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Antituberculosis Agents and an Inhibitor of the para-Aminobenzoic Acid Biosynthetic Pathway from Hydnocarpus anthelminthica Seeds
- Source :
- Chemistry & Biodiversity. 7:2046-2053
- Publication Year :
- 2010
- Publisher :
- Wiley, 2010.
-
Abstract
- Investigation on the extracts of Hydnocarpus anthelminthica seeds led to the isolation of three new compounds, anthelminthicins A-C (1-3, resp.), and two known ones, namely chaulmoogric acid (4) and ethyl chaulmoograte (5). Their structures were determined mainly by using spectroscopic techniques. The absolute configuration at the cyclopentenyl moiety of compound 2 was rationalized by quantum calculations. Base hydrolysis, followed by optical-rotation comparison, allowed assignment of the configuration of chaulmoogric-acid moiety of compounds 3 and 5. Biological assays revealed that compounds 1-5 significantly inhibit Mycobacterium tuberculosis (MTB) growth with MIC values of 5.54, 16.70, 4.38, 9.82, and 16.80 microM, respectively. Compound 3 was found to inhibit the pathway between chorismate and para-aminobenzoic acid (pAba) with a MIC value of 11.3 microM, representing a new example of pAba inhibitor isolated from a natural source. All compounds were not toxic to Candida albicans SC5314 at a concentration up to 100 microM.
- Subjects :
- Magnetic Resonance Spectroscopy
Salicaceae
Stereochemistry
Chemical structure
Antitubercular Agents
Bioengineering
Microbial Sensitivity Tests
Biochemistry
Hydrolysis
chemistry.chemical_compound
Biosynthesis
Candida albicans
Moiety
Molecular Biology
Cells, Cultured
Molecular Structure
biology
Absolute configuration
Mycobacterium tuberculosis
General Chemistry
General Medicine
biology.organism_classification
Biosynthetic Pathways
Hydnocarpus
Metabolic pathway
chemistry
Seeds
Molecular Medicine
4-Aminobenzoic Acid
Subjects
Details
- ISSN :
- 16121872
- Volume :
- 7
- Database :
- OpenAIRE
- Journal :
- Chemistry & Biodiversity
- Accession number :
- edsair.doi.dedup.....72abd6d0ca411dc87d3044e54db8bc8f
- Full Text :
- https://doi.org/10.1002/cbdv.201000072