Premium
Antituberculosis Agents and an Inhibitor of the para ‐Aminobenzoic Acid Biosynthetic Pathway from Hydnocarpus anthelminthica Seeds
Author(s) -
Wang JunFeng,
Dai HuanQin,
Wei YuLing,
Zhu HuaJie,
Yan YongMing,
Wang YueHu,
Long ChunLin,
Zhong HuiMin,
Zhang LiXin,
Cheng YongXian
Publication year - 2010
Publication title -
chemistry and biodiversity
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.427
H-Index - 70
eISSN - 1612-1880
pISSN - 1612-1872
DOI - 10.1002/cbdv.201000072
Subject(s) - moiety , chemistry , stereochemistry , absolute configuration , candida albicans , aminobenzoic acid , hydrolysis , mycobacterium tuberculosis , acid hydrolysis , biochemistry , microbiology and biotechnology , medicinal chemistry , tuberculosis , medicine , pathology , biology
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 μ M , respectively. Compound 3 was found to inhibit the pathway between chorismate and para ‐aminobenzoic acid ( p Aba) with a MIC value of 11.3 μ M , representing a new example of p Aba inhibitor isolated from a natural source. All compounds were not toxic to Candida albicans SC5314 at a concentration up to 100 μ M .