Naringenin is a flavonoid found in white grapefruit in large amounts and is partially responsible for its effects on enzymes.

Blocking Psychedelic Action of Allylbenzenes

Anecdotal reports indicate that pre-treatment with 20 mg naringenin or 2 cups of white grapefruit juice containing large amounts of naringenin can block or delay the onset of the psychedelic effects of allylbenzenes by 4-8 hours.

Naringenin is known to potently inhibit oxidative Estradiol 17beta-dehydrogenase Type 2.

Allylbenzenes require oxidation by Estradiol 17beta-dehydrogenase Type 2 before they can form 1'-oxo metabolites (such as 1'-oxoestragole from methyl chavicol). Many studies on PubMed indicate that only the 1'-oxo metabolites of allylbenzenes are able to form alkaloids.

See the articles Estradiol 17beta-dehydrogenase Type 2, Oilahuasca Activation, 1'-oxoestragole, and 1'-oxosafrole for more information.

Effects on Enzymes

Sulfotransferase Interaction Dosage Verified in Man
SULT1A1 Significant inhibition[2] ? ?
SULT1A3 Partial inhibition[2] ? ?
Monoamine Oxidase Interaction Dosage Verified in Man
MAO-B Moderate Inhibition IC50=288 µM[1] ?
P-Glycoprotein Interaction Dosage Verified in Man
P-Ggp Inhibition [3] ? ?
Xanthine Oxidase Interaction Dosage Verified in Man
XO Moderate Inhibition IC50=50-100 μM[4] ?
17bHSD2 Interaction Dosage Verified in Man
Oxidative 17bHSD2 50% inhibition IC50=14.4 µM[5] ?


Chemical Properties

PubChem Compound ID: 932
Molecular Weight: 272.25278 [g/mol]
Molecular Formula: C15H12O5
XLogP3-AA: 2.4
H-Bond Donor: 3
H-Bond Acceptor: 5
IUPAC Name: 5,7-dihydroxy-2-(4-hydroxyphenyl)-2,3-dihydrochromen-4-one
InChI: InChI=1S/C15H12O5/c16-9-3-1-8(2-4-9)13-7-12(19)15-11(18)5-10(17)6-14(15)
Canonical SMILES : C1C(OC2=CC(=CC(=C2C1=O)O)O)C3=CC=C(C=C3)O

1. Anna K. Jäger and Lasse Saaby;
Flavonoids and the CNS; Molecules 2011, 16, 1471-1485; doi:10.3390/molecules16021471; ISSN 1420-3049; (Download Attached PDF Document)
2. Inhibitory effects of various beverages on human recombinant sulfotransferase isoforms SULT1A1 and SULT1A3.
Nishimuta H, Ohtani H, Tsujimoto M, Ogura K, Hiratsuka A, Sawada Y. PubMed PMID: 17876860
3. Emerging Significance of Flavonoids as P-Glycoprotein Inhibitors in
Cancer Chemotherapy Tripta Bansal, Manu Jaggi, Roop K Khar and Sushama Talegaonkar; J Pharm Pharmaceut Sci (www. 12 (1): 46 - 78, 2009 (Download Attached PDF Document)
4. On-chip assay for determining the inhibitory effects and modes of action of drugs against xanthine oxidase.
Naoghare PK, Kwon HT, Song JM. PubMed PMID: 19679420
5. Discovery of nonsteroidal 17beta-hydroxysteroid dehydrogenase 1 inhibitors by pharmacophore-based screening of virtual compound libraries.
Schuster D, Nashev LG, Kirchmair J, Laggner C, Wolber G, Langer T, Odermatt A. PubMed: 18533708
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