Phyllostoxin and phyllostin, bioactive metabolites produced by phyllosticta cirsii, a potential mycoherbicide for cirsium arvense biocontrol

Journal of Agricultural and Food Chemistry

Volumn 56, Issue 3, 2008, Pages 884-888

  Evidente, Antonio ^a   Cimmino, Alessio ^a   Andolfi, Anna ^a   Vurro, Maurizio ^b   Zonno, Maria Chiara ^b   Motta, Andrea ^c  

^a UNIVERSITY OF NAPLES FEDERICO II   (Italy)

^b INSTITUTE OF SCIENCES OF FOOD PRODUCTION   (Italy)

^c CNR   (Italy)

Author keywords

Bicyclo octatrienyl acetic acid ester; Bioherbicides; Cirsium arvense; Hexahydrobenzodioxine carboxylic acid methyl ester; Phyllosticta cirsii; Phyllostoxin; phyllostin; Phytotoxins

Indexed keywords

BICYCLO-OCTATRIENYL ACETIC ACID ESTER; BIOHERBICIDES; CIRSIUM ARVENSE; HEXAHYDROBENZODIOXINE CARBOXYLIC ACID METHYL ESTER; PHYLLOSTICTA CIRSII; PHYLLOSTOXIN PHYLLOSTIN; PHYTOTOXINS;

ACETIC ACID; BIOASSAY; BIOCONTROL; CARBOXYLIC ACIDS; ESTERIFICATION; ESTERS; FUNCTIONAL GROUPS; METABOLISM; METABOLITES; PATHOGENS; PH;

BIOMOLECULES;

CIRSIUM; CIRSIUM ARVENSE; PHYLLOSTICTA;

EID: 80051839540     PISSN: 00218561     EISSN: 15205118     Source Type: Journal    
DOI: 10.1021/jf0731301     Document Type: Conference Paper

References (24)

