PTP1B inhibitory and anti-inflammatory effects of secondary metabolites isolated from the marine-derived fungus Penicillium sp. JF-55

Marine Drugs

Volumn 11, Issue 4, 2013, Pages 1409-1426

  Lee, Dong Sung ^a   Jang, Jae Hyuk ^b   Ko, Wonmin ^a   Kim, Kyoung Su ^a   Sohn, Jae Hak ^c   Kang, Myeong Suk ^c   Ahn, Jong Seog ^b   Kim, Youn Chul ^a   Oh, Hyuncheol ^a,b  

^a Wonkwang University   (South Korea)

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

^c Silla University   (South Korea)

Author keywords

Anti inflammatory effect; Heme oxygenase 1; Marine derived fungi; Penicillium sp.; PTP1B inhibitors

Indexed keywords

2 BUTANONE; ANHYDROFULVIC ACID; ANTIINFLAMMATORY AGENT; CITROMYCETIN; CYCLOOXYGENASE 2; FUNGAL EXTRACT; HEME OXYGENASE 1; I KAPPA B ALPHA; IMMUNOGLOBULIN ENHANCER BINDING PROTEIN; INDUCIBLE NITRIC OXIDE SYNTHASE; INTERLEUKIN 1BETA; NITRIC OXIDE; PENSTYRYLPYRONE; PROSTAGLANDIN E2; PROTEIN TYROSINE PHOSPHATASE 1B; PROTOPORPHYRIN TIN; TUMOR NECROSIS FACTOR ALPHA; UNCLASSIFIED DRUG; URSOLIC ACID;

ANIMAL CELL; ANTIINFLAMMATORY ACTIVITY; ARTICLE; COMPETITIVE INHIBITION; CONCENTRATION RESPONSE; CONTROLLED STUDY; CYTOKINE PRODUCTION; DNA BINDING; DRUG ISOLATION; DRUG STRUCTURE; ENZYME INHIBITION; NONHUMAN; NUCLEOTIDE SEQUENCE; PENICILLIUM; PERITONEUM MACROPHAGE; PROTEIN DEGRADATION; PROTEIN PHOSPHORYLATION;

FUNGI; PENICILLIUM SP.;

EID: 84876967503     PISSN: None     EISSN: 16603397     Source Type: Journal    
DOI: 10.3390/md11041409     Document Type: Article

References (46)

