Protein tyrosine phosphatase 1B (PTP1B) inhibitory activity and glucosidase inhibitory activity of compounds isolated from Agrimonia pilosa

Pharmaceutical Biology

Volumn 54, Issue 3, 2016, Pages 474-480

  Na, Braham ^a   Nguyen, Phi Hung ^a   Zhao, Bing Tian ^a   Vo, Quoc Hung ^a   Min, Byung Sun ^a   Woo, Mi Hee ^a  

^a Catholic University of Daegu   (South Korea)

Author keywords

Flavonoid glycosides; glucosidase inhibitors; PTP1B inhibitors; triterpenoids

Indexed keywords

4 NITROPHENYL PHOSPHATE; ACETIC ACID ETHYL ESTER; AGRIMONIA PILOSA EXTRACT; ALCOHOL; ALPHA GLUCOSIDASE; ANTIDIABETIC AGENT; APIGENIN 7 O BETA DEXTRO GLUCURONIDE 6' METHYL ESTER; BUTANOL; DICHLOROMETHANE; FLAVONOID; KAEMPFEROL; KAEMPFEROL 3 O ALPHA LEVO RHAMNOSIDE; METHYL 2 HYDROXYL TRICOSANOATE; PALMITIC ACID; PROTEIN TYROSINE PHOSPHATASE 1B; QUERCETIN 3 O BETA DEXTRO GLYCOSIDE; QUERCETIN 7 O BETA DEXTRO GLYCOSIDE; SITOSTEROL; TORMENTIC ACID; TRILIROSIDE; TRITERPENOID; UNCLASSIFIED DRUG; URSOLIC ACID; WATER; ENZYME INHIBITOR; GLYCOSIDASE INHIBITOR; HERBACEOUS AGENT; PTPN1 PROTEIN, HUMAN;

AGRIMONIA; ANTIDIABETIC ACTIVITY; ARTICLE; CHROMATOGRAPHY; CONTROLLED STUDY; DRUG EFFECT; DRUG MECHANISM; DRUG POTENCY; DRUG SCREENING; DRUG STRUCTURE; ENZYME ACTIVITY; ENZYME INHIBITION; ENZYME SUBSTRATE; IC50; IN VITRO STUDY; PHYSICAL CHEMISTRY; ANTAGONISTS AND INHIBITORS; DOSE RESPONSE; HUMAN; ISOLATION AND PURIFICATION; METABOLISM; PLANT STRUCTURES;

AGRIMONIA; DOSE-RESPONSE RELATIONSHIP, DRUG; DRUGS, CHINESE HERBAL; ENZYME INHIBITORS; GLYCOSIDE HYDROLASE INHIBITORS; HUMANS; PLANT COMPONENTS, AERIAL; PROTEIN TYROSINE PHOSPHATASE, NON-RECEPTOR TYPE 1;

EID: 84956698146     PISSN: 13880209     EISSN: 17445116     Source Type: Journal    
DOI: 10.3109/13880209.2015.1048372     Document Type: Article

References (43)

