Fungistatic activity of bicyclo[4.3.0]-γ-lactones

Journal of Agricultural and Food Chemistry

Volumn 59, Issue 11, 2011, Pages 6071-6081

  Olejniczak, Teresa ^a   Boratyński, Filip ^a   Białońska, Agata ^b  

^a WROC AW UNIVERSITY OF ENVIRONMENTAL AND LIFE SCIENCES   (Poland)

^b UNIVERSITY OF WROC AW   (Poland)

Author keywords

Fusarium culmorum; Fusarium oxysporum; HLADH; IC50; lactones

Indexed keywords

FUSARIUM CULMORUM; FUSARIUM OXYSPORUM; HLADH; IC50; LACTONES;

ANTIFUNGAL AGENT; LACTONE;

ARTICLE; ASPERGILLUS; CHEMICAL STRUCTURE; CHEMISTRY; DRUG EFFECT; FUSARIUM; SYNTHESIS;

ANTIFUNGAL AGENTS; ASPERGILLUS; FUSARIUM; LACTONES; MOLECULAR STRUCTURE;

ASPERGILLUS OCHRACEUS; FUSARIUM CULMORUM; FUSARIUM OXYSPORUM; FUSARIUM TRICINCTUM;

EID: 79957984251     PISSN: 00218561     EISSN: 15205118     Source Type: Journal    
DOI: 10.1021/jf105019u     Document Type: Article

References (44)

