Chemical constituents and their bioactivities from truffle Hysterangium inflatum

Journal of Food Measurement and Characterization - Tập 15 Số 5 - Trang 4181-4189 - 2021
Taş, Meltem1, Küçükaydın, Selçuk2, Tel-Çayan, Gülsen3, Duru, Mehmet Emin1, Öztürk, Mehmet1, Türk, Mustafa4
1Department of Chemistry, Faculty of Science, Muğla Sıtkı Koçman University, Muğla, Turkey
2Department of Medical Services and Techniques, Köyceğiz Vocational School of Health Services, Muğla Sıtkı Koçman University, Köyceğiz, Turkey
3Department of Chemistry and Chemical Processing Technologies, Muğla Vocational School, Muğla Sıtkı Koçman University, Muğla, Turkey
4Department of Bioengineering, Faculty of Engineering and Architecture, Kirikkale University, Kirikkale, Turkey

Tóm tắt

Hysterangium inflatum is a truffle that grows naturally in the roots of Eucalyptus sp. and is distributed along the Mediterranean and Aegean coasts. Chemical investigation of the H. inflatum enabled to isolate of a new cerebroside, hysteroside (1), and seven known compounds namely, psyllic acid (2), brassicasterol (3), ergosterol (4), ergosterol d (5), ergosterol peroxide (6), ergosta-7,9,22-triene-3-O-β-d-glucoside (7) and mannitol (8). IR, NMR, MS techniques were used for structural elucidation and supported with literature data. Antioxidant, cholinesterase, urease, and tyrosinase inhibitory and cytotoxic activities on MCF-7 breast, H-1299 lung cancer cells, and murine fibroblast (L929) non-cancerous cells of extracts and isolated compounds from H. inflatum were analyzed. All the isolated compounds, except compounds 2 and 8, displayed considerable cytotoxic activities against MCF-7 and H-1299 cancer cells. Compounds 1 (IC50: 18.11 µg/mL) and 5 (IC50: 24.93 µg/mL) were the most effective against MCF-7, while compounds 6 (IC50: 27.61 µg/mL), 1 (IC50: 36.20 µg/mL) and 5 (IC50: 38.62 µg/mL) showed most potent toxicity against H-1299 and the extracts and compounds have no toxic effect on L929. Among the extracts, the methanol extract displayed the best antioxidant activity in all assays. Compound 1 exhibited highest enzyme inhibition activities with value of 58.71%, 52.84%, 45.37%, and 35.63%, against urease, tyrosinase, butrylcholinesterase (BChE), and acetylcholinesterase (AChE) enzymes at 100 µg/mL concentration, among the isolated compounds. These results support that H. inflatum is a steroid-rich truffle and might be a potential source, especially for ergostane type steroids.