1. Olano, C.; Méndez, C.; Salas, J.A. Antitumor compounds from marine actinomycetes. Mar. Drugs 2009, 7, 210-248.
2. Rateb, M.E.; Ebel, R. Secondary metabolites of fungi from marine habitats. Nat. Prod. Rep. 2011, 28, 290-344.
3. Debbab, A.; Aly, A.H.; Lin, W.H.; Proksch, P. Bioactive compounds from marine bacteria and fungi. Microb. Biotechnol. 2010, 3, 544-563.
4. Greve, H.; Mohamed, I.E.; Pontius, A.; Kehraus, S.; Gross, H.; König, G.M. Fungal metabolites: Structural diversity as incentive for anticancer drug development. Phytochem. Rev. 2010, 9, 537-545.
5. Liu, D.; Li, X.M.; Meng, L.; Li, C.S.; Gao, S.S.; Shang, Z.; Proksch, P.; Huang, C.G.; Wang, B.G. Nigerapyrones A-H, α-pyrone derivatives from the marine mangrove-derived endophytic fungus Aspergillus niger MA-132. J. Nat. Prod. 2011, 74, 1787-1791.
6. Yan, H.J.; Li, X.M.; Li, C.S.; Wang, B.G. Alkaloid and anthraquinone derivatives produced by the marine-derived endophytic fungus Eurotium rubrum. Helv. Chim. Acta 2012, 95, 163-168.
7. Seo, C.; Sohn, J.H.; Oh, H.; Kim, B.Y.; Ahn, J.S. Isolation of the protein tyrosine ohosphatase 1B inhibitory metabolite from the marine-derived fungus Cosmospora sp. SF-5060. Bioorg. Med. Chem. Lett. 2009, 19, 6095-6097.
8. Lee, D.S.; Jeong, G.S.; Li, B.; Lee, S.U.; Oh, H.; Kim, Y.C. Asperlin from the marine-derived fungus Aspergillus sp. SF-5044 exerts anti-inflammatory effects through heme oxygenase-1 expression in murine macrophages. J. Pharmacol. Sci. 2011, 116, 283-295.
9. Fisher, E.H.; Charbonneau, H.; Tonks, N.K. Protein tyrosine phosphatases: A diverse family of intracellular and transmembrane enzymes. Science 1991, 253, 401-406.
10. Hunter, T. Protein kinases and phosphatases: The yin and yang of protein phosphorylation and signaling. Cell 1995, 80, 225-236.
11. Saltiel, A.R.; Kahn, C.R. Insulin signalling and the regulation of glucose and lipid metabolism. Nature 2001, 414, 799-806.
12. Elchebly, M.; Payette, P.; Michaliszyn, E.; Cromlish, W.; Collins, S.; Loy, A.L.; Normandin, D.; Cheng, A.; Himms-Hagen, J.; Chan, C.C.; et al. Increased insulin sensitivity and obesity resistance in mice lacking the protein tyrosine phosphatase-1B gene. Science 1999, 283, 1544-1548.
13. Klaman, L.D.; Boss, O.; Peroni, O.D.; Kim, J.K.; Martino, J.L.; Zabolotny, J.M.; Moghal, N.; Lubkin, M.; Kim, Y.B.; Sharpe, A.H.; et al. Increased energy expenditure, decreased adiposity, and tissue-specific insulin sensitivity in protein-tyrosine phosphatase 1B-deficient mice. Mol. Cell. Biol. 2000, 20, 5479-5489.
14. Koren, S.; Fantus, I.G. Inhibition of the protein tyrosine phosphatase PTP1B: Potential therapy for obesity, insulin resistance and type-2 diabetes mellitus. Best Pract. Res. Clin. Endocrinol. Metab. 2007, 21, 621-640.
15. Dadke, S.; Chernoff, J. Protein-tyrosine phosphatase 1B as a potential drug target for obesity. Curr. Drug Targets Immune Endocr. Metabol. Disord. 2003, 3, 299-304.
16. Paine, A.; Eiz-Vesper, B.; Blasczyk, R.; Immenschuh, S. Signaling to heme oxygenase-1 and its anti-inflammatory therapeutic potential. Biochem. Pharmacol. 2010, 80, 1895-1903.
17. Ryter, S.W.; Alam, J.; Choi, A.M. Heme oxygenase-1/carbon monoxide: From basic science to therapeutic applications. Physiol. Rev. 2006, 86, 583-650.