1. Namakura, Y.; Xu, X.; Saito, Y.; Tateishi, T.; Takahashi, T.; Kawachi, Y.; Ostuka, F. Deep cutaneous infection by Fusarium solani in a healthy child: Successful treatment with local heat therapy J. Am. Acad. Dermatol. 2007, 56 (5) 873-877 (Pubitemid 46560999)
2. Gilroy, S. A.; Roller, J.; Rawling, R. A.; Granto, P. A. Disseminated fusariosis: an emerging opportunistic infection Clin. Microbiol. 2006, 28, 153-157
3. Tomee, J. F. Ch.; Van der Werf, T. S. Pulmonary aspergillosis Neth. J. Med. 2001, 59, 244-258 (Pubitemid 33035012)
4. Malo, J. L. Antifungal therapy for allergic bronchopulmonary aspergillosis J. Allergy Clin. Immunol. 2003, 111, 934-935
5. Prieto-Simon, B.; Noguer, T.; Campas, M. Emerging biotools for assessment of mycotoxins in the past decade Trends Anal. Chem. 2007, 7, 698-702
6. Martino, P. Clinical patterns of Fusarium infections in immunocopromised patients J. Infect. 1994, 28, 7-15
7. Legzdina, L.; Buerstmayr, B. Comparison of infection with Fusarium head blight and accumulation of mycotoxins in grain of hulless and covered barley J. Cereal Sci. 2004, 40, 61-67 (Pubitemid 38851965)
8. Champeil, A.; Dore, T.; Courbet, J. F. Fusarium Head blight: epidemiological origin of the effects of cultural practices on head blight attacks and the production of mycotoxins by Fusarium in wheat grains Plant Sci. 2004, 166, 1389-1415 (Pubitemid 38511758)
9. Koch, H. J.; Pringas, Ch.; Maerlaender, B. Evaluation of environmental and management effects on Fusarium head blight infection and deoxynivalenol concentration in the grain of winter wheat Eur. J. Agron. 2006, 24, 357-366
10. Palazzini, J. M.; Ramirez, M. L.; Torres, A. M.; Chulze, S. N. Potential biocontrol agents for Fusarium head blight and deoxynivalenol production in wheat Crop Prot. 2007, 26, 1702-1710 (Pubitemid 47496184)
11. Elmer, W. H. Effects of acibenzolar-S-methyl on the suppression of Fusarium wilt of cyclamen Crop Prot. 2006, 25, 671-676
12. Elmer, W. H.; McGovern, R. J. Efficacy of integrating biologicals with fungicides for the suppression of Fusarium wilt of cyclamen Crop Prot. 2004, 23, 909-914 (Pubitemid 39027274)
13. Blaney, B. J.; Dodman, R. L. Production of zeralenone, deoxynivalenol, nivalenol, and acetylated derivated by Australian isolates of Fusarium graminearum and Fusarium pseudograminearum in relation to source and culturing conditions Aust. J. Agric. Res. 2002, 53, 1317-1326 (Pubitemid 36093240)
14. Blandino, M.; Minelli, L.; Reyneri, A. Strategies for the chemical control of Fusarium head blight: Effect on yield, alveographic parameters and deoxynivalenol contamination in winter wheat grain Eur. J. Agron. 2006, 25, 193-201 (Pubitemid 44397605)
15. Cooke, R. C.; Van Leeuwen, K. A.; Capone, D.; Gawel, R.; Elsey, G. M.; Sefton, M. A. Odor detection thresholds and enantiomeric distributions of several 4-alkyl substituted γ-lactones in Australian red wine J. Agric. Food Chem. 2009, 57, 2462-2467
16. Erasto, P.; Grierson, D. S.; Afllayan, A. J. Bioactive sesquiterpene lactones from leaves of Vernonia amygdalina J. Ethnopharmacol. 2006, 106, 117-120
17. Mangnus, E. M.; Zwanenburg, B. Synthesis, structural characterization and biological evaluation of all four enantiomers of strigol analog GR7 J. Agric. Food Chem. 1992, 40, 697-700
18. Macias, F. A.; Simmonet, A. M.; Pacheco, P. C.; Barrero, A. F.; Caberea, E.; Jimenez-Gonzalez, D. Natural synthesis jodolactones with potential use as natural herbicides models J. Agric. Food Chem. 2000, 48, 3003-3007 (Pubitemid 30490528)
19. Frank, O.; Blumberg, S.; Krumpel, G.; Hofmann, T. Structure determination f 3-O-caffeoyl-epi-γ-quinide an orphan bitter lactones in roasted coffee J. Agric. Food Chem. 2008, 56, 9581-9585
20. Yamamoto, T.; Ogura, M.; Amano, A.; Adachi, K.; Hagiwara, T.; Kanisawa, T. Synthesis and odor of optically active 2- n -hexyl- and 2-n- heptylcyclopentanone and the corresponding δ-lactones Tetrahedron Lett. 2002, 43, 9081-9084 (Pubitemid 35305074)
21. Mosandl, A.; Gunther, C. Stereoisomeric flavor compounds. 20. Structure and properties of γ-lactone enantiomers J. Agric. Food Chem. 1989, 37, 413-418
22. Barrero, A. F.; Oltra, J. E.; Alverez, M.; Raslan, D. S.; Saude, D. A.; Assikra, M. New sources and antifungal activity of sesquiterpene lactones Fitoterapia 2000, 71, 60-64 (Pubitemid 30012019)
23. Evidente, A.; Cabras, A.; Maddau, L.; Serra, S.; Andolfi, A.; Motta, A. Vididepyrone A. New antifungal 6-substituted 2H-pyran-2-one produced by Trichoderma viride J. Agric. Food Chem. 2003, 51, 6957-6960
