68236-11-3
Chemical Structure
6,8-Diprenylnaringenin
Synonym(s): Lonchocarpol A; Senegalensin
- CAS No.: 68236-11-3
- Formula:C25H28O5
- Molecular Weight:408.49
IUPAC Name: (S)-5,7-dihydroxy-2-(4-hydroxyphenyl)-6,8-bis(3-methylbut-2-en-1-yl)chroman-4-one
InChIKey: HCNLDGTUMBOHKT-NRFANRHFSA-N
SMILES: O=C1C[C@H](OC2=C(C(O)=C(C(O)=C12)C/C=C(C)\C)C/C=C(C)\C)C3=CC=C(C=C3)O
Biological Activity: 6,8-Diprenylnaringenin (Lonchocarpol A; Senegalensin) is a potent BCRP/ABCG2 inhibitor (IC50 = 0.410 μM) and a non-competitive allosteric PTP1B inhibitor (IC50 = 1.04 μM; Ki = 1.56 μM) that is isolated from Humulus lupulus. 6,8-Diprenylnaringenin produces non-competitive allosteric inhibition by locking the WPD catalytic loop of PTP1B in an inactive open conformation, while simultaneously binding to and inhibiting the ABCG2 drug efflux pump. 6,8-Diprenylnaringenin also exhibits antibacterial activity against MRSA (MIC = 6-13 μM) and antioxidant activity. 6,8-Diprenylnaringenin is used in research on type 2 diabetes, obesity, MRSA infection, and atherosclerosis[1][2][3][4][5].
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6,8-Diprenylnaringenin | 6,8-Diprenylnaringenin (Lonchocarpol A; Senegalensin) is a potent BCRP/ABCG2 inhibitor (IC50 = 0.410 μM) and a non-competitive allosteric PTP1B inhibitor (IC50 = 1.04 μM; Ki = 1.56 μM) that is isolated from Humulus lupulus. 6,8-Diprenylnaringenin produces non-competitive allosteric inhibition by locking the WPD catalytic loop of PTP1B in an inactive open conformation, while simultaneously binding to and inhibiting the ABCG2 drug efflux pump. 6,8-Diprenylnaringenin also exhibits antibacterial activity against MRSA (MIC = 6-13 μM) and antioxidant activity. 6,8-Diprenylnaringenin is used in research on type 2 diabetes, obesity, MRSA infection, and atherosclerosis. | |||||||||||||||||||||
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References
- [1]. Kamel EM, et al. Repurposing dual-C-prenylated flavonoids as potent allosteric inhibitors of PTP1B: Integrated phytochemical, enzymological, and in silico evidence. International journal of biological macromolecules. 2025 Jun;316(Pt 1):144808.
- [2]. Ritsema JH. Effective membrane permeabilization of methicillin-resistant Staphylococcus aureus by prenylated phenolics. Journal of Natural Products. 2025 Aug 19;88(9):2065.
- [3]. Miranda CL, et al. Antioxidant and prooxidant actions of prenylated and nonprenylated chalcones and flavanones in vitro. Journal of agricultural and food chemistry. 2000 Sep;48(9):3876-84.
- [4]. Tan KW, et al. Hop-derived prenylflavonoids are substrates and inhibitors of the efflux transporter breast cancer resistance protein (BCRP/ABCG2). Molecular nutrition & food research. 2014 Nov;58(11):2099-110. [Content Brief]
- [5]. Coldham NG, et al. Identification, quantitation and biological activity of phytoestrogens in a dietary supplement for breast enhancement. Food and chemical toxicology : an international journal published for the British Industrial Biological Research Association. 2001 Dec;39(12):1211-24.
