Effect of Extraction Methods on the Active Compounds and Antioxidant Properties of Ethanolic Extracts of Echinacea purpurea Flower

Read  full  paper  at:

http://www.scirp.org/journal/PaperInformation.aspx?PaperID=53389#.VMBtrSzQrzE

ABSTRACT

The extraction yields, active compounds and antioxidant properties of 50%-aqueous-ethanolic extracts of freeze-dried Echinacea purpurea flower with multi-steps and multi-batches extraction methods were assessed. In multi-steps extraction, the extraction yields of 1st, 2nd, and 3rd extracts were 21.52%, 9.33%, and 2.90%, and their total phenols contents were 182.08, 176.33, and 177.08 mg CAE/g, respectively, with cichoric acid (62.07 – 66.57 mg/g) being the main phenolic compound. No differences in the contents of individual and total caffeic acids derivates existed among 1st, 2nd, and 3rd extracts. The dodeca-2E, 4E, 8Z, 10(E/Z)-tetraenoic acid isobutylamide (alkamide 8/9) contents of 1st, 2nd, and 3rd extracts were 505.38, 598.61, and 585.99 µg/g, respectively. In multi-batches extraction, the extracted dry weight increased with increasing the sample batches, with the extraction yields and alkamide 8/9 contents of samples decreased from 19.93% to 12.98% and 534.36 to 269.76 µg/g, respectively. The total phenol (177.25 – 186.92 mg CAE/g), individual and total caffeic acid derivatives (85.99 – 95.06 mg/g) contents of extracts among different sample batches were not significantly different, with cichoric acid (63.66 – 70.31 mg/g) being the main phenolic compound. All the prepared extracts also exhibited potent antioxidant properties. Overall, the two-step sequential extraction is desirable for extracting bioactive compounds from freeze-dried E. purpurea flower.

Cite this paper

Chen, Y. , Sung, J. and Lin, S. (2015) Effect of Extraction Methods on the Active Compounds and Antioxidant Properties of Ethanolic Extracts of Echinacea purpurea Flower. American Journal of Plant Sciences, 6, 201-212. doi: 10.4236/ajps.2015.61023.

References

[1] Barnes, J., Anderson, L.A., Gibbons, S. and Phillipson, J. D. (2005) Echinacea species (Echinacea angustifolia (DC.) Hell., Echinacea pallida (Nutt.) Nutt., Echinacea purpurea (L.) Moench): A Review of Their Chemistry, Pharmacology and Clinical Properties. Journal of Pharmacy and Pharmacology, 57, 929-954. http://dx.doi.org/10.1211/0022357056127
[2] Bauer, R. and Wagner, H. (1991) Echinacea Species as Potential Immunostimulating Drugs. In: Wagner, H. and Farnsworth, N.R., Eds., Economic and Medicinal Plant Research, Vol. 5, Academic Press, New York, 253-321.
[3] Pellati, F., Benvenuti, S., Magro, L., Melegari, M. and Soragni, F. (2004) Analysis of Phenolic Compounds and Radical Scavenging Activity of Echinacea spp. Journal of Pharmaceutical and Biomedical Analysis, 35, 289-301. http://dx.doi.org/10.1016/S0731-7085(03)00645-9
[4] Tsai, Y.L., Chiu, C.C., Chen, J.Y.F., Chan, K.C. and Lin, S.D. (2012) Cytotoxic Effects of Echinacea purpurea Flower Extracts and Cichoric Acid on Human Colon Cancer Cells through Induction of Apoptosis. Journal of Ethnopharmacology, 143, 914-919.
[5] Gertsch, J., Schoop, R., Kuenzle, U. and Suter, A. (2004) Echinacea Alkylamides Modulate TNF-α Gene Expression via Cannabinoid Receptor CB2 and Multiple Signal Transduction Pathways. FEBS Letters, 577, 563-569. http://dx.doi.org/10.1016/j.febslet.2004.10.064
[6] Raduner, S., Majewska, A., Chen, J.Z., Xie, X.Q., Hamon, J., Faller, B., Altmann, K.H. and Gertsch, J. (2006) Alkylamides from Echinacea Are a New Class of Cannabinomimetics. The Journal of Biological Chemistry, 281, 14192-14206. http://dx.doi.org/10.1074/jbc.M601074200
[7] Wagner, H. (1989) Search for New Plant Constituents with Potential Antiphlogistic and Antiallergic Activity. Planta Medica, 55, 235-241. http://dx.doi.org/10.1055/s-2006-961992
[8] Woelkart, K., Marth, E., Suter, A., Schoop, R., Raggam, R.B., Koidl, C., Kleinhappl, B. and Bauer, R. (2006) Bioavailability and Pharmacokinetics of Echinacea purpurea Preparations and Their Interaction with the Immune System. International Journal of clinical Pharmacology and Therapeutics, 44, 401-408.
http://dx.doi.org/10.5414/CPP44401
[9] Thygesen, L., Thulinn, J., Mortensen, A., Skibsted, L.H. and Molgaard, P. (2007) Antioxidant Activity of Cichoric Acid and Alkamides from Echinacea purpurea, Alone and in Combination. Food Chemistry, 101, 74-81. http://dx.doi.org/10.1016/j.foodchem.2005.11.048
[10] Wang, L. and Weller, C.L. (2006) Recent Advances in Extraction of Nutraceuticals from Plants. Trends in Food Science and Technology, 17, 300-312. http://dx.doi.org/10.1016/j.tifs.2005.12.004
[11] Wu, C.H., Murthy, H.N., Hahn, E.J., Lee, H.L. and Paek, K.Y. (2008) Efficient Extraction of Caffeic Acid Derivatives from Adventitious Roots of Echinacea purpurea. Czech Journal of Food Sciences, 26, 254-258.
[12] Lin, S.D., Sung, J.M. and Chen, C.L. (2011) Effect of Drying and Storage Conditions on Caffeic Acid Derivatives and total Phenolics of Echinacea purpurea Grown in Taiwan. Food Chemistry, 125, 226-231. http://dx.doi.org/10.1016/j.foodchem.2010.09.006
[13] Tsai, Y.L., Chiou, S.Y., Chan, K.C., Sung, J.M. and Lin, S.D. (2012) Caffeic Acid Derivatives, Total Phenols, Antioxidant and Antimutagenic Activities of Echinacea purpurea Flower Extracts. LWT-Food Science and Technology, 46, 169-176. http://dx.doi.org/10.1016/j.lwt.2011.09.026
[14] Goli, A.H., Barzegar, M. and Sahari, M.A. (2004) Antioxidant Activity and Total Phenolic Compounds of Pistachio (Pistachia vera) Hull Extracts. Food Chemistry, 92, 521-525.
http://dx.doi.org/10.1016/j.foodchem.2004.08.020
[15] Hu, C. and Kitts, D.D. (2000) Studies on the Antioxidant of Echinacea Root Extract. Journal of Agricultural and Food Chemistry, 48, 1466-1472. http://dx.doi.org/10.1021/jf990677+
[16] Perry, N.B., Klink, J.W.V., Burgess, E.J. and Parmenter, G.A. (1997) Alkamide Levels in Echinacea purpurea: A Rapid Analytical Method Revealing Differences among Roots, Rhizomes, Stems, Leaves and Flowers. Planta Medica, 63, 58-62. http://dx.doi.org/10.1055/s-2006-957605
[17] Bergeron, C., Livesey, J.F., Awang, D.V.C., Arnason, J.T., Rana, J., Baum, B.R. and Letchamo, W. (2000) A Quantitative HPLC Method for the Quality Assurance of Echinacea Products on the North American Market. Phytochemical Analysis, 11, 207-215.
http://dx.doi.org/10.1002/1099-1565(200007/08)11:4<207::AID-PCA519>3.0.CO;2-T
[18] Shimada, K., Fujikawa, K., Yahara, K. and Nakamura, T. (1992) Antioxidative Properties of Xanthan on the Autoxidation of Soybean Oil in Cyclodextrin Emulsion. Journal of Agricultural and Food Chemistry, 40, 945-948. http://dx.doi.org/10.1021/jf00018a005
[19] Oyaizu, M. (1986) Studies on Products of Browning Reactions: Antioxidative Activities of Products of Browning Reaction Prepared from Glucosamine. Japanese Journal of Nutrition and Dietetics, 44, 307-315. http://dx.doi.org/10.5264/eiyogakuzashi.44.307
[20] Dinis, T.C.P., Madeira, V.M.C. and Almeida, L.M. (1994) Action of Phenolic Derivatives (Acetaminophen, Salicylate, and 5-Aminosalicylate) as Inhibitors of Membrane Lipid Peroxidation and as Peroxyl Radical Scavengers. Archives of Biochemistry and Biophysics, 315, 161-169.
http://dx.doi.org/10.1006/abbi.1994.1485
[21] Hou, C.C., Chen, C.H., Yang, N.S., Chen, Y.P., Lo, C.P., Wang, S.Y., Tien, Y.J., Tsai, P.W. and Shyur, L.F. (2010) Comparative Metabolomics Approach Coupled with Cell- and Gene-Based Assays for Species Classification and Anti-Inflammatory Bioactivity Validation of Echinacea Plants. Journal of Nutritional Biochemistry, 21, 1045-1059. http://dx.doi.org/10.1016/j.jnutbio.2009.08.010
[22] Ebrahimzadeh, M.A., Pourmorad, F. and Bekhradnia, A.R. (2008) Iron Chelating Activity, Phenol and Flavonoid Content of Some Medicinal Plants from Iran. African Journal of Biotechnology, 7, 3188-3192.
[23] Yamauchi, R., Tatsumi, Y., Asano, M., Kato, K. and Ueno, Y. (1988) Effect of Metal Salts Fructose on the Autoxidation of Methyl Linoleate in Emulsions. Agricultural and Biological Chemistry, 52, 849-850. http://dx.doi.org/10.1271/bbb1961.52.849
[24] Shahidi, F., Janitha, P.K. and Wanasundara, P.D. (1992) Phenolic Antioxidants. Critical Reviews in Food Science and Nutrition, 32, 67-103. http://dx.doi.org/10.1080/10408399209527581                       eww150122lx
Advertisements

