On the mode of action of the phytotoxin (8R,16R)-(-)-pyrenophorin

Pesticide Biochemistry and Physiology

Volumn 86, Issue 1, 2006, Pages 7-14

  Aliferis, Konstantinos A ^a   Chrysayi Tokousbalides, Maria ^a  

^a AGRICULTURAL UNIVERSITY OF ATHENS   (Greece)

Author keywords

Avena sterilis; Bleaching; Macrodiolides; Mode of action; Oxidative stress; Phytotoxin; Pyrenophorin; Superoxide dismutase

Indexed keywords

AVENA STERILIS;

EID: 33746727573     PISSN: 00483575     EISSN: 10959939     Source Type: Journal    
DOI: 10.1016/j.pestbp.2005.11.011     Document Type: Article

References (66)

1. Daub M.E., and Hangarter R.P. Light-induced production of singlet oxygen and superoxide by the fungal toxin, cercosporin. Plant Physiol. 73 (1983) 855-857
2. Stonard R.J., and Miller-Wideman M.A. Herbicides and plant growth regulators. In: Godfrey C.R.A. (Ed). Agrochemicals from Natural Products (1995), Marcel Dekker Inc., New York 285-310
3. Lange L., and Lopez C.S. Micro-organisms as a source of biologically active secondary metabolites. In: Copping L.G. (Ed). Crop Protection Agents from Nature. Natural Products and Analogues (1996), The Royal Society of Chemistry, Cambridge 1-26
4. Miana G.A., Rahman A.U., Choudhary M.I., Jilani G., and Bibi H. Part III: pesticides from nature: present and future perspectives. In: Copping L.G. (Ed). Crop Protection Agents from Nature. Natural Products and Analogues (1996), The Royal Society of Chemistry, Cambridge 241-253
5. Dayan F.E., Romagni J.G., and Duke S.O. Investigating the mode of action of natural phytotoxins. J. Chem. Ecol. 26 9 (2000) 2079-2094
6. Duke S.O., Romagni J.G., and Dayan F.E. Natural products as sources for new mechanisms of herbicidal action. Crop Prot. 19 (2000) 583-589
7. Bartlett D.W., Clough J.M., Godwin J.R., Hall A.A., Hamer M., and Parr-Dobrzanski B. The strobilurin fungicides. Pest Manag. Sci. 58 (2002) 649-662
8. Duke S.O., Dayan F.E., Rimando A.M., Schrader K.K., Aliotta G., Oliva A., and Romagni J.G. Chemicals from nature for weed management. Weed Sci. 50 (2002) 138-151
9. Heiser I., Sachs E., and Liebermann B. Photodynamic oxygen activation by rubellin D, a phytotoxin produced by Ramularia collo-cygni (Sutton et Waller). Physiol. Mol. Plant Pathol. 62 (2003) 29-36
10. Cavalier F., Verducci J., Andrè F., Haraux F., Sigalat C., Traris M., and Vey A. Natural cyclopeptides as leads for novel pesticides tentoxin and destruxin. Pestic. Sci. 52 (1998) 81-89
11. Nozoe S., Hirai K., Tsuda K., Ishibashi K., Shirasaka M., and Grove J.F. The structure of pyrenophorin. Tetrahedron Lett. 31 (1965) 4675-4677
12. Ishibashi K. Studies on antibiotics from Helminthosporium sp. fungi. Part II. Pyrenophorin, a new antibiotic produced by Pyrenophora avenae (=Helminthosporium avenae). J. Agric. Chem. Soc. Japan 35 (1961) 257-262
13. Grove J.F. Metabolic products of Stemphylium radicinum. IV. Minor products. J. Chem. Soc. 12 (1971) 2261-2263
14. Lerario P., and Graniti A. Attivitá fitotossica della pyrenoforina e sua produzione nelle colture di Pyrenophora avenae Ito et Kurib. Phytopath. Medit. 24 (1985) 280-283
15. Colvin E.W., Purcell T.A., and Raphael R.A. Total synthesis of the macrocyclic antibiotic (+/-)-pyrenophorin. J. Chem. Soc. 16 (1976) 1718-1722
16. Bakuzis P., Bakuzis M.L.F., and Weingartner T.F. A new β-acyl vinyl anion equivalent. Synthesis of pyrenophorin. Tetrahedron Lett. 19 (1978) 2371-2374
17. Seuring B., and Seebach D. Synthese und Bestimmung der absoluten Konfiguration von Norpyrenophorin, Pyrenophorin und Vermiculin. Liebigs Ann. Chem. 12 (1978) 2044-2073
18. Dumont W., Vermeyen C., and Krief A. Novel synthetic route gamma-oxo-acrylates application to the synthesis of pyrenophorin antibiotic. Tetrahedron Lett. 25 (1984) 2883-2886
19. Ngooi T.K., Scilimati A., Guo Z.W., and Sih C.J. A chemoenzymatic route to (-)-pyrenophorin. J. Org. Chem. 54 (1989) 911
20. Machinaga N., and Kibayashi C. Preparation of macrodiolides via a common chiral building block. Total synthesis of (-)-pyrenophorin and (-)-pyrenophorol. Tetrahedron Lett. 34 (1993) 841-844
