Chemical constituents of Euonymus alatus (Thunb.) Sieb. and their PTP1B and α-glucosidase inhibitory activities

Phytotherapy Research

Volumn 29, Issue 10, 2015, Pages 1540-1548

  Jeong, Su Yang ^a   Nguyen, Phi Hung ^a   Zhao, Bing Tian ^a   Ali, Md Yousof ^b   Choi, Jae Sue ^b   Min, Byung Sun ^a   Woo, Mi Hee ^a  

^a Catholic University of Daegu   (South Korea)

^b Pukyong National University   (South Korea)

Author keywords

Euonymus alatus; flavanol; PTP1B inhibitors; triterpenoids; glucosidase

Indexed keywords

3 HYDROXYCOUMARINFLAVANOL DERIVATIVE; ACARBOSE; ALPHA GLUCOSIDASE; ALPHA GLUCOSIDASE INHIBITOR; EUONYMUS ALATUS EXTRACT; FLAVONOID GLYCOSIDE; PHENOL DERIVATIVE; PLANT EXTRACT; PROTEIN TYROSINE PHOSPHATASE 1B; PROTEIN TYROSINE PHOSPHATASE 1B INHIBITOR; TRITERPENOID; UNCLASSIFIED DRUG; ANTIDIABETIC AGENT; ENZYME INHIBITOR; FLAVONOID;

ARTICLE; COMPETITIVE INHIBITION; CONTROLLED STUDY; DRUG ACTIVITY; DRUG ISOLATION; DRUG POTENCY; DRUG STRUCTURE; ENZYME INHIBITION; EUONYMUS; EUONYMUS ALATUS; IC50; INHIBITION KINETICS; MASS SPECTROMETRY; NONCOMPETITIVE INHIBITION; NONHUMAN; NUCLEAR MAGNETIC RESONANCE SPECTROSCOPY; PHYTOCHEMISTRY; ANTAGONISTS AND INHIBITORS; CHEMISTRY; METABOLISM;

ALPHA-GLUCOSIDASES; ENZYME INHIBITORS; EUONYMUS; FLAVONOIDS; HYPOGLYCEMIC AGENTS; MAGNETIC RESONANCE SPECTROSCOPY; PHENOLS; PROTEIN TYROSINE PHOSPHATASE, NON-RECEPTOR TYPE 1;

EID: 84943515654     PISSN: 0951418X     EISSN: 10991573     Source Type: Journal    
DOI: 10.1002/ptr.5411     Document Type: Article

References (55)