24. Cabedo, N.; Lopez-Gresa, M. P.; Primo, J.; Ciavatta, M. L.; Gonzalez-Mas, M. C. Isolation and structural elucidation of eight new related analogues of mycotoxin (-)-Botryodiplodin from Penicillium coalescens J. Agric. Food Chem. 2007, 55, 6977-6983 (Pubitemid 47338935)
25. Neerman, M. F. Sesquiterpene lactones: A diverse class of compounds found in essential oils possessing antibacterial and antifungal properties Int. J. Aromather. 2003, 13, 114-120 (Pubitemid 37210017)
26. Min, B. S.; Lee, S. Y.; Kim, J. H.; Kwon, O. K.; Park, B. Y.; An, R. B.; Lee, J. K.; Moon, H. I.; Kim, T. J.; Kim, Y. H.; Joung, H.; Lee, H. K. Lactones from the leaves of Litsea japonica and their anti-complement activity J. Nat. Prod. 2003, 66, 1388-1390 (Pubitemid 37323410)
27. Momin, R. A.; Nair, M. G. Antioxidant cyclooxygenase and topoisomerase inhibitory compounds from Apium graveolens Linn. Seeds Phytomedicine 2002, 9, 312-318 (Pubitemid 34712502)
28. Djeddi, S.; Karioti, A.; Sokovic, M.; Koukoulitsa, C.; Skaltsa, H. A novel sesquiterpene lactone from Centaurea pullata: structure elucidation, antimicrobial activity and prediction of pharmacokinetic properties Bioorg. Med. Chem. 2008, 16, 3725-3731 (Pubitemid 351506439)
29. Skaltsa, H.; Lazari, D.; Panagouleas, C.; Georgiadou, E.; Garcia, B.; Sokovic, M. Sesquiterpene lactones from Centaurea thessala and Centaurea attica. Antifungal activity Phytochemistry 2000, 55 (8) 903-908
30. Euzebio, F. P. G.; dos Santos, F. J. L.; Pilo-Veloso, D.; Ruiz, A. L. T. G.; de Carvalho, J. E.; Ferreira-Alves, D. L.; de Fatima, A. Effect of 6α,7β-dihydroxyvouacapan-17β-oic acid and its lactone derivatives on the growth of human cancer cells Bioorg. Chem. 2009, 37, 96-100
31. Bonini, C.; Righi, G. A critical outlook and comparison of enantioselective oxidation methodologies of olefins Tetrahedron 2002, 58, 4981-5021 (Pubitemid 34634189)
32. Paruch, E.; Ciunik, Z.; Nawrot, J.; Wawrzeńczyk, C. Lactones 9. Synthesis of terpenoid lactones-active insect antifeedants J. Agric. Food Chem. 2000, 48, 4973-4977
33. Szczepanik, M.; Olejniczak, T.; Jurków, K. Feeding deterrent activity of bicyclic lactones obtained from anhydrides of amber- and glutaric acid against colorado potato beetle, (Leptinotarsa decemlineata say) Prog. Plant Prot. 2008, 48 (2) 742-746
34. Wawrzeńczyk, C.; Dams, I.; Szumny, A.; Szczepanik, M.; Nawrot, J.; Pra̧dzyńska, A.; Gabryś, B.; Dancewicz, K.; Magnucka, E.; Gawdzik, B.; Obara, R.; Wzorek, A. Synthesis and evaluation of antifeedant, antifungal and antibacterial activity of isoprenoid lactones Pol. J. Environ. Stud. 2005, 14 (Suppl. II) 69-84
35. Beck, J. J.; Chou, S. C. The structural diversity of phthalides from the Apiaceae J. Nat. Prod. 2007, 70, 891-900 (Pubitemid 46953624)
36. Momin, R. A.; Nair, M. G. Mosquitocidal, nematicidal and antifungal compounds from Apium graveolens L. Seeds J. Agric. Food Chem. 2001, 49, 142-145 (Pubitemid 32104502)
37. Lescop, C.; Nguyen-Kim, P. P; Huet, F. Stereolective synthesis of a [3.3.0]-fused γ-butyrolactone. Application in the preparation of bicyclic nucleosides Tetrahedron Lett. 2000, 3057-3060 (Pubitemid 30256739)
38. McCluskey, A.; Ackland, S. P.; Bowyer, M. C.; Baldwin, M. L.; Garner, J.; Walkom, C. C.; Sakoff, J. A. Cantharidin analogues: synthesis and evaluation of growth inhibition in a panel of selected tumour cell lines Bioorg. Chem. 2003, 31, 68-79 (Pubitemid 36411927)
39. Pour, M.; Spulak, M.; Buchta, V.; Kubanova, P.; Voprsalova, M.; Wsól, V.; Fakova, H.; Koudelka, P.; Pourova, H.; Schiller, R. 3-Phenyl-5-acyloxymethyl-2H,5H-furan-2-ones: Synthesis and biological activity of a novel group of potential antifungal drugs J. Med. Chem. 2001, 44, 2701-2706 (Pubitemid 32879712)
40. Sheldrick, G. M. A short history of SHELX Acta Crystallogr., Sect. A 2008, 64, 112-122
41. Jakovic, I. J.; Goodbrand, H. B.; Lok, K. P.; Jones, J. B. Enzymes in organic synthesis. 24. Preparations of enantiomerically pure chiral lactones via stereospecific horse liver alcohol dehydrogenase catalyzed oxidations of monocyclic meso diols J. Am. Chem. Soc. 1982, 104, 4659-4665
42. Edelsbacher, A.; Urban, E.; Wiedenauer, W. Preparation of Enantiomerically Pure 5,6-dihydroxy-iso-benzofuranones and 5,6-dihydroxy-4,7- methano-isobenzofuranones Monatsh. Chem. 1992, 123, 741-747
43. Stejskal, R.; Urban, E. Vollenkle Synthese und Konfigurationszuordnung von potentiell antimikrobiellen 5,6-dihydroxyisobenzofuranonen Monatsh. Chem. 1991, 122, 145-156
44. Canonne, P.; Forcolos, G. B.; Belanger, D. One-step annelation. A convenient method for the preparation of diols, spirolactones, and spiroethers from lactones J. Org. Chem. 1980, 45, 1828-1835