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Antiproliferative Constituents of the Roots of Ethiopian Podocarpus falcatus and Structure Revision of 2α-Hydroxynagilactone F and Nagilactone I.
- Source :
-
Journal of natural products [J Nat Prod] 2015 Apr 24; Vol. 78 (4), pp. 827-35. Date of Electronic Publication: 2015 Mar 25. - Publication Year :
- 2015
-
Abstract
- Bioassay-guided fractionation using the human colorectal adenocarcinoma (HT-29) cell line of the methanol extract of dried roots of Podocarpus falcatus led to the isolation of two new type C nagilactones, 16-hydroxynagilactone F (1) and 2β,16-dihydroxynagilactone F (2), and the new totarane-type bisditerpenoid 7β-hydroxymacrophyllic acid (4), along with the seven known compounds 2β-hydroxynagilactone F (3), macrophyllic acid (5), nagilactone D (6), 15-hydroxynagilactone D (7), nagilactone I (8), inumakiol D (9), and ponasterone A (10). The structures of the new compounds were determined by 1D and 2D NMR, HRESIMS, UV, and IR and by comparison with the reported spectroscopic data of their congeners. The orientation of the C-2 hydroxy group of 3 and 8 was revised to be β based on evidence from detailed analysis of 1D and 2D NMR data and single-crystal X-ray diffraction studies. Among the isolated compounds, the nagilactones, including the new dilactones 16-hydroxynagilactone F (1) and 2β,16-dihydroxynagilactone F (2), were the most active (IC50 0.3-5.1 μM range) against the HT-29 cell line, whereas the bisditerpenoids (4 and 5) and the other known compounds 9 and 10 were inactive. The presence of the bioactive nagilactones in P. falcatus supports its traditional use.
- Subjects :
- Abietanes
Antineoplastic Agents, Phytogenic chemistry
Diterpenes chemistry
Drug Screening Assays, Antitumor
Ethiopia
HT29 Cells
Humans
Molecular Structure
Nuclear Magnetic Resonance, Biomolecular
Plant Roots chemistry
Antineoplastic Agents, Phytogenic isolation & purification
Antineoplastic Agents, Phytogenic pharmacology
Diterpenes isolation & purification
Diterpenes pharmacology
Pinaceae chemistry
Subjects
Details
- Language :
- English
- ISSN :
- 1520-6025
- Volume :
- 78
- Issue :
- 4
- Database :
- MEDLINE
- Journal :
- Journal of natural products
- Publication Type :
- Academic Journal
- Accession number :
- 25807242
- Full Text :
- https://doi.org/10.1021/np501062f