Molecular modelling, synthesis and biological activity of methyl 3-Methyljasmonate and related derivatives

Tetrahedron

Volumn 53, Issue 24, 1997, Pages 8181-8194

  Ward, Jane L ^a   Gaskin, Paul ^a   Beale, Michael H ^a   Sessions, Richard ^a   Koda, Yasunori ^b   Wasternack, Claus ^c  

^a UNIVERSITY OF BRISTOL   (United Kingdom)

^b HOKKAIDO UNIVERSITY   (Japan)

^c LEIBNIZ INSTITUTE OF PLANT BIOCHEMISTRY   (Germany)

Author keywords

[No Author keywords available]

Indexed keywords

3 METHYLJASMONIC ACID METHYL ESTER; JASMONIC ACID; JASMONIC ACID DERIVATIVE; UNCLASSIFIED DRUG;

ARTICLE; BIOASSAY; DRUG SYNTHESIS; GENE EXPRESSION; IN VITRO STUDY; MASS SPECTROMETRY; MOLECULAR DYNAMICS; MOLECULAR MODEL; NUCLEAR MAGNETIC RESONANCE SPECTROSCOPY; PLANT; PLANT GROWTH; PRIORITY JOURNAL; REACTION ANALYSIS; STEREOCHEMISTRY; THERMODYNAMICS;

EID: 0030912918     PISSN: 00404020     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0040-4020(97)00485-7     Document Type: Article

References (28)

1. Sembdner G. and Parthier, B. Ann. Rev. Plant Physiol. Plant Mol. Biol. 1993, 44, 569-589.
2. Vick, B. A. and Zimmerman, D.C. Biochem. Biophys. Res. Commun., 1983, 111, 470-477.
3. Ryan, C. A. Plant Mol. Biol. 1992, 19, 123-133
4. Farmer, E. E. Plant Mol. Biol. 1994, 26, 1423-1437
5. Falkenstein, E. Groth, B. Mithofer, A. and Weiler, E. W., Planta 1991, 185, 316-322
6. Lehmann, J. Atzorn, R., Bruckner, C. Reinbothe, S., Leopold, J., Wasternack, C. and Parthier, B. Planta, 1995, 195, 156-162
7. Hause, B., Demus, U., Teichmann, C., Parthier, B. and Wasternack, C. Plant Cell Physiol. 1996, 37, 641-649.
8. Gundlach, H., Muller, M.J., Kutchan, T.M. and Zenk, M.H. Proc. Natl. Acad. Sci. U.S.A. 1992, 89, 2389-2393.
9. Mueller, M. J. and Brodschelm, W. Anal. Biochem, 1994, 218, 425-435.
10. Koda, Y., Kikuta, Y., Kitahara, T., Nishi, T and Mori, K. Phytochemistry, 1992, 31, 1111-1114.
11. Ward, J. L. and Beale, M. H. J. Chem. Soc., Perkin Trans, 1, 1993, 2379-2382.
12. Koda, Y., Ward, J. L. and Beale, M. H. Phytochemistry, 1995, 38, 821-823.
13. Taapken, T., Blechert, S., Weiler, E. W. and Zenk, M. H. J. Chem. Soc. Perkin Trans 1, 1994, 1439-1442.
14. Sakai, K., Fujimoto, T., Yamashita, M., and Kondo, K. Tet. Lett. 1985, 26, 2089-2092.
15. Iyoda, M., Kushida, T., Kitami, S. and Oda, M. J. Chem. Soc. Chem. Commun. 1987, 1607-1608.
16. Alexakis, A., Berlan, J. and Besace, Y. Tet. Lett. 1986, 27, 1047-1050.
17. Yamamoto, Y., Angew. Chem. Int Ed. 1986, 25, 947-1038.
18. Beale, M. H., Hooley, R., Lewis, M. J., Smith, S. J. and Ward, J. L. J. Chem Soc. Perkin Trans 1. 1995, 657-663.
19. Hooley, R., Smith, S.J., Beale, M.H. and Walker, R.P. Aust. J. Plant Physiol., 1993, 20. 573.
20. Okamoto, M. and Nakazawa, H. Biosci. Biotech. Biochem., 1992, 56, 1172-1173.
21. Regitz, M., Angew. Chem. Int. Ed. 1967, 6, 733-749
22. Regitz, M. and Maas, G. Diazo Compounds: Properties and Synthesis; Acad. Press, 1986; pp372-383.
23. Ikota, N., Takamura, N., Young, S.D. and Ganem, B. Tet. Lett. 1981, 22, 4163-4166
24. Blechert, S., Brodschelm, W., Holder, S., Kammerer, L., Kutchan, T. M., Meuller, M. J., Xia, Z-Q. and Zenk, M. H. Proc Natl. Acad. Sci. USA. 1995, 92, 4099-4105.
25. Wasternack, C., Atzorn, R., Blume, B., Leopold, J. and Parthier, B. Phytochemistry, 1994, 35, 49-54.
26. Wasternack, C. Trends Comparat. Biochem. Physiol. 1994, 1, 1255-1268.
27. Krumm, T., Bandemer, K. and Boland, W. FEBS Lett. 1995, 377, 523-529
28. Wasternack, C., Atzorn, R., Leopold, J., Feussner, I. Rademacher, W. and Parthier, B. Physiol. Plantarum, 1995, 94, 335-341.