A novel di terpene para-hydroquinone compound derived from cryptoquinone protects neuronal cells against oxidative stress and activates the Nrf2/ARE pathway

Neuroscience Letters

Volumn 548, Issue , 2013, Pages 132-136

  Sasaki, Shunsuke ^a   Tozawa, Terumasa ^a   Sugamoto, Kazuhiro ^b   Matsushita, Yoh ichi ^b   Satoh, Takumi ^a  

^a IWATE UNIVERSITY   (Japan)

^b UNIVERSITY OF MIYAZAKI   (Japan)

Author keywords

ARE; Cryptoquinone; DA1; Nrf2; Para Hydroquinone; Pro electrophilic drugs

Indexed keywords

11,14 DIHYDROXY 8,11,13 ABIETARIENE; 2 METHYHYDROQUINONE; GLUTATHIONE; HYDROQUINONE DERIVATIVE; STR8; TRANSCRIPTION FACTOR NRF2; UNCLASSIFIED DRUG;

ANTIOXIDANT RESPONSIVE ELEMENT; ARