Phenolic acid derivatives with potential anticancer properties??a structure?activity relationship study. Part 1: Methyl, propyl and octyl esters of caffeic and gallic acids

Fiuza, Sónia M.

doi:10.1016/s0968-0896(04)00315-3

Cited by 56 publications

(77 citation statements)

References 20 publications

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“…Several caffeic acid alkyl esters have been reported to possess a wide array of biological activities (24,27). As reported earlier, reactive oxygen species play a significant role in the regulation of tumor cell growth and expression of COX-2 enzyme (28,29).…”

Section: Discussionmentioning

confidence: 83%

“…This indicated that hydrophilicity of these compounds may play a significant role in the antioxidant activity of these compounds. In contrast, the ferulic acid derivatives 15-23 (C 3 -C 12 ) were more active than their long-chain counterparts (22)(23)(24)(25)(26)(27) (Figure 4B). The conformational rigidity of the ferulates was one of the factors reported for their antioxidant activity (23).…”

Section: Discussionmentioning

confidence: 98%

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Impact of Alkyl Esters of Caffeic and Ferulic Acids on Tumor Cell Proliferation, Cyclooxygenase Enzyme, and Lipid Peroxidation

Bolleddula

Mulabagal

Zhang

et al. 2006

J. Agric. Food Chem.

138

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The antioxidant ferulic and caffeic acid phenolics are ubiquitous in plants and abundant in fruits and vegetables. We have synthesized a series of ferulic and caffeic acid esters and tested for tumor cell proliferation, cyclooxygenase enzymes (COX-1 and -2) and lipid peroxidation inhibitory activities in vitro. In the tumor cell proliferation assay, some of these esters showed excellent growth inhibition of colon cancer cells. Among the phenolics esters assayed, compounds 10 (C12-caffeate), 11 (C16-caffeate), 21 (C8-ferulate), and 23 (C12-ferulate) showed strong growth inhibition with IC50 values of 16.55, 13.46, 18.67, and 7.57 microg/mL in a breast cancer cell line; 9.65, 7.45, 17.05, and 4.35 microg/ mL in a lung cancer cell line; 5.78, 3.5, 4.29, and 2.46 microg/mL in a colon cancer cell line; 12.04, 12.21, 14.63, and 8.09 microg/ mL in a central nervous system cancer cell line; and 8.62, 7.76, 11.0, and 5.37 in a gastric cancer cell line. In COX enzyme inhibitory assays, ferulic and caffeic acid esters significantly inhibited both COX-1 and COX-2 enzymes. Caffeates 5-10 (C4-C12), inhibited COX-1 enzyme between 50% and 90% and COX-2 enzyme by about 70%, whereas ferulates 15-21 (C3-C8) inhibited COX-1 and COX-2 enzymes by 85-95% 25 microg/mL. Long-chain caffeates 11-14 (C16-C22) and short-chain ferulates 15-20 (C3-C5) were the most active in lipid peroxidation inhibition and showed 60-70% activity at 5 microg/mL concentration.

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Section: Discussionmentioning

confidence: 83%

Section: Discussionmentioning

confidence: 98%

Impact of Alkyl Esters of Caffeic and Ferulic Acids on Tumor Cell Proliferation, Cyclooxygenase Enzyme, and Lipid Peroxidation

Bolleddula

Mulabagal

Zhang

et al. 2006

J. Agric. Food Chem.

138

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“…In addition, shortening of the side chain resulted in the loss of antiproliferative activity and this was more apparent with the methylation of one or both hydroxyl groups and p-hydroxy substitution as in syringic and sinapic acids. Caffeic and gallic acids are known for their bioactivity related to modulation of carcinogenesis (Gomes et al, 2003;Fiuza et al, 2004). Characterization of phenolic composition of soluble extracts of millet showed that the quantity of caffeic acid of kodo and proso soluble extracts was 7% and 14% of the total hydroxycinnamic acids present, respectively (Chandrasekara & Shahidi, 2011b).…”

Section: Human Colon Adenocarcinoma Cell Proliferation Inhibitionmentioning

confidence: 99%

Antiproliferative potential and DNA scission inhibitory activity of phenolics from whole millet grains

Chandrasekara

Shahidi

2011

Journal of Functional Foods

166

110

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Singlet oxygen Liposome oxidationXanthine oxidase A B S T R A C T Phenolic extracts from seven millet varieties (kodo, finger (Ravi), finger (local) proso, foxtail, little and pearl) were evaluated for their total phenolic content (TPC), total flavonoid content (TFC), ferrous ion chelating activity and singlet oxygen scavenging capacity. Furthermore, the potency of millet phenolic extracts in the inhibition of peroxyl and hydroxyl radical induced supercoiled DNA scission, as well as xanthine oxidase and their antiprolifeative activities against HT-29 cells were studied. In addition, lipid peroxidation inhibition of extracts was examined in a liposome system. The TPC and TFC ranged from 146 to 1156 lmol ferulic acid equivalents and 25 to 1203 lmol catechin equivalents per gram crude extract, respectively. All varieties employed in this study exhibited a notable inhibition of lipid peroxidation in liposomes, singlet oxygen quenching and DNA scission inhibition to varying degrees. At the end of day 4 millet extracts inhibited cell proliferation in the range of 28-100%. Thus, the present study demonstrates that millet phenolics may be effective in the prevention of cancer initiation and progression in vitro. Millet grains may therefore serve as a nutraceutical and functional food ingredient in health promotion and disease risk reduction.

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“…Furthermore, the consumption of a phytochemicalrich diet (fruits and vegetables) decreases the risk of certain types of human cancers [8,9]. Gallic acid (3,4,5-trihydroxybenzoic acid, GA) has been shown to have many biological properties such as antibacterial [10], antifungal and antimalarial [11], antioxidant [12], and antiherpetic action [13]. GA induced apoptosis in human leukemia HL-60RG cells [14], lung cancer cell lines, stomach cancer KATO III, colon adenocarcinoma COLO 205 cell line [15], and rat pheochromocytoma PC12 cells [16].…”

Section: Introductionmentioning

confidence: 99%

Gallic acid inhibits the migration and invasion of A375.S2 human melanoma cells through the inhibition of matrix metalloproteinase-2 and Ras

Lai²,

Yang³

et al. 2011

Melanoma Research

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Melanoma is one of the most common cancers worldwide and its incidence has been increasing over the past few decades. Gallic acid (GA) can inhibit the growth of human cancer cells in vitro and in vivo. However, there is no available information to address the effects of GA on migration and invasion of human skin cancer cells. Matrix metalloproteinases (MMPs), zinc-dependent proteolytic enzymes, play an important role in the invasion, metastasis, and angiogenesis of cancer cells. Therefore, MMPs are one of the targets for agents to suppress and that could inhibit the migration and invasion of cancer cells. GA affected the viable A375.S2 cells by propidium iodide exclusion and flow cytometric analysis. Cell migration and invasion were investigated by Boyden chamber assay and we also determined the levels of protein and mRNA expression cell migration and invasion by gelatin zymography, western blotting, and real-time PCR assays. In this study, we examined the influence of GA on the protein levels and gene expression of MMP-2 and MMP-9 and in-vitro migration and invasiveness of human melanoma cells. GA decreases the MMPs and associated signal pathway protein and MMPs mRNA levels in A375.S2 human melanoma cells. Our findings suggest that GA has antimetastatic potential by decreasing invasiveness of cancer cells. Moreover, this action of GA was involved in the Ras, p-ERK signaling pathways resulting in inhibition of MMP-2 in A375.S2 human melanoma cells. These data, therefore, provide evidence for the role of GA as a potential cancer chemotherapeutic agent, which can markedly inhibit the invasive capacity of melanoma cells.

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Phenolic acid derivatives with potential anticancer properties??a structure?activity relationship study. Part 1: Methyl, propyl and octyl esters of caffeic and gallic acids

Cited by 56 publications

References 20 publications

Impact of Alkyl Esters of Caffeic and Ferulic Acids on Tumor Cell Proliferation, Cyclooxygenase Enzyme, and Lipid Peroxidation

Impact of Alkyl Esters of Caffeic and Ferulic Acids on Tumor Cell Proliferation, Cyclooxygenase Enzyme, and Lipid Peroxidation

Antiproliferative potential and DNA scission inhibitory activity of phenolics from whole millet grains

Gallic acid inhibits the migration and invasion of A375.S2 human melanoma cells through the inhibition of matrix metalloproteinase-2 and Ras

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