Two new cyclopentanoids from the endophytic fungus Aspergillus sydowii associated with the marine alga Acanthophora spicifera

Natural Product Communications

Volumn 1, Issue 11, 2006, Pages 927-933

  Teuscher, Franka ^a   Lin, Wenhan ^b   Wray, Victor ^c   Edrada, Ru Angelie ^a   Padmakumar, K ^d   Proksch, Peter ^a   Ebel, Rainer ^a  

^a HEINRICH HEINE UNIVERSITY   (Germany)

^b PEKING UNIVERSITY   (China)

^c HELMHOLTZ CENTRE FOR INFECTION RESEARCH   (Germany)

^d UNIVERSITY OF KERALA   (India)

Author keywords

Algicolous fungi; Cyclopentanoids; Marine derived fungi; Natural products

Indexed keywords

EID: 38949184622     PISSN: 1934578X     EISSN: 15559475     Source Type: Journal    
DOI: 10.1177/1934578x0600101103     Document Type: Article

References (36)

1. Strobel G, Daisy B, Castillo U, Harper J. (2004) Natural products from endophytic microorganisms. Journal of Natural Products, 67, 257-268.
2. Strobel G. (2002) Microbial gifts from rain forests. Canadian Journal of Plant Pathology, 24, 14-20.
3. Kohlmeyer J, Kohlmeyer E. (1979) Marine Mycology-The Higher Fungi. Academic Press, New York, pp. 54-69.
4. Biabani MAF, Laatsch, H. (1998) Advances in chemical studies on low-molecular weight metabolites of marine fungi. Journal für Praktische Chemie/Chemiker-Zeitung, 340, 589-607.
5. Schulz B, Römmert AK, Dammann U, Aust HJ, Strack D. (1999) The endophyte-host interaction: a balanced antagonism? Mycological Research, 103, 1275-1283.
6. Zuccaro A, Schulz B, Mitchell JI. (2003) Molecular detection of ascomycetes associated with Fucus serratus. Mycological Research, 107, 1451-1466.
7. Ebel, R. (2006) Secondary metabolites from marine-derived fungi. In Frontiers in Marine Biotechnology. Proksch P, Müller WEG (Eds). Horizon Bioscience, Wymondham, UK, pp. 73-143.
8. Bugni TS, Ireland CM. (2004) Marine-derived fungi: a chemically and biologically diverse group of microorganisms. Natural Product Reports, 21, 143-163.
9. Schulz B, Boyle C, Draeger S, Römmert AK, Krohn K. (2002) Endophytic fungi: a source of novel biologically active secondary metabolites. Mycological Research, 106, 996-1004.
10. Cueto M, Jensen PR, Kauffman C, Fenical W, Lobkovsky E, Clardy J. (2001) Pestalone, a new antibiotic produced by a marine fungus in response to bacterial challenge. Journal of Natural Products, 64, 1444-1446.
11. Osterhage C, König GM, Höller U, Wright AD. (2002) Rare sesquiterpenes from the algicolous fungus Drechslera dematioidea. Journal of Natural Products, 65, 306-313.
12. Yanagihara M, Sasaki-Takahashi N, Sugahara T, Yamamoto S, Shinomi M, Yamashita I, Hayashida M, Yamanoha B, Numata A, Yamori T, Andoh T (2005) Leptosins isolated from marine fungus Leptoshaeria species inhibit DNA topoisomerases I and/or II and induce apoptosis by inactivation of Akt/protein kinase B. Cancer Science, 96, 816-824;
13. Yamada T, Iwamoto C, Yamagaki N, Yamanouchi T, Minoura K, Hagishita S, Numata A. (2004) Leptosins O-S, cytotoxic metabolites of a strain of Leptosphaeria sp. isolated from a marine alga. Heterocycles, 63, 641-653;
14. Yamada T, Iwamoto C, Yamagaki N, Yamanouchi T, Minoura K, Yamori T, Uehara Y, Andoh T, Umemura K, Numata A. (2002) Leptosins M-N1, cytotoxic metabolites from a Leptosphaeria species separated from a marine alga. Structure determination and biological activities. Tetrahedron, 58, 479-487;
15. Takahashi C, Minoura K, Yamada T, Numata A, Kushida K, Shingu T, Hagishita S, Nakai H, Sato T, Harada H. (1995) Potent cytotoxic metabolites from a Leptosphaeria species. Structure determination and conformational analysis. Tetrahedron, 51, 3483-3498;
16. Takahashi C, Takai Y, Kimura Y, Numata A, Shigematsu N, Tanaka H. (1995) Cytotoxic metabolites from a fungal adherent of a marine alga. Phytochemistry, 38, 155-158;