1. Ahmad F, Azevedo JJ, Cortright R, et al. (1997a). Alterations in skeleton muscle protein tyrosine phosphatase activity and expression in insulin-resistant human obesity and diabetes. J Clin Invest 100: 449-58
2. Ahmad F, Considine RV, Bauer TL, et al. (1997b). Improved sensitivity to insulin in obese subjects following weight loss is accompanied by reduced protein tyrosine phosphatase in adipose tissue. Metabolism 46: 1140-5
3. An RB, Kim HC, Jeong GS, et al. (2005). Constituents of the aerial parts of Agrimonia pilosa. Nat Prod Sci 11: 196-8
4. 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: 7101-8
5. Bajaj R, Chang CJ, McLaughlin JL, et al. (1986). Tiliroside from the seeds of Eremocarpus setigerus. J Nat Prod 49: 1174-5
6. 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: 223-33
7. 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: 129-34
8. Burke TR, Zhang ZY. (1998). Protein-tyrosine phosphatases: Structure, mechanism, and inhibitor discovery. Biopolymers 47: 225-41
9. 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: 384-9
10. Cui L, Lee HS, Ndinteh DT, et al. (2010). New prenylated flavanones from stem bark of Erythrina abyssinica with PTP1B inhibitory activity. Planta Med 76: 713-18
11. Danaei G, Finucane MM, Lu Y, et al. (2011). National, regional, and global trends in fasting plasma glucose and diabetes prevalence since 1980: Systematic analysis of health examination surveys and epidemiological studies with 370 country-years and 2.7 million participants. Lancet 378: 31-40
12. 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: 1544-8
13. Erratum. (2013). Economic costs of diabetes in the U.S. in 2012. Diabetes Care 36: 1033-46
14. Fang L, Xiaoyu B, Yongzhi H. (2012). Chemical constituents of Herba Agrimoniae. Zhongcaoyao 43: 851-5
15. Goldstein BJ, Bitter-Kowalczyk A, White MF, Harbeck M. (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. J Biol Chem 275: 4283-9
16. Gong CG, Zhang GG, Wang XI, Lei YH. (2006). Experimental studies of anti-inflammatory and analgesic effects of extract from Herba Agrimoniae. J Pharm Pract 6: 339-41
17. Hamaguchi T, Sudo T, Osada H. (1995). RK-682, a potent inhibitor of tyrosine phosphatase, arrested the mammalian cell cycle progression at G1phase. FEBS Lett 372: 54-8
18. Hong G, Dai YH, Liu PX, et al. (2008). Advances in research on chemical constituents and pharmacological activities of Agrimonia pilosa. Pharm Care Res 8: 362-6
19. Jung CH. (2010). Inhibitory effect of Agrimonia pilosa Ledeb. On inflammation by suppression of iNOS and ROS production. Immunol Invest 39: 159-70
20. Jung M, Park M. (2007). Acetylcholinesterase inhibition by flavonoids from Agrimonia pilosa. Molecules 12: 2130-9
21. Kato H, Li W, Koike M, et al. (2010). Phenolic glycosides from Agrimonia pilosa. Phytochemistry 71: 1925-9
22. 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: 5479-89
23. Kumar S, Narwal S, Kumar V, Prakash O. (2011). αr;-Glucosidase inhibitors from plants: A natural approach to treat diabetes. Pharmacogn Rev 5: 19-29
24. Li T, Zhang XD, Song YW, Liu JW. (2005). A microplate-based screening method for alpha-glucosidase inhibitors. Chin J Clin Pharmacol Ther 10: 1128-34
25. Liljebris C, Larsen SD, Ogg D, et al. (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: 1785-98
26. Lin YL, Wang CN, Shiao YJ, et al. (2003). Benzolignanoid and polyphenols from Origanum vulgare. J Chin Chem Soc 50: 1079-83
27. Liu PY, Yulei Z, Liqin D, et al. (2008). Studies on isolation and identification of flavonoids in herbs of Agrimonia pilosa. Zhongguo Zhongyao Zazhi 33: 2925-8
28. Miyamoto K, Koshiura R, Ikeya Y, Taguchi H. (1985). Isolation of agrimoniin, an anti-tumour constituent, from the roots of Agrimonia pilosa LEDEB. Chem Pharm Bull 33: 3977-81
29. Miyamoto K, Kishi N, Koshiura R. (1987). Antitumor effect of agrimoniin, a tannin of Agrimonia pilosa Ledeb. On transplantable rodent tumors. Jpn J Pharmacol 43: 187-95
30. Mohamed S, Mohamed AEA, Nabiel AMS. (1997). Flavonoids of four Cleome and three Capparis species. Biochem Syst Ecol 25: 161-6
31. Moller DE. (2001). New drug targets for type 2 diabetes and the metabolic syndrome. Nature 414: 821-7
32. 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: 3378-83
33. Nguyen PH, Nguyen TNA, Kang KW, et al. (2010). Prenylated pterocarpans as bacterial neuraminidase inhibitors. Bioorg Med Chem 18: 3335-44
34. Park EJ, Oh H, Kang TH, et al. (2004). An isocoumarin with hepatoprotective activity in HepG2 and primary hepatocytes from Agrimonia pilosa. Arch Pharm Res 27: 944-6
35. Shin W, Lee K, Park M, Seong B. (2010). Broad-spectrum antiviral effect of Agrimonia pilosa extract on influenza viruses. Microbiol Immunol 54: 11-19
36. Song LL, Li D, Zhang MX, et al. (2013). Triliroside isolated from Agrimonia pilosa Ledeb. Enhanced adiponectin secretion and GLUT4 translocation in 3T3-L1 cells. Lat Am J Pharm 32: 524-30
37. 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: 2911-22
38. 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: 18318-26
39. 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: 5973-80
40. Yamada K, Matsubara R, Kaneko M, et al. (2001). Constituents of Holothuroidea. 10. Isolation and structure of a biologically active ganglioside molecular species from the sea cucumber Holothuria leucospilota. Chem Pharm Bull 49: 447-52
41. Zhang S, Zhang ZY. (2007). PTP1B as a drug target: Recent developments in PTP1B inhibitor discovery. Drug Discov Today 12: 373-81
42. Zhang ZY, Lee SY. (2003). PTP1B inhibitors as potential therapeutics in the treatment of type 2 diabetes and obesity. Expert Opin Investig Drugs 12: 223-33
43. Zhu L, Tan J, Wang B, et al. (2009). Antioxidant activities of aqueous extract from Agrimonia pilosa LEDEB. And its fractions. Chem Biodivers 6: 1716-26