Five new cardenolides transformed from oleandrin and nerigoside by Alternaria eureka 1E1BL1 and Phaeosphaeriasp. 1E4CS-1 and their cytotoxic activities

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dc.contributor.authorKarakoyun Ç.
dc.contributor.authorKüçüksolak M.
dc.contributor.authorBilgi E.
dc.contributor.authorDoğan G.
dc.contributor.authorÇömlekçi Y.E.
dc.contributor.authorBedir E.
dc.date.accessioned2021-05-03T20:57:06Z
dc.date.available2021-05-03T20:57:06Z
dc.date.issued2021
dc.description.abstractBiotransformation of oleandrin (1) and nerigoside (2) by endophytic fungi; Alternaria eureka 1E1BL1 and Phaeospheria sp. 1E4CS-1, has led to the isolation of five new metabolites (3, 5, 6, 7 and 8) together with a known compound (4). The structures of the biotransformation products were elucidated by 1D-, 2D NMR and HR-MS. Phaeospheria sp. mainly provided monooxygenation reactions on the A and B rings, whereas A. eureka afforded both monooxygenated and desacetylated derivatives of the substrates. Cytotoxic activity of the compounds was tested against a non-cancerous (HEK-293) and four cancer (PANC-1, MIA PaCa-2, DU 145 and A549) cell lines by MTT cell viability assay. All compounds were less cytotoxic than oleandrin, which had IC50 values ranging between 2.7 and 41.9 nM. Two of the monohydroxylated metabolites, viz. 7(?)-hydroxy oleandrin (3) and 1(?)-hydroxy oleandrin (7), were also potent with IC50 values from 18.45 to 39.0 nM, while desacetylated + monohydroxylated, or dihydroxylated products had much lower cytotoxicity. Additionally, the lesser activity of 2 and its metabolite (6) possessing diginose as sugar residue inferred that oleandrose moiety is important for the toxicity of oleandrin as well as hydrophobicity of the steroid core. © 2020 Phytochemical Society of Europeen_US
dc.description.sponsorship152Z118 Türkiye Bilimsel ve Teknolojik Araştirma Kurumu, TÜBITAKen_US
dc.description.sponsorshipThis project was supported by The Scientific and Technological Research Council of Turkey (TUBITAK, Project No: 152Z118). We are thankful to Dr. Özge Özşen for her assistance in preliminary experiments.en_US
dc.identifier.doi10.1016/j.phytol.2020.12.003
dc.identifier.endpage157en_US
dc.identifier.issn1874-3900
dc.identifier.issn1874-3900en_US
dc.identifier.scopus2-s2.0-85098151251en_US
dc.identifier.scopusqualityQ2en_US
dc.identifier.startpage152en_US
dc.identifier.urihttps://doi.org/10.1016/j.phytol.2020.12.003
dc.identifier.urihttps://hdl.handle.net/11454/71488
dc.identifier.volume41en_US
dc.indekslendigikaynakScopusen_US
dc.language.isoenen_US
dc.publisherElsevier Ltden_US
dc.relation.ispartofPhytochemistry Lettersen_US
dc.relation.publicationcategoryMakale - Uluslararası Hakemli Dergi - Kurum Öğretim Elemanıen_US
dc.rightsinfo:eu-repo/semantics/closedAccessen_US
dc.subjectCytotoxicityen_US
dc.subjectEndophytic fungien_US
dc.subjectMicrobial biotransformationen_US
dc.subjectNerigosideen_US
dc.subjectNerium oleanderen_US
dc.subjectOleandrinen_US
dc.titleFive new cardenolides transformed from oleandrin and nerigoside by Alternaria eureka 1E1BL1 and Phaeosphaeriasp. 1E4CS-1 and their cytotoxic activitiesen_US
dc.typeArticleen_US

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