Chemical and biological characterisation of sapinopyridione, a phytotoxic 3,3,6-trisubstituted-2,4-pyridione produced by Sphaeropsis sapinea, a toxigenic pathogen of native and exotic conifers, and its derivatives

Phytochemistry

Volumn 67, Issue 10, 2006, Pages 1019-1028

  Evidente, Antonio ^a   Fiore, Michele ^a   Bruno, Giovanni ^b   Sparapano, Lorenzo ^b   Motta, Andrea ^c  

^a UNIVERSITY OF NAPLES FEDERICO II   (Italy)

^b UNIVERSITY OF BARI   (Italy)

^c CNR   (Italy)

Author keywords

3,3,6 Trisubstituted 2,4 pyridione; Bioactivity; Conifer pathogen; Phytotoxins; Sapinopyridione derivatives; Sphaeropsis sapinea; Structure activity relationship

Indexed keywords

ANTIFUNGAL AGENT; MYCOTOXIN; PYRIDONE DERIVATIVE; SAPINOPYRIDIONE;

ARTICLE; ASCOMYCETES; CHEMISTRY; CUPRESSUS; DRUG EFFECT; ISOLATION AND PURIFICATION; MASS SPECTROMETRY; MICROBIOLOGY; NUCLEAR MAGNETIC RESONANCE;

ANTIFUNGAL AGENTS; ASCOMYCOTA; CUPRESSUS; MASS SPECTROMETRY; MYCOTOXINS; NUCLEAR MAGNETIC RESONANCE, BIOMOLECULAR; PYRIDONES;

CONIFEROPHYTA; CUPRESSUS; CUPRESSUS MACROCARPA; CUPRESSUS SEMPERVIRENS; SEIRIDIUM; SPHAEROPSIS SAPINEA;

EID: 33646940120     PISSN: 00319422     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.phytochem.2006.03.017     Document Type: Article

References (44)

