Identification of tenuazonic acid as a novel type of natural photosystem II inhibitor binding in QB-site of Chlamydomonas reinhardtii

Biochimica et Biophysica Acta - Bioenergetics

Volumn 1767, Issue 4, 2007, Pages 306-318

  Chen, Shiguo ^a   Xu, Xiaoming ^a   Dai, Xinbin ^a   Yang, Chunlong ^a   Qiang, Sheng ^a  

^a NANJING AGRICULTURAL UNIVERSITY   (China)

Author keywords

Binding niche; JIP test; Photosystem II inhibitor; psbA mutant; Resistance; Tenuazonic acid

Indexed keywords

3 ACYL 5 ALKYLTETRAMIC ACID; ATRAZINE; TENUAZONIC ACID; TETRAMIC ACID DERIVATIVE; UNCLASSIFIED DRUG;

ARTICLE; BINDING SITE; BIOASSAY; CHLAMYDOMONAS REINHARDTII; CHLOROPHYLL FLUORESCENCE; CONTROLLED STUDY; ELECTRON TRANSPORT; NONHUMAN; PHOTOAFFINITY LABELING; PHOTOSYNTHESIS; PHOTOSYSTEM II; PRIORITY JOURNAL; THYLAKOID;

AMINO ACID SEQUENCE; ANIMALS; ATRAZINE; BENZOQUINONES; BINDING SITES; BINDING, COMPETITIVE; CHLAMYDOMONAS REINHARDTII; ELECTRON TRANSPORT; MOLECULAR SEQUENCE DATA; MUTATION; OXYGEN; PHOTOSYSTEM II PROTEIN COMPLEX; PROTEIN CONFORMATION; PYRROLIDINONES; TENUAZONIC ACID; THYLAKOIDS;

AGERATINA ADENOPHORA; ALTERNARIA ALTERNATA; CHLAMYDOMONAS REINHARDTII;

EID: 34047243815     PISSN: 00052728     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.bbabio.2007.02.007     Document Type: Article

References (68)

