应用天然产物 ›› 2015, Vol. 5 ›› Issue (5): 223-235.DOI: 10.1007/s13659-015-0068-0
• Original article • 下一篇
Marie Pascaline Rahelivao1, Margit Gruner1, Hanta Andriamanantoanina2, Ingmar Bauer1, Hans-Joachim Knölker1
收稿日期:
2015-08-05
修回日期:
2015-08-18
出版日期:
2015-10-24
发布日期:
2018-02-11
通讯作者:
Hans-Joachim Knölker,e-mail:hans-joachim.knoelker@tu-dresden.de
Marie Pascaline Rahelivao1, Margit Gruner1, Hanta Andriamanantoanina2, Ingmar Bauer1, Hans-Joachim Knölker1
Received:
2015-08-05
Revised:
2015-08-18
Online:
2015-10-24
Published:
2018-02-11
摘要: Eight species of brown algae(Phaeophyceae) from the coast of Madagascar have been investigated for their chemical constituents. Fucosterol(3) was obtained as the most abundant compound. The brown alga Sargassum ilicifolium was the source for the first isolation of the terpenoid C27-alcohol 1, 1', 2-trinorsqualenol(1) from marine sources. From S. incisifolium we isolated the highly unsaturated glycolipid 1-O-palmitoyl-2-O-stearidonoyl-3-O-β-D-galactopyranosylglycerol(4) and we report the first full assignment of its 1H and 13C NMR data. Apo-9'-fucoxanthinone(8) along with 24-ketocholesterol(5),(22E)-3β-hydroxycholesta-5, 22-dien-24-one(6), and saringosterol(7) were obtained from Turbinaria ornata. The crude extracts of all eight species of brown algae exhibited a pronounced antimicrobial activity against the Gram-positive bacteria Bacillus cereus, Staphylococcus aureus, and Streptococcus pneumoniae.
Marie Pascaline Rahelivao, Margit Gruner, Hanta Andriamanantoanina, Ingmar Bauer, Hans-Joachim Knölker. Brown Algae(Phaeophyceae) from the Coast of Madagascar:preliminary Bioactivity Studies and Isolation of Natural Products[J]. 应用天然产物, 2015, 5(5): 223-235.
Marie Pascaline Rahelivao, Margit Gruner, Hanta Andriamanantoanina, Ingmar Bauer, Hans-Joachim Knölker. Brown Algae(Phaeophyceae) from the Coast of Madagascar:preliminary Bioactivity Studies and Isolation of Natural Products[J]. Natural Products and Bioprospecting, 2015, 5(5): 223-235.
1. D.J. Faulkner, Nat. Prod. Rep. 19, 1-49 (2002) 2. A.J. Smit, J. Appl. Phycol. 16, 245-262 (2004) 3. R.K. Jha, X. Zi-rong, Mar. Drugs 2, 123-146 (2004) 4. K.H.M. Cardozo, T. Guaratini, M.P. Barros, V.R. Falcao, A.P. Tonon, N.P. Lopes, S. Campos, M.A. Torres, A.O. Souza, P. Colepicolo, E. Pinto, Comp. Biochem. Physiol. C:Toxicol Pharmacol. 146, 60-78 (2007) 5. L. O'Sullivan, B. Murphy, P. McLoughlin, P. Duggan, P.G. Lawlor, H. Hughes, G.E. Gardiner, Mar. Drugs 8, 2038-2064 (2010) 6. A.A. El Gamal, Saudi Pharm. J. 18, 1-25 (2010) 7. N. Sithranga Boopathy, K. Kathiresan, J. Oncol. 2010 (2010), Article ID 214186, doi:10.1155/2010/214186 8. C.L.F. de Almeida, H.S. de Falcao, G.R.M. de Lima, C.A. de Montenegro, N.S. Lira, P.F. de Athayde-Filho, L.C. Rodrigues, M.D.F.V. de Souza, J.M. Barbosa-Filho, L.M. Batista, Int. J. Mol. Sci. 12, 4550-4573 (2011) 9. M.P. Rahelivao, M. Gruner, H. Andriamanantoanina, B. Andriamihaja, I. Bauer, H.-J. Knolker, Mar. Drugs 13, 4197-4216 (2015) 10. H. Andriamanantoanina, M. Rinaudo, Polym. Int. 59, 1531-1541 (2010) 11. H. Andriamanantoanina, M. Rinaudo, Carbohydr. Polym. 