1. Altomare C., Pengue R., Favilla M., Evidente A., and Visconti A. Structure activity relationship of derivatives of fusapyrone, a new antifungal metabolite of Fusarium semitectum. J. Agric. Food Chem. 52 (2004) 2997-3001
2. Andolfi A., Boari A., Evidente A., and Vurro M. Metabolites inhibiting germination of Orobanche ramosa seeds produced by Myrothecium verrucaria and Fusarium compactum. J. Agric. Food Chem. 53 (2005) 1598-1603
3. Baumeler H.R., and Dibach U.C. Pyrithyldione elimination in urine. Methods and results from different groups. Schweiz. Med. Wschr. 106 (1976) 710-713
4. Berger S., and Braun S. 200 and More Basic NMR Experiments: a Practical Course (2004), VCH, Weinheim
5. Blogget J.T., and Stanosz G.R. Sphaeropsis sapinea morphotypes differ in aggressiveness, but both infect non-wounded red or jack pines. Plant Dis. 81 (1997) 143-147
6. Borchert H.H., Schuster S., Lipfert H., and Pfeifer S. Is the pyrithyldione (Benedorm) an enzyme inductor?. Pharmazie 37 (1982) 69
7. Breitmaier E., and Voelter W. Carbon-13 NMR Spectroscopy (1987), VCH, Weinheim pp. 183-293
8. Capasso R., Iacobellis N.S., Bottalico A., and Randazzo G. Structure-toxicity relationships of the eremophilane phomenone and PR-toxins. Phytochemistry 23 (1984) 2781-2784
9. Celimene C.C., Smith D.R., Young R.A., and Stanosz G.R. In vitro inhibition of Sphaeropsis sapinea by natural stilbenes. Phytochemistry 56 (2001) 161-165
10. Chou C.K. A shoot dieback in Pinus radiata caused by Diplodia pinea. I. Symptoms, disease development and isolation of pathogen. New Zealand J. For. Sci. 6 (1976) 72-79
11. Chou C.K. Crown wilt of Pinus radiata associated with Diplodia pinea infection of woody stems. Eur. J. For. Pathol. 17 (1987) 398-411
12. Cole R.J., and Cox R.H. Handbook of Toxic Metabolites (1981), Academic Press, New York, NY, USA pp. 152-263
13. de Wet J., Wingfield M.J., Coutinho T.A., and Wingfield B.D. Characterization of Sphaeropsis sapinea isolates from South Africa, Mexico and Indonesia. Plant Dis. 84 (2000) 151-156
14. de Wet J., Wingfield M.J., Coutinho T., and Wingfield B.D. Characterization of the 'C' morphotype of the pine pathogen Sphaeropsis sapinea. For. Ecol. Manage. 161 (2002) 181-188
15. de Wet J., Burgess T., Slippers B., Preisig O., Wingfield B.D., and Wingfield M.J. Multiple gene genealogies and microsatellite markers reflect relationships between morphotypes of Sphaeropsis sapinea and distinguish a new species of Diplodia. Mycol. Res. 107 (2003) 557-566
16. Evidente A., Cabras A., Maddau L., Serra S., Andolfi A., and Motta A. Viridepyronone, a new antifungal 6-ubstituted 2H-pyran-2-one roduced by Trichoderma viride. J. Agric. Food Chem. 51 (2003) 6957-6960
17. Evidente A., Sparapano L., Fierro O., Bruno G., Giordano F., and Motta A. Sphaeropsidone and episphaeropsidone, phytotoxic dimedone methyl ethers produced by Sphaeropsis sapinea f. sp cupressi grown in liquid culture. Phytochemistry 48 (1998) 1139-1143
18. Evidente A., Sparapano L., Fierro O., Bruno G., and Motta A. Sapinofuranones A and B, two new 2(3H)-dihydrofuranones produced by Sphaeropsis sapinea, a common pathogen of conifers. J. Nat. Prod. 62 (1999) 253-256
19. Findlay J.A., and Kwan D. Synthesis of flavipucine reduction product. J. Chem. Soc. Perkin I (1972) 1962-1963
20. Findlay J.A., and Radics L. Flavipucine [3′-isovaleryl-6-methylpyridine-3-spiro-2′-oxiran-2(1H)-4(3H )-dione], an antibiotic from Aspergillus flaviceps. J. Chem. Soc. Perkin I (1972) 2071-2074
21. Frisullo S., Bruno G., Lops F., and Sparapano L. Un nuovo agente di "cancro" del Cipresso in Italia. Petria 7 (1997) 141-158
22. Gibson I.A.S. Diseases of Forest Trees Widely Planted as Exotics in the Tropic and Southern Hemisphere. Part II. The Genus Pinus (1979), Commonwealth Mycological Institute, Kew, Surrey, UK
23. Girotra N.N., and Wendler N.L. The relative configuration of flavipucine. Tetrahedron Lett. (1979) 4793-4796
24. Hausner G., Hopkin A.A., Davis C.N., and Reid J. Variation in culture and rDNA among isolates of Sphaeropsis sapinea from Ontario and Manitoba. Can. J. Plant Pathol. 21 (1999) 256-264
25. Nakanishi K., and Solomon P.H. Infrared Absorption Spectroscopy. second ed. (1977), Holden Day, Oakland pp. 17-49, 252
26. Palmer M.A., Stewart E.L., and Wingfield M.J. Variation among isolates of Sphaeropsis sapinea in the north central United States. Phytopathology 77 (1987) 944-948
27. Peter S.W., Findlay J.A., and Tam W.H.J. The X-ray crystal structure of (±)-flavipucine. Can. J. Chem. 56 (1978) 1904-1906
28. Porter Q.N. Mass Spectrometry of Heterocyclic Compound. second ed. (1985), Wiley, New York pp. 581-625
29. Pretsch P.D.E., Clerc T., Seibl J., and Simon W. Tables of Spectral Data for Structure Determination of Organic Compounds (1989), Springer, Berlin pp. H5-H17, H55-H65, H150-H160, H215-H220, M210-M255
30. Rudy B.C., and Senkowski B.Z. Metipranolol [3,3-diethyl-5-methyl-2,4-piperidinedione]. Analytical profile. Anal. Prof. Drug Sub. Excip. 2 (1973) 363-382
31. Sassa T. Structure and absolute configuration of Macrophoma fruit rot toxin. Agric. Biol. Chem. 47 (1983) 1417-1418
32. Sassa T., and Onuma Y. Isolation and identification of fruit rot toxins from the fungus-caused Macrophoma fruit rot of apple. Agric. Biol. Chem. 47 (1983) 1155-1157
33. Scott A.I. Interpretation of the Ultraviolet Spectra of Natural Compounds (1964), Pergamon Press, Oxford pp. 178-184
34. Smith D.R., and Stanosz G.R. Confirmation of two distinct populations of Sphaeropsis sapinea in the north central United States using RAPDs. Phytopathology 85 (1995) 699-704
35. Sparapano L., Bruno G., Fierro O., and Evidente A. Studies on structure-activity relationships of sphaeropsidins A-F, phytotoxins produced by Sphaeropsis sapinea f. sp. cupressi. Phytochemistry 65 (2004) 189-198
36. Stanosz G.R., and Cummings Carlson J. Association of mortality of recently planted seedlings and established saplings in red pine plantations with Sphaeropsis collar rot. Plant Dis. 80 (1996) 750-753
37. Stanosz G.R., Smith D.R., and Guthmiller M.A. Characterization of Sphaeropsis sapinea from the west central United States by means of random amplified polymorphic DNA marker analysis. Plant Dis. 80 (1996) 1175-1178
38. Stanosz G.R., Swart W.J., and Smith D.R. RAPD marker and isoenzyme characterization of Sphaeropsis sapinea from diverse coniferous hosts and locations. Mycol. Res. 103 (1999) 1193-1202
39. Sutton B.C. Coelomycetes (1980), Commonwealth Mycological Institute, Kew, Surrey, UK pp. 120-121
40. Swart W.J., and Wingfield M. Biology and control of Sphaeropsis sapinea on Pinus species in South Africa. Plant Dis. 75 (1991) 761-766
41. Vurro M., Bottalico A., Capasso R., and Evidente A. Cytocalasins from phytopathogenic Ascochyta and Phoma species. In: Upahyay R.K., and Mukerji K.G. (Eds). Toxins in Plants Disease Development and Evolving Biotechnology (1997), Oxford & IBH Publishing Co. Pvt. Ltd., New Delhi 127-147
42. White P.S., Findlay J.A., and Wah Hung J.T. The X-ray crystal structure of (±)-flavipucine. Can. J. Chem. 56 (1978) 1904-1906
43. Wang C.G., Blanchette R.A., Jackson W.A., and Palmer M.A. Differences in conidial morphology among isolates of Sphaeropsis sapinea. Plant Dis. 69 (1985) 838-841
44. Zwolinski J.B., Swart W.J., and Wingfield M.J. Intensity of dieback induced by Sphaeropsis sapinea in relation to site conditions. Eur. J. For. Pathol. 20 (1990) 167-174