Carnosol and related substances modulate chemokine and cytokine production in macrophages and chondrocytes

Molecules

Volumn 21, Issue 4, 2016, Pages

  Schwager, Joseph ^a   Richard, Nathalie ^a   Fowler, Ann ^a   Seifert, Nicole ^a   Raederstorff, Daniel ^a  

^a DSM NUTRITIONAL PRODUCTS LTD   (Switzerland)

Author keywords

Abietanes; Acute inflammation; Carnosol; Chondrocyte; Chronic inflammation; Innate immune response; Murine macrophages; NF e B signaling pathway and nuclear translocation; Osteoarthritis

Indexed keywords

20-DEOXOCARNOSOL; ABIETANE DERIVATIVE; CARNOSOL; CCL5 PROTEIN, HUMAN; CHEMOKINE; COL2A1 PROTEIN, HUMAN; COLLAGEN TYPE 2; CYTOKINE; IMMUNOGLOBULIN ENHANCER BINDING PROTEIN; INTERLEUKIN 1BETA; NITRIC OXIDE; PHENANTHRENE DERIVATIVE; RANTES;

ANIMAL; BIOSYNTHESIS; CHONDROCYTE; DRUG EFFECTS; GENE EXPRESSION REGULATION; HUMAN; MACROPHAGE; METABOLISM; MOUSE; OSTEOARTHRITIS; PATHOLOGY; RAW 264.7 CELL LINE;

ANIMALS; CHEMOKINE CCL5; CHEMOKINES; CHONDROCYTES; COLLAGEN TYPE II; CYTOKINES; DITERPENES, ABIETANE; GENE EXPRESSION REGULATION; HUMANS; INTERLEUKIN-1BETA; MACROPHAGES; MICE; NF-KAPPA B; NITRIC OXIDE; OSTEOARTHRITIS; PHENANTHRENES; RAW 264.7 CELLS;

EID: 84968884352     PISSN: None     EISSN: 14203049     Source Type: Journal    
DOI: 10.3390/molecules21040465     Document Type: Article

References (43)