Tài liệu tham khảo

citation_journal_title=3 Biotech.; citation_author=NN Shah, S Hokkanen, O Pastinen, A Eljamil, S Shamekh; citation_volume=10; citation_publication_date=2020; citation_pages=415; citation_doi=10.1007/s13205-020-02414-y; citation_id=CR1 citation_journal_title=AMB Express; citation_author=X Yan, Y Wang, X Sang, L Fan; citation_volume=7; citation_publication_date=2017; citation_pages=136; citation_doi=10.1186/s13568-017-0431-0; citation_id=CR2 citation_journal_title=Int. J. Mol. Sci.; citation_author=M Jayachandran, J Xiao, B Xu; citation_volume=18; citation_issue=9; citation_publication_date=2017; citation_pages=1934; citation_doi=10.3390/ijms18091934; citation_id=CR3 citation_journal_title=Int. J. Mol. Sci.; citation_author=G Venturella, V Ferraro, F Cirlincione, ML Gargano; citation_volume=22; citation_issue=2; citation_publication_date=2021; citation_pages=634; citation_doi=10.3390/ijms22020634; citation_id=CR4 citation_journal_title=Trends Food Sci. Technol.; citation_author=S Patel, A Rauf, H Khan, S Khalid, MS Mubarak; citation_volume=70; citation_publication_date=2017; citation_pages=1; citation_doi=10.1016/j.tifs.2017.09.009; citation_id=CR5 citation_journal_title=J. Food Meas. Charact.; citation_author=E Deveci, G Tel-Çayan, ME Duru, M Öztürk; citation_volume=13; citation_issue=4; citation_publication_date=2019; citation_pages=2686; citation_doi=10.1007/s11694-019-00189-2; citation_id=CR6 citation_journal_title=Cogent Food Agric.; citation_author=A Dundar, V Okumus, S Ozdemir, KS Celik, M Boğa, E Ozcagli; citation_volume=2; citation_publication_date=2016; citation_pages=1178060; citation_id=CR7 citation_journal_title=Trends Food Sci. Technol.; citation_author=O Taofiq, A Martins, MF Barreiro, ICFR Ferreira; citation_volume=50; citation_publication_date=2016; citation_pages=193; citation_doi=10.1016/j.tifs.2016.02.005; citation_id=CR8 citation_journal_title=Front. Microbiol.; citation_author=R Linnakoski, D Reshamwala, P Veteli, M Cortina-Escribano, H Vanhanen, V Marjomäki; citation_volume=9; citation_publication_date=2018; citation_pages=2325; citation_doi=10.3389/fmicb.2018.02325; citation_id=CR9 citation_journal_title=Rec. Nat. Prod.; citation_author=ME Duru, G Tel-Çayan; citation_volume=9; citation_issue=4; citation_publication_date=2015; citation_pages=456; citation_id=CR10 citation_journal_title=Fungal Biol. Biotechnol.; citation_author=H Lee, K Nam, Z Zahra, MQU Farooqi; citation_volume=7; citation_publication_date=2020; citation_pages=9; citation_doi=10.1186/s40694-020-00097-x; citation_id=CR11 citation_journal_title=J. Agric. Food Chem.; citation_author=PC Schmidberger, P Schieberle; citation_volume=65; citation_issue=42; citation_publication_date=2017; citation_pages=9287; citation_doi=10.1021/acs.jafc.7b04073; citation_id=CR12 citation_journal_title=Molecules; citation_author=AM Mustafa, S Angeloni, FK Nzekoue, D Abouelenein, G Sagratini, G Caprioli, E Torregiani; citation_volume=25; citation_issue=24; citation_publication_date=2020; citation_pages=5948; citation_doi=10.3390/molecules25245948; citation_id=CR13 citation_journal_title=Eur. Food Res. Technol.; citation_author=N Shah, A Usvalampi, S Chaudhary, T Seppänen-Laakso, S Marathe, S Bankar, R Singhal, S Shamekh; citation_volume=246; citation_publication_date=2020; citation_pages=723; citation_doi=10.1007/s00217-020-03438-7; citation_id=CR14 citation_journal_title=Sci. Rep.; citation_author=F Vita, C Taiti, A Pompeiano, N Bazihizina, V Lucarotti, S Mancuso, A Alpi; citation_volume=5; citation_publication_date=2015; citation_pages=12629; citation_doi=10.1038/srep12629; citation_id=CR15 citation_journal_title=Appl. Microbiol. Biotechnol.; citation_author=YJ Tang, RS Liu, HM Li; citation_volume=99; citation_publication_date=2015; citation_pages=2041; citation_doi=10.1007/s00253-015-6379-6; citation_id=CR16 citation_journal_title=Trends Food Sci. Technol.; citation_author=SAM Khalifa, MA Farag, N Yosri, JSM Sabir, A Saeed, SM Al-Mousawi, W Taha, SG Musharraf, S Patel, HR El-Seedi; citation_volume=91; citation_publication_date=2019; citation_pages=193; citation_doi=10.1016/j.tifs.2019.07.008; citation_id=CR17 citation_journal_title=Saudi. J. Biol. Sci.; citation_author=SS Dahham, SS Al-Rawi, AH Ibrahim, ASA Majid, AMSA Majid; citation_volume=25; citation_issue=8; citation_publication_date=2018; citation_pages=1524; citation_doi=10.1016/j.sjbs.2016.01.031; citation_id=CR18 