The succulent euphorbias of Nigeria. III. Structure and potency of the aromatic ester diterpenes of Euphorbia poissonii Pax.
The latex of Euphorbia poissonii was found to contain irritant aromatic diterpene esters based upon resiniferonol, 12-deoxy-16-hydroxy-phorbol and 12-deoxyphorbol. Four resiniferonol esters, 9,13,14-ortho-phenylacetyl-resiniferonol-20-0-[p-hydroxy-phenylacetate]; 9,13,14-orthophenylacetyl-resiniferonol-20-0-[m-methoxy-m'-hydroxy-phenylacetate]; 9,13,14-orthophenylacetyl-resiniferonol-20-0-acetate and resiniferonol-14-0-phenylacetate-20-0-[m-methoxy-m'-hydroxy-phenylacetate], were identified. Two further esters were identified as 12-deoxy-16-0-[2-methylbutyroyl]-phorbol-13-0-phenylacetate-20-0-acetate and 12-deoxy-16-0-[2-methylbutyroyl]-phorbol-13-0-phenylacetate. These compounds represent the first aromatic esters of this parent diterpene to be obtained from natural sources. The third group of compounds were identified as 12-deoxyphorbol-13-0-[p-hydroxy-phenylacetate]-20-0-acetate; 12-deoxyphorbol-13-0-[p-acetoxy-phenylacetate]-20-0-acetate; 12-deoxyphorbol-13-0-phenylacetate-20-0-acetate and 12-deoxyphorbol-13-0-phenylacetate. The irritant potency of the ten pure compounds was obtained using a mouse ear method for assessment of the irritant dose 50%.
D000818:Animals; D055598:Chemical Phenomena; D002621:Chemistry; D004224:Diterpenes / Q000302:isolation & purification / Q000494:pharmacology*; D004423:Ear / Q000187:drug effects; D005260:Female; D051379:Mice; D009549:Nigeria; D010031:Otitis / Q000139:chemically induced; D010703:Phorbol Esters / Q000302:isolation & purification / Q000494:pharmacology*; D010704:Phorbols / Q000494:pharmacology*; D010947:Plants, Toxic / Q000032:analysis*
D004224:Diterpenes; D010703:Phorbol Esters; D010704:Phorbols