Bioactive metabolites from the endophytic fungus Ampelomyces sp. isolated from the medicinal plant Urospermum picroides

Phytochemistry

Volumn 69, Issue 8, 2008, Pages 1716-1725

  Aly, Amal H ^a   Edrada Ebel, RuAngelie ^b   Wray, Victor ^c   Müller, Werner E G ^d   Kozytska, Svitlana ^e   Hentschel, Ute ^e   Proksch, Peter ^a   Ebel, Rainer ^f  

^a HEINRICH HEINE UNIVERSITY   (Germany)

^b UNIVERSITY OF STRATHCLYDE   (United Kingdom)

^c HELMHOLTZ CENTRE FOR INFECTION RESEARCH   (Germany)

^d JOHANNES GUTENBERG UNIVERSITY   (Germany)

^e UNIVERSITY OF WÜRZBURG   (Germany)

^f UNIVERSITY OF ABERDEEN   (United Kingdom)

Author keywords

Ampelomyces; Anthraquinones; Antibacterial activity; Chromones; Cytotoxic activity; Endophytic fungi; Pyrones

Indexed keywords

ANTIINFECTIVE AGENT; CYTOTOXIN;

ANIMAL; ARTICLE; ASCOMYCETES; ASTERACEAE; BACTERIUM; CHEMICAL STRUCTURE; CHEMISTRY; DRUG EFFECT; DRUG SCREENING; GROWTH, DEVELOPMENT AND AGING; ISOLATION AND PURIFICATION; LEUKEMIA L 5178 Y; MASS FRAGMENTOGRAPHY; MEDICINAL PLANT; METABOLISM; MICROBIOLOGICAL EXAMINATION; MICROBIOLOGY; MOUSE; TUMOR CELL LINE;

ANIMALS; ANTI-INFECTIVE AGENTS; ASCOMYCOTA; ASTERACEAE; BACTERIA; CELL LINE, TUMOR; CYTOTOXINS; DRUG SCREENING ASSAYS, ANTITUMOR; GAS CHROMATOGRAPHY-MASS SPECTROMETRY; LEUKEMIA L5178; MICE; MICROBIAL SENSITIVITY TESTS; MOLECULAR STRUCTURE; PLANTS, MEDICINAL;

AMPELOMYCES; ENTEROCOCCUS FAECALIS; FUNGI; POSIBACTERIA; STAPHYLOCOCCUS AUREUS; STAPHYLOCOCCUS EPIDERMIDIS; UROSPERMUM PICROIDES;

EID: 42749093846     PISSN: 00319422     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.phytochem.2008.02.013     Document Type: Article

References (32)

