New pimarane diterpenes and other antimycobacterial metabolites from Anisochilus verticillatus |
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Authors: | Roshan R Kulkarni Ketaki Shurpali Vijay M Khedkar Vedavati G Puranik Dhiman Sarkar |
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Institution: | 1. Division of Organic Chemistry, CSIR-National Chemical Laboratory, Pune 411008, India;2. Combi-Chem Bio-Resource Centre, CSIR-National Chemical Laboratory, Pune 411008, India;3. Centre for Materials Characterization, CSIR-National Chemical Laboratory, Pune 411008, India |
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Abstract: | Phytochemical investigation of the acetone extract of the aerial parts of Anisochilus verticillatus afforded a new 8,9-secopimarane diterpene (1), two new isopimarane diterpenes (2, 3) and the known ursolic acid (4), α-amyrin (5), β-amyrin (6), stigmast-5-en-3-one (7) and hydroxychavicol (8). Structures of the new compounds were elucidated with the help of 1D and 2D nuclear magnetic resonance spectroscopic data, and single crystal X-ray crystallography of compound 3. Compounds 2 and 8 inhibited Mycobacterium tuberculosis H37Ra with an IC50 of 11.3 (IC90 of 20.0 μg/mL) and 12.5 μg/mL, respectively. Correspondingly, molecular docking studies with Extra Precision Glide revealed a correlation between score and biological activity for these compounds to describe the molecular basis for the most significant SAR results. |
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Keywords: | Anisochilus verticillatus diterpenes antimycobacterial activity alanine racemase Lamiaceae |
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