Phytotoxins produced by fungi responsible of forestall plant diseases

Sustainable Agriculture: Technology, Planning and Management

Volumn , Issue , 2010, Pages 177-234

  Evidente, Antonio ^a   Andolfi, Anna ^a   Cimmino, Alessio ^a   Abouzeid, Mohamed A ^b  

^a UNIVERSITY OF NAPLES FEDERICO II   (Italy)

^b AIN SHAMS UNIVERSITY   (Egypt)

Author keywords

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EID: 84892050952     PISSN: None     EISSN: None     Source Type: Book    
DOI: None     Document Type: Chapter

References (187)

1. Ahlrichs, R; Bar, M; Baron, HP; Bauernschmitt, R; Bocker, S; Ehrig, M; Eichkorn, K; Elliott, S; Furche, F; Haase, F; Haser, M; Horn, H; Hattig, C.; Huber, C.; Huniar, U; Kattannek, M.; Kohn, A.; Kolmes, C; Kollwitz, M; May, K.; Ochsenfeld, C.; Öhm, H.; Schafer, A; Schneider, U; Treutler, O; Arnim, MV; Weigend, F; Weis, P; Weiss, H TURBOMOLE, version 5.6. Karlsruhe, Germany: Universitat Karlsruhe; 2002.
2. Alfatafta, AA; Glover, JB; Scott, JA; Malloch, D. Apiosporamide, a new antifungal agent from the coprophilus fungus Apoispora montegnei. J. Nat. Prod., 1994 57, 1696-1702.
3. Aldridge, DC; Galt, S; Giles, D; Turner, WB. Metabolites of Lasiodiplodia theobromae, J. Chem. Soc., 1971, 1623-1627.
4. Altomare, C; Pengue, R; Favilla, M; Evidente; Visconti, A. Structure activity relationship of derivatives of fusapyrone, a new antifungal metabolite of Fusarium semitectum. J. Agric. Food Chem., 2004 52, 2997-3001.
5. Anderson, JR; and Edwards, RL. Metabolites of the higher fun. Part 21. 3-Methyl-3,4-dihydroisocoumarins and related compounds from the Ascomycete family Xylariaceae. J. Chem. Soc. Perkin Trans., 1983 1, 2185-2192.
6. Andolfi, A; Boari, A; Evidente, A; Vurro, M. Metabolites inhibiting germination of Orobanche ramosa seeds produced by Myrothecium verrucaria and Fusarium compactum, J. Agric. Food Chem., 2005 53, 1598-1603.
7. Ballio, A; Castiglione Morelli, MA; Evidente, A; Graniti, A.; Randazzo, G; Sparapano, L., Seiricardine A, a phytotoxic sesquiterpene from three Seiridium species pathogenic for cypress. Phytochemistry, 1991 30, 131-136.
8. Ballio, A; Evidente, A; Graniti, A; Randazzo, G; Sparapano, L. Seiricuprolide, a new phytotoxic macrolide from a strain of Seiridium cupressi infecting cypress. Phytochemistry, 1988 27, 3117-3121.
9. Ballio, A; Graniti, A. Phytotoxins and their involvement in plant disease. Experientia, 1991 47, 751-826.
10. Barros, MT; Maycock, CDM; Ventura, MR. Enantioselective total synthesis of (+)-Eutypoxide B. J. Org. Chem., 1997 62, 3984-3988.
11. Bartlett, AJ; Holker, JSE; O'Breien, E; Simpson, TJ. Biosynthesis of the meroterpenoid metabolite, andibenin B: aromatic precursors. J. Chem. Soc., Chem. Commun. 1981, 1198-1200.
12. Barthelet, J; Vinot, M. 'Notes sur les maladies des cultures méridionales. Annales des Epiphyties, 1944 10, 18-20.
13. Batoko, H; Flamand, MC; Boutry, M; Kinet, JM; Maraite, H. Biological effects of Pseudomonas fuscovaginae toxins on rice cells. Devol. Plant Pathol., 1997 9, 215-229.
14. Baumeler, HR; Dibach, UC. Pyrithyldione elimination in urine. Methods and results from different groups. Schweizerische Medizinische Wochenschrift, 1976 106, 710-713.
15. Behr, S; Hegeman, K; Schimanski, H; Froehlich, R; Haufe, G. Synthesis of-lactones from cycloocta-1,5-diene. Starting materials for natural product synthesis. Eur. J. Org. Chem. 2004 18, 3884-3892.
16. Borchert, HH; Schuster, S; Lipfter, H; Pfeifer, S. Is the pyrithyldione (Benedorm) an enzyme inductor? Pharmazie, 1982 37, 69.
17. Brasier, CM. Phytophthora cinnamomi and oak decline in southern Europe. Environmental constraints including climate change. Ann. For. Sci., 1996 53, 347-358.
18. Brasier, CM; Robredo, F; Ferraz, JFP. Evidence for Phytophthora cinnamomi involvement in Iberian oak decline. Plant Pathol., 1993 42, 140-145.
19. Breitmaier, E; Voelter, W. Carbon-13 NMR Spectroscopy, Weinheim: VCH; 1987; pp. 183-280.
20. Brown, RCD; Hughes, RM; Keily, J; Kenney, A. Diastereoselective synthesis of tetrahydrofuran containing fragments by the permanganate oxidation of 1,5,9-trienes. Chem. Commun., 2000, 175-1738
21. Buckingham, AD. Permanent and Induced Molecular Moments and Long-Range Intermolecular Forces. In Hirschfelder JO editor. Intermolecular Forces,. Wiley, New York: Adv. Chem. Phys; 1967; pp. 107.
