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Chalcone constituents pulincisones A-F isolated from Pulicaria incisa with NQO1 inducer activity
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Chalcone constituents pulincisones A-F isolated from Pulicaria incisa with NQO1 inducer activity
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Journal Article
Chalcone constituents pulincisones A-F isolated from Pulicaria incisa with NQO1 inducer activity
2025
Overview
Previously unknown chalcones such as
β
’-chalcanone-
α
,
β
-diols and a
β
-hydroxydihydrochalcone, named pulincisone A-F as well as known chalcone analogs 3,4,2’,4’,6’,7,8-heptahydroxy-7(8)-dihydrochalcone (
7
) and 4,2’,6’-trihydroxy-4’-methoxydihydrochalcone (
8
) were isolated from
Pulicaria incisa
(Lam.) DC. and assayed for cancer preventative activity. Structures were identified by spectroscopic methods, including HRESIMS, 1D and 2D NMR experiments. Pulincisone A and B, are epimers, at stereocenter C-8. A structural revision resulted in pulicisone A (
1
) and D (
4
) replacing pulichalconoids B and C, that were previously reported from the same species. Isolated chalcones were assessed for chemopreventive potential as inducers of NAD(P)H: quinone oxidoreductase 1 (NQO1). Compounds
2
,
3
,
5
, and
6
induced NQO1, using a Prochaska assay. NQO1 protein expression was detected by Western blotting analysis. Compound
6
among four active compounds had the highest potency as NQO1 inducers. Molecular docking analysis of the NQO1 Keap1 Kelch domain suggests Nrf2-dependent induction. These data indicate that pulincisone F (
6
) is a promising bioactive antioxidant (NQO1-inducer) with superior docking scores with the Keap1-Nrf2 complex compared to the reference NQO1 inducer sulforaphane (− 8.26 versus − 5.08 kcal mol
-
, respectively).
Publisher
Nature Publishing Group UK,Nature Publishing Group,Nature Portfolio
Subject
/ Chalcone - isolation & purification
/ Chalcones - isolation & purification
/ Genes
/ Humanities and Social Sciences
/ Humans
/ Kelch-Like ECH-Associated Protein 1 - chemistry
/ Kelch-Like ECH-Associated Protein 1 - metabolism
/ Molecular Docking Simulation
/ NAD(P)H Dehydrogenase (Quinone) - metabolism
/ NF-E2-Related Factor 2 - metabolism
/ NQO1
/ Proteins
/ Science
