Chemical evidence for potent xanthine oxidase inhibitory activity of ethyl acetate extract of Citrus aurantium L. dried immature fruits

Molecules

Volumn 21, Issue 3, 2016, Pages

  Liu, Kun ^a   Wang, Wei ^a   Guo, Bing Hua ^a   Gao, Hua ^a   Liu, Yang ^a   Liu, Xiao Hong ^a   Yao, Hui Li ^a   Cheng, Kun ^a  

^a QINGDAO UNIVERSITY   (China)

Author keywords

Aurantii fructus immaturus; Citrus; Hesperetin; Xanthine oxidase

Indexed keywords

ACETIC ACID DERIVATIVE; ACETIC ACID ETHYL ESTER; ENZYME INHIBITOR; FLAVANONE DERIVATIVE; FLAVONE DERIVATIVE; HESPERETIN; HESPERIDIN; NARINGENIN; NOBILETIN; PLANT EXTRACT; XANTHINE OXIDASE;

ANTAGONISTS AND INHIBITORS; CHEMICAL STRUCTURE; CHEMISTRY; CITRUS; FRUIT; HUMAN; HYPERURICEMIA; IN VITRO STUDY; ISOLATION AND PURIFICATION; PHYTOTHERAPY;

ACETATES; CITRUS; ENZYME INHIBITORS; FLAVANONES; FLAVONES; FRUIT; HESPERIDIN; HUMANS; HYPERURICEMIA; IN VITRO TECHNIQUES; MOLECULAR STRUCTURE; PHYTOTHERAPY; PLANT EXTRACTS; XANTHINE OXIDASE;

EID: 84963677395     PISSN: None     EISSN: 14203049     Source Type: Journal    
DOI: 10.3390/molecules21030302     Document Type: Article

References (28)