1. Akira W., Ono Y., Fujii I., Sankawa U., Mayorga M.E., Timberlake W.E., and Ebizuka Y. Product identification of polyketide synthase coded by Aspergillus nidulans wA gene. Tetrahedron Lett. 39 (1998) 7733-7736
2. Andrews J.M. Determination of minimum inhibitory concentrations. J. Antimicrob. Chemother. 48 (2001) 5-16
3. Ashour M., Edrada R.A., Ebel R., Wray V., Wätjen W., Padmakumar K., Müller W.E.G., Lin W.H., and Proksch P. Kahalalide derivatives from the indian sacoglossan mollusk Elysia grandifolia. J. Nat. Prod. 69 (2006) 1547-1553
4. Bacon C.W., and White J.F. Microbial Endophytes (2000), Marcel Dekker Inc., New York pp. 4-5
5. Carmichael J., DeGraff W.G., Gazdar A.F., Minna J.D., and Mitchell J.B. Evaluation of a tetrazolium-based semiautomated colorimetric assay: Assessment of radiosensitivity. Cancer Res. 47 (1987) 943-946
6. Connolly J.D. Structural elucidation of some natural products. In: Atta-Ur-Rahman (Ed). Studies in Natural Products Chemistry vol. 9 (1991), Elsevier Science Publishers B.V., Amsterdam 256-258
7. Ebel R. Secondary metabolites from marine-derived fungi. In: Proksch P., and Müller W.E.G. (Eds). Frontiers in Marine Biotechnology (2006), Horizon Scientific Press, Norwich 73-143
8. Fehr M.J., Consiglio G., Scalone M., and Schmid R. Asymmetric hydrogenation of substituted 2-pyrones. J. Org. Chem. 64 (1999) 5768-5776
9. Haraguchi H., Abo T., Hashimoto K., and Yagi A. Action-mode of antimicrobial altersolanol A in Pseudomonas aeruginosa. Biosci. Biotechnol. Biochem. 56 (1992) 1221-1224
10. Höller U., Gloer J.B., and Wicklow D.T. Biologically active polyketide metabolites from an undetermined fungicolous hyphomycete resembling Cladosporium. J. Nat. Prod. 65 (2002) 876-882
11. Kiss L., Russell J.C., Szentivanyi O., Xu X., and Jeffries P. Biology and biocontrol potential of Ampelomyces mycoparasites, natural antagonists of powdery mildew fungi. Biocontrol Sci. Technol. 14 (2004) 635-651
12. 16 from Coniothyrium sp.: isolation, structure elucidation, and biological activity. Liebigs Ann. Chem. (1994) 1099-1108
13. Kwong T.F.N., Miao L., Li X., and Qian P.Y. Novel antifouling and antimicrobial compound from a marine-derived fungus Ampelomyces sp. Mar. Biotechnol. 8 (2006) 634-640
14. Larsen T.O., and Breinholt J. Dichlorodiaportin, diaportinol, and diaportinic acid: three novel isocoumarins from Penicillium nalgiovense. J. Nat. Prod. 62 (1999) 1182-1184
15. Lazarovits G., Steele R.W., and Stoessl A. Dimers of altersolanol A from Alternaria solani. Z. Naturforsch. 43c (1988) 813-817
16. Lee H.J., Choi J.S., Jung J.H., and Kang S.S. Alaternin glucoside isomer from Cassia tora. Phytochemistry 49 (1998) 1403-1404
17. Menichetti F. Current and emerging serious gram-positive infections. Clin. Microbiol. Infect. 11 (2005) 22-28
18. Okamura N., Haraguchi H., Hashimoto K., and Yagi A. Altersolanol-related antimicrobial compounds from a strain of Alternaria solani. Phytochemistry 34 (1993) 1005-1009
19. Okamura N., Mimura K., Haraguchi H., Shingu K., Miyahara K., and Yagi A. Altersolanol-related compounds from the culture liquid of Alternaria solani. Phytochemistry 42 (1996) 77-80
20. Plasencia J., and Mirocha C.J. Isolation and characterization of zearalenone sulfate produced by Fusarium spp. Appl. Environ. Microbiol. 57 (1991) 146-150
21. 13C nuclear magnetic resonance spectroscopic investigation. Can. J. Chem. 56 (1978) 2681-2685
22. Shishkoff N., and McGrath M.T. AQ10 biofungicide combined with chemical fungicides or AddQ spray adjuvant for control of cucurbit powdery mildew in detached leaf culture. Plant Dis. 86 (2002) 915-918
23. Stoessl A., and Stothers J.B. Tetrahydroaltersolanol B, a hexahydroanthronol from Alternaria solani. Can. J. Chem. 61 (1983) 378-382
24. Strobel G.A. Rainforest endophytes and bioactive products. Crit. Rev. Biotechnol. 22 (2002) 315
25. Strzelecka M., Bzowska M., Koziel J., Szuba B., Dubiel O., Riviera-Nunez D., Heinrich M., and Bereta J. Antiinflammatory effects of extracts from some traditional Mediterranean diet plants. J. Physiol. Pharmacol. 56 (2005) 139-156
26. Suemitsu R., Sano T., Yamamoto M., Arimoto Y., Morimatsu F., and Nabeshima T. Structural elucidation of alterporriol B, a novel metabolic pigment produced by Alternaria porri (Ellis) Ciferri. Agric. Biol. Chem. 48 (1984) 2611-2613
27. Suemitsu R., Ohnishi K., Yanagawase S., Yamamoto K., and Yamada Y. Biosynthesis of macrosporin by Alternaria porri. Phytochemistry 28 (1989) 1621-1622
28. Sundheim L., and Krekling T. Host-parasite relationships of the hyperparasite Ampelomyces quisqualis and its powdery mildew host Sphaerotheca fuliginea. J. Phytopathol. 104 (1982) 202-210
29. Teeyapant R., Woerdenbag H.J., Kreis P., Hacker J., Wray V., Witte L., and Proksch P. Antibiotic and cytotoxic activity of brominated compounds from the marine sponge Verongia aerophoba. Z. Naturforsch. 48c (1993) 939-945
30. Wang S., Li X.M., Teuscher F., Li D.L., Diesel A., Ebel R., Proksch P., and Wang B.G. Chaetopyranin, a benzaldehyde derivative, and other related metabolites from Chaetomium globosum, an endophytic fungus derived from the marine red alga Polysiphonia urceolata. J. Nat. Prod. 69 (2006) 1622-1625
31. Yagi A., Okamura N., Haraguchi H., Abo T., and Hashimoto K. Antimicrobial tetrahydroanthraquinones from a strain of Alternaria solani. Phytochemistry 33 (1993) 87-91
32. Yarwood C.E. Ampelomyces quisqualis on clover mildew. Phytopathology 22 (1932) 31