Planta Med 2001; 67(5): 475-477
DOI: 10.1055/s-2001-15814
Letter

© Georg Thieme Verlag Stuttgart · New York

Synthesis and Biosynthesis of Isocordoin

Alberto Vitali1 , Franco Ferrari1 , Giuliano Delle Monache1,*, Ezio Bombardelli2 , Bruno Botta3,*
  • 1 Centro Chimica dei Recettori del C.N.R., Università Cattolica, Roma, Italy
  • 2 Indena S.p.A., Milano, Italy
  • 3 Dipartimento di Chimica e Tecnologia delle Sostanze Biologicamente Attive, Università La Sapienza, Roma, Italy
Weitere Informationen

Publikationsverlauf

July 25, 2000

November 5, 2000

Publikationsdatum:
31. Dezember 2001 (online)

Abstract

In the search of a convenient synthesis for isocordoin (1), a potential anticancer natural product, 2′,4′-dihydroxychalcone was inoculated in cell suspension cultures of Morus nigra, which were expected to contain an active prenyltransferase. After 24 hours the target compound was easily isolated from the metabolite extract. Optimization of the biotransformation resulted in a 85 % yield of the prenyl derivative.

References

  • 1 Gonçalves de Lima O, Marini Bettolo G B, De Mello J F, Delle Monache F, De Barros Coelho J S, de Andrade Lyra F D, Machado F et al. C- and O-prenylated chalcones from Cordoa piaca .  Gazzetta Chimica Italiana. 1973;  103 771-7
  • 2 do Nascimento M C, Mors W. Chalcones of the root bark of Derris sericea .  Phytochemistry. 1972;  11 3023-8
  • 3 Jain A C, Lal P, Seshadri T. A study of nuclear prenylation of β-resacetophenone II. Synthesis of bavachalcone, 4′-O-methylbavachalcone and bavachin.  Tetrahedron. 1970;  26 263-5
  • 4 Khanna R N, Khanna P L, Manchanda V P, Seshadri T R. Synthesis of derricin, derricidin and related compounds.  Indian Journal of Chemistry. 1973;  11 1225-7
  • 5 Lupi A, Delle Monache F, Marini Bettolo G B, Goncalves de Lima O, De Mello J F. Synthesis of the prenylated chalcones from Cordoa piaca .  Il Farmaco - Ed. Sc.. 1975;  30 449-55
  • 6 De Vincenzo R, Scambia G, Benedetti Panici P, Ranelletti F O, Bonanno G, Ercoli A et al. Effect of synthetic and naturally occurring chalcones on ovarian cancer cell growth: structure-activity relationship.  Anti-Cancer Drug Design. 1995;  10 481-90
  • 7 Bohlman F, Kleine K M. Über ein neues Chinon aus höheren Pflanzen.  Chemische Berichte. 1966;  99 885-8
  • 8 Laflamme P, Khouri H, Gulick P, Ragai I. Enzymic prenylation of isoflavones in white lupin.  Phytochemistry. 1993;  34 147-51 and references cited therein
  • 9 Ferrari F, Monacelli B, Messana I. Comparison between in Vitro and in Vitro metabolite production of Morus nigra .  Planta Medica. 1999;  65 85-7
  • 10 Y. Hano Y, Nomura T, Ueda S. Biosynthesis of optically active Diels-Alder type adducts revealed by an aberrant metabolism of O-methylated precursors in Morus alba cell cultures.  Journal of Chemical Society, Chemical Communication. 1990;  8 610-3
  • 11 Murashige T, Skoog F. Revised medium for rapid growth and bioassays with tobacco tissue culture.  Plant Physiology. 1962;  473-9

Dr. G. Delle Monache

Centro Chimica Recettori, C.N.R.

UniversitÈ Cattolica S. Cuore

Largo F. Vito, 1

00168 Roma

Italy

eMail: g.dellemonache@uniserv.ccr.rm.cnr.it

Fax: +39 06 3053598

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