New phenylpropanoid esters of sucrose from Polygonum hydropiper and their antioxidant activity

Abstract

By various chromatographic methods, two new phenylpropanoid esters of sucrose named hidropiperosides A (1) and B (2), and three known compounds as vanicosides A (3), B (4), and E (5) were isolated from the methanolic extract of the whole plant of Polygonum hydropiper L. (Polygonaceae). Their structures were elucidated by extensive spectroscopic methods including 1D-and 2D-NMR experiments, as well as ESI-MS analysis. All the isolated compounds were tested for their antioxidant activity in the 1,1-diphenyl-2-picrylhydrazyl (DPPH) radical scavenging assay system. Among them, compounds 2 and 3 showed significant antioxidant activity with their SC(50) values of 23.4 and 26.7 microg/mL, respectively.

In vitro and in vivo anti-inflammatory activities of Polygonum hydropiper methanol extract

“…Many anti-oxidative flavonoids, sesquiterpenoids, and coumarin compounds, including 7,4 -dimethylquercetin, 3 -methylquercetin, quercetin, isoquercitrin, polygodial, warburganal, hydropiperoside, rhamnazin, and persicarin are constituents of Polygonum hydropiper (Horhammer and Rao, 1954;Kiem et al, 2008;Yang et al, 2011;Sultana et al, 2011). Of these compounds, quercetin has already been reported as a strong anti-inflammatory drug with Syk and Src inhibitory activities (Lee et al, 2008).…”

“…Several components of this plant have been reported to display various biological activities. For example, anti-fungal (polygodial and warburganal), anti-inflammatory (polygonolide), and anti-oxidative (hydropiperoside, rhamnazin, and persicarin) compounds were reported previously (Ley, 1990;Park et al, 1996;Takasaki et al, 2001;Peng et al, 2003;Kiem et al, 2008).…”

Ethnobotanical, Phytochemical, Pharmacological, and Toxicological Aspects of Persicaria hydropiper (L.) Delarbre

“…Various extracts and fractions of P. hydropiper whole plant and herbs were found to contain flavonoids, such as (+)-catechin, (−)-epicatechin, hyperin, isoquercitrin (Figure 1), isorhamnetin (Figure 1), kaempferol, quercetin (Figure 1), quercitrin, rhamnazin and rutin [39–41]; drimane-typed sesquiterpenes, such as 3- β -angeloyloxy-7-epifutronolide, 7-ketoisodrimenin, changweikangic acid A, dendocarbin L, (+)-fuegin, futronolide, polygonumate, and (+)-winterin [42]; phenylpropanoid esters, including hydropiperosides A and B (Figure 1), and vanicosides A (Figure 1), B and E [43]; as well as phenolic acids, such as caffeic acid, chlorogenic acid and ρ -coumaric acid [41]. …”

LC–DAD–ESIMS/MS characterization of antioxidant and anticholinesterase constituents present in the active fraction from Persicaria hydropiper

“…MS/MS n yielded daughter ions at m/z 809 and at m/z 663, indicating the subsequent losses of 2 coumaroyl moieties, and at m/z 487 which indicated a further loss of feruloyl moiety. Peak 16 was therefore determined to be that of vanicoside B (Kiem et al, 2008). Meanwhile, peak 17, with [M-H] À ion at m/z 997, also lost of two coumaroyl moieties upon MS/MS n , subsequently giving ions at m/z 851 and m/z 705.…”

“…Other fragment ions were also observed at m/z 663 for [M-H-COCH 3 ] À and at m/z 487 which indicated a loss of a feruloyl moiety. Peak 16 was therefore identified to be that of vanicoside A (Kiem et al, 2008). Peaks 15e17 were determined as phenylpropanoid glucosides derivatives.…”