Bioactivity of the fungal metabolite (8R,16R)-(-)-pyrenophorin on graminaceous plants

Journal of Agricultural and Food Chemistry

Volumn 53, Issue 15, 2005, Pages 5943-5947

  Kastanias, Michael A ^a   Chrysayi Tokousbalides, Maria ^a  

^a AGRICULTURAL UNIVERSITY OF ATHENS   (Greece)

Author keywords

Avena strerilis; Graminaceous plants; Macrodiolides; Pyrenophorin; Pyrenophorol

Indexed keywords

CHLOROPHYLL; LACTONE; PYRENOPHORIN;

ARTICLE; ASCOMYCETES; BARLEY; DRUG EFFECT; GERMINATION; GROWTH, DEVELOPMENT AND AGING; METABOLISM; OAT; PLANT LEAF; PLANT ROOT; PLANT SEED; POACEAE; WHEAT;

ASCOMYCOTA; AVENA SATIVA; CHLOROPHYLL; GERMINATION; HORDEUM; LACTONES; PLANT LEAVES; PLANT ROOTS; POACEAE; SEEDS; TRITICUM;

AVENA; AVENA FATUA; AVENA SATIVA; AVENA STERILIS; CHASMANTHIUM LATIFOLIUM; DRECHSLERA AVENAE; HORDEUM VULGARE; HORDEUM VULGARE SUBSP. VULGARE; TRITICUM AESTIVUM;

EID: 23744458580     PISSN: 00218561     EISSN: None     Source Type: Journal    
DOI: 10.1021/jf050792m     Document Type: Article

References (25)

1. Lerario, P.; Graniti, A. Attivita fitotossica della pirenophorina e sua produzione nelle colture di Pyrenophora avenae Ito et. Kurib. Phytopathol. Mediterr. 1985, 24, 280-283.
2. Sugawara, F.; Strobel, G. A. (-)-Dihydropyrenophorin, a novel and selective phytotoxin produced by Drechslera avenae. Plant. Sci. 1986, 43, 1-5.
3. Sugawara, F.; Strobel, G. A. Tryptofol, a phytotoxin produced by Drechslera nodulosum. Phytochemistry 1987, 26, 1349-1351.
4. Sugawara, F.; Strobel, G.; Strange, R. N.; Siedow, J. N.; Van Duyne, G. D.; Clardy, J. Phytotoxins from the pathogenic fungi Drechslera maydis and Drechslera sorghicola. Proc. Natl. Acad. Sci., U.S.A. 1987, 84, 3081-3085.
5. Hallow, Y. F.; Clardy, J.; Kenfield, D. S.; Strobel, G. De-O-methyldiaporthin, a phytotoxin from Drechslera siccans. Phytochemistry 1988, 27, 3123-3125.
6. Sugawara, F.; Takahashi, N.; Strobel, G.; Yun, C. H.; Gray, G.; Fu, Y.; Clardy, J. Some new phytotoxic ophiobolins produced by Drechslera oryzae. J. Org. Chem. 1988, 53, 2170-2172.
7. Shulka, R. S.; Agrawal, P. K.; Thakur, R. S.; Husain, A. Drechslerol-B, a host selective phytotoxin produced by Drechslera maydis. Phytochemistry 1989, 28, 2089-2091.
8. Bunkers, G. J.; Strobel, G. A. A proposed mode of action for green island induction by the eremophilane phytotoxins produced by Drechslera gigantea. Physiol. Mol. Plant Pathol. 1991, 38, 313-323.
9. Kenfield, D.; Bunkers, G.; Strobel, G. A.; Sugawara, F. Potential new herbicides-phytotoxins from plant pathogens. Weed Technol. 1988, 2, 519-524.
10. Strobel, G. A.; Kenfield, D.; Bunkers, G.; Sugawara, F.; Clardy, J. Phytotoxins as potential herbicides. Experientia 1991, 47, 819-826.
11. Kastanias, M. A.; Chrysayi-Tokousbalides, M. Herbicidal potential of pyrenophorol isolated from a Drechslera avenae pathotype. Pest Manag. Sci. 2000, 56, 227-232.
12. Fieser, L.; Fieser, M. Reagents for organic synthesis; J. Wiley and Sons INC.: New York-London-Sydney, 1967; pp 142-143.
13. The Germination Test, Annex to Chapter 5. In Rules (International Rules for Seed Testing); Seed Science and Technology, ISTA: Zurich-Swiss, 1999; pp 155-199.
14. Hiscox, J.; Israelstam, D. A method for extraction of chlorophyll from leaf tissue without maceration. Can. J. Bot. 1979, 57, 1332-1334.
15. 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. 1961, 35, 257-262.
16. Nozoe, S.; Hirai, K.; Tsuda, K. The structure of pyrenophorin. Tetrahedron Lett. 1965, 31, 4675-4677.
17. Grove, J. F. Metabolic products of Stemphylium radicinum. Part IV. Minor products. J. Chem. Soc. 1971, 2261-2263.
18. Bacuzis, P.; Bacuzis, M. L. F.; Weingartner, T. F. A new β-acyl vinyl anion equivalent. Synthesis of pyrenophorin. Tetrahedron Lett. 1978, 19, 2371-2374.
19. Seuring, B.; Seebach, D. Synthese und bestimmung der absoluten konfiguration von norpyrenophorin, pyrenophorin und vermiculin. Liebigs Ann. Chem. 1978, 2044-2073.
20. Fujisawa, T.; Takeuchi, M.; Sato, T. A short-step synthesis of (±)-pyrenophorin utilizing 3-alkenoate as a masked synthon of 4-oxo-2-alkenoate. Chem. Lett. 1982, 11, 1795-1798.
21. Machinaga, N.; Kibayashi, C. Preparation of macrodiolides via a common chiral building block. Total synthesis of (-)-pyrenophorin and (-)-pyrenophorol. Tetrahedron Lett. 1993, 34, 1499-1502.
22. 5-reagent. Liebigs Ann. Chem. 1981, 2272-2284.
23. Nokami, J.; Takeuchi, T.; Gomyo, S.; Kakihara, T. A new approach to the synthesis of γ-hydroxy-α,β-unsaturated macrolides amd (-)-pyrenophorin by intramolecular C=C bond formation with oxidative functionalization from ω-[α-(p-chlorophenylsulfinyl)acetoxy]alkanal. Chem. Lett. 1994, 23, 1103-1106.
24. Fletcher, R. A.; McCullagh, G. Cytokinin-induced chlorophyll formation in cucumber cotyledons. Planta 1971, 101, 88-90.
25. Schistad, I. J.; Nissen, P. Cytokinin-induced retention of chlorophyll in senescing barley leaves: Complexity of dose response. Physiol. Plant. 1984, 61, 566-570.