1. Chelkowski J., and Visconti A. Alternaria Biology, Plant Diseases and Metabolites (1992), Elsevier, Amsterdam 449-541
2. Motta S.D., and Soares L.M.V. Simultaneous determination of tenuazonic and cyclopiazonic acids in tomato products. Food Chem. 71 (2000) 111-116
3. Enans N., Mcroberts N., Hill R.A., and Marshall G.M. Phytotoxin production by Alternaria linicola and phytoalexin production by the linseed host. Ann. Appl. Biol. 129 (1996) 415-431
4. Davies N.D., Diner U.L., and Morgan-Jones G. Tenuazonic acid production by Alternaria alternata and Alternaria tenuissima isolated from cotton. Appl. Environ. Microbiol. 34 (1977) 155-157
5. Yuki H., Kariya K., and Hashimoto Y. Synthesis and anti-tumor activity of tenuazonic acid analogues. Chem. Pharm. Bull (Tokyo) 15 (1967) 727-729
6. Dacero A.M., Combina M., and Etcheverry M. Evaluation of Alternaria and its phytotoxins during ensiling of sunflower seeds. Nat. Toxins 5 (1997) 20-23
7. Tylkowska K., Grabarkiewicz-Szczesna J., and Iwanowska H. Production of toxins by Alternaria alternata and A. radicina and their effects on germination of carrot seeds. Seed Sci. Technol. 31 (2003) 309-316
8. Conno Z.M., and Vurro M. Effect of fungal toxins on germination of Striga hermonthica seeds. Weed Res. 39 (1999) 15-20
9. Janardhanan K.K., and Husain A. Studies on isolation, purification and identification of tenuazonic acid, a phytotoxin produced by Alternaria alternata (Fr.) Keissler causing leaf blight of Datura innoxia Mill. Mycopathologia 83 (1983) 135-140
10. Qiang S., Wan Z.X., Dong Y.F., and Li Y.H. Phytotoxicity of rude metabolites produced by Alternaria alternata to Croften weed. The Sustainable Management of Weeds Meeting the 21st Century in China (1999), Guangxi Nationality Press, Nanning 158-165
11. Wan Z.X., Qiang S., Xu S.C., Shen Z.G., and Dong Y.F. Culture conditions for production of phytotoxin by Alternaria alternata and plant range of toxicity. Chin. J. Biol. Control 17 (2001) 10-15
12. Wan Z.X., Zhu J.J., and Qiang S. The pathogenic mechanism of toxin of Alternaria alternata (Fr.) Keissler to Eupatorium adenophorum. J. Plant Resour. Environ. 10 (2001) 47-50
13. C.F. An, Thesis for Master degree: On potential of metabolite of Alternaria alternata as bio-source herbicide, Nanjing Agricultural University (2003).
14. S. Qiang, Y.F. Dong, C.F. An, B. Zhou, Y.Z. Zhu, S.G. Chen, X.B. Dai, B.J. Dai, J.G. Cai, Biological control of weeds using the metabolites of Alternaria alternata (Fr.) Keissler, (2005) Appl. No (China patent): 200510038263.2, CN1644046, PCT/CN2005/002367.
15. Friedman M.A., Aggarwal V., and Lester G.E. Inhibition of epidermal DNA synthesis by cycloheximide and other inhibitors of protein synthesis. Res. Commun. Chem. Pathol. Pharmacol. 11 (1975) 311-318
16. Meazza G., Scheffler B.E., Tellez M.R., Rimando A.M., Romagni J.G., Duke S.O., Nanayakkara D., Khan I.A., Abourashed E.A., and Dayan F.E. The inhibitory activity of natural products on plant p-hydroxyphenylpyruvate dioxygenase. Phytochemistry 59 (2002) 281-288
17. Marfori E.C., Kajiyama S.I., Fukusaki E.I., and Kobayashi A. Phytotoxicity of the tetramic acid metabolite trichosetin. Photochemistry 62 (2003) 715-721
18. Dai X.B., Chen S.G., Qiang S., An Q.F., and Zhang R.X. Effect of Toxin from Alternaria alternata (Fr.) Keissler on leaf photosynthesis of Eupatorium adenophorum Spreng. Acta Phytopathol. Sin. 34 (2004) 55-60
19. Chen S.G., Dai X.B., Qiang S., and Tang Y.L. Effect of a nonhost-selective toxin from Alternaria alternate on chloroplast-electron transfer activity in Eupatorium adenophorum. Plant Pathol. 54 (2005) 671-677
20. Kern J., Loll B., Lüneberg C., DiFiore D., Biesiadka J., Irrgang K.D., and Zouni A. Purification, characterisation and crystallisation of photosystem II from Thermosynechococcus elongatus cultivated in a new type of photobioreactor. Biochim. Biophys. Acta 1706 (2005) 147-157
21. Kless H., and Vermaas W. Tandem sequence duplications functionally complement deletions in the D1 protein of photosystem II. J. Biol. Chem. 270 (1995) 16536-16541
22. Takahashi Y., Utsumi K., Yamamoto Y., Hatano A., and Satoh K. Genetic engineering of the processing site of D1 precursor protein of photosystem II reaction center in Chlamydomonas reinhardtii. Plant Cell Physiol. 37 (1996) 161-168