Phenolic Acids from Parthenium hysterophorus: Evaluation of Bioconversion Potential as Free Radical Scavengers and Anticancer Agents

Read  full  paper  at:

http://www.scirp.org/journal/PaperInformation.aspx?PaperID=53115#.VLXKmcnQrzE

ABSTRACT

Parthenium hysterophorus is a globally recognized invasive alien weed that prominently colonizes grazing areas and cultivated lands causing adverse effect on crop production. Major allelochemicals released from parthenium include sesqueterpene lactones and phenolic acids. Among these the presence of caffeic, vanillic and ferulic acids is of industrial significance as they possess potent free radical scavenging and anticancer activities. This study reports for the first time, high total phenolic acid content (20.82 ± 0.82 mg GAE/g dry sample) in parthenium. The GC-MS analysis indicated the presence of ferulic, p-coumaric, vanillic and gallic acid as major phenolic components. Free radical scavenging activity of the phenolic acids extract gave an EC50 value 130.4 μg/ml when measured using DPPH assay. Anticancer activity of parthenium phenolic extract against A-498 (IC50 0.5237 μg/ml) and MDA-MB231 (IC50 and 0.2685 μg/ml) cancerous cell lines indicated its potential to be used as anticancer agent.

Cite this paper

Panwar, R. , Kumar Sharma, A. , Dutt, D. and Pruthi, V. (2015) Phenolic Acids from Parthenium hysterophorus: Evaluation of Bioconversion Potential as Free Radical Scavengers and Anticancer Agents. Advances in Bioscience and Biotechnology, 6, 11-17. doi: 10.4236/abb.2015.61002.

References

[1] Ghosh, S., Haldar, S., Ganguly, A. and Chatterjee P.K. (2013) Review on Parthenium Hysterphorus as a Potential Energy Source. Renewable and Sustainable Energy Reviews, 20, 420-429.
http://dx.doi.org/10.1016/j.rser.2012.12.011
[2] Swaminathan, C., Vinaya, R.R.S. and Sureshi, KK. (1990) Allelopathic Effects of Parthenium hyterophorus L. on Germination and Seedling Growth of a Few Multipurpose Tress and Arable Crops. International Tree Crops Journal, 6, 143-150.
http://dx.doi.org/10.1080/01435698.1990.9752880
[3] Durre, S. and Muhammad, A.R. (2012) Antioxidant Potential of Phenolic Extracts of Mimusops elengi. Asian Pacific Journal of Tropical Biomedicine, 2, 547-550.
http://dx.doi.org/10.1016/S2221-1691(12)60094-X
[4] Parr, A.J. and Bolwell, G.P. (2000) Phenols in the Plant and in Man. The Potential for Possible Nutritional Enhancement of the Diet by Modifying the Phenols Content or Profile. Journal of the Science of Food and Agriculture, 80, 985-1012.
http://dx.doi.org/10.1002/(SICI)1097-0010(20000515)80:7<985::AID-JSFA572>3.0.CO;2-7
[5] Ryan, D., Robards, K., Prenzler, P. and Antolovich, M. (1999) Applications of Mass Spectrometry to Plant Phenols. TRAC-Trends in Analytical Chemistry, 18, 362-372.
http://dx.doi.org/10.1016/S0165-9936(98)00118-6
[6] Luana, D.R., Mariana, C.M. and Anderson J.T. (2012) Anticancer Properties of hydroxycinnamic Acids—A Review. Cancer and Clinical Oncology, 1.
[7] Chandrakala, M.V., Prakash, D., Patil, R.R., Sukumar, J., Maribashetty, V.G., Gururaj, C.S., Shivakumar, C. and Sekharappa, B.M. (2012) Investigation on the Application of Parthenium hysterophorus Extracts as Feed Additives for Young Larvae of Silkworm. Bombyx mori L. Agricultural Science Research Journals, 2, 449-452.
[8] Tilay, A., Bule, M., Kishenkumar, J. and Annapure, U. (2008) Preparation of Ferulic Acid from Agricultural Wastes: Its Improved Extraction and Purification. Journal of Agricultural and Food Chemistry, 56, 7644-7648.
http://dx.doi.org/10.1021/jf801536t
[9] Leonard, V.M., Tungamirai, M. and John, M.B. (2006) Determination of Ferulic Acid and Related Compounds by Thin Layer Chromatography. African Journal of Biotechnology, 5, 1271-1273.
[10] Kumbhare, M.R., Guleha V. and Sivakumar T. (2012) Estimation of Total Phenolic Content, Cytotoxicity and In-Vitro Antioxidant Activity of Stem Bark of Moringa oleifera. Asian Pacific Journal of Tropical Disease, 144-150.
http://dx.doi.org/10.1016/S2222-1808(12)60033-4
[11] Lucio, M. and Roberto, P. (2008) Determination of Phenolic Compounds in Wines by Novel Matrix Solid-Phase Dispersion Extraction and Gas Chromatography/Mass Spectrometry. Journal of Chromatography A, 1185, 23-30.
http://dx.doi.org/10.1016/j.chroma.2008.01.039
[12] Lee, J.S., Kim, G.H. and Lee, H.G. (2010) Characteristics and Antioxidant Activity of Elsholtzia splendens Extract-Loaded Nanoparticles. Journal of Agricultural and Food Chemistry, 58, 3316-3321.
http://dx.doi.org/10.1021/jf904091d
[13] Ammar, S., Michael, H., Pirkko, H. and Kalevi, P. (2002) Inhibition of Cancer Cell Growth by Crude Extract and the Phenolics of Terminalia chebula Retz Fruit. Journal of Ethnopharmacology, 81, 327-336.
http://dx.doi.org/10.1016/S0378-8741(02)00099-5
[14] Marimuthu, S., Adluri, R.S. and Venugopal, P.M. (2007) Ferulic Acid: Therapeutic Potential through Its Antioxidant Property. Journal of Clinical Biochemistry and Nutrition, 40, 92-100.
http://dx.doi.org/10.3164/jcbn.40.92
[15] Jaroslaw, K., Marina, A., Antonia, S. and Butterfield, D.A. (2002) Ferulic Acid Antioxidant Protection against Hydroxyl and Peroxyl Radical Oxidation in Synaptosomal and Neuronal Cell Culture Systems in Vitro: Structure-Activity Studies. Journal of Nutritional Biochemistry, 13, 273-281.
http://dx.doi.org/10.1016/S0955-2863(01)00215-7
[16] Kampa, M., Nifli, A.P., Notas, G. and Castanas, E. (2007) Polyphenols and Cancer Cell Growth. Reviews of Physiology, Biochemistry & Pharmacology, 159, 79-113.
[17] Subburayan, K., Govindhasamy, K., Nagarajan, R.P. and Rajendran, M. (2011) Radiosensitizing Effect of Ferulic Acid on Human Cervical Carcinoma Cells in Vitro. Toxicology in Vitro, 25, 1366-1375.
http://dx.doi.org/10.1016/j.tiv.2011.05.007                                                              eww150114lx

Process for the Synthesis of Ferrate (VI) Alkali Metal Dry

Read  full  paper  at:

http://www.scirp.org/journal/PaperInformation.aspx?PaperID=53023#.VLR-j8nQrzE

ABSTRACT

The iron compounds in the oxidation state (VI) have the specific advantage of being powerful oxidants and bactericides. This feature explains their particular interest in the treatment of water. The aim of this work is to prepare Na2FeO4 stable at ambient in order to optimize the key parameters influencing the performance of the oxidation of iron (II) to iron (VI), as well as to monitor its degradation over time. The synthesis of this phase has been carried out by using the dry reaction Na2O2 with Fe2O3 with a temperature of 700°C for a reaction time of 13 hours with a Na/Fe ratio of 4 to make it possible to simplify the synthesis procedure, to minimize the cost and enhance the production of iron (VI) to meet the growing demand of ferrate (VI) for its interest in water treatment. The obtained phase was characterized by UV spectrophotometer by measuring the optical density at a wavelength of 507 nm.

Cite this paper

Maghraoui, A. , Zerouale, A. and Ijjaali, M. (2015) Process for the Synthesis of Ferrate (VI) Alkali Metal Dry. Advances in Materials Physics and Chemistry, 5, 10-15. doi: 10.4236/ampc.2015.51002.