18. Otterbein, L.E.; Bach, F.H.; Alam, J.; Soares, M.; Lu, H.T.; Wysk, M.; Davis, R.J.; Flavell, R.A.; Choi, A.M. Carbon monoxide has anti-inflammatory effects involving the mitogen-activated protein kinase pathway. Nat. Med. 2000, 6, 422-428.
19. Wiesel, P.; Foster, L.C.; Pellacani, A.; Layne, M.D.; Hsieh, C.M.; Huggins, G.S.; Strauss, P.; Yet, S.F.; Perrella, M.A. Thioredoxin facilitates the induction of heme oxygenase-1 in response to inflammatory mediators. J. Biol. Chem. 2000, 275, 24840-24846.
20. Suh, G.Y.; Jin, Y.; Yi, A.K.; Wang, X.M.; Choi, A.M. CCAAT/enhancer- binding protein mediates carbon monoxide-induced suppression of cyclooxygenase-2. Am. J. Respir. Cell Mol. Biol. 2006, 35, 220-226.
21. Oh, G.S.; Pae, H.O.; Lee, B.S.; Kim, B.N.; Kim, J.M.; Kim, H.R.; Jeon, S.B.; Jeon, W.K.; Chae, H.J.; Chung, H.T. Hydrogen sulfide inhibits nitric oxide production and nuclear factor-kappaB via heme oxygenase-1 expression in RAW264.7 macrophages stimulated with lipopolysaccharide. Free Radic. Biol. Med. 2006, 41, 106-119.
22. Itoh, K.; Chiba, T.; Takahashi, S.; Ishii, T.; Igarashi, K.; Katoh, Y.; Oyake, T.; Hayashi, N.; Satoh, K.; Hatayama, I.; et al. An Nrf2/small Maf heterodimer mediates the induction of phase II detoxifying enzyme genes through antioxidant response elements. Biochem. Biophys. Res. Commun. 1997, 236, 313-322.
23. Kobayashi, M.; Yamamoto, M. Molecular mechanisms activating the Nrf2-Keap1 pathway of antioxidant gene regulation. Antioxid. Redox Signal. 2005, 7, 385-394.
24. Schmidt, L.E.; Gloer, J.B.; Wicklow, D.T. Solanapyrone analogues from a Hawaiian fungicolous fungus. J. Nat. Prod. 2007, 70, 1317-1320.
25. Kemami, H.V.K.; Hertweck, C. Squarrosidine and pinillidine: 3,3′-fused bis (styrylpyrones) from Pholiota squarrosa and Phellinus pini . Eur. J. Org. Chem. 2007, 20, 3292-3295.
26. Mo, S.Y.; Yang, Y.C.; He, W.Y.; Shi, J.G. Two pyrone derivatives from fungus Phellinus igniarius . Chin. Chem. Lett. 2003, 14, 704-706.
27. Ali, N.A.A.; Jansen, R.; Pilgrim, H.; Liberra, K.; Lindequist, U. Hispolon, a yellow pigment from Inonotus hispidus . Phytochemistry 1996, 41, 927-929.
28. Fujita, K.I.; Nagamine, Y.; Ping, X.; Taniguchi, M. Mode of action of anhydrofulvic acid against Candida utilis ATCC 42402 under acidic condition. J. Antibiot. 1999, 52, 628-634.
29. Capon, R.J.; Stewart, M.; Ratnayake, R.; Lacey, E.; Gill, J.H. Citromycetins and bilains A-C: New aromatic polyketides and diketopiperazines from Australian marine-derived and terrestrial Penicillium spp. J. Nat. Prod. 2007, 70, 1746-1752.
30. Na, M.; Tang, S.; He, L.; Oh, H.; Kim, B.S.; Oh, W.K.; Kim, B.Y.; Ahn, J.S. Inhibition of protein tyrosine phosphatase 1B by ursane-type triterpenes isolated from Symplocos paniculata. Planta Med. 2006, 72, 261-263.
31. 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. Biochem. Biophy. Acta 2006, 1760, 1505-1512.
32. Surh, Y.J.; Chun, K.S.; Cha, H.H.; Han, S.S.; Keum, Y.S.; Park, K.K.; Lee, S.S. Molecular mechanisms underlying chemopreventive activities of anti-inflammatory phytochemicals: Down-regulation of COX-2 and iNOS through suppression of NF-kappaB activation. Mutat. Res. 2001, 480-481, 243-268.
