Abstract
The light-induced singlet oxygen production and antifungal activity of phenylphenalenone phytoalexins isolated from infected banana plants (Musa acuminata) are reported. Upon absorption of light energy all studied phenylphenalenones sensitise the production of singlet oxygen in polar and non-polar media. Antifungal activity of these compounds towards Fusarium oxysporum is enhanced in the presence of light. These results, together with the correlation of IC50 values under illumination with the quantum yield of singlet oxygen production and the enhancing effect of D2O on the antifungal activity, suggest the intermediacy of singlet oxygen produced by electronic excitation of the phenylphenalenone phytoalexins.
Similar content being viewed by others
References
J. F. Dangl, J. D. G. Jones, Plant pathogens and integrated defence responses to infection, Nature, 2001, 411, 826–833.
P. M. Waterhouse, M.-B. Wang, T. Lough, Gene silencing as an adaptive defence against viruses, Nature, 2001, 411, 834–842.
R. A. Dixon, Natural products and plant disease resistance, Nature, 2001, 411, 843–847.
E. Lam, N. Kato, M. Lawton, Programmed cell death, mitochondria and the plant hypersensitive response, Nature, 2001, 411, 848–853.
E. E. Farmer, Surface-to-air signals, Nature, 2001, 411, 854–856.
M. D. Rauscher, Co-evolution and plant resistance to natural enemies, Nature, 2001, 411, 857–864.
M. H. Stuiver, J. H. H. V. Custers, Engineering disease resistance in plants, Nature, 2001, 411, 865–868.
H. D. van Etten, J. W. Mansfield, J. A. Bailey, E. E. Farmer, Two classes of plant antibiotics: phytoalexins versus phytoanticipins, Plant Cell, 1994, 1191–1192.
K. R. Downum, Light activated plant defence, New.Phytol., 1992, 122, 401–420.
M. Berenbaum, Phototoxicity of plant secondary metabolites: insect and mammalian perspectives, Arch. Insect Biochem Physiol., 1995, 29, 119–134.
K. R. Downum, J. Wen, The occurrence of photosensitizers among higher plants, ACS Symp. Ser., 1995, 616, Light-Activated Pest Control 135–143.
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.
J. P. Knox, A. D. Dodge, Singlet oxygen in plants, Phytochemistry, 1985, 24, 889–896.
M. R. Berenbaum, R. A. Larson, Flux of singlet oxygen from leaves of phototoxic plants, Experientia, 1988, 44, 1030–1032.
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.
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.
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.
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.
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.
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.
N. Hirai, H. Ishida, K. Koshimizu, A phenalenone-type phytoalexin from Musa acuminata, Phytochemistry, 1994, 37, 383–385.
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.
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.
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.
T. Kamo, N. Hirai, K. Iwami, D. Fujioka, H. Ohigashi, New phenylphenalenones from banana fruit, Tetrahedron, 2001, 57, 7649–7656.
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.
R. Schmidt, C. Tanielian, R. Dunsbach, C. Wolff, Phenalenone, a universal reference compound for the determination of quantum yields of singlet oxygen O2(1Δg) sensitization, J. Photochem. Photobiol. A: Chem., 1994, 79, 11–17.
C. Martí, O. Jürgens, O. Cuenca, M. Casals, S. Nonell, Aromatic ketones as standards for singlet molecular oxygen O2(1Δg) photosensitization. Time-resolved photoacoustic and NIR emission studies, J. Photochem. Photobiol. A: Chem., 1996, 97, 11–18.
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.
G. Cilento, Generation of electronically excited triplet species in biochemical systems, Pure Appl. Chem., 1984, 56, 1179–1190.
R. G. Cooke, J. M. Edwards, Naturally occurring phenalenones and related compounds, Prog. Chem. Org. Nat. Prod., 1981, 40, 153–190.
J. M. Kornfeld, J. M. Edwards, An investigation of the photodynamic pigments in extracts of Lachnantes tinctoria, Biochim. Biophys. Acta, 1972, 286, 88–90.
C. Darwin, The Origin of Species, Encyclopaedia Britannica, Chicago, IL, 6th edn., 1952.
D. F. Eaton, in Handbook of Organic Photochemistry, ed. J. C. Scaiano. CRC Press, Boca Raton, FL, 1989, vol. 1, pp. 231–239.
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.
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.
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.
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.
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.
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.
R. J. Grayer, J. B. Harborne, A survey for antifungal compounds from higher plants, Phytochemistry, 1994, 37, 19–42.
C. Schweitzer, R. Schmidt, Physical mechanisms of generation and deactivation of singlet oxygen, Chem. Rev., 2003, 103, 1685–1757.
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.
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.
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.
Author information
Authors and Affiliations
Corresponding author
Rights and permissions
About this article
Cite this article
Lazzaro, A., Corominas, M., Martí, C. et al. Light- and singlet oxygen-mediated antifungal activity of phenylphenalenone phytoalexins. Photochem Photobiol Sci 3, 706–710 (2004). https://doi.org/10.1039/b401294a
Received:
Accepted:
Published:
Issue Date:
DOI: https://doi.org/10.1039/b401294a