Hydrogen Bond Formation as Basis For Radical Scavenging Activity: A Structure–Activity Study of C-Methylated Dihydrochalcones from Myrica gale and Structurally Related Acetophenones

The ABTS•+ radical cation scavenging activity of known (2-5, 9, 10) and new (6-8) 1’-hydroxyethylnaphthazarins and their products of esterification and etherification was evaluated and a structure-activity relationship was studied. It was shown, that the structure of side chains does not affect the radical scavenging activity of 1’-hydroxyethylnaphthazarins and their derivatives. The presence of methoxyl groups on the naphthazarin core slightly enhanced the antioxidant activity of compounds compared with compounds without methoxyl groups. The presence of the additional hydroxyl group on the naphthazarin moiety of isonorlomazarin (5) and its derivative (6) is essential for the activity.

Download Full-text

Density Functional Theory Calculations of the Radical Scavenging Activity of Alkannin Derivatives

Applied Mechanics and Materials ◽

10.4028/www.scientific.net/amm.189.225 ◽

2012 ◽

Vol 189 ◽

pp. 225-231

Author(s):

Xiang Peng Guo ◽

Rui Fa Jin

Keyword(s):

Density Functional ◽

Radical Scavenging Activity ◽

Radical Scavenging ◽

Density Functional Theory Calculations ◽

Hydrogen Atom Transfer ◽

Scavenging Activity ◽

Functional Theory ◽

Hydrogen Bond Formation ◽

Structural And Electronic Properties ◽

The One

The structural and electronic properties of alkannin and its derivatives and their radicals were investigated at density functional level. It turned out that the presence of the dihydroxy functionality increases the radical stability through hydrogen bond formation. The hydrogen atom transfer for alkannin derivatives is difficult to occur compared with zero compound phenol. However, alkannin derivatives appear to be good candidates for the one-electron-transfer, particularly for alkannin derivatives with –OCOCH=CH(CH3)2 and –OCOCH2CH(CH3)2 groups. It suggests that 1–7 are expected to be the promising candidates for radical scavenging activity compounds because The ionization potential (IP) values of 1–7 are lower than that of the zero compound phenol.

Download Full-text

Evaluation of the radical scavenging activity of a series of synthetic hydroxychalcones towards the DPPH radical

Journal of the Serbian Chemical Society ◽

10.2298/jsc100517043t ◽

2011 ◽

Vol 76 (4) ◽

pp. 491-497 ◽

Cited By ~ 10

Author(s):

Iva Todorova ◽

Daniela Batovska ◽

Bistra Stamboliyska ◽

Stoyan Parushev

Keyword(s):

Radical Scavenging Activity ◽

Radical Scavenging ◽

Experimental Results ◽

Scavenging Activity ◽

Dpph Radical ◽

Structure Activity Relationships ◽

Aryl Aldehydes ◽

Structure Activity ◽

Dpph Radical Scavenging ◽

Important Structure

Sixteen hydroxychalcones were synthesized in sufficient purity by the Claisen-Schmidt condensation between appropriate acetophenones and aryl aldehydes. All the compounds were evaluated for their ability to scavenge the stable free 2,2-diphenyl-1-picrylhydrazyl (DPPH) radical. Important structure-activity relationships were observed that strongly contribute to the knowledge for the design of DPPH radical scavenging chalcones. Relevant theoretical parameters were computed in an attempt to understand and explain the obtained experimental results.

Download Full-text

A New Chlorine-containing Glucosyl-fused Compound from Curculigo glabrescens

Zeitschrift für Naturforschung B ◽

10.1515/znb-2009-0914 ◽

2009 ◽

Vol 64 (9) ◽

pp. 1077-1080 ◽

Cited By ~ 8

Author(s):

Cui-Cui Zhu ◽

Tian-Ming Wang ◽

Kai-Jin Wang ◽

Ning Li

Keyword(s):

Spectroscopic Analysis ◽

Radical Scavenging Activity ◽

Radical Scavenging ◽

2D Nmr ◽

Free Radical Scavenging ◽

Scavenging Activity ◽

Dpph Assay ◽

Etoh Extract ◽

Structure Activity ◽

First Time

A new chlorine-containing glucosyl-fused compound, crassifoside H (1), was isolated from the EtOH extract of the rhizomes of Curculigo glabrescens. The structure was established on the basis of MS, IR, 1D and 2D NMR experiments. In addition, seven known compounds (2 - 8) were isolated and identified by spectroscopic analysis and comparison of their spectral data with those reported previously. All the compounds were isolated from this plant for the first time. The free radical scavenging activity of the isolated compounds was evaluated by the 1,1-diphenyl-2-picrylhydrazyl (DPPH) assay. Compounds 1 and 2 showed strong radical scavenging activities. The primary structure-activity relationship is also discussed.

Download Full-text