12-deoxyphorbol

Tigliane (G5 C7 C61 C3) diterpenes include the highly irritant, toxic, co-carcinogenic, PKC activating phorbol esters from Euphorbiaceae plants. While not being activated by the parent compound phorbol, PKC is activated by plant-derived esters of phorbol, 4-deoxyphor-bol and 12-deoxyphorbol (e.g. 12-0-palmitoyl-16-hydroxy-phorbol 13-acetate, 12-deoxyphorbol 13-benzoate, 12-deoxyphorbol 13-phenylacetate, 12-deoxyphorbol 13-phenylacetate-20-acetate, sapintoxin A (4-deoxyphorbol 12-(2-methylamino)benzoate-l3-acetate) and 12-tetradecanoylphorbol 13-acetate (TPA)), as well as by synthetic phorbol esters. 

Deoxyphorbol 13-phenylacetate (phorbol ester tigliane diterpene)... 

Deoxyphorbol-13 -G-phenylacetate-20-acetate = Epidermal growth factor... 

The biogenetic structural relationships and structure-activity relationships of the diterpenoid skin irritants and co-carcinogens of the Euphorbiaceae and Thymelaceae have been described in a number of reviews.Baliospermum montanum (Euphorbiaceae) contains the orthoester montanin (111) and baliospermin (112) together with some 12-deoxyphorbol-13-esters. A number of new highly irritant 1-alkyl-daphnane orthoester derivatives [(113) and the corresponding 3-ketone] have been obtained from the Thymelaceae. The Chinese... 

Similar mixtures of compounds are found in many species of the genus Euphorbia as well as in other species of the Euphorbiaceae. 12-Deoxyphorbol (20) is one of the most common toxic diterpenoids in latex. This compound nor-... 

Deoxyphorbol-13-0-phenylacetate-20-acetate is not protein kinase C-P isozyme-selective in vivo (Kiley et al. 1994). Prolonged treatment (>6h) of cultures in down-modulation studies is complicated by the metabolism of 12-deoxyphorbol-13-0-phenylacetate-20-acetate to 12-deoxyphorbol-13-phenylacetate, a compound which activates all protein kinase C isozymes tested in vitro (Ryves et al. 1991). 

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