ISSN:
1432-2048
Keywords:
Brugmansia (root, alkaloid)
;
Datura (root, alkaloid)
;
(RS)-phenyl [1,3-13C2]lactic acid
;
Root culture (alkaloid production)
;
Phenyllactic acid (2-hydroxy-3-phenylpropanoic acid)
;
Tropic acid [2-hydroxymethyl-2-phenylacetic acid]
;
Tropine (tropan-3α-ol)
Source:
Springer Online Journal Archives 1860-2000
Topics:
Biology
Notes:
Abstract (S)-(-)-Tropic acid is the acidic moiety of the tropane ester alkaloids, hyoscyamine and scopolamine (hyoscine). When tropic acid is fed to transformed root cultures of Datura stramonium L. or a Brugmansia (Datura) Candida x B. aurea hybrid, the formation of these alkaloids is inhibited. Phenyllactic acid, from which the tropoyl moiety is derived, is considerably less inhibitory. Label from (RS)-phenyl[1,3-13C2]lactic acid is incorporated at high levels into apoatropine, littorine, aposcopolamine, hyoscyamine, 7β-hydroxyapoatropine, scopolamine and 7β-hydroxyhyoscyamine when fed to these cultures. The presence of an excess concentration of unlabelled tropic acid has little influence on the specific incorporation into these products. It is concluded that free tropic acid is not an intermediate in hyoscyamine biosynthesis but rather that the rearrangement of phenyllactic acid occurs subsequent to its esterification.
Type of Medium:
Electronic Resource
URL:
http://dx.doi.org/10.1007/BF00201038