References

[1] Wagner, W.F., Gump, J.R. and Hurt, E.N. (1952) Factors Affecting Stability of Aqueous Potassium Ferrate (VI) Solutions. Analytical Chemistry, 24, 1497-1498.
http://dx.doi.org/10.1021/ac60069a037
[2] Audette, R.J. and Quail, J.W. (1972) Potassium, Rubidium, Césium, and Barium Ferrates VI: Préparations, Infrared Spectra, and Magnetic Susceptibilities. Inorganic Chemistry, 11, 1904-1908.
http://dx.doi.org/10.1021/ic50114a034
[3] Hoy, G. and Corson, M. (1980) Critical Slowing down of Spin Fluctuations in K2FeO4. Journal of Magnetism and Magnetic Materials, 15, 627.
http://dx.doi.org/10.1016/0304-8853(80)90693-9
[4] Menil, F. (1985) Systematic Trends of the 57Fe Mossbauer Isomer Shifts in (FeOn) and (FeFn) Polyhedra. Evidence of a New Correlation between the Isomer Shift and the Inductive Effect of the Competing Bond T-X (→Fe) (Where X Is O or F and T Any Element with a Formal Positive Charge. Journal of Physics and Chemistry of Solids, 46, 763-789.
http://dx.doi.org/10.1016/0022-3697(85)90001-0
[5] Licht, S., Naschitz, V., Halperin, L., Halperin, N., Lin, L., Chen, J., Ghosh, S. and Liu, B. (2001) Analysis of Ferrate (VI) Compounds and Super-Iron Fe (VI) Battery Cathodes: FTIR, ICP, Titrimetric, XRD, UV/VIS, and Electrochemical Characterization. Journal of Power Sources, 101, 167-176.
http://dx.doi.org/10.1016/S0378-7753(01)00786-8
[6] Licht, S., Tel-Vered, R. and Halperin, L. (2002) Direct Electrochemical Preparation of Solid Fe (VI) Ferrate, and Super-Iron Battery Compounds. Electrochemistry Communications, 4, 933-937.
http://dx.doi.org/10.1016/S1388-2481(02)00493-9
[7] He, W.C., Wang, J.M., Shao, H.B., Zhang, J.Q. and Cao, C.N. (2005) Novel KOH Electrolyte for One-Step Electrochemical Synthesis of High Purity Solid K2FeO4: Comparison with NaOH. Electrochemistry Communications, 7, 607-611.
http://dx.doi.org/10.1016/j.elecom.2005.04.011
[8] Xu, Z.H., Wang, J.M., Shao, H.B., Zheng, T. and Zhang, J.Q. (2007) Preliminary Investigation on the Physicochemical Properties of Calcium Ferrate (VI). Electrochemistry Communications, 9, 371-377.
http://dx.doi.org/10.1016/j.elecom.2006.09.015
[9] Hívesa, J., Benová, M., Bouzek, K., Sitek, J. and Sharma, V.K. (2008) The Cyclic Voltammetric Study of Ferrate (VI) Formation in a Molten Na/K Hydroxide Mixture. Electrochimica Acta, 54, 203-208.
http://dx.doi.org/10.1016/j.electacta.2008.08.009
[10] Wang, Y.L., Ye, S.H., Wang, Y.Y., Cao, J.S. and Wu, F. (2009) Structural and Electrochemical Properties of a K2FeO4 Cathode for Rechargeable Li Ion Batteries. Electrochimica Acta, 54, 4131-4135.
http://dx.doi.org/10.1016/j.electacta.2009.02.053
[11] El Maghraoui, A., Zerouale, A., Ijjaali, M. and Sajieddine, M. (2013) Synthesis and Characterization of Ferrate (VI) Alkali Metal by Electro-chemical Method. Advances in Materials Physics and Chemistry, 3, 83-87.
http://dx.doi.org/10.4236/ampc.2013.31013
[12] Kanari, N., Gaballah, I., Evrard, O. and Neveux, N. (1999) Procède de synthèse par voie solide de ferrates de métaux alcalins ou alcalino-terreux et ferrates ainsi obtenus. Brevet francais, No. 9913389.
[13] Thompson, J.A. (1985) Process for Producing Alkali Metal Ferrates Utilising Hematite and Magnetite. Brevet Américan, No. 4545974.
[14] Martinez-Tamayo, E., Beltran-Porter, A. and Beltran-Porter, D. (1986) Iron Compounds in High Oxidation States: II. Reaction between Na2O2 and FeSO4. Thermochimica Acta, 97, 243-255.
http://dx.doi.org/10.1016/0040-6031(86)87024-1
[15] Kisselev, Y.M., Kopelev, N.S., Zav’yalova, N.A., Perfiliev, Y.D. and Kazin, P.E. (1989) The Preparation of Alkali Métal Ferrates VI. Russian Journal of Inorganic Chemistry, 34, 1250-1253.
[16] Kopelev, N.S., Perfiliev, Y.D. and Kiselev, Y.M. (1992) Mossbauer Study of Soduim Ferrates (IV) and (VI). Journal of Radioanalytical and Nuclear Chemistry Articles, 162, 239-251.
http://dx.doi.org/10.1007/BF02035384
[17] Cici, M. and Cuci, Y. (1997) Production of Some Coagulant Materials from Galvanizing Workshop Waste. Waste Management, 17, 407-410.
[18] Lee, Y.H., Cho, M., Kim, J.Y. and Yoon, J. (2004) Chemistry of Ferrate Fe (VI) in Aqueous Solution and Its Application as a Green Chemical. Journal of Industrial and Engineering Chemistry, 10, 161-171.
[19] Jiang, J.Q. and Lioyd, B. (2002) Progress in the Development and Use of Ferrate VI Salt as an Oxidant and Coagulant for Water and Wastewater Treatment. Water Research, 36, 1397-1408.
http://dx.doi.org/10.1016/S0043-1354(01)00358-X                                                          eww150113lx
[20] Tsapin, A.I., Goldfeld, M.G., Mcdonald, G.D., Nealson, K.H., Moskovitz, B., Solheid, P., Klemner, W., Kelly, S.D. and Orlandini, K.A. (2000) Iron (VI): Hypothetical Candidate for the Martian Oxidant. Icarus, 147, 68-78.

A Structure and Antioxidant Activity Study of Paracetamol and Salicylic Acid

Read  full  paper  at:

http://www.scirp.org/journal/PaperInformation.aspx?PaperID=52874#.VKtJp8nQrzE

ABSTRACT

The paracetamol has more antioxidant properties than the salicylic acid on the several oxidative stress-forced models and one possible mechanism is due to electron or hydrogen transfer by the evaluated hydroxyl radicals. The antioxidant mechanism for the compounds studied here was performed by molecular modeling using quantum chemical calculations at the B3LYP level of theory. Our results show that the paracetamol has more antioxidant properties than the salicylic acid in experimental and theoretical studies. The theoretical mechanism show that the hydrogen transfer is more favorable than the electron transfer. From the study it was concluded that the electron abstraction for paracetamol is more favored than salicylic acid.

Cite this paper

Borges, R. , Barros, T. , Pereira, G. , Batista Jr., J. , Beleza Filho, R. , Veiga, A. , Hamoy, M. , Mello, V. , Silva, A. and Barros, C. (2014) A Structure and Antioxidant Activity Study of Paracetamol and Salicylic Acid. Pharmacology & Pharmacy, 5, 1185-1191. doi: 10.4236/pp.2014.513130.

