Triterpenes and Phenolic Compounds from the Fungus : Isolation, Structure Determination and Biological Activity

Overview

Journal Molecules

Publisher MDPI

Specialty Biology

Date 2021 Apr 3

PMID 33809760

Citations 3

Authors

Zoltan Beni

Miklos Dekany

Andras Sarkozy

Annamaria Kincses

Gabriella Spengler

Viktor Papp

Judit Hohmann

Attila Vanyolos

Affiliations

Soon will be listed here.

Abstract

Investigation of the methanol extract of the poroid fungus resulted in the isolation of a novel triterpene, fuscoporic acid (), together with inoscavin A and its previously undescribed isomer ( and ), 3,4-dihydroxy-benzaldehide (), osmundacetone (), senexdiolic acid (), natalic acid (), and ergosta-7,22-diene-3-one (). The structures of fungal compounds were determined on the basis of NMR and MS spectroscopic analyses, as well as molecular modeling studies. Compounds , - were examined for their antibacterial properties on resistant clinical isolates, and cytotoxic activity on human colon adenocarcinoma cell lines. Compound was effective against Colo 205 (IC 11.65 ± 1.67 µM), Colo 320 (IC 8.43 ± 1.1 µM) and MRC-5 (IC 7.92 ± 1.42 µM) cell lines. Potentially synergistic relationship was investigated between and doxorubicin, which revealed a synergism between the examined compounds with a combination index (CI) at the 50% growth inhibition dose (ED) of 0.521 ± 0.15. Several compounds ( and -) were tested for P-glycoprotein modulatory effect in Colo 320 resistant cancer cells, but none of the compounds proved to be effective in this assay. Fungal metabolites - were evaluated for their antioxidant activity using the oxygen radical absorbance capacity (ORAC) and DPPH assays. Compounds and were found to have a considerable antioxidant effect with EC 0.25 ± 0.01 (DPPH) and 12.20 ± 0.92 mmol TE/g (ORAC) The current article provides valuable information on both the chemical and pharmacological profiles of , paving the way for future studies with this species.

Citing Articles

Antibacterial and Antifungal Activity of Metabolites from Basidiomycetes: A Review.

Lysakova V, Krasnopolskaya L, Yarina M, Ziangirova M Antibiotics (Basel). 2024; 13(11).

PMID: 39596721 PMC: 11591248. DOI: 10.3390/antibiotics13111026.

(Jacq) Bory: Metabolites and Biological Activities.

Vega-Bello M, Moreno M, Estelles-Leal R, Hernandez-Andreu J, Prieto-Ruiz J Molecules. 2023; 28(21).

PMID: 37959736 PMC: 10649588. DOI: 10.3390/molecules28217317.

Triterpenes from as Cytotoxic Agents and Chemosensitizers to Overcome Multidrug Resistance of Cancer Cells.

Yazdani M, Beni Z, Dekany M, Szemeredi N, Spengler G, Hohmann J J Nat Prod. 2022; 85(4):910-916.

PMID: 35293752 PMC: 9040055. DOI: 10.1021/acs.jnatprod.1c01024.

References

Barone G, Gomez-Paloma L, Duca D, Silvestri A, Riccio R, Bifulco G . Structure validation of natural products by quantum-mechanical GIAO calculations of 13C NMR chemical shifts. Chemistry. 2002; 8(14):3233-9. DOI: 10.1002/1521-3765(20020715)8:14<3233::AID-CHEM3233>3.0.CO;2-0. View

Mielnik M, Rzeszutek A, Triumf E, Egelandsdal B . Antioxidant and other quality properties of reindeer muscle from two different Norwegian regions. Meat Sci. 2011; 89(4):526-32. DOI: 10.1016/j.meatsci.2011.05.021. View

Smith S, Goodman J . Assigning stereochemistry to single diastereoisomers by GIAO NMR calculation: the DP4 probability. J Am Chem Soc. 2010; 132(37):12946-59. DOI: 10.1021/ja105035r. View

Sarkozy A, Kusz N, Zomborszki Z, Csorba A, Papp V, Hohmann J . Isolation and Characterization of Chemical Constituents from the Poroid Medicinal Mushroom Porodaedalea chrysoloma (Agaricomycetes) and Their Antioxidant Activity. Int J Med Mushrooms. 2020; 22(2):125-131. DOI: 10.1615/IntJMedMushrooms.2020033698. View

Mo S, Wang S, Zhou G, Yang Y, Li Y, Chen X . Phelligridins C-F: cytotoxic pyrano[4,3-c][2]benzopyran-1,6-dione and furo[3,2-c]pyran-4-one derivatives from the fungus Phellinus igniarius. J Nat Prod. 2004; 67(5):823-8. DOI: 10.1021/np030505d. View