22. Cabras, A; Mannoni, MA; Serra, S; Andolfi, A; Fiore, M; Evidente, A. Occurrence, isolation, and biological activity of phytotoxic metabolites produced in vitro by Sphaeropsis sapinea, pathogenic fungus of Pinus radiat. Eur. J. Plant Pathol., 2006, 115, 187-193.
23. Camarda, L; Merlini, L; Nasini, G. Metabolites of Cercospora. Taiwapyrone, an α-pyrone of unusual structure from Cercospora taiwanensis. Phytochemistry, 1976 15, 537-539.
24. Capasso, R; Iacobellis, NS; Bottalico, A; Randazzo, G. Structure-toxicity relationships of the eremophilane phomenone and PR-toxins. Phytochemistry, 1984 23, 2781-2784.
25. Carreno, MC; Merino, E; Ribagorda, M; Somoza, A; Urbano, A Org. Lett. 2005 7, 1419-1422.
26. Carpinella, MC; Ferrayoli, CG; Palacios, SM. Antifungal synergistic effect of Scopoletin, a hydroxycoumarin isolated from Melia azedarach L. fruits. J. Agric. and Food Chem., 2005 53, 2922-2927.
27. Charney, E. The molecular basis of optical activity optical rotatory dispersion and circular dichroism. New York: Wiley and Sons; 1979; pp.217-226.
28. Cheeseman, JR.; Frisch, MJ; Devlin, FJ; Stephens, PJ. Hartree-Fock and Density Functional Theory ab initio calculation of optical rotation using GIAOs: basis set dependence. J. Phys. Chem. A, 2000 104, 1039-1046.
29. Chou, CK. A shoot dieback in Pinus radiata caused by Diplodia pinea 1. Symptoms, disease development, isolation of pathogen. New Zealand J. Fores. Serv., 1976 6, 72-79.
30. Closse, A; Mauli, R; Sigg, HP. Die konstitution von epoxydon. Helv. Chim. Acta, 1966, 49, 204-213.
31. Clough, S; Raggatt, ME; Simpson, TJ; Wilis, LC; Whiting, A; Wrigley, SK. Structure elucidation and synthesis of (4S,5S,6Z,8E)-5-hydroxydeca-6,8-dien-4-olide [(S,S)-sapinofuranone B]-a novel-lactone metabolite of Acremonium strictum. J. Chem. Soc. Perkin Trans. I, 2000, 2475-2481.
32. Cole RJ; Moore, JH; Davis, ND; Kirksey, JW; Diener, U. 4-Hydroxymellein: a new metabolite of Aspergillus ochraceus. Agric. and Food Chem, 1971 19, 909-911.
33. Cole, RJ; Cox, RH. Handbook of Toxic Fungal Metabolites. New York,NY, USA: Academic Press; 1981; 152-263s.
34. Condon, EU. Theories of Optical Rotatory Power, Rev. Mod. Phys. 1937 9, 432-457.
35. Creppy, EE; Chiarappa, P; Baudrimont, I; Borracci, P; Moukha, S; Carratù, MR. Synergistic effects of fumonisin B1 and ochratoxin A: are in vitro cytotoxicity data predictive of in vivo acute toxicity. Toxicology, 2004 201, 115-123.
36. Crawford, TD. The ab initio calculation of molecular properties. Theor. Chem. Acc., 2006 115, 227-245.
37. Dale, JA; Dull, DL; Mosher, HS. α-Methoxy-α-trifluoromethylphenyl acetic, a versatile reagent for the determination of enantiomeric composition of alcohols and amines. J. Org. Chem., 1969 34, 2543-2549.
38. Dale, JA; Mosher, HS. Nuclear magnetic resonance enantiomer reagents. Configurational correlations via nuclear magnetic resonance chemical shifts of diastereomeric mandelate, O-methylmandelate, and α-methoxy-α-trifluoromethylphenyl acetate (MTPA) esters. J. Am. Chem. Soc., 1973 95, 512-519.
39. Dawe, RD; Molinski TF; Turner, V. Dilithium tetrabromonickelate (II) as a source of soft nucleophilic bromide: reaction with epoxides. Tetrahedron Lett., 1984 25, 2061-2064
40. Dean, FM. Naturally occurring oxygen ring compounds. London: Butterworths, 1963 pp. 53-81, 82-134, 553.
41. DeVoe, H. Optical properties of molecular aggregates. I. Classical model of electronic absorption and refraction. J.Chem.Phys. 1964 41, 393-400.
42. DeVoe, H. Optical properties of molecular aggregates. II. Classical theory of the refraction, absorption, and optical activity of solutions and crystal. ibidem 1965 43, 3199-3208.
43. Devys, M; Barbier, M. Isolation of the new (-)-(3R,4S)-4-hydroxymellein from the fungus Septoria nodorum Berk. Zeitschrift fuer Naturforschung, 1992 47c, 779-881.
44. Devys, M; Bousquet, J; Kollmann, A; Barbier, M. Dihydroisocoumarines et acide mycophenolique du milieu de culture du champignon phytopathogene Septoria nodorum. Phytochemistry, 1980 19, 2221-2222.
