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On the active principles of the spurge family (Euphorbiaceae)

IV. Skin irritant and tumor promoting diterpene esters from Euphorbia ingens E. Mey

  • Original Papers
  • Experimental Oncology
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Summary

The irritant and tumor-promoting principles of the latex of Euphorbia ingens E. Mey have been isolated together with several nonirritant compounds. The Euphorbia factors I1, I5, and I6 are esters of ingenane-type polyfunctional diterpene alcohols.

Euphorbia factor I1 is characterized as the 3-hexadecanoate of the polyfunctional parent alcohol ingenol and Euphorbia factor I6 as the 3-deca-2.4.6-trienoic acid ester of ingenol. Euphorbia factor I5 is the 16-angelate-3-deca-2.4.6-trienoate of 16-hydroxyingenol.

Nonirritant diterpenes of the latex are I2, the ingenol-20-hexadecanoate — an isomer of Euphorbia factor I1-and I4, the 3.7.12-triacetate-8-nicotinate of the macrocyclic lathyrane-type polyfunctional diterpene alcohol ingol.

The diterpene alcohols ingenol and 16-hydroxyingenol are inactive as irritants and tumor promoters of mouse skin. Compared to croton oil factor A1 (TPA), the Euphorbia factor I1 exhibits about 1/10 of the irritant and tumor-promoting activity in mouse skin. I1 shows no reasonable tumorigenic activity. Compared with I1, Euphorbia factors I5 and I6 are more potent irritants and less potent tumor promoters.

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Authors and Affiliations

  1. Institut für Biochemie, Deutsches Krebsforschungszentrum, Im Neuenheimer Feld 280, D-6900, Heidelberg 1, Federal Republic of Germany

    H. J. Opferkuch & E. Hecker

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  1. H. J. Opferkuch
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  2. E. Hecker
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See part III, Adolf and Hecker (1975)

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Opferkuch, H.J., Hecker, E. On the active principles of the spurge family (Euphorbiaceae). J Cancer Res Clin Oncol 103, 255–268 (1982). https://doi.org/10.1007/BF00409701

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  • DOI: https://doi.org/10.1007/BF00409701

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