References

[1] Mitchell, J.R., Jollow, D.J., Potter, W.Z., Davis, D.C., Gillette, J.R. and Brodie, B.B. (1973) Acetaminophen-Induced Hepatic Necrosis. I. Role of Drug Metabolism. Journal of Pharmacology and Experimental Therapeutics, 187, 185-194.
[2] Stanley, P. and Hegedus, R. (2000) Aspirin—The First Hundred Years. Biologist, 47, 269-271.
[3] Marcus, A.J. (1995) Aspirin as Prophylaxis against Colorectal Cancer. The New England Journal of Medicine, 333, 656-658.
http://dx.doi.org/10.1056/NEJM199509073331011
[4] Herbert, P.R. and Hennekens, C.H. (2000) An Overview of the 4 Randomized Trials of Aspirin Therapy in the Primary Prevention of Vascular Disease. Archives of Internal Medicine, 160, 3123-3127.
http://dx.doi.org/10.1001/archinte.160.20.3123
[5] Lowe, G.D.O. (2001) Who Should Take Aspirin for Primary Prophylaxis of Coronary Heart Disease? Heart, 85, 245-246.
http://dx.doi.org/10.1136/heart.85.3.245
[6] Gasche, C. (2004) Review Article: The Chemoprevention of Colorectal Carcinoma. Alimentary Pharmacology & Therapeutics, 20, 31-35.
http://dx.doi.org/10.1111/j.1365-2036.2004.02045.x
[7] Higgs, G.A., Salmon, J.A., Henderson, B. and Vane, J.R. (1987) Pharmacokinetics of Aspirin and Salicylate in Relation to Inhibition of Arachidonate Cyclooxygenase and Antiinflammatory Activity. Proceedings of the National Academy of Sciences of the United States of America, 84, 1417-1420.
http://dx.doi.org/10.1073/pnas.84.5.1417
[8] Orhan, H. and Sahin, G. (2001) In Vitro Effects of NSAIDS and Paracetamol on Oxidative Stress-Related Parameters of Human Erythrocytes. Experimental and Toxicologic Pathology, 53, 133-140.
http://dx.doi.org/10.1078/0940-2993-00179
[9] Dinis, T.C.P., Madeira, V.M.C. and Almeida, L.M. (1994) Action of Phenolic Derivatives (Acetaminophen, Salicylate and 5-Aminosalicylate) as Inhibitors of Membrane Lipid Peroxidation and as Peroxyl Radical Scavengers. Archives of Biochemistry and Biophysics, 315, 161-169.
http://dx.doi.org/10.1006/abbi.1994.1485
[10] Maharaj, D.S., Saravanan, K.S., Maharaj, H., Mohanakumar, K.P. and Daya, S. (2004) Acetaminophen and Aspirin Inhibit Superoxide Anion Generation and Lipid Peroxidation, and Protect against 1-Methyl-4-phenyl Pyridinium-Induced Dopaminergic Neurotoxicity in Rats. Neurochemistry International, 44, 355-360.
http://dx.doi.org/10.1016/S0197-0186(03)00170-0
[11] Maharaj, H., Maharaj, D.S. and Daya, S. (2006) Acetylsalicylic Acid and Acetaminophen Protect against MPP+-Induced Mitochondrial Damage and Superoxide Anion Generation. Life Sciences, 78, 2438-2443.
http://dx.doi.org/10.1016/j.lfs.2005.10.002
[12] Hall, E.D. (1993) Role of Oxygen Radicals in Central Nervous System Trauma. In: Tarr, M. and Samson, F., Eds., Oxygen Free-Radicals in Tissue Damage, Birkhäuser, Boston, 153-173.
http://dx.doi.org/10.1007/978-1-4615-9840-4
[13] Kasapoglu, M. and Ozben, T. (2001) Alterations of Antioxidant Enzymes and Oxidative Stress Markers in Aging. Experimental Gerontology, 36, 209-220.
http://dx.doi.org/10.1016/S0531-5565(00)00198-4
[14] Sudha, K., Rao, A.V. and Rao, A. (2001) Oxidative Stress and Antioxidants in Epilepsy. Clinica Chimica Acta, 303, 19-24.
http://dx.doi.org/10.1016/S0009-8981(00)00337-5
[15] Halliwell, B. and Gutteridge, J.M.C. (1985) Importance of Free-Radicals and Catalytic Metals in Human Disease. Molecular Aspects of Medicine, 8, 89-193.
http://dx.doi.org/10.1016/0098-2997(85)90001-9
[16] Gutteridge, J.M.C., Quinlan, G.J., Clark, I. and Halliwell, B. (1985) Aluminium Salts Accelerate Peroxidation of Membrane Lipids Stimulated by Iron Salts. Biochimica et Biophysica Acta, 835, 441-447.
http://dx.doi.org/10.1016/0005-2760(85)90113-4
[17] Parr, R.G. and Yang, W. (1989) Density Functional Theory of Atoms and Molecules. Oxford University Press, New York.
[18] Stewart, J.J.P. (1989) Optimization of Parameters for Semi-Empirical Methods I. Method. Journal of Computational Chemistry, 10, 209-220.
http://dx.doi.org/10.1002/jcc.540100208
[19] Becke, A.D. (1993) Density-Functional Thermochemistry. III. The Role of Exact Exchange. The Journal of Chemical Physics, 98, 5648-5652.
http://dx.doi.org/10.1063/1.464913
[20] Lee, C., Yang, W.R. and Parr, G.R. (1988) Development of the Colle Salvetti Correlation-Energy Formula into a Functional of the Electron Density. Physical Review B, 37, 785-789.
http://dx.doi.org/10.1103/PhysRevB.37.785
[21] Hehre, W.J., Radom, L., Schleyer, P.V.R. and Pople, J.A. (1986) Ab Initio Molecular Orbital Theory. John Wiley and Sons, New York.
[22] Prescott, L.F. (1983) Paracetamol Overdosage. Drugs, 25, 290-314.
http://dx.doi.org/10.2165/00003495-198325030-00002
[23] Alves, C.N., Borges, R.S. and Da Silva, A.B.F. (2006) Density Functional Theory Study of Metabolic Derivatives of the Oxidation of Paracetamol. International Journal of Quantum Chemistry, 106, 2617-2623.
http://dx.doi.org/10.1002/qua.20992
[24] Suhail, M. and Ahmad, I. (1995) In Vivo Effects of Acetaminophen on Rat RBC and Role of Vitamin E. Indian Journal of Experimental Biology, 33, 269-271.
[25] Burton, G.W. and Ingold, K.U. (1981) Autoxidation of Biological Molecules. 1. Antioxidant Activity of Vitamin E and Related Chain-Breaking Phenolic Antioxidants in Vitro. Journal of the American Chemical Society, 103, 6472-6477.
http://dx.doi.org/10.1021/ja00411a035
[26] Albano, E., Rundgren, M., Harvison, P.J., Nelson, S.D. and Moldeus, P. (1985) Mechanisms of N-Acetyl-p-benzoquinone Imine Cytotoxicity. Molecular Pharmacology, 28, 306-311.
[27] Courade, J.P., Caussade, F., Martin, K., Besse, D., Delchambre, C., Hanoun, N., Hamon, M., Eschalier, A. and Cloarec, A. (2001) Effects of Acetaminophen on Monoaminergic Systems in the Rat Central Nervous System. Naunyn-Schmiedeberg’s Archives of Pharmacology, 364, 534-537.
http://dx.doi.org/10.1007/s002100100484
[28] Daya, S. and Anoopkumar-Dukie, S. (2000) Acetaminophen In-hibits Liver Tryptophan 2,3-Dioxygenase Activity with a Concomitant Rise in Brain Serotonin Levels and a Reduction in Urinary 5-Hydroxyindole Acetic Acid. Life Sciences, 67, 235-240.
http://dx.doi.org/10.1016/S0024-3205(00)00629-9
[29] Daya, S., Walker, R.B. and Anoopkumar-Dukie, S. (2000) Cyanide-Induced Free-Radical Production and Lipid Peroxidation in Rat Brain Homogenate Is Reduced by Aspirin. Metabolic Brain Disease, 15, 203-210.
http://dx.doi.org/10.1007/BF02674529
[30] Casper, D., Yaparpalvi, U., Rempel, N. and Werner, P. (2000) Ibuprofen Protects Dopaminergic Neurons against Glutamate Toxicity in Vitro. Neuroscience Letters, 289, 201-204.
http://dx.doi.org/10.1016/S0304-3940(00)01294-5
[31] Aubin, N., Curet, O., Deffois, A. and Carter, C. (1998) Aspirin and Salicylate Protect against MPTP-Induced Dopamine Depletion in Mice. Journal of Neurochemistry, 71, 1635-1642.
http://dx.doi.org/10.1046/j.1471-4159.1998.71041635.x
[32] Teismann, P. and Ferger, B. (2001) Inhibition of the Cyclooxygenase Isoenzymes COX-1 and COX-2 Provide Neuroprotection in the MPTP-Mouse Model of Parkinson’s Disease. Synapse, 39, 167-174.
http://dx.doi.org/10.1002/1098-2396(200102)39:2<167::AID-SYN8>3.0.CO;2-U
[33] Mohanakumar, K.P., Muralikrishnan, D. and Thomas, B. (2000) Neuroprotection by Sodium Salicylate against 1-Methyl-4-phenyl-1,2,3,6-tetrahydropyridine-Induced Neurotoxicity. Brain Research, 864, 281-290.
http://dx.doi.org/10.1016/S0006-8993(00)02189-2
[34] Sairam, K., Saravanan, K.S., Banerjee, R. and Mohanakumar, K.P. (2003) Non-Steroidal Anti-Inflammatory Drug Sodium Salicylate, but Not Diclofenac or Celecoxib, Protects against 1-Methyl-4-phenyl Pyridinium-Induced Dopaminergic Neurotoxicity in Rats. Brain Research, 966, 245-252.
http://dx.doi.org/10.1016/S0006-8993(02)04174-4
[35] Queiroz, A.N., Gomes, B.A.Q., Moraes Jr., W.M. and Borges, R.S. (2009) A Theoretical Antioxidant Pharmacophore for Resveratrol. European Journal of Medicinal Chemistry, 44, 1644-1649.
http://dx.doi.org/10.1016/j.ejmech.2008.09.023
[36] Diniz, J.E.M., Borges, R.S. and Alves, C.N. (2004) A DFT Study for Paracetamol and 3,5-Disubstituted Analogues. Journal of Molecular Structure: THEOCHEM, 673, 93-97.
http://dx.doi.org/10.1016/j.theochem.2003.12.002
[37] Freire, A.D.T., Landivar, L.M.C., Queiroz, A.N. and Borges, R.S. (2009) A Theoretical Study for Oxidative Metabolism of Salicylates. Journal of Computational and Theoretical Nanoscience, 6, 1140-1142.
http://dx.doi.org/10.1166/jctn.2009.1157
[38] Silva, J.R., Queiroz, L.M.D., Queiroz, A.N., Souza, P.J.C. and Borges, R.S. (2011) A Theoretical Study of Paracetamol acyl-Ether Derivatives. Journal of Computational and Theoretical Nanoscience, 8, 670-675.
http://dx.doi.org/10.1166/jctn.2011.1738
[39] Borges, R.S., Mendes, A.P.S., Silva, B.H.S., Alves, C.N. and Nascimento, J.L.M. (2011) A Theoretical Study of Salicylate Oxidation for ADME Prediction. Medicinal Chemistry Research, 20, 269-273.
http://dx.doi.org/10.1007/s00044-010-9320-7
[40] Motozaki, W., Nagatani, Y., Kimura, Y., Endo, K., Takemura, T., Kurmaev, E.Z. and Moewes, A. (2011) Evaluation of Antioxidant Activity and Electronic Structure of Aspirin and Paracetamol. Journal of Molecular Structure, 985, 63-69.
http://dx.doi.org/10.1016/j.molstruc.2010.10.021                                                              eww150105lx

