Schöttner, M.; Ganßer, D.; Spiteller, G.: Interaction of lignans with human sex hormone binding globulin (SHBG). In: Zeitschrift für Naturforschung - Section C Journal of Biosciences 52 (1997), Nr. 11-12, S. 834-843. DOI:
https://doi.org/10.1515/znc-1997-11-1218
Zusammenfassung: |
Lignans bind to sex hormone-binding globulin (SHBG). The lignan with the highest binding affinity is (±)-3,4-divanillyltetrahydrofuran. In a double Stobbe condensation - without use of protecting groups - a wide variety of lignans with different substitution pattern in the aromatic and aliphatic part of the molecule was synthesized. These lignans were tested in a SHBG-binding assay which allowed to deduce the following relationship between structure and activity: 1) (±)-diastereoisomers are more active than meso compounds 2.) the 4-hydroxy-3-methoxy (guajacyl) substitution pattern in the aromatic part is most effective 3.) the activity increases with the decline in polarity of the aliphatic part of the molecule.
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Lizenzbestimmungen: |
CC BY-NC-ND 3.0 Unported - https://creativecommons.org/licenses/by-nc-nd/3.0/
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Publikationstyp: |
Article |
Publikationsstatus: |
publishedVersion |
Erstveröffentlichung: |
1997 |
Schlagwörter (englisch): |
Sex Hormone Binding Globulin, SHBG (SBP), Stobbe Condensation, Synthesis of Lignans, 3,4 divanillyltetrahydrofuran, 3,4-divanillyltetrahydrofuran, furan derivative, lignan, lignin, sex hormone binding globulin, article, binding competition, chemical structure, chemistry, human, kinetics, metabolism, nuclear magnetic resonance, structure activity relation, synthesis, Binding, Competitive, Furans, Humans, Kinetics, Lignans, Lignin, Molecular Structure, Nuclear Magnetic Resonance, Biomolecular, Sex Hormone-Binding Globulin, Structure-Activity Relationship
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Fachliche Zuordnung (DDC): |
570 | Biowissenschaften, Biologie
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