title: Antituberculosis agents and an inhibitor of the para-aminobenzoic acid biosynthetic pathway from Hydnocarpus anthelminthica seeds.
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.
authors: State Key Laboratory of Phytochemistry and Plant Resources in West China, Kunming Institute of Botany, Chinese Academy of Sciences, Kunming 650204, P. R. China.
authors: Jun-Feng
authors: JF
authors: Wang
authors: Huan-Qin
authors: HQ
authors: Dai
authors: Yu-Ling
authors: YL
authors: Wei
authors: Hua-Jie
authors: HJ
authors: Zhu
authors: Yong-Ming
authors: YM
authors: Yan
authors: Yue-Hu
authors: YH
authors: Wang
authors: Chun-Lin
authors: CL
authors: Long
authors: Hui-Min
authors: HM
authors: Zhong
authors: Li-Xin
authors: LX
authors: Zhang
authors: Yong-Xian
authors: YX
authors: Cheng
mesh_terms: D010129:4-Aminobenzoic Acid / Q000037:antagonists & inhibitors* / Q000737:chemistry; D000995:Antitubercular Agents / Q000737:chemistry* / Q000494:pharmacology*; D053898:Biosynthetic Pathways / Q000187:drug effects; D002176:Candida albicans / Q000187:drug effects; D002478:Cells, Cultured; D009682:Magnetic Resonance Spectroscopy; D008826:Microbial Sensitivity Tests; D015394:Molecular Structure; D009169:Mycobacterium tuberculosis / Q000187:drug effects*; D031308:Salicaceae / Q000737:chemistry*; D012639:Seeds / Q000737:chemistry*
chemical_list: D000995:Antitubercular Agents; D010129:4-Aminobenzoic Acid