Interaction of lignans with human sex hormone binding globulin (SHBG)

Z Naturforsch C J Biosci. Nov-Dec 1997;52(11-12):834-43.

Abstract

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.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Binding, Competitive
  • Furans / chemical synthesis
  • Furans / chemistry
  • Furans / metabolism
  • Humans
  • Kinetics
  • Lignans / chemical synthesis
  • Lignans / chemistry
  • Lignans / metabolism*
  • Lignin / chemical synthesis
  • Lignin / chemistry
  • Lignin / metabolism
  • Molecular Structure
  • Nuclear Magnetic Resonance, Biomolecular
  • Sex Hormone-Binding Globulin / chemistry
  • Sex Hormone-Binding Globulin / metabolism*
  • Structure-Activity Relationship

Substances

  • 3,4-divanillyltetrahydrofuran
  • Furans
  • Lignans
  • Sex Hormone-Binding Globulin
  • Lignin