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Planta Med 1984; 50(1): 65-69
DOI: 10.1055/s-2007-969623
Research Articles

© Georg Thieme Verlag Stuttgart · New York

Structure Activity Relations of Polyfunctional Diterpenes of the Tigliane Type, VI1

Irritant and tumor promoting activities of semisynthetic mono and diesters of 12-deoxyphorbolS. Zayed2 , 3 , B. Sorg3 , E. Hecker3
  • 2National Research Centre, Dokki, Kairo, Egypt
  • 3Institut für Biochemie, Deutsches Krebsforschungszentrum, D-6900 Heidelberg 1, Im Neuenheimer Feld 280
1 Vth communication: Marston, A., Hecker, E. (1983) Z. Naturforsch. 38b, 1015
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Publication Date:
26 February 2007 (online)

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Abstract

A method for the isolation and preparation of 12-deoxyphorbol (1) from Euphorbium resin (Euphorbia resinifera Berg) was established to provide substantial amounts of 1-esters for bioassays. Acylation of 1 yielded 12-deoxyphorbol-13,20-diesters (2, esters with acids CH3(CH2)nCOOH, n = 0, 4, 8, 12, 16, 20; and with benzoic, oleic, elaidic and linoleic acid). Upon mild transesterification the 13,20-diesters 2 yielded the 13-monoesters 3. Both ester types were tested for their irritant activities, the 13-monoesters were also assayed for their tumor-promoting activity. A dependance of both of these activities on the chain length of the acyl residues is noticeable. For both probably a broad maximum exists around the tetradecanoate.