Skip to main content

Occurrence, isolation and biological activity of phytotoxic metabolites produced in vitro by Sphaeropsis sapinea, pathogenic fungus of Pinus radiata

European Journal of Plant Pathology volume 115, Article number: 187 (2006) Cite this article

Abstract

Sphaeropsis sapinea was repeatedly isolated in Sardinia from symptomatic samples of the upper part of declining pine (Pinus radiata) plants. Observed symptoms mainly consisted of foliage chlorosis, drying of needles and cankers on branches. The S. sapinea strains were shown to produce phytotoxic metabolites in culture filtrates. Three metabolites were isolated for the first time from this fungus and identified by their spectroscopic and optical properties as R-(−)-mellein, (3R,4R)-4-hydroxymellein and (3R,4S)-4-hydroxymellein. When assayed for phytotoxic and antifungal activities on host and non-host plants and on some phytopathogenic fungi, the R-(−)-mellein showed significant activity, while the other two 3,4-dihydroisocoumarins showed only a synergic activity in both tests.

This is a preview of subscription content, access via your institution.

Access options

Buy single article

Instant access to the full article PDF.

USD 39.95

Price includes VAT (USA)
Tax calculation will be finalised during checkout.

References

  • Alfatafta AA, Glover JB, Scott JA, Malloch D (1994) Apiosporamide, a new antifungal agent from the coprophilus fungus Apoispora montegnei. Journal of Natural Products 57: 1696–1702

    PubMed  Article  CAS  Google Scholar 

  • Anderson JR, Edwards RL (1983) Metabolites of the higher fungi. Part 21. 3-Methyl-3,4-dihydroisocoumarins and related compounds from the Ascomycete family Xylariaceae. Journal of Chemical Society, Perkin Transaction 1: 2185–2192

    Article  Google Scholar 

  • Aldridge DC, Galt S, Giles D and Turner WB (1971) Metabolites of Lasiodiplodia theobromae. Journal of Chemical Society, 1623–1627

  • Batoko H, de Kerchove d’Exaerde A, Kinet JM, Bouharmont J, Gage RA, Maraite H, Boutry M (1998) Modulation of plant plasma membrane H+-ATPase by phytotoxic lipodepsipeptides produced by plant pathogen Pseudomonas fuscovaginae. Biochimical et Biophysical Acta 1372: 216–226

    Article  CAS  Google Scholar 

  • Batoko H, Flamand MC, Boutry M, Kinet JM, Maraite H (1997) Biological effects of Pseudomonas fuscovaginae toxins on rice cells. Developmenta Plant Pathology 9: 215–229

    CAS  Google Scholar 

  • Berger S, Braun S (2004) 200 and More Basic NMR Experiments: A Practical Course. Wiley-VCH, Weinheim

    Google Scholar 

  • Camarda L, Merlini L, Nasini G (1976) Metabolites of Cercospora. Taiwapyrone, an α-pyrone of unusual structure from Cercospora taiwanensis. Phytochemistry 15: 537–539

    Article  CAS  Google Scholar 

  • Carpinella MC, Ferrayoli CG, Palacios SM (2005) Antifungal synergistic effect of Scopoletin, a hydroxycoumarin isolated from Melia azedarach L. fruits. Journal of Agricultural and Food Chemistry 53: 2922–2927

    PubMed  Article  CAS  Google Scholar 

  • Claydon N, Allan M, Hanson JR, Avent AG (1987) Antifungal alkyl pyrones of Trichoderma harzianum. Transactions of the British Mycological Society 88: 503–513

    CAS  Article  Google Scholar 

  • Cole JC, Cox RH (1981) Handbook of Toxic Metabolites. Academic Press, New York, pp. 129–151

    Google Scholar 

  • Cole RJ, Moore JH, Davis ND, Kirksey JW, Diener U (1971) 4-Hydroxymellein: A new metabolite of Aspergillus ochraceus. Journal of Agricultural and Food Chemistry 19: 909–911

