Cytotoxic Allyl Retrochalcone from the Roots of Glycyrrhiza inflata

Abstract

Two known retrochalcones, licochalcone A (1) and licochalcone C (2), and one new retrochalcone, licochalcone E (4) were isolated by cytotoxicity-guided fractionation from the roots of Glycyrrhiza inflata along with an ordinary chalcone, isoliquiritigenin (3). The structure of the new retrochalcone was elucidated through a spectroscopic analysis.

Induction of Apoptosis by the Licochalcone E in Endothelial Cells via Modulation of NF-.KAPPA.B and Bcl-2 Family

“…1) Although cell culture study has revealed concerning the cytotoxic effects of Lico-E on human tumor cells, 1) the molecular mechanisms of Lico-E for the cytotoxic effects were not addressed. In order to understand the apoptosis-inducing potential of Lico-E in cultured endothelial cells, human endothelial ECV 304 cells, which had undergone spontaneous immortalization from human umbilical vein endothelial cells, were used.…”

“…We and other researchers identified the unusual phenolic compounds from Glycyrrhiza inflate, 1) known as retrochalcones, which are a form of normal chalcones that are structurally distinguished by the lack of oxygen functionalities at C-2Ј and C-6Ј (Fig. 1).…”

“…Thus far, six retrochalcones, licochalcones A-E and echinatin, have been isolated and characterized from the roots of Glycyrrhiza inflata. [1][2][3][4] These phenolic compounds were reported to inhibit the growth of new blood vessels in animals, 5,6) suggesting a mechanistic link between the consumption of polyphenolic flavonoids and the possible prevention and treatment of angiogenesis-dependent diseases such as cancer. Previous studies have also shown that a treatment with the tea flavonol, (Ϫ)-epigallocatechin-3-gallate, resulted in remarkable decrease in endothelial apoptosis in human ECV304 cells and human tumor xenografts introduced to nude mice.…”

Isolation, cloning and bioinformatics analysis of β-amyrin 11-oxidase coding sequence from licorice

“…It has a wide range of pharmacological, anti-bacterial and anti-oxidant activities (Varsha et al, 2013), hepato-protective (Chan et al, 2003;Jeong et al, 2002;Kimura et al, 2001), antiulcer (He et al, 2001), antiallergy (Park et al, 2004). anticancer (Fiore et al, 2004;Salvi et al, 2003;Yoon et al, 2005), antiviral activity against various DNA and RNA viruses (Fiore et al, 2008), including HIV (De Clercq, 2000) and severe acute respiratory syndrome-associated coronavirus (Cinatl et al, 2003). Biosynthesis of triterpenoids in licorice starts with conversion of two molecules farnesyl diphosphate (FDP) by the squalene synthase enzyme (SQS) to squalene (Lu et al, 2008).…”

Semisynthesis of Licochalcone E and Biological Evaluation as Vasorelaxant Agents

“…[1][2][3][4] Although licochalcones A-D reportedly exhibit various biological activities, [5][6][7][8][9][10][11][12][13][14][15] the search for the biological activities of licochalcone E is only in the initial stage of intensive studies due to its recent discovery. Licochalcone E exhibits topoisomerase 1 inhibition 13 and induces endothelial cell apoptosis by modulating NF-kB and the Bcl-2 family.…”