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Metabolism of diethylstilbestrol: Identification of a catechol derived from dienestrol
Author(s) -
Weidenfeld Josef,
Carter Priscilla,
Reinhold Ver N.,
Tanner S. B.,
Engel Lewis L.
Publication year - 1978
Publication title -
biomedical mass spectrometry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.475
H-Index - 121
eISSN - 1096-9888
pISSN - 0306-042X
DOI - 10.1002/bms.1200051008
Subject(s) - diethylstilbestrol , catechol , chemistry , phenazine , catechol oxidase , tyrosinase , potassium periodate , periodate , enzyme , quinone , organic chemistry , biochemistry , peroxidase , catalysis , polyphenol oxidase , hormone
The enzymatic oxidation of E ‐3,4‐bis‐( p ‐hydroxyphenyl)‐hex‐3‐ene (diethylstilbestrol) by either mushroom tyrosinase or rat liver microsomes in the presence of NADPH and air yields a catechol. Upon further oxidation of both compounds with periodate and condensation of the resulting o ‐quinones with o ‐phenylenediamine, phenazines are produced. The phenazines derived from the products of both the plant and animal enzyme systems are identical to the product obtained by oxidation of diethylstilbestrol with potassium nitrosodisulfonate and condensation of the o ‐quinone produced with o ‐phenylenediamine. High and low resolution mass spectra of the phenazine are consistent with its derivation from a catechol having two fewer hydrogens than diethylstilbestrol.