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Bioassay-Guided Isolation and Structural Modification of the Anti-TB Resorcinols from Ardisia gigantifolia.
- Source :
-
Chemical biology & drug design [Chem Biol Drug Des] 2016 Aug; Vol. 88 (2), pp. 293-301. Date of Electronic Publication: 2016 Apr 26. - Publication Year :
- 2016
-
Abstract
- Tuberculosis (TB) is a highly contagious disease mainly caused by Mycobacterium tuberculosis H37 RV . Antitubercular (anti-TB) bioassay-guided isolation of the CHCl3 extract of the leaves and stems of the medicinal plant Ardisia gigantifolia led to the isolation of two anti-TB 5-alkylresorcinols, 5-(8Z-heptadecenyl) resorcinol (1) and 5-(8Z-pentadecenyl) resorcinol (2). We further synthesized 15 derivatives based on these two natural products. These compounds (natural and synthetic) were evaluated for their anti-TB activity against Mycobacterium tuberculosis H37 RV . Resorcinols 1 and 2 exhibited anti-TB activity with MIC values at 34.4 and 79.2 μm in MABA assay, respectively, and 91.7 and 168.3 μm in LORA assay, respectively. Among these derivatives, compound 8 was found to show improved anti-TB activity than its synthetic precursor (2) with MIC values at 42.0 μm in MABA assay and 100.2 μm in LORA assay. The active compounds should be regarded as new hits for further study as a novel class of anti-TB agents. The distinct structure-activity correlations of the parent compound were elucidated based on these derivatives.<br /> (© 2016 John Wiley & Sons A/S.)
- Subjects :
- Antitubercular Agents pharmacology
Magnetic Resonance Spectroscopy
Microbial Sensitivity Tests
Resorcinols pharmacology
Spectrometry, Mass, Electrospray Ionization
Antitubercular Agents chemistry
Antitubercular Agents isolation & purification
Ardisia chemistry
Biological Assay
Plant Extracts pharmacology
Resorcinols chemistry
Resorcinols isolation & purification
Subjects
Details
- Language :
- English
- ISSN :
- 1747-0285
- Volume :
- 88
- Issue :
- 2
- Database :
- MEDLINE
- Journal :
- Chemical biology & drug design
- Publication Type :
- Academic Journal
- Accession number :
- 26992112
- Full Text :
- https://doi.org/10.1111/cbdd.12756