Five furofuranone lignan glucosides from Terminalia citrina inhibit in vitro E₂-enhanced breast cancer cell proliferation

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• 作者：Md. Abdul Muhit^a ; ^b ; Kaoru Umehara^a ; ^{umehara@u-shizuoka-ken.ac.jp" class="auth_mail" title="E-mail the corresponding author} ; Hiroshi Noguchi^a
• 关键词：Terminalia citrina ; Combretaceae ; Lignan ; Furofuranone ; Dioxabicyclooctyl ; Antiestrogenic activity ; Haritaki
• 刊名：Fitoterapia
• 出版年：2016
• 出版时间：September 2016
• 年：2016
• 卷：113
• 期：Complete
• 页码：74-79
• 全文大小：339 K

文摘

Five new polyalkoxylated furofuranone lignan glucosides, terminalosides L–P (1–5), were isolated from EtOAc extracts of the leaves of Terminalia citrina, a Bangladeshi medicinal plant. The structures of the isolates were deduced primarily by NMR spectroscopy, and four of the isolates were found to contain rare tetraoxygenated aryl groups in their structures. The absolute configurations and conformations of the furofuranone ring were confirmed by ECD spectroscopy. All of the isolates were evaluated for their estrogenic and/or antiestrogenic properties using two estrogen responsive breast cancer cell lines, T47D and MCF-7. At a concentration of 10 nM, terminaloside L (1) suppressed E₂-enhanced T47D cell proliferation by 90%, while terminaloside M (2) showed 90% antiestrogenic activity against MCF-7 cells. Compared to 2, the antiestrogenic activity of terminaloside O (4) and P (5) was weak, possibly due to the different attachment positions of the sugar moiety that they share in common. This is the first report of furofuranone lignans from any Terminalia species, and also of their antiestrogenic activity.