Pinosylvin and Monomethylpinosylvin, Constituents of an Extract from the Knot of Pinus sylvestris, Reduce Inflammatory Gene Expression and Inflammatory Responses in Vivo

Journal of Agricultural and Food Chemistry

Volumn 63, Issue 13, 2015, Pages 3445-3453

  Laavola, Mirka ^a   Nieminen, Riina ^a   Leppänen, Tiina ^a   Eckerman, Christer ^b   Holmbom, Bjarne ^b   Moilanen, Eeva ^a  

^a TAMPERE UNIVERSITY OF TECHNOLOGY   (Finland)

^b ÅBO AKADEMI UNIVERSITY   (Finland)

Author keywords

anti inflammatory; HO 1; iNOS; Pinus sylvestris; stilbene

Indexed keywords

GENE EXPRESSION; IMMUNOLOGY; NITRIC OXIDE; PATHOLOGY;

ANTI-INFLAMMATORIES; ANTI-INFLAMMATORY EFFECTS; INDUCIBLE NITRIC OXIDE SYNTHASE (INOS); INFLAMMATORY CYTOKINES; INFLAMMATORY GENE EXPRESSIONS; INOS; PINUS SYLVESTRIS; STILBENE;

FORESTRY;

PINUS SYLVESTRIS;

ANTIINFLAMMATORY AGENT; CARRAGEENAN; IMMUNOGLOBULIN ENHANCER BINDING PROTEIN; INDUCIBLE NITRIC OXIDE SYNTHASE; INTERLEUKIN 6; MONOCYTE CHEMOTACTIC PROTEIN 1; MONOMETHYLPINOSYLVIN; NITRIC OXIDE; PINOSYLVIN; PLANT EXTRACT; STILBENE DERIVATIVE;

ANIMAL; ANTAGONISTS AND INHIBITORS; BIOSYNTHESIS; CELL LINE; CHEMICALLY INDUCED; CHEMISTRY; DRUG EFFECTS; ENZYMOLOGY; GENE EXPRESSION; GENETICS; HEK293 CELL LINE; HUMAN; INFLAMMATION; ISOLATION AND PURIFICATION; MACROPHAGE; METABOLISM; MOUSE; SCOTS PINE; WOOD;

ANIMALS; ANTI-INFLAMMATORY AGENTS; CARRAGEENAN; CELL LINE; CHEMOKINE CCL2; GENE EXPRESSION; HEK293 CELLS; HUMANS; INFLAMMATION; INTERLEUKIN-6; MACROPHAGES; MICE; NF-KAPPA B; NITRIC OXIDE; NITRIC OXIDE SYNTHASE TYPE II; PINUS SYLVESTRIS; PLANT EXTRACTS; STILBENES; WOOD;

EID: 84926648088     PISSN: 00218561     EISSN: 15205118     Source Type: Journal    
DOI: 10.1021/jf504606m     Document Type: Article

References (38)

