Antioxidation Mechanism Studies of Caffeic Acid: Identification of Antioxidation Products of Methyl Caffeate from Lipid Oxidation

2008 ◽  
Vol 56 (14) ◽  
pp. 5947-5952 ◽  
Author(s):  
Toshiya Masuda ◽  
Kazuki Yamada ◽  
Jun Akiyama ◽  
Tatsushi Someya ◽  
Yuka Odaka ◽  
...  
Keyword(s):  
Lipid Oxidation ◽  
Caffeic Acid ◽  
Methyl Caffeate ◽  
Antioxidation Mechanism

Active films from water-soluble chitosan/cellulose composites incorporating releasable caffeic acid for inhibition of lipid oxidation in fish oil emulsions

2013 ◽  
Vol 32 (1) ◽  
pp. 9-19 ◽  
Author(s):  
Shu-Huei Yu ◽  
Hao-Ying Hsieh ◽  
Jen-Chieh Pang ◽  
Deh-Wei Tang ◽  
Chwen-Ming Shih ◽  
...  
Keyword(s):  
Fish Oil ◽  
Lipid Oxidation ◽  
Caffeic Acid ◽  
Water Soluble ◽  
Cellulose Composites ◽  
Oil Emulsions

scholarly journals Constituents of Xerolekia speciosissima (L.) Anderb. (Inuleae), and Anti-Inflammatory Activity of 7,10-Diisobutyryloxy-8,9-epoxythymyl Isobutyrate

Molecules ◽  
2020 ◽  
Vol 25 (21) ◽  
pp. 4913 ◽  
Author(s):  
Natalia Kłeczek ◽  
Janusz Malarz ◽  
Barbara Gierlikowska ◽  
Anna K. Kiss ◽  
Anna Stojakowska
Keyword(s):  
Caffeic Acid ◽  
Human Neutrophils ◽  
Hydroalcoholic Extract ◽  
The North ◽  
Thymol Derivatives ◽  
Aerial Parts ◽  
Dicaffeoylquinic Acid ◽  
Medicinal Properties ◽  
Methyl Caffeate ◽  
Dehydrodiconiferyl Alcohol

Xerolekia speciosissima (L.) Anderb., a rare plant from the north of Italy, is a member of the Inuleae-Inulinae subtribe of the Asteraceae. Despite its close taxonomic relationship with many species possessing medicinal properties, the chemical composition of the plant has remained unknown until now. A hydroalcoholic extract from the aerial parts of X. speciosissima was analyzed by HPLC-DAD-MSn, revealing the presence of caffeic acid derivatives and flavonoids. In all, 19 compounds, including commonly found chlorogenic acids and less frequently occurring butyryl and methylbutyryl conjugates of dicaffeoylquinic and tricaffeoylhexaric acids, plus two flavonoids, were tentatively identified. Chromatographic separation of a hydroalcoholic extract from the capitula of the plant led to the isolation of (+)-dehydrodiconiferyl alcohol 4-O-β-glucopyranoside, quercimeritrin, astragalin, isoquercitrin, 6-hydroxykaempferol-7-O-β-glucoside, quercetagitrin, methyl caffeate, caffeic acid, protocatechuic acid, chlorogenic acid and 1,5-dicaffeoylquinic acid. Composition of a nonpolar extract from the aerial parts of the plant was analyzed by chromatographic methods supported with 1H-NMR spectroscopy. The analysis revealed the presence of loliolide, reynosin, samtamarine, 2,3-dihydroaromaticin, 2-deoxy-4-epi-pulchellin and thymol derivatives as terpenoid constituents of the plant. One of the latter compounds—7,10-diisobutyryloxy-8,9-epoxythymyl isobutyrate—at concentrations 0.5, 1.0 and 2.5 μM, significantly reduced IL-8, IL-1β and CCL2 excretion by LPS-stimulated human neutrophils.

scholarly journals Interactive Effects of Wide-Spectrum Monochromatic Lights on Phytochemical Production, Antioxidant and Biological Activities of Solanum xanthocarpum Callus Cultures

Molecules ◽  
2020 ◽  
Vol 25 (9) ◽  
pp. 2201 ◽  
Author(s):  
Hazrat Usman ◽  
Muhammad Asad Ullah ◽  
Hasnain Jan ◽  
Aisha Siddiquah ◽  
Samantha Drouet ◽  
...  
Keyword(s):  
Secondary Metabolites ◽  
Caffeic Acid ◽  
Blue Light ◽  
Callus Culture ◽  
Biological Activities ◽  
Callus Cultures ◽  
Anti Inflammatory ◽  
Methyl Caffeate ◽  
Solanum Xanthocarpum

