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Structure and bioactivity of steroidal saponins isolated from the roots of Chamaelirium luteum (false unicorn).
- Source :
-
Journal of natural products [J Nat Prod] 2012 Aug 24; Vol. 75 (8), pp. 1469-79. Date of Electronic Publication: 2012 Aug 10. - Publication Year :
- 2012
-
Abstract
- Phytochemical investigation of Chamaelirium luteum ("false unicorn") resulted in the isolation of 15 steroidal glycosides. Twelve of these (1, 2, 4-9, 11-13, and 15) are apparently unique to this species, and eight of these (6-9, 11-13, and 15) are previously unreported compounds; one (15) possesses a new steroidal aglycone. In addition, the absolute configuration of (23R,24S)-chiograsterol A (10) was defined, and its full spectroscopic characterization is reported for the first time. The structures and configurations of the saponins were determined using a combination of multistage mass spectrometry (MS(n)), 1D and 2D NMR experiments, and chemical degradation. The antiproliferative activity of nine compounds obtained in the present work, and eight related compounds generated in previous work, was compared in six human tumor cell lines, with aglycones 3 and 10 and related derivatives 16, 17, 19, and 20 all displaying significant antiproliferative activity.
- Subjects :
- Antineoplastic Agents, Phytogenic chemistry
Drug Screening Assays, Antitumor
Humans
Molecular Structure
Nuclear Magnetic Resonance, Biomolecular
Plant Roots chemistry
Saponins chemistry
Steroids chemistry
Antineoplastic Agents, Phytogenic isolation & purification
Antineoplastic Agents, Phytogenic pharmacology
Liliaceae chemistry
Plants, Medicinal chemistry
Saponins isolation & purification
Saponins pharmacology
Steroids isolation & purification
Steroids pharmacology
Subjects
Details
- Language :
- English
- ISSN :
- 1520-6025
- Volume :
- 75
- Issue :
- 8
- Database :
- MEDLINE
- Journal :
- Journal of natural products
- Publication Type :
- Academic Journal
- Accession number :
- 22880631
- Full Text :
- https://doi.org/10.1021/np300393y