    Article  CAS  Google Scholar 

  • Creppy EE, Chiarappa P, Baudrimont I, Borracci P, Moukha S, Carratù MR (2004) Synergistic effects of fumonisin B1 and ochratoxin A: Are in vitro cytotoxicity data predictive of in vivo acute toxicity? Toxicology 201: 115–123

    PubMed  Article  CAS  Google Scholar 

  • Devys M, Barbier M (1992) Isolation of the new (−)-(3R,4S)-4-hydroxymellein from the fungus Septoria nodorum Berk. Zeitschrift fuer Naturforschung 47c: 779–881

    Google Scholar 

  • Devys M, Bousquet J, Kollmann A, Barbier M (1980) Dihydroisocoumarines et acide mycophenolique du milieu de culture du champignon phytopathogene Septoria nodorum. Phytochemistry 19: 2221–2222

    Article  CAS  Google Scholar 

  • Edwards RL, Maitland DJ, Oliver CL, Pacey MS, Shields L, Whalley AJS (1999) Metabolites of the higher fungi. Part 31. Longianone, a C7H6O4 spiro bicyclic lactone from the fungus Xylaria longiana (Rehm.). Journal of Chemical Society, Perkin Transaction 1: 715–719

    Article  Google Scholar 

  • Evidente A, Sparapano L, Fierro O, Bruno G, Motta A (1999) Sapinofuranones A and B, two new 2(3H)-dihydrofuranones produced by Sphaeropsis sapinea, a common pathogen of conifers. Journal of Natural Products 62: 253–256

    PubMed  Article  CAS  Google Scholar 

  • Evidente A, Sparapano L, Motta A, Giordano F, Fierro O, Frisullo S (1996) A phytotoxic pimarane diterpene of Sphaeropsis sapinea f. sp. cupressi, the pathogen of a canker disease of cypress. Phytochemistry 42: 1541–1546

    Article  CAS  Google Scholar 

  • Garson MJ, Staunton J, Jones PG (1984) New polyketide metabolites from Aspergillus melleus: Structural and stereochemical studies. Journal of Chemical Society, Perkin Transaction 1: 1021–1026

    Article  Google Scholar 

  • Hachiro O (1988) Role of phytotoxins in pine wilt disease. Journal of Nematology 20: 245–251

    Google Scholar 

  • Hershernhorn J, Park SH, Stierle A, Strobel GA (1992) Fusarium avenaceum as a novel pathogen of spotted knapweed and its phytotoxins, acetamido-butenolide and enniatin B. Plant Science 86: 155–160

    Article  Google Scholar 

  • Hoeller U, Koening GM, Wright AD (1999) Three new metabolites from marine-derived fungi of the genera Coniothyrium and Microsphaeropsis. Journal of Natural Products 62: 114–118

    Article  CAS  Google Scholar 

  • Holker JSE, Simpson T (1981) Studies on fungal metabolites. Part 2. Carbon-13 nuclear magnetic resonance biosynthetic studies on pentaketide metabolites of Aspergillus melleus: 3-(1,2-Epoxypropyl)-5,6-dihydro-5-hydroxy-6-methyl-pyran-2-one and Mellein. Journal of Chemical Society, Perkin Transaction 1: 1397–1400

    Article  Google Scholar 

  • Krohn K, Bahramsari R, Florke U, Ludewig K, Klichespory C, Michel A, Aust H, Draeger S, Schulz B, Antus S (1997) Dihydroisocoumarins from fungi: isolation, structure elucidation, circular dichroism and biological activity. Phytochemistry 45: 313–320

    PubMed  Article  CAS  Google Scholar 

  • Linde C, Kemp GHJ (1997) First report of Sphaeropsis canker on cypress in South Africa. European Journal of Forest Pathology 27: 173–177

    Article  Google Scholar 

  • Parisi A, Piattelli M, Tringali C, Magnano Di San Lio G (1993) Identification of the phytotoxin Mellein in culture fluids of Phoma tracheiphila. Phytochemistry 32: 865–867