23. Xiong J., Subramaniam S., and Govindjee. Modeling of the D1/D2 proteins and cofactors of the photosystem II reaction center: implications for herbicide and bicarbonate binding. Protein Sci. 5 (1996) 2054-2073
24. Przibilla E., Heiss S., Johanningmeier U., and Trebst A. Site-specific mutagenesis of the D1 subunit of photosystem II in wild-type Chlamydomonas. Plant Cell 3 (1991) 169-174
25. Trebst A. The three-dimensional structure of the herbicide binding niche on the reaction center polypeptides of photosystem II. Z. Naturforsch. 42C (1987) 742-750
26. Oettmeier W., Masson K., and Johanningmeier U. Evidence for two different herbicide-binding proteins at the reducing side of photosystem II. Biochim. Biophys. Acta 679 (1982) 376-383
27. Oettmeier W., Masson K., and Hecht H.J. Heterocyclic ortho-quinones, a novel type of photosystem II inhibitors. Biochim. Biophys. Acta 1504 (2001) 346-351
28. Mackay S.P., and O'Malley P.J. Molecular modeling of the interactions between optically active triazine herbicides and photosystem II. Z. Naturforsch. 48c (1993) 474-481
29. Oetteier W. Herbicide resistance and supersensitivity in photosystem II, CMLS. Cell. Mol. Life Sci. 55 (1999) 1255-1277
30. Ohad N., and Hirschberg J. Mutations in the D1 subunit of photosystem II distinguish between quinine and herbicide binding sites. Plant Cell 4 (1992) 273-282
31. Qiang S., Chang Y., Wan Z.X., and Li Y.H. Comparison on pathogenicity and other characteristics of five isolates of Alternaria alternata from Eupatorium adenophorum. J. Nanjing Agric. Univ. 25 (2002) 23-27
32. Porra R.J., Thompson W.A., and Kriedemann P.E. Determination of accurate extinction coefficients and simultaneous equations for assaying chlorophylls a and b extracted with four different solvents: verification of the concentration of chlorophyll standards by atomic absorption spectroscopy. Biochim. Biophys. Acta 975 (1989) 384-394
33. Xiong J., Hutchison R.S., Sayre R.T., and Govindjee. Modification of photosystem II acceptor side function in a D1 mutant (arginine-269-glycine) of Chlamydomonas reinhardtii. Biochim. Biophys. Acta 1322 (1997) 60-76
34. Coombs J., Hall D.O., Long S.P., and Scurlock J.M.O. Techniques in Bioproductivity and Photosynthesis (1986), Science Press, Beijing 142-144
35. Strasser R.J., Tsimilli-Michael M., and Srivastava A. Analysis of the chlorophyll a fluorescence transient. Chlorophyll Fluorescence: A Signature of Photosynthesis (2004), Kluwer Academic Publishers Press, Netherlands 1-45 Chap. 12
36. Srivastava A., Jüttner F., and Strasser R.J. Action of the allelochemical, fischerellin A, on photosystem II. Biochim. Biophys. Acta 1364 (1998) 326-336
37. Tsimilli-Michael M., Eggenberg P., Biro B., Köves-Pechy K., Vörös I., and Strasser R.J. Synergistic and antagonistic effects of arbuscular mycorrhizal fungi and Azospirillum and Rhizobium nitrogen-fixers on the photosynthetic activity of alfalfa, probed by the polyphasic chlorophyll a fluorescence transient O-J-I-P. Appl. Soil. Ecol. 15 (2000) 169-182
38. Jursinic P.A., McCarthy S.A., Bricher T.M., and Stemler A. Characteristics of two atrazine-binding sites that specifically inhibit photosystem II function. Biochim. Biophys. Acta 1059 (1991) 312-322
39. Schreiber U., Schliwa U., and Bilger W. Continuous recording of photochemical and non-photochemical chlorophyll fluorescence quenching with a new type of modulation fluorometer. Photosynth. Res. 10 (1986) 51-62
40. Philip H., and John B. Changes in chlorophyll fluorescence during exposure of Dunaliella tertiolecta to UV radiation indicate a dynamic interaction between damage and repair processes. Photosynth. Res. 63 (2000) 123-134
41. Zhu X.G., Govindjee, and Baker N.R. Chlorophyll a fluorescence induction kinetics in leaves predicted from a model describing each discrete step of excitation energy and electron transfer associated with photosystem II. Planta 223 (2005) 114-133
42. Strasser R.J., Srivastava A., and Govindjee. Polyphasic chlorophyll a fluorescence transient in plants and cyanobacteria. Photochem. Photobiol. 61 (1995) 32-42
43. Pfister K., Radosevich S.R., and Arntzen C. Modification of herbicide binding to photosystem II in two biotype of Senecio vulgaris L. Plant Physiol. 64 (1979) 995-999
44. Tellenbach M., Gerber A., and Boschetti A. Herbicide-binding to thylakoid membranes of a DCMU-resistant mutant of Chlamydomonas reinhardtii. FEBS Lett. 158 (1983) 147-150
