title: Indiosides G-K: steroidal glycosides with cytotoxic and anti-inflammatory activities from Solanum violaceum.
abstract: Five new steroidal glycosides (1-5) and nine known compounds were isolated from Solanum violaceum. Indiosides G (1) and H (2) are spirostene saponins with an iso-type F ring, indioside I (3) is a spirostane saponin, and indiosides J (4) and K (5) are unusual furostanol saponins with a deformed F ring. These structures represent rare naturally occurring steroidal skeletons. The structures of the new compounds were elucidated using 1D and 2D spectroscopic techniques and acid hydrolysis. Compounds 2, 3, and 7-9 exhibited cytotoxic activity against six human cancer cell lines (HepG2, Hep3B, A549, Ca9-22, MDA-MB-231, and MCF-7) with IC(50) values of 1.83-8.04 μg/mL. Steroidal saponins 3, 8, and 9 showed inhibitory effects on superoxide anion generation with IC(50) values of 2.84 ± 0.18, 0.62 ± 0.03, and 1.62 ± 0.59 μg/mL, respectively. Saponins 8 and 9 also inhibited elastase release with IC(50) values of 111.05 ± 7.37 and 4.04 ± 0.51 μg/mL, respectively. Structure-activity relationship correlations of these compounds with respect to cytotoxic and anti-inflammatory effects are discussed.
authors.affiliation: Graduate Institute of Natural Products, Kaohsiung Medical University, Kaohsiung 80708, Taiwan, Republic of China.
authors.forename: Chiao-Ting
authors.initials: CT
authors.lastname: Yen
authors.forename: Chia-Lin
authors.initials: CL
authors.lastname: Lee
authors.forename: Fang-Rong
authors.initials: FR
authors.lastname: Chang
authors.forename: Tsong-Long
authors.initials: TL
authors.lastname: Hwang
authors.forename: Hsin-Fu
authors.initials: HF
authors.lastname: Yen
authors.forename: Chao-Jung
authors.initials: CJ
authors.lastname: Chen
authors.forename: Shu-Li
authors.initials: SL
authors.lastname: Chen
authors.forename: Yang-Chang
authors.initials: YC
authors.lastname: Wu
mesh_terms: D000893:Anti-Inflammatory Agents / Q000737:chemistry / Q000302:isolation & purification* / Q000494:pharmacology*; D000970:Antineoplastic Agents / Q000737:chemistry / Q000302:isolation & purification* / Q000494:pharmacology*; D004354:Drug Screening Assays, Antitumor; D006027:Glycosides / Q000737:chemistry / Q000302:isolation & purification* / Q000494:pharmacology*; D006801:Humans; D020128:Inhibitory Concentration 50; D015394:Molecular Structure; D009504:Neutrophils / Q000187:drug effects / Q000201:enzymology; D019906:Nuclear Magnetic Resonance, Biomolecular; D032322:Solanum / Q000737:chemistry*; D013256:Steroids / Q000737:chemistry / Q000302:isolation & purification* / Q000494:pharmacology*; D013329:Structure-Activity Relationship; D013624:Taiwan
chemical_list: D000893:Anti-Inflammatory Agents; D000970:Antineoplastic Agents; D006027:Glycosides; D013256:Steroids; C540431:indioside I