1. Richette, P.; Bardin, T. Gout. Lancet 2010, 375, 318-328. [CrossRef]
2. Hsieh, J.F.; Wu, S.H.; Yang, Y.L.; Choog, K.F.; Chen, S.T. The screen and characterization of 6-aminopurinebased xanthine oxidase inhibitors. Bioorg. Med. Chem. 2007, 15, 3450-3456. [CrossRef] [PubMed]
3. Terkeltaub, R.A. Clinical practice. Gout. N. Engl. J. Med. 2003, 334, 1647-1655. [CrossRef] [PubMed]
4. Becker, M.A.; Kisicki, J.; Khosravan, R.; Wu, J.; Mulford, D.; Hunt, B.; MacDonald, P.; Joseph-Ridge, N. Febuxostat (TMX-67), a novel, non-purine, selective inhibitor of xanthine oxidase, is safe and decreases serum urate in healthy volunteers. Nucleos. Nucleot. Nucl. 2004, 23, 1111-1116. [CrossRef] [PubMed]
5. Fukunari, A.; Okamato, K.; Nishino, T.; Eger, B.T.; Pai, E.F.; Kamezawa, M.; Yamada, I.; Kato, N. Y-700 [1-[3-cyano-4-(2,2-dimethylpropoxy)phenyl]-1H-pyrazole-4-carboxylic acid]: A potent xanthine oxidoreductase inhibitor with hepatic excretion. J. Pharmacol. Exp. Ther. 2004, 311, 519-528. [CrossRef] [PubMed]
6. Pacher, P.; Nivorozhkin, A.; Szabo, C. Therapeutic effects of xanthine oxidase inhibitor: Renaissance half a century after the discovery of allopurinol. Pharmacol. Rev. 2006, 58, 87-114. [CrossRef] [PubMed]
7. Nguyen, M.T.T.; Awale, S.; Tezuka, Y.; Ueda, J.Y.; Tran, Q.L.; Kadota, S. Xanthine oxidase inhibitors from the flowers of Chrysanthemum sinense. Planta Med. 2006, 72, 46-51. [CrossRef] [PubMed]
8. Spanou, C.; Veskoukis, A.S.; Kerasioti, T.; Kontou, M.; Angelis, A.; Aligiannis, N.; Skaltsounis, A.L.; Kouretas, D. Flavonoid glycosides isolated from unique legume plant extracts as novel inhibitors of xanthine oxidase. PLoS ONE 2012, 7, e32214. [CrossRef] [PubMed]
9. Nile, S.H.; Park, S.W. Antioxidant, α-glucosidase and xanthine oxidase inhibitory activity of bioactive compounds from maize (Zea mays L.). Chem. Biol. Drug Des. 2014, 83, 119-125. [CrossRef] [PubMed]
10. Liu, H.X.; He, M.T.; Tan, H.B.; Gu, W.; Yang, S.X.; Wang, Y.H.; Li, L.; Long, C.L. Xanthine oxidase inhibitors isolated from Piper nudibaccatum. Phytochem. Lett. 2015, 12, 133-137. [CrossRef]
11. Luo, Y.L.; Qu, W.; Liang, J.Y. Progress on chemical constituents and biological activities of the genus Citrus. Strait Pharm. J. 2013, 25. [CrossRef]
12. Mencherini, T.; Campone, L.; Piccinelli, A.L.; Mesa, M.G.; Sánchez, D.M.; Aquino, R.P.; Rastrelli, L. HPLC-PDA-MS and NMR characterization of a hydroalcoholic extract of Citrus aurantium L. var. amara Peel with antiedematogenic activity. J. Agric. Food Chem. 2013, 61, 1686-1693. [PubMed]
13. Huo, L.N.; Wang, W.; Zhang, C.Y.; Shi, H.B.; Liu, Y.; Liu, X.H.; Guo, B.H.; Zhao, D.M.; Gao, H. Bioassy-guided isolation and identification of xanthine oxidase inhibitory constituents from the leaves of Perilla frutescens. Molecules 2015, 20, 17848-17859. [CrossRef] [PubMed]
14. Li, X.C.; Liu, X.H.; Gao, H.; Fan, M.L.; Liu, K.; Wang, W. Study on inhibition and enzyme kinetics of different solvent extractions from Polygonum cuspidatum on xanthine oxidase. China Pharm. 2015, 26, 494-496.
15. Lin, J.K.; Chen, P.C.; Ho, C.T.; Lin-Shiau, S.Y. Inhibition of xanthine oxidase and suppression of intracellular reactive oxygen species in HL-60 cells by theaflavin-3,3′-digallate, (-)-epigallocatechin-3-gallate, and propyl gallate. J. Agric. Food Chem. 2010, 48, 2736-3743. [CrossRef]
16. Casquete, R.; Castro, S.M.; Martín, A.; Ruiz-Moyano, S.; Saraiva, J.A.; Córdoba, M.G.; Teixeira, P. Evaluation of the effect of high pressure on total phenolic content, antioxidant and antimicrobial activity of citrus peels. Innov. Food Sci. Emerg. 2015, 31, 37-44. [CrossRef]
17. Mehmood, B.; Dar, K.K.; Ali, S.; Awan, U.A.; Nayyer, A.Q.; Ghous, T.; Andleeb, S. In vitro assessment of antioxidant, antibacterial and phytochemical analysis of Citrus sinensis. Pak. J. Pharm. Sci. 2015, 28, 231-239. [PubMed]
18. Sharma, S.; Kori, S.; Parmar, A. Surfactant mediated extraction of total phenolic content (TPC) and antioxidants from fruits juices. Food Chem. 2015, 185, 284-288. [CrossRef] [PubMed]
19. Maltese, F.; Erkelens, C.; Kooy, F.; Choi, Y.H.; Verpoorte, R. Identification of natural epimeric flavanone glycosides by NMR spectroscopy. Food Chem. 2009, 116, 575-579. [CrossRef]
20. Lei, H.M.; Sun, W.J.; Lin, W.H. Studies on chemical constituents of Citrus grandis Osbecks. Var. tomentosa Hort. Northwest Pharm. J. 2000, 15, 203-204.
21. Guo, X.L.; Wang, T.J.; Guo, M.J.; Chen, Y. Studies on chemical constituents of processed green tangerine peel. Chin. J. Chin. Mater. Med. 2000, 25, 146-148.
22. Feng, F.; Wang, X.N.; Yan, C.M. Studies on chemical constituents of Citrus aurantium L. Asia-Pac. Tradit. Med. 2012, 8, 22-24.
23. Chen, X.X.; Shimayi, R.H.M.; Long, S.J. Studies on chemical constituents of Toddalia asiatica stems. Northwest Pharm. J. 2013, 28, 337-339.
24. Han, S.; Kim, H.M.; Lee, J.M.; Mok, S.Y.; Lee, S. Isolation and identification of polymethoxyflavones from the hybrid Citrus, Hallabong. J. Agric. Food Chem. 2010, 58, 9488-9491. [CrossRef] [PubMed]
25. Dew, T.P.; Day, A.J.; Morgan, M.R.A. Xanthine oxidase activity in vitro: Effects of food extracts and components. J. Agric. Food Chem. 2005, 53, 6510-6515. [CrossRef] [PubMed]
26. Kim, D.H.; Jung, E.A.; Sohng, I.S.; Han, J.A.; Kim, T.H.; Han, M.J. Intestinal bacterial metabolism of flavonoids and its relation to some biological activities. Arch. Pharm. Res. 1998, 21, 17-23. [CrossRef] [PubMed]
27. Zhang, W.; Jiang, S.; Qian, D.W.; Shang, E.X.; Duan, J.A. Determination of metabolism of neohesperidin by human intestinal bacteria by UPLC-Q-TOF/MS. Chromatographia 2014, 77, 439-445. [CrossRef]
28. Masuda, A.; Takahashi, C.; Inai, M.; Miura, Y.; Masuda, T. Chemical evidence for potent xanthine oxidase inhibitory activity of Glechoma hederacea var. grandis leaves (Kakidoushi-Cha). J. Nutr. Sci. Vitaminol. 2013, 59, 570-575. [CrossRef] [PubMed]