Comparative Interactions of Anesthetic Alkylphenols with Lipid Membranes

Read  full  paper  at:

http://www.scirp.org/journal/PaperInformation.aspx?PaperID=52726#.VKIClcCAM4

ABSTRACT

Objective: While substituted phenols have a variety of pharmacological activity, the mechanism underlying their anesthetic effects remains uncertain especially about the critical target. We characterized the lipid membrane-interacting properties of different phenols by comparing with general anesthetic propofol and local anesthetics. Based on the results, we also studied the pharmacological effects possibly associated with their membrane interactivities. Methods: 1,6-Diphenyl-1,3,5-hexatriene-labeled lipid bilayer membranes were prepared with 1,2-dipalmitoyl-phosphatidylcholine as model membranes and with different phospholipids and cholesterol to mimic neuronal membranes. These membrane preparations were treated with phenols and anesthetics at 1 – 200 μM, followed by measuring the fluorescence polarization to determine the membrane interactivities to change membrane fluidity. Antioxidant effects were fluorometrically determined using diphenyl-1-pyrenylphosphine-incorporated liposomes which were treated with 10 – 100 μM phenols, and then peroxidized with 10 μM peroxynitrite. Results: Several phenols interacted with the model membranes and the neuronal mimetic membranes to increase their fluidity at 1 – 10 μM as well as lidocaine and bupivacaine did at 50 – 200 μM. Their comparative potencies were propofol > thymol > isothymol > guaiacol > phenol > eugenol, and bupivacaine > lidocaine, consistent with the rank order of neuro-activity. These phenols inhibited membrane lipid peroxidation at 10 and 100 μM with the potencies correlating to their membrane interactivities. Conclusion: The structure-specific membrane interaction is at least in part responsible for the pharmacology of anesthetic alkylphenols. Membrane-interacting antioxidant alkylphenols may be protective against the peroxynitrite-relating ischemia/reperfusion injury.

Cite this paper

Tsuchiya, H. and Mizogami, M. (2014) Comparative Interactions of Anesthetic Alkylphenols with Lipid Membranes. Open Journal of Anesthesiology, 4, 308-317. doi: 10.4236/ojanes.2014.412044.

References

[1] Guenette, S.A., Beaudry, F., Marier, J.F. and Vachon, P. (2006) Pharmacokinetics and Anesthetic Activity of Eugenol in Male Sprague-Dawley Rats. Journal of Veterinary Pharmacology and Therapeutics, 29, 265-270.
http://dx.doi.org/10.1111/j.1365-2885.2006.00740.x
[2] Park, S.H., Sim, Y.B., Lee, J.K., Kim, S.M., Kang, Y.J., Jung, J.S. and Suh, H.W. (2011) The Analgesic Effects and Mechanisms of Orally Administered Eugenol. Archives of Pharmacal Research, 34, 501-507.
http://dx.doi.org/10.1007/s12272-011-0320-z
[3] Mohammadi, B., Haeseler, G., Leuwer, M., Dengler, R., Krampfl, K. and Bufler, J. (2001) Structural Requirements of Phenol Derivatives for Direct Activation of Chloride Currents via GABAA Receptors. European Journal of Pharmacology, 421, 85-91.
http://dx.doi.org/10.1016/S0014-2999(01)01033-0
[4] García, D.A., Bujons, J., Vale, C. and Suñol, C. (2006) Allosteric Positive Interaction of Thymol with the GABAA Receptor in Primary Cultures of Mouse Cortical Neurons. Neuropharmacology, 50, 25-35.
http://dx.doi.org/10.1016/j.neuropharm.2005.07.009
[5] Haeseler, G. and Leuwer, M. (2002) Interaction of Phenol Derivatives with Ion Channels. European Journal of Anaesthesiology, 19, 1-8.
http://dx.doi.org/10.1097/00003643-200201000-00001
[6] Kozek-Langenecker, S.A. (2002) The Effects of Drugs Used in Anaesthesia on Platelet Membrane Receptors and on Platelet Function. Current Drug Targets, 3, 247-258.
http://dx.doi.org/10.2174/1389450023347759
[7] Pramod, K., Ansari, S.H. and Ali, J. (2010) Eugenol: A Natural Compounds with Versatile Pharmacological Actions. Natural Product Communications, 5, 1999-2006.
[8] Riella, K.R., Marinho, R.R., Santos, J.S., Pereira-Filho, R.N., Cardoso, J.C., Albuquerque-Junior, R.L. and Thomazzi, S.M. (2012) Anti-Inflammatory and Cicatrizing Activities of Thymol, a Monoterpene of the Essential Oil from Lippia gracilis, in Rodents. Journal of Ethnopharmacology, 143, 656-663.
http://dx.doi.org/10.1016/j.jep.2012.07.028
[9] Bocchinfuso, G., Bobone, S., Mazzuca, C., Palleschi, A. and Stella, L. (2011) Fluorescence Spectroscopy and Molecular Dynamics Simulations in Studies on the Mechanism of Membrane Destabilization by Antimicrobial Peptides. Cellular and Molecular Life Sciences, 68, 2281-2301.
http://dx.doi.org/10.1007/s00018-011-0719-1
[10] Lichtenberger, L.M., Zhou, Y., Jayaraman, V., Doyen, J.R., O’Neil, R.G., Dial, E.J., Volk, D.E., Gorenstein, D.G., Boggara, M.B. and Krishnamoorti, R. (2012) Insight into NSAID-Induced Membrane Alterations, Pathogenesis and Therapeutics: Characterization of Interaction of NSAIDs with Phosphatidylcholine. Biochimica et Biophysica Acta, 1821, 994-1002.
[11] Sheu, J.R., Hsiao, G., Luk, H.N., Chen, Y.W., Chen, T.L., Lee, L.W., Lin, C.H. and Chou, D.S. (2002) Mechanisms Involved in the Antiplatelet Activity of Midazolam in Human Platelets. Anesthesiology, 96, 651-658.
http://dx.doi.org/10.1097/00000542-200203000-00022
[12] Kazanci, N. and Severcan, F. (2007) Concentration Dependent Different Action of Tamoxifen on Membrane Fluidity. Bioscience Reports, 27, 247-255.
http://dx.doi.org/10.1007/s10540-007-9050-3
[13] Tsuchiya, H. (2010) Structure-Dependent Membrane Interaction of Flavonoids Associated with Their Bioactivity. Food Chemistry, 120, 1089-1096.
http://dx.doi.org/10.1016/j.foodchem.2009.11.057
[14] Kopec, W., Telenius, J. and Khandelia, H. (2013) Molecular Dynamics Simulations of the Interactions of Medicinal Plant Extracts and Drugs with Lipid Bilayer Membranes. FEBS Journal, 280, 2785-2805.
http://dx.doi.org/10.1111/febs.12286
[15] Sugimoto, M., Uchida, I., Fukami, S., Takenoshita, M., Mashimo, T. and Yoshiya, I. (2000) The α and γ Subunit-Dependent Effects of Local Anesthetics on Recombinant GABAA Receptors. European Journal of Pharmacology, 401, 329-337.
http://dx.doi.org/10.1016/S0014-2999(00)00463-5
[16] Haeseler, G., Maue, D., Grosskreutz, J., Bufler, J., Nentwig, B., Piepenbrock, S., Dengler, R. and Leuwer, M. (2002) Voltage-Dependent Block of Neuronal and Skeletal Muscle Sodium Channels by Thymol and Menthol. European Journal of Anaesthesiology, 19, 571-579.
http://dx.doi.org/10.1017/S0265021502000923
[17] Park, C.K., Kim, K., Jung, S.J., Kim, M.J., Ahn, D.K., Hong, S.D., Kim, J.S. and Oh, S.B. (2009) Molecular Mechanism for Local Anesthetic Action of Eugenol in the Rat Trigeminal System. Pain, 144, 84-94.
http://dx.doi.org/10.1016/j.pain.2009.03.016
[18] Lundbæk, J.A. (2006) Regulation of Membrane Protein Function by Lipid Bilayer Elasticity: A Single Molecule Technology to Measure the Bilayer Properties Experienced by an Embedded Protein. Journal of Physics: Condensed Matter, 18, S1305-S1344.
http://dx.doi.org/10.1088/0953-8984/18/28/S13
[19] Søgaard, R., Werge, T.M., Bertelsen, C., Lundbye, C., Madsen, K.L., Nielsen, C.H. and Lundbæk, J.A. (2006) GABAA Receptor Function Is Regulated by Lipid Bilayer Elasticity. Biochemistry, 45, 13118-13129.
http://dx.doi.org/10.1021/bi060734
[20] Tsuchiya, H. and Mizogami, M. (2013) Characteristic Interactivity of Landiolol, an Ultra-Short-Acting Highly Selective β1-Blocker, with Biomimetic Membranes: Comparisons with β1-Selective Esmolol and Non-Selective Propranolol and Alprenolol. Frontiers in Pharmacology, 4, 150.
http://dx.doi.org/10.3389/fphar.2013.00150
[21] Tsuchiya, H., Ueno, T., Tanaka, T., Matsuura, N. and Mizogami, M. (2010) Comparative Study on Determination of Antioxidant and Membrane Activities of Propofol and Its Related Compounds. European Journal of Pharmaceutical Sciences, 39, 97-102.
http://dx.doi.org/10.1016/j.ejps.2009.11.001
[22] Hendrich, A.B., Malon, R., Pola, A., Shirataki, Y., Motohashi, N. and Michalak, K. (2002) Differential Interaction of Sophora Isoflavonoids with Lipid Bilayers. European Journal of Pharmaceutical Sciences, 16, 201-208.
http://dx.doi.org/10.1016/S0928-0987(02)00106-9
[23] Mainali, L., Feix, J.B., Hyde, J.S. and Subczynski, W.K. (2011) Membrane Fluidity Profiles as Deduced by Saturation-Recovery EPR Measurements of Spin-Lattice Relaxation Times of Spin Labels. Journal of Magnetic Resonance, 212, 418-425.
http://dx.doi.d\org/10.1016/j.jmr.2011.07.022
[24] Popitz-Bergez, F.A., Leeson, S., Strichartz, G.R. and Thalhammer, J.G. (1995) Relation between Functional Deficit and Intraneural Local Anesthetic during Peripheral Nerve Block. A Study in the Rat Sciatic Nerve. Anesthesiology, 83, 583-592.
http://dx.doi.org/10.1097/00000542-199509000-00018
[25] Huang, J.H., Thalhammer, J.G., Raymond, S.A. and Strichartz, G.R. (1997) Susceptibility to Lidocaine of Impulses in Different Somatosensory Afferent Fibers of Rat Sciatic Nerve. Journal of Pharmacology and Experimental Therapeutics, 282, 802-811.
[26] Sinnott, C.J., Cogswell 3rd, L.P., Johnson, A. and Strichartz, G.R. (2003) On the Mechanism by Which Epinephrine Potentiates Lidocaine’s Peripheral Nerve Block. Anesthesiology, 98, 181-188.
http://dx.doi.org/10.1097/00000542-200301000-00028
[27] Marín, L.D., Sánchez-Borzone, M. and García, D.A. (2011) Comparative Antioxidant Properties of Some Gabaergic Phenols and Related Compounds, Determined for Homogeneous and Membrane Systems. Medicinal Chemistry, 7, 317-324.
http://dx.doi.org/10.2174/157340611796150969
[28] Tsuchiya, H. (2001) Structure-Specific Membrane-Fluidizing Effect of Propofol. Clinical and Experimental Pharmacology and Physiology, 28, 292-299.
http://dx.doi.org/10.1046/j.1440-1681.2001.03441.x
[29] Hikiji, W., Kudo, K., Usumoto, Y., Tsuji, A. and Ikeda, N. (2010) A Simple and Sensitive Method for the Determination of Propofol in Human Solid Tissues by Gas Chromatography-Mass Spectrometry. Journal of Analytical Toxicology, 34, 389-393.
http://dx.doi.org/10.1093/jat/34.7.389
[30] Bahri, M.A., Seret, A., Hans, P., Piette, J., Deby-Dupont, G. and Hoebeke, M. (2007) Does Propofol Alter Membrane Fluidity at Clinically Relevant Concentrations? An ESR Spin Label Study. Biophysical Chemistry, 129, 82-91.
http://dx.doi.org/10.1016/j.bpc.2007.05.011
[31] Sánchez, M.E., Turina, A.V., Garcia, D.A., Nolan, M.V. and Perillo, M.A. (2004) Surface Activity of Thymol: Implications for an Eventual Pharmacological Activity. Colloids and Surfaces B: Biointerfaces, 34, 77-86.
http://dx.doi.org/10.1016/j.colsurfb.2003.11.007
[32] Reiner, G.N., Fraceto, L.F., de Paula, E., Perillo, M.A. and García, D.A. (2013) Effects of Gabaergic Phenols on Phospholipid Bilayers as Evaluated by 1H-NMR. Journal of Biomaterials and Nanotechnology, 4, 28-34.
http://dx.doi.org/10.4236/jbnb.2013.43A004
[33] Hume, W.R. (1984) An Analysis of the Release and the Diffusion through Dentin of Eugenol from Zinc Oxide-Eugenol Mixtures. Journal of Dental Research, 63, 881-884.
http://dx.doi.org/10.1177/00220345840630061301
[34] Hashimoto, S., Uchiyama, K., Maeda, M., Ishitsuka, K., Furumoto, K. and Nakamura, Y. (1988) In Vivo and in Vitro Effects of Zinc Oxide-Eugenol (ZOE) on Biosynthesis of Cyclooxygenase Products in Rat Dental Pulp. Journal of Dental Research, 67, 1092-1096.
http://dx.doi.org/10.1177/00220345880670080601
[35] Markowitz, K., Moynihan, M., Liu, M. and Kim, S. (1992) Biologic Properties of Eugenol and Zinc Oxide-Eugenol: A Clinically Oriented Review. Oral Surgery, Oral Medicine, Oral Pathology, 73, 729-737.
http://dx.doi.org/10.1016/0030-4220(92)90020-Q
[36] Ross, S. and Foëx, P. (1999) Protective Effects of Anaesthetics in Reversible and Irreversible Ischaemia-Reperfusion Injury. British Journal of Anaesthesia, 82, 622-632.
http://dx.doi.org/10.1093/bja/82.4.622
[37] Lalu, M.M., Wang, W. and Schulz, R. (2002) Peroxynitrite in Myocardial Ischemia-Reperfusion Injury. Heart Failure Reviews, 7, 359-369.
http://dx.doi.org/10.1023/a:1020766502316
[38] Radi, R. (2013) Peroxynitrite, a Stealthy Biological Oxidant. Journal of Biological Chemistry, 288, 26464-26472.
http://dx.doi.org/10.1074/jbc.R113.472936
[39] Suzuki, Y.J., Tsuchiya, M., Wassall, S.R., Choo, Y.M., Govil, G., Kagan, V.E. and Packer, L. (1993) Structural and Dynamic Membrane Properties of α-Tocopherol and α-Tocotrienol: Implication to the Molecular Mechanism of Their Antioxidant Potency. Biochemistry, 32, 10692-10699.
http://dx.doi.org/10.1021/bi00091a020
[40] Lúcio, M., Ferreira, H., Lima, J.L. and Reis, S. (2007) Use of Liposomes to Evaluate the Role of Membrane Interactions on Antioxidant Activity. Analytica Chimica Acta, 597, 163-170.
http://dx.doi.org/10.1016/j.aca.2007.06.039
[41] Gutiérrez, M.E., García, A.F., Africa de Madariaga, M., Sagrista, M.L., Casadó, F.J. and Mora, M. (2003) Interaction of Tocopherols and Phenolic Compounds with Membrane Lipid Components: Evaluation of Their Antioxidant Activity in a Liposomal Model System. Life Sciences, 72, 2337-2360.
http://dx.doi.org/10.1016/s0024-3205(03)00120-6                                                                   eww141230lx

