title: Saponins with highly hydroxylated oleanane-type aglycones from Silphium asteriscus L.
abstract: Silphium asteriscus L., commonly known as starry rosinweed, is a plant found in prairies, glades, woodlands and savannas of the southeastern United States. The phytochemical investigation of the methanolic extract of S. asteriscus leaves led to the isolation of eighteen saponins with highly hydroxylated oleanane-type aglycones never reported before. Their structures were elucidated by extensive spectroscopic methods including 1D- ((1)H and (13)C) and 2D-NMR (DQF-COSY, HSQC, HMBC, TOCSY and ROESY) experiments as well as ESIMS analysis. The antiproliferative activity of the isolated compounds was evaluated against three cancer cell lines including Hela (human epitheloid cervix carcinoma), Jurkat cells (leukaemic T-cell line) and DLD-1 (colorectal adenocarcinoma). Compounds 1, 5 and 17 displayed weak activity with IC50 values ranging from 50 to 75 μM.
authors.affiliation: Dipartimento di Farmacia, Università degli Studi di Salerno, Via Giovanni Paolo II n.132, I-84084 Fisciano (SA), Italy.
authors.forename: Milena
authors.initials: M
authors.lastname: Masullo
authors.affiliation: The Evergreen State College, 2700 Evergreen Parkway, Olympia, WA 98505, United States.
authors.forename: Lalita
authors.initials: L
authors.lastname: Calabria
authors.affiliation: Dipartimento di Farmacia, Università degli Studi di Salerno, Via Giovanni Paolo II n.132, I-84084 Fisciano (SA), Italy.
authors.forename: Dario
authors.initials: D
authors.lastname: Gallotta
authors.affiliation: Dipartimento di Farmacia, Università degli Studi di Salerno, Via Giovanni Paolo II n.132, I-84084 Fisciano (SA), Italy.
authors.forename: Cosimo
authors.initials: C
authors.lastname: Pizza
authors.affiliation: Dipartimento di Farmacia, Università degli Studi di Salerno, Via Giovanni Paolo II n.132, I-84084 Fisciano (SA), Italy. Electronic address: piacente@unisa.it.
authors.forename: Sonia
authors.initials: S
authors.lastname: Piacente
mesh_terms: D000972:Antineoplastic Agents, Phytogenic / Q000737:chemistry / Q000302:isolation & purification* / Q000494:pharmacology; D019659:Asteraceae / Q000737:chemistry*; D004354:Drug Screening Assays, Antitumor; D005260:Female; D006367:HeLa Cells; D006801:Humans; D019169:Jurkat Cells; D015394:Molecular Structure; D019906:Nuclear Magnetic Resonance, Biomolecular; D009828:Oleanolic Acid / Q000031:analogs & derivatives* / Q000737:chemistry / Q000302:isolation & purification / Q000494:pharmacology; D012503:Saponins / Q000737:chemistry* / Q000302:isolation & purification* / Q000494:pharmacology
chemical_list: D000972:Antineoplastic Agents, Phytogenic; D012503:Saponins; C413246:oleanane; D009828:Oleanolic Acid
keywords: Highly hydroxylated aglycones; Oleanane-type saponins; Silphium asteriscus