α-Glucosidase and α-Amylase Inhibitors from Arcytophyllum thymifolium

Journal of Natural Products

Volumn 79, Issue 8, 2016, Pages 2104-2112

  Milella, Luigi ^a   Milazzo, Stella ^b   De Leo, Marinella ^b   Vera Saltos, Mariela Beatriz ^c   Faraone, Immacolata ^a   Tuccinardi, Tiziano ^b   Lapillo, Margherita ^b   De Tommasi, Nunziatina ^d   Braca, Alessandra ^b  

^a UNIVERSITY OF BASILICATA   (Italy)

^b UNIVERSITY OF PISA   (Italy)

^c UNIVERSIDAD DE LAS FUERZAS ARMADAS ESPE   (Ecuador)

^d UNIVERSITY OF SALERNO   (Italy)

Author keywords

[No Author keywords available]

Indexed keywords

10 O P HYDROXYBENZOYL SCANDOSIDE METHYL ESTER; ACARBOSE; ALPHA GLUCOSIDASE INHIBITOR; AMYLASE INHIBITOR; ANTIDIABETIC AGENT; ASPERULOSIDE; ASPERULOSIDIC ACID; ASPERULOSIDIC ACID METHYL ESTER; CHLOROGENIC ACID; COUMARIN DERIVATIVE; DEACETYL ASPERULOSIDE; DEACETYL ASPERULOSIDIC ACID METHYL ESTER; ERIODICTYOL; FRAXETIN; HEDYOTISCONE A; HEDYOTISCONE B; IRIDOID; IRIDOID ASPERULOSIDIC ACID; KAEMPFEROL 3 O BETA D GLUCOPYRANOSYL (1,2) BETA D GALACTOPYRANOSIDE; NEOCHLOROGENIC ACID METHYL ESTER; QUERCETIN 3 O BETA D GALACTOPYRANOSIDE; QUINIC ACID; RHAMNETIN; SCANDOSIDE; TODDANIN; UNCLASSIFIED DRUG; (2'R)-7-HYDROXY-8-(2',3'-DIHYDROXYISOPENTYL)-6-METHOXYCOUMARIN; (2S)-7-PRENYLOXYERIODICTYOL; 5'-HYDROXY-3'-DEHYDROTODDANIN; 6-DEMETHYL-5'-HYDROXY-3'-DEHYDROTODDANIN; ALPHA GLUCOSIDASE; AMYLASE; ENZYME INHIBITOR; FLAVANONE DERIVATIVE; FLAVONOID; GLYCOSIDASE INHIBITOR; QUERCETIN;

ANTIDIABETIC ACTIVITY; ARCYTOPHYLLUM THYMIFOLIUM; ARTICLE; CARBON NUCLEAR MAGNETIC RESONANCE; CONTROLLED STUDY; DRUG ISOLATION; DRUG STRUCTURE; ENZYME ACTIVE SITE; ENZYME INHIBITION; HETERONUCLEAR MULTIPLE BOND CORRELATION; MEDICINAL PLANT; NONHUMAN; PROTON NUCLEAR MAGNETIC RESONANCE; ALGORITHM; ANALOGS AND DERIVATIVES; ANTAGONISTS AND INHIBITORS; CHEMICAL STRUCTURE; CHEMISTRY; ECUADOR; ISOLATION AND PURIFICATION; METABOLISM; NUCLEAR MAGNETIC RESONANCE; RUBIACEAE;

ACARBOSE; ALGORITHMS; ALPHA-AMYLASES; ALPHA-GLUCOSIDASES; COUMARINS; ECUADOR; ENZYME INHIBITORS; FLAVANONES; FLAVONOIDS; GLYCOSIDE HYDROLASE INHIBITORS; HYPOGLYCEMIC AGENTS; IRIDOIDS; MOLECULAR STRUCTURE; NUCLEAR MAGNETIC RESONANCE, BIOMOLECULAR; QUERCETIN; RUBIACEAE;

EID: 84984688832     PISSN: 01633864     EISSN: 15206025     Source Type: Journal    
DOI: 10.1021/acs.jnatprod.6b00484     Document Type: Article

References (50)

