Planta Med 2002; 68(11): 1052-1054
DOI: 10.1055/s-2002-35670
Letter
© Georg Thieme Verlag Stuttgart · New York

5-Hydroxyramulosin, a New Natural Product Produced by Phoma tropica, a Marine-Derived Fungus Isolated from the Alga Fucus spiralis

Claudia Osterhage1 , Gabriele M. König1 , Peter G. Jones2 , Anthony D. Wright1
  • 1Current address: Institute for Pharmaceutical Biology, University of Bonn, Nußallee 6, Bonn, Germany
  • 2Institute for Inorganic and Analytical Chemistry, Technical University of Braunschweig, Braunschweig, Germany
Further Information

Publication History

Received: February 13, 2002

Accepted: June 29, 2002

Publication Date:
26 November 2002 (online)

Abstract

The fungus Phoma tropica was isolated from the inner tissue of the marine brown alga Fucus spiralis. After large-scale cultivation the fungus was investigated for its secondary metabolite content and found to contain the new natural product 5-hydroxyramulosin (1) together with 7-methoxycoumarin. Both structures were elucidated using spectroscopic methods, mainly 1D and 2D NMR, and in the case of 1, a single crystal X-ray diffraction analysis.

References

  • 1 Höller U, König G M, Wright A D. A new tyrosine kinase inhibitor from a marine isolate of Ulocladium botrytis and new metabolites from the marine fungus Asteromyces cruciatus and Varicosporina ramulosa . European Journal of Organic Chemistry 1999: 2949-55
  • 2 Wegner C, Kaminsky R, König G M, Wright A D. Ascosalipyrrolidinone A, an antimicrobial alkaloid, from the obligate marine fungus Ascochyta salicorniae .  Journal of Organic Chemistry. 2000;  65 6412-17
  • 3 König G M, Wright A D. Marine natural products research: Current directions and future potential.  Planta Medica. 1996;  62 193-211
  • 4 Soledade M, Pedras C, Taylor J L, Nakashima T T. A novel chemical signal from the ”Blackleg” fungus: Beyond phytotoxins and phytoalexins.  Journal of Organic Chemistry. 1993;  58 4778-80
  • 5 Capasso R, Evidente A, Vurro M. Cytochalasins from Phoma exigua var. heteromorpha .  Phytochemistry. 1991;  12 3945-50
  • 6 Ichihara A, Oikawa H, Hashimoto M, Sakamura S, Haraguchi T, Nagano H. A phytotoxin, betaenone C, and its related metabolites of Phoma betae Fr.  Agricultural and Biological Chemistry. 1983;  47 2965-7
  • 7 Wegner C, Schwibbe M, König G M, Wright A D. Differences between marine and terrestrial Phoma species as determined by HPLC-DAD and HPLC-MS.  Phytochemical Analysis.. 2000;  11 288-94
  • 8 Wright A D, König G M, Angerhofer C K, Greenidge P, Linden A, Desqueyroux-Faundéz R. Antimalarial activity: The search for marine derived natural products which demonstrate selective antimalarial activity.  Journal of Natural Products. 1996;  59 710-6
  • 9 Kirsch G, König G M, Wright A D, Kaminsky R. A new bioactive sesterterpene and antiplasmodial alkaloids from the marine sponge Hyrtios cf. erecta .  Journal of Natural Products. 2000;  63 825-9
  • 10 Sheldrick G M. 1997. SHELXL-97. University of Göttingen Göttingen, Germany;
  • 11 Zubía E, Luis F R, Massanet G M, Collado I G. An efficient synthesis of furanocoumarins.  Tetrahedron. 1992;  20 4239-46
  • 12 Devys M, Barbier M, Bousquet J -F, Kollmann A. Isolation of the (-)-(3R)-5-hydroxymellein from the fungus Septoria nodorum .  Phytochemistry. 1994;  3 825-6
  • 13 Venkatasubbaiah P, Chilton W S. Phytotoxins of Botryosphaeria obtusa .  Journal of Natural Products. 1990;  6 1628-30
  • 14 Osborne A G. 13C-NMR spectral studies of some methoxycoumarin derivatives. A re-assignment of citropten (limettin) and an examination of peri-proximity effects for the methyl-methoxy and methoxy-methyl couples.  Magnetic Resonance in Chemistry. 1989;  27 348-54

Dr. Anthony D. Wright

Institute for Pharmaceutical Biology

University of Bonn

Nußallee 6

53115 Bonn

Germany