1. Holmbom, B.; Willför, S.; Hemming, J.; Pietarinen, S.; Nisula, S.; Eklund, P.; Sjöholm, R. Knots in trees-a rich source of bioactive polyphenols In ACS Symposium Series 954; Argyropoulos, D., Ed.; American Chemical Society: Washington, DC, USA, 2007; pp 350 - 362.
2. Willför, S.; Hemming, J. E.; Reunanen, M. H.; Holmbom, B. Phenolic and lipophilic extractives in scots pine knots and stemwood Holzforschung 2003, 57, 359 - 372
3. Välimaa, A. L.; Honkalampi-Hämäläinen, U.; Pietarinen, S.; Willfor, S.; Holmbom, B.; von Wright, A. Antimicrobial and cytotoxic knotwood extracts and related pure compounds and their effects on food-associated microorganisms Int. J. Food Microbiol. 2007, 115, 235 - 243
4. Kulkarni, S. S.; Canto, C. The molecular targets of resveratrol Biochim. Biophys. Acta 2014, 10.1016/j.bbadis.2014.10.005
5. Djoko, B.; Chiou, R. Y.; Shee, J. J.; Liu, Y. W. Characterization of immunological activities of peanut stilbenoids, arachidin-1, piceatannol, and resveratrol on lipopolysaccharide-induced inflammation of RAW 264.7 macrophages J. Agric. Food Chem. 2007, 55, 2376 - 2383
6. Wang, K. T.; Chen, L. G.; Tseng, S. H.; Huang, J. S.; Hsieh, M. S.; Wang, C. C. Anti-inflammatory effects of resveratrol and oligostilbenes from Vitis thunbergii var. taiwaniana against lipopolysaccharide-induced arthritis J. Agric. Food Chem. 2011, 59, 3649 - 3656
7. de la Lastra, C. A.; Villegas, I. Resveratrol as an anti-inflammatory and anti-aging agent: mechanisms and clinical implications Mol. Nutr. Food Res. 2005, 49, 405 - 430
8. Scatena, R.; Bottoni, P.; Pontoglio, A.; Giardina, B. Pharmacological modulation of nitric oxide release: new pharmacological perspectives, potential benefits and risks Curr. Med. Chem. 2010, 17, 61 - 73
9. Kanwar, J. R.; Kanwar, R. K.; Burrow, H.; Baratchi, S. Recent advances on the roles of NO in cancer and chronic inflammatory disorders Curr. Med. Chem. 2009, 16, 2373 - 2394
10. Lyons, C. R.; Orloff, G. J.; Cunningham, J. M. Molecular cloning and functional expression of an inducible nitric oxide synthase from a murine macrophage cell line J. Biol. Chem. 1992, 267, 6370 - 6374
11. Korhonen, R.; Lahti, A.; Kankaanranta, H.; Moilanen, E. Nitric oxide production and signaling in inflammation Curr. Drug Targets Inflamm. Allergy 2005, 4, 471 - 479
12. Pautz, A.; Art, J.; Hahn, S.; Nowag, S.; Voss, C.; Kleinert, H. Regulation of the expression of inducible nitric oxide synthase Nitric Oxide 2010, 23, 75 - 93
13. 15N]nitrate in biological fluids Anal. Biochem. 1982, 126, 131 - 138
14. Bradford, M. M. A rapid and sensitive method for the quantitation of microgram quantities of protein utilizing the principle of protein-dye binding Anal. Biochem. 1976, 72, 248 - 254
15. Leppänen, T.; Jalonen, U.; Korhonen, R.; Tuominen, R. K.; Moilanen, E. Inhibition of protein kinase Cdelta reduces tristetraprolin expression by destabilizing its mRNA in activated macrophages Eur. J. Pharmacol. 2010, 628, 220 - 225
16. 2-terminal kinase inhibitor anthra(1,9- cd)pyrazol-6(2 H)-one reduces inducible nitric-oxide synthase expression by destabilizing mRNA in activated macrophages Mol. Pharmacol. 2003, 64, 308 - 315
17. Yatkin, E.; Polari, L.; Laajala, T. D.; Smeds, A.; Eckerman, C.; Holmbom, B.; Saarinen, N. M.; Aittokallio, T.; Mäkelä, S. I. Novel lignan and stilbenoid mixture shows anticarcinogenic efficacy in preclinical PC-3M-luc2 prostate cancer model PLoS One 2014, 9 e93764
18. Macickova, T.; Drabikova, K.; Nosal, R.; Bauerova, K.; Mihalova, D.; Harmatha, J.; Pecivova, J. In vivo effect of pinosylvin and pterostilbene in the animal model of adjuvant arthritis Neuro Endocrinol. Lett. 2010, 31 (Suppl. 2) 91 - 95
19. Pietarinen, S.; Willför, S.; Hemming, J.; Holmbom, B. Knotwood and bark extracts: strong antioxidants from waste materials J. Wood Sci. 2006, 52, 436 - 444
20. 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
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 Radical Biol. Med. 2006, 41, 106 - 119
