A prenylated flavonoid with diverse biological activities
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(2S)-6-Prenylnaringenin

Item No. 35138

Product Insert (PDF)Safety Data Sheet (SDS) (PDF)
Technical Information
Formal Name
(2S)-2,3-dihydro-5,7-dihydroxy-2-(4-hydroxyphenyl)-6-(3-methyl-2-buten-1-yl)-4H-1-benzopyran-4-one
CAS Number
68236-13-5
Synonyms
  • (2S)-6-PN
Molecular Formula
C20H20O5
Formula Weight
340.4
Purity
≥98%
Formulation
A solid
Solubility(Learn about Variance in Solubility)
DMSO: Soluble
λmax
215, 295 nm
SMILES
OC1=C2C(O[C@H](C3=CC=C(C=C3)O)CC2=O)=CC(O)=C1C/C=C(C)\C
InChi Code
InChI=1S/C20H20O5/c1-11(2)3-8-14-15(22)9-18-19(20(14)24)16(23)10-17(25-18)12-4-6-13(21)7-5-12/h3-7,9,17,21-22,24H,8,10H2,1-2H3/t17-/m0/s1
InChi Key
YHWNASRGLKJRJJ-KRWDZBQOSA-N
Origin
Plant/Humulus lupulus
Shipping & Storage Information
Storage
-20°C
Shipping
Room temperature in continental US; may vary elsewhere
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    1 mg

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    Product Description

    (2S)-6-Prenylnaringenin is a prenylated flavonoid that has been found in the hop plant, H. lupulus, and has diverse biological activities.1,2 It inhibits the T-type voltage-gated calcium (Cav) channel Cav3.2 in HEK293 cells and high-voltage-activated calcium currents in differentiated NG 108-15 cells in whole-cell patch-clamp assays (IC50s = 0.928 and 2.005 µM, respectively).1 (2S)-6-Prenylnaringenin reduces the activity of aldose reductase 2 (ALR2; IC50 = 6.2 µM for the recombinant human enzyme).2 It reduces mechanical allodynia in a mouse model of sodium hydrosulfide-induced somatic pain when administered at a dose of 10 pmol/paw.1

    WARNING This product is not for human or veterinary use.

    References & Product Citations
    Product Description References

    1. Sekiguchi, F., Fujita, T., Deguchi, T., et al. Blockade of T-type calcium channels by 6-prenylnaringenin, a hop component, alleviates neuropathic and visceral pain in mice. Neuropharmacology 138, 232-244 (2018).

    2. Shim, S.H., Kim, Y., Lee, J.Y., et al. Aldose reductase inhibitory activity of the compounds from the seed of Psoralea corylifolia. J. Korean Soc. Appl. Biol. Chem. 52(5), 568–572 (2009).