Solanum xanthocarpum is considered an important traditional medicinal herb because of its unique antioxidant, and anti-diabetic, anti-aging, and anti-inflammatory potential. Because of the over exploitation linked to its medicinal properties as well as destruction of its natural habitat, S. xanthocarpum is now becoming endangered and its supply is limited. Plant in vitro culture and elicitation are attractive alternative strategies to produce biomass and stimulate biosynthesis of medicinally important phytochemicals. Here, we investigated the potential influence of seven different monochromatic light treatments on biomass and secondary metabolites accumulation in callus culture of S. xanthocarpum as well as associated biological activities of the corresponding extracts. Among different light treatments, highest biomass accumulation was observed in white light-treated callus culture. Optimum accumulation of total flavonoid contents (TFC) and total phenolic contents (TPC) were observed in callus culture kept under continuous white and blue light respectively than control. Quantification of phytochemicals through HPLC revealed that optimum production of caffeic acid (0.57 ± 0.06 mg/g DW), methyl-caffeate (17.19 mg/g ± 1.79 DW), scopoletin (2.28 ± 0.13 mg/g DW), and esculetin (0.68 ± 0.07 mg/g DW) was observed under blue light callus cultures. Compared to the classic photoperiod condition, caffeic acid, methyl-caffeate, scopoletin, and esculetin were accumulated 1.7, 2.5, 1.1, and 1.09-folds higher, respectively. Moreover, high in vitro cell free antioxidant, anti-diabetic, anti-aging, and anti-inflammatory activities were closely associated with the production of these secondary metabolites. These results clearly showed the interest to apply multispectral light as elicitor of in vitro callus cultures S. xanthocarpum to promote the production of important phytochemicals, and allow us to propose this system as an alternative for the collection of this endangered species from the wild.

Novel interactions of caffeic acid with different hemoglobins: Effects on discoloration and lipid oxidation in different washed muscles

Meat Science ◽  
2013 ◽  
Vol 95 (1) ◽  
pp. 110-117 ◽  
Author(s):  
Sung Yong Park ◽  
Ingrid Undeland ◽  
Thippeswamy Sannaveerappa ◽  
Mark P. Richards
Keyword(s):  
Lipid Oxidation ◽  
Caffeic Acid ◽  
Novel Interactions

scholarly journals A study of esterification of caffeic acid with methanol using p-toluenesulfonic acid as a catalyst

2013 ◽  
Vol 78 (7) ◽  
pp. 1023-1034 ◽  
Author(s):  
Jun Wang ◽  
Shuangshuang Gu ◽  
Na Pang ◽  
Fangqin Wang ◽  
Fuan Wu
Keyword(s):  
Caffeic Acid ◽  
Molar Ratio ◽  
Forward Rate ◽  
Limiting Factor ◽  
High Catalytic Activity ◽  
Efficient Catalyst ◽  
Toluenesulfonic Acid ◽  
Melting Point Analysis ◽  
Point Analysis ◽  
Methyl Caffeate

Caffeic acid (CA) can be considered as an important natural antioxidant. However, the low solubility and stability of CA in various solvent systems is a major limiting factor governing the overall application in the lipid industry, so the synthesis of methyl caffeate (MC)using CA and methanol is a feasible way to improve its lipophilicity. Here, the reaction conditions and kinetic parameters for the synthesis of MC using p-toluenesulfonic acid (PTSA) as a catalyst were firstly investigated, and the product was confirmed byliquid chromatography-mass spectrometry (LC-MS),Fourier transform infrared spectroscopy (FTIR), nuclear magnetic resonance (NMR), and melting point analysis. The highest yield of MC catalyzed by PTSA reached 84.0% under the optimum conditions as follows: molar ratio of methanol to CA of 20:1, reaction temperature of 65?C, mass ratio of catalyst to substrate of 8 %, and reaction time of 4 h. The esterification kinetics of CA and methanol is described by the pseudo-homogeneous second order reversible model, the relationship between temperature and the forward rate constant is k1 = exp (358.7 - 2111/T), and the activation energy is 17.5 kJ mol-1. These results indicated that the PTSA possesses high catalytic activity in the synthesis of MC, which is an efficient catalyst suitable for MC production in the chemical industry.

scholarly journals Butylated methyl caffeate: a novel antioxidant

2020 ◽  
Vol 71 (2) ◽  
pp. 352
Author(s):  
Q. Q. Chen ◽  
H. Pasdar ◽  
X. C. Weng
Keyword(s):  
Antioxidant Activity ◽  
Caffeic Acid ◽  
Radical Scavenging Activity ◽  
Radical Scavenging ◽  
The Other ◽  
Lipid Phase ◽  
Hydroxyl Groups ◽  
Dpph Radical ◽  
Methyl Caffeate ◽  
Dpph Radical Scavenging

