Light- and singlet oxygen-mediated antifungal activity of phenylphenalenone phytoalexins

Photochemical and Photobiological Sciences

Volumn 3, Issue 7, 2004, Pages 706-710

  Lazzaro, Alejandra ^b   Corominas, Montserrat ^a   Martí, Cristina ^a   Flors, Cristina ^a   Izquierdo, Laura R ^b   Grillo, Teresa A ^b   Luis, Javier G ^b   Nonell, Santi ^a  

^a INSTITUT QUÍMIC DE SARRIÀ   (Spain)

^b UNIVERSIDAD DE LA LAGUNA   (Spain)

Author keywords

[No Author keywords available]

Indexed keywords

ANTIFUNGAL AGENT; PHYTOALEXINS; PLANT EXTRACT; SINGLET OXYGEN; TERPENE; DEUTERIUM OXIDE; PHENYLPHENALENONE PHYTOALEXIN DERIVATIVE; PLANT TOXIN; UNCLASSIFIED DRUG;

ARTICLE; CHEMICAL STRUCTURE; CHEMISTRY; FRUIT; FUSARIUM; ISOLATION AND PURIFICATION; LIGHT; PHOTOCHEMISTRY; RADIATION EXPOSURE; ANTIFUNGAL ACTIVITY; BANANA; BIOSYNTHESIS; CONTROLLED STUDY; CORRELATION ANALYSIS; ELECTRONICS; ENERGY ABSORPTION; FUNGAL PLANT DISEASE; FUSARIUM OXYSPORUM; IC 50; ILLUMINATION; ISOLATION PROCEDURE; LIGHT ABSORPTION; NONHUMAN; PHOTOREACTIVITY; PHOTOSENSITIZATION; POLARIZATION; PRIORITY JOURNAL; QUANTUM YIELD;

ANTIFUNGAL AGENTS; FRUIT; FUSARIUM; LIGHT; MOLECULAR STRUCTURE; PHOTOCHEMISTRY; PLANT EXTRACTS; SINGLET OXYGEN; TERPENES;

FUSARIUM; FUSARIUM OXYSPORUM; MUSA; MUSA ACUMINATA;

EID: 4344596904     PISSN: 1474905X     EISSN: 14749092     Source Type: Journal    
DOI: 10.1039/b401294a     Document Type: Article

References (45)