1. Aruoma, O.I.; Halliwell, B.; Aeschbach, R.; Loligers, J. Antioxidant and pro-oxidant properties of active rosemary constituents: Carnosol and carnosic acid. Xenobiotica 1992, 22, 257-268.
2. Aruoma, O.I.; Spencer, J.P.; Rossi, R.; Aeschbach, R.; Khan, A.; Mahmood, N.; Munoz, A.; Murcia, A.; Butler, J.; Halliwell, B. An evaluation of the antioxidant and antiviral action of extracts of rosemary and provencal herbs. Food Chem. Toxicol. 1996, 34, 449-456.
3. Chan, M.M.; Ho, C.T.; Huang, H.I. Effects of three dietary phytochemicals from tea, rosemary and turmeric on inflammation-induced nitrite production. Cancer Lett. 1995, 96, 23-29.
4. Lo, A.H.; Liang, Y.C.; Lin-Shiau, S.Y.; Ho, C.T.; Lin, J.K. Carnosol, an antioxidant in rosemary, suppresses inducible nitric oxide synthase through down-regulating nuclear factor-kappab in mouse macrophages. Carcinogenesis 2002, 23, 983-991.
5. Miura, K.; Kikuzaki, H.; Nakatani, N. Antioxidant activity of chemical components from sage (Salvia officinalis L.) and thyme (Thymus vulgaris L.) measured by the oil stability index method. J. Agric. Food Chem. 2002, 50, 1845-1851.
6. Zeng, H.H.; Tu, P.F.; Zhou, K.; Wang, H.; Wang, B.H.; Lu, J.F. Antioxidant properties of phenolic diterpenes from rosmarinus officinalis. Acta Pharmacol. Sin. 2001, 22, 1094-1098.
7. Dorrie, J.; Sapala, K.; Zunino, S.J. Carnosol-induced apoptosis and downregulation of BcL-2 in B-lineage leukemia cells. Cancer Lett. 2001, 170, 33-39.
8. Huang, M.T.; Ho, C.T.; Wang, Z.Y.; Ferraro, T.; Lou, Y.R.; Stauber, K.; Ma, W.; Georgiadis, C.; Laskin, J.D.; Conney, A.H. Inhibition of skin tumorigenesis by rosemary and its constituents carnosol and ursolic acid. Cancer Res. 1994, 54, 701-708.
9. Johnson, J.J.; Syed, D.N.; Heren, C.R.; Suh, Y.; Adhami, V.M.; Mukhtar, H. Carnosol, a dietary diterpene, displays growth inhibitory effects in human prostate cancer PC3 cells leading to G2-phase cell cycle arrest and targets the 51 -AMP-activated protein kinase (AMPK) pathway. Pharm. Res. 2008, 25, 2125-2134.
10. Mace, K.; Offord, E.A.; Harris, C.C.; Pfeifer, A.M. Development of in vitro models for cellular and molecular studies in toxicology and chemoprevention. Arch. Toxicol. Suppl. 1998, 20, 227-236.
11. Moran, A.E.; Carothers, A.M.; Weyant, M.J.; Redston, M.; Bertagnolli, M.M. Carnosol inhibits beta-catenin tyrosine phosphorylation and prevents adenoma formation in the C57bl/6j/min/+ (min/+) mouse. Cancer Res. 2005, 65, 1097-1104.
12. Visanji, J.M.; Thompson, D.G.; Padfield, P.J. Induction of G2/M phase cell cycle arrest by carnosol and carnosic acid is associated with alteration of cyclin a and cyclin b1 levels. Cancer Lett. 2006, 237, 130-136.
13. Johnson, J.J. Carnosol: A promising anti-cancer and anti-inflammatory agent. Cancer Lett. 2011, 305, 1-7.
14. Kim, S.J.; Kim, J.S.; Cho, H.S.; Lee, H.J.; Kim, S.Y.; Kim, S.; Lee, S.Y.; Chun, H.S. Carnosol, a component of rosemary (Rosmarinus officinalis L.) protects nigral dopaminergic neuronal cells. Neuroreport 2006, 17, 1729-1733.
15. Park, K.W.; Kundu, J.; Chae, I.G.; Kim, D.H.; Yu, M.H.; Kundu, J.K.; Chun, K.S. Carnosol induces apoptosis through generation of ROS and inactivation of STAT3 signaling in human colon cancer HCT116 cells. Int. J. Oncol. 2014, 44, 1309-1315.
16. Peng, C.H.; Su, J.D.; Chyau, C.C.; Sung, T.Y.; Ho, S.S.; Peng, C.C.; Peng, R.Y. Supercritical fluid extracts of rosemary leaves exhibit potent anti-inflammation and anti-tumor effects. Biosci. Biotechnol. Biochem. 2007, 71, 2223-2232.