A novel caffeic acid derivative, butylated methyl caffeate (BMC), was synthesized via esterification between butylated caffeic acid (BCA) and methanol. Its antioxidant activity was investigated and compared to TBHQ, caffeic acid (CA), methyl caffeate (MC) and BCA through deep-frying, an oven test in oil-in-water emulsions and DPPH radical scavenging. BMC showed the strongest antioxidant activity among the five anti­oxidants in emulsions and its antioxidant activity was almost as strong as BCA in frying. Its soybean oil-water partition coefficient was 9.18 due to its ester and tert-butyl groups, far greater than those of MC (4.82), BCA (2.41), CA (0.84) and TBHQ (3.22). This meant that it was much more soluble in the lipid phase than the other four antioxidants in emulsions. The DPPH radical scavenging activity of BMC was near TBHQ, lower than the other three because of its steric hindrance and less functional phenolic hydroxyl groups compared to others when their masses were the same.

scholarly journals Compounds Isolated from the Ethyl Acetate Fraction of Canna edulis Ker Gawl Rhizomes

2021 ◽  
Vol 37 (2) ◽  
Author(s):  
Nguyen Thi Van Anh ◽  
Le Hong Luyen ◽  
Nguyen Thi Minh Hang ◽  
Vu Thi Thom ◽  
Bui Thanh Tung
Keyword(s):  
Antioxidant Activity ◽  
Secondary Metabolites ◽  
Caffeic Acid ◽  
Southern China ◽  
Chemical Constituents ◽  
Docking Simulation ◽  
Inhibitory Effect ◽  
Structural Constraints ◽  
Raw264.7 Macrophages ◽  
Methyl Caffeate

Three compounds were isolated from the rhizome part of Canna edulis for the first time including liquiritigenin, methyl caffeate and uracil. Their structures were elucidated by spectroscopic methods as MS and NMR. Keywords Canna edulis Ker Gawl, liquiritigenin, methyl caffeate, uracil. References [1] T. H. Vu, Q. U. Le, Edible Canna (Canna edulis Ker), A Potential Crop for Vietnam Food Industry, International Journal of Botany Studies, Vol. 4, No. 4, 2019, pp. 58–59.[2] N. Tanakar, The Utilization of Edible Canna Plants in Southeastern Asia and Southern China, Economic Botany, Vol. 58, No. 1, 2004, 112–114.[3] A. S. A. Snafi, Bioactive Components and Pharmacological Effects of Canna indica - an Overview, International Journal of Pharmacology and Toxicology, Vol. 5, No. 2, 2015, pp. 71–75.[4] X. J. Zhang, Z. W. Wang, Q. Mi, Phenolic Compounds from Canna edulis Ker Residue and Their Antioxidant Activity, LWT - Food Science Technology, Vol. 44, No. 10, 2011, pp. 2091–2096, https://doi.org/10.1016/j.lwt.2011.05.021. [5] F. Xie, S. Gong, W. Zhang, J. Wu, Z. Wang, Potential of Lignin from Canna edulis Ker Residue in The Inhibition of α-d-glucosidase: Kinetics and Interaction Mechanism Merging with Docking Simulation, International Journal of Biology and Macromolecules, Vol. 95, 2017, pp. 592–602, https://doi.org/10.1016/j.ijbiomac.2016.11.100.[6] J. Zhang, Z. W. Wang, Soluble Dietary Fiber from Canna edulis Ker By-product and Its Physicochemical Properties, Carbohydrates Polymers, Vol. 92, No. 1, 2013, pp. 289–296, http:/doi.org/10.1016/j.carbpol.2012.09.067.[7] T. M. H. Nguyen, H. L. Le, T. T. Ha, B. H. Bui, N. T. Le, V. H. Nguyen, T. V. A. Nguyen, Inhibitory Effect on Human Platelet Aggregation and Coagulation and Antioxidant Activity of Canna edulis Ker Gawl Rhizhomes and Its Secondary Metabolites, Journal of Ethnopharmacology, Vol. 263, 2020, pp. 113-136, https:/doi.org/10.1016/j.jep.2020.113136.[8] T. A. Y. Diaa, M. A. Ramada, A. A. Khalifa, Acetophenones, a Chalcone, a Chromone and Flavonoids from Pancratium Maritimum, Phytochemistry, Vol. 49, No. 8, pp. 1998, pp. 2579-2583, http:/doi.org/10.1016/S003109422(98)00429-4. [9] W. Koji, Y. Osanai, T. Imaizumi, S. Kanno, M. Takeshita, M. Ishikawa, Inhibitory Effect of The Alkyl Side Chain of Caffeic Acid Analogues on Lipopolysaccharide-induced Nitric Oxide Production in RAW264.7 Macrophages, Bioorganic Med. Chem., Vol. 16, No. 16, 2008, pp. 7795–7803, https:/doi.org/10.1016/j.bmc.2008.07.006.[10] C. Y. Wang, L. Han, K. Kang, C. L. Shao, Y. X. Wei, C. J. Zheng, H. S Guan, Secondary Metabolites From Green Algae Ulva Pertusa, Chemistry of Natural Compounds Vol. 46, No. 5, 2010, pp. 828-830.[11] C. T. Inh, N. T. H. Van, P. M. Quan, T. T. Q. Trang, T. A. Vien, N. T. Thuy, D. T. Thao, New Diterpenoid Isolated from Medicinal Plant Euphorbia tithymaloides (P.), Vietnam J. Chem., Vol. 54, 2016, pp. 274-279, https:/doi.org/10.15625/0866-7144.2016-00304 (in Vietnamese).[12] Q. Y. Li, H. Liang, B. Wang, Z. Z. Zhao, Chemical Constituents of Momordica charantia L, Yao Xue Xue Bao, Vol. 44, No. 9, 2009, pp. 1014-1018.[13] V. T. Diep, L. T. Loan, N. T. Thu, T. T. Ha, N. M. Khoi, N. H. Tuan, D. T. Ha, Triterpen, Flavonoid and Pyrimidine Compounds from The Aerial Parts of Dregea volubilis, Journal of Medicinal Materials, Vol. 24, No. 6, 2019, pp. 329-332.[14] H. M. Eid, D. Vallerand, A. Muhammad, T. Durst, P. S. Haddad, L. C. Martineau, Structural Constraints and the Importance of Lipophilicity for the Mitochondrial Uncoupling Activity of Naturally Occurring Caffeic Acid Esters with Potential for the Treatment of Insulin Resistance, Biochemical Pharmacology, Vol. 79, No. 3, 2010, pp. 444–454, https:/doi.org/10.1016/j.bcp.2009.08.026.[15] K. Takahashi, Y. Yoshioka, E. Kato, S. Katsuki, O. Iida, K. Hosokawa, J. Kawabata, Methyl Caffeate as a Glucosidase Inhibitor from Solanum Torvum fruits and the Activity of Related Compounds, Bioscience, Biotechnology and Biochemistry, Vol. 74, No. 4, 2010, pp. 741–745, https:/doi.org/10.1271/bbb.9087.[16] S. M. Fiuza, C. Gomes, L. J. Teixeira, M. T. G. D. Cruz, M. N. Cordeiro, N. Milhazes, F. Borges, M. P. Marques, Phenolic Acid Derivatives with Potential Anticancer Properties, a Structure-Activity Relationship Study Part 1: Methyl, Propyl and Octyl Esters of Caffeic and Gallic Acids, Bioorgan Med Chem, Vol. 12, No. 13, 2004, pp. 3581-3589, https:/doi.org/10.1016/j.bmc.2004.04.026.[17] S. P. Lee, G. Jun, E. Yoon, S. Park, C. Yang, Inhibitory Effect of Methyl Caffeate on Fos-Jun-DNA Complex Formation and Suppression of Cancer Cell Growth, Bulletin of Korean Chemical Society, Vol. 22, No. 10, 2001, pp. 1131-1135.        