1. Mena, V. P. Mem. New York Bot. Gard. 1990, 60, 1-26
2. Sklenář, P.; Balslev, H. Flora 2007, 202, 50-61 10.1016/j.flora.2006.03.002
3. Monigatti, M.; Bussmann, R. W.; Weckerle, C. S. J. Ethnopharmacol. 2013, 145, 450-464 10.1016/j.jep.2012.10.066
4. De Feo, V.; della Valle, C.; De Simone, F.; Pizza, C. Ann. Chim. 1992, 82, 476-486
5. Saltos, M. B. V.; Puente, B. F. N.; Faraone, I.; Milella, L.; De Tommasi, N.; Braca, A. Phytochem. Lett. 2015, 14, 45-50 10.1016/j.phytol.2015.08.018
6. Saltos, M. B. V.; Puente, B. F. N.; Milella, L.; De Tommasi, N.; Dal Piaz, F.; Braca, A. Planta Med. 2015, 81, 1056-1064 10.1055/s-0035-1545928
7. Murali, R.; Srinivasan, S.; Ashokkumar, N. Biochimie 2013, 95, 1848-1854 10.1016/j.biochi.2013.06.013
8. Cao, H.; Chen, X. Anti-Cancer Agents Med. Chem. 2012, 12, 929-939 10.2174/187152012802650110
9. Manaharan, T.; Teng, L. L.; Appleton, D.; Ming, C. H.; Masilamani, T.; Palanisamy, U. D. Food Chem. 2011, 129, 1355-1361 10.1016/j.foodchem.2011.05.041
10. Kim, K. E.; Ko, K. H.; Heo, R. W.; Yi, C.; Shin, H. J.; Kim, J. Y.; Park, J. H.; Nam, S.; Kim, H.; Roh, G. S. J. Med. Food 2016, 19, 290-299 10.1089/jmf.2015.3527
11. Miura, T.; Nishiyama, Y.; Ichimaru, M.; Moriyasu, M.; Kato, A. Biol. Pharm. Bull. 1996, 19, 160-161 10.1248/bpb.19.160
12. Giang, V. H.; Ban, N. K.; Nhiem, N. X.; Kiem, P.; Minh, C.; Anh, H. L. T.; Yen, P. H.; Tai, B. H.; Cuong, N. X.; Nam, N. H. Bull. Korean Chem. Soc. 2013, 34, 1555-1558 10.5012/bkcs.2013.34.5.1555
13. McCarty, M. F. Med. Hypotheses 2005, 64, 848-853 10.1016/j.mehy.2004.03.037
14. Wardrop, D. J.; Waidyarachchi, S. L. Nat. Prod. Rep. 2010, 27, 1431-1468 10.1039/b914958a
15. Sels, J. P. J. E.; Huijberts, M. S. P.; Wolffenbuttel, B. H. R. Expert Opin. Pharmacother. 1999, 1, 149-156 10.1517/14656566.1.1.149
16. Teng, H.; Chen, L. Crit. Rev. Food Sci. Nutr. 2016, 10.1080/10408398.2015.1129309.
17. Amaro-Luis, J. M.; Massanet, G. M.; Pando, E.; Rodriguez-Luis, F.; Zubia, E. Planta Med. 1990, 56, 304-306 10.1055/s-2006-960965
18. Tsai, I. L.; Wun, M. F.; Teng, C. M.; Ishikawa, T.; Chen, I. S. Phytochemistry 1998, 48, 1377-1382 10.1016/S0031-9422(97)00678-X
19. Di Bari, L.; Pescitelli, G.; Pratelli, C.; Pini, D.; Salvadori, P. J. Org. Chem. 2001, 66, 4819-4825 10.1021/jo010136v
20. Garo, E.; Wolfender, J. L.; Hostettmann, K.; Hiller, W.; Antus, S.; Mavi, S. Helv. Chim. Acta 1998, 81, 754-763 10.1002/hlca.19980810325
21. Slade, D.; Ferreira, D.; Marais, J. P. Phytochemistry 2005, 66, 2177-2215 10.1016/j.phytochem.2005.02.002
22. Otsuka, H.; Yoshimura, K.; Yamasaki, K.; Cantoria, M. C. Chem. Pharm. Bull. 1991, 39, 2049-2052 10.1248/cpb.39.2049
23. Mondon, A.; Callsen, H. Chem. Ber. 1975, 108, 2005-2020 10.1002/cber.19751080620
24. Chen, Y. H.; Chang, F. R.; Wu, C. C.; Yen, M. H.; Liaw, C. C.; Huang, H. C.; Kuo, Y. H.; Wu, Y. C. Planta Med. 2006, 72, 75 10.1055/s-2005-873178
25. Okuyama, E.; Okamoto, Y.; Yamazaki, M.; Satake, M. Chem. Pharm. Bull. 1996, 44, 333-336 10.1248/cpb.44.333
26. De Almeida, A.; Miranda, M.; Simoni, I.; Wigg, M.; Lagrota, M.; Costa, S. Phytother. Res. 1998, 12, 562-567 10.1002/(SICI)1099-1573(199812)12:8<562::AID-PTR356>3.0.CO;2-6
27. Agrawal, P. K. Carbon-13 NMR of Flavonoids; Elsevier: Amsterdam, 1989; p 13.
28. Han, Y.; Nishibe, S.; Noguchi, Y.; Jin, Z. Phytochemistry 2001, 58, 577-580 10.1016/S0031-9422(01)00273-4
