Structural elucidation and molecular docking of ferulic acid from Parthenium hysterophorus possessing COX-2 inhibition activity

Abstract

In this study, isolation of ferulic acid from Parthenium hysterophorus L. followed by the structural characterization using elemental analysis, FT-IR, NMR, ESI–MS and XRD has been carried out. The molecular geometry, harmonic vibrational frequencies and structural parameters were computed by density functional theory with the 6-311G** basis set. Comparisons between experimental and simulated data of spectroscopic analysis and geometrical parameters was accomplished for their statistical validation and the values of correlation coefficient for 1H and 13C-NMR chemical shifts, bond lengths and bond angles were found to be 0.934, 0.951, 0.943 and 0.961, respectively. The HOMO and LUMO analyses were used to find out the charge transfer within the ferulic acid. Thermal studies were carried out by thermogravimetry (TG), differential thermogravimetric analysis (DTA), and derivative thermogravimetry (DTG) to confirm the effect of temperature upon the ferulic acid. Furthermore, the binding study of the optimized geometry of ferulic acid has been envisioned with cyclooxygenase-2 for its activity inhibition by molecular docking.Electronic supplementary materialThe online version of this article (doi:10.1007/s13205-014-0253-6) contains supplementary material, which is available to authorized users.

Screening of metabolites from endophytic fungi of some Nigerian medicinal plants for antimicrobial activities

“…. Ferulic acid, a derivative of cinnamic acid, is a predominant natural phenolic compound first isolated from the plant Ferula foetida (45). It is present in plant seeds and leaves as a component of lignocelluloses, conferring rigidity to the cell wall by making the crosslink between polysaccharides and lignin (45,87).…”

“…Ferulic acid, a derivative of cinnamic acid, is a predominant natural phenolic compound first isolated from the plant Ferula foetida (45). It is present in plant seeds and leaves as a component of lignocelluloses, conferring rigidity to the cell wall by making the crosslink between polysaccharides and lignin (45,87). Ferulic acid has been detected in and/or isolated from culture extracts of endophytic fungi like Annulohypoxylon stygium (88) and Aspergillus austroafricanus (89).…”

Ferulic acid ameliorates TNBS-induced ulcerative colitis through modulation of cytokines, oxidative stress, iNOs, COX-2, and apoptosis in laboratory rats

“…The presence of electron-donating -OH groups attached to the para or 4-position of the aromatic ring in FA owing to a greater number of canonical resonance that eventually contribute to its antioxidant property (Karamac et al, 2005[40]). Furthermore, previous molecular docking study of FA with Cyclooxygenase-2 showed that it forms dimer via the formation of a strong hydrogen bond between -OH of -COOH group of one FA molecule with the oxygen atom of the C = O group of adjacent molecule to serves as potent inhibitors of COX-2 enzyme (Kumar and Pruthi, 2015[44]).…”

Parthenium weed: uses and abuses.

“…Although the 'causes and effects' are not quite proven, the bioactivity recorded by these studies may justify the uses of parthenium weed in traditional medicine. These studies have non-specifically attributed the properties to the occurrence of flavonoids, terpenoids, alkaloids and phenolic compounds in the weed's extracts (Kumar et al, 2014;Kumar and Pruthi, 2015). However, despite the evidence from largely in vitro and in vivo studies indicating the anticancer, antioxidant and antibacterial potential in parthenium weed extracts, developing these properties towards modern medicines is still a long way off.…”

“…Ethanolic extracts of dried leaves tested in vivo (rat kidney cells) and in in vitro models Potent cytotoxicity against MCF-7 and THP-1 human cancer cell lines at 100 mg/ ml; concentration-dependent inhibition of HL-60 cancer cell lines; moderately anti-HIV activity Kumar et al (2013aKumar et al ( , 2013b Antiinflammato y activity Extracts of parthenium weed Ferulic acid (FA) extracted from the weed inhibited the enzyme cyclooxygenase-2 (COX-2) by molecular docking; this may lead to developing anti-inflammato y drugs Kumar and Pruthi (2015) Antibacterial activity…”