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(E)-Cinnamic Acid Analogues as Inhibitors of Phenylalanine Ammonia-Lyase and of Anthocyanin Biosynthesis

Autorzy
Identyfikatory
Warianty tytułu
Języki publikacji
EN
Abstrakty
EN
Several carboxylic, phosphonic, phosphinic, boronic and nitro analogues of (E)-cinnamic acid were synthesized. These and other compounds related to (E)-cinnamic acid were evaluated as potential inhibitors of both phenylalanine ammonia-lyase and of anthocyanin biosynthesis in buckwheat. The most potent inhibition was found for 3-phenylprop-2-ynoic acid (21), however its Ki is comparable to KM. The molecular modelling of the interaction of (E)-cinnamic acid (1) and 21 with PAL model suggests some similarities in the binding mode of both compounds.
Rocznik
Strony
583--592
Opis fizyczny
Bibliogr. poz. 42, rys.
Twórcy
autor
  • Faculty of Chemistry, Wrocław University, F. Joliot-Curie 14, 50-383 Wrocław, Poland
Bibliografia
  • 1.Croteau R., Kutchan T.M. and Lewis N.G., in Biochemistry &. Molecular Biology of Plants, ed. B.B. Buchanan, W. Gruissem and R.L. Jones, American Society of Plant Physiologists, Rockville, MD, 2000, pp. 1250-1318.
  • 2.La Camera S., Gouzerth G., Dhondt S., Hoffman L., Fritig B., Legrand M. and HeitzT., Immunological Rev., 198, 267 (2004).
  • 3.Dixon R. A., Achnin L., Kota P., Liu C. –J., Reddy M. S. and Wang L., Molecular Plant Pathology 3, 371 (2002).
  • 4.Quidcau S., Jurpes M., Saucier C., Glories Y., Pardon P. and Baudry C., Angew. Chem. Int. Ed. 42, 6012 (2003)
  • 5.Dixon R.A. and Ferreira D., Phytochemistry, 60, 205 (2002).
  • 6.Miyazawa M., Ando H., Okuno Y. and Araki H.,.J Mol. Catalysis B Enzymatic, 27, 91 (2004).
  • 7.Du Y., Wei G. and Linhardt R.J.,.J. Org. Chen'.., 69, 2206 (2004).
  • 8.Poppe L. and Retey J., Curr. Org. Chem., 7, 1297 (2003).
  • 9.Röther D., Poppe L., Morlock G., Viergutz. S. and Retey J., Eur. J. Biochem., 269, 3065 (2002).
  • 10.Zoń J., Szefczyk M., Sawka-Dobrowolska W., Gancarz R., Kucharska-Zoń M., Latajka R., Amrhein N., Miziak P. and Szczepanik W., New J. Chem., 28, 1048 (2004).
  • 11.Meyer Li.A., Castellano R.K. and Dicdcrich I, Angew. Chem. Int. Ed., 42, 1210 (2003).
  • 12.Jez. J.M., Bowman M.K. and Noel J.P., Proc. Natl. Acad. Sei. USA, 99, 5319 (2002).
  • 13.Ferrer J.L., Jez. J.M., Bowman M.L., Dixon R.A. and Noel J.P., Nature Struct Biol., 6, 775 (1999).
  • 14.Zubieta C, Kota P., Ferrer J.L., Dixon R.A. and Noel J.P., Plant Cell. 14, 1265 (2002).
  • 15.Jorrin J., López-Valbuena R. and Tena M., Biochim. Biophys. Acta, 964, 73 (1988).
  • 16.Sato T., Kiuchi F. and Sankawa U., Phytochemistry, 21, 845 (1982).
  • 17.Hodgins D., J. Biol. Chem., 246, 2977 (1971).
  • 18.Minamikawa T. and Uritani I.,.J. Biochem. (Tokyo), 58, 53 (1965).
  • 19.Glogc A., Zoń J., Kövari A., Poppe L. and Retey J., Chem. Eur..J., 6, 3386 (2000).
  • 20.Appert C., Zoń J. and Amrhein N., Phytochemistry, 62, 4 15 (2003).
  • 21.Zoń J. and Amrhein N., Liebigs Ann. Chem., 625 (1992).
  • 22.Zoń J., Amrhcin N. and Gancarz R., Phytochemistry, 59, 9 (2002).
  • 23.Laber B., Kiltz H.H. and Amrhein N., Z Naturforsch., 41c, 49 (1986).
  • 24.Janas K.M., Filipiak A., Kowalik J., Mastalcrz.P. and Knypl J.S., Acta Biochim. Pol., 32,131 (1985).
  • 25.Amrhein N. and Gödeke K.H., Plant Sei. Lett., 8, 313 (1977).
  • 26. Coley J.R. and Kamarewsky V.I.,.J. Am. Chem. Sac., 74, 4448 (1952).
  • 27.Zoń J. and I.aber B., Phytochemistry, 27, 711 (1988).
  • 28.Hülskämper L. and Weyerstahl P., Chem. Ber., 114, 746 (1981).
  • 29.Herbst R.M. and Shemin I)., Organic Synthesis coll. vol. II, 1 (1943).
  • 30.Bergman F. and Bondi A., Chem. Ber., 66, 278 (1933).
  • 31.Fedorova G.K., Ruban P.N. and Kirsanov A.V., Zh. Obshch. Khim., 39, 1471 (1969).
  • 32.Hormi O.F.O., Pąjunen H.O., Avail A.K.C., Pennanen P., Näsman J.H. and Sundell M., Synthetic Commun , 20. 1865 (1990).
  • 33.Chatta M.S. and Aguiar A.M.,.J. Org. Chem., 36, 2719 (1971).
  • 34.Fridland S.W. and Ffrcmow A.I., Zh. Obshch. Chem., 48, 319 (1978).
  • 35.Brown, H.C. and Gupta, S.K.,.J. Am. Chem. Soc.. 97, 5249 (1975).
  • 36.Gairaud C.B. and Lappin G.R.,.J. Org. Chem., 18, I (1953).
  • 37.Bhattacharjya A., Mukhopadhyay R. and Pakrashi S.C., Synthesis, 886 (1985).
  • 38.Gaussian 03, Revision B.05, Frisch M.J., Trucks G.W., Schlegel H.B., Scuseria G.E., Robb M.A., Cheeseman J.R., Montgomery J.A. Jr., Vreven T., Kudin K.N., Burant J.C., Millam J.M., Iyengar S.S., Tomasi J., Barone V., Mennucci B., Cossi M., Scalmani G., Rega N., Petersson G.A., Nakatsuji H., Hada M., Fhara M., Toyota K., Fukuda R., I lasegawa J., Ishida M., Nakajima F., Honda Y., Kitao O., Nakai 11., Kiene M., I.i X., Knox J.F... Hratchian I I.P., Cross J.B., Adamo C., Jaramillo J., Gomperts R., Stratmann R.E., Yazyev O., Austin A.J., Cammi R., Pomelli C., Ochterski J.W.. Ayala P.Y., Morokuma K.. Voth G.A., Salvador P., Dannenberg J.J., Zakrzewski V.G., Dapprich S., Daniels A.D., Strain M.C., Farkas O., Malick D.K., Rabuck A.D., Raghavachari K., Foresman J.B., Ortiz.I.V., Cui Q„ Baboul A.G., Clifford S., Cioslowski J., Stelanov B.B., Liu G., Liashenko A., Piskorz P., Komaromi I., Martin R.L., Fox D..I., Keith T., Al-Laham M.A., Peng C.Y., Nanayakkara A., Challacombc M., Gill P.M.W., Johnson B., Chen W., Wong M.W., Gonzalez. C. and Pople J.A., Gaussian, Inc., Pittsburgh PA, 2003.
  • 39.Morris G.M., Goodsell D.S., Halliday R.S., Huey R., Hart W.H., Belew R.K. and Olson A.J., J. Comp. Chem., 19, 1639(1998).
  • 41.Richtarski G., Soroka M., Mastalerz P. and Starzemska H., Rocz. Chem., 49, 2001 (1975).
  • 42.Hamberger B. and Hahlbrock K„ Proc. Natl. Acad. Sei. USA. 101, 2209 (2004).
Typ dokumentu
Bibliografia
Identyfikator YADDA
bwmeta1.element.baztech-article-BUJ3-0002-0067
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