1. Adisakwattana S, Pongsuwan J, Wungcharoen C, Yibchok-anun S,. 2013. In vitro effects of cinnamic acid derivatives on protein tyrosine phosphatase 1B. J Enzyme Inhib Med Chem 28: 1067-1072.
2. Ahmad F, Considine RV, Bauer TL, Ohannesian JP, Marco CC, Goldstein BJ,. 1997. Improved sensitivity to insulin in obese subjects following weight loss is accompanied by reduced protein tyrosine phosphatase in adipose tissue. Metabolism 46: 1140-1145.
3. 13C-NMR spectra of sterols and triterpene alcohols. Yukagak 36: 301-319.
4. Akihisa T, Yamamoto K, Tamura T, et al., 1992. Triterpenoid ketones from lingnania chungii Mcclure: arborinone, friedelin and glutinone. Chem Pharm Bull 40: 789-791.
5. Andersen HS, Iversen LF, Jeppensen CB, et al., 2000. 2-(Oxalylamino)benzoic acid is a general competitive inhibitor of protein tyrosine phosphatases. J Biol Chem 275: 7101-7108.
6. Arora KK, Parakashareddy J, Pedireddi VR,. 2005. Pyridine mediated supramolecular assemblies of 3,5-dinitro substituted benzoic acid, benzamide and benzonitrile. Tetrahedron 61: 10793-10800.
7. Bailly F, Maurin C, Teissier E, Vezina H, Cotelle P,. 2004. Antioxidant properties of 3-hydroxycoumarin derivatives. Bioorg Med Chem 12: 5611-5618.
8. Benavides A, Montoro P, Bassarello C, Piacente S, Pizza C,. 2006. Catechin derivatives in Jatropha macrantha stems: characterisation and LC/ESI/MS/MS quali-quantitative analysis. J Pharm Biomed Anal 40: 639-647.
9. Bialy L, Waldmann H,. 2003. Inhibitors of protein PTP1B inhibitors as potential therapeutics in the treatment of type 2 diabetes and obesity. Expert Opin Investig Drugs 12: 223-233.
10. Burke TR, Zhang ZY,. 1998. Protein-tyrosine phosphatases: structure, mechanism, and inhibitor discovery. Biopolymers 47: 225-241.
11. Burke TR, Kole HK, Roller PP,. 1994. Potent inhibition of insulin receptor dephosphorylation by a hexamer peptide containing the phosphotyrosyl mimetic F2Pmp. Biochem Biophys Res Commun 204: 129-134.
12. Chen H, Cong LN, Li Y, et al., 1999. A phosphotyrosyl mimetic peptide reverses impairment of insulin-stimulated translocation of GLUT4 caused by overexpression of PTP-1B in rat adipose cells. Biochemistry 38: 384-389.
13. Cui L, Lee HS, Ndinteh DT, et al., 2010. New prenylated flavones from Erythrina abyssinica with protein tyrosine phosphatase 1B (PTP1B) inhibitory activity. Planta med 76: 713-718.
14. Dai Z, Wang F, Wang GL, Lin RC,. 2006. Studies on chemical constituents of Balanophora spicata. China J Chinese Materia Medica 31: 1798-1800.
15. Das B, Kashinatham A,. 1997. Studies on phytochemicals: Park XVII-phenolics from the roots of Jatropha gossypifolia. Indian J Chem 36B: 1077-1078.
16. De Souza ADL, Da Rocha AFI, Pingeiro MLB, et al., 2001. Constitutes quimicos de Gustavia augusta L. Quim Nova 24: 439-422.
17. Donovan JL, Luthria DL, Stremple P, Waterhouse AL,. 1999. Analysis of (+)-catechin, (-)-epicatechin and their 3'- and 4'-O-methylated analogs. A comparison of sensitive methods. J Chromatogr B Biomed Sci Appl 726: 277-283.
18. Durust N, Ozden S, Umur E, Durust Y, Ducukislamoglu M,. 2001. The isolation of carboxylic acids from the flowers of Delphinium formosum. Turk J Chem 25: 93-97.
19. Elchebly M, Payette P, Michaliszyn E, et al., 1999. Increased insulin sensitivity and obesity resistance in mice lacking the protein tyrosine phophatase-1B gene. Science 283: 1544-1548.
20. Friedman JM,. 2003. A war on obesity, not the obese. Science 299: 856-858.
21. Fuchino H, Satoh T, Tanaka N,. 1995. Chemical evaluation of Betula species in Japan. I. Constituents of Betula ermanii. Chem Pharm Bull 43: 1937-1942.
22. Gaspar EMM, Neves HJC,. 1993. Steroidal constituents from mature wheat straw. Phytochemistry 34: 523-527.
23. Gokhale KM,. 2011. New method for synthesis of 3-(4-hydroxy-3-methoxyphenyl) prop-2-enoic acid and 1-feruloyl-β-D-glucose. Int J Pharm Phytopharm Res 1: 17-22.
24. Goldstein BJ, Bitter-Kowalczyk A, White MF, Harbeck MJ,. 2000. Tyrosine dephosphorylation and deactivation of insulin receptor substrate-1 by protein tyrosine phosphatase 1B. Possible facilitation by the formation of a ternary complex with the GRB2 adaptor protein. Biol Chem 275: 4283-4289.
25. Hamaquchi T, Sudo T, Osada H., 1995. RK-682, a potent inhibitor of tyrosine phosphatase, arrested the mammalian cell cycle prograssion at G1phase. FEBS Lett 372: 54-58.
26. He RJ, Yu ZH, Zhang RY, Zhang ZY,. 2014. Protein tyrosine phosphatases as potential therapeutic targets. Acta Pharm Sin 35: 1227-1246.
27. Hossain P, Kawar B, El Nahas M,. 2007. Obesity and diabetes in the developing world-a growing challenge. N Engl J Med 356: 213-215.