45. Dickinson, JM. Microbial pyran-2-ones and dihydropyran-2-ones. Nat. Prod. Rep. 1993 10, 71-98.
46. Drake, AF; Mason, SF. The absorption and circular dichroism spectra of chiral olefins. Tetrahedron, 1977 33, 937-949
47. Durbin, RD. Toxins In Plant in Disease , Academic Press, 1981.
48. Ellestad, GA; Kunstmann, MP; Mirando, P; Morton, GO. Structure of fungal diterpene antibiotics LL-S491 and . J. Am. Chem. Soc., 1972 94, 6206-6208.
49. Edwards, RL; Maitland, DJ; Oliver, CL; Pacey, MS; Shields, L; Whalley, AJS. Metabolites of the higher fung. Part 31. Longianone, a C7H6O4 spiro bicyclic lactone from the fungus Xylaria longiana (Rehm.). J. Chem. Soc. Perkin Trans., 1999 1, 715-719.
50. Evidente, A. 'Bioactive metabolites from phytopathogenic fungi and bacteria', In: Pandalai, SG editor Recent Research Developments in Phytochemistry. Trivandrum (India): Research Signpost; 1997; pp. 255-292.
51. Evidente, A; Andolfi, A; Fiore, M; Spanu, E; Franceschini, A; Maddau, L. Diplofuranones, A and B, two further new 4-monosubstituted 3(3H)-dihydrofuranones produced by Diplodia corticola, a fungus pathogen of cork oak. Arkivoc, 2007, vii, 318-328.
52. Evidente, A; Andolfi, A; Maddau, L; Franceschini, A; Marras, F. Biscopyran, a phytotoxic hexasubstituted pyranpyran produced by Biscognauxia mediterranea, a fungus pathogen of cork oak. J. Nat. Prod., 2005 68, 568-571.
53. Evidente, A; Andolfi, A; Fiore, M; Spanu, E; Maddau, L; Franceschini, A; Marras, F; Motta, A; Diplobifuranylones A and B, 5'-monosubstituted tetrahydro-2H-bifuranyl-5-ones produced by Diplopia corticola, a fungus pathogen of cork oak J. Nat. Prod., 2006b 69, 671-674.
54. Evidente, A; Cabras, A; Maddau, L; Serra, S; Andolfi A; Motta, A. Viridepyronone, a new antifungal 6-substituted 2H-pyran-2-one produced by Trichoderma viride. J. Agric. Food Chem., 2003b 51, 6957-6960.
55. Evidente, A; Capretti, P; Giordano, F; Surico, G. Identification and phytotoxicity of nitropropionic acid produced in vitro by Melanconis thelebola. Experientia, 1992 48, 1169-1172.
56. Evidente, A; Fiore, M, Bruno G.; Sparapano, L; Motta A. Chemical and biological characterization 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, 2006a 67, 1019-1028.
57. Evidente, A; Maddau, L; Spanu, E; Franceschini, A; Lazzaroni, S; Motta, A. Diplopyrone, a new phytotoxic tetrahydropyranpyran-2-one produced by Diplodia mutila, a fungus pathogen of cork oak. J. Nat. Prod., 2003c 66, 313-315.
58. Evidente, A; Motta, A. Phytotoxins from fungi pathogenic for agrarian, forestal and weedy plants. In: Tringali C. editor. Bioactive Compounds from Natural Sources. London, UK: Taylor and Francis; 2001; pp. 473-525.
59. Evidente, A; Motta, A. Bioactive metabolites from phytopathogenic bacteria and plants. In: Atta-ur-Rahman editor. Studies in Natural Products Chemistry. Amsterdam: Elsevier Science; 2002 26; pp. 581-628.
60. Evidente, A; Motta, A; Sparapano, L. Seiricardines B and C, phytotoxic sesquiterpenes from three species of Seiridium pathogenic for cypress. Phytochemistry, 1993 33, 69-78.
61. Evidente, A; Randazzo, G; Ballio, A. Structure determination of seiridin and isoseiridin, phytotoxic butenolides from culture filtrate of Seiridium cardinale, J. .Nat. Prod., 1986 49, 593-601.
62. Evidente, A: Sparapano, L. 7'-Hydroxyseiridin and 7'-hydroxyisoseiridin, two new phytotoxic Δα-butenolides from three species of Seiridium pathogenic to cypress. J. .Nat. Prod., 1994 57, 1720-1725.
63. Evidente, A; Sparapano, L; Motta, A; Giordano, F; Fierro, O; Frisullo, S. A phytotoxic pimarane diterpene of Sphaeropsis sapinea f. sp. cupressi, the pathogen of a canker disease of cypress. Phytochemistry, 1996 42, 1541-1546.
64. Evidente, A; Sparapano, L; Andolfi, A; Bruno, G; Giordano F; Motta, A. Chlorosphaeropsidone and epichlorosphaeropsidone, two new chlorinated dimedone methyl ethers isolated from liquid cultures of Sphaeropsis sapinea f. sp. cupressi, Phytopatol. Medit., 2000 39, 299-309.
65. Evidente, A; Sparapano, L; Andolfi, A; Bruno G; Motta, A. Sphaeropsidin F, a new pimarane diterpene produced in vitro by the cypress pathogen Sphaeropsis sapinea f. sp. cupressi. Aust. J. Chem., 2003a 56, 615-619.
