Genistein
Genistein.png

Genistein is an isoflavone (a type of flavonoid) found in several plants including kudzu and soybeans. It often appears along with daidzein.

Kudzu root was found to contain 12.6 mg/100 g dry weight of genistein and 184 mg/100 g dry weight of daidzein.[9]

Soybeans were fount to contain 26.8-102.5 mg/100 g dry weight genistein and 10.5-85.0 mg/100 g dry weight of daidzein.[9]

A typical dietary supplement dosage of genistein for adults ranges from 8mg to 250mg twice daily. No established recommended supplement dosage exists. In several clinical trials up to 600mg were safely used in human test subjects, displaying no toxic side effects.


Metabolism

In vitro tests using human liver microsomes determined that genistein is oxidized by CYP1A2 and to a lesser degree by CYP2E1 to form Orobol (3'-hydroxy genistein).[18]

Genistein CYP1A2 Orobol
Genistein.png —-> 3-hydroxy_genistein.png

Interaction with Psychedelic Compounds

Some anecdotal reports indicate that whole kudzu extracts reduce the effects of psychedelics. Unlike whole kudzu which contains puerarin, a compound that interacts with 5-HT2C[15] and also may interact with either 5-HT1A or 5-HT2A receptors[14], genistein has not been shown to be active at 5-HT1A, 5-HT2A, or 5-HT2C receptors.


Effects on Enzymes

17bHSD Effect Dosage Verified in Humans
17bHSD2 (Oxidative form of 17bHSD) 77% Induction[1] ? ?
17bHSD1 (Reductive form of 17bHSD) Inhibition[13] ? ?
UGT Effect Dosage Verified in Humans
UGT1A1 96.7% Inhibition[2] 30 μM ?
UGT1A3 47.4% Inhibition[2] 30 μM ?
UGT1A9 79.5% Inhibition[2] 30 μM ?
UGT2B7 30% Inhibition[2] 30 μM ?
SULT Effect Dosage Verified in Humans
SULT1A1 Potent inhibition[3][4] ? ?
SULT1A3 50% inhibition[8] > 25000 nM ?
P-Glycoprotein Effect Dosage Verified in Humans
P-Glycoprotein Inhibition[5] ? ?
ADH Effect Dosage Verified in Humans
ADH Potent inhibition[6] ? ?
GST Effect Dosage Verified in Humans
GSTM1-1 Inhibition[7] ? ?
GSTM2-2 Inhibition[7] ? ?
Cytochrome P450 Effect Dosage Verified in Humans
CYP3A Modest Induction 14 day treatment Yes[11]
CYP3A4 (a subset of CYP3A) Induction[12] ? ?
CYP1A2 41% Inhibition 1 gram daily for 14 days Yes[10]
CYP2A6 47% Induction 1 gram daily for 14 days Yes[10]
CYP2E1 Potent inhibition[16][17][19] ? ?

Chemical Properties

PubChem Compound ID: 5280961
Molecular Weight: 270.2369 [g/mol]
Molecular Formula: C15H10O5
XLogP3-AA: 2.7
H-Bond Donor: 3
H-Bond Acceptor: 5
IUPAC Name: 5,7-dihydroxy-3-(4-hydroxyphenyl)chromen-4-one
InChI: InChI=1S/C15H10O5/c16-9-3-1-8(2-4-9)11-7-20-13-6-10(17)5-12(18)14(13)15
(11)19/h1-7,16-18H
InChIKey: TZBJGXHYKVUXJN-UHFFFAOYSA-N
Canonical SMILES: C1=CC(=CC=C1C2=COC3=CC(=CC(=C3C2=O)O)O)O
Melting point: 301.5 dec °C


See Also


Bibliography
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