28. Huang KC,. 1998. The Pharmacology of Chinese Herbs, 2nd edn. CRC Press: New York.
29. Ingham JL, Markham KR, Dziedzic SZ, Pope GS,. 1986. Puerarin 6″-O-β-apiofuranoside, a C-glycosylisoflavone O-glycoside from Pueraria mirifica. Phytochemistry 25: 1772-1775.
30. Kim YH,. 1999. Isolation of acylated steryl glycosides from the legumes of Albizzia julibrissin. Kor J Pharmacogn 30: 290-294.
31. Klaman LD, Boss O, Peroni OD, et al., 2000. Increased energy expenditure, decreased adiposity, and tissue-specific insulin sensitivity in protein tyrosine phosphatase 1B-deficient mice. Mol Cell Biol 20: 5479-5489.
32. Koul S, Razdan TK, Andotra CS, et al., 2000. Koelpinin-A, B and C-three triterpenoids from Koelpinia linearis. Phytochemistry 53: 305-309.
33. Lee IR, Jeong HK,. 1992. Isolation of triterpenoid and phenylpropanoid from Codonopsis ussuriensis. Arch Pharm Res 15: 289-291.
34. Lee SK, Hwang JY, Song JH, et al., 2007. Inhibitory activity of Euonymus alatus against alpha-glucosidase in vitro and in vivo. Nutr Res Pract 1: 184-188.
35. Lewinsohn E, Berman E, Mazur Y, Gressel J,. 1986. Glucosylation of exogenous flavanones by grapefruit (Citrus paradisi) cell vultures. Phytochemistry 25: 2531-2535.
36. Li T, Zhang XD, Song YW, Liu JW,. 2005. A microplate-based screening method for alpha-glucosidase inhibitors. Chin J Clin Pharmacol Ther 10: 1128-1134.
37. Liljebris C, Larsen SD, Ogg D, Palazuk BJ, Bleasedale JE,. 2002. Investigation of potential bioisosteric replacements for the carboxyl groups of peptidomimetic inhibitors of protein tyrosine phosphatase 1B: identification of a tetrazole-containing inhibitor with cellular activity. J Med Chem 45: 1785-1798.
38. Mitase T, Fugushima S, Akitama Y,. 1984. Studies on the constituents of Hedysarum polybotrys Hand.-Mazz. Chem Pharm Bull 32: 3267-3270.
39. Moller DE,. 2001. New drug targets for type 2 diabetes and the metabolic syndrome. Nature 414: 821-827.
40. Na MK, Kim BY, Osada H, Ahn JS,. 2009. Inhibition of protein tyrosine phosphatase 1B by lupeol and lupenone isolated from Sorbus commixta. J Enzyme Inhib Med Chem 24: 1056-1059.
41. Nguyen PH, Nguyen TNA, Kang KW, et al., 2010. Prenylated pterocarpans as bacterial neuraminidase inhibitors. Bioorg Med Chem 18: 3335-3344.
42. Nguyen PH, Dao TT, Kim JY, et al., 2011. New 5-deoxyflavonoids and their inhibitory effects on protein tyrosine phosphatase 1B (PTP1B) activity. Bioorg Med Chem 19: 3378-3383.
43. Oh BK, Mun JH, Seo HW, et al., 2011. Euonymus alatus extract attenuates LPS-induced NF-κB activation via IKKβ inhibition in RAW 264.7 cells. J Ethnopharmacol 134: 288-293.
44. Park SH, Ko SK, Chung SH,. 2005. Euonymus alatus prevents the hyperglycemia and hyperlipidemia induced by high-fat diet in ICR mice. J Ethnopharmacol 102: 326-335.
45. Porter LJ, Harborne JB,. 1994. In the Flavonoids-Advances in Research Since 1986. Chapman & Hall: London.
46. Slade D, Ferreira D, Marais JPJ,. 2005. Circular dichroism, a powerful tool for the assessment of absolute configuration of flavonoids. Phytochemistry 66: 2177-2215.
47. Su K, Gong M, Zhou J, Deng S, Iribarren AM, Pomilio AB,. 2009. Components of Bauhinia candicans. Int J Chem 1: 77-82.
48. Tewari N, Tiwari VK, Mishra RC, et al., 2003. Synthesis and bioevaluation of glycosyl ureas as alpha-glucosidase inhibitors and their effect on mycobacterium. Bioorg Med Chem 11: 2911-2922.
49. Ullah N, Ahmad S, Malik A,. 1999. Phenylpropanoid Glycosides from Daphne oleoides. Chem Pharm Bull 47: 114-115.
50. Venable CL, Frevert EU, Kim YB, et al., 2000. Overexpression of protein tyrosine phosphatase 1B in adipocytes inhibits insulin-stimulated phosphoinositide 3-kinase activity without altering glucose transport or Akt/protein kinase B activation. J Biol Chem 275: 18318-18326.
51. Wiesmann C, Barr KJ, Kung J, et al., 2004. Allosteric inhibition of protein tyrosine phosphatase 1B. Nat Struct Mol Biol 11: 730-737.
52. Wilhelm, A, 2008. Ms Thesis, University of the Free State Bloemfontein.
53. Wu X, Hoffstedt J, Deeb W, et al., 2001. Depot-specific variation in protein tyrosine phosphatases activities in human omental and subcutaneous adipose tissue: a potential contribution to differential insulin sensitivity. J Clin Endocrinol Metab 86: 5973-5980.
54. Zhang S, Zhang ZY,. 2007. PTP1B as a drug target: recent developments in PTP1B inhibitor discovery. Drug Discov Today 12: 373-381.
55. Zimmet P, Alberti KG, Shaw J,. 2001. Global and societal implications of the diabetes epidemic. Nature 414: 782-787.