Artículo

Gallardo, G.L.; Butler, M.; Gallo, M.L.; Rodríguez, M.A.; Eberlin, M.N.; Cabrera, G.M. "Antimicrobial metabolites produced by an intertidal Acremonium furcatum" (2006) Phytochemistry. 67(21):2403-2410
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Abstract:

In a screening for antimicrobial metabolites, amides of d-allo- and l-isoleucine derivatives were isolated from the culture of a marine strain of Acremonium furcatum. Structural elucidation of these compounds was performed by analysis of spectroscopic data and confirmed by synthesis. All of the compounds, natural and synthetic intermediates, were bioassayed against bacteria and phytopathogenic fungi, with many showing remarkable antifungal activities. © 2006 Elsevier Ltd. All rights reserved.

Registro:

Documento: Artículo
Título:Antimicrobial metabolites produced by an intertidal Acremonium furcatum
Autor:Gallardo, G.L.; Butler, M.; Gallo, M.L.; Rodríguez, M.A.; Eberlin, M.N.; Cabrera, G.M.
Filiación:Departamento de Química Orgánica, Facultad de Ciencias Exactas y Naturales, Universidad de Buenos Aires, Ciudad Universitaria, Pab. II, 1428 Buenos Aires, Argentina
DBBE, FCEN, UBA, Ciudad Universitaria, Pab. II, 1428 Buenos Aires, Argentina
Thomson Mass Spectrometry Laboratory, Instituto de Química, Universidade Estadual de Campinas, 13083-970 Campinas, SP, Brazil
Palabras clave:Acremonium furcatum; Antifungal activity; Colletotrichum truncatum; Fusarium virguliforme; Isoleucinaldehyde; Isoleucine derivatives; Isoleucinol; Marine fungi; antiinfective agent; Acremonium; article; bacterium; chemical structure; chemistry; drug effect; metabolism; Acremonium; Anti-Bacterial Agents; Bacteria; Molecular Structure; Acremonium (Ascomycota); Acremonium furcatum; Bacteria (microorganisms); Colletotrichum; Colletotrichum truncatum; Fungi; Fusarium; Fusarium virguliforme
Año:2006
Volumen:67
Número:21
Página de inicio:2403
Página de fin:2410
DOI: http://dx.doi.org/10.1016/j.phytochem.2006.07.028
Título revista:Phytochemistry
Título revista abreviado:Phytochemistry
ISSN:00319422
CODEN:PYTCA
CAS:Anti-Bacterial Agents
Registro:https://bibliotecadigital.exactas.uba.ar/collection/paper/document/paper_00319422_v67_n21_p2403_Gallardo

Referencias:

  • Abdel-Lateff, A., König, G.M., Fisch, K.M., Holler, U., Jones, P.G., Wright, A.D., New antioxidant hydroquinone derivatives from the algicolous marine fungus Acremonium sp. (2002) J. Nat. Prod., 65, pp. 1605-1611
  • Belofsky, G.N., Anguera, M., Jensen, P.R., Fenical, W., Kock, M., Oxepinamides A-C and fumiquinazolines H-I: bioactive metabolites from a marine isolate of a fungus of the genus Acremonium (2000) Chemistry - Eur. J., 6, pp. 1355-1360
  • Bringmann, G., Lang, G., Gulder, T.A.M., Tsuruta, H., Mühlbacher, J., Maksimenka, K., Steffens, S., Müller, W.E.G., The first sorbicillinoid alkaloids, the antileukemic sorbicillactones A and B, from a sponge-derived Penicillium chrysogenum strain (2005) Tetrahedron, 61, pp. 7252-7265
  • Cabrera, G.M., Roberti, M.J., Wright, J.E., Seldes, A.M., Cryptoporic and isocryptoporic acids from the fungal cultures of Polyporus arcularius and P. ciliatus (2002) Phytochemistry, 61, pp. 189-193
  • Ceroni, M., Séquin, U., Determination of the relative configurations in the side chains of the antibiotics hedamycin and pluramycin A: synthesis and NMR. Data of suitable model compounds (1982) Helv. Chim. Acta, 65, pp. 302-316
  • Che, Y., Gloer, J.B., Koster, B., Malloch, D., Decipinin A and decipienolides A and B: new bioactive metabolites from the coprophilous fungus Podospora decipiens (2002) J. Nat. Prod., 65, pp. 916-919
  • Christophersen, C., Crescente, O., Frisvad, J.C., Gram, L., Nielsen, J., Nielsen, P.H., Rabaek, L., Antibacterial activity of marine-derived fungi (1999) Mycopathologia, 143, pp. 135-138
  • Corey, E.J., Suggs, J.W., Pyridinium chlorochromate. An efficient reagent for oxidation of primary and secondary alcohols to carbonyl compounds (1975) Tetrahedron Lett., 31, pp. 2647-2650
  • Davidson, B.S., New dimensions in natural products research: cultured marine microorganisms (1995) Curr. Opin. Biotechnol., 6, pp. 284-291
  • Fenical, W., Jensen, P.R., Marine microorganisms: a new biomedical resource (1993) Marine Biotechnology, 1, pp. 419-457. , Attaway D.H., and Zaborsky O.R. (Eds), Plenum Press
  • Gallo, M.L., Seldes, A.M., Cabrera, G.M., Antibiotic long-chain and α,β-unsaturated aldehydes from the culture of the marine fungus Cladosporium sp. (2004) Biochem. Syst. Ecol., 32, pp. 545-551
  • Hamada, Y., Shibata, M., Sugiura, T., Kato, S., Shioiri, T., New methods and reagents in organic synthesis. 67. A general synthesis of derivatives of optically pure 2-(1-aminoalkyl)thiazole-4-carboxylic acids (1987) J. Org. Chem., 52, pp. 1252-1255
  • Harding, K.E., May, L.M., Dick, K.F., Selective oxidation of allylic alcohols with chromic acid (1975) J. Org. Chem., 40, pp. 1664-1665
  • Homans, A.L., Fuchs, A., Direct bioautography on thin-layer chromatography as a method for detecting fungitoxic substances (1970) J. Chromatogr., 51, pp. 325-328
  • Iwamoto, T., Fujiie, A., Tsurumi, Y., Nanbata, K., Shibuya, K., FR900403, a new antifungal produced by a Kernia sp. (1990) J. Antibiot., 43, pp. 1183-1185
  • Jaworski, A., Bruckner, H., Sequences of polypeptide antibiotics stilboflavins, natural peptaibol libraries of the mold Stilbella flavipes (2001) J. Pept. Sci., 7, pp. 433-447
  • Kawakami, Y., Matsuwaka, S., Otani, T., Kondo, H., Nakamura, S., Ileumycin, a new antibiotic against Glomerella cingulata (1978) J. Antibiot., 31, pp. 112-116
  • Kawashima, J., Ito, F., Kato, T., Niwano, M., Koshino, H., Uramoto, M., Antitumor activity of heptelidic acid chlorohydrin (1994) J. Antibiot., 47, pp. 1562-1563
  • Kennedy, T.C., Webb, G., Cannell, R.J.P., Kinsman, O.S., Middletton, R.F., Sidebottom, P.J., Taylor, N.L., Buss, A.D., Novel inhibitors of fungal protein synthesis produced by a strain of Graphium putredinis. Isolation, characterization and biological properties (1998) J. Antibiot., 51, pp. 1012-1018
  • Kern, A., Kabatek, U., Jung, G., Werner, R.G., Poetsch, M., Záhner, H., Amiclenomycin peptides. Isolation and structure elucidation of new biotin antimetabolites (1985) Liebigs Ann. Chem., p. 877
  • Klausner, Y., Bodanski, M., Coupling reagents in peptide synthesis (1972) Synthesis, pp. 453-463
  • Kobayashi, J., Ishibashi, M., Bioactive metabolites of symbiotic marine microorganisms (1993) Chem. Rev., 93, pp. 1753-1769
  • Koh, L.L., Tan, T.K., Chou, L.M., Goh, N.K.C., Antifungal properties of Singapore gorgonians: a preliminary study (2002) J. Exp. Mar. Biol. Ecol., 273, pp. 121-130
  • Levy, L.M., Cabrera, G.M., Wright, J.E., Seldes, A.M., 5H-furan-2-ones from the culture of the fungus Aporpium caryae (2003) Phytochemistry, 62, pp. 239-242
  • MacDonald, J.C., Bishop, G.G., Mazurek, M., Empirical equations for predicting 13 C chemical shifts in nuclear magnetic resonance spectra of certain types of aminoacids (1976) Can. J. Chem., 54, pp. 1226-1233
  • Munday-Finch, S.C., Miles, C.O., Wilkins, A.L., Hawkes, A.D., Isolation and structure elucidation of lolitrem A, a tremorgenic mycotoxin from perennial ryegrass infected with Acremonium lolii (1995) J. Agric. Food Chem., 43, pp. 1283-1288
  • Proksa, B., Adamcová, J., Fuska, J., 2-Methylsorbic acid, an antifungal metabolite of Penicillium vermiculatum (1992) Appl. Microbiol. Biotechnol., 37, pp. 443-445
  • Rabaek, L., Sperry, S., Piper, J.E., Crews, P., Deoxynortrichoharzin, a new polyketide from the saltwater culture of a sponge-derived Paecilomyces fungus (1998) J. Nat. Prod., 61, pp. 1571-1573
  • Schiehser, G.A., White, J.D., Matsumoto, G., Pezzanite, J.O., Clardy, J., The structure of leptosphaerin (1986) Tetrahedron Lett., 27, pp. 5587-5590
  • Sharman, G.J., Try, A.C., Williams, D.H., Ainsworth, A.M., Beneyto, R., Gibson, T.M., McNicholas, C., Wrigley, S.K., Structural elucidation of XR586, a peptaibol-like antibiotic from Acremonium persicinum (1996) Biochem. J., 320, pp. 723-728
  • Toki, S., Ando, K., Yoshida, M., Matsuda, Y., PS-990, a novel neuritogenic compound from Acremonium sp. (1994) J. Antibiot., 47, pp. 1175-1181

