NDLI: Screening of flavonoids for antitubercular activity and their structure

Content Provider	Springer Nature Link
Author	Yadav, Akhilesh K. Thakur, Jayprakash Prakash, Om Khan, Feroz Saikia, Dharmendra Gupta, Madan M.
Copyright Year	2012
Abstract	The antitubercular activity of selected flavonoids and their structure–activity relationships were studied against Mycobacterium tuberculosis H 37 Rv strain radiometrically by BACTEC 460 assay. Present study led to the identification of five flavonoids, viz., luteolin, baicalein, quercetin, myricetin and hispidulin with MIC 25–100 μg ml−1, as new antitubercular templates. Rest flavonoids were found inactive against M. tuberculosis at a concentration of 100 μg ml−1. A possible structure–activity relationship (SAR) was also drawn to determine the specific structural requirements of flavonoids toward antitubercular activity. The hydroxyl substitution at position 5 and 7 provides no activity, whereas the hydroxyl substitutions at 5, 6, 7 (trihydroxy) or 3′, 4′ (dihydroxy) are of particular importance for antitubercular activity of a flavonoid. The O-methylation or glycosylation at any of di- or tri-hydroxyl substitutions inactivates the antitubercular potential of the flavonoids. We have also predicted the activity of studied flavonoids through QSAR model. A multiple linear regression QSAR mathematical model was developed for activity prediction that successfully and accurately (noting the corresponding experimental activities) predicted the antituberculosis activities of studied flavonoid compounds that had the basic pharmacophore, namely luteolin, baicalein, quercetin, myricetin, and hispidulin, with experimental and predicted n log MIC (μg ml−1) of 3.2189 & 2.583, 3.912 & 2.433, 3.912 & 2.433, 3.912 & 3.529, and 4.6052 & 2.703, respectively. The structure–activity relationship denoted by the QSAR model yielded a very high activity-descriptor relationship accuracy of 87 % referred by regression coefficient (r 2 = 0.870533) and a high activity prediction accuracy of 81 % (rCV2 = 0.81423). These compounds may represent novel leads toward the development of pharmacologically acceptable antitubercular agent/agents.
Starting Page	2706
Ending Page	2716
Page Count	11
File Format	PDF
ISSN	10542523
Journal	Medicinal Chemistry Research
Volume Number	22
Issue Number	6
e-ISSN	15548120
Language	English
Publisher	Springer-Verlag
Publisher Date	2012-10-11
Publisher Place	New York
Access Restriction	One Nation One Subscription (ONOS)
Subject Keyword	Flavonoids Isolation Mycobacterium tuberculosis Structure–activity relationships Pharmacology/Toxicology Biochemistry Cell Biology
Content Type	Text
Resource Type	Article
Subject	Organic Chemistry Pharmacology, Toxicology and Pharmaceutics

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