Binding of Filamentous Actin and Winding into Fibrillar Aggregates by the Polyphenolic C‐Glucosidic Ellagitannin Vescalagin

Abstract

Winding it up: The plant polyphenolic metabolite vescalagin fulfills all the requirements for use as an antiactin agent in cellular biological investigations. Despite its high hydrophilicity, it rapidly enters cells and disturbs the organization of the actin cytoskeleton in a dose‐dependent reversible manner by binding fibrillar actin and forcing the actin filaments (left) to wind themselves into ball‐like fibrillar aggregates (right).

An off–on fluorescent probe based on maleimide for detecting thiols and its application for bioimaging

“…Probe 1 was synthesized using a modification of a literature method [53]. Amino acids were purchased from Shanghai Experiment Reagent Co., Ltd (Shanghai, China).…”

Bioinspired Total Synthesis of (−)‐Vescalin: A Nonahydroxytriphenoylated C‐Glucosidic Ellagitannin

“…This initial success laid some of the groundwork for the next and primary challenge of accomplishing the chemical synthesis of a terarylic NHTP‐bearing C ‐glucosidic ellagitannin. Herein, we thus describe the first total synthesis of (−)‐vescalin ( 1 ), which is known for exhibiting valuable biological activities, notably as a potent inhibitor of human DNA topoisomerase IIα in vitro, and as an anti‐actin agent in cellulo . Its natural abundance in fagaceous species is highly variable and rather low (ca.…”

Flavonolignan Conjugates as DNA‐binding Ligands and Topoisomerase I Inhibitors: Electrochemical and Electrophoretic Approaches

“…Evaluation of redox activity,c hemical reactivity and molecular interactions of biologically activec ompounds is ap ivotal step towards better understanding theirm echanisms of action [5][6][7]. Ther edox properties of SB and also other silymarin flavonolignansh ave been fully rationalized bothe xperimentally and theoretically [1].T he role of individual hydroxy groups in electrochemical oxidation as wella st he free radical-scavenging effects of SB and DHSB were evaluatedi ns tructure-activity relationship (SAR) studies performed with selectively methylated derivatives [8] and conjugates [9].T he C-20 OH groupo f SB and botht he C-3 OH and C-20 OH groups of DHSB exhibitedamajor role in their electron donor properties and capacity to scavenge free radicals.…”

“…isosilybin, silychristin, silydianin and some others.2 ,3-Dehydrosilybin( DHSB) occurs in silymarin as am inor component, but it can be easily prepared fromS B[ 1]. Flavonolignans from silymarin are used as chemoprotective and especially hepatoprotective agents, and they are employed in ap lethora of nutraceuticals [2][3][4].Apleiotropic mode of action appears to be typical for these compounds [2,4].Evaluation of redox activity,c hemical reactivity and molecular interactions of biologically activec ompounds is ap ivotal step towards better understanding theirm echanisms of action [5][6][7]. Ther edox properties of SB and also other silymarin flavonolignansh ave been fully rationalized bothe xperimentally and theoretically [1].T he role of individual hydroxy groups in electrochemical oxidation as wella st he free radical-scavenging effects of SB and DHSB were evaluatedi ns tructure-activity relationship (SAR) studies performed with selectively methylated derivatives [8] and conjugates [9].T he C-20 OH groupo f SB and botht he C-3 OH and C-20 OH groups of DHSB exhibitedamajor role in their electron donor properties and capacity to scavenge free radicals.…”