Electronic Supplementary Material
Phase II metabolism of the soy isoflavones genistein and daidzein in humans, rats and mice: a cross-species and sex comparison
Sebastian T. Soukup1, Jussi Helppi2, Dennis R. Müller3, Oliver Zierau4, Bernhard Watzl5, Günter Vollmer4, Patrick Diel3, Achim Bub5, Sabine E. Kulling1
1
Department of Safety and Quality of Fruit and Vegetables, Max Rubner-Institut, Karlsruhe,
Germany 2
Max Planck Institute of Molecular Cell Biology and Genetics, Dresden, Germany
3
Department of Molecular and Cellular Sports Medicine, Institute for Cardiovascular
Research and Sports Medicine, German Sport University, Cologne, Germany 4
Molecular Cell Physiology and Endocrinology, Institute for Zoology, Technische Universität
Dresden, Dresden, Germany 5
Department of Physiology and Biochemistry of Nutrition, Max Rubner-Institut, Karlsruhe,
Germany
Corresponding author: Prof. Dr. Sabine E. Kulling, Department of Safety and Quality of Fruit and Vegetables, Max Rubner-Institut, Haid-und-Neu-Straße 9, 76131 Karlsruhe, Germany, phone +49 721 6625 500, fax +49 721 6625 453, email:
[email protected]
Supplemental Data 1. Chemical structures of the quantified isoflavone analytes.
R1 O
R1 O
O
7
4'
O
O
R1 O 7
> > > > > > > > >
O R2
Genistein (GEN) and conjugates R1, R2 = H, G, or S
O
O
O O
OH
G = glucuronic acid group R2=H R2=H R2=G R2=G R2=H R2=S R2=S R2=S R2=G
4'
O
OH
OH HO
R1=H, R1=G, R1=H, R1=G, R1=S, R1=H, R1=S, R1=G, R1=S,
OH
O R2
Daidzein (DAI) and conjugates R1, R2 = H, G, or S
O
7
DAI (aglycone) DAI-7-G DAI-4‘-G DAI-7,4‘-DG DAI-7-S DAI-4‘-S DAI-7,4‘-DS DAI-7-G-4’-S DAI-4’-G-7-S
S O O
S = sulfate group R1=H, R1=G, R1=H, R1=G, R1=S, R1=H, R1=S, R1=G, R1=S,
R2=H R2=H R2=G R2=G R2=H R2=S R2=S R2=S R2=G
> > > > > > > > >
GEN (aglycone) GEN-7-G GEN-4‘-G GEN-7,4‘-DG GEN-7-S GEN-4‘-S GEN-7,4‘-DS GEN-7-G-4’-S GEN-4’-G-7-S
O
4'
Equol and conjugates R1, R2 = H, G, or S
O R2
R1=H, R2=H > R1=G, R2=H > R1=S, R2=H >
Equol (aglycone) Equol-7-G Equol-7-S
Supplemental Data 2. Concentration of isoflavones in the soy extract enriched animal diet. Concentration [mg/g diet]
RSD [%]
Relative composition [%]
Daidzein
0.017
1.1
2.5
Daidzin
0.270
2.3
39.9
6''-O-Acetyl-Daidzin
0.020
2.1
2.9
Analytes
6''-O-Malonyl-Daidzin
n.d.
0.0
Genistein
0.010
4.6
1.5
Genistin
0.335
1.9
49.6
6''-O-Acetyl-Genistin
0.025
1.9
3.6
6''-O-Malonyl-Genistin
n.d.
0.0
Sum of all analytes
0.676
1.9
Sum of Daidzein in aglycone equivalents
0.192
2.1
Sum of Genistein in aglycone equivalents
0.234
1.7
Aglycone equivalents DAI + GEN
0.426
1.9
100.0
Mean of six determinations; RSD, relative standard deviation; n.d. not detected (6''-Omalonyl-daidzin