citation_journal_title=Arab. J. Chem.; citation_author=A Hamza, N Zouari, S Zouari, H Jdir, S Zaidi, M Gtari, M Neffati; citation_volume=9; citation_issue=3; citation_publication_date=2016; citation_pages=383; citation_doi=10.1016/j.arabjc.2013.06.015; citation_id=CR19 citation_journal_title=Food Res. Int.; citation_author=E Tejedor-Calvo, K Amara, FS Reis, L Barros, A Martins, RC Calhelha, ME Venturini, D Blanco, D Redondo, P Marco, ICFR Ferreira; citation_volume=140; citation_publication_date=2021; citation_pages=110071; citation_doi=10.1016/j.foodres.2020.110071; citation_id=CR20 citation_journal_title=J. Appl. Environ. Biol. Sci.; citation_author=WY Attia, RE El-Naggar, A Bawadekji, MAl Ali; citation_volume=8; citation_publication_date=2018; citation_pages=152; citation_id=CR21 citation_journal_title=Biochem. Syst. Ecol.; citation_author=KJD Jumeta, DUK Kagho, JET Ateba, YSF Fotsing, JJK Bankeu, N Sewald, BL Ndjakou, L Mehreen, MS Ali, AS Ngouela; citation_volume=94; citation_publication_date=2021; citation_pages=104201; citation_doi=10.1016/j.bse.2020.104201; citation_id=CR22 citation_journal_title=Int. J. Med. Mushrooms; citation_author=F Çayan, G Tel-Çayan, E Deveci, M Öztürk, ME Duru; citation_volume=21; citation_issue=11; citation_publication_date=2019; citation_pages=1075; citation_doi=10.1615/IntJMedMushrooms.2019032893; citation_id=CR23 citation_journal_title=Biochem. Pharmacol.; citation_author=GL Ellman, KD Courtney, V Andres, RM Featherston; citation_volume=7; citation_publication_date=1961; citation_pages=88; citation_doi=10.1016/0006-2952(61)90145-9; citation_id=CR24 citation_journal_title=J. Food Biochem.; citation_author=E Deveci, G Tel-Çayan, ME Duru, M Öztürk; citation_volume=43; citation_publication_date=2019; citation_pages=e13078; citation_id=CR25 citation_journal_title=Int. J. Food Prop.; citation_author=E Deveci, G Tel-Çayan, ME Duru; citation_volume=21; citation_issue=1; citation_publication_date=2018; citation_pages=771; citation_doi=10.1080/10942912.2018.1431660; citation_id=CR26 citation_journal_title=Br. J. Pharm. Res.; citation_author=D Hamdan, M Wink, A El-Shazly; citation_volume=4; citation_issue=16; citation_publication_date=2014; citation_pages=1963; citation_doi=10.9734/BJPR/2014/12311; citation_id=CR27 citation_journal_title=Steroids; citation_author=G Jinminga, H Lina, L Jikaia; citation_volume=66; citation_publication_date=2001; citation_pages=771; citation_doi=10.1016/S0039-128X(01)00105-2; citation_id=CR28 citation_journal_title=Arch. Pharm. Res.; citation_author=HW Seo, TM Hung, MK Na, HJ Jung, JC Kim, JS Choi, JH Kim, HK Lee, IS Lee, KH Bae, M Hattori, BS Min; citation_volume=32; citation_issue=11; citation_publication_date=2009; citation_pages=1573; citation_doi=10.1007/s12272-009-2109-x; citation_id=CR29 citation_journal_title=J. Chem. Soc. Perkin Trans.; citation_author=RJ Abraham, JR Monasterios; citation_volume=2; citation_publication_date=1974; citation_pages=662; citation_doi=10.1039/p29740000662; citation_id=CR30 citation_journal_title=Steroids; citation_author=BB Zhang, XL Han, Q Jiang, ZX Liao, HS Wang; citation_volume=78; citation_publication_date=2013; citation_pages=38; citation_doi=10.1016/j.steroids.2012.10.011; citation_id=CR31 citation_journal_title=Cent. Asian J. Med. Sci.; citation_author=E Chuluunbaatar, P Sodnomtseren, C Chimedtseren, G Batsuren, B Dulamjav; citation_volume=3; citation_issue=2; citation_publication_date=2017; citation_pages=167; citation_id=CR32 citation_journal_title=Arch. Pharm. Res.; citation_author=HS Kang, JH Choi, WK Cho, JC Park, JS Choi; citation_volume=27; citation_issue=7; citation_publication_date=2004; citation_pages=742; citation_doi=10.1007/BF02980143; citation_id=CR33 citation_journal_title=Neuropharmacology; citation_author=R Anand, KD Gill, AA Mahdi; citation_volume=76; citation_publication_date=2014; citation_pages=27; citation_doi=10.1016/j.neuropharm.2013.07.004; citation_id=CR34 citation_journal_title=Curr. Med. Chem.; citation_author=Z Amtul, RA Atta-ur-Rahman, MI Siddiqui, null Choudhary; citation_volume=9; citation_publication_date=2012; citation_pages=1323; citation_doi=10.2174/0929867023369853; citation_id=CR35 citation_journal_title=Phytother. Res.; citation_author=S Parvez, M Kang, H Chung, H Bae; citation_volume=21; citation_publication_date=2007; citation_pages=805; citation_doi=10.1002/ptr.2184; citation_id=CR36