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A new cyclooxygenase (COX) inhibitory pterocarpan from Indigofera aspalathoides: structure elucidation and determination of binding orientations in the active sites of the enzyme by molecular docking

2004; Elsevier BV; Volume: 45; Issue: 22 Linguagem: Inglês

10.1016/j.tetlet.2004.04.010

1873-3581

Chelliah Selvam, Sanjay M. Jachak, Rajaraman Gnana Oli, Ramasamy Thilagavathi, Asit K. Chakraborti, Kamlesh K. Bhutani,

Synthesis and biological activity

A new compound indigocarpan (1) and the known compound mucronulatol (2) were isolated from chloroform extracts of Indigofera aspalathoides. Their structures were established by spectroscopic methods, including single-crystal X-ray analysis (in the case of 1). The isolates were evaluated for cyclooxygenase-1 (COX-1) and cyclooxygenase-2 (COX-2) inhibitory activities and antioxidant properties. The new compound 1 showed significant COX-1 inhibition (IC50 30.5 μM) and its in vivo anti-inflammatory activity was found to be comparable to that of ibuprofen. Molecular docking studies revealed the binding orientations of 1 in the active sites of COX-1 and COX-2.