Sesquiterpene coumarin ethers with selective cytotoxic activities from the roots of ferula huber-morathii Peşmen (Apiaceae) and unequivocal determination of the absolute stereochemistry of samarcandin

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dc.authorid0000-0001-9265-8042
dc.contributor.authorEruçar, Fatma Memnune
dc.contributor.authorKuran, Fadıl Kaan
dc.contributor.authorAltıparmak Ülbegi, Gülsüm
dc.contributor.authorÖzbey, Süheyla
dc.contributor.authorKaravuş, Şule Nur
dc.contributor.authorArcan, Gülşah Gamze
dc.contributor.authorYazıcı Tütüniş, Seçil
dc.contributor.authorTan, Nur
dc.contributor.authorAksoy Sağırlı, Pınar
dc.contributor.authorMiski, Mahmut
dc.date.accessioned2023-07-25T08:32:14Z
dc.date.available2023-07-25T08:32:14Z
dc.date.issued2023
dc.departmentİstanbul Medipol Üniversitesi, Eczacılık Fakültesi, Eczacılık Meslek Bilimleri Bölümü, Farmakognozi Ana Bilim Dalı
dc.description.abstractAncient physicians frequently used the resin of Ferula species to treat cancer. Today, some folkloric recipes used for cancer treatment also contain the resin of Ferula species. The dichloromethane extract of the roots of Ferula huber-morathii exhibited cytotoxic activities against COLO 205 (colon), K-562 (lymphoblast), and MCF-7 (breast) cancer cell lines (IC50 = 52 µg/mL, 72 µg/mL, and 20 µg/mL, respectively). Fifteen sesquiterpene coumarin ethers with cytotoxic activity were isolated from the dichloromethane extract of the roots of F. huber-morathii using bioactivity-directed isolation studies. Extensive spectroscopic analyses and chemical transformations have elucidated the structures of these sesquiterpene coumarin ethers as conferone (1), conferol (2), feselol (3), badrakemone (4), mogoltadone (5), farnesiferol A (6), farnesiferol A acetate (7), gummosin (8), ferukrin (9), ferukrin acetate (10), deacetylkellerin (11), kellerin (12), samarcandone (13), samarcandin (14), and samarcandin acetate (15). The absolute configuration of samarcandin (14) was unequivocally determined by the X-ray crystallographic analysis of the semi-synthetic (R)-MTPA ester of samarcandin (24). Conferol (2) and mogoltadone (5) were found to be the most potent cytotoxic compounds against all three cancer cell lines; furthermore, these compounds exhibit low cytotoxic activity against the non-cancerous human umbilical vein epithelial cells (HUVEC) cell line. Investigation of the biological activity mechanisms of mogoltadone (5) revealed that while suppressing the levels of Bcl-XL and procaspase-3 in the COLO 205 cancer cell line, it did not have a significant effect on the Bcl-XL, caspase-3, and ?-catenin protein levels of the HUVEC cell line, which may explain the cytotoxic selectivity of mogoltadone (5) on cancer cell lines.
dc.identifier.citationEruçar, F. M., Kuran, F. K., Altıparmak Ülbegi, G., Özbey, S., Karavuş, Ş. N., Arcan, G. G. ... Miski, M. (2023). Sesquiterpene coumarin ethers with selective cytotoxic activities from the roots of ferula huber-morathii Peşmen (Apiaceae) and unequivocal determination of the absolute stereochemistry of samarcandin. Pharmaceuticals, 16(6). https://dx.doi.org/10.3390/ph16060792
dc.identifier.doi10.3390/ph16060792
dc.identifier.issn1424-8247
dc.identifier.issue6
dc.identifier.pmid37375740
dc.identifier.scopus2-s2.0-85163897625
dc.identifier.scopusqualityQ1
dc.identifier.urihttps://dx.doi.org/10.3390/ph16060792
dc.identifier.urihttps://hdl.handle.net/20.500.12511/11246
dc.identifier.volume16
dc.identifier.wos001021090100001en_US
dc.identifier.wosqualityQ2
dc.indekslendigikaynakWeb of Science
dc.indekslendigikaynakScopus
dc.indekslendigikaynakPubMed
dc.institutionauthorKaravuş, Şule Nur
dc.language.isoen
dc.publisherMDPI
dc.relation.ispartofPharmaceuticalsen_US
dc.relation.publicationcategoryMakale - Uluslararası Hakemli Dergi - Kurum Öğretim Elemanı
dc.relation.tubitakinfo:eu-repo/grantAgreement/TUBITAK/SOBAG/117S419
dc.rightsAttribution 4.0 International*
dc.rightsinfo:eu-repo/semantics/openAccess
dc.rights.urihttps://creativecommons.org/licenses/by/4.0/*
dc.subjectFerula Huber-Morathii
dc.subjectSesquiterpene Coumarin Ethers
dc.subjectCytotoxicity
dc.subjectCOLO 205
dc.subjectMCF-7
dc.subjectK-562
dc.subjectBcl-XL
dc.subjectCaspase 3, 8, 9
dc.subject?-Catenin
dc.subjectMolecular Docking
dc.titleSesquiterpene coumarin ethers with selective cytotoxic activities from the roots of ferula huber-morathii Peşmen (Apiaceae) and unequivocal determination of the absolute stereochemistry of samarcandin
dc.typeArticle

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