One-pot synthesis, antioxidant activity and toxicity evaluation of some hydroxyxanthones
Електронний науковий архів Науково-технічної бібліотеки Національного університету "Львівська політехніка"
Переглянути архів Інформація| Поле | Співвідношення | |
| Title |
One-pot synthesis, antioxidant activity and toxicity evaluation of some hydroxyxanthones
Одностадійний синтез і оцінка антиокиснювальної активності та токсичності деяких гідроксиксантонів |
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| Creator |
Yuanita, Emmy
Pranowo, Harno Dwi Siswanta, Dwi Swasono, Respati Tri Mustofa Zulkarnain, Abdul Karim Syahri, Jufrizal Jumina |
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| Contributor |
Universitas Mataram, Indonesia
Universitas Gadjah, Mada, Indonesia Universitas Muhammadiyah Riau, Indonesia |
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| Subject |
антиоксидант
гідроксиксантони 2 2- дифеніл-1-пікрилгідразил реагент Ітона antioxidant hydroxyxanthones 2 2-diphenyl- 1-picrylhydrazyl assay Eaton’s reagent |
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| Description |
За допомогою одностадійої реакції цикло- дегідрування похідних гідроксибензенової кислоти (саліцилова або резорцилова кислота) з флороглюціном або пірогалолом у присутності реагенту Ітона (P2O5/MeSO3H) одержано нові сполуки гідроксиксантону. Для визначення інгібуючої концентрації (IC50) синтезованих сполук їх антиокиснювальну активність перевірено за допомогою 2,2-дифеніл-1-пікрилгід- разилу. Цитотоксичність отриманих сполук оцінено MТT- тестом на лінії клітин Vero. Встановлено, що положення та кількість гідроксильних груп можуть суттєво вплинути на потенційну антиокиснювальну активність приготовлених сполук. Показано, що синтезовані сполуки гідроксиксантону можна класифікувати як сильні антиоксиданти та їх можна використовувати в промисловості. Some new hydroxyxanthone compounds were prepared through one pot cyclodehydration reaction of hydroxybenzoic acid derivatives (salicylic acid or resorcylic acid) with phloroglucinol or pyrogallol in the presence of Eaton’s reagent (P2O5/MeSO3H). The synthesized compounds were screened for their antioxidant activities by 2,2-diphenyl-1-picrylhydrazyl (DPPH) methods to determine their inhibitory concentration (IC50). Cytotoxicity of the prepared compounds was also evaluated by MMT assay on Vero cell line. It was observed that the position and the number of hydroxyl groups could significantly affect the potent antioxidant activity of the prepared compounds. Cytotoxicity evaluation of new compounds indicated that the synthesized series of hydroxyl xanthone were categorized as very strong antioxidants and showed potential development as a commercial antioxidant compound. |
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| Date |
2019-06-20T11:19:49Z
2019-06-20T11:19:49Z 2018-01-20 2018-01-20 |
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| Type |
Article
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| Identifier |
One-pot synthesis, antioxidant activity and toxicity evaluation of some hydroxyxanthones / Emmy Yuanita, Harno Dwi Pranowo, Dwi Siswanta, Respati Tri Swasono, Mustofa, Abdul Karim Zulkarnain, Jufrizal Syahri, Jumina // Chemistry & Chemical Technology. — Lviv : Lviv Politechnic Publishing House, 2018. — Vol 12. — No 3. — P. 290–295.
