 65, 2–6.
Youssef, D.T.A., Shaala, L.A., & Emara, S. (2005). Antimycobacterial scalarane-based sesterterpenes from
the Red Sea sponge Hyrtios erecta. Journal of Natural Products, 68, 1782–1784.
Youssef, D.T.A., Shaala, L.A., & Asfour, H.Z. (2013). Bioactive compounds from the Red Sea marine sponge
Hyrtios species. Marine Drugs, 11(4), 1061–1070.
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2016-06-30
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บทความวิจัยจากการสัมมนาและฝึกอบรมนานาชาติ International Seminar and Workshop on Marine Natural Products 2015
