Magnetic Ligand Fishing as a Targeting Tool for HPLC-HRMS-SPE-NMR: α-Glucosidase Inhibitory Ligands and Alkylresorcinol Glycosides from Eugenia catharinae

Journal of Natural Products

Volumn 78, Issue 11, 2015, Pages 2657-2665

  Wubshet, Sileshi G ^a   Brighente, Inês M C ^b   Moaddel, Ruin ^c   Staerk, Dan ^a  

^a UNIVERSITY OF COPENHAGEN   (Denmark)

^b FEDERAL UNIVERSITY OF SANTA CATARINA   (Brazil)

^c NATIONAL INSTITUTE ON AGING   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

3 O METHYL 5 PENTYLRESORCINOL 1 O [BETA DEXTRO GLUCOPYRANOSYL (1-6)] BETA DEXTRO GLUCOPYRANOSIDE; 4 HYDROXY 3 O METHYL 5 PENTYLRESORCINOL 1 O BETA DEXTRO GLUCOPYRANOSIDE; 5 (2 OXOPENTYL)RESORCINOL 4 O BETA DEXTRO GLUCOPYRANOSIDE; 5 PENTYLRESORCINOL 4 O BETA DEXTRO GLUCOPYRANOSIDE; 5 PENTYLRESORCINOL 4 O [ALPHA DECTRO APIOFURANOSYL (1-6)] BETA DEXTRO GLUCOPYRANOSIDE; 5 PROPYLRESORCINOL 4 O BETA GLUCOPYRANOSIDE; ALKYLRESORCINOL GLYCOSIDE DERIVATIVE; ALPHA GLUCOSIDASE; ALPHA GLUCOSIDASE INHIBITOR; CAFFEINE; FERULIC ACID; GLYCOSIDE; IMMOBILIZED ENZYME; KAEMPFEROL; LIGAND; LUTEOLIN; MYRICETIN; MYRICETIN 3 O ALPHA LEVO RHAMNOPYRANOSIDE; QUERCETIN; UNCLASSIFIED DRUG; GLYCOSIDASE INHIBITOR; RESORCINOL DERIVATIVE;

ANALYTIC METHOD; ARTICLE; CATALYSIS; CHEMICAL ANALYSIS; COMPARATIVE STUDY; CONTROLLED STUDY; DRUG IDENTIFICATION; DRUG SCREENING; DRUG STRUCTURE; DRUG SYNTHESIS; ENZYME ACTIVITY; ENZYME INHIBITION; EUGENIA; EUGENIA CATHARINAE; FISHING; HIGH PERFORMANCE LIQUID CHROMATOGRAPHY; MAGNETIC LIGAND FISHING; MASS SPECTROMETRY; NONHUMAN; NUCLEAR MAGNETIC RESONANCE; SOLID PHASE EXTRACTION; BRAZIL; CHEMICAL STRUCTURE; CHEMISTRY; DRUG EFFECTS; ISOLATION AND PURIFICATION; PLANT LEAF;

ALPHA-GLUCOSIDASES; BRAZIL; CHROMATOGRAPHY, HIGH PRESSURE LIQUID; EUGENIA; GLYCOSIDE HYDROLASE INHIBITORS; GLYCOSIDES; LIGANDS; MOLECULAR STRUCTURE; NUCLEAR MAGNETIC RESONANCE, BIOMOLECULAR; PLANT LEAVES; RESORCINOLS;

EID: 84948798632     PISSN: 01633864     EISSN: 15206025     Source Type: Journal    
DOI: 10.1021/acs.jnatprod.5b00603     Document Type: Article

References (36)

