One-pot synthesis, antioxidant activity and toxicity evaluation of some hydroxyxanthones

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dc.citation.epage295
dc.citation.issue3
dc.citation.journalTitleChemistry & Chemical Technology
dc.citation.spage290
dc.citation.volume12
dc.contributor.affiliationUniversitas Mataram, Indonesia
dc.contributor.affiliationUniversitas Gadjah, Mada, Indonesia
dc.contributor.affiliationUniversitas Muhammadiyah Riau, Indonesia
dc.contributor.authorYuanita, Emmy
dc.contributor.authorPranowo, Harno Dwi
dc.contributor.authorSiswanta, Dwi
dc.contributor.authorSwasono, Respati Tri
dc.contributor.authorMustofa
dc.contributor.authorZulkarnain, Abdul Karim
dc.contributor.authorSyahri, Jufrizal
dc.contributor.authorJumina
dc.coverage.placenameLviv
dc.date.accessioned2019-06-20T11:19:49Z
dc.date.available2019-06-20T11:19:49Z
dc.date.created2018-01-20
dc.date.issued2018-01-20
dc.description.abstractЗа 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.
dc.description.abstractSome 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.
dc.format.extent290-295
dc.format.pages6
dc.identifier.citationOne-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.
dc.identifier.citationenOne-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.
dc.identifier.urihttps://ena.lpnu.ua/handle/ntb/45184
dc.language.isoen
dc.publisherLviv Politechnic Publishing House
dc.relation.ispartofChemistry & Chemical Technology, 3 (12), 2018
dc.relation.references[1] Ndhlala A., MoyoM., Van Staden J.:Molecules, 2010, 15,6905. https://doi.org/10.3390/molecules15106905
dc.relation.references[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
dc.relation.references[3] Stefoska-Needham A., Beck E., Johnson S., Tapsell L.: Food Rev. Inter., 2015, 31, 401.https://doi.org/10.1080/87559129.2015.1022832
dc.relation.references[4] Jiang D., Dai Z., Li Y.: Drug Rev., 2004, 22, 91.
dc.relation.references[5] Zarena A., Sankar K.: J. Supercrit. Fluid., 2009, 4, 330.https://doi.org/10.1016/j.supflu.2009.03.004
dc.relation.references[6] Branen A.: J. Am. Oil Chem. Soc., 1975, 52, 59.https://doi.org/10.1007/BF02901825
dc.relation.references[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
dc.relation.references[8] PlazaM., Pozzo T., Liu J. et al.: J. Agric. Food. Chem., 2014,62, 3321. https://doi.org/10.1021/jf405570u
dc.relation.references[9] Santos C., FreitasM., Ribeiro D. et al.: Bioorg. Med. Chem.2010,18, 6776. https://doi.org/10.1016/j.bmc.2010.07.044
dc.relation.references[10] Han A-R., Kim J-A., Lantvit D. et al.: J. Nat. Prod., 2009, 72,2028. https//doi.org/10.1021/np900517h
dc.relation.references[11] Brogden P., Gabbutt C., Hepworth J.: [in:] Katritzky A., Rees C. (Eds.), Comprehensive HeterocyclicChemistry, v. 3. Pergamon Press, Oxford 1984, 835-840.
dc.relation.references[12] Finnegan R., Merkel K.: J. Org. Chem., 1972, 37, 2986.https://doi.org/10.1021/jo00984a016
dc.relation.references[13] Quillinan A., Scheinmann F.: J. Chem. Soc. Perk. T. 1, 1973, 0,1329. https://doi.org/10.1039/p19730001329
dc.relation.references[14] Sandifer R., Bhattacharya A., Harris T.: J. Org. Chem., 1981;46, 2260. https://doi.org/10.1021/jo00324a012
dc.relation.references[15] Goldberg A., Wragg A.: J. Chem. Soc., 1958, 0, 4227.https://doi.org/10.1039/JR9580004227
dc.relation.references[16] Goldberg A., Wragg A.: J. Chem. Soc., 1958, 0, 4234.https://doi.org/10.1039/jr9580004234
dc.relation.references[17] Hassall C., Lewis J.: J. Chem. Soc., 1961, 0, 2312.https://doi.org/10.1039/jr9610002312
dc.relation.references[18] Suzuki Y., Toyota T., Miyasihita A., SatoM.: Chem. Pharm. Bull., 2006, 54, 1653. https://doi.org/10.1248/cpb.54.1653
dc.relation.references[19] Giallombardo D., Nevin A., Lewis W. et al.: Tetrahedron,2014, 70, 1283. https://doi.org/10.1016/j.tet.2013.12.055
dc.relation.references[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
dc.relation.references[21] Castanheiro R., PintoM., Silva A. et al.: Bioorg. Med. Chem.,2007, 15, 6080. https://doi.org/10.1016/j.bmc.2007.06.037
dc.relation.references[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
dc.relation.references[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
dc.relation.references[24] Xu Y., Zhou J., Zhang C. et al.: Tetrahedron Lett., 2014, 55,6432. https://doi.org/10.1016/j.tetlet.2014.09.119
dc.relation.references[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
dc.relation.references[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
dc.relation.references[27] Syahri J., Yuanita E., Nurohmah B. et al.: J. Chem., 2017, 33,29. https://doi.org/10.13005/ojc/330104
dc.relation.references[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
dc.relation.references[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
dc.relation.references[30]Molyneux P.: Songklanakarin J. Sci. Technol., 2004, 26, 211.
dc.relation.references[31] Bag P., Chattopadhyay D., Mukherjee H. et al.: J. Virol., 2012,9, 98. https://doi.org/10.1186/1743-422X-9-98
dc.relation.references[32] Grover P., Shah G., Shah R.: J. Chem. Soc., 1955, 0, 3982.https://doi.org/10.1039/jr9550003982
dc.relation.references[33] SousaM., PintoM.: Curr. Med. Chem., 2005, 12, 2447.https://doi.org/10.2174/092986705774370736
dc.relation.references[34] Setha B., Gaspersz F., Fidors A. et al.: Int. J. Sci. Tech. Res.,2013, 26, 221.
dc.relation.references[35] Dizhbite T., Telysheva G., Jurkjane V., Viesturs U. : Biores. Technol., 2004, 95, 309.https://doi.org/10.1016/j.biortech.2004.02.024
dc.relation.references[36] Susanti D., Sirat H., Ahmad F. et al.: Food Chem., 2007, 103,710. https://doi.org/10.1016/j.foodchem.2006.09.011
dc.relation.references[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
dc.relation.references[38] Prasad K., Hao J., Yi C. et al.: J. Biomed. Biotech., 2009, 2009,1. https://doi.org/10.1155/2009/612805
dc.relation.references[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
dc.relation.references[40] Bondet V., Williams W., Berset C.: Lebensmittel- WissenschaftUnTechnologie, 1997, 30, 609.
dc.relation.references[41]Mosmann T.: J. Immunol. Method., 1983, 65, 55.https://doi.org/10.1016/0022-1759(83)90303-4
dc.relation.references[42] Bernas T., Dobrucki J.: Cytometry, 2002, 47, 236.https://doi.org/10.1002/cyto.10080
dc.relation.referencesen[1] Ndhlala A., MoyoM., Van Staden J.:Molecules, 2010, 15,6905. https://doi.org/10.3390/molecules15106905
dc.relation.referencesen[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
dc.relation.referencesen[3] Stefoska-Needham A., Beck E., Johnson S., Tapsell L., Food Rev. Inter., 2015, 31, 401.https://doi.org/10.1080/87559129.2015.1022832
dc.relation.referencesen[4] Jiang D., Dai Z., Li Y., Drug Rev., 2004, 22, 91.
dc.relation.referencesen[5] Zarena A., Sankar K., J. Supercrit. Fluid., 2009, 4, 330.https://doi.org/10.1016/j.supflu.2009.03.004
dc.relation.referencesen[6] Branen A., J. Am. Oil Chem. Soc., 1975, 52, 59.https://doi.org/10.1007/BF02901825
dc.relation.referencesen[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
dc.relation.referencesen[8] PlazaM., Pozzo T., Liu J. et al., J. Agric. Food. Chem., 2014,62, 3321. https://doi.org/10.1021/jf405570u
dc.relation.referencesen[9] Santos C., FreitasM., Ribeiro D. et al., Bioorg. Med. Chem.2010,18, 6776. https://doi.org/10.1016/j.bmc.2010.07.044
dc.relation.referencesen[10] Han A-R., Kim J-A., Lantvit D. et al., J. Nat. Prod., 2009, 72,2028. https//doi.org/10.1021/np900517h
dc.relation.referencesen[11] Brogden P., Gabbutt C., Hepworth J., [in:] Katritzky A., Rees C. (Eds.), Comprehensive HeterocyclicChemistry, v. 3. Pergamon Press, Oxford 1984, 835-840.
dc.relation.referencesen[12] Finnegan R., Merkel K., J. Org. Chem., 1972, 37, 2986.https://doi.org/10.1021/jo00984a016
dc.relation.referencesen[13] Quillinan A., Scheinmann F., J. Chem. Soc. Perk. T. 1, 1973, 0,1329. https://doi.org/10.1039/p19730001329
dc.relation.referencesen[14] Sandifer R., Bhattacharya A., Harris T., J. Org. Chem., 1981;46, 2260. https://doi.org/10.1021/jo00324a012
dc.relation.referencesen[15] Goldberg A., Wragg A., J. Chem. Soc., 1958, 0, 4227.https://doi.org/10.1039/JR9580004227
dc.relation.referencesen[16] Goldberg A., Wragg A., J. Chem. Soc., 1958, 0, 4234.https://doi.org/10.1039/jr9580004234
dc.relation.referencesen[17] Hassall C., Lewis J., J. Chem. Soc., 1961, 0, 2312.https://doi.org/10.1039/jr9610002312
dc.relation.referencesen[18] Suzuki Y., Toyota T., Miyasihita A., SatoM., Chem. Pharm. Bull., 2006, 54, 1653. https://doi.org/10.1248/cpb.54.1653
dc.relation.referencesen[19] Giallombardo D., Nevin A., Lewis W. et al., Tetrahedron,2014, 70, 1283. https://doi.org/10.1016/j.tet.2013.12.055
dc.relation.referencesen[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
dc.relation.referencesen[21] Castanheiro R., PintoM., Silva A. et al., Bioorg. Med. Chem.,2007, 15, 6080. https://doi.org/10.1016/j.bmc.2007.06.037
dc.relation.referencesen[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
dc.relation.referencesen[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
dc.relation.referencesen[24] Xu Y., Zhou J., Zhang C. et al., Tetrahedron Lett., 2014, 55,6432. https://doi.org/10.1016/j.tetlet.2014.09.119
dc.relation.referencesen[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
dc.relation.referencesen[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
dc.relation.referencesen[27] Syahri J., Yuanita E., Nurohmah B. et al., J. Chem., 2017, 33,29. https://doi.org/10.13005/ojc/330104
dc.relation.referencesen[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
dc.relation.referencesen[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
dc.relation.referencesen[30]Molyneux P., Songklanakarin J. Sci. Technol., 2004, 26, 211.
dc.relation.referencesen[31] Bag P., Chattopadhyay D., Mukherjee H. et al., J. Virol., 2012,9, 98. https://doi.org/10.1186/1743-422X-9-98
dc.relation.referencesen[32] Grover P., Shah G., Shah R., J. Chem. Soc., 1955, 0, 3982.https://doi.org/10.1039/jr9550003982
dc.relation.referencesen[33] SousaM., PintoM., Curr. Med. Chem., 2005, 12, 2447.https://doi.org/10.2174/092986705774370736
dc.relation.referencesen[34] Setha B., Gaspersz F., Fidors A. et al., Int. J. Sci. Tech. Res.,2013, 26, 221.
dc.relation.referencesen[35] Dizhbite T., Telysheva G., Jurkjane V., Viesturs U. : Biores. Technol., 2004, 95, 309.https://doi.org/10.1016/j.biortech.2004.02.024
dc.relation.referencesen[36] Susanti D., Sirat H., Ahmad F. et al., Food Chem., 2007, 103,710. https://doi.org/10.1016/j.foodchem.2006.09.011
dc.relation.referencesen[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
dc.relation.referencesen[38] Prasad K., Hao J., Yi C. et al., J. Biomed. Biotech., 2009, 2009,1. https://doi.org/10.1155/2009/612805
dc.relation.referencesen[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
dc.relation.referencesen[40] Bondet V., Williams W., Berset C., Lebensmittel- WissenschaftUnTechnologie, 1997, 30, 609.
dc.relation.referencesen[41]Mosmann T., J. Immunol. Method., 1983, 65, 55.https://doi.org/10.1016/0022-1759(83)90303-4
dc.relation.referencesen[42] Bernas T., Dobrucki J., Cytometry, 2002, 47, 236.https://doi.org/10.1002/cyto.10080
dc.relation.urihttps://doi.org/10.3390/molecules15106905
dc.relation.urihttps://doi.org/10.1016/j.ejmech.2011.01.043
dc.relation.urihttps://doi.org/10.1080/87559129.2015.1022832
dc.relation.urihttps://doi.org/10.1016/j.supflu.2009.03.004
dc.relation.urihttps://doi.org/10.1007/BF02901825
dc.relation.urihttps://doi.org/10.1016/j.bmcl.2005.08.099
dc.relation.urihttps://doi.org/10.1021/jf405570u
dc.relation.urihttps://doi.org/10.1016/j.bmc.2010.07.044
dc.relation.urihttps://doi.org/10.1021/jo00984a016
dc.relation.urihttps://doi.org/10.1039/p19730001329
dc.relation.urihttps://doi.org/10.1021/jo00324a012
dc.relation.urihttps://doi.org/10.1039/JR9580004227
dc.relation.urihttps://doi.org/10.1039/jr9580004234
dc.relation.urihttps://doi.org/10.1039/jr9610002312
dc.relation.urihttps://doi.org/10.1248/cpb.54.1653
dc.relation.urihttps://doi.org/10.1016/j.tet.2013.12.055
dc.relation.urihttps://doi.org/10.1016/j.bmc.2012.11.014
dc.relation.urihttps://doi.org/10.1016/j.bmc.2007.06.037
dc.relation.urihttps://doi.org/10.1016/j.bmc.2007.02.030
dc.relation.urihttps://doi.org/10.1016/j.tetlet.2014.09.119
dc.relation.urihttps://doi.org/10.1016/S0223-5234(01)01332-0
dc.relation.urihttps://doi.org/10.1016/j.ejmech.2014.07.076
dc.relation.urihttps://doi.org/10.13005/ojc/330104
dc.relation.urihttps://doi.org/10.1016/S0887-2333(03)00017-1
dc.relation.urihttps://doi.org/10.1016/j.foodres.2012.12.035
dc.relation.urihttps://doi.org/10.1186/1743-422X-9-98
dc.relation.urihttps://doi.org/10.1039/jr9550003982
dc.relation.urihttps://doi.org/10.2174/092986705774370736
dc.relation.urihttps://doi.org/10.1016/j.biortech.2004.02.024
dc.relation.urihttps://doi.org/10.1016/j.foodchem.2006.09.011
dc.relation.urihttps://doi.org/10.1016/j.foodres.2007.10.001
dc.relation.urihttps://doi.org/10.1155/2009/612805
dc.relation.urihttps://doi.org/10.1111/j.1365-2621.2003.tb07029.x
dc.relation.urihttps://doi.org/10.1016/0022-1759(83)90303-4
dc.relation.urihttps://doi.org/10.1002/cyto.10080
dc.rights.holder© Національний університет „Львівська політехніка“, 2018
dc.rights.holder©Yuanita E., Pranowo H., Siswanta D., Swasono R., Mustofa, ZulkarnainA., Syahri J., Jumina, 2018
dc.subjectантиоксидант
dc.subjectгідроксиксантони
dc.subject2
dc.subject2- дифеніл-1-пікрилгідразил
dc.subjectреагент Ітона
dc.subjectantioxidant
dc.subjecthydroxyxanthones
dc.subject2
dc.subject2-diphenyl- 1-picrylhydrazyl assay
dc.subjectEaton’s reagent
dc.titleOne-pot synthesis, antioxidant activity and toxicity evaluation of some hydroxyxanthones
dc.title.alternativeОдностадійний синтез і оцінка антиокиснювальної активності та токсичності деяких гідроксиксантонів
dc.typeArticle

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Chemistry & Chemical Technology. – 2018. – Vol. 12, No. 3