22. Vigo, E.; Cepeda, A.; Gualillo, O.; Perez-Fernandez, R. In-vitro anti-inflammatory activity of Pinus sylvestris and Plantago lanceolata extracts: effect on inducible NOS, COX-1, COX-2 and their products in J774A.1 murine macrophages J. Pharm. Pharmacol. 2005, 57, 383 - 391
23. Karonen, M.; Hämäläinen, M.; Nieminen, R.; Klika, K. D.; Loponen, J.; Ovcharenko, V. V.; Moilanen, E.; Pihlaja, K. Phenolic extractives from the bark of Pinus sylvestris L. and their effects on inflammatory mediators nitric oxide and prostaglandin E2 J. Agric. Food Chem. 2004, 52, 7532 - 7540
24. Cho, D. I.; Koo, N. Y.; Chung, W. J.; Kim, T. S.; Ryu, S. Y.; Im, S. Y.; Kim, K. M. Effects of resveratrol-related hydroxystilbenes on the nitric oxide production in macrophage cells: structural requirements and mechanism of action Life Sci. 2002, 71, 2071 - 2082
25. Matsuda, H.; Kageura, T.; Morikawa, T.; Toguchida, I.; Harima, S.; Yoshikawa, M. Effects of stilbene constituents from rhubarb on nitric oxide production in lipopolysaccharide-activated macrophages Bioorg. Med. Chem. Lett. 2000, 10, 323 - 327
26. Tsai, S. H.; Lin-Shiau, S. Y.; Lin, J. K. Suppression of nitric oxide synthase and the down-regulation of the activation of NFkappaB in macrophages by resveratrol Br. J. Pharmacol. 1999, 126, 673 - 680
27. Liu, F. C.; Hung, L. F.; Wu, W. L.; Chang, D. M.; Huang, C. Y.; Lai, J. H.; Ho, L. J. Chondroprotective effects and mechanisms of resveratrol in advanced glycation end products-stimulated chondrocytes Arthritis Res. Ther. 2010, 12, R167
28. Shakibaei, M.; Csaki, C.; Nebrich, S.; Mobasheri, A. Resveratrol suppresses interleukin-1beta-induced inflammatory signaling and apoptosis in human articular chondrocytes: potential for use as a novel nutraceutical for the treatment of osteoarthritis Biochem. Pharmacol. 2008, 76, 1426 - 1439
29. Park, E. J.; Min, H. Y.; Chung, H. J.; Ahn, Y. H.; Pyee, J. H.; Lee, S. K. Pinosylvin suppresses LPS-stimulated inducible nitric oxide synthase expression via the MyD88-independent, but TRIF-dependent downregulation of IRF-3 signaling pathway in mouse macrophage cells Cell. Physiol. Biochem. 2011, 27, 353 - 362
30. Zhang, Z.; Shi, L. Anti-inflammatory and analgesic properties of cis -mulberroside A from Ramulus mori Fitoterapia 2010, 81, 214 - 218
31. Lee, J.; Jung, E.; Lim, J.; Lee, J.; Hur, S.; Kim, S. S.; Lim, S.; Hyun, C. G.; Kim, Y. S.; Park, D. Involvement of nuclear factor-kappaB in the inhibition of pro-inflammatory mediators by pinosylvin Planta Med. 2006, 72, 801 - 806
32. Park, E. J.; Min, H. Y.; Ahn, Y. H.; Bae, C. M.; Pyee, J. H.; Lee, S. K. Synthesis and inhibitory effects of pinosylvin derivatives on prostaglandin E2 production in lipopolysaccharide-induced mouse macrophage cells Bioorg. Med. Chem. Lett. 2004, 14, 5895 - 5898
33. Motterlini, R.; Foresti, R. Heme oxygenase-1 as a target for drug discovery Antioxid. Redox Signal. 2013, 20, 1810 - 1826
34. Juan, S. H.; Cheng, T. H.; Lin, H. C.; Chu, Y. L.; Lee, W. S. Mechanism of concentration-dependent induction of heme oxygenase-1 by resveratrol in human aortic smooth muscle cells Biochem. Pharmacol. 2005, 69, 41 - 48
35. Handy, R. L.; Moore, P. K. A comparison of the effects of L-NAME, 7-NI and L-NIL on carrageenan-induced hindpaw oedema and NOS activity Br. J. Pharmacol. 1998, 123, 1119 - 1126
36. Salvemini, D.; Wang, Z. Q.; Wyatt, P. S.; Bourdon, D. M.; Marino, M. H.; Manning, P. T.; Currie, M. G. Nitric oxide: a key mediator in the early and late phase of carrageenan-induced rat paw inflammation Br. J. Pharmacol. 1996, 118, 829 - 838
37. Hämäläinen, M.; Lilja, R.; Kankaanranta, H.; Moilanen, E. Inhibition of iNOS expression and NO production by anti-inflammatory steroids. Reversal by histone deacetylase inhibitors Pulm. Pharmacol. Ther. 2008, 21, 331 - 339
38. Gentilli, M.; Mazoit, J. X.; Bouaziz, H.; Fletcher, D.; Casper, R. F.; Benhamou, D.; Savouret, J. F. Resveratrol decreases hyperalgesia induced by carrageenan in the rat hind paw Life Sci. 2001, 68, 1317 - 1321