PMID: 3760879May 1, 1986Paper

On the active principles of the Euphorbiaceae, XII. Highly unsaturated irritant diterpene esters from Euphorbia tirucalli originating from Madagascar

Journal of Natural Products
G Fürstenberger, E Hecker

Abstract

The latex of Euphorbia tirucalli originating from Madagascar contains as irritant constituents ingenane- and tigliane-type diterpene esters derived from the parent alcohols ingenol and phorbol. The main irritant constituents are isomeric 12,13-acetates, acylates of phorbol as well as 3-acylates of ingenol. As acyl groups, they carry homologous, highly unsaturated aliphatic acids of the general structure CH3-(CH2)m-(CH = CH)n-COOH (m = 2,4; n = 2,3,4,5; total number N of C-atoms = 2n + m + 2). The lack of 4-deoxyphorbol esters in this latex as compared to latex of South African origin is probably indicative of the existence of chemical races of E. tirucalli. In the acyl moiety of phorbol esters investigated in detail, an increasing number of C-atoms or an increasing number of double bonds at a fixed number of C-atoms leads to an increase of irritant activity. As compared to their saturated analogs, corresponding unsaturated phorbol esters exhibit similar irritant activities. On the other hand, by an increasing number of conjugated double bonds in the acyl moieties of phorbol esters, the promoting activity is decreased, thus indicating that irritant activity is a necessary, but insufficient, requirement for promoting activity of ...Continue Reading

Citations

Nov 8, 2006·Journal of Ethnopharmacology·Sarang BaniGhulam Nabi Qazi
Mar 24, 2016·International Journal of Molecular Sciences·Michal KorinekFang-Rong Chang
Jan 10, 2006·International Immunopharmacology·Marize C ValadaresMary L S Queiroz
Apr 21, 2016·Revista do Colégio Brasileiro de Cirurgiões·Orlando José Dos SantosIzabel Cristina Portela Bogéa Serra
Oct 12, 2013·Acta Cirúrgica Brasileira·Euler Nicolau Sauaia FilhoRennan Abud Pinheiro Santos
Aug 1, 2020·Evidence-based Complementary and Alternative Medicine : ECAM·Diego Pinha Alves da PazMaria Lucia Zaidan Dagli
Oct 18, 2019·Molecular and Clinical Oncology·Rafael Lanciani BrunettiFrancisco Javier Hernandez-Blazquez
Apr 24, 2015·Chemical Reviews·Hong-Bing WangTing-Guo Kang
May 24, 2019·Journal of Natural Products·Jiao-Jiao CuiJian-Min Yue

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