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Title: Five new cardenolides transformed from oleandrin and nerigoside by Alternaria eureka 1E1BL1 and Phaeosphaeriasp. 1E4CS-1 and their cytotoxic activities
Authors: Karakoyun, Çiğdem
Küçüksolak, Melis
Bilgi, Eyüp
Doğan, Gamze
Çömlekçi, Yiğit Ege
Bedir, Erdal
Keywords: Cytotoxicity
Endophytic fungi
Microbial biotransformation
Nerium oleander
Issue Date: 2021
Publisher: Elsevier Ltd.
Abstract: Biotransformation 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 Europe
ISSN: 1876-7486
Appears in Collections:Bioengineering / Biyomühendislik
Scopus İndeksli Yayınlar Koleksiyonu / Scopus Indexed Publications Collection
WoS İndeksli Yayınlar Koleksiyonu / WoS Indexed Publications Collection

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