    Article  CAS  Google Scholar 

  • Sparapano L, Bruno G, Fierro O, Evidente A (2004) Studies on structure–activity relationships of spharopsidins A–F, phytotoxins produced by Sphaeropsis sapinea f. sp. cupressi. Phytochemistry 65: 189–198

    PubMed  Article  CAS  Google Scholar 

  • Stanosz GR, Swart WJ, Smith DR (1998) Similarity between fungi identified as Diplodia pinea f. sp. cupressi in Israel and Botryosphaeria stevensii or Diplodia mutila on Juniperus in the United States. European Journal of Forest Pathology 28: 33–42

    Article  Google Scholar 

  • Swart WJ, Wingfield MJ, Grant WS (1993) Comparison of Sphaeropsis sapinea and Sphaeropsis sapinea f. sp. cupressi. Mycological Research 97: 1253–1260

    Article  Google Scholar 

  • Turner WB, Aldridge DC (1983) Fungal Metabolites II. Academic Press, London, pp. 82–109

    Google Scholar 

  • Venkatasubbaiah P, Chilton WS (1990) Phytotoxins of Botryosphaeria obtusa. Journal of Natural Products 53: 1628–1630

    Article  CAS  Google Scholar 

  • Venkatasubbaiah P, Sutton TB, Chilton WS (1991) Effect of phytotoxins produced by Botryosphaeria obtusa, the cause of black rot of apple fruit and frogeye leaf spot. Phytopathology 81: 243–247

    Article  CAS  Google Scholar 

  • Xenopoulos S, Tsopelas P (2000) Sphaeropsis canker, a new disease of cypress in Greece. Forest Pathology 30: 121–126

    Article  Google Scholar 

Download references

Acknowledgements

The authors thank the Servizio di Spettrometria di Massa del CNR e dell’Università di Napoli Federico II (the assistance of the staff is gratefully acknowledged) and Dr. Lia Ferracane for EI and ESI mass spectra and CIMCF of Università di Napoli Federico II for NMR spectra. This work was supported by a grant from the Italian Ministry of University and Research (MIUR). Contribution DISSPA 102.

Author information

Authors and Affiliations

  1. Dipartimento di Protezione delle Piante, Università di Sassari, Via E. De Nicola, 07100, Sassari, Italy

    Annalisa Cabras, Maria A. Mannoni & Salvatorica Serra

  2. Dipartimento di Scienze del Suolo della Pianta e dell’Ambiente, Università di Napoli Federico II, Via Università 100, 80055, Portici, Italy

    Anna Andolfi, Michele Fiore & Antonio Evidente

Authors
  1. Annalisa Cabras
    View author publications

    You can also search for this author in PubMed Google Scholar

  2. Maria A. Mannoni
    View author publications

    You can also search for this author in PubMed Google Scholar

  3. Salvatorica Serra
    View author publications

    You can also search for this author in PubMed Google Scholar

  4. Anna Andolfi
    View author publications

    You can also search for this author in PubMed Google Scholar

  5. Michele Fiore
    View author publications

    You can also search for this author in PubMed Google Scholar

  6. Antonio Evidente
    View author publications

    You can also search for this author in PubMed Google Scholar

Corresponding author

Correspondence to Antonio Evidente.

Rights and permissions

Reprints and Permissions

About this article

Cite this article

Cabras, A., Mannoni, M.A., Serra, S. et al. Occurrence, isolation and biological activity of phytotoxic metabolites produced in vitro by Sphaeropsis sapinea, pathogenic fungus of Pinus radiata . Eur J Plant Pathol 115, 187 (2006). https://doi.org/10.1007/s10658-006-9006-7

Download citation

  • Received:

  • Accepted:

  • Published:

  • DOI: https://doi.org/10.1007/s10658-006-9006-7

Keywords

  • declining pine disease
  • isocoumarines
  • melleins
  • phytotoxic and antifungal activity
  • Pinus radiata
  • Sphaeropsis sapinea