66. Evidente, A; Sparapano, L; Bruno, G; Motta, A. Sphaeropsidins D and E, two other pimarane diterpenes, produced in vitro by the plant pathogenic fungus Sphaeropsis sapinea f.s. cupressi. Phytochemistry, 2002 59, 817-823.
67. Evidente, A; Sparapano, L; Fierro, O; Bruno, G; Giordano, F; Motta, A. Sphaeropsidone and episphaeropsidone, phytotoxic dimedone methyl ethers produced by Sphaeropsis sapinea f. sp. cupressi grown in liquid culture. Phytochemistry, 1998 48, 1139-1143.
68. Evidente, A; Sparapano, L; Fierro O; Bruno, G; Motta, A. Sapinofuranones A and B, two new 2(3H)-dihydrofuranones produced by Sphaeropsis sapinea, a common pathogen of conifers. J. Nat. Prod., 1999 62, 253-256.
69. Evidente, A; Sparapano, L; Giordano, F; Fierro, O; Motta, A. Sphaeropsidines B and C, phytotoxic pimarane diterpenes from Sphaeropsis sapinea f. sp. cupressi and Diplodia mutila. Phytochemistry, 1997 45, 705-713.
70. Fex, T; Wickberg, B. Structure and synthesis of the methyl ester of 3,4-anhydroshikimic acid, isolated from a Chalara sp. Acta Chem. Scand., 1981 B35, 91-95.
71. Findlay, JA; Kwan, D. Synthesis of flavipucine reduction product. J. Chem. Soc. Perkin I, 1972, 1962-1963.
72. Findlay, JA; Radics, L. Flavipucine [3'-isovaleryl-6-methylpyridine-3-spiro-2'-oxiran-2(1H)-4(3H)-dione)], an antibiotic from Aspergillus claviceps. J. Chem. Soc. Perkin I, 1972, 2071-2074.
73. Franceschini, A; Corda, P; Maddau, L; Marras, F. IOBC Bulletin, 1999 22, 5-12
74. Franceschini, A; Maddau, L; Marras, F. IOBC/wprs Bulletin, 2002 25, 29-36.
75. Frisullo, S; Bruno, G; Lops, F; Sparapano, L. 'Un nuovo agente di cancro del cipresso', Petria, 1997a 7, 141-158.
76. Frisullo, S; Bruno, G; Lops, F; Sparapano, L. Morphological, physiological and pathogenic studies on Sphaeropsis sapinea, S. sapinea f. sp. cupressi and Diplodia mutila. Proceed. 10th Cong. Medit. Phytopathol. Union, Montpellier, 1997, 201-205.
77. Fritz, JS; Schenk, GH. Acid-catalized acetylation of organic hydroxyl groups. Anal. Chem. 1959 31, 1808-1812.
78. Garson, MJ; Staunton, J; Jones, PG. New polyketide metabolites from Aspergillus melleus: structural and stereochemical studies. J. Chem. Soc. Perkin Trans., 1984 1, 1021-1026.
79. Gautier, ECL; Lewis, NJ; McKillop, A; Taylor, RJK. Synthesis of bromoxone. Tetrahedron Lett. 1994 35, 8759-8760.
80. Gibson, IAS. Diseases of forest trees widely planted as exotics in the tropic and southern hemisphere. Part II. The Genus Pinus. Kew, Surrey, UK: Commonwealth Mycological Institute; 1979; pp. 51.
81. Giorgio, E; Rosini, C; Viglione, RG; Zanassi. Calculation of the gas phase specific rotation of (S)-propylene oxide at 355 nm. Chem Phys. Lett., 2003 376, 452-456.
82. Giorgio, E; Maddau, L; Spanu, E; Evidente, A; Rosini, C. Assignment of the absolute configuration of (+)-diplopyrone, the main phytotoxin produced by Diplodia mutila, the pathogen of the cork oak decline, by a non empirical analysis of its chiroptical properties. J. Org. Chem., 2005 70, 7-13.
83. Girotra, NN; Wendler, NL. The relative configuration of flavipucine. Tetrahedron Lett., 1979, 4793-4796.
84. Gottarelli, G; Mason, SF; Torre, G. The circular dichroism and absolute configuration of (+)-trans-stilbene oxide. J. Chem. Soc B 1971, 1349-1353.
85. Graham, AE; McKerrecher, D; Huw Davies, D; Taylor, RJK. Sonogashira coupling reactions of highly oxygenated vinyl halides: The first synthesis of harveynone and epi-harveynone, Tetrahedron Lett,. 1996 37, 7445-7448.
86. Graham, AE; Taylor, RJK. Synthesis of tricholomenyn A and epitricholomenyn A by a palladium-catalysed β-halo enone coupling route J. Chem. Soc., Perkin Trans. 1 1997 1087-1090.
87. Graniti, A. Seiridium cardinale and other cypress cankers. EPPO Bulletin, 1985 16, 479-486.
88. Graniti, A. Cypress canker: a pandemic in progress. Ann. Rev. of Phytopathol., 1998 36, 91-114.
89. Graniti, A; Durbin, RD; Ballio, A. Phytotoxins and Plant Pathogenesis. NATO ASI Series H Series. Berlin: Springer-Verlag; 1989 27; pp. 508.
90. Graniti, A; Frisullo, S. Fungi associated with cypress canker disease in the Mediterranean area. Proceed. 7th Cong. Mediter. Phytopathol. Union, 1987, pp. 211-213.