21. Baldwin J.E., Adlington R.M., and Ramcharitar S.H. A short asymmetric synthesis of (R,R)-(-)-pyrenophorin. Synlett 11 (1992) 875-877
22. Hoffman R.V., Patonay T., Nayyar N.K., and Tao J. A short, enantiospecific synthesis of a protected seco acid precursor to (R,R)-(-)-pyrenophorin. Tetrahedron Lett. 37 (1996) 2381-2384
23. Kobayashi Y., Kishihara K., and Watatani K. Two-step conversion of 2-substituted furans into γ-oxo-α,β-unsaturated carboxylic acids. Formal synthesis of (+)-patulolide A and (-)-pyrenophorin. Tetrahedron Lett. 37 (1996) 4385-4388
24. Kastanias M.A., and Chrysayi-Tokousbalides M. Bioactivity of the fungal metabolite (8R,16R)-(-)-pyrenophorin on graminaceous plants. J. Agric. Food Chem. 53 (2005) 5943-5947
25. Ishibashi K. Studies on antibiotics from Helminthosporium sp. fungi. Part VIII. Effects of ophiobolin, zizanin, pyrenophorin and siccanin on spore germination and growing mycelium of Trichophyton mentagrophytes. J. Agric. Chem. Soc. Japan 36 (1962) 645-648
26. Harding H., Williams P.H., and McNabola S.S. Chlorophyll changes, photosynthesis, and ultrastructure of chloroplasts in Albugo candida induced "green islands" on detached Brassica juncea cotyledons. Can. J. Bot. 46 (1968) 1229-1234
27. Camp R.R., and Whittingham W.F. Fine structure of chloroplasts in "green islands" and in surrounding chlorotic areas of barley leaves infected by powdery mildew. Am. J. Bot. 62 (1975) 403-409
28. Scholes J.D., and Rolfe S.A. Photosynthesis in localized regions of oat leaves infected with crown rust (Puccinia coronata): quantitative imaging of chlorophyll fluorescence. Planta 199 (1996) 573-582
29. Angra-Sharma R., and Sharma D.K. Cytokinins in pathogenesis and disease resistance of Pyrenophora teres-barley and Drechslera maydis-maize interactions during early stages of infection. Mycopathologia 148 (1999) 87-95
30. Aldesuquy H.S., Abdel-Fattah G.M., and Baka Z.A. Changes in chlorophyll, polyamines and chloroplast ultrastructure of Puccinia striiformis induced "green islands" on detached leaves of Triticum aestivum. Plant Physiol. Biochem. 38 (2000) 613-620
31. Robeson D.J., and Strobel G.A. Zinniol induces chlorophyll retention in barley leaves: the selective action of a non host-specific phytotoxin. Phytochemistry 23 (1984) 1597-1599
32. Bunkers G.J., and Strobel G.A. A proposed mode of action for green island induction by the eremophilane phytotoxins produced by Drechslera gigantea. Physiol. Mol. Plant Pathol. 38 (1991) 313-323
33. Martin C., and Thimann K.V. The role of protein synthesis in the senescence of leaves. The formation of protease. Plant Physiol. 49 (1972) 64-71
34. Sabater B., and Rodriguez M.T. Control of chlorophyll degradation in detached leaves of barley and oat through effect of kinetin on chlorophyllase levels. Physiol. Plant 43 (1978) 274-276
35. Thomas H., and Stoddart J.L. Leaf senescence. Annu. Rev. Plant Physiol. 31 (1980) 83-111
36. Holden M. Effects of EDTA and other compounds on chlorophyll breakdown in detached leaves. Phytochemistry 11 (1972) 2393-2402
37. Schistad I.J., and Nissen P. Cytokinin-induced retention of chlorophyll in senescing barley leaves: complexity of dose response. Physiol. Plant 61 (1984) 566-570
38. Mok D.W.S., and Mok M.C. Cytokinin metabolism and action. Annu. Rev. Plant Physiol. Plant Mol. Biol. 52 (2001) 89-118
39. Kotaka S., and Krueger A.P. Some observations on the bleaching effect of ethylediaminotetraacetic acid on green barley leaves. Plant Physiol. 44 (1969) 809-815
40. Cheng S.H., and Kao C.H. Localized effect of polyamines on chlorophyll loss. Plant Cell Physiol. 24 (1983) 1465-1467
41. Atkin C.L., and Neilands J.B. Leaf infections: siderochromes (natural polyhydroxamates) mimic the "green island" effect. Science 176 (1972) 300-302
42. Gönner M.V., and Schlösser E. Oxidative stress in interactions between Avena sativa L. and Drechslera spp. Physiol. Mol. Plant Pathol. 42 (1993) 221-234
43. Mandahar C.L., and Arora R.K. Infection of oat (Avena sativa L.) leaves by Helminthosporium avenae Eidam. II. Secretion of cytokinins by the pathogen in culture. Phytopath. Medit. 17 (1978) 52-54
