Polyporenic Acids from the Mushroom Buglossoporus quercinus Possess Chemosensitizing and Efflux Pump Inhibitory Activities on Colo 320 Adenocarcinoma Cells

Author:

Felegyi Kristóf1,Garádi Zsófia12ORCID,Rácz Bálint3ORCID,Tóth Gábor34,Papp Viktor5,Boldizsár Imre16ORCID,Dancsó András2ORCID,Spengler Gabriella3ORCID,Béni Szabolcs17,Ványolós Attila1ORCID

Affiliation:

1. Department of Pharmacognosy, Semmelweis University, 1085 Budapest, Hungary

2. Directorate of Drug Substance Development, Egis Pharmaceuticals Plc., 1475 Budapest, Hungary

3. Albert Szent-Györgyi Health Center, Department of Medical Microbiology, Albert Szent-Györgyi Medical School, University of Szeged, 6725 Szeged, Hungary

4. ELKH-USZ Biologically Active Natural Products Research Group, University of Szeged, 6720 Szeged, Hungary

5. Department of Botany, Hungarian University of Agriculture and Life Sciences, 1118 Budapest, Hungary

6. Department of Plant Anatomy, Institute of Biology, Eötvös Loránd University, 1117 Budapest, Hungary

7. Department of Analytical Chemistry, Institute of Chemistry, Eötvös Loránd University, 1117 Budapest, Hungary

Abstract

Polyporenic acids N-R (1–5), five novel 24-methylene lanostane triterpenes along with seven known polyporenic acids (6–12), were identified from the fruiting bodies of Buglossoporus quercinus. The isolation of compounds 1–12 was performed by a combination of multistep flash chromatography and reversed-phase high-performance liquid chromatography (HPLC). The structure determination was carried out by extensive spectroscopic analysis, including 1D and 2D nuclear magnetic resonance (NMR) and high-resolution electrospray ionization mass spectrometry (HR-ESI-MS) experiments. The isolated fungal metabolites were investigated for their antiproliferative activity in vitro by 3-(4,5-dimethylthiazol2-yl)-2,5-diphenyltetrazolium bromide (MTT) assay on the resistant Colo 320 human colon adenocarcinoma cell line expressing P-glycoprotein (ABCB1). The lanostane triterpenes exerted moderate antiproliferative activity with IC50 values in the range of 20.7–106.2 μM. A P-glycoprotein efflux pump modulatory test on resistant Colo 320 cells highlighted that fungal metabolites 3, 5, 8, and 10–12 have the ability to inhibit the efflux pump activity of cancer cells. Moreover, the drug interactions of triterpenes with doxorubicin were studied by the checkerboard method. Compounds 3–4, and 7–12 interacted in a synergistic manner, while an outstanding potency was detected for compound 9, which was defined as strong synergism (CI = 0.276). The current study reveals that B. quercinus is a remarkable source of fungal steroids with considerable chemosensitizing activity on cancer cells.

Funder

National Research, Development, and Innovation Fund

Semmelweis Fund for Science and Innovation

National Research, Development and Innovation Office, Hungary

Publisher

MDPI AG

Subject

Plant Science,Ecology, Evolution, Behavior and Systematics,Microbiology (medical)

Reference24 articles.

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2. Highly Modified Lanostane Triterpenes from Fruiting Bodies of the Basidiomycete Tomophagus sp.;Isaka;J. Nat. Prod.,2019

3. Lanostane Triterpenoids with PTP1B Inhibitory and Glucose-Uptake Stimulatory Activities from Mushroom Fomitopsis pinicola Collected in North America;Zhang;J. Agric. Food Chem.,2020

4. Buglossosporus gen. nov.—A new genus of polypores;Pouzar;Czech Mycol.,1966

5. Ryvarden, L., and Gilbertson, R.L. (1994). European Polypores. 2. Meripilus–Tyromyces. Synopsis Fungorum 7, Fungiflora.

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