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.
D000818:Animals; D019751:Intramolecular Transferases; D007535:Isomerases / Q000037:antagonists & inhibitors*; D007546:Isoquinolines / Q000494:pharmacology*; D007700:Kinetics; D008861:Microsomes / Q000201:enzymology; D008862:Microsomes, Liver / Q000201:enzymology; D010944:Plants / Q000201:enzymology; D051381:Rats; D013045:Species Specificity; D013261:Sterols / Q000096:biosynthesis; D003313:Zea mays / Q000201:enzymology
D007546:Isoquinolines; D013261:Sterols; C049832:MDL 28815; D007535:Isomerases; D019751:Intramolecular Transferases; C021924:lanosterol synthase; C021923:cycloartenol synthase