17. Poeckel, D.; Greiner, C.; Verhoff, M.; Rau, O.; Tausch, L.; Hornig, C.; Steinhilber, D.; Schubert-Zsilavecz, M.; Werz, O. Carnosic acid and carnosol potently inhibit human 5-lipoxygenase and suppress pro-inflammatory responses of stimulated human polymorphonuclear leukocytes. Biochem. Pharmacol. 2008, 76, 91-97.
18. Wijeratne, S.S.; Cuppett, S.L. Potential of rosemary (Rosemarinus officinalis L.) diterpenes in preventing lipid hydroperoxide-mediated oxidative stress in Caco-2 cells. J. Agric. Food Chem. 2007, 55, 1193-1199.
19. Yao, H.; Chen, Y.; Zhang, L.; He, X.; He, X.; Lian, L.; Wu, X.; Lan, P. Carnosol inhibits cell adhesion molecules and chemokine expression by tumor necrosis factor-alpha in human umbilical vein endothelial cells through the nuclear factor-eκb and mitogen-activated protein kinase pathways. Mol. Med. Rep. 2014, 9, 476-480.
20. Martin, D.; Rojo, A.I.; Salinas, M.; Diaz, R.; Gallardo, G.; Alam, J.; De Galarreta, C.M.; Cuadrado, A. Regulation of heme oxygenase-1 expression through the phosphatidylinositol 3-kinase/AKT pathway and the Nrf2 transcription factor in response to the antioxidant phytochemical carnosol. J. Biol. Chem. 2004, 279, 8919-8929.
21. Takahashi, T.; Tabuchi, T.; Tamaki, Y.; Kosaka, K.; Takikawa, Y.; Satoh, T. Carnosic acid and carnosol inhibit adipocyte differentiation in mouse 3T3-L1 cells through induction of phase2 enzymes and activation of glutathione metabolism. Biochem. Biophys. Res. Commun. 2009, 382, 549-554.
22. Huang, S.C.; Ho, C.T.; Lin-Shiau, S.Y.; Lin, J.K. Carnosol inhibits the invasion of B16/F10 mouse melanoma cells by suppressing metalloproteinase-9 through down-regulating nuclear factor-eκb and c-jun. Biochem. Pharmacol. 2005, 69, 221-232.
23. Subbaramaiah, K.; Cole, P.A.; Dannenberg, A.J. Retinoids and carnosol suppress cyclooxygenase-2 transcription by CREB-binding protein/p300-dependent and -independent mechanisms. Cancer Res. 2002, 62, 2522-2530.
24. Bai, N.; He, K.; Roller, M.; Lai, C.S.; Shao, X.; Pan, M.H.; Ho, C.T. Flavonoids and phenolic compounds from Rosmarinus officinalis. J. Agric. Food Chem. 2010, 58, 5363-5367.
25. Gebauer, M.; Saas, J.; Sohler, F.; Haag, J.; Soder, S.; Pieper, M.; Bartnik, E.; Beninga, J.; Zimmer, R.; Aigner, T. Comparison of the chondrosarcoma cell line SW1353 with primary human adult articular chondrocytes with regard to their gene expression profile and reactivity to IL-1beta. Osteoarthr. Cartil. 2005, 13, 697-708.
26. Goldring, M.B.; Berenbaum, F. The regulation of chondrocyte function by proinflammatory mediators: Prostaglandins and nitric oxide. Clin. Orthop. Relat. Res. 2004, S37-S46.
27. Goldring, S.R.; Goldring, M.B. The role of cytokines in cartilage matrix degeneration in osteoarthritis. Clin. Orthop. Relat. Res. 2004, S27-S36.
28. Sandell, L.J.; Xing, X.; Franz, C.; Davies, S.; Chang, L.W.; Patra, D. Exuberant expression of chemokine genes by adult human articular chondrocytes in response to IL-1β. Osteoarthr. Cartil. 2008, 16, 1560-1571.
29. Schwager, J.; Hoeller, U.; Wolfram, S.; Richard, N. Rose hip and its constituent galactolipids confer cartilage protection by modulating cytokine, and chemokine expression. BMC Complement. Altern. Med. 2011, 11, 105.
