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Indiosides G-K: steroidal glycosides with cytotoxic and anti-inflammatory activities from Solanum violaceum.
- Source :
-
Journal of natural products [J Nat Prod] 2012 Apr 27; Vol. 75 (4), pp. 636-43. Date of Electronic Publication: 2012 Mar 13. - Publication Year :
- 2012
-
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.<br /> (© 2012 American Chemical Society and American Society of Pharmacognosy)
- Subjects :
- Anti-Inflammatory Agents chemistry
Antineoplastic Agents chemistry
Drug Screening Assays, Antitumor
Glycosides chemistry
Humans
Inhibitory Concentration 50
Molecular Structure
Neutrophils drug effects
Neutrophils enzymology
Nuclear Magnetic Resonance, Biomolecular
Steroids chemistry
Structure-Activity Relationship
Taiwan
Anti-Inflammatory Agents isolation & purification
Anti-Inflammatory Agents pharmacology
Antineoplastic Agents isolation & purification
Antineoplastic Agents pharmacology
Glycosides isolation & purification
Glycosides pharmacology
Solanum chemistry
Steroids isolation & purification
Steroids pharmacology
Subjects
Details
- Language :
- English
- ISSN :
- 1520-6025
- Volume :
- 75
- Issue :
- 4
- Database :
- MEDLINE
- Journal :
- Journal of natural products
- Publication Type :
- Academic Journal
- Accession number :
- 22413887
- Full Text :
- https://doi.org/10.1021/np200877u