On the active principles of the spurge family. III. Skin irritant and cocarcinogenic factors from the caper spurge. 1975

W Adolf, and E Hecker

The toxic and irritant principles of the seed oil and of the latex of the caper spurge (Euphorbia lathyris L.) were isolated together with several non irritants of similar chemical structure. From the seed oil two irritant Euphorbia factors L5 and L6 and from the latex a mixture of irritant Euphorbia factors were obtained. Euphorbia factor L5 was identified as 3-hexadecanoate of the new tetracyclic, poly-functional diterpene parent alcohol ingenol. Euphorbia factor L6 most probably is the 3-tetradeca-2,4,6,8,10-penta-enoic acid ester of ingenol. The mixture of Euphorbia factors was shown to contain esters of ingenol and of 16-hydroxy-ingenol, respectively, each containing a long chain unsaturated fatty acid, most probably in 3-position. The non irritants from the seed oil comprise ingenol-20-hexadecanoate (compound L4) and several esters of macrocyclic diterpenes of the new lathyrol type (compounds L1-L3, L8, and possibly L7). Compound L4 is a positional isomer of Euphorbia factor L5 and most probably an artefact formed during the isolation procedure. The macrocyclic diterpenes are of interest as possible intermediates in the biogenesis of tetracyclic diterpene parents of cocarcinogenic esters. The parent alcohols ingenol and 16-hydroxy-ingenol are inactive irritants. As compared to croton oil factor A1 (TPA), Euphorbia factor L5 exhibits about 1/10 of its irritant activity on the ear and about 1/10 of its cocarcinogenic activity on the back skin of mice. As an irritant Euphorbia factor L6 shows about 1/5 of the activity of A1. Structure/activity relationships of ingenol and phorbol esters and the possible role of cocarcinogens of plant origin as second order carcinogenic risk factors are discussed.

UI MeSH Term Description Entries
D007509 Irritants Drugs that act locally on cutaneous or mucosal surfaces to produce inflammation; those that cause redness due to hyperemia are rubefacients; those that raise blisters are vesicants and those that penetrate sebaceous glands and cause abscesses are pustulants; tear gases and mustard gases are also irritants. Counterirritant,Counterirritants,Irritant,Pustulant,Pustulants,Rubefacient,Rubefacients,Vesicant,Vesicants
D008297 Male Males
D009821 Oils Unctuous combustible substances that are liquid or easily liquefiable on warming, and are soluble in ether but insoluble in water. Such substances, depending on their origin, are classified as animal, mineral, or vegetable oils. Depending on their behavior on heating, they are volatile or fixed. (Dorland, 28th ed)
D010947 Plants, Toxic Plants or plant parts which are harmful to man or other animals. Plants, Poisonous,Plant, Poisonous,Plant, Toxic,Poisonous Plant,Poisonous Plants,Toxic Plant,Toxic Plants
D002273 Carcinogens Substances that increase the risk of NEOPLASMS in humans or animals. Both genotoxic chemicals, which affect DNA directly, and nongenotoxic chemicals, which induce neoplasms by other mechanism, are included. Carcinogen,Oncogen,Oncogens,Tumor Initiator,Tumor Initiators,Tumor Promoter,Tumor Promoters,Initiator, Tumor,Initiators, Tumor,Promoter, Tumor,Promoters, Tumor
D002280 Carcinoma, Basal Cell A malignant skin neoplasm that seldom metastasizes but has potentialities for local invasion and destruction. Clinically it is divided into types: nodular, cicatricial, morphaic, and erythematoid (pagetoid). They develop on hair-bearing skin, most commonly on sun-exposed areas. Approximately 85% are found on the head and neck area and the remaining 15% on the trunk and limbs. (From DeVita Jr et al., Cancer: Principles & Practice of Oncology, 3d ed, p1471) Carcinoma, Basal Cell, Pigmented,Epithelioma, Basal Cell,Rodent Ulcer,Ulcer, Rodent,Basal Cell Carcinoma,Basal Cell Carcinomas,Basal Cell Epithelioma,Basal Cell Epitheliomas,Carcinomas, Basal Cell,Epitheliomas, Basal Cell,Rodent Ulcers,Ulcers, Rodent
D002294 Carcinoma, Squamous Cell A carcinoma derived from stratified SQUAMOUS EPITHELIAL CELLS. It may also occur in sites where glandular or columnar epithelium is normally present. (From Stedman, 25th ed) Carcinoma, Epidermoid,Carcinoma, Planocellular,Carcinoma, Squamous,Squamous Cell Carcinoma,Carcinomas, Epidermoid,Carcinomas, Planocellular,Carcinomas, Squamous,Carcinomas, Squamous Cell,Epidermoid Carcinoma,Epidermoid Carcinomas,Planocellular Carcinoma,Planocellular Carcinomas,Squamous Carcinoma,Squamous Carcinomas,Squamous Cell Carcinomas
D004224 Diterpenes Twenty-carbon compounds derived from MEVALONIC ACID or deoxyxylulose phosphate. Diterpene,Diterpenes, Cembrane,Diterpenes, Labdane,Diterpenoid,Labdane Diterpene,Norditerpene,Norditerpenes,Norditerpenoid,Cembranes,Diterpenoids,Labdanes,Norditerpenoids,Cembrane Diterpenes,Diterpene, Labdane,Labdane Diterpenes
D005260 Female Females
D000818 Animals Unicellular or multicellular, heterotrophic organisms, that have sensation and the power of voluntary movement. Under the older five kingdom paradigm, Animalia was one of the kingdoms. Under the modern three domain model, Animalia represents one of the many groups in the domain EUKARYOTA. Animal,Metazoa,Animalia

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