30. Sanchez, C.; Horcajada, M.N.; Membrez Scalfo, F.; Ameye, L.; Offord, E.; Henrotin, Y. Carnosol inhibits pro-inflammatory and catabolic mediators of cartilage breakdown in human osteoarthritic chondrocytes and mediates cross-talk between subchondral bone osteoblasts and chondrocytes. PLoS ONE 2015, 10, e0136118.
31. Ding, G.J.; Fischer, P.A.; Boltz, R.C.; Schmidt, J.A.; Colaianne, J.J.; Gough, A.; Rubin, R.A.; Miller, D.K. Characterization and quantitation of nf-kappab nuclear translocation induced by interleukin-1 and tumor necrosis factor-alpha. Development and use of a high capacity fluorescence cytometric system. J. Biol. Chem. 1998, 273, 28897-28905.
32. Del Bano, M.J.; Lorente, J.; Castillo, J.; Benavente-Garcia, O.; del Rio, J.A.; Ortuno, A.; Quirin, K.W.; Gerard, D. Phenolic diterpenes, flavones, and rosmarinic acid distribution during the development of leaves, flowers, stems, and roots of rosmarinus officinalis. Antioxidant activity. J. Agric. Food Chem. 2003, 51, 4247-4253.
33. Guerrero, I.C.; Andres, L.S.; Leon, L.G.; Machin, R.P.; Padron, J.M.; Luis, J.G.; Delgadillo, J. Abietane diterpenoids from salvia pachyphylla and S. clevelandii with cytotoxic activity against human cancer cell lines. J. Nat. Prod. 2006, 69, 1803-1805.
34. Lee, J.J.; Jin, Y.R.; Lim, Y.; Hong, J.T.; Kim, T.J.; Chung, J.H.; Yun, Y.P. Antiplatelet activity of carnosol is mediated by the inhibition of TXA2 receptor and cytosolic calcium mobilization. Vasc. Pharmacol. 2006, 45, 148-153.
35. Lee, J.J.; Jin, Y.R.; Lee, J.H.; Yu, J.Y.; Han, X.H.; Oh, K.W.; Hong, J.T.; Kim, T.J.; Yun, Y.P. Antiplatelet activity of carnosic acid, a phenolic diterpene from Rosmarinus officinalis. Planta Med. 2007, 73, 121-127.
36. Gilroy, D.W.; Lawrence, T.; Perretti, M.; Rossi, A.G. Inflammatory resolution: New opportunities for drug discovery. Nat. Rev. Drug Discov. 2004, 3, 401-416.
37. Singletary, K.W. Rosemary extract and carnosol stimulate rat liver glutathione-s-transferase and quinone reductase activities. Cancer Lett. 1996, 100, 139-144.
38. Amin, A.R.; Attur, M.; Patel, R.N.; Thakker, G.D.; Marshall, P.J.; Rediske, J.; Stuchin, S.A.; Patel, I.R.; Abramson, S.B. Superinduction of cyclooxygenase-2 activity in human osteoarthritis-affected cartilage. Influence of nitric oxide. J. Clin. Investig. 1997, 99, 1231-1237.
39. Murrell, G.A.; Jang, D.; Williams, R.J. Nitric oxide activates metalloprotease enzymes in articular cartilage. Biochem. Biophys. Res. Commun. 1995, 206, 15-21.
40. Vuolteenaho, K.; Moilanen, T.; Knowles, R.G.; Moilanen, E. The role of nitric oxide in osteoarthritis. Scand. J. Rheumatol. 2007, 36, 247-258.
41. Melchiorri, C.; Meliconi, R.; Frizziero, L.; Silvestri, T.; Pulsatelli, L.; Mazzetti, I.; Borzi, R.M.; Uguccioni, M.; Facchini, A. Enhanced and coordinated in vivo expression of inflammatory cytokines and nitric oxide synthase by chondrocytes from patients with osteoarthritis. Arthritis Rheum. 1998, 41, 2165-2174.
42. Richard, N.; Porath, D.; Radspieler, A.; Schwager, J. Effects of resveratrol, piceatannol, tri-acetoxystilbene, and genistein on the inflammatory response of human peripheral blood leukocytes. Mol. Nutr. Food Res. 2005, 49, 431-442.
43. D'Acquisto, F.; Cicatiello, L.; Iuvone, T.; Ialenti, A.; Ianaro, A.; Esumi, H.; Weisz, A.; Carnuccio, R. Inhibition of inducible nitric oxide synthase gene expression by glucocorticoid-induced protein(s) in lipopolysaccharide-stimulated J774 cells. Eur. J. Pharmacol. 1997, 339, 87-95.