Antiproliferative activity and SARs of caffeic acid esters with mono-substituted phenylethanols moiety

Xie, Jin; Yang, Fulun; Zhang, Man; Lam, Celine; Qiao, Yixue; Jia, Xiaohong; Zhang, Dongdong; Ge, Yuxuan; Fu, Lei; Xie, Dongsheng

doi:10.1016/j.bmcl.2016.12.007

Cited by 27 publications

(11 citation statements)

References 23 publications

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“…Chlorogenic acid and caffeic acid are common bioactive compounds [34,35]. Chlorogenic acid has the effect of protecting liver, inhibits cancer cell growth and has a beneficial effect on ameliorating aging-related diseases [24].…”

Section: Results and Discussion Sections In Wrong Order—experimentmentioning

confidence: 99%

Bioactive Constituents of F. esculentum Bee Pollen and Quantitative Analysis of Samples Collected from Seven Areas by HPLC

Guo

Zhang

et al. 2019

Molecules

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Bee pollen contains all the essential amino acids needed by humans. China is the largest producer of bee pollen in the world. In the present study, we identified 11 fatty acids in F. esculentum bee pollen oil by GC-MS analysis, and 16 compounds were isolated from F. esculentum bee pollen by column chromatography and identified. A high-performance liquid chromatography-diode array detector (HPLC-DAD) method was established for the quality control of F. esculentum bee pollen. A validated HPLC-DAD method was successfully applied to the simultaneous characterization and quantification of nine main constituents in seven samples collected from seven different areas in China. The results showed that all standard calibration curves exhibited good linearity (R2 > 0.999) in HPLC-DAD analysis with excellent precision, repeatability and stability. The total amount in the samples from the seven regions ranged from 23.50 to 46.05 mg/g. In addition, seven compounds were studied for their bioactivity using enzymic methods, whereby kaempferol (3) showed high α-glucosidase inhibitory activity (IC50: 80.35 μg/mL), ergosterol peroxide (8) showed high tyrosinase inhibitory activity (IC50: 202.37 μg/mL), and luteolin (1) had strong acetylcholinesterase inhibitory activity (IC50: 476.25 μg/mL). All results indicated that F. esculentum bee pollen could be a nutritious health food.

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Section: Results and Discussion Sections In Wrong Order—experimentmentioning

confidence: 99%

Bioactive Constituents of F. esculentum Bee Pollen and Quantitative Analysis of Samples Collected from Seven Areas by HPLC

Guo

Zhang

et al. 2019

Molecules

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“…The preparation of less polar esters of caffeic acid tends to produce compounds that have moderate to excellent lipoxygenase inhibition [ 14 , 31 , 32 ]. As shown in Figure 4 , esterification of caffeic acid with various phenethyl alcohol derivatives ( 7 [ 33 ], 8 [ 33 ], 9 , 22 , 23 [ 33 ] and 24 [ 34 ]) produced compounds with notable inhibitory activity at 1 µM, ranging from 50 to 70% inhibition of 5-LO product synthesis. It is noteworthy that inhibition values are fairly insensitive to modifications of the phenethyl portion of these compounds, with only moderate reduction in inhibition even with the bulky 3,4-dimethoxy substitution ( 9 ) and highly polar 3,4-dihydroxy substitution ( 24 ).…”

Section: Resultsmentioning

confidence: 99%

Substituted Caffeic and Ferulic Acid Phenethyl Esters: Synthesis, Leukotrienes Biosynthesis Inhibition, and Cytotoxic Activity

et al. 2017

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Glioblastoma multiforme (GBM) is an aggressive brain tumor that correlates with short patient survival and for which therapeutic options are limited. Polyphenolic compounds, including caffeic acid phenethyl ester (CAPE, 1a), have been investigated for their anticancer properties in several types of cancer. To further explore these properties in brain cancer cells, a series of caffeic and ferulic acid esters bearing additional oxygens moieties (OH or OCH3) were designed and synthesized. (CAPE, 1a), but not ferulic acid phenethyl ester (FAPE, 1b), displayed substantial cytotoxicity against two glioma cell lines. Some but not all selected compounds derived from both (CAPE, 1a) and (FAPE, 1b) also displayed cytotoxicity. All CAPE-derived compounds were able to significantly inhibit 5-lipoxygenase (5-LO), however FAPE-derived compounds were largely ineffective 5-LO inhibitors. Molecular docking revealed new hydrogen bonds and π-π interactions between the enzyme and some of the investigated compounds. Overall, this work highlights the relevance of exploring polyphenolic compounds in cancer models and provides additional leads in the development of novel therapeutic strategies in gliomas.

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“…In vitro and in vivo experiments have been performed, proving innumerable physiological effects of CA and its derivatives, such as antibacterial activity (1, 4), antiviral activity (2, 5, 8, 9), antioxidant activity (2, 4, 5, 8, 9), anti-inflammatory activity (2, 4, 5, 8, 9), anti-atherosclerotic activity (1, 4), immunostimulatory activity (1, 10), antidiabetic activity (5, 9), cardioprotective activity (5, 11), antiproliferative activity (1, 12, 13), hepatoprotective activity (14, 15), anticancer activity (2, 4, 5, 8, 9), and anti-hepatocellular carcinoma activity (16–18). Among these properties, anti-hepatocarcinoma activity is highlighted, because hepatocarcinoma (HCC) is one of the main causes of cancer mortality in the world (19).…”

Section: Introductionmentioning

confidence: 99%

Chemical and Pharmacological Aspects of Caffeic Acid and Its Activity in Hepatocarcinoma

et al. 2019

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Caffeic acid (CA) is a phenolic compound synthesized by all plant species and is present in foods such as coffee, wine, tea, and popular medicines such as propolis. This phenolic acid and its derivatives have antioxidant, anti-inflammatory and anticarcinogenic activity. In vitro and in vivo studies have demonstrated the anticarcinogenic activity of this compound against an important type of cancer, hepatocarcinoma (HCC), considered to be of high incidence, highly aggressive and causing considerable mortality across the world. The anticancer properties of CA are associated with its antioxidant and pro-oxidant capacity, attributed to its chemical structure that has free phenolic hydroxyls, the number and position of OH in the catechol group and the double bond in the carbonic chain. Pharmacokinetic studies indicate that this compound is hydrolyzed by the microflora of colonies and metabolized mainly in the intestinal mucosa through phase II enzymes, submitted to conjugation and methylation processes, forming sulphated, glucuronic and/or methylated conjugates by the action of sulfotransferases, UDP-glucotransferases, and o-methyltransferases, respectively. The transmembrane flux of CA in intestinal cells occurs through active transport mediated by monocarboxylic acid carriers. CA can act by preventing the production of ROS (reactive oxygen species), inducing DNA oxidation of cancer cells, as well as reducing tumor cell angiogenesis, blocking STATS (transcription factor and signal translation 3) and suppression of MMP2 and MMP-9 (collagen IV metalloproteases). Thus, this review provides an overview of the chemical and pharmacological parameters of CA and its derivatives, demonstrating its mechanism of action and pharmacokinetic aspects, as well as a critical analysis of its action in the fight against hepatocarcinoma.

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Antiproliferative activity and SARs of caffeic acid esters with mono-substituted phenylethanols moiety

Cited by 27 publications

References 23 publications

Bioactive Constituents of F. esculentum Bee Pollen and Quantitative Analysis of Samples Collected from Seven Areas by HPLC

Bioactive Constituents of F. esculentum Bee Pollen and Quantitative Analysis of Samples Collected from Seven Areas by HPLC

Substituted Caffeic and Ferulic Acid Phenethyl Esters: Synthesis, Leukotrienes Biosynthesis Inhibition, and Cytotoxic Activity

Chemical and Pharmacological Aspects of Caffeic Acid and Its Activity in Hepatocarcinoma

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