82, 555-560 (2010) 12. M.P. Rahelivao, H. Andriamanantoanina, A. Heyraud, M. Rinaudo, Food Hydrocoll. 32, 143-146 (2013) 13. P.W. Carter, I.M. Heilbron, B. Lythgoe, Proc. R. Soc. London. Ser. B 128, 82-109 (1939) 14. G.W. Patterson, Lipids 6, 120-127 (1971) 15. F. Bekkara-Aounallah, R. Gref, M. Othman, L.H. Reddy, B. Pili, V. Allain, C. Bourgaux, H. Hillaireau, S. Lepêtre-Mouelhi, D. Desmaële, J. Nicolas, N. Chafi, P. Couvreur, Adv. Funct. Mater. 18, 3715-3725 (2008) 16. S.E. Sen, G.D. Prestwich, J. Am. Chem. Soc. 111, 1508-1510 (1989) 17. E.J. Corey, K. Lin, M. Jautelat, J. Am. Chem. Soc. 90, 2724-2726 (1968) 18. I. Abe, Y. Kashiwagi, H. Noguchi, Bioorg. Med. Chem. Lett. 10, 2525-2528 (2000) 19. G. Grosa, F. Viola, M. Ceruti, P. Brusa, L. Delprino, F. Dosio, L. Cattel, Eur. J. Med. Chem. 29, 17-23 (1994) 20. Y.C. Hu, M.Y. Li, Zhongguo Tiaoweipin 35, 93-116 (2010) 21. C.A.N. Catalan, W.C.M.C. Kokke, C. Duque, C. Djerassi, J. Org. Chem. 48, 5207-5214 (1983) 22. J.X. Liu, D.-L. Di, Y.-P. Shi, J. Chin. Chem. Soc. 55, 863-870 (2008) 23. Y. Fujimoto, M. Morisaki, N. Ikekawa, J. Chem. Soc. Perkin Trans. 1, 2302-2307 (1975) 24. L.M. Zeng, Z. Zeng, J.Y. Su, Chem. Res. Chin. Univ. 11, 174-177 (1995) 25. W.F. He, L.G. Yao, H.L. Liu, Y.W. Guo, J. Asian Nat. Prod. Res. 16, 685-689 (2014) 26. G. Marcolongo, F. de Appolonia, A. Venzo, C.P. Berrie, T. Carofiglio, C. Ceschi Berrini, Nat. Prod. Res. 20, 766-774 (2006) 27. H.O. Kalinowski, S. Berger, S. Braun, 13C-NMR-Spektroskopie (Georg Thieme, Stuttgart, 1984) 28. M. Kates, in Advances in lipid research, vol. 8, ed. by P. Rodolfo, K. David (Academic Press, New York, 1970), pp. 225-265 29. N. Murata, P.A. Siegenthaler, in Lipids in Photosynthesis:Structure, Function and Genetics, ed. by P.A. Siegenthaler, N. Murata (Kluwer, Dordrecht, 1998), pp. 1-20 30. H. Wada, N. Murata, Lipids in photosynthesis:essential and regulatory functions (Springer, Dordrecht, 2009) 31. S. Amara, N. Barouh, J. Lecomte, D. Lafont, S. Robert, P. Villeneuve, A. de Caro, F. Carrière, Biochim. Biophys. Acta 1801, 508-516 (2010) 32. Y.H. Kim, E.H. Kim, C. Lee, M.H. Kim, J.R. Rho, Lipids 42, 395-399 (2007) 33. A.C. Ma, Z. Chen, T. Wang, N. Song, Q. Yan, Y.C. Fang, H.S. Guan, H.B. Liu, J. Agric. Food Chem. 62, 11157-11162 (2014) 34. V. Reshef, E. Mizrachi, T. Maretzki, C. Silberstein, S. Loya, A. Hizi, S. Carmeli, J. Nat. Prod. 60, 1251-1260 (1997) 35. A. Bruno, C. Rossi, G. Marcolongo, A. Di Lena, A. Venzo, C.P. Berrie, D. Corda, Eur. J. Pharmacol. 524, 159-168 (2005) 36. M. Lenti, C. Gentili, A. Pianezzi, G. Marcolongo, A. Lalli, R. Cancedda, F.D. Cancedda, Nat. Prod. Res. 23, 754-762 (2009) 37. V. Ulivi, M. Lenti, C. Gentili, G. Marcolongo, R. Cancedda, F. Descalzi Cancedda, Arthrit. Res. Ther. 13, R92 (2011) 38. B. Riegel, I.A. Kaye, J. Am. Chem. Soc. 66, 723-724 (1944) 39. A.M. Motzfeldt, Acta Chem. Scand. 