lignans interfere with dihydrotestosterone

Doug Skrecky (
Wed, 24 Jun 1998 19:03:22 -0700 (PDT)

Schottner M. Spiteller G. Gansser D.
Lehrstuhl fur organische Chemie, Universitat Bayreuth, Germany.
Lignans interfering with 5 alpha-dihydrotestosterone binding to human sex
hormone-binding globulin.
Journal of Natural Products. 61(1):119-21, 1998 Jan.
The natural lignans (-)-3,4-divanillyltetrahydrofuran (1), (-)-matairesinol
(2), (-)-secoisolariciresinol (3), (+/-)-enterolactone (4),
(+/-)-enterodiol (5), and nordihydroguaiaretic acid (NDGA) (6) reduce the
binding of 3H-labeled 5 alpha-dihydrotestosterone (DHT) to human sex
hormone-binding globulin (SHBG). (-)-3,4-Divanillyltetrahydrofuran (1) has
the highest binding affinity (Ka = 3.2 +/- 1.7 x 10(6)M-1) of all lignans
investigated so far; the reversibility of its binding and a double reciprocal
plot suggest a competitive inhibition of the SHBG-DHT interaction. Increasing
hydrophobity in the aliphatic part of the lignans
(butane-1,4-diol-butanolide-tetrahydrofuran structures) leads to higher
binding affinity. In the aromatic part, a 3-methoxy-4-hydroxy substitution
pattern is most effective for binding to SHBG.

Additional note by poster:

Given the above there exists a theoretical possibility that regular
flax consumption could slow the progress of male pattern baldness.