Antituberculosis Agents and an Inhibitor of the para-Aminobenzoic Acid Biosynthetic Pathway from Hydnocarpus anthelminthica Seeds
| Autor: | Yong-Ming Yan, Junfeng Wang, Lixin Zhang, Yu-Ling Wei, Yong-Xian Cheng, Chunlin Long, Hui-Min Zhong, Huanqin Dai, Hua-Jie Zhu, Yue-Hu Wang |
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| Rok vydání: | 2010 |
| Předmět: |
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 |
| Zdroj: | Chemistry & Biodiversity. 7:2046-2053 |
| ISSN: | 1612-1872 |
| DOI: | 10.1002/cbdv.201000072 |
| Popis: | 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. |
| Databáze: | OpenAIRE |
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