Phytochemistry p. 2607 - 2609 (1991)
Update date:2022-08-11
Topics:
Parr, Adrian J.
Walton, Nick J.
Bensalem, Smail
McCabe, Peter H.
Routledge, William
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
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