1. J. F. Dangl J. D. G. Jones Plant pathogens and integrated defence responses to infection Nature 2001 411 826-833.
2. P. M. Waterhouse M.-B. Wang T. Lough Gene silencing as an adaptive defence against viruses Nature 2001 411 834-842.
3. R. A. Dixon Natural products and plant disease resistance Nature 2001 411 843-847.
4. E. Lam N. Kato M. Lawton Programmed cell death, mitochondria and the plant hypersensitive response Nature 2001 411 848-853.
5. E. E. Farmer Surface-to-air signals Nature 2001 411 854-856.
6. M. D. Rauscher Co-evolution and plant resistance to natural enemies Nature 2001 411 857-864.
7. M. H. Stuiver J. H. H. V. Custers Engineering disease resistance in plants Nature 2001 411 865-868.
8. H. D. vanEtten J. W. Mansfield J. A. Bailey E. E. Farmer Two classes of plant antibiotics: phytoalexins versus phytoanticipins Plant Cell 1994 1191-1192.
9. K. R. Downum Light activated plant defence New.Phytol. 1992 122 401-420.
10. M. Berenbaum Phototoxicity of plant secondary metabolites: insect and mammalian perspectives Arch. Insect Biochem Physiol. 1995 29 119-134.
11. K. R. Downum J. Wen The occurrence of photosensitizers among higher plants ACS Symp. Ser. 1995 616 Light-Activated Pest Control 135-143.
12. G. H. N. Towers J. E. Page J. B. Hudson Light-mediated biological activities of natural products from plants and fungi Curr. Org. Chem. 1997 1 395-414.
13. J. P. Knox A. D. Dodge Singlet oxygen in plants Phytochemistry 1985 24 889-896.
14. M. R. Berenbaum R. A. Larson Flux of singlet oxygen from leaves of phototoxic plants Experientia 1988 44 1030-1032.
15. J. G. Luis F. Echeverri W. Quiñones I. Brito M. López F. Torres G. Cardona Z. Aguilar C. Peláez M. Rojas Irenolone and emelonone: two new types of phytoalexin from Musa paradisiaca J. Org. Chem. 1993 58 4306-4308.
16. J. G. Luis W. Q. Fletcher F. Echeverri T. A. Grillo Phenalenone-type phytoalexins form Musa acuminata. Synthesis of 4-phenyl-phenalenones Tetrahedron 1994 50 10963-10970.
17. J. G. Luis W. Q. Fletcher F. Echeverri T. Abad M. P. Kishi A. Perales New Phenalenone-type phytoalexins from Musa acuminata(colla AAA) grand nain Nat. Prod. Lett. 1995 6 23-30.
18. J. G. Luis W. Quiñones F. Echeverri T. A. Grillo M. P. Kishi F. Garcia-Garcia F. Torres G. Cardona Musanolones: four 9-phenylphenalenones from rhizomes of Musa acuminata Phytochemistry 1996 41 753-757.
19. J. G. Luis E. H. Lahlou L. S. Andres F. Echeverri W. Q. Fletcher Phenylphenalenonic phytoanticipins. New acenaphthylene and dimeric phenylphenalenones from the resistant Musa selected hybrid SH-3481 Tetrahedron 1997 53 8249-8256.
20. T. Kamo N. Kato N. Hirai M. Tsuda D. Fujioka H. Ohigashi Phenylphenalenone-type phytoalexins from unripe Bungulan banana fruit Biosci. Biotechnol. Biochem. 1998 62 95-101.
21. N. Hirai H. Ishida K. Koshimizu A phenalenone-type phytoalexin from Musa acuminata Phytochemistry 1994 37 383-385.
22. W. Quiñones G. Escobar F. Echeverri F. Torres Y. Rosero V. Arango G. Cardona A. Gallego Synthesis and antifungal activity of Musa phytoalexins and structural analogs Molecules 2000 5 974-980.
23. J. G. Luis W. Q. Fletcher F. Echeverri T. A. Grillo A. Perales J. A. González Intermediates with biosynthetic implications in de novo production of phenyl-phenalenone-type phytoalexins by Musa acuminata. Revised structure of emenolone Tetrahedron 1995 51 4117-4130.
24. R. H. Binks J. R. Greenham J. G. Luis S. R. Gowen Phytoalexin production in Musa acuminata AA ‘Pisang Jari Buaya’ Group Var. Pisang Sipulu after invasion from plant parasitic nematodes Phytochemistry 1997 45 47-49.
25. T. Kamo N. Hirai K. Iwami D. Fujioka H. Ohigashi New phenylphenalenones from banana fruit Tetrahedron 2001 57 7649-7656.
26. E. Oliveros P. Suardi-Muraseco T. Aminian-Saghafi A. M. Braun H.-J. Hansen 1H-Phenalen-1-one: Photophysical properties and singlet-oxygen production Helv. Chim. Acta 1991 74 79-90.
27. g) sensitization J. Photochem. Photobiol. A: Chem. 1994 79 11-17.
28. g) photosensitization. Time-resolved photoacoustic and NIR emission studies J. Photochem. Photobiol. A: Chem. 1996 97 11-18.
29. M. P. De Mello A. L. Nascimento C. Bohne G. Cilento Excitation of chloroplasts in Euglena gracilis in the absence of light Photochem. Photobiol. 1988 47 457-461.
30. G. Cilento Generation of electronically excited triplet species in biochemical systems Pure Appl. Chem. 1984 56 1179-1190.
31. R. G. Cooke J. M. Edwards Naturally occurring phenalenones and related compounds Prog. Chem. Org. Nat. Prod. 1981 40 153-190.
32. J. M. Kornfeld J. M. Edwards An investigation of the photodynamic pigments in extracts of Lachnantes tinctoria Biochim. Biophys. Acta 1972 286 88-90.
33. C. Darwin, The Origin of Species, Encyclopaedia Britannica, Chicago, IL, 6th edn., 1952.
34. D. F. Eaton, in Handbook of Organic Photochemistry, ed. J. C. Scaiano. CRC Press, Boca Raton, FL, 1989, vol. 1, pp. 231–239.
35. M. Resende J. Flood J. Ramsden M. Beale R. Cooper Novel phytoalexins including elemental sulfur in the resistance of cocoa (Theobrama cacao L.) to verticillium wilt (Verticillium dahliae kleb.) Physiol. Mol. Plant Pathol. 1996 48 347-359.
36. P. Sarig Y. Zutkhi A. Monjauze N. Lisker R. Ben-Arie Phytoalexin elicitation in grape berries and their susceptibility to Rhyzopus stolonifer Physiol. Mol. Plant Pathol. 1997 50 337-347.
37. G. Chilosi C. Caruso C. Caporale C. Leonardi L. Bertini A. Buzi M. Nobile P. Magro V. Buonocore Antifungal activity of a Bowman-birk-like trypsin inhibitor from wheat kernel J. Phytopathol. 2000 148 477-481.
38. J. Ritter H.-U. Borst T. Lindner M. Hauser S. Brosig K. Bredereck U. E. Steiner D. Kühn J. Kelemen H. E. A. Kramer Substituent effects on triplet yields in aminoanthraquinones: radiationless deactivation via intermolecular and intramolecular hydrogen bonding J. Photochem. Photobiol. A: Chem. 1988 41 227-244.
39. M. L. Pierce E. C. Cover P. E. Richardson V. E. Scholes M. Essenberg Adequacy of cellular phytoalexin concentrations in hypersensitively responding cotton leaves Physiol. Mol. Plant Pathol. 1996 48 305-324.
40. S. Lo I. Weiergang C. Bonham J. Hipskind K. Wood R. Nicholson Phytoalexin accumulation in sorghum: identification of a methyl ether of luteonilidin Physiol. Mol. Plant Pathol. 1996 49 21-31.
41. R. J. Grayer J. B. Harborne A survey for antifungal compounds from higher plants Phytochemistry 1994 37 19-42.
42. C. Schweitzer R. Schmidt Physical mechanisms of generation and deactivation of singlet oxygen Chem. Rev. 2003 103 1685-1757.
43. J. Bakker F. J. Gommers L. Smits A. Fuchs F. W. de Vries Photoactivation of the nematicidal compound α-terthienyl from roots of marigolds (Tagetes species) Photochem. Photobiol. 1983 38 323-329.
44. T. J. Sun U. Melcher M. Essenberg Inactivation of cauliflower mosaic virus by a photoactivatable cotton phytoalexin Physiol. Mol. Plant Pathol. 1988 33 115-126.
45. E. Kourany J. T. Arnason E. Schneider Accumulation of phototoxic thiophenes in Tagetes erecta(Asteraceae) elicited by Fusarium oxysporum Physiol. Mol. Plant Pathol. 1988 33 287-297.