Cytotoxic naphthoquinones from Arnebia densiflora (Nordm.) Ledeb and determining new apoptosis inducers

• Published in: Natural product research Vol. 34; no. 12; pp. 1669 - 1677
• Main Authors: Yuzbasioglu Baran, Merve, Guvenalp, Zuhal, Saracoglu, Iclal, Kazaz, Cavit, Salih, Bekir, Demirezer, L. Omur, Kuruuzum-Uz, Ayse
• Format: Journal Article
• Language: English
• Published: Abingdon Taylor & Francis 17.06.2020; Taylor & Francis Ltd
• Subjects: Alkannin; Apoptosis; Arnebia densiflora; Boraginaceae; caspase; Caspase-3; Cell lines; Cytotoxicity; DNA fragmentation; n-Hexane; NMR; Nuclear magnetic resonance; Toxicity
• ISSN: 1478-6419; 1478-6427
• DOI: 10.1080/14786419.2018.1525714

In this study, phytochemical composition of Arnebia densiflora (AD) was determined and cytotoxic effects of the n-hexane extract and compounds isolated from this species on various cell lines were investigated. By means of serial chromatographic studies, 6 naphthoquinone derivatives were yielded, which are isovalerylalkannin, α-methyl-n-butyl alkannin, acetylalkannin, β-acetoxy isovalerylalkannin, alkannin and a new compound: 4-hydroxy 4-methyl valeryl alkannin. Structures of the isolated compounds were elucidated using UV, IR, 1D-2D NMR, MS and CD methods. Cytotoxic effects of the extract and isolated alkannins were investigated on L929, HeLa, HEp-2 cells. AD and the isolated compounds demonstrated moderate to strong cytotoxic effects (IC 50 range: 4.92-172.35 µg/ml). The results of DNA fragmentation and caspase-3 activity studies on HeLa cells exhibited that AD and the naphthoquinones isolated from it caused cytotoxicity through induction of apoptosis.