Methyl Chavicol and Its Synthetic Analogue as Possible Antioxidant and Antilipase Agents Based on the In Vitro and In Silico Assays

Abstract

This study investigated the in vitro and in silico biological properties of the methyl chavicol (MC) and its analogue 2-[(4-methoxyphenyl)methyl]oxirane (MPMO), emphasizing the antioxidant and antilipase effects. MPMO was synthesized from MC that reacted with meta-chloroperbenzoic acid and, after separation and purification, was identified by 1H and 13C NMR and GC-MS. The antioxidant activity was investigated by DPPH, cooxidation β-carotene/linoleic acid, and thiobarbituric acid assays. With the use of colorimetric determination, the antilipase effect on the pancreatic lipase was tested, while the molecular interaction profiles were evaluated by docking molecular study. MC (IC50 = 312.50 ± 2.28 μg/mL) and MPMO (IC50 = 8.29 ± 0.80 μg/mL) inhibited the DPPH free radical. The inhibition of lipid peroxidation (%) was 73.08 ± 4.79 and 36.16 ± 4.11 to MC and MPMO, respectively. The malonaldehyde content was significantly reduced in the presence of MC and MPMO. MC and MPMO inhibited the pancreatic lipase in 58.12 and 26.93%, respectively. MC and MPMO (−6.1 kcal·mol−1) produced a binding affinity value lower than did diundecylphosphatidylcholine (−5.6 kcal·mol−1). These findings show that MC and MPMO present antioxidant and antilipase activities, which may be promising molecular targets for the treatment of diseases associated with oxidative damage and lipid metabolism.

Artemisia dracunculus L. essential oil phytochemical components trigger the activity of cellular antioxidant enzymes

“…Having above mentioned, as well as some data concerning Artemisia plant application in herbal medicine (Nurzyńska‐Wierdak & Grażyna, 2014; Santos et al., 2018), our group decided to check the influence of A. dracunculus EO on microglia cell lines in order to reveal some mechanisms of its antioxidant and protective action.…”

“…In spite of the troubles concerning the toxic influence of Artemisia EO two main constituents, estragole and methyleugenol, there is no acute toxicity or mutagenic activity has been reported at doses relevant for human consumption (Pushpangadan & George, 2012). They possess antioxidant and anti‐inflammatory activities (Santos et al., 2018). It was purposeful for us to study the possible antioxidant effect of A. dracunculus EO on some cell models.…”

Bioactive Natural Compounds and Antioxidant Activity of Essential Oils from Spice Plants: New Findings and Potential Applications

“…In addition, EOs and their constituents have been investigated as an alternative additive in the food industry [ 44 , 59 ] in contrast to synthetic antioxidants, such as butylated hydroxytoluene, butylated hydroxyanisole, and propyl gallate, that have exhibited undesired effects to human health [ 60 , 61 ]. Natural compounds from plant EOs which have shown biological activities with potential pharmaceutical applications include ( E )-cinnamaldehyde (antifungal activity, Figure 1 panel A) [ 62 ]; menthol and L-menthol (analgesic activity, panels B and C) [ 63 ]; cuminaldehyde (anticancer activity, panel D) [ 64 ]; eucalyptol and eugenol (anti-inflammatory activity, panels E and F) [ 65 , 66 , 67 ]; and thymol, carvacrol, and methyl chavicol (antioxidant activities, panels G, H, and I) [ 68 , 69 ]. It is important to note that some well-known compounds found in EOs have been recently described with new biological activities, e.g., monoterpenes such as thymol, carvacrol, and p -cymene have been reported to reduce lung emphysema and inflammation [ 70 ] and eugenol has shown activity against several parasites with clinical relevance [ 71 , 72 ].…”

“…Methyl chavicol, the major compound identified in this oil, has been described by its antimicrobial and antioxidant activities [ 28 ]. Recently, a study identified that this compound and its analogs inhibit the human pancreatic lipase, thus showing a potential application in the treatment of lipid disorders [ 68 ].…”

Evaluating the In Vitro Potential of Natural Extracts to Protect Lipids from Oxidative Damage

“…Thus, spectrophotometric variation of the solution's color (a decrease in absorbance at approximately 470 nm) is representative of the generation of lipid peroxides. The procedure, advantages, and disadvantages of this system have been extensively discussed in the literature [130][131][132][133][134][135][136][137][138], and some examples of the latest LPIP research employing this method are suggested [139][140][141][142][143][144][145][146][147][148][149].…”