Antibacterial compound from the endophytic fungus Phomopsis longicolla isolated from the tropical red seaweed Bostrychia radicans

Botanica Marina

Volumn 55, Issue 4, 2012, Pages 435-440

  Erbert, Cíntia ^a   Lopes, Adriana A ^a   Yokoya, Nair S ^b   Furtado, Niege A J C ^a   Conti, Raphael ^a   Pupo, Mônica T ^a   Lopes, João Luis C ^a   Debonsi, Hosana M ^a  

^a UNIVERSITY OF SÃO PAULO   (Brazil)

^b Instituto de Pesquisas Ambientais do Estado de São Paulo   (Brazil)

Author keywords

Antibacterial activity; Bostrychia radicans; Endophytic fungi; Marine algae; Phomopsis longicolla

Indexed keywords

ALGA; ANTIBIOTICS; ANTIMICROBIAL ACTIVITY; ENDOPHYTE; FUNGUS; INHIBITOR; INTERSPECIFIC INTERACTION; MARINE ENVIRONMENT; METABOLITE; SEAWEED; SPECIES DIVERSITY; TROPICAL ENVIRONMENT;

EID: 84867759344     PISSN: 00068055     EISSN: 14374323     Source Type: Journal    
DOI: 10.1515/bot-2011-0023     Document Type: Article

References (36)