29. Demirezer, L. Ö.; Gürbüz, F.; Güvenalp, Z.; Ströch, K.; Zeeck, A. Turk. J. Chem. 2006, 30, 525-534
30. Kim, D.-H.; Lee, H.-J.; Oh, Y.-H.; Kim, M.-J.; Kim, S.-H.; Jeong, T.-S.; Baek, N.-I. Arch. Pharmacal Res. 2005, 28, 1156-1160 10.1007/BF02972979
31. Chaudhuri, R. K.; Afifi-Yazar, F. U.; Sticher, O. Tetrahedron 1980, 36, 2317-2326 10.1016/0040-4020(80)80128-1
32. Zhu, X.; Dong, X.; Wang, Y.; Ju, P.; Luo, S. Helv. Chim. Acta 2005, 88, 339-342 10.1002/hlca.200590017
33. Iwai, K.; Kishimoto, N.; Kakino, Y.; Mochida, K.; Fujita, T. J. Agric. Food Chem. 2004, 52, 4893-4898 10.1021/jf040048m
34. Yamamoto, K.; Miyake, H.; Kusunoki, M.; Osaki, S. FEBS J. 2010, 277, 4205-4214 10.1111/j.1742-4658.2010.07810.x
35. Fiser, A.; Do, R. K.; Sali, A. Protein Sci. 2000, 9, 1753-1773 10.1110/ps.9.9.1753
36. Laskowski, R. A.; Macarthur, M. W.; Moss, D. S.; Thornton, J. M. J. Appl. Crystallogr. 1993, 26, 283-291 10.1107/S0021889892009944
37. Morris, G. M.; Huey, R.; Lindstrom, W.; Sanner, M. F.; Belew, R. K.; Goodsell, D. S.; Olson, A. J. J. Comput. Chem. 2009, 30, 2785-2791 10.1002/jcc.21256
38. Poli, G.; Gelain, A.; Porta, F.; Asai, A.; Martinelli, A.; Tuccinardi, T. J. Enzyme Inhib. Med. Chem. 2016, 1-7 10.3109/14756366.2015.1079184
39. Kollman, P. A.; Massova, I.; Reyes, C.; Kuhn, B.; Huo, S.; Chong, L.; Lee, M.; Lee, T.; Duan, Y.; Wang, W.; Donini, O.; Cieplak, P.; Srinivasan, J.; Case, D. A.; Cheatham, T. E., 3rd Acc. Chem. Res. 2000, 33, 889-897 10.1021/ar000033j
40. Tuccinardi, T.; Manetti, F.; Schenone, S.; Martinelli, A.; Botta, M. J. Chem. Inf. Model. 2007, 47, 644-655 10.1021/ci6004383
41. Dal Piaz, F.; Vassallo, A.; Temraz, A.; Cotugno, R.; Belisario, M. A.; Bifulco, G.; Chini, M. G.; Pisano, C.; De Tommasi, N.; Braca, A. J. Med. Chem. 2013, 56, 1583-1595 10.1021/jm301398y
42. Dekdouk, N.; Malafronte, N.; Russo, D.; Faraone, I.; De Tommasi, N.; Ameddah, S.; Severino, L.; Milella, L. Evid.-Based Complement. Alternat. Med. 2015, 2015, 684925 10.1155/2015/684925
43. Gasteiger, E.; Gattiker, A.; Hoogland, C.; Ivanyi, I.; Appel, R. D.; Bairoch, A. Nucleic Acids Res. 2003, 31, 3784-3788 10.1093/nar/gkg563
44. Altschul, S. F.; Madden, T. L.; Schaffer, A. A.; Zhang, J.; Zhang, Z.; Miller, W.; Lipman, D. J. Nucleic Acids Res. 1997, 25, 3389-3402 10.1093/nar/25.17.3389
45. Berman, H. M.; Westbrook, J.; Feng, Z.; Gilliland, G.; Bhat, T. N.; Weissig, H.; Shindyalov, I. N.; Bourne, P. E. Nucleic Acids Res. 2000, 28, 235-242
46. Thompson, J. D.; Higgins, D. G.; Gibson, T. J. Nucleic Acids Res. 1994, 22, 4673-4680 10.1093/nar/22.22.4673
47. Macromodel, version 9.7; Schrödinger, Inc: Portland, OR, 2009.
48. Case, D. A.; Berryman, J. T.; Betz, R. M.; Cerutti, D. S.; T. E, C., III; Darden, T. A.; Duke, R. E.; Giese, T. J.; Gohlke, H.; Goetz, A. W.; Homeyer, N.; Izadi, S.; Janowski, P.; Kaus, J.; Kovalenko, A.; Lee, T. S.; LeGrand, S.; Li, P.; Luchko, T.; Luo, R.; Madej, B.; Merz, K. M.; Monard, G.; Needham, P.; Nguyen, H.; Nguyen, H. T.; Omelyan, I.; Onufriev, A.; Roe, D. R.; Roitberg, A.; Salomon-Ferrer, R.; Simmerling, C. L.; Smith, W.; Swails, J.; Walker, R. C.; Wang, J.; Wolf, R. M.; Wu, X.; York, D. M.; Kollman, P. A. AMBER, version 14; University of California: San Francisco, CA, 2015.
49. Yamamoto, K.; Miyake, H.; Kusunoki, M.; Osaki, S. FEBS J. 2010, 277, 4205-4214 10.1111/j.1742-4658.2010.07810.x
50. York, D. M.; Darden, T. A.; Pedersen, L. G. J. Chem. Phys. 1993, 99, 8345-8348 10.1063/1.465608