1. Mitich, L. W. Thistles I: Cirsium and Carduus. Weed Technol. 1988, 2, 228-229.
2. Trumble, J. T.; Kok, L. T. Integrated pest management techniques in thistle suppression in pastures of North America. Weed Res. 1982, 22, 345-359.
3. Yuzikhin, O.; Mitina, G.; Berestetskiy, A. Herbicidal potential of stagonolide, a new phytotoxic nonenolide from Stagonospora cirsii. J. Agric. Food Chem. 2007, 55, 7707-7711. (Pubitemid 47522176)
4. Berestetskiy, A.; Gagkaeva, T. Y.; Gannibal, P. B.; Gasich, E. L.; Kungurtseva, O. V.; Mitina, G. V.; Yuzikhin, O. S.; Bilder, I. V.; Levitin, M. M. Evaluation of fungal pathogens for biocontrol of Cirsium arvense. In Proceedings of the 13th European Weed Research Society Symposium, Bari, Italy, June 19-23; Bàrberi, P., Bastiaans, L., Christensen, S. Eds.; CCBC: Bari, Italy, 2005; Abstr. 7.
5. Sakamura, S.; Niki, H.; Obata, Y.; Sakai, R.; Matsumoto, T. Isolation and structure of phytotoxic compounds produced by Phyllosticta sp. Agric. Biol. Chem. 1969, 33, 698-703.
6. Comstock, J. C.; Martinson, C. A.; Gengenbach, B. G. Host specificity of a toxin from Phyllostycta maydis for Texas cyto- plasmically male-sterile maize. Phytopathology 1973, 63, 1357-1361.
7. Entwistle, I. D.; Howard, C. C.; Johnstone, R. A. W. Isolation of brefeldin A from Phyllosticta medicaginis. Phytochemistry 1974, 13, 173-274.
8. Evidente, A. In Natural Products for Pest Management; Rimando, A. M., Duke, S. O., Eds.; ACS Symposium Series 927; American Chemical Society: Washington, DC, 2006; pp 62-75.
9. Evidente, A.; Abouzeid, M. A. In Handbook of Sustainable Weed Management; Singh, H. P., Batish, D. R., Kohli, R. K., Eds.; Haworth Press: New York, 2006; pp 507-552.
10. Evidente, A.; Cimmino, A.; Andolfi, A.; Vurro, M.; Zonno, M. C.; Motta, A. Phyllostictines A-D, Oxazatricycloalkenones Produced by Phyllosticta Cirsii, Potential Mycoherbicide of Cirsium Arvense Tetrahedron 2007, http://dx.doi.org/10.10167j.tet.2007.12.010
11. Berger, S.; Braun, S. 200 and More Basic NMR Experiments: a Practical Course, 1st ed.; Wiley-VCH: Weinheim, Germany, 2004.
12. Isogai, A.; Washizu, M.; Murakoshi, S.; Suzuki, A. A new shikimate derivative, methyl 5-lactyl shikimate lactone, from Penicillium sp. Agric. Biol. Chem. 1985, 49, 167-169.
13. Alberg, G. D.; Lauhon, C. T.; Nyfeler, R.; Fässler, A.; Bartlett, P. A. Inhibition of EPSP synthase by analogue of tetrahedral intermediate and EPSP. J. Am. Chem. Soc. 1992, 114, 335-3546.
14. Muralidharam, V. B.; Wood, H. B.; Ganem, B. Enantioselective synthesis of (-)-methyl 5-lactylshikimate lactone. Tetrahedron Lett. 1990, 31, 185-188.
15. Nakanishi, K.; Solomon, P. H. Infrared Absorption Spectroscopy, 2nd ed.; Holden Day: Oakland, CA, 1977; pp 14-53.
16. Scott, A. Interpretation of the Ultraviolet Spectra of Natural Products; Pergamon Press: Oxford, U.K., 1964; pp 45-126.
17. Pretsch, E.; Bühlmann, P.; Affolter, C. Structure Determination of Organic Compounds - Tables of Spectral Data; Springer- Verlag: Berlin, Germany, 2000; pp 161-239, 313-383.
18. Breitmaier, E.; Voelter, W. Carbon-13 NMR Spectroscopy; VCH: Weinheim, Germany, 1987; pp 183-232.
19. Porter, Q. N. Mass Spectrometry of Heterocyclic Compounds, 2nd ed.; Wiley: New York, 1985; pp 335-342.
20. Chen, C. H.; Low, B. W. Preliminary X-ray crystallographic data for methyl 3-O-(1-carboxyethyl) shikimate δ-lactone. Acta Crys- tallogr. 1966, 20, 917.
21. Sprecher, M.; Sprinson, D. B. Private communication, 1962.
22. Grieco, P. A.; Tahikawa, T.; Schillinger, W. J. Bicyclo[2.2.1]hept- anes as intermediates in the synthesis of steroids. Total synthesis of estrone. J. Org. Chem. 1980, 45, 2247-2251.
23. Kobayashi, K.; Kanno, Y.; Seko, S.; Suginome, H. Photoinduced molecular transformation. Part 135. New synthesis of taiwanin C and justicin E based on a radical cascade process involving β-scission of alkoxy radicals generated from 3- and 8-aryl-1-ehtyl- 1,2-dihydrocyclobuta[b]naphthalen-1-ols prepared by thermolysis of (Z)-tert-butyl-3-amino-3-(bicyclo[4.2.0]octa-1,3,5-trienyl)pro- penoates. J. Chem. Soc. Perkin Trans. 1 1992, 22, 3111-3117.
24. Kobayashi, K.; Kanno, Y.; Seko, S.; Suginome, H. New general synthesis of tert-butyl-3-amino-2-naphthalenecarboxylate by an electrocyclic reaction of o-quinonedimethides generated from tert- butyl (Z)-3-amino-3-(bicyclo[4.2.0] 0cta-1,3,5,trienyl-7-yl)prop-2- enoates. J. Chem. Soc. Chem. Commun. 1992, 780-781.