PTP1B inhibitory effects of tridepside and related metabolites isolated from the Antarctic lichen Umbilicaria antarctica

Journal of Enzyme Inhibition and Medicinal Chemistry

Volumn 24, Issue 5, 2009, Pages 1133-1137

  Seo, Changon ^a   Choi, Yun Hyeok ^a   Ahn, Jong Seog ^b   Yim, Joung Han ^c   Lee, Hong Kum ^c   Oh, Hyuncheol ^a  

^a Silla University   (South Korea)

^b Korea Research Institute of Bioscience and Biotechnology (KRIBB)   (South Korea)

^c Korea Research Institute of Ships and Ocean Engineering   (South Korea)

Author keywords

Antarctic lichen; Lichen metabolites; Non competitive inhibitor; Protein tyrosine phosphatase 1B (PTP1B); Umbilicaria antarctica

Indexed keywords

GYROPHORIC ACID; LECANORIC ACID; METHANOL; ORSELLINIC ACID METHYL ESTER; PLANT EXTRACT; PROTEIN TYROSINE PHOSPHATASE 1B; TRIDEPSIDE; UNCLASSIFIED DRUG;

ARTICLE; BIOASSAY; CONCENTRATION RESPONSE; CONTROLLED STUDY; DRUG ISOLATION; DRUG PURIFICATION; DRUG STRUCTURE; DRUG TARGETING; ENZYME ACTIVITY; ENZYME INHIBITION; FRACTIONATION; HUMAN; IC 50; LICHENS; MASS SPECTROMETRY; NON INSULIN DEPENDENT DIABETES MELLITUS; OBESITY; PRIORITY JOURNAL; PROTON NUCLEAR MAGNETIC RESONANCE; UMBILICARIA ANTARCTICA;

ANTARCTIC REGIONS; BENZOIC ACIDS; DOSE-RESPONSE RELATIONSHIP, DRUG; ENZYME ACTIVATION; ENZYME INHIBITORS; LICHENS; MAGNETIC RESONANCE SPECTROSCOPY; MASS SPECTROMETRY; PLANT EXTRACTS; PROTEIN TYROSINE PHOSPHATASE, NON-RECEPTOR TYPE 1; RESORCINOLS; SALICYLATES;

UMBILICARIA ANTARCTICA;

EID: 74549186582     PISSN: 14756366     EISSN: 14756374     Source Type: Journal    
DOI: 10.1080/14756360802667811     Document Type: Article

References (28)