Covino S, DEllena E, Tirillini B, Angeles G, Arcangeli A, Bistocchi G . Characterization of Biological Activities of Methanol Extract of Fuscoporia torulosa (Basidiomycetes) from Italy. Int J Med Mushrooms. 2020; 21(11):1051-1063. DOI: 10.1615/IntJMedMushrooms.2019032896. View

Kincses A, Szabo S, Racz B, Szemeredi N, Watanabe G, Saijo R . Benzoxazole-Based Metal Complexes to Reverse Multidrug Resistance in Bacteria. Antibiotics (Basel). 2020; 9(10). PMC: 7600679. DOI: 10.3390/antibiotics9100649. View

Chou T . Drug combination studies and their synergy quantification using the Chou-Talalay method. Cancer Res. 2010; 70(2):440-6. DOI: 10.1158/0008-5472.CAN-09-1947. View

Deveci E, Tel-Cayan G, Duru M, Ozturk M . Isolation, characterization, and bioactivities of compounds from Fuscoporia torulosa mushroom. J Food Biochem. 2019; 43(12):e13074. DOI: 10.1111/jfbc.13074. View

10.

Chou T . Theoretical basis, experimental design, and computerized simulation of synergism and antagonism in drug combination studies. Pharmacol Rev. 2006; 58(3):621-81. DOI: 10.1124/pr.58.3.10. View

11.

Kovacs B, Zomborszki Z, Orban-Gyapai O, Csupor-Loffler B, Liktor-Busa E, Lazar A . Investigation of Antimicrobial, Antioxidant, and Xanthine Oxidase--Inhibitory Activities of Phellinus (Agaricomycetes) Mushroom Species Native to Central Europe. Int J Med Mushrooms. 2017; 19(5):387-394. DOI: 10.1615/IntJMedMushrooms.v19.i5.10. View

12.

Spengler G, Gajdacs M, Marc M, Dominguez-Alvarez E, Sanmartin C . Organoselenium Compounds as Novel Adjuvants of Chemotherapy Drugs-A Promising Approach to Fight Cancer Drug Resistance. Molecules. 2019; 24(2). PMC: 6359065. DOI: 10.3390/molecules24020336. View

13.

Liu H, Tsai T, Chang T, Chou C, Lin L . Lanostane-triterpenoids from the fungus Phellinus gilvus. Phytochemistry. 2009; 70(4):558-63. DOI: 10.1016/j.phytochem.2009.01.015. View

14.

Dai Y, Zhou L, Cui B, Chen Y, Decock C . Current advances in Phellinus sensu lato: medicinal species, functions, metabolites and mechanisms. Appl Microbiol Biotechnol. 2010; 87(5):1587-93. DOI: 10.1007/s00253-010-2711-3. View

15.

Grimblat N, Zanardi M, Sarotti A . Beyond DP4: an Improved Probability for the Stereochemical Assignment of Isomeric Compounds using Quantum Chemical Calculations of NMR Shifts. J Org Chem. 2015; 80(24):12526-34. DOI: 10.1021/acs.joc.5b02396. View

16.

Khadhri A, Aouadhi C, Aschi-Smiti S . Screening of Bioactive Compounds of Medicinal Mushrooms Collected on Tunisian Territory. Int J Med Mushrooms. 2017; 19(2):127-135. DOI: 10.1615/IntJMedMushrooms.v19.i2.40. View

17.

Bagno A, Rastrelli F, Saielli G . Toward the complete prediction of the 1H and 13C NMR spectra of complex organic molecules by DFT methods: application to natural substances. Chemistry. 2006; 12(21):5514-25. DOI: 10.1002/chem.200501583. View

18.

Gajdacs M, Spengler G, Sanmartin C, Marc M, Handzlik J, Dominguez-Alvarez E . Selenoesters and selenoanhydrides as novel multidrug resistance reversing agents: A confirmation study in a colon cancer MDR cell line. Bioorg Med Chem Lett. 2017; 27(4):797-802. DOI: 10.1016/j.bmcl.2017.01.033. View

19.

Wang X, Bao H, Bau T . Investigation of the possible mechanism of two kinds of sterols extracted from Leucocalocybe mongolica in inducing HepG2 cell apoptosis and exerting anti-tumor effects in H22 tumor-bearing mice. Steroids. 2020; 163:108692. DOI: 10.1016/j.steroids.2020.108692. View

20.

Lee I, Seok S, Kim W, Yun B . Hispidin derivatives from the mushroom Inonotus xeranticus and their antioxidant activity. J Nat Prod. 2006; 69(2):299-301. DOI: 10.1021/np050453n. View