Synthesis and Biological Activity of Drug Delivery System Based on Chitosan Nanocapsules

Read  full paper at:

http://www.scirp.org/journal/PaperInformation.aspx?PaperID=51285#.VGKvj2fHRK0

ABSTRACT

Chitosan nanocapsules containing naproxen as an active ingredient were synthesized by ionic gelation method in presence of polyanion tripolyphosphate as a crosslinker. The morphology and diameter of the prepared chitosan nanoparticles was characterized using scanning electron microscopy and transition electron microscopy. Different factors affecting on the size diameter of chitosan nanoparticles such as stirring time and temperature, pH values as well as chitosan concentration were studied. Different factors affecting on the immobilization of naproxen into chitosan nanoparticles such as time, temperature and pH values were optimized. Synthesized naproxen/chitosan nanocapsules were assessed against both Gram positive bacterial strain such as Bacillus subtilis and Staphylococcus aureus and Gram negative bacterial strain such as Pseudomonas aeruginosa and Escherichia coli. Also, the antifungal activity of the naproxen/chitosan nanocapsules against Saccharomyces cerevisiae was demonstrated. Super oxide dismutase like activity of naproxen/chitosan nanocapsules will be determined.

Cite this paper

Gouda, M. , Elayaan, U. and Youssef, M. (2014) Synthesis and Biological Activity of Drug Delivery System Based on Chitosan Nanocapsules. Advances in Nanoparticles, 3, 148-158. doi: 10.4236/anp.2014.34019.