91. Graniti, A; Sparapano, L; Evidente, A. Cyclopaldic acid, a major phytotoxic metabolite of Seiridium cupressi, the pathogen of a canker disease of cypress. Plant Pathol., 1992 41, 563-568.
92. Grasso, V; Raddi, P. Seminario: Il Cipresso: malattie e difesa, Firenze, Italia: CEE-AGRIMED; 23-24 Settembre 1979, pp-275.
93. Grotenbreg, GM; Tuin, AW; Witte, MD; Leeuwenburgh, MA; Van Boom, JH; Van der Marel, GA; Overkleeft, HS. Overhand, M. Synlett., 2004 5, 904-906.
94. Hachiro, O. Role of phytotoxins in pine wilt disease. Journal of Nematol., 1988 20, 245-251.
95. Hanson, JR. Terpenoids. In: Thomson RH editor. The Chemistry of Natural Products. Glasgow: Blackie; 1985; pp. 154-189.
96. Harada, N; Nakanishi, K. Circular Dichroic Spectroscopy: exciton coupling in organic stereochemistry. Mill Valley, CA: University Science Books; 1983; pp. 43.
97. Hausner, G; Hopkin, AA; Davis, CN; Reid, J. Variation in culture and rDNA among isolatews of Sphaeropsis sapinea from Ontario and Manitoba. Can. J. Plant Pathol., 1999 21, 256-264.
98. Helgaker, T; Jensen, HJA.; Joergensen, P; Olsen, J; Ruud, K; Aagren, H; Auer, AA; Bak, KL; Bakken, V; Christiansen, O; Coriani, S; Dahle, P; Dalskov, EK; Enevoldsen, T; Fernandez, B; Haettig, C; Hald, K; Halkier, A; Heiberg, H; Hettema, H; Jonsson, D; Kirpekar, S; Kobayashi, R; Koch, H; Mikkelsen, KV; Norman, P; Packer, MJ; Pedersen, TB; Ruden, TA; Sanchez, A; Saue, T.; Sauer, SPA; Schimmelpfennig, B; Sylvester-Hvid
99. KO; Taylor, PR; Vahtras,O. DALTON, a molecular electronic structure program, Release 1.2, 2001.
100. Hershernhorn, J; Park, SH; Stierle, A; Strobel, GA. Fusarium avenaceum as a novel pathogen of spotted knapweed and its phytotoxins, acetamido-butenolide and enniatin B, Develop. Plant Sci., 1992 86 155-160.
101. Hoeller, U; Koening, GM; Wright, AD. Three new metabolites from marine-derived fungi of the genera Coniothyrium and Microsphaeropsis, J. Nat. Prod., 1999 62: 114-118.
102. Ichihara, K. Retro-Diels-Alder strategy in natural product synthesis. Synthesis, 1987, 207-722.
103. Kamikubo, T; Hiroya, K; Ogasawara, K. Stereo-and enantio-controlled synthesis of two naturally occurring polyoxygenated cyclohexenemethanols, (+)-epiepoxydon and (-)-phyllostine, via catalytic asymmetrization of a meso substrate. Tetrahedron Lett., 1996 37, 499-502.
104. Kamikubo, T; Ogasawara, K. The enantiodivergent total synthesis of natural and unnatural enantiomers of theobroxide, Tetrahedron Lett., 1995 36, 1685-1688.
105. Kolwaski, T. Oak decline: I. Fungi associated with various disease symptoms on overground portions of middle-aged and old oak (Quercus robur L.),.Eur. J. Foren. Pathol., 1991 21, 136-151.
106. Kondru, RK; Lim, S; Wipf, P; Beratan, DN. Enantio/diastereoselective syntheses: synthetic and model computational studies of molar rotation additivity for interacting chiral centers: A reinvestigation of van't Hoff's principle Chirality 1997 9, 469-477.
107. Kondru, RK; Wipf, P; Beratan, DN. Theory-Assisted Determination of Absolute Stereochemistry for Complex Natural Products via Computation of Molar Rotation Angles, J. Am. Chem. Soc. 1998 120, 2204-2205.
108. Krohn, K; Bahramsari, R; Florke, U; Ludewig, K; Klichespory, C; Michel, A; Aust, H; Draeger, S; Schulz, B; Antus, S. Dihydroisocoumarins from fungi: isolation, structure elucidation, circular dichroism and biological activity, Phytochemistry, 1997 45, 313-320.
109. Kozikowski, AP; Lee, J. A synthesis approach to the cis-fused marine pyranopyrans, (3E)-and (3Z)-dactomylene. X-ray structure of a rare organomercurial, J. Org. Chem. 1990, 55, 863-870.
110. Langstrom, BO; Solheim, H, Hellqvist, C; Krokene, P. Host resistance in defoliated pine: effects of single and mass inoculations using bark beetle-associated blue-stain fungi Agric. and Forest Entomol., 2001 3, 211-216.
111. Leeuwenburgh, MA; Overkleeft, HS; Van der Marel, GA; Van Boom, JH. A novel approach towards cis-and trans-fused pyranopyrans based on ring-closing metathesis reaction of carbohydrate derivatives. Synlett., 1997 11, 1263-1264.
112. Linde, C; Kemp, GHJ. First report of Sphaeropsis canker on cypress in South Africa. Eur. J. Forest Pathol., 1997 27: 173-177.