24, 1846-1847 (1970) 40. P. Koch, C. Djerassi, V. Lakshmi, F.J. Schmitz, Helv. Chim. Acta 66, 2431-2436 (1983) 41. P. Koch, Y. Nakatani, B. Luu, G. Ourisson, Bull. Soc. Chim. Fr. 189-194 (1983) 42. N. Ikekawa, K. Tsuda, N. Morisaki, Chem. Ind. (London) 1179-1180 (1966) 43. N. Ikekawa, N. Morisaki, K. Tsuda, T. Yoshida, Steroids 12, 41-48 (1968) 44. W. Sucrow, B. Radüchel, Chem. Ber. 103, 2711-2717 (1970) 45. S.E.N. Ayyad, S.Z.A. Sowellim, M.S. El-Hosini, A. Abo-Atia, Z. Naturforsch. 58c, 333-336 (2003) 46. A. Jensen, Acta Chem. Scand. 18, 2005-2007 (1964) 47. Y. Doi, M. Ishibashi, N. Yamaguchi, J. Kobayashi, J. Nat. Prod. 58, 1097-1099 (1995) 48. S. Ogawa, G. Kakiyama, A. Muto, A. Hosoda, K. Mitamura, S. Ikegawa, A.F. Hofmann, T. Iida, Steroids 74, 81-87 (2009) 49. F. de Riccardis, L. Minale, M. Iorizzi, C. Debitus, C. Lévi, J. Nat. Prod. 56, 282-287 (1993) 50. Z.H. Wu, T. Liu, C.X. Gu, C.L. Shao, J. Zhou, C.Y. Wang, Chem. Nat. Compd. 48, 158-160 (2012) 51. K. Tsuda, R. Hayatsu, Y. Kishida, S. Akagi, J. Am. Chem. Soc. 80, 921-925 (1958) 52. J.D. Newburger, J.J. Uebel, M. Ikawa, K.K. Andersen, R.B. Gagosian, Phytochemistry 18, 2042-2043 (1979) 53. T. Milkova, G. Talev, R. Christov, S. Dimitrova-Konaklieva, S. Popov, Phytochemistry 45, 93-95 (1997) 54. S. Hoet, L. Pieters, G.G. Muccioli, J.-L. Habib-Jiwan, F.R. Opperdoes, J. Quetin-Leclercq, J. Nat. Prod. 70, 1360-1363 (2007) 55. Z. Chen, J. Liu, Z. Fu, C. Ye, R. Zhang, Y. Song, Y. Zhang, H. Li, H. Ying, H. Liu, J. Agric. Food Chem. 62, 6130-6137 (2014) 56. G.A. Wachter, S.G. Franzblau, G. Montenegro, J.J. Hoffmann, W.M. Maiese, B.N. Timmermann, J. Nat. Prod. 64, 1463-1464 (2001) 57. R. Bonnett, A.K. Mallams, A.A. Spark, J.L. Tee, B.C.L. Weedon, A. McCormick, J. Chem. Soc. C 3, 429-454 (1969) 58. J.R. Hlubucek, J. Hora, S.W. Russell, T.P. Toube, B.C.L. Weedon, J. Chem. Soc. Perkin Trans. 1, 848-852 (1974) 59. K. Mori, T. Ooi, M. Hiraoka, N. Oka, H. Hamada, M. Tamura, T., Kusumi, Mar. Drugs 2, 63-72 (2004) 60. K.E. Park, Y.A. Kim, H.A. Jung, H.J. Lee, J.W. Ahn, B.J. Lee, Y. Seo, J. Korean Chem. Soc. 48, 394-398 (2004) 61. M. El Hattab, G. Culioli, R. Valls, M. Richou, L. Piovetti, Biochem. Syst. Ecol. 36, 447-451 (2008) 62. S.S. Kumar, Y. Kumar, M.S.Y. Khan, V. Gupta, E. De Clercq, Iran. J. Pharm. Res. 9, 411-416 (2010) 63. R.K. Sharma, Bioorg. Chem. 21, 49-60 (1993) 64. S. Lee, Y.S. Lee, S.H. Jung, S.S. Kang, K.H. Shin, Arch. Pharm. Res. 26, 719-722 (2003) 65. S.S. Kumar, Y. Kumar, M.S.Y. Khan, J. Anbu, E. De Clercq, Pharmacologyonline 1, 1104-1112 (2009) 66. T. Hashimoto, M. Tori, Y. Asakawa, Phytochemistry 30, 2927-2931 (1991) 67. H. Zhang, X. Xiao, M.M. Conte, Z. Khalil, R.J. Capon, Org. Biomol. Chem. 10, 9671-9676 (2012) 68. A. Baumeler, W. Brade, A. Haag, C.H. Eugster, Helv. Chim. Acta 73, 700-715 (1990) 69. P.B. Shinde, M.A. Kim, B.W. Son, C.O. Lee, J.H. Jung, Nat. Prod. Sci. 13, 365-368 (2007) 70. Y. Corbett, L. Herrera, J. Gonzalez, L. Cubilla, T.L. Capson, P.D. Coley, T.A. Kursar, L.I. Romero, E. Ortega-Barria, Am. J. Trop. Med. Hyg. 70, 119-124 (2004) |
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