title: Five furofuranone lignan glucosides from Terminalia citrina inhibit in vitro E2-enhanced breast cancer cell proliferation.
abstract: 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 10nM, 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.
authors.affiliation: School of Pharmaceutical Sciences, University of Shizuoka, 52-1 Yada, Shizuoka 422-8526, Japan; Department of Clinical Pharmacy and Pharmacology, University of Dhaka, Dhaka 1000, Bangladesh.
authors.forename: Md Abdul
authors.initials: MA
authors.lastname: Muhit
authors.affiliation: School of Pharmaceutical Sciences, University of Shizuoka, 52-1 Yada, Shizuoka 422-8526, Japan. Electronic address: umehara@u-shizuoka-ken.ac.jp.
authors.forename: Kaoru
authors.initials: K
authors.lastname: Umehara
authors.affiliation: School of Pharmaceutical Sciences, University of Shizuoka, 52-1 Yada, Shizuoka 422-8526, Japan.
authors.forename: Hiroshi
authors.initials: H
authors.lastname: Noguchi
mesh_terms: D000972:Antineoplastic Agents, Phytogenic / Q000737:chemistry / Q000302:isolation & purification; D045744:Cell Line, Tumor; D049109:Cell Proliferation / Q000187:drug effects; D004958:Estradiol / Q000494:pharmacology; D004965:Estrogen Antagonists / Q000737:chemistry* / Q000302:isolation & purification; D005960:Glucosides / Q000737:chemistry* / Q000302:isolation & purification; D006801:Humans; D017705:Lignans / Q000737:chemistry* / Q000302:isolation & purification; D061986:MCF-7 Cells; D015394:Molecular Structure; D010946:Plants, Medicinal / Q000737:chemistry; D029766:Terminalia / Q000737:chemistry*
chemical_list: D000972:Antineoplastic Agents, Phytogenic; D004965:Estrogen Antagonists; D005960:Glucosides; D017705:Lignans; C000613792:terminaloside L; C000613793:terminaloside M; D004958:Estradiol
keywords: Antiestrogenic activity; Combretaceae; Dioxabicyclooctyl; Furofuranone; Haritaki; Lignan; Terminalia citrina