1. Blunt, J.W., B.R. Copp, W.P. Hu, M.H.G. Munro, P.T. Northcote and M.R. Prinsep. 2009. Marine natural products. Nat. Prod. Rep. 26: 170-244.
2. Borges, W.S., K.B. Borges, P.S. Bonato, S. Said and M.T. Pupo. 2009. Endophytic fungi: natural products, enzymes and biotransformation reactions. Curr. Org. Chem. 13: 1137-1163.
3. Christian, O.E., J. Compton, K.R. Christian, S.L. Mooberry, F.A. Valeriote and P. Crews. 2005. Using jasplakinolide to turn on pathways that enable the isolation of new chaetoglobosins from Phomopsis asparagi. J. Nat. Prod. 68: 1592-1597.
4. Dai, J., K. Krohn, U. Floerke, D. Gehle, H.J. Aust, S. Draeger, B. Schulz and J. Rheinheimer. 2005. Novel highly substituted biraryl ethers, phomosines D-G, isolated from the endophytic fungus Phomopsis sp. from Adenocarpus foliolosus. Eur. J. Org. Chem. 23: 5100-5105.
5. De Vita-Marques, A.M., S.P. Lira, R.G.S. Berlinck, M.H.R. Seleghim, S.R.P. Sponchiado, S.M. Tauk-Tornisielo, M. Barata, M. Pessoa, M.O. Moraes, B.C. Cavalcanti, G.G.F. Nascimento, O. Souza, F.C.S. Galetti, C.L. Silva, M. Silva, E.F. Pimenta, O. Thiemann, M.R.Z. Passarini and L.D. Sette. 2008. A multi-screening approach for marine-derived fungal metabolites and the isolation of cyclodepsipeptides from Beauveria felina. Quim. Nov. 31: 1099-1103.
6. Elbarbry, F.A. and A.S. Shoker. 2007. Therapeutic drug measurement of mycophenolic acid derivatives in transplant patients. Clin. Biochem. 40: 752-764.
7. Elsaesser, B., K. Krohn, U. Floerke, N. Root, H.J. Aust, S. Draeger, Schulz, S. Antus and T. Kurtan. 2005. X-ray structure determination, absolute configuration and biological activity of phomox-anthone A. Eur. J. Org. Chem. 21: 4563-4570.
8. Faizi, S., R.A. Khanl, N.R. Mughall, M.S. Malik, K. Sajjadi and A. Ahmad. 2008. Antimicrobial activity of various parts of Polyalthia longifolia var. pendula: isolation of active principles from the leaves and the berries. Phytother. Res. 22: 907-912.
9. Guimarães, D.O., W.S. Borges, C.Y. Kawano, P.H. Ribeiro, G.H. Goldman, A. Nomizo, O.H. Thiemann, G. Oliva, N.P. Lopes and M.T. Pupo. 2008. Biological activities from extracts of endo-phytic fungi isolated from Viguiera arenaria and Tithonia diver-sifolia. FEMS Immunol. Med. Microbiol. 52: 134-144.
10. Hill, R.A. 2007. Marine natural products. Annu. Rep. Prog. Chem., Sect B 103: 125-139.
11. Hoog, G.S., V. Vicente, R.B. Caligiorne, S. Kantarcioglu, K. Tintelnot, A.H.G. van den Ende and G. Haase. 2003. Species diversity and polymorphism in the Exophiala spinifera clade containing opportunistic black yeast-like fungi. J. Clin. Microbiol. 41: 4767-4778.
12. Horn, W.S., R.E. Schwartz, M.S.J. Simmonds and W.M Blaney. Isolation and characterization of phomodiol, a new anti-fungal from Phomopsis. Tetrahedron Lett. 35: 6037-6040.
13. Horn, W.S., M.S.J. Simmonds, R.E. Schwatz and W.M. Blaney. Phomopsichalasin, a novel antimicrobial agent from an endophytic Phomopsis sp. Tetrahedron 51: 3969-3978.
14. Isaka, M., A. Jaturapat, K. Rukseree, K. Danwisetkanjana, M. Tanticharoen and Y. Thebtaranonth. 2001. Phomoxanthones A and B, novel xanthone dimmers from the endophytic fungus Phomopsis species. J. Nat. Prod. 64: 1015-1018.
15. Jones, E.B.G., S.J. Stanley and U. Pinruan. 2008. Marine endophyte sources of new chemical natural products: a review. Bot. Mar. 51: 163-170.
16. Kjer, J., A. Debbab, A.H. Aly and P. Proksch. 2010. Methods for isolation of marine-derived endophytic fungi and their bioactive secondary products. Nat. Protoc. 5: 479-490.
17. Kobayashi, H., S. Meguro, T. Yoshimoto and M. Namikoshi. 2003. Absolute structure, biosynthesis, and anti-microtubule activity of phomopsidin, isolated from a marine-derived fungus Phomopsis sp. Tetrahedron 59: 455-459.
18. Kohlmeyer, J. 1968. Revisions and descriptions of algicolous marine fungi. Phytopathol. Z. 63: 342-363.
19. Kohlmeyer, J. and B. Volkmann-Kohlmeyer. 2003. Marine ascomycetes from algae and animal hosts. Bot. Mar. 46: 285-306.
20. Kossuga, M.H., S.P. Lira, S. McHugh, Y.R. Torres, B.A. Lima, R. Goncalves, K. Veloso, A.G. Ferreira, R.M. Rocha and R.G.S. Berlinck. 2009. Antibacterial modified diketopiperazines from two ascidians of the genus Didemnum. J. Bras. Chem. Soc. 20: 704-711.
21. Krohn, K., A. Michel, E. Roemer, U. Floerke, H.J. Aust, S. Draeger, B. Schultz and V. Wray. 1995. Biologically active metabolites from fungi. 6. Phomosines A-C. Three new biaryl ethers from Phomopsis sp. Nat. Prod. Lett. 6: 309-314.
22. Kumar, S., K. Tamura and M. Nei. 2004. MEGA3: integrated software for molecular evolutionary genetics analysis and sequence alignment. Brief. Bioinf. 5: 150-153.
23. National Committee for Clinical Laboratory Standards. 2003. NCCLS document M7-A6-Methods for dilution antimicrobial susceptibility tests for bacteria that grow aerobically. NCCLS, Wayne, PA.
24. Ondeyka, J., O.D. Hensens, D. Zink, R. Ball, R.B. Lingham and G. Bills. 1992. L-696,474, a novel cytochalasin as an inhibitor of HIV-1 protease. II. Isolation and structure. J. Antibiot. 45: 679-685.
25. Petersen, P.J., T.Z. Wang, R.G. Dushin and P.A. Bradford. 2004. Comparative in vitro activities of AC98-6446, a novel semisyn-thetic glycopeptide derivative of the natural product mannopeptimycin à, and other antimicrobial agents against gram-positive clinical isolates. Antimicrob. Agents Chemother. 48: 739-746.
26. Ríos, J.L. and M.C. Recio. 2005. Medicinal plants and antimicrobial activity. J. Ethnopharmacol. 100: 80-84.
27. Rovirosa, J., A. Díaz-Marrero, J. Darias, K. Painemal and A. San Martin. 2006. Secondary metabolites from marine Penicillium brevicompactum. J. Chil. Chem. Soc. 51: 775-778.
28. Rukachaisirikul, V., U. Sommart, S. Phongpaichit, J. Sakayaroj and K. Kirtikara. 2008. Metabolites from the endophytic fungus Phomopsis sp. PSU-D15. Phytochemistry 69: 783-787.
29. Schulz, B., S. Draeger, T.E. dela Cruz, J. Rheinheimer, K. Siems, S. Loesgen, J. Bitzer, O. Schloerke, A. Zeeck, I. Kock, H. Hussain, J. Daí and K. Krohn. 2008. Screening strategies for obtaining novel, biologically active, fungal secondary metabolites from marine habitats. Bot. Mar. 51: 219-234.
30. Tan, R.X. and W.X. Zou. 2001. Endophytes: a rich source of functional metabolites. Nat. Prod. Rep. 18: 448-459.
31. Thompson, J.D., D.G. Higgins, T.J. Gibson and W. Clustal. 1994. Improving the sensitivity of progressive multiple alignment through sequence weighting, positions-specific gap penalties and weight matrix choice. Nucleic Acids Res. 22: 4673-4680.
32. Wagenaar, M.M. and J. Clardy. 2001. Dicerandrols, new antibiotic and cytotoxic dimers produced by the fungus Phomopsis longicolla isolated from an endangered mint. J. Nat. Prod. 64: 1006-1009.
33. Wagenaar, M.M., J. Corwin, G. Strobel and J. Clardy. 2000. Three new cytochalasins produced by an endophytic fungus in the genus Rhinocladiella. J. Nat. Prod. 63: 1692-1695.
34. Wrigley, S.K., R. Sadeghi, S. Bahl, A.J. Whiting, A.M. Ainsworth, S. Martin, W. Katzer, R. Ford, D.A. Kau, N. Robinson, M.A. Hayes, C. Elcock, T. Mander and M.J. Moore. 1999. A novel (6S)-4,6-di-methyldodeca-2E,4E-dienoyl ester of phomalactone and related apyrone esters from a Phomopsis sp. with cytokine production inhibitory activity. J. Antibiot. 52: 862-872.
35. Yang, G., L. Sandjo, K. Yun, A.S. Leutou, G. Kim, H.D. Choi, J.S. Kang, J. Hong and B. Son. 2011. Flavusides A and B, antibacterial cerebrosides from the marine-derived fungus Aspergillus flavus. Chem. Pharm. Bull. 59: 1174-1177.
36. Zuccaro, A. and J.I. Mitchell. 2005. Fungal communities of seaweeds. In. (J. Dighton, J.F. White and P. Oudemans, eds.) The fungal community. 3 rd edition. CRC Press, New York. pp. 533-579.