44. Beauchamp C., and Fridovich I. Superoxide dismutase: improved assays and an assay applicable to acrylamide gels. Anal. Biochem. 44 (1971) 276-287
45. Hodges D.M., DeLong J.M., Forney C.F., and Prange R.K. Improving the thiobarbituric acid-reactive-substances assay for estimating lipid peroxidation in plant tissues containing anthocyanin and other interfering compounds. Planta 207 (1999) 604-611
46. Schoefs B., Bertrand M., and Lemoine Y. Separation of photosynthetic pigments and their precursors by reversed-phase high-performance liquid chromatography using a photodiode-array detector. J. Chromatogr. A 692 (1995) 239-245
47. Darko E., Schoefs B., and Lemoine Y. Improved liquid chromatographic method for the analysis of photosynthetic pigments of higher plants. J. Chromatogr. A 876 (2000) 111-116
48. Bradford M.M. A rapid and sensitive method for the quantitation of microgram quantities of protein utilizing the principle of protein-dye binding. Anal. Biochem. 72 (1976) 248-254
49. Peterson L.W., and Huffaker R.C. Loss of ribulose 1,5-diphosphate carboxylase and increase in proteolytic activity during senescence of detached primary barley leaves. Plant Physiol. 55 (1975) 1009-1015
50. Hiscox J.D., and Israelstam G.F. A method for the extraction of chlorophyll from leaf tissue without maceration. Can. J. Bot. 57 (1979) 1332-1334
51. Ekmekci Y., and Terzioglu S. Effects of oxidative stress induced by paraquat on wild and cultivated wheats. Pestic. Biochem. Physiol. (2005) 69-81
52. - generation during a bacterially induced hypersensitive reaction in tobacco: deterioration of membrane lipids. Physiol. Mol. Plant Pathol. 34 (1989) 13-26
53. --initiated lipid peroxidation in a bacteria-induced hypersensitive reaction in tobacco cells suspensions. Phytopathology 79 (1989) 555-562
54. May M.J., Hammond-Kosack K.E., and Jones J.D.G. Involvement of reactive oxygen species, glutathione metabolism, and lipid peroxidation in the Cf-gene-dependent defence response of tomato cotyledons induced by race-specific elicitors of Cladosporium fulvum. Plant Physiol. 110 (1996) 1367-1379
55. Rusterucci C., Stallaert V., Milat M.L., Pugin A., Ricci P., and Blein J.P. Relationship between active oxygen species, lipid peroxidation, necrosis, and phytoalexin production induced by elicitins in Nicotiana. Plant Physiol. 111 (1996) 885-891
56. Rich P.R. Quinone binding sites of membrane proteins as targets for inhibitors. Pestic. Sci. 47 (1996) 287-296
57. Feierabend J., and Winkelhusener T. Nature of photooxidative events in leaves treated with chlorosis-inducing herbicides. Plant Physiol. 70 (1982) 1277-1282
58. Naik B.I., and Srivastava S.K. Effect of polyamines on tissue permeability. Phytochemistry 17 (1978) 1885-1887
59. Popovic R.B., Kyle D.J., Cohen A.S., and Zalik S. Stabilization of thylakoid membranes by spermine during stress-induced senescence of barley leaf discs. Plant Physiol. 64 (1979) 721-726
60. Drolet G., Dumbroff E.B., Legge R.L., and Thompson J.E. Radical scavenging properties of polyamines. Phytochemistry 25 (1986) 367-371
61. Norman M.A., and Fuerst P. Interactions of cations with paraquat in leaf sections of resistant and sensitive biotypes of Conyza bonanariensis. Pest. Biochem. Physiol. 57 (1997) 181-191
62. Meller E., and Gassman M.L. The effects of levulinic acid and 4,6-dioxoheptanoic acid on the metabolism of etiolated and greening barley leaves. Plant Physiol. 67 (1981) 728-732
63. Lydon J., and Duke S.O. Porphyrin synthesis is required for photobleaching activity of the p-nitrosubstituted diphenyl ether herbicides. Pestic. Biochem. Physiol. 31 (1988) 74-83
64. Fletcher R.A., and McCullagh D. Cytokinin-induced chlorophyll formation in cucumber cotyledons. Planta 101 (1971) 88-90
65. Daub M.E. Peroxidation of tobacco membrane lipids by the photosensitizing toxin, cercosporin. Plant Physiol. 69 (1982) 1361-1364
66. Holland N., Evron Y., Jansen M.A.K., Edelman M., and Pick U. Involvement of thylakoid overenergization in tentoxin-induced chlorosis in Nicotiana spp. Plant Physiol. 114 (1997) 887-892