Mammalian Alkaloids: O‐methylation of (S)‐ and (R)‐dideoxynorlaudanosoline‐1‐carboxylic acid by catechol O‐methyltransferase and identification of a yellow pigment obtained at physiological pH
Authors:
- Maria Danuta Rozwadowska,
- Maria Chrzanowska,
- Arnold Brossi,
- Cyrus R. Creveling,
- Michael E. Bembenek,
- Creed W. Abell
Abstract
O‐Methylation of optically active 3′,4′‐dideoxynorlaudanosoline‐l‐carboxylic acids 1 with O‐methyltransferase in vitro afforded almost exclusively the 7‐O‐methylated acids 3. A similar result was obtained with the yellow quinonemethide 4A obtained from 1 at neutral or slightly alkaline pH by oxidative decarboxylation and affording the 3,4‐dihydroisoquinoline 15 on methylation with catechol O‐methyltransferase (COMT). The structure of quinonemethide 4A was determined on the basis of spectral data, by its conversion into isoquinolines of established structure, and by synthesis. Quinonemethide 4A was found to be a weak inhibitor of monoamine oxidase A (MAO A) but not a substrate. Nonenzymatic oxidative decarboxylation of dopamine‐derived tetrahydroisoquinoline‐l‐carboxylic acids to quinonemethides may be a major factor in biochemical experimentation and should be considered in the interpretation of data. Copyright © 1988 Verlag GmbH & Co. KGaA, Weinheim
- Record ID
- UAM0de9cb8655014b4b9b9c3fa0a78a67f2
- Author
- Journal series
- Helvetica Chimica Acta, ISSN 0018-019X
- Issue year
- 1988
- Vol
- 71
- Pages
- 1598-1607
- ASJC Classification
- ; ; ; ; ;
- DOI
- DOI:10.1002/hlca.19880710703 Opening in a new tab
- Language
- (en) English
- Score (nominal)
- 0
- Score source
- journalList
- Publication indicators
- = 10; = 8; : 1999 = 1.107; : 2006 (2 years) = 1.550 - 2007 (5 years) =1.465
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- Uniform Resource Identifier
- https://researchportal.amu.edu.pl/info/article/UAM0de9cb8655014b4b9b9c3fa0a78a67f2/
- URN
urn:amu-prod:UAM0de9cb8655014b4b9b9c3fa0a78a67f2
* presented citation count is obtained through Internet information analysis and it is close to the number calculated by the Publish or PerishOpening in a new tab system.