http://ena.lp.edu.ua:8080/handle/ntb/45184 One-pot synthesis, antioxidant activity and toxicity evaluation of some hydroxyxanthones / Emmy Yuanita, Harno Dwi Pranowo, Dwi Siswanta, Respati Tri Swasono, Mustofa, Abdul Karim Zulkarnain, Jufrizal Syahri, Jumina // Chemistry & Chemical Technology. — Lviv : Lviv Politechnic Publishing House, 2018. — Vol 12. — No 3. — P. 290–295. |
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| Language |
en
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| Relation |
Chemistry & Chemical Technology, 3 (12), 2018
https://doi.org/10.3390/molecules15106905 https://doi.org/10.1016/j.ejmech.2011.01.043 https://doi.org/10.1080/87559129.2015.1022832 https://doi.org/10.1016/j.supflu.2009.03.004 https://doi.org/10.1007/BF02901825 https://doi.org/10.1016/j.bmcl.2005.08.099 https://doi.org/10.1021/jf405570u https://doi.org/10.1016/j.bmc.2010.07.044 https://doi.org/10.1021/jo00984a016 https://doi.org/10.1039/p19730001329 https://doi.org/10.1021/jo00324a012 https://doi.org/10.1039/JR9580004227 https://doi.org/10.1039/jr9580004234 https://doi.org/10.1039/jr9610002312 https://doi.org/10.1248/cpb.54.1653 https://doi.org/10.1016/j.tet.2013.12.055 https://doi.org/10.1016/j.bmc.2012.11.014 https://doi.org/10.1016/j.bmc.2007.06.037 https://doi.org/10.1016/j.bmc.2007.02.030 https://doi.org/10.1016/j.tetlet.2014.09.119 https://doi.org/10.1016/S0223-5234(01)01332-0 https://doi.org/10.1016/j.ejmech.2014.07.076 https://doi.org/10.13005/ojc/330104 https://doi.org/10.1016/S0887-2333(03)00017-1 https://doi.org/10.1016/j.foodres.2012.12.035 https://doi.org/10.1186/1743-422X-9-98 https://doi.org/10.1039/jr9550003982 https://doi.org/10.2174/092986705774370736 https://doi.org/10.1016/j.biortech.2004.02.024 https://doi.org/10.1016/j.foodchem.2006.09.011 https://doi.org/10.1016/j.foodres.2007.10.001 https://doi.org/10.1155/2009/612805 https://doi.org/10.1111/j.1365-2621.2003.tb07029.x https://doi.org/10.1016/0022-1759(83)90303-4 https://doi.org/10.1002/cyto.10080 [1] Ndhlala A., MoyoM., Van Staden J.:Molecules, 2010, 15,6905. https://doi.org/10.3390/molecules15106905 [2] Cheng J., Huang A., Hour T., Yang S.: Eur. J. Med. Chem.,2011, 46, 1222. https://doi.org/10.1016/j.ejmech.2011.01.043 [3] Stefoska-Needham A., Beck E., Johnson S., Tapsell L.: Food Rev. Inter., 2015, 31, 401.https://doi.org/10.1080/87559129.2015.1022832 [4] Jiang D., Dai Z., Li Y.: Drug Rev., 2004, 22, 91. [5] Zarena A., Sankar K.: J. Supercrit. Fluid., 2009, 4, 330.https://doi.org/10.1016/j.supflu.2009.03.004 [6] Branen A.: J. Am. Oil Chem. Soc., 1975, 52, 59.https://doi.org/10.1007/BF02901825 [7] Lee B., Lee J., Lee S. et al.: Bioorg. Med. Chem. Lett., 2005, 15,5548. https://doi.org/10.1016/j.bmcl.2005.08.099 [8] PlazaM., Pozzo T., Liu J. et al.: J. Agric. Food. Chem., 2014,62, 3321. https://doi.org/10.1021/jf405570u [9] Santos C., FreitasM., Ribeiro D. et al.: Bioorg. Med. Chem.2010,18, 6776. https://doi.org/10.1016/j.bmc.2010.07.044 [10] Han A-R., Kim J-A., Lantvit D. et al.: J. Nat. Prod., 2009, 72,2028. https//doi.org/10.1021/np900517h [11] Brogden P., Gabbutt C., Hepworth J.: [in:] Katritzky A., Rees C. (Eds.), Comprehensive HeterocyclicChemistry, v. 3. Pergamon Press, Oxford 1984, 835-840. [12] Finnegan R., Merkel K.: J. Org. Chem., 1972, 37, 2986.https://doi.org/10.1021/jo00984a016 [13] Quillinan A., Scheinmann F.: J. Chem. Soc. Perk. T. 1, 1973, 0,1329. https://doi.org/10.1039/p19730001329 [14] Sandifer R., Bhattacharya A., Harris T.: J. Org. Chem., 1981;46, 2260. https://doi.org/10.1021/jo00324a012 [15] Goldberg A., Wragg A.: J. Chem. Soc., 1958, 0, 4227.https://doi.org/10.1039/JR9580004227 [16] Goldberg A., Wragg A.: J. Chem. Soc., 1958, 0, 4234.https://doi.org/10.1039/jr9580004234 [17] Hassall C., Lewis J.: J. Chem. Soc., 1961, 0, 2312.https://doi.org/10.1039/jr9610002312 [18] Suzuki Y., Toyota T., Miyasihita A., SatoM.: Chem. Pharm. Bull., 2006, 54, 1653. https://doi.org/10.1248/cpb.54.1653 [19] Giallombardo D., Nevin A., Lewis W. et al.: Tetrahedron,2014, 70, 1283. https://doi.org/10.1016/j.tet.2013.12.055 [20] Szkaradek N., Rapacz A., Pytka K. et al.: Bioorg. Med. Chem.,2013, 21, 514. https://doi.org/10.1016/j.bmc.2012.11.014 [21] Castanheiro R., PintoM., Silva A. et al.: Bioorg. Med. Chem.,2007, 15, 6080. https://doi.org/10.1016/j.bmc.2007.06.037 [22] Cheng J., Huang A., Hour T. et al.: Eur. J. Med. Chem., 2011,46, 1222. https://doi.org/10.1016/j.ejmech.2011.01.043 [23] Liu Y., Ma L., Chen W. et al.: Bioorg. Med. Chem., 2007, 15,2810. https://doi.org/10.1016/j.bmc.2007.02.030 [24] Xu Y., Zhou J., Zhang C. et al.: Tetrahedron Lett., 2014, 55,6432. https://doi.org/10.1016/j.tetlet.2014.09.119 [25]Moreau S., Varache-LembegeM., Larrouture S. et al.: Eur. J. Med. Chem., 2002, 37, 237. https://doi.org/10.1016/S0223-5234(01)01332-0 [26] Yang Z., Huang J., Qin J-K. et al.: Eur. J. Med. Chem., 2014,85, 487. https://doi.org/10.1016/j.ejmech.2014.07.076 [27] Syahri J., Yuanita E., Nurohmah B. et al.: J. Chem., 2017, 33,29. https://doi.org/10.13005/ojc/330104 [28] Romero D., Gomez-ZapataM., Luna A., Garcia-Fernandez J.: Toxicol. In Vitro, 2003, 17, 293. https://doi.org/10.1016/S0887-2333(03)00017-1 [29] Borges G., Gonzaga L., Jardini F. et al.: Food Res. Int., 2013,51, 363. https://doi.org/10.1016/j.foodres.2012.12.035 [30]Molyneux P.: Songklanakarin J. Sci. Technol., 2004, 26, 211. [31] Bag P., Chattopadhyay D., Mukherjee H. et al.: J. Virol., 2012,9, 98. https://doi.org/10.1186/1743-422X-9-98 [32] Grover P., Shah G., Shah R.: J. Chem. Soc., 1955, 0, 3982.https://doi.org/10.1039/jr9550003982 [33] SousaM., PintoM.: Curr. Med. Chem., 2005, 12, 2447.https://doi.org/10.2174/092986705774370736 [34] Setha B., Gaspersz F., Fidors A. et al.: Int. J. Sci. Tech. Res.,2013, 26, 221. [35] Dizhbite T., Telysheva G., Jurkjane V., Viesturs U. : Biores. Technol., 2004, 95, 309.https://doi.org/10.1016/j.biortech.2004.02.024 [36] Susanti D., Sirat H., Ahmad F. et al.: Food Chem., 2007, 103,710. https://doi.org/10.1016/j.foodchem.2006.09.011 [37] Ali S., Kasoju N., Luthra A. et al.: Food. Res. Int., 2008, 41, 1.https://doi.org/10.1016/j.foodres.2007.10.001 [38] Prasad K., Hao J., Yi C. et al.: J. Biomed. Biotech., 2009, 2009,1. https://doi.org/10.1155/2009/612805 [39] JunM., Fu H-Y., Hong J. et al.: J. Food Sci., 2003, 68, 2117.https://doi.org/10.1111/j.1365-2621.2003.tb07029.x [40] Bondet V., Williams W., Berset C.: Lebensmittel- WissenschaftUnTechnologie, 1997, 30, 609. [41]Mosmann T.: J. Immunol. Method., 1983, 65, 55.https://doi.org/10.1016/0022-1759(83)90303-4 [42] Bernas T., Dobrucki J.: Cytometry, 2002, 47, 236.https://doi.org/10.1002/cyto.10080 [1] Ndhlala A., MoyoM., Van Staden J.:Molecules, 2010, 15,6905. https://doi.org/10.3390/molecules15106905 [2] Cheng J., Huang A., Hour T., Yang S., Eur. J. Med. Chem.,2011, 46, 1222. https://doi.org/10.1016/j.ejmech.2011.01.043 [3] Stefoska-Needham A., Beck E., Johnson S., Tapsell L., Food Rev. Inter., 2015, 31, 401.https://doi.org/10.1080/87559129.2015.1022832 [4] Jiang D., Dai Z., Li Y., Drug Rev., 2004, 22, 91. [5] Zarena A., Sankar K., J. Supercrit. Fluid., 2009, 4, 330.https://doi.org/10.1016/j.supflu.2009.03.004 [6] Branen A., J. Am. Oil Chem. Soc., 1975, 52, 59.https://doi.org/10.1007/BF02901825 [7] Lee B., Lee J., Lee S. et al., Bioorg. Med. Chem. Lett., 2005, 15,5548. https://doi.org/10.1016/j.bmcl.2005.08.099 [8] PlazaM., Pozzo T., Liu J. et al., J. Agric. Food. Chem., 2014,62, 3321. https://doi.org/10.1021/jf405570u [9] Santos C., FreitasM., Ribeiro D. et al., Bioorg. Med. Chem.2010,18, 6776. https://doi.org/10.1016/j.bmc.2010.07.044 [10] Han A-R., Kim J-A., Lantvit D. et al., J. Nat. Prod., 2009, 72,2028. https//doi.org/10.1021/np900517h [11] Brogden P., Gabbutt C., Hepworth J., [in:] Katritzky A., Rees C. (Eds.), Comprehensive HeterocyclicChemistry, v. 3. Pergamon Press, Oxford 1984, 835-840. [12] Finnegan R., Merkel K., J. Org. Chem., 1972, 37, 2986.https://doi.org/10.1021/jo00984a016 [13] Quillinan A., Scheinmann F., J. Chem. Soc. Perk. T. 1, 1973, 0,1329. https://doi.org/10.1039/p19730001329 [14] Sandifer R., Bhattacharya A., Harris T., J. Org. Chem., 1981;46, 2260. https://doi.org/10.1021/jo00324a012 [15] Goldberg A., Wragg A., J. Chem. Soc., 1958, 0, 4227.https://doi.org/10.1039/JR9580004227 [16] Goldberg A., Wragg A., J. Chem. Soc., 1958, 0, 4234.https://doi.org/10.1039/jr9580004234 [17] Hassall C., Lewis J., J. Chem. Soc., 1961, 0, 2312.https://doi.org/10.1039/jr9610002312 [18] Suzuki Y., Toyota T., Miyasihita A., SatoM., Chem. Pharm. Bull., 2006, 54, 1653. https://doi.org/10.1248/cpb.54.1653 [19] Giallombardo D., Nevin A., Lewis W. et al., Tetrahedron,2014, 70, 1283. https://doi.org/10.1016/j.tet.2013.12.055 [20] Szkaradek N., Rapacz A., Pytka K. et al., Bioorg. Med. Chem.,2013, 21, 514. https://doi.org/10.1016/j.bmc.2012.11.014 [21] Castanheiro R., PintoM., Silva A. et al., Bioorg. Med. Chem.,2007, 15, 6080. https://doi.org/10.1016/j.bmc.2007.06.037 [22] Cheng J., Huang A., Hour T. et al., Eur. J. Med. Chem., 2011,46, 1222. https://doi.org/10.1016/j.ejmech.2011.01.043 [23] Liu Y., Ma L., Chen W. et al., Bioorg. Med. Chem., 2007, 15,2810. https://doi.org/10.1016/j.bmc.2007.02.030 [24] Xu Y., Zhou J., Zhang C. et al., Tetrahedron Lett., 2014, 55,6432. https://doi.org/10.1016/j.tetlet.2014.09.119 [25]Moreau S., Varache-LembegeM., Larrouture S. et al., Eur. J. Med. Chem., 2002, 37, 237. https://doi.org/10.1016/S0223-5234(01)01332-0 [26] Yang Z., Huang J., Qin J-K. et al., Eur. J. Med. Chem., 2014,85, 487. https://doi.org/10.1016/j.ejmech.2014.07.076 [27] Syahri J., Yuanita E., Nurohmah B. et al., J. Chem., 2017, 33,29. https://doi.org/10.13005/ojc/330104 [28] Romero D., Gomez-ZapataM., Luna A., Garcia-Fernandez J., Toxicol. In Vitro, 2003, 17, 293. https://doi.org/10.1016/S0887-2333(03)00017-1 [29] Borges G., Gonzaga L., Jardini F. et al., Food Res. Int., 2013,51, 363. https://doi.org/10.1016/j.foodres.2012.12.035 [30]Molyneux P., Songklanakarin J. Sci. Technol., 2004, 26, 211. [31] Bag P., Chattopadhyay D., Mukherjee H. et al., J. Virol., 2012,9, 98. https://doi.org/10.1186/1743-422X-9-98 [32] Grover P., Shah G., Shah R., J. Chem. Soc., 1955, 0, 3982.https://doi.org/10.1039/jr9550003982 [33] SousaM., PintoM., Curr. Med. Chem., 2005, 12, 2447.https://doi.org/10.2174/092986705774370736 [34] Setha B., Gaspersz F., Fidors A. et al., Int. J. Sci. Tech. Res.,2013, 26, 221. [35] Dizhbite T., Telysheva G., Jurkjane V., Viesturs U. : Biores. Technol., 2004, 95, 309.https://doi.org/10.1016/j.biortech.2004.02.024 [36] Susanti D., Sirat H., Ahmad F. et al., Food Chem., 2007, 103,710. https://doi.org/10.1016/j.foodchem.2006.09.011 [37] Ali S., Kasoju N., Luthra A. et al., Food. Res. Int., 2008, 41, 1.https://doi.org/10.1016/j.foodres.2007.10.001 [38] Prasad K., Hao J., Yi C. et al., J. Biomed. Biotech., 2009, 2009,1. https://doi.org/10.1155/2009/612805 [39] JunM., Fu H-Y., Hong J. et al., J. Food Sci., 2003, 68, 2117.https://doi.org/10.1111/j.1365-2621.2003.tb07029.x [40] Bondet V., Williams W., Berset C., Lebensmittel- WissenschaftUnTechnologie, 1997, 30, 609. [41]Mosmann T., J. Immunol. Method., 1983, 65, 55.https://doi.org/10.1016/0022-1759(83)90303-4 [42] Bernas T., Dobrucki J., Cytometry, 2002, 47, 236.https://doi.org/10.1002/cyto.10080 |
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| Rights |
© Національний університет „Львівська політехніка“, 2018
©Yuanita E., Pranowo H., Siswanta D., Swasono R., Mustofa, ZulkarnainA., Syahri J., Jumina, 2018 |
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290-295
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Lviv
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| Publisher |
Lviv Politechnic Publishing House
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