45. Astier C., Boussac A., and Etienne A.L. Evidence for different binding sites on the 33-kDa protein for DCMU, atrazine and QB. FEBS Lett. 167 (1984) 321-326
46. Metz J.G., Pakrasi H.B., Seibert M., and Arntzen C.J. Evidence for a dual function of the herbicide-binding D1 protein in photosystem II. FEBS Lett. 205 (1986) 269-274
47. Kamiya N., and Shen J.R. Crystal structure of oxygen-evolving photosystem II from Thermosynechococcus vulcanus at 3.7-Å resolution. Proc. Natl. Acad. Sci. U. S. A. 100 (2003) 98-103
48. Sinning I. Herbicide binding in the bacterial photosynthetic reaction center. Trends Biochem. Sci. 17 (1992) 150-154
49. B. Structure 5 (1997) 1339-1359
50. Lancaster C.R.D., and Michel H. Refined Crystal Structures of Reaction Centres from Rhodopseudomonas viridis in complexes with the herbicide atrazine and two chiral atrazine derivatives also lead to a new model of the bound carotenoid. J. Mol. Biol. 286 (1999) 883-898
51. Lancaster C.R.D., Bibikovai M.V., Sabatino P., Oesterhelt D., and Michel H. Structural basis of the drastically increased initial electron transfer rate in the reaction renter from a Rhodopseudomonas viridis mutant described at 2.00-Å resolution. J. Biol. Chem. 275 (2000) 39364-39368
52. Trebst A. The topology of the plastoquinone and herbicide binding peptides of photosystem II in the thylakoid membrane. Z. Naturforsch. 41C (1986) 240-245
53. Strasser R.J., and Govindjee. In: Argyroudi-Akoyunoglou J.H. (Ed). Regulation of Chloroplast Biogenesis, The Fo and the O-J-I-P Fluorescence Rise in Higher Plants and Algae (1992), Plenum Press, New York 423-426
54. Strauss A.J., Krüger G.H.J., Strasser R.J., and Van Heerden P.D.R. Ranking of dark chilling tolerance in soybean genotypes probed by the chlorophyll a fluorescence transient O-J-I-P. Environ. Exp. Bot. 56 (2006) 147-157
55. Oettmeier W., Masson K., and Donner A. Anthraquinone inhibitors of photosystem II electron transport. FEBS Lett. 231 (1988) 259-262
56. Bacon K. Photosynthesis-Photobiochemistry and Photobiophysics (2001), Kluwer Academic Publishers, Dordrecht 301-303
57. Funk C., Wiklund R., Schrder W.P., and Jansson C. D1' centers are less efficient than normal photosystem II centers. FEBS Lett. 505 (2001) 113-117
58. Mackay S.P., and O'Malley P.J. Molecular modeling of the interaction between DCMU and the QB-binding site of photosystem II. Z. Naturforsch. 48c (1993) 191-198
59. Mackay S.P., and O'Malley P.J. Molecular modelling of the interaction of Cyanoacrylate inhibitors with photosystem II, Part 2. the effect of stereochemistry of inhibitor binding. Z. Naturforsch. 48c (1993) 782-787
60. Xiong J., Subramaniam S., and Govindjee. A knowledge-based three dimensional model of the photosystem II reaction center of Chlamydomonas reinhardtii. Photosynth. Res. 56 (1998) 229-254
61. Camara-Artigas A., and Allen1 J.P. Comparative analyses of three-dimensional models of bacterial reaction centers. Photosynth. Res. 81 (2004) 227-237
62. B) binding site of the D-1 reaction center polypeptide of photosystem II. FEBS Lett. 239 (1988) 207-210
63. Föster B., Heifetz P.B., Lardans A., Boynton J., and Gillham N.W. Herbicide resistance and growth of D1 Ala251 mutant in Chlamydomonas. Z. Naturforsch. 52c (1997) 654-664
64. Spyridaki A., Fritzsch G., Kouimtzoglou E., Baciou L., and Ghanotakis D. The natural product capsaicin inhibits photosynthetic electron transport at the reducing side of photosystem II and purple bacterial reaction center: structural details of capsaicin binding. Biochim. Biophys. Acta 1459 (2000) 69-76
65. Ouchane S., Picaud M., and Astier C. A new mutation in the pufL gene responsible for the terbutryn resistance phenotype in Rubrivivax gelatinosus. FEBS Lett. 374 (1995) 130-134
66. Sopp G., Rutherford W.A., and Oettmeier W. A single mutation in the M-subunit of Rhodospirillum rubrum confers herbicide resistance. FEBS Lett. 409 (1997) 343-346
67. Govindjee, Eggenberg P., Pfister K., and Strasser R.J. Chlorophyll a fluorescence decay in herbicide-resistant D1 mutants of Chlamydomonas reinhardtii and the formate effect. Biochim. Biophys. Acta 1101 (1992) 353-358
68. Liu H.Y., Lou R.J., and Yang H.Z. Research progress on structure-activity relationship of photosystem II inhibitor. World Pestic. 19 (1997) 20-24