17. Takahashi C, Numata A, Matsumura E, Minoura K, Eto H, Shingu T, Ito T, Hasegawa T. (1994) Leptosins I and J, cytotoxic substances produced by a Leptosphaeria sp. Physico-chemical properties and structures. Journal of Antibiotics, 47, 1242-1249;
18. Takahashi C, Numata A, Ito Y, Matsumura E, Araki H, Iwaki H, Kushida K. (1994) Leptosins, antitumor metabolites of a fungus isolated from a marine alga. Journal of the Chemical Society, Perkin Transactions 1: Organic and Bio-Organic Chemistry (1972-1999), 1859-1864.
19. Olutiola PO, Cole OO. (1977) Some environmental and nutritional factors affecting growth and sporulation of Aspergillus sydowi. Physiologia Plantarum, 39, 239-242.
20. Rinaldi MG. (1983) Invasive aspergillosis. Reviews of Infectious Diseases, 5, 1061-1077.
21. Alker AP, Smith GW, Kim K. (2001) Characterization of Aspergillus sydowii (Thom et Church), a fungal pathogen of Caribbean sea fan corals. Hydrobiologia, 460, 105-111.
22. Geiser DM, Taylor JW, Ritchie KB, Smith GW (1998) Cause of sea fan death in the West Indies. Nature, 394, 137-138.
23. Hamasaki T, Nagayama K, Hatsuda Y. (1978) Two new metabolites, sydonic acid and hydroxysydonic acid, from Aspergillus sydowi. Agricultural and Biological Chemistry, 42, 37-40.
24. Fukuyama K, Tsukihara T, Katsube Y, Hamasaki T, Hatsuda Y. (1976) Structural analysis of sydowic acid by x-ray diffraction. Agricultural and Biological Chemistry, 40, 1053-1054;
25. Hamasaki T, Sato Y, Hatsuda Y. (1975) Isolation of new metabolites from Aspergillus sydowi and structure of sydowic acid. Agricultural and Biological Chemistry, 39, 2337-2340;
26. Hamasaki T, Sato Y, Hatsuda Y, Tanabe M, Cary LW. (1975) Sydowic acid. New metabolite from Aspergillus sydowi. Tetrahedron Letters, 659-660.
27. Edwards, RL, Elsworthy GC, Kale, N. (1967) Constituents of the higher fungi. IV. Involutin, a diphenylcyclopentenone from Paxillus involutus. Journal of the Chemical Society [Section] C: Organic, 405-409;
28. Edwards R, Gill M. (1973) Constituents of the higher fungi. XII. Identification of involutin as (-)-cis-5-(3,4-dihydroxyphenyl)-3,4-dihydroxy-2- (4-hydroxyphenyl)cyclopent-2-enone and synthesis of (+-)-cis-involutin trimethyl ether from isoxerocomic acid derivatives. Journal of the Chemical Society, Perkin Transactions 1: Organic and Bio-Organic Chemistry (1972-1999), 1529-1537.
29. Antkowiak, R, Antkowiak WZ, Banczyk I, Mikolajczyk L. (2003) A new phenolic metabolite, involutone, isolated from the mushroom Paxillus involutus. Canadian Journal of Chemistry, 81, 118-124.
30. Steglich W, Thilmann A, Besl H, Bresinsky A. (1977) Pigments of fungi. 29. 2,5-Diarylcyclopentane-1,3-diones from Chamonixia caespitosa (Basidiomycetes). Zeitschrift für Naturforschung, C: Journal of Biosciences, 32C, 46-48.
31. Besl H, Bresinsky A, Steglich W, Zipfel K. (1973) Fungus pigments. XVII. Gyrocyanin, the blueing principle of Gyroporus cyanescens, and an oxidative ring contraction of atromentin. Chemische Berichte, 106, 3223-3229.
32. Feling R, Polborn K, Steglich W, Mühlbacher J, Bringmann G. (2001) The absolute configuration of the mushroom metabolites involutin and chamonixin. Tetrahedron, 57, 7857-7863.
33. For a review, see Bringmann G, Lang G. (2003). Novel marine natural products. Part 3. Full absolute stereostructures of natural products directly from crude extracts: the HPLC-MS/MS-NMR-CD 'triad'. In Sponges (Porifera). Müller, WEG (Ed). Springer, Berlin, pp. 89-116, and references cited within.
34. Gill M, Steglich W. (1987) Pigments of fungi (Macromycetes) Progress in the Chemistry of Organic Natural Products, 51, 63-70;
35. Besl H, Bresinsky A, Herrmann R, Steglich W. (1980) Fungal pigments. 37. Chamonixin and involutin, two chemosystematically interesting cyclopentanediones from Gyrodon lividus (Boletales). Zeitschrift für Naturforschung, C: Journal of Biosciences, 35c, 824-825;
36. Bresinsky A, Besl H, Steglich W. (1974) Gyroporin and atromentin acid from Leccinum aurantiacum cultures. Phytochemistry, 13, 271-272.