113. Madar, Z; Solel, Z; Kimchi, M. Effect of water stress in cypress on the development of canker by Diplodia pinea f. sp. cupressi and Seiridium cardinale. Plant Disease, 1989 73, 484-486.
114. Madar, Z; Solel, Z; Kimchi, M. Pestalotiopsis canker of cypres in Israel. Phytoparasitica, 1991 19, 79-81.
115. Maddau, L; Ferracane, R; Franceschini, A, Cabras, A. Proceeding book of the National Congress-L'endofitismo di funghi e batteri patogeni in piante arboree e arbustive; Sassari-Tempio Pausania, Italy, 2002, pp 361-368.
116. Manitto, P. Biosynthesis of Natural Products. Chichester: Ellis Horwood Publishers; 1981; pp. 257-264.
117. Mason, SF. Theory. In Optical Rotatory Dispersion and Circular Dichroism in Organic Chemistry. Snatzke G editor. London: Wiley and Sons; 1967 Chapt. 4; pp. 71.
118. Mason, SF. Molecular Optical Activity and Chiral Discrimination; Cambridge: Cambridge University Press; 1982; pp. 273.
119. Marras, F; Franceschini, A; Maddau, L. IOBC/wprs Bulletin, 1995 18, 8-13.
120. McCrindle, R; Overton, KH. The Diterpenoids, Sesterterpenoids and Triterpenoids. In: Coffey S. editor. Rodd's Chemistry of Carbon Compounds. Amsterdam: Elsevier; 1969 II, pp. 369-403.
121. Mennucci, B; Claps M; Evidente A; Rosini, C. Absolute configuration of natural cyclohexene oxides by time dependent density functional theory calculation of the optical rotation: the absolute configuration of (-)-sphaeropsidone and (-)-epi-sphaeropsidone revised, J. Org. Chem., 2007 72, 6680-6691.
122. Mennucci, B; Tomasi, J; Cammi, JR; Cheeseman, JR; Frisch, MJ; Devlin, FJ; Gabriel, S; Stephens, PJ. Polarizable continuum model (PCM) calculations of solvent effects on optical rotations of chiral molecules, J. Chem. Phys. A., 2002 106, 6102-6113.
123. Miller, MW. The structure of terremutin, Tetrahedron, 1968 24, 4839-4851.
124. Miller, MW; Johnson, CR. Sonogashira coupling of 2-iodo-2-cycloalkenones: synthesis of (+)-and (-)-harveynone and (-)-tricholomenyn A. J. Org. Chem., 1997 62, 1582-1583.
125. Mirocha, CJ; DeVay, JE; Wilson, EE. Role of fumaric acid in the hull rot disease of almond, Phytopathology, 1961 51, 851-860.
126. Moreno-Manas, M; Pleixats, R. In Advances in Heterocyclic Chemistry. Katritzky, AR editor. San Diego, CA: Academic Press; 1992 53; pp. 1-84.
127. Mori, Y; Yaegashi, K; Furukawa, H. Oxiranyl anions in organic synthesis. Application to the synthesis of hemibrevetoxin B J. Am. Chem. Soc., 1997 119, 4557-4558.
128. Murrel, JN. The theory of electronic spectra of organic molecules; London: Methuen; 1963; pp. 248-254.
129. Nagasawa, H; Suzuki, A; Tamura, S. Isolation and structure of (+)deoxyepiepoxydon and (+)epiepxydon, phytotoxic fungal metabolites. Agric. Biol. Chem., 1978 42, 1303-1304.
130. Nakamori, K.; Matsuura, H.; Yoshihara, A.; Ichihara, A.; Koda, Y. Potato micro-tuber inducing substances from Lasidioplodia theobromae, Phytochemistry, 1994 35, 835-839.
131. Nakanishi, K.; Berova, N. In Circular Dichroism: Principles and Applications; Nakanishi K, Berova N, Woody RW editors. New York: VCH Publishers; 1994 Chapt.13; pp. 361.
132. Nakanishi, K; Berova, N. In Circular Dichroism: Principles and Applications; Nakanishi K, Berova N, Woody RW editors. New York: VCH Publishers; 2000 Chapt.12; pp. 337.
133. Nakanishi, K; Solomon, PH. Infrared Absorption Spectroscopy. In: 2nd Edn. edm Oakland: Holden Day Inc.; 1977; pp.17-44.
134. Noyes, RD; Hancock, JG. Role of oxalic acid in the Sclerotinia wilt of sunflower, Physiol. Plant Pathol., 1981 18, 123-132.
135. Palmer, MA; Stewart, EL; Wingfield, MJ. Variation among isolates of Sphaeropsis sapinea in the north central United States. Phytopathology, 1987 77, 944-948.
136. Parisi, A; Piattelli, M; Tringali, C; Magnano Di San Lio, G. Identification of the phytotoxin Mellein in culture fluids of Phoma tracheiphila, Phytochemistry, 1993 32, 865-867.
137. Pecul, M; Ruud, K. The Ab initio calculation of optical rotation and electronic circular dichroism. Adv. Quantum Chem. 2005 50, 185-212.
