Irritant contact dermatitis in humans from phorbol and related esters

Three new ingenane derivatives from the latex of Euphorbia canariensis L

“…We and other groups have experienced difficulties in the isolation of naturally occurring esters of ingenol from Euphorbia species, since these compounds tend to occur in complex mixtures that are difficult to separate and may be unstable to conventional phytochemical techniques of fractionation (Adolf and Hecker, 1975; Upadhyay and Hecker, 1975; Hickey et al, 1981;Abo and Evans, 1982). Droplet countercurrent chromatography has been applied in our laboratory earlier for the separation of the tigliane derivatives phorbol and 4a-phorbol from croton oil (Marshall and Kinghorn, 1981), and the modified system described in this paper presents a substantial improvement over existing methods for the rapid isolation, without apparent decomposition leading to artifact formation, of biologically active ingenane derivatives.…”

“…In view of the potent activity displayed by ingenol-3.5.20-triacetate (7) (Hickey et al, 1981), the presence of the skin-irritant compounds 1-3 in E. canariensis latex in a combined yield of about 0.15% w/w would be expected to cause severe and prolonged inflammation if contacted with human skin. In addition, it may be pointed out that 1-3 were obtained from the same E. canariensis specimen as was the latex found by Roe and Peirce (1961) to exhibit tumor-promoting activity on mouse skin (Keesing, 1982).…”

Plants and Plant Products

“…in a gardener [237], an irritant patch test reaction to the petty spurge (Euphorbia peplus L.), a garden weed presented by the patient as a house plant [238], perioral dermatitis from a pencil tree (Euphorbia tirucalli L.) [239]. Several authors described the irritant properties of the friendship cactus (Euphorbia hermentiana Lemaire) following the use of this plant by a bank as an inducement to open a savings account [240], examined the irritant properties of a number of tigliane, ingenane and daphnane polyol esters in humans [241], or described a case of an 8-year-old girl who developed irritation and swelling of the face and eyelids as a result of a fight in which a boy beat her with snow-on-the-mountain (Euphorbia marginata Pursh) [242]. We have observed irritant dermatitis in a botanist who had botanized and made contact with euphorbia (Fig.…”

Euphorbiaceae Juss.

“…These esters can be grouped into three categories: the tiglianes (phorbols), ingenanes (ingenols), and daphnanes (huratoxins) (Evans and Soper 1978;Spoerke and Smolinske 1990). All produce similar effects, but their irritant potency may vary considerably; the effects of some on the skin may persist for several days or more (Hickey et al 1981). These species are of considerable importance as skin irritants in humans, and there is interest in evaluating their potency.…”