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.
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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
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
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
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
Berger S, Braun S (2004) 200 and More Basic NMR Experiments: A Practical Course. Wiley-VCH, Weinheim
Camarda L, Merlini L, Nasini G (1976) Metabolites of Cercospora. Taiwapyrone, an α-pyrone of unusual structure from Cercospora taiwanensis. Phytochemistry 15: 537–539
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
Claydon N, Allan M, Hanson JR, Avent AG (1987) Antifungal alkyl pyrones of Trichoderma harzianum. Transactions of the British Mycological Society 88: 503–513
Cole JC, Cox RH (1981) Handbook of Toxic Metabolites. Academic Press, New York, pp. 129–151
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
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
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
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
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
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
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
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
Hachiro O (1988) Role of phytotoxins in pine wilt disease. Journal of Nematology 20: 245–251
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
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
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
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
Linde C, Kemp GHJ (1997) First report of Sphaeropsis canker on cypress in South Africa. European Journal of Forest Pathology 27: 173–177
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
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
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
Swart WJ, Wingfield MJ, Grant WS (1993) Comparison of Sphaeropsis sapinea and Sphaeropsis sapinea f. sp. cupressi. Mycological Research 97: 1253–1260
Turner WB, Aldridge DC (1983) Fungal Metabolites II. Academic Press, London, pp. 82–109
Venkatasubbaiah P, Chilton WS (1990) Phytotoxins of Botryosphaeria obtusa. Journal of Natural Products 53: 1628–1630
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
Xenopoulos S, Tsopelas P (2000) Sphaeropsis canker, a new disease of cypress in Greece. Forest Pathology 30: 121–126
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.
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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, 187–193 (2006). https://doi.org/10.1007/s10658-006-9006-7
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DOI: https://doi.org/10.1007/s10658-006-9006-7