Citas:

---------- APA ----------
Gallardo, G.L., Butler, M., Gallo, M.L., Rodríguez, M.A., Eberlin, M.N. & Cabrera, G.M. (2006) . Antimicrobial metabolites produced by an intertidal Acremonium furcatum. Phytochemistry, 67(21), 2403-2410.
http://dx.doi.org/10.1016/j.phytochem.2006.07.028
---------- CHICAGO ----------
Gallardo, G.L., Butler, M., Gallo, M.L., Rodríguez, M.A., Eberlin, M.N., Cabrera, G.M. "Antimicrobial metabolites produced by an intertidal Acremonium furcatum" . Phytochemistry 67, no. 21 (2006) : 2403-2410.
http://dx.doi.org/10.1016/j.phytochem.2006.07.028
---------- MLA ----------
Gallardo, G.L., Butler, M., Gallo, M.L., Rodríguez, M.A., Eberlin, M.N., Cabrera, G.M. "Antimicrobial metabolites produced by an intertidal Acremonium furcatum" . Phytochemistry, vol. 67, no. 21, 2006, pp. 2403-2410.
http://dx.doi.org/10.1016/j.phytochem.2006.07.028
---------- VANCOUVER ----------
Gallardo, G.L., Butler, M., Gallo, M.L., Rodríguez, M.A., Eberlin, M.N., Cabrera, G.M. Antimicrobial metabolites produced by an intertidal Acremonium furcatum. Phytochemistry. 2006;67(21):2403-2410.
http://dx.doi.org/10.1016/j.phytochem.2006.07.028