References

[1] Juang, R.S., Wu, F.C. and Tseng, R.L. (2001) Solute Adsorption and Enzyme Immobilizationon Chitosan Beads Prepared from Shrimp Shell Wastes. Bioresource Technology, 80, 187-193.
http://dx.doi.org/10.1016/S0960-8524(01)00090-6
[2] Monteiro, O.A. and Airoldi, C. (1999) Some Studies of Crosslinking Chitosan Glutaraldehyde Interaction of Homogeneous System. International Journal of Biological Macromolecules, 26, 119-128.
http://dx.doi.org/10.1016/S0141-8130(99)00068-9
[3] Denkbas, E.B., Kilicay, E., Birlikseven, C. and Ozturk, E. (2002) Magnetic Chitosan Microspheres: Preparation and Characterization. Reactive and Functional Polymers, 50, 225-232.
http://dx.doi.org/10.1016/S1381-5148(01)00115-8
[4] Selmer-Olsen, E., Ratnaweera, H.C. and Pehrson, R. (1996) Novel Treatment Process for Dairy Wastewater with Chitosan Produced from Shrimp-Shell Waste. Water Science and Technology, 34, 33-40.
http://dx.doi.org/10.1016/S0273-1223(96)00818-9
[5] Kucera, J. (2004) Fungal Myceliumthe Source of Chitosan for Chromatography. Journal of Chromatography B, 808, 69-73.
http://dx.doi.org/10.1016/j.jchromb.2004.05.023
[6] Chiou, S.H. and Wu, W.T. (2004) Immobilization of Candida Rugosa Lipase on Chitosan with Activation of Hydroxyl Group. Biomaterials, 25, 197-204.
http://dx.doi.org/10.1016/S0142-9612(03)00482-4
[7] Mi, F.L., Kuan, C.Y., Shyu, S.S., Lee, S.T. and Chang, S.F. (2000)The Study of Gelation Kinetics and Chain-Relaxation Properties of Glutaraldehyde-Cross-Linked Chitosan Gel and Their Effects on Microspheres Preparation and Drug Release. Carbohydrate Polymers, 41, 389-396.
http://dx.doi.org/10.1016/S0144-8617(99)00104-6
[8] Berthold, A., Cremer, K. and Kreuter, J. (1996) Preparation and Characterization of Chitosan Microspheres as Drug Carrier for Prednisolone Sodium Phosphate as Model for Anti-Inflammatory Drugs. Journal of Controlled Release, 39, 17-25.
http://dx.doi.org/10.1016/0168-3659(95)00129-8
[9] Tian, X.X. and Groves, M.J. (1999) Formulation and Biological Activity of Antineoplastic Proteoglycans Derived from Mycobacterium vaccae in Chitosan Nanoparticles. Journal of Pharmacology and Pharmacotherapeutics, 51, 151-157.
http://dx.doi.org/10.1211/0022357991772268
[10] Du, J., Chen, Y., Han, C. and Schmidt, M. (2003) Organic/Inorganic Hybrid Vesicles Based on a Reactive Block Copolymer. Journal of the American Chemical Society, 125, 14710-14711.
http://dx.doi.org/10.1021/ja0368610
[11] Clark, C.G. and Wooley, K.L. (2001) Dendrimers and Other Dendritic Polymers. In: Tomalia, D.A., Ed., Regioselectively-Crosslinked Nanostructures, Wiley, New York, 166-174.
[12] Peyratout, C.S. and Dahne, L. (2004) Tailor-Made Polyelectrolyte Microcapsules: From Multilayers to Smart Containers. Angewandte Chemie International Edition, 43, 3762-3783.
http://dx.doi.org/10.1002/anie.200300568
[13] Sukhorukov, G.B., Rogach, A.L., Zebli, B., Liedl, T., Skirtach, A.G. and Parak, W.J. (2005) Nanoengineered Polymer Capsules: Tools for Detection, Controlled Delivery, and Site-Specific Manipulation. Small, 1, 194-200.
http://dx.doi.org/10.1002/smll.200400075
[14] Bédard, M.F., De Geest, B.G., Skirtach, A.G., Mohwaldb, H. and Sukhorukov, G.B. (2010) Polymeric Microcapsules with Light Responsive Properties for Encapsulation and Release. Advances in Colloid and Interface Science, 158, 2-14.
http://dx.doi.org/10.1016/j.cis.2009.07.007
[15] Li, X.D., Lu, T., Xu, J.J., Hu, Q.L. and Shen, J.C. (2009) A Study of Properties of “Micelle-Enhanced” Polyelectrolyte Capsules: Structure, Encapsulation and in Vitro Release. Acta Biomaterialia, 5, 2122-2131.
http://dx.doi.org/10.1016/j.actbio.2009.01.045
[16] Li, G., Feng, Y.Q., Gao, P. and Li, X.G. (2008) Preparation of Mono-Dispersed Polyurea-Urea Formaldehyde Double Layered Microcapsules. Polymer Bulletin, 60, 725-731.
http://dx.doi.org/10.1007/s00289-008-0894-x
[17] Zhao, M.W., Zheng, L.Q., Bai, X.T., Li, N. and Yu, L. (2009) Fabrication of Silica Nanoparticles and Hollow Spheres Using Ionic Liquid Microemulsion Droplets as Temdishes. Colloids and Surfaces A: Physicochemical and Engineering Aspects, 346, 229-236.
http://dx.doi.org/10.1016/j.colsurfa.2009.06.021
[18] Zhang, K., Zheng, L.L., Zhang, X.H., Chen, X. and Yang, B. (2006) Silica-PMMA Core-Shell and Hollow Nanospheres. Colloids and Surfaces A: Physicochemical and Engineering Aspects, 277, 145-150.
http://dx.doi.org/10.1016/j.colsurfa.2005.11.049
[19] Liu, H.X., Wang, C.Y., Gao, Q.X., Chen, J.X., Ren, B.Y. and Tong, Z. (2009) Facile Fabrication of Well-Defined Hydrogel Beads with Magnetic Nanocomposite Shells. International Journal of Pharmaceutics, 376, 92-98.
http://dx.doi.org/10.1016/j.ijpharm.2009.04.031
[20] Szarpak, A., Cui, D., Dubreuil, F., De Geest, B.G., De Cock, L.J., Picart, C. and Ly-Velty, R.A. (2010) Designing Hyaluronic Acid-Based Layer-by-Layer Capsules as a Carrier for Intracellular Drug Delivery. Biomacromolecules, 11, 713-720.
http://dx.doi.org/10.1021/bm9012937
[21] Endo, Y., Sato, K. and Anzai, J.I. (2010) Preparation of Avidin-Containing Polyelectrolyte Microcapsules and Their Uptake and Release Properties. Polymer Bulletin, 66, 711-720.
http://dx.doi.org/10.1007/s00289-010-0375-x
[22] Taqieddin, E. and Amiji, M. (2004) Enzyme Immobilization in Novel Alginate-Chitosan Core-Shell Microcapsules. Biomaterials, 25, 1937-1942.
http://dx.doi.org/10.1016/j.biomaterials.2003.08.034
[23] Tang, Y.F., Zhao, Y.Y., Li, Y. and Du, Y.M. (2010) A Thermo-Sensitive Chitosan/Poly(Vinyl Alcohol) Hydrogel Containing Nanoparticles for Drug Delivery. Polymer Bulletin, 64, 791-804.
http://dx.doi.org/10.1007/s00289-009-0214-0
[24] Harrington, P.J. and Lodewijk, E. (1997) Large-Scale Synthetic Process for (S)-Naproxen by Syntex. Organic Process Research Development, 1, 72-76.
http://dx.doi.org/10.1021/op960009e
[25] Rollas, S. and Kucukguzel, S.G. (2007) Biological Activities of Hydrazone Derivatives. Molecules, 12, 1910-1939.
http://dx.doi.org/10.3390/12081910
[26] Sriram, D., Yogeeswari, P. and Devakaram, R.V. (2006) Synthesis, in Vitro and in Vivo Antimycobacterial Activities of Diclofenac Acid Hydrazones and Amides. Bioorganic Medicinal Chemistry, 14, 3113-3118.
http://dx.doi.org/10.1016/j.bmc.2005.12.042
[27] Munoz-Muniz, O. and Juaristi, E. (2003) Enantioselective Protonation of Prochiralenolates in the Asymmetric Synthesis of (S)-Naproxen. Tetrahedron Letters, 44, 2023-2026.
http://dx.doi.org/10.1016/S0040-4039(03)00217-X
[28] Tang, Z.X., Qian, J.Q. and Shi, L.E. (2007) Preparation of Chitosan Nanoparticles as Carrier for Immobilized Enzyme. Applied Biochemistry and Biotechnology, 136, 77-97.
http://dx.doi.org/10.1007/BF02685940
[29] Syedakulsum, Padmalatha, M., Sandeep, K., Saptasila, B. and Vidyasagar, G. (2011) Spectrophotometric Methods for the Determination of Naproxen sodium in Pure and Pharmaceutical Dosage Forms. International Journal of Research in Pharmaceutical and Biomedical Sciences, 2, 1303-1307.
[30] Genthner, F.J., Hook, L.A. and Strohl, W.R. (1985) Determination of the Molecular Mass of Bacterial Genomic DNA and Plasmid Copy Number by High-Pressure Liquid Chromatography. Applied and Environmental Microbiology, 50, 1007-1013.
[31] Sambrook, J., Fritsch, E.F. and Maniatis, T. (1989) Molecular Cloning: A Laboratory Manual. Cold Spring Harbor Laboratory Press, Cold Spring Harbor.
[32] Laemmli, U.K. (1970) Cleavage of Structural Proteins during the Assembly of the Head of Bacteriophage T4. Nature, 227, 680-685.
[33] Bauer, A.W., Kirby, W.M., Sherris, J.C. and Turck, M. (1966) Antibiotic Susceptibility Testing by a Standardized Single Disk Method. Journal of Clinical Pathology, 45, 493-496.
http://dx.doi.org/10.1038/227680a0
[34] Bridges, S.M. and Salin, M.L. (1981) Distribution of Iron Containing Superoxide Dismutase in Vascular Plants. Plant Physiology, 68, 275-278.
http://dx.doi.org/10.1104/pp.68.2.275                                                                                          eww141112lx

Phytoremedial Effect of Pleurotus cornucopiae (Oyster Mushroom) against Sodium Arsenite Induced Toxicity in Charles Foster Rats

Read  full  paper  at:

http://www.scirp.org/journal/PaperInformation.aspx?PaperID=51220#.VFwZhWfHRK0

ABSTRACT

This study was carried out to investigate the therapeutic role of the ethanolic extract of Pleurotus cornucopiae on sodium arsenite induced nephrotoxicity in rats. Sodium arsenite at the dose of 8 mg•kg–1 body weight orally caused renal damage in rats as manifested by the significant rise in serum levels of serum urea, uric acid and creatinine level compared with control. Ethanolic extracts of P. cornucopiae (400 mg•kg–1 body weight per day) was administered orally for 30 days to sodium arsenite pre-treated rats. The results show significant decrease in the serum urea, uric acid and creatinine levels in comparison to the arsenic treated denotes the nephroprotective effect of P. cornucopiae against sodium arsenite induced toxicity. Furthermore, it also possesses antioxidant effect as lipid peroxidation (MDA) levels decreased in P. cornucopiae treated group in comparison to arsenic treated group. Thus, the present study reveals that P. cornucopiae possesses nephroprotective as well as antioxidant property against arsenic induced toxicity.

