8-THIABICYCLO[3.2.1]OCTAN-3-ONE AS A BIOCHEMICAL TOOL IN THE STUDY OF TROPANE ALKALOID BIOSYNTHESIS

被引：16

作者：

PARR, AJ ^{[1
]}

WALTON, NJ ^{[1
]}

BENSALEM, S ^{[1
]}

MCCABE, PH ^{[1
]}

ROUTLEDGE, W ^{[1
]}

机构：

[1] UNIV GLASGOW, DEPT CHEM, GLASGOW G12 8QQ, SCOTLAND

来源：

PHYTOCHEMISTRY | 1991年 / 30卷 / 08期

关键词：

DATURA-STRAMONIUM; SOLANACEAE; BIOSYNTHESIS; INHIBITOR; TROPANE ALKALOIDS; TROPINE; PSEUDOTROPINE; 8-THIABICYCLO[3.2.1]OCTAN-3-ONE;

D O I：

10.1016/0031-9422(91)85108-C

中图分类号：

Q5 [生物化学]; Q7 [分子生物学];

学科分类号：

071010 ; 081704 ;

摘要：

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 3-alpha-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.

引用

页码：2607 / 2609

页数：3

共 15 条

[11]

RHODES MJC, 1989, PRIMARY SECONDARY ME, V2, P58

[12]

ROBINS RJ, 1990, PLANTA, V181, P414, DOI 10.1007/BF00195896

[13] STUDIES ON THE BIOSYNTHESIS OF TROPANE ALKALOIDS IN DATURA-STRAMONIUM L TRANSFORMED ROOT CULTURES .1. THE KINETICS OF ALKALOID PRODUCTION AND THE INFLUENCE OF FEEDING INTERMEDIATE METABOLITES [J].