Additions of caffeic acid, ascorbyl palmitate or γ-tocopherol to fish oil-enriched energy bars affect lipid oxidation differently

2009 ◽  
Vol 112 (2) ◽  
pp. 412-420 ◽  
Author(s):  
Anna Frisenfeldt Horn ◽  
Nina Skall Nielsen ◽  
Charlotte Jacobsen
Keyword(s):  
Fish Oil ◽  
Lipid Oxidation ◽  
Caffeic Acid ◽  
Ascorbyl Palmitate

scholarly journals A novel nanoparticle loaded with methyl caffeate and caffeic acid phenethyl ester against Ralstonia solanacearum—a plant pathogenic bacteria

RSC Advances ◽  
2020 ◽  
Vol 10 (7) ◽  
pp. 3978-3990 ◽  
Author(s):  
Jin-Zheng Wang ◽  
Cheng-Hai Yan ◽  
Xiao-Rui Zhang ◽  
Qing-Bo Tu ◽  
Yan Xu ◽  
...  
Keyword(s):  
Caffeic Acid ◽  
Ralstonia Solanacearum ◽  
Pathogenic Bacteria ◽  
Interaction Model ◽  
Caffeic Acid Phenethyl Ester ◽  
Plant Pathogenic Bacteria ◽  
Methyl Caffeate ◽  
Chemical Pesticides ◽  
Novel Agent

Developing a novel agent and understanding an interaction model between multipolymer nanoparticles and bacteria could be worthwhile to induce the protection of crops with the prevalence of frequent hazards because of the use of chemical pesticides.

Sign in / Sign up

Export Citation Format

Share Document