Antioxidant and free radical scavenging activities ofMisodendrum punctulatum, myzodendrone and structurally related phenols

Abstract

The peroxyl radical scavenging activity of a dry methanol extract of Misodendrum punctulatum was determined by means of luminol-enhanced chemiluminescence assay, allowing to calculate the total reactive antioxidant potential (TRAP) index equal to 239 +/- 26 microm, expressed in Trolox equivalents. The flavan-3-ol catechin (1) and the phenylbutanone derivative myzodendrone (2) were identified through assay-guided fractionation as active metabolites present in the extract, and their structures were elucidated by chemical and spectroscopic analysis. Three other structurally related synthetic phenols, dehydrozingerone (3), zingerone (4) and myzodendrone aglycone (5), were also analysed using this method. Compounds 1 and 2 were highly effective as free radical scavengers (TRAP = 1257 microm and 1018 microm, respectively) when compared with Trolox (TRAP = 144 microm), used as a standard. Compounds 3 and 5 were also active showing TRAP values of 229 microm and 219 microm, respectively, similarly to that observed for the dry extract. On the other hand, 4 was inactive. Catechin (1) also reduced the production of thiobarbituric acid reactive substances (TBARS) in rat liver homogenates, with IC50 = 26 microg/mL, superior to that obtained for Trolox, IC50 = 73 microg/mL. Compounds 2 and 5 showed IC50 values > 1000 microg/mL, while no activity could be observed for 3, 4, or the extract.

Structure-function activity of dehydrozingerone and its derivatives as antioxidant and antimicrobial compounds

“…The antioxidant activity has been attributed to various mechanisms, among which are the prevention of chain initiation, the binding of transition metal ion catalysts, decomposition of peroxides, the prevention of continued hydrogen abstraction, the reductive capacity and radical scavenging. DZ was found to be a free radical scavenger (total reactive antioxidant potential TRAP=229 μM) while zingerone, a hydrogenated product of DZ showed no activity which confirms the activity due to an extended ketone conjugation in DZ (Desmarchelier et al 2005). While, the hydroxyl radical scavenging activity of DZ (ES 15 value=48.36 mM) was reported to be lower than curcumin (25.01 mM) (Nugroho et al 2006).…”

Dehydrozingerone exerts beneficial metabolic effects in high‐fat diet‐induced obese mice via AMPK activation in skeletal muscle

“…Dehydrozingerone (DHZ), isolated from ginger ( Zingiber officinale ), is an unsaturated derivative of the natural product zingerone. DHZ exerts anti‐oxidant , free radical scavenging , and anti‐tumour activities , and also inhibits wound healing and lipid peroxidation . Metabolic roles for DHZ have been proposed, but the molecular mechanisms underlying these effects remain unclear.…”

A new phenolic compound with antioxidant activity from the branches and leaves of Pyrus pashia

“…Compound 1 (7) (Machida & Kikuchi, 1993), p-hydroxyphenyl 6-O-cis-p-Coumaroyl-b-D-glucopyranoside (8) (Machida & Kikuchi, 1993), 4-hydroxybenzoic acid (9) (Rukachaisirikul et al 2010), 4-(methoxymethyl) phenyl-1-Ob-D-glucopyranoside (10) , 3,4-dihydroxyacetophenone (11) (Ruan et al 2011), 3,4-dihytroxy benzaldehyde (12) , p-hytroxy benzaldehyde (13) (Yang et al 2013 ), 3-O-(b-D-glucopyranosyl)-1-(3 0 5 0 -dimethoxy-4-hydroxyphenyl-1-propanone (21) , myzodendrone (22) (Desmarchelier et al 2005) were identified by comparisons with spectroscopic data of literatures.…”