Cite this paper

Suman, S. , Ali, M. , Kumar, R. and Kumar, A. (2014) Phytoremedial Effect of Pleurotus cornucopiae (Oyster Mushroom) against Sodium Arsenite Induced Toxicity in Charles Foster Rats. Pharmacology & Pharmacy, 5, 1106-1112. doi: 10.4236/pp.2014.512120.

References

[1] Antman, K.H. (2001) Introduction: The History of Arsenic Trioxide in Cancer Therapy. The Oncologist, 6, 1-2.
http://dx.doi.org/10.1634/theoncologist.6-suppl_2-1
[2] Ahamed, S., Sengupta, M.K., Mukherjee, A., Hossain, M.A., Das, B., Nayak, B., Pal, A., Mukherjee, S.C., Pati, S., Dutta, R.N., Chatterjee, G., Mukherjee, A., Srivastava, R. and Chakraborti, D. (2006) Arsenic Groundwater Contamination and Its Health Effects in the State of Uttar Pradesh (UP) in Upper and Middle Ganga Plain, India: A Severe Danger. Science of the Total Environment, 370, 310-322.
http://dx.doi.org/10.1016/j.scitotenv.2006.06.015
[3] Mukherjee, A., Sengupta, M.K. and Hossain, M.A. (2006) Arsenic Contamination in Groundwater: A Global Perspective with Emphasis on the Asian Scenario. Journal of Health, Population, and Nutrition, 24, 142-163.
[4] Karim, M. (2000) Arsenic in Groundwater and Health Problems in Bangladesh. Water Research, 34, 304-310.
http://dx.doi.org/10.1016/S0043-1354(99)00128-1
[5] Vahter, M.E. (2007) Interactions between Arsenic Induced Toxicity and Nutrition in Early Life. Journal of Nutrition, 137, 2798-2804.
[6] Martini, F. (1989) Fundamentals of Anatomy and Physiology. Prentice Hall, Englewood Cliffs, 944.
[7] Saxena, P.N., Mahour, K. and Kumar, A. (2006) Protective Effect of Panax ginseng Extract on Renal Functions Altered by Mercuric Chloride in Albino Rats. Journal of Ginseng Research, 30, 100-105.
http://dx.doi.org/10.5142/JGR.2006.30.3.100
[8] Kumar, A., Suman, S., Kumar, R., Singh, J.K. and Ali, M. (2014) Hepatoprotective Effect of Edible Oyster Mushroom Pleurotus cornucopiae against Sodium Arsenite Induced Hepatotoxicity in Rats. International Journal of Phytomedicine, 6, 275-279.
[9] Van Herck, H., Baumans, V., Brandt, C.J., Hesp, A.P., Sturkenboom, J.H., Van Lith, H.A., Van Tintelen, G. and Beynen, A.C. (1998) Orbital Sinus Blood Sampling in Cats as Performed by Different Animal Technician: The Influence of Technique and Expertise. Laboratory Animals, 32, 377-386.
http://dx.doi.org/10.1258/002367798780599794
[10] Berthelot, M.P.E. (1859) Berthelot’s Reaction Mechanism. Report de Chimie Applique, 2884.
[11] Fawcett, J.K. and Scott, J.E. (1960) A Rapid and Precise Method for the Determination of Urea. Journal of Clinical Pathology, 13, 156-159.
http://dx.doi.org/10.1136/jcp.13.2.156
[12] Bonsnes, R.W. and Taussky, H.H. (1945) On Colorimetric Determination of Creatinine by the Jaffe Reaction. The Journal of Biological Chemistry, 158, 581-591.
[13] Toro, G. and Ackermann, P.G. (1975) Practical Clinical Chemistry. Little Brown and Co., Boston, 154.
[14] Draper, H.H. and Hadley, M. (1990) Malondialdehyde Determination as Index of Lipid Peroxidation. Methods in Enzymology, 186, 421-431.
http://dx.doi.org/10.1016/0076-6879(90)86135-I
[15] Maitani, T., Saito, N., Abe, M., Uchiyama, S. and Saito, Y. (1987). Chemical Form Dependent Induction of Hepatic Zinc-Thionein by Arsenic Administration and Effect of Co-Administered Selenium in Mice. Toxicology Letters, 39, 63-70.
http://dx.doi.org/10.1016/0378-4274(87)90257-8
[16] Peraza, M.A., Fierro, F.A., Barber, D.S., Casarez, E. and Rael, L.T. (1998) Effects of Micronutrients on Metal Toxicity. Environmental Health Perspectives, 106, 203-216.
[17] Choudhary, H., Harvey, T., Thayer, W.C., Lockwood, T.F., Stitelor, W.M., Goodrum, P.E., Hasset, J.M. and Diamond, G.L. (2001) Urinary Cadmium Elimination as a Biomarker of Exposure for Evaluating a Cadmium Dietary Exposure—Biokinetics Model. Journal of Toxicology and Environmental Health, Part A, 63, 221-250.
[18] Hollis, L., Hogstrand, C. and Wood, C.M. (2001) Tissue-Specific Cadmium Accumulation, Metallothionein Induction, and Tissue Zinc and Copper Levels during Chronic Sublethal Cadmium Exposure in Juvenile Rainbow Trout. Archives of Environmental Contamination and Toxicology, 41, 468-474.
http://dx.doi.org/10.1007/s002440010273
[19] Yoon, S., Han, S.S. and Rana, S.V.S. (2008) Molecular Markers of Heavy Metal Toxicity—A New Paradigm for Health Risk Assessment. Journal of Environmental Biology, 29, 1-14.
[20] Flora, S.J.S., Bhadauria, S., Kanan, G.M. and Singh, N. (2007) Arsenic Induced Oxidative Stress and the Role of Antioxidant Supplementation during Chelation: A Review. Journal of Environmental Biology, 28, 333-347.
[21] Farombi, E.O., Adelow, O.A. and Ajimoko, Y.R. (2007) Biomarkers of Oxidative Stress and Heavy Metal Levels as Indicators of Environmental Pollution in African Cat Fish (Clarias gariepinus) from Nigeria Ogunriver. International Journal of Environmental Research and Public Health, 4, 158-165.
http://dx.doi.org/10.3390/ijerph2007040011
[22] Anetor, J.I. (2002) Serum Uric Acid and Standardized Urinary Protein: Reliable Bioindicators of Lead Nephropathy in Nigerian Lead Workers. African Journal of Biomedical Research, 5, 19-24.
[23] Chandra Sekhar, K., Chary, N.S., Kamala, C.T., Venkatesware Rao, J., Balaram, V. and Anjaneya, Y. (2003) Risk Assessment and Pathway Study of Arsenic in Industrially Contaminated Sites of Hyderabad: A Case Study. Environment International, 29, 601-611.
http://dx.doi.org/10.1016/S0160-4120(03)00017-5
[24] Dioka, C.E., Orisakwe, O.E., Adeniyi, F.A. and Meludu, S.C. (2004) Liver and Renal Function Tests in Artisans Occupationally Exposed to Lead in Mechanic Village in Nnewi, Nigeria. International Journal of Environmental Research and Public Health, 1, 21-25.
http://dx.doi.org/10.3390/ijerph2004010021
[25] Kalia, K. and Flora, S.J.S. (2005) Strategies for Safe and Effective Therapeutic Measures for Chronic Arsenic and Lead Poisoning. Journal of Occupational Health, 47, 11-21.
http://dx.doi.org/10.1539/joh.47.1
[26] Hink, H.U., Santanam, N. and Dikalov, S. (2002) Peroxidase Properties of Extracellular Superoxide Dismutase: Role of Uric Acid in Modulating in Vivo Activity. Arteriosclerosis, Thrombosis, and Vascular Biology, 22, 1402-1408.
http://dx.doi.org/10.1161/01.ATV.0000027524.86752.02
[27] Ames, B.N., Cathcart, R., Schwiers, E. and Hochst, P. (1981) Uric Acid Provides an Antioxidant Defence against and Radical Caused Aging and Cancer: A Hypothesis. Proceedings of the National Academy of Sciences of the United States of America, 78, 6858-6862.
http://dx.doi.org/10.1073/pnas.78.11.6858
[28] Aphosian, H.V. (1989) Biochemical Toxicology of Arsenic. In: Hodgson, E., Bend, J.R. and Philpot, R.M., Eds., Reviews in Biochemical Toxicology, Vol. 10, Elsevier Science Publishing Co., New York, 265-299.
[29] Klassen, C.D. (1996) Heavy Metals and Heavy Metal Antagonists. In: Hardman, J.G., Gilman, A.G. and Limbird, L.E., Eds., Goodman and Gilman’s the Pharmacological Basis of Therapeutics, McGraw-Hill, New York, 1649-1672.
[30] Verbeke, M., Van De Voorde, J. and Lameire, N. (1996) Prevention of Experimental Acute Tubular Necrosis: Current Clinical Applications and Perspectives. Advances in Nephrology from the Necker Hospital, 25, 177-216.         eww141107lx