title: New pimarane diterpenes and other antimycobacterial metabolites from Anisochilus verticillatus.
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.
authors.affiliation: a Division of Organic Chemistry, CSIR-National Chemical Laboratory , Pune 411008 , India.
authors.forename: Roshan R
authors.initials: RR
authors.lastname: Kulkarni
authors.affiliation: b Combi-Chem Bio-Resource Centre, CSIR-National Chemical Laboratory , Pune 411008 , India.
authors.forename: Ketaki
authors.initials: K
authors.lastname: Shurpali
authors.affiliation: b Combi-Chem Bio-Resource Centre, CSIR-National Chemical Laboratory , Pune 411008 , India.
authors.forename: Vijay M
authors.initials: VM
authors.lastname: Khedkar
authors.affiliation: c Centre for Materials Characterization, CSIR-National Chemical Laboratory , Pune 411008 , India.
authors.forename: Vedavati G
authors.initials: VG
authors.lastname: Puranik
authors.affiliation: b Combi-Chem Bio-Resource Centre, CSIR-National Chemical Laboratory , Pune 411008 , India.
authors.forename: Dhiman
authors.initials: D
authors.lastname: Sarkar
authors.affiliation: a Division of Organic Chemistry, CSIR-National Chemical Laboratory , Pune 411008 , India.
authors.forename: Swati P
authors.initials: SP
authors.lastname: Joshi
mesh_terms: D045784:Abietanes / Q000302:isolation & purification / Q000494:pharmacology*; D000995:Antitubercular Agents / Q000302:isolation & purification / Q000494:pharmacology*; D018360:Crystallography, X-Ray; D005054:Eugenol / Q000031:analogs & derivatives / Q000302:isolation & purification / Q000494:pharmacology; D019686:Lamiaceae / Q000737:chemistry*; D009682:Magnetic Resonance Spectroscopy; D062105:Molecular Docking Simulation; D015394:Molecular Structure; D009169:Mycobacterium tuberculosis / Q000187:drug effects*; D009828:Oleanolic Acid / Q000031:analogs & derivatives / Q000302:isolation & purification / Q000494:pharmacology; D014315:Triterpenes / Q000302:isolation & purification / Q000494:pharmacology; D000097245:Ursolic Acid
chemical_list: D045784:Abietanes; D000995:Antitubercular Agents; D005054:Eugenol; D009828:Oleanolic Acid; D014315:Triterpenes; D000097245:Ursolic Acid; C000611359:8,9-secopimarane; C051268:2-hydroxychavicol; C036380:beta-amyrin
keywords: Anisochilus verticillatus; Lamiaceae; alanine racemase; antimycobacterial activity; diterpenes