Zeitschrift für Naturforschung C · 1997 · 31 citations · 2 references
Life SciencesBiochemistryPharmacologyHormone BiochemistryReproductive EndocrinologyStructure-activity RelationshipsGonadal HormonesGonadal Steroid HormonesHormone Binding ProteinsHormone StructureLigand BindingStructure-activity Relationship AnalysisAndrogen Binding GlobulinHormone Binding AffinityHormone Structure-function RelationshipsSex Hormone PharmacologySex Hormone-binding GlobulinStructural Basis Of Hormone BindingStructure-activity Relationships Of HormonesSubstitution Pattern Analysis
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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John B. Grutzner · Analytical Biochemistry · 1987 · 998 citations
Biological activities of lignans
W.Donald MacRae, G.H.N. Towers · Phytochemistry · 1984 · 561 citations