33. Verma, I.M.; Stevenson, J.K.; Schwarz, E.M.; van Antwerp, D.; Miyamoto, S. Rel/NF-kappaB/IkappaB family: Intimate tales of association and dissociation. Genes Dev. 1995, 9, 2723-2735.
34. Sato, K.; Balla, J.; Otterbein, L.; Smith, R.N.; Brouard, S.; Lin, Y.; Csizmadia, E.; Sevigny, J.; Robson, S.C.; Vercellotti, G.; et al. Carbon monoxide generated by heme oxygenase-1 suppresses the rejection of mouse-to-rat cardiac transplants. J. Immunol. 2001, 166, 4185-4194.
35. Hamaguchi, T.; Sudo, T.; Osada, H. RK-682, a potent inhibitor of tyrosine phosphatase, arrested the mammalian cell cycle progression at G1phase. FEBS Lett. 1995, 372, 54-58.
36. Oh, H.; Kim, B.S.; Bae, E.Y.; Kim, M.S.; Kim, B.Y.; Lee, H.B.; Kim, C.J.; Ahn, J.S. Inhibition of PTP1B by metabolites from Micromucor ramannianus var. angulisporus CRM000232. J. Antibiot . 2004, 57, 528-531.
37. Narumi, S.; Finke, J.H.; Hamilton, T.A. Interferon gamma and interleukin 2 synergize to induce selective monokine expression in murine peritoneal macrophages. J. Biol. Chem. 1990, 265, 7036-7041.
38. Berridge, M.V.; Tan, A.S. Characterization of the cellular reduction of 3-(4,5-dimethylthiazol-2-yl)-2,5-diphenyltetrazolium bromide (MTT): Subcellular localization, substrate dependence, and involvement of mitochondrial electron transport in MTT reduction. Arch. Biochem. Biophys. 1993, 303, 474-482.
39. Titheradge, M.A. The enzymatic measurement of nitrate and nitrite. Meth. Mol. Biol. 1998, 303, 474-482.
40. Sawle, P.; Foresti, R.; Mann, B.E.; Johnson, T.R.; Green, C.J.; Motterlini, R. Carbon monoxide-releasing molecules (CO-RMs) attenuate the inflammatory response elicited by lipopolysaccharide in RAW264.7 murine macrophages. Br. J. Pharmacol. 2005, 145, 800-810.
41. Liljebris, C.; Martinsson, J.; Tedenborg, L.; Williams, M.; Barker, E.; Duffy, J.E.S.; Nygren, A.; James, S. Pigments of fungi (macromycetes). Nat. Prod. Rep. 2010, 27, 1531-1570.
42. Lee, I.K.; Yun, B.S. Styrylpyrone-class compounds from medicinal fungi Phellinus and Inonotus spp., and their medicinal importance. J. Antiobiot. 2011, 64, 349-359.
43. Wrigley, S.K.; Latif, M.A.; Gibson, T.M.; Chicarelli-Robinson, M.I.; Williams, D.H. Structure elucidation of xanthone derivatives with CD4-binding activity from Penicillium glabrum (Wehmer) Westling. Pure Appl. Chem. 1994, 66, 2383-2386.
44. Zabolotny, J.M.; Kim, Y.B.; Welsh, L.A.; Kershaw, E.E.; Neel, B.G.; Kahn, B.B. Proteintyrosine phosphatase 1B expression is induced by inflammation in vivo. J. Biol. Chem. 2008, 283, 14230-14241.
45. González-Rodríguez, A.; Más-Gutierrez, J.A.; Mirasierra, M.; Fernandez-Pérez, A.; Lee, Y.J.; Ko, H.J.; Kim, J.K.; Romanos, E.; Carrascosa, J.M.; Ros, M.; et al. Essential role of protein tyrosine phosphatase 1B in obesity-induced inflammation and peripheral insulin resistance during aging. Aging Cell 2012, 11, 284-296.
46. García-San Frutos, M.; Fernández-Agulló, T.; Carrascosa, J.M.; Horrillo, D.; Barrús, M.T.; Oliveros, E.; Sierra, J.; Ros, M. Involvement of protein tyrosine phosphatases and inflammation in hypothalamic insulin resistance associated with ageing: Effect of caloric restriction. Mech. Aging Dev. 2012, 133, 489-497.