Abstract
Benzoquinones such as primin (2-methoxy-6-pentyl-1,4-benzoquinone) from Primula obconica HANCE (Primulaceae) are known to be strong sensitizers and thus the source of severe allergic contact dermatitis (cell-mediated type of allergy). In order to determine the relationship between sensitizing capacity and chemical structure the synthesis of 19 side-chain-modified analogues of primin was carried out. With each of these primin derivatives 10 guinea pigs were sensitized using a modified FCA-method (FCA = Freund’s complete adjuvant). Elicitation was done open epicutaneously with 0.001 molar concentrations. In these sensitization experiments 2-methoxy-6-alkyl-1,4-benzoquinones (chain length C1-C15) showed ascending sensitizing potency with increasing number of the side chain carbon atoms reaching maximum activity at an alkyl chain of 10 to 11 carbons. Beyond this point a decrease of the sensitizing potency in correlation with a further prolongation of the side chain was observed.
Published Version (
Free)
Talk to us
Join us for a 30 min session where you can share your feedback and ask us any queries you have
Schedule a call