N-[(1,5,9)-trimethyl-decyl]-4 alpha,10-dimethyl-8-aza-trans-decal-3 beta-ol a novel potent inhibitor of 2,3-oxidosqualene cycloartenol and lanosterol cyclases.

N-[(1,5,9)-trimethyl-decyl)]-4 alpha,10-dimethyl-8-aza-trans-decal-3 beta-ol 9 was designed to mimic the C9 or C8 high energy carbocationic intermediates postulated during the enzymic cyclization of 2,3-oxidosqualene to different triterpenes. The structurally new molecule 9 inhibits strongly cycloartenol and lanosterol cyclases in maize seedlings and rat liver microsomes respectively, whereas it does not inhibit beta-amyrin cyclase in the plant system. For the first time 2,3-oxidosqualene cycloartenol cyclase and beta-amyrin cyclase have been differentiated in the same plant material by use of a specific inhibitor.