1. Kenner KA, Anyanwu E, Olefsky JM, Kusari J. Protein-tyrosine phosphatase 1B is a negative regulator of insulin- and insulinlike growth factor-I-stimulated signaling. J Biol Chem 1996; 271: 19810-19816.
2. Seely BL, Staubs PA, Reichart DR, Berhanu P, Milarski KL, Saltiel AR, Kusari J, Olefsky JM. Protein tyrosine phosphatase 1B interacts with the activated insulin receptor. Diabetes 1996; 45: 1379-1385.
3. Calera MR, Vallega G, Pilch PF. Dynamics of protein-tyrosine phosphatases in rat adipocytes. J Biol Chem 2000; 275: 6308-6312.
4. Ahmad F, Azevedo JL, Cortright R, Dohm GL, Goldstein BJ. Alterations in skeletal muscle protein-tyrosine phosphatase activity and expression in insulin-resistant human obesity and diabetes. J Clin Invest 1997; 100: 449-458.
5. Elchebly M, Payette P, Michaliszyn E, Cromlish W, Collins S, Loy A L, Normandin D, Cheng A, Himms-Hagen J, Chan CC, Ramachandran C, Gresser MJ, Tremblay ML, Kennedy BP. Increased insulin sensitivity and obesity resistance in mice lacking the protein tyrosine phosphatase-1B gene. Science 1999; 283: 1544-1548.
6. Klaman LD, Boss O, Peroni OD, Kim JK, Martino JL, Zabolotny JM, Moghal N, Lubkin M, Kim YB, Sharpe AH, Stricker-Krongrad A, Shulman GI, Neel BG, Kahn BB. Increased energy expenditure, decreased adiposity, and tissue-specific insulin sensitivity in proteintyrosine phosphatase 1B-deficient mice. Mol Cell Biol 2000; 20: 5479-5489.
7. Zhang S, Zhang Z-Y. PTP1B as a drug target: recent developments in PTP1B inhibitor discovery. Drug Discov Today 2007; 12: 373-381.
8. Xie L, Lee S-Y, Anderson JN, Waters S, Shen K, Guo XL, Moller NPH, Olefsky JM, Lawrence DS, Zhang Z-Y. Cellular effects of small molecule PTP1B inhibitors on insulin signaling. Biochemistry 2003; 42: 12792-12804.
9. Zabolotny JM, Bence-Hanulec KK, Stricker-Krongrad A, Haj F, Wang Y, Minokoshi Y, Kim YB, Elmquist JK, Tartaglia LA, Kahn BB, Neel BG. PTP1B regulates leptin signal transduction in vivo. Dev Cell 2002; 2: 489-495.
10. Kaszubska W, Falls HD, Schaefer VG, Haasch D, Frost L, Hessler P, Kroeger P E, White DW, Jirousek MR, Trevillyan JM. Protein tyrosine phosphatase 1B negatively regulates leptin signaling in a hypothalamic cell line. Mol Cell Endocrinol 2002; 195: 109-118.
11. Myers MG Jr. Leptin receptor signaling and the regulation of mammalian physiology. Recent Prog Horm Res 2004; 59: 287-304.
12. Morrison CD, White CL, Wang Z, Lee SY, Lawrence DS, Cefalu WT, Zhang ZY, Gettys TW. Increased hypothalamic protein tyrosine phosphatase 1B contributes to leptin resistance with age. Endocrinology 2007; 148: 433-440.
13. Johnson TO., Ermolieff J, Jirousek MR. Protein tyrosine phosphatase 1B inhibitors for diabetes. Nat Rev Drug Discov 2002; 1: 696-709.
14. Lee S, Wang Q. Recent development of small molecular specific inhibitor of protein tyrosine phosphatase 1B. Med Res Rev 2007; 27: 553-573.
15. Huneck S. The significance of lichens and their metabolites. Naturwissenschaften 1999; 86: 559-570.
16. Ingólfsdóttir K. Usnic acid. Phytochemistry 2002; 61: 729-736.
17. Lohezic-Le Devehat F, Tomasi S, Elix JA, Bernard A, Rouaud I, Uriac P, Boustie J. Stictic acid derivatives from the lichen Usnea articulata and their antioxidant activities. J Nat Prod 2007; 70: 1218-1220.
18. Kumar KCS., M̈ller K. Lichen metabolites. 1. Inhibitory action against leukotriene B4 biosynthesis by a non-redox mechanism. J Nat Prod 1999; 62: 817-820.
19. Ernst-Russell MA, Chai CLL, Wardlaw JH, Elix JA. Euplectin and coneuplectin, new naphthopyrones from the lichen Flavoparmelia euplecta. J Nat Prod 2000; 63: 129-131.
20. Seo C, Choi YH, Sohn JH, Ahn JS., Yim JH, Lee HK, Oh H. Ohioensins F and G: protein tyrosine phosphatase 1B inhibitory benzonaphthoxanthenones from the Antarctic moss Polytrichastrum alpinum. Bioorg Med Chem Lett 2008; 18: 772-775.
21. Seo C., Yim JH, Lee HK, Park SM, Sohn JH, Oh H. Stereocalpin A, a bioactive cyclic depsipeptide from the Antarctic lichen Stereocaulon alpinum. Tetrahedron Lett 2008; 49: 29-31. (Pubitemid 350191888)
22. Seo C., Sohn JH., Park SM, Yim JH, Lee HK, Oh H. Usimines A-C, bioactive usnic acid derivatives from the Antarctic lichen Stereocaulon alpinum. J Nat Prod 2008; 71: 710-712.
23. Narui T, Sawada K, Takatsuki S, Okuyama T, Culberson CF, Culberson WL, Shibata S. NMR assignments of depsides and tridepsides of the lichen family Umbilicariaceae. Phytochemistry 1998; 48: 815-822.
24. Na M, Tang S, He L, Oh H, Kim BS, Oh WK, Kim BY, Ahn JS. Inhibition of protein tyrosine phosphatase 1B by ursane-type triterpenes isolated from Symplocos paniculata. Planta Med 2006; 72: 261-263.
25. Zhang W, Hong D, Zhou Y, Zhang Y, Shen Q, Li J, Hu L, Li J. Ursolic acid and its derivative inhibit protein tyrosine phosphatase 1B, enhancing insulin receptor phosphorylation and stimulating glucose uptake. Biocheim Biophy Acta 2006; 1760: 1505-1512.
26. Wiesmann C, Barr KJ, Kung J, Zhu J, Erlanson DA, Shen W, Fahr BJ, Zhong M, Taylor L, Randal M, McDowell RS, Hansen SK. Allosteric inhibition of protein tyrosine phosphatase 1B. Nat Struct Mol Biol 2004; 11: 730-737.
27. Ögmundsdóttir HM, Zoega GM, Gissurarson SR, Ingólfsdóttir K. Antiproliferative effects of lichen-derived inhibitors of 5-lipoxygenase on malignant cell-lines and mitogen-stimulated lymphocytes. J Pharm Pharmacol 1998; 50: 107-115.
28. Kumar KC S, M̈ller K. Lichen metabolites. 2. Antiproliferative and cytotoxic activity of gyrophoric, usnic, and diffractaic acid on human keratinocyte growth. J Nat Prod 1999; 62: 821-823.