Cytotoxic Evaluation against Breast Cancer Cells of Isoliquiritigenin Analogues from Spatholobus suberectus and Their Synthetic Derivatives

Abstract

Five isoliquiritigenin analogues, including a new methylene-bridged bischalcone (1), were isolated from Spatholobus suberectus. Cytotoxicity screening of these isolates and several synthetic derivatives indicated that the introduction, removal, position modification, or glycosylation of hydroxy groups in isoliquiritigenin did not improve the resultant cytotoxicity against the MCF-7 and MDA-MB-231 human breast cancer cell lines. In addition, cyclization of OH-2' chalcones or reduction of the α,β-unsaturated carbonyl double bond decreased such cytotoxicity substantially. However, methylation of hydroxy groups resulted in a marked increase in such cytotoxic activity. Among these active isoliquiritigenin analogues, 3',4',5',4″-tetramethoxychalcone (3h) was obtained as a compound with promising cytotoxic activity.

Isoliquiritigenin Derivative Regulates miR-374a/BAX Axis to Suppress Triple-Negative Breast Cancer Tumorigenesis and Development

“…Interestingly, we previously identified a natural flavonoid, ISL, with cytotoxic effects on MDA-MB-231 proliferation. We synthesized an ISL derivative, TMC, with a stronger inhibitory effect on TNBC cell growth (Peng et al, 2016a). In the present study, we first found that TMC inhibited TNBC cell foci formation, migration, and invasion.…”

“…TMC was prepared as previously described (referred as compound 3 h) (Peng et al, 2016a), and its purity was >98%. Xylene, eosin Y, hematoxylin, and other commonly used chemicals were purchased from Sigma (St. Louis, MO).…”

“…Isoliquiritigenin (ISL), a natural flavonoid extracted from S. suberectus, exerts potent anti-cancer effects during breast cancer development (Lorusso and Marech, 2013;Wang et al, 2013a). In a previous study, we modified the ISL structure, synthesized its derivatives and found 3′,4′,5′,4″-tetramethoxychalcone (TMC) ( Figure 1, Table S1) had a greater inhibitory effect on breast cancer cell viability than ISL, especially on MDA-MB-231 cells (Peng et al, 2016a). Further study found that it had a better antibreast cancer effect on TNBC cells than cisplatin ( Figure S1).…”

Cytotoxic, Anti-bacterial, and Wound-healing Activity of Prenylated Phenols from the Kurdish Traditional Medicinal Plant Onobrychis Carduchorum (Fabaceae)

“…Similarly, two stilbenes isolated from the Nigerian plant Cajanus cajan proved the capability to interfere with the viability of different cancer cell lines, including MCF-7 [11]. Finally, five isoliquiritigenin chalcones isolated from Spatholobus suberectus, and some synthetic analogues, were evaluated for their cytotoxic potential against the MCF-7 and MDA-MB-231 breast cancer cells [12].…”

UPLC–MS/MS assay for simultaneous determination of four compounds in rat plasma: application to pharmacokinetic study after oral administration of Caulis Spatholobi extract

“…To date, most studies have focused on its pharmacological and chemical aspects. Modern pharmacological studies revealed that the herb possesses various pharmacological effects, including improvement in blood circulation, inhibition of osteoclast differentiation and bone resorption, and anti-cancer, antiplatelet, anti-inflammation and antiviral properties Lee et al, 2011;Pang et al, 2011;Peng et al, 2016;Ha et al, 2013). Recent studies have shown that the extract of S. suberectus can remarkably inhibit platelet aggregation and thrombosis (Li et al, 2015;Zhang and Wang, 2013).…”