138. Peter, SW; Findlay; JA; Tam, WHJ. The X-ray crystal structure of (±)-flavipucine. Can. J. Chem, 1978 56, 1904-1906.
139. Pinon, J; Manion, PD. Hypoxylon mammatum and its toxins-recent advances in understanding their relationships with canker disease of poplar. Eur. J. For. Path., 1991 21, 202-209
140. Polavarapu, PL. Ab initio molecular optical rotations and absolute configurations. Mol. Phys. 1997a 91, 551-554.
141. Polavarapu, PL. Molecular optical rotations and structures. Tetrahedron: Asymm. 1997b 8, 3397-3401.
142. Polavarapu, PL; Chakraborty, DK. Absolute stereochemistry of chiral molecules from ab initio theoretical and experimental molecular optical rotations, J. Am. Chem. Soc. 1998 120, 6160-6164.
143. Polavarapu, PL. Optical rotation: Recent advances in determining the absolute configuration. Chirality, 2002 14, 768-781.
144. Porter, QN. Mass Spectrometry of Heterocyclic Compounds, New York: John Wiley & Sons; 1985; pp. 55-58, 262-266.
145. Pretsch, E; Bühlman, E; Affolter, C; Structure Determination of Organic Compound-Tables of Spectral Datas, Berlin: Springer; 2000; pp. 161-243, 385-404.
146. Rosenfeld, L. Z. Quantenmechanische Theorie der naturlichen optischen Aktivitat von Flussigkeiten und Gasen, Phys. 1928 52, 161-174.
147. Rosini, C; Zandomeneghi, M; Salvadori, P. Coupled oscillator calculations of circular dichroism intensities: structural applications in organic chemistry Tetrahedron Asymmetry 1993 4, 545-554.
148. Rudy, BC, Senkowski, BZ, Metipranolol [3,3-diethyl-5-methyl-2,4-piperidinedione]. Anal. Profile. Anal. Prof. Drug Sub. Excip., 1973 2, 363-382.
149. Sakamura, S; Nabeta, K; Yamada, S; Ichihara, A. Minor constituents from Phyllostica sp. and their correlation with epoxydon (phyllosinol). Agric. Biol. Chem., 1975 39, 403-407 (and references therein cited).
150. Scala, F; Evidente, A; Coppola, L; Capasso, R; Zoina, A. Identification and phytotoxicity of 3-methylthiopropanoic and trans-3-methylthiopropenoic acids produced in culture by Xanthomonas campestris pv. Vitians. J. Phytopathol., 1996 144, 325-329.
151. Scott, AI. Interpretation of the ultraviolet spectra of natural compounds. Oxford: Pergamon Press; 1964;.pp. 178-184.
152. Smith, DR; Stanosz, GR. Confirmation of two distinct populations of Sphaeropsis sapinea in the north central United States using RAPDs. Phytopathology, 1995 85, 699-704.
153. Solel, Z; Madar, Z; Kimchi, M; Golan, Y. Diplodia canker of cypress. Can. J. Plant Pathol., 1987 9, 115-118.
154. Sparapano, L; Bruno, G; Fierro, O; Evidente, A. Studies on structure-activity relationships of sphaeropsidins A-F, phytotoxins produced by Sphaeropsis sapinea f. sp. cupressi, Phytochemistry 2004 65, 189-198.
155. Sparapano, L; Evidente, A; Ballio, A; Graniti, A; Randazzo, G. New phytotoxic butenolides produced by Seiridium cardinale, the pathogen of cypress canker disease. Experientia, 1986 42, 627-628.
156. Stadler, M; Wollweber, H; Muhlbauer, A; Asakawa, Y; Hashimoto, T; Rogers, JD; Ju Yu-ming, Wetzstein, HG; Tichy, HV. Molecular chemotaxonomy of Daldinia and other Xylariaceae, Mycol. Res., 2001 105, 1191-1205.
157. Stanosz, GR; Smith, DR; Guthmiller, MA; Stanosz, JC. Persistence of Sphaeropsis sapinea on or in asymptomatic shoots of red and jack pines. Mycologia, 1997 89, 525-530.
158. Stanosz, GR; Swart, WJ; Smith, DR. Similarity between fungi identified as Diplodia pinea f. sp. cupressi in Israel and Botryosphaeria stevensii or Diplodia mutila on Juniperus in the United States. Eur. J. of Forest Patholm, 1998 28, 33-42
159. Stephens, PJ; Devlin, FJ; Cheeseman, JR; Frisch, MJ. Calculation of optical using. density functional theory. J. Phys. Chem. A, 2001 105, 5356-5371.
160. Stephens, PJ; Devlin, FJ; Cheeseman, JR; Frisch MJ. Ab initio prediction of optical rotation: comparison of density functional theory and Hartree-Fock methods for three 2,7,8-trioxabicyclo[3.2.1]octanes. Chirality, 2002 14, 288-96.
161. Stephens, PJ; Delvin FJ; Cheeseman, JR; Frisch, MJ; Bortolini, O; Besse, P. Determination of absolute configuration using ab initio calculation of optical rotation. Chirality, 2003 15, S57-S64.
162. Stephens, PJ; McCann, DM; Devlin, FJ, Butks, E; Stonclus, S; Cheeseman, JR. Determination of molecular structure using vibrational circular duchroism spectroscopy: the keto-lactone product of Baeyer-Villeger oxidation of (+)-(1R,5S)-bicyclo[3.3.1]nonane-2,7-dione. J. Org. Chem., 2005 70, 39013-3913.
