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

Yuanita, Emmy; Pranowo, Harno Dwi; Siswanta, Dwi; Swasono, Respati Tri; Mustofa; Zulkarnain, Abdul Karim; Syahri, Jufrizal; Jumina

Please use this identifier to cite or link to this item: https://oldena.lpnu.ua/handle/ntb/45184

Title:	One-pot synthesis, antioxidant activity and toxicity evaluation of some hydroxyxanthones
Other Titles:	Одностадійний синтез і оцінка антиокиснювальної активності та токсичності деяких гідроксиксантонів
Authors:	Yuanita, Emmy Pranowo, Harno Dwi Siswanta, Dwi Swasono, Respati Tri Mustofa Zulkarnain, Abdul Karim Syahri, Jufrizal Jumina
Affiliation:	Universitas Mataram, Indonesia Universitas Gadjah, Mada, Indonesia Universitas Muhammadiyah Riau, Indonesia
Bibliographic description (Ukraine):	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.
Bibliographic description (International):	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.
Is part of:	Chemistry & Chemical Technology, 3 (12), 2018
Journal/Collection:	Chemistry & Chemical Technology
Issue:	3
Volume:	12
Issue Date:	20-Jan-2018
Publisher:	Lviv Politechnic Publishing House
Place of the edition/event:	Lviv
Keywords:	антиоксидант гідроксиксантони 2 2- дифеніл-1-пікрилгідразил реагент Ітона antioxidant hydroxyxanthones 2 2-diphenyl- 1-picrylhydrazyl assay Eaton’s reagent
Number of pages:	6
Page range:	290-295
Start page:	290
End page:	295
Abstract:	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.
URI:	https://ena.lpnu.ua/handle/ntb/45184
Copyright owner:	© Національний університет „Львівська політехніка“, 2018 ©Yuanita E., Pranowo H., Siswanta D., Swasono R., Mustofa, ZulkarnainA., Syahri J., Jumina, 2018
URL for reference material:	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
References (Ukraine):	[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
References (International):	[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
Content type:	Article
Appears in Collections:	Chemistry & Chemical Technology. – 2018. – Vol. 12, No. 3

Files in This Item:

File	Description	Size	Format
2018v12n3_Yuanita_E-One_pot_synthesis_antioxidant_290-295.pdf		369.59 kB	Adobe PDF	View/Open
2018v12n3_Yuanita_E-One_pot_synthesis_antioxidant_290-295__COVER.png		550.32 kB	image/png	View/Open

Show full item record

putin IS MURDERER