8-THIABICYCLOOCTAN-3-ONE AS A BIOCHEMICAL TOOL IN THE STUDY OF TROPANE ALKALOID BIOSYNTHESIS

Article abstract of DOI:10.1016/0031-9422(91)85108-C

8-Thiabicyclo<3.2.1>octan-3-one, the sulphur analogue (replacing the methylaza bridge) of tropinone, was fed to Datura stramonium transformed root cultures.The compound was metabolized to a large degree.Notable products included the reduction product, 8-thiabicyclo<3.2.1>octan-3-ol, analogous to tropine, and also the derived 3-O-acetyl ester.In addition, tropane alkaloid synthesis was perturbed.Hyoscyamine levels, and in particular tropine and 3α-acetoxytropane levels, were reduced.Pseudotropine, on the other hand, was found to increase in concentration.It is concluded that 8-thiabicyclo<3.2.1>octan-3-one may be a good biochemical tool in the study of tropane alkaloid biosynthesis.Key Word Index -Datura stramonium; Solanaceae; biosynthesis; inhibitor; tropanealkaloids; tropine; pseudotropine; 8-thiabicyclo<3.2.1>octan-3-one