163. Stephens, PJ; McCann, DM; Devlin, FJ; Cheeseman, JR; Frisch, MJ. Determination of the absolute configuration of [3(2)](1,4)barrelenophanedicarbonitrile using concerted time-dependent density functional theory calculations of optical rotation and electronic circular dichroism. J. Am. Chem. Soc., 2004 126, 7514-7521.
164. Sternhell, S. Correlation of interproton spin-spin coupling constants with structure. Quarterly Review, 1969 23, 236-270.
165. Strobel, GA. Phytotoxins. Ann, Rev. Biochem., 1982 51, 309-333.
166. Superchi, S; Giorgio, E; Rosini, C. The enantioselectivity of this process is mainly dependent on the chiral. Chirality, 2004 69, 2532-2543.
167. Swart, WJ; Wingfield, MJ. Biology and control of Sphaeropsis sapinea on Pinus species in South Africa. Plant Dis., 1991 75, 761-766.
168. Swart, WJ; Wingfield, MJ; and Grant, WS. Comparison of Sphaeropsis sapinea and Sphaeropsis sapinea f. sp. cupressi. Mycol Res., 1993 97, 1253-1260.
169. Sutton, BC. Sphaeropsis sapinea. In: Coelomycetes. Kew, Surrey, UK: Commonwealth Mycological Institute, Inst/assoc. Appl. Biol., 1980, 120-121.
170. Tabacchi, R. Secondary phytotoxic metabolites from phytopathogenic fungi-structure, stnthesis and activity. Pure Appl. Chem., 1994 66, 2299-2302.
171. Tachihara, T; Kitahara, T. Total synthesis of (+)-epiepoformin, (+)-epiepoxydon and (+)-bromoxone employing a useful chiral building block, ethyl (1R,2S)-5,5-ethylenedioxy-2-hydroxycyclohexanecarboxylate. Tetrahedron, 2003, 59 1773-1780.
172. Takeshi, K; Miyako, F; Toshiyuki, H; Tominari, C; Junko, N; Yukio, O; Satoshi, H. The absolute configuration of (+)-oxopropaline D by theoretical calculation of specific rotation and asymmetric synthesis. Chem. Pharm. Bull., 2003 51, 20-23.
173. Thomson, RH. The Chemistry of Natural Products. Glasgow: Blackie; 1985; pp. 107-153s.
174. Turner, WB; Aldridge, DC. Fungal Metabolites II, London: Academic Press; 1983 pp. 62-66 228-280, 370-383, 398-399, 468-484, 505, 530-532, 631.
175. Upadhyay, RK; Mukerji, KG. Toxins in Plant Disease Development and Evolving Biotechnology, New Delhi: Oxford & IBH Publishing Co. Pvt. Ltd.; 1997; pp. 167.
176. Uspenskaya, GA; Reshetnikova, IA. On toxins produced by sphaeropsidal fungi. Mikologjia i Fitopatologia, 1975 9, 355-357.
177. Vurro, M; Bottalico, A; Capasso, R; Evidente, A. Cytocalasins from phytopathogenic Ascochita and Phoma species. In: Upahyay RK, Mukerji KG editors. Toxins in Plants Disease Development and Evolving Biotechnology., New Delhi: Oxford & IBH publishing Co. Pvt. Ltd.; 1997; pp. 127-147.
178. Venkatasubbaiah, P; Chilton, WS. Phytotoxins of Botryosphaeria obtuse. J. Nat. Prod., 1990 53, 1628-1630.
179. Venkatasubbaiah, P; Sutton, TB; Chilton, WS. Effect of phytotoxins produced by Botryosphaeria obtusa, the cause of black rot of apple fruit and frogeye leaf spot. Phytopathology, 1991 81, 243-247.
180. Vogensen, SB; Greenwood, J R; Varmin, AR; Brehm, L; Pickering, DS; Nielsen, B; Liljefors, T; Clausen, RP; Johansen, TN; Krogsgaard-Larsen, P. Stereochemical anomaly: the cyclised (R)-AMPA analogue (R)-3-hydroxy-4,5,6,7-tetrahydroisoxazolo[5,4-c]pyridine-5-carboxylic acid [(R)-5-HPCA] resembles (S)-AMPA at glutamate receptors. Org. Biomol. Chem., 2004 2, 206-213.
181. Wagener, WW. The canker of Cupressus induced by Coryneum cardinale n. sp. J. Agric. Res., 1939 58, 1-46.
182. Wang, CG; Blanchette, RA; Palmer, MA. Differences in conidial morphology among South African isolates of Sphaeropsis sapinea. Plant Dis., 1985 69, 838-841.
183. Whalley, AJS; Edwards, RL. Secondary metabolites and systematic arrangement within the Xylariaceae. Can J. Bot., 1995 73, 5802-5810
184. White, PS; Findalay, JA; Wah Hung, J. The X-ray crystal structure of (±)-flavipucine. Can. J. Chem., 1978 56, 1904-1906.
185. Xenopoulos, S. A new for Greece pathogen causing the cypress canker disease. Dasike Eurena, 1987 2, 85-94.
186. Xenopoulos, S; Tsopelas, P. Sphaeropsis canker, a new disease of cypress in Greece. Forest Pathol., 2000 30, 121-126.
187. Zwolinski, JB; Swart, WJ; Wingfield, M. Economic impact of a post-hail outbreak of dieback induced by Sphaeropsis sapinea. Eu. J. Forestry and Pathol., 1990 20, 405-411