1. Bischoff, H. Clin. Invest. Med. 1995, 18, 303-311
2. van de Laar, F. A. Vasc. Health Risk. Manag. 2008, 4, 1189-1195
3. Mooradian, A.; Thurman, J. Drugs 1999, 57, 19-29 10.2165/00003495-199957010-00003
4. van de Laar, F. A.; Lucassen, P. L.; Akkermans, R. P.; van de Lisdonk, E. H.; Rutten, G. E.; van Weel, C. Diabetes Care 2005, 28, 154-163 10.2337/diacare.28.1.154
5. Mata, R.; Cristians, S.; Escandón-Rivera, S.; Juárez-Reyes, K.; Rivero-Cruz, I. J. Nat. Prod. 2013, 76, 468-483 10.1021/np300869g
6. Yin, Z.; Zhang, W.; Feng, F.; Zhang, Y.; Kang, W. Food Science and Human Wellness 2014, 3, 136-174 10.1016/j.fshw.2014.11.003
7. Lourenço, V. K.; Jiang, Z.; Zhang, X.; Vieira, L. C.; Corrêa, A. G.; Cardoso, C. L.; Cass, Q. B.; Moaddel, R. Talanta 2013, 116, 647-652 10.1016/j.talanta.2013.07.046
8. Qing, L.-S.; Xue, Y.; Zheng, Y.; Xiong, J.; Liao, X.; Ding, L.-S.; Li, B.-G.; Liu, Y.-M. J. Chromatogr. A 2010, 1217, 4663-4668 10.1016/j.chroma.2010.05.009
9. Yasuda, M.; Wilson, D. R.; Fugmann, S. D.; Moaddel, R. Anal. Chem. 2011, 83, 7400-7407 10.1021/ac201403y
10. Zhu, Y.-T.; Jia, Y.-W.; Liu, Y.-M.; Liang, J.; Ding, L.-S.; Liao, X. J. Agric. Food Chem. 2014, 62, 10679-10686 10.1021/jf503687e
11. Qing, L.-S.; Xue, Y.; Deng, W.-L.; Liao, X.; Xu, X.-M.; Li, B.-G.; Liu, Y.-M. Anal. Bioanal. Chem. 2011, 399, 1223-1231 10.1007/s00216-010-4399-8
12. Staerk, D.; Kesting, J. R.; Sairafianpour, M.; Witt, M.; Asili, J.; Emami, S. A.; Jaroszewski, J. W. Phytochemistry 2009, 70, 1055-1061 10.1016/j.phytochem.2009.05.004
13. Schmidt, B.; Jaroszewski, J. W.; Bro, R.; Witt, M.; Stærk, D. Anal. Chem. 2008, 80, 1978-1987 10.1021/ac702064p
14. Marszałł, M. Pharm. Res. 2011, 28, 480-483 10.1007/s11095-010-0284-6
15. Sanghvi, M.; Moaddel, R.; Wainer, I. W. J. Chromatogr. A 2011, 1218, 8791-8798 10.1016/j.chroma.2011.05.067
16. Bokesch, H. R.; Wamiru, A.; Le Grice, S. F. J.; Beutler, J. A.; McKee, T. C.; McMahon, J. B. J. Nat. Prod. 2008, 71, 1634-1636 10.1021/np8002518
17. Grangeiro, M. S.; Calheiros-Lima, A. P.; Martins, M. F.; Arruda, L. F.; Garcez-do-Carmo, L.; Santos, W. C. J. Ethnopharmacol. 2006, 108, 26-30 10.1016/j.jep.2006.04.021
18. Omar, R.; Li, L.; Yuan, T.; Seeram, N. P. J. Nat. Prod. 2012, 75, 1505-1509 10.1021/np300417q
19. Prodanović, R.; Milosavić, N.; Jovanović, S.; Prodanović, O.; Ćirković Veličković, T.; Vujčić, Z.; Jankov, R. Biocatal. Biotransform. 2006, 24, 195-200 10.1080/10242420600655903
20. Fernández, A.; Sinanoʇlu, O. Biophys. Chem. 1985, 21, 163-166 10.1016/0301-4622(85)80002-8
21. Yan, J.; Zhang, G.; Pan, J.; Wang, Y. Int. J. Biol. Macromol. 2014, 64, 213-223 10.1016/j.ijbiomac.2013.12.007
22. Schmidt, J. S.; Nyberg, N. T.; Staerk, D. Food Chem. 2014, 161, 192-198 10.1016/j.foodchem.2014.03.062
23. Wubshet, S. G.; Schmidt, J. S.; Wiese, S.; Staerk, D. J. Agric. Food Chem. 2013, 61, 8616-8623 10.1021/jf402949y
24. Liu, B.; Kongstad, K. T.; Qinglei, S.; Nyberg, N. T.; Jäger, A. K.; Staerk, D. J. Nat. Prod. 2015, 78, 294-300 10.1021/np5009416
25. Okutan, L.; Kongstad, K. T.; Jäger, A. K.; Staerk, D. J. Agric. Food Chem. 2014, 62, 11465-11471 10.1021/jf5047283
26. Grosso, C.; Jäger, A. K.; Staerk, D. Phytochem. Anal. 2013, 24, 141-147 10.1002/pca.2393
27. Wiese, S.; Wubshet, S. G.; Nielsen, J.; Staerk, D. Food Chem. 2013, 141, 4010-4018 10.1016/j.foodchem.2013.06.115
28. Kongstad, K. T.; Wubshet, S. G.; Johannesen, A.; Kjellerup, L.; Winther, A.-M. L.; Jäger, A. K.; Staerk, D. J. Agric. Food Chem. 2014, 62, 5595-5602 10.1021/jf501605z
29. Chung, S.-K.; Kim, Y.-C.; Takaya, Y.; Terashima, K.; Niwa, M. J. Agric. Food Chem. 2004, 52, 4664-4668 10.1021/jf049526j
30. Wubshet, S. G.; Moresco, H. H.; Tahtah, Y.; Brighente, I. M. C.; Staerk, D. Phytochemistry 2015, 116, 246-252 10.1016/j.phytochem.2015.04.004
31. Liao, C.-R.; Kuo, Y.-H.; Ho, Y.-L.; Wang, C.; Yang, C.; Lin, C.-W.; Chang, Y.-S. Molecules 2014, 19, 9515-9534 10.3390/molecules19079515
32. Moradi-Afrapoli, F.; Asghari, B.; Saeidnia, S.; Ajani, Y.; Mirjani, M.; Malmir, M.; Dolatabadi Bazaz, R.; Hadjiakhoondi, A.; Salehi, P.; Hamburger, M.; Yassa, N. Daru, J. Pharm. Sci. 2012, 20, 37 10.1186/2008-2231-20-37
33. Wang, H.; Du, Y.-J.; Song, H.-C. Food Chem. 2010, 123, 6-13 10.1016/j.foodchem.2010.03.088
34. Benavides, A.; Montoro, P.; Bassarello, C.; Piacente, S.; Pizza, C. J. Pharm. Biomed. Anal. 2006, 40, 639-647 10.1016/j.jpba.2005.10.004
35. Ek, S.; Kartimo, H.; Mattila, S.; Tolonen, A. J. Agric. Food Chem. 2006, 54, 9834-9842 10.1021/jf0623687
36. Han, J.-T.; Bang, M.-H.; Chun, O.-K.; Kim, D.-O.; Lee, C.-Y.; Baek, N.-I. Arch. Pharmacal Res. 2004, 27, 390-395 10.1007/BF02980079