Mechanism of toxicity of esters of Caffeic and dihydrocaffeic acids

Etzenhouser, Beth; Hansch, Corwin; Kapur, Sanjay; Selassie, Cynthia Dias

doi:10.1016/s0968-0896(00)00238-8

Cited by 63 publications

(52 citation statements)

References 21 publications

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“…In addition, we reasoned that the disulfides 10,11) and a-mercaptocarbonyl group 12) would chelate zinc ion at the active-site of MMP-1, which renders them to be potential MMP inhibitors. In this work, the sulfur-containing cinnamates and salicylates of substituted ester group were synthesized and the potency of these compounds as UV protective agents was evaluated by analyzing their free radical scavenging and for MMP-1 inhibitory activities.Chemistry The synthetic routes [13][14][15] to the target compounds 5a, 5b, 6a, 6b and 7a, 7b are outlined in Charts 1 and 2. Reduction of 2-mercaptobenzoic acid with lithium aluminum hydride (LiAlH 4 ) in tetrahydrofuran resulted 2-mercaptobenzyl alcohol (1), followed by oxidation of 1 with pyridinium chlorochromate (PCC) in dichloromethane at room temperature afforded 2,2Ј-dithiodibenzadehyde (2).…”

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confidence: 99%

“…Chemistry The synthetic routes [13][14][15] to the target compounds 5a, 5b, 6a, 6b and 7a, 7b are outlined in Charts 1 and 2. Reduction of 2-mercaptobenzoic acid with lithium aluminum hydride (LiAlH 4 ) in tetrahydrofuran resulted 2-mercaptobenzyl alcohol (1), followed by oxidation of 1 with pyridinium chlorochromate (PCC) in dichloromethane at room temperature afforded 2,2Ј-dithiodibenzadehyde (2).…”

mentioning

confidence: 99%

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Synthesis and Biological Evaluation of Sulfur-Containing Cinnamate and Salicylate Derivatives

Chiang¹,

Chang

Tsai³

et al. 2008

CHEMICAL & PHARMACEUTICAL BULLETIN

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Human skin is the most susceptible organ to be damaged by ultraviolet (UV) irradiation as it is directly exposed to UV light. Increased evidence has shown the generation of reactive oxygen species (ROS) in the skin upon UV exposure. 1-3)Increased ROS generation can overwhelm the intracellular antioxidant-defense mechanism, resulting in oxidative stress and oxidative photo-damage to proteins and other macromolecules in the skin. Oxidative stress is thought to play a central role in initiating and driving the signaling events that lead to the cell response following exposure to UV irradiation. 4,5) Exposure of human skin to UV radiation causes numerous biological effects in the skin, including premature aging characterized by wrinkles, leathery texture and mottled pigmentation.6,7) The mechanism of skin wrinkles is primarily due to the loss of macromolecules making up the dermal matrix, among which collagen is the major component. The degradation of collagens is normally tightly controlled by the activity of a family of zinc-dependent matrix metalloproteinases (MMPs) and their natural inhibitors, the tissue inhibitors of MMPs (TIMPs). 8) Although several MMPs are expressed in mammalian skin, studies by Brennan et al. 3) showed that the neutralization of MMP-1 removed virtually all the collagen-degrading activity elaborated by UV-treated human skin.Cinnamates and salicylates are the chemical UV filter widely used throughout the world. 9) In this study, the ethyl and 2-ethylhexyl esters of these compounds were synthesized, as the presence of these groups may diminish the water solubility of these compounds to various degree, thus, may help to develop waterproof sunscreen formulation. 9) Because the radical scavenging ability of mercaptans and disulfides is well-documented, we speculated that the introduction of these important functional groups into cinnamates or salicylates might yield potent antioxidants and UV protectants. In addition, we reasoned that the disulfides 10,11) and a-mercaptocarbonyl group 12) would chelate zinc ion at the active-site of MMP-1, which renders them to be potential MMP inhibitors. In this work, the sulfur-containing cinnamates and salicylates of substituted ester group were synthesized and the potency of these compounds as UV protective agents was evaluated by analyzing their free radical scavenging and for MMP-1 inhibitory activities.Chemistry The synthetic routes [13][14][15] to the target compounds 5a, 5b, 6a, 6b and 7a, 7b are outlined in Charts 1 and 2. Reduction of 2-mercaptobenzoic acid with lithium aluminum hydride (LiAlH 4 ) in tetrahydrofuran resulted 2-mercaptobenzyl alcohol (1), followed by oxidation of 1 with pyridinium chlorochromate (PCC) in dichloromethane at room temperature afforded 2,2Ј-dithiodibenzadehyde (2). Triphenyl-phosphanylidene-acetic acid 2-ethyl-hexyl ester (4) was prepared from triphenylphosphine and bromo-acetic 2-ethyl-hexyl ester, which obtained from the reaction of bromoacetic acid with 2-ethyl-hexanol under toluenesulfonic acid in toluene at reflux te...

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confidence: 99%

mentioning

confidence: 99%

Synthesis and Biological Evaluation of Sulfur-Containing Cinnamate and Salicylate Derivatives

Chiang¹,

Chang

Tsai³

et al. 2008

CHEMICAL & PHARMACEUTICAL BULLETIN

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“…Chiang, Y.M., Lo, C.P., Chen, Y.P., Wang, S.Y., Yang, N.S., Kuo, effects of CAEE is inadequate, there are some reports about anti-inflammatory activity (Chiang et al, 2005) and its effect on cellular activity (Etzenhouser et al, 2001). We have found a report of CA on cell viability; however, ten times the amount of caffeic acid phenetyl ester (CAPE) was needed to show the same effect on cells (Chung et al, 2004).…”

Section: Referencesmentioning

confidence: 99%

Isolation and Identification by Cytoprotection Assay of Antioxidative Compound Contained in Vinegar Produced from Sweet Potato-Shochu Post-Distillation Slurry

Kawano

Morimura

Mori

et al. 2010

FSTR

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Vinegar was produced from rice-, barley-, and sweet potato-shochu distillery wastewater (post-distillation slurry) using aerobic acetic acid fermentation with Acetobacter pasteurianus NBRC 3283. Among these, vinegar produced from sweet potato-shochu post-distillation slurry showed the highest antioxidative effect on U937 cells. The active compound was isolated using reversed phase HPLC and identified as caffeic acid ethyl ester using 1 H-NMR and LC-MS. Caffeic acid ethyl ester as well as caffeic acid were contained in the vinegar produced from sweet potato-shochu post-distillation slurry. It was confirmed that caffeic acid ethyl ester showed an obvious antioxidative effect on U937 and HepG2 cells, but on the other hand caffeic acid did not. Caffeic acid ethyl ester was not determined in the vinegar produced from rice-and barley-shochu post-distillation slurry.Keywords: sweet potato-shochu post-distillation slurry, vinegar, caffeic acid ethyl ester, antioxidative effect, reversed phase HPLC

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“…Octylcaffeate had been synthesized from caffeic acid by exhaustive octanol-esterization according to Etzenhouser et al 10) In this study, octylcaffeate and CAPE (Sigma, St. Louis, MO, U.S.A.) were diluted in dimethylsulfoxide (DMSO) to make stock solutions of 1 mM, kept at 4°C and filtrated with a sterile filter just before use, and then added at the appropriate final concentrations to cultures of cells. Control cells were treated with the same amount of vehicle alone.…”

Section: Chemicalsmentioning

confidence: 99%

Octylcaffeate Induced Apoptosis in Human Leukemia U937 Cells

Ujibe

Kanno

Osanai

et al. 2005

Biological & Pharmaceutical Bulletin

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We found that octylcaffeate, a semisynthetic caffeic acid derivative, strongly inhibited the growth of human histiolytic lymphoma U937 cells in a dose-and time-dependent manner via apoptosis. Octylcaffeate induced the fragmentation of DNA into multiples of 180 bp (an apoptotic DNA ladder) and condensation of chromatin, and increased the percentage of hypodiploid cells detected with a flow cytometer. DNA fragmentation induced by octylcaffeate was inhibited by pretreatment with Z-DEVD-FMK and Z-Asp-CH 2 D-CB, an inhibitor of caspase, clearly showing that the mode of cell death is apoptotic. These findings suggest that the cytotoxicity of octylcaffeate involves the induction of apoptosis.

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Mechanism of toxicity of esters of Caffeic and dihydrocaffeic acids

Cited by 63 publications

References 21 publications

Synthesis and Biological Evaluation of Sulfur-Containing Cinnamate and Salicylate Derivatives

Synthesis and Biological Evaluation of Sulfur-Containing Cinnamate and Salicylate Derivatives

Isolation and Identification by Cytoprotection Assay of Antioxidative Compound Contained in Vinegar Produced from Sweet Potato-Shochu Post-Distillation Slurry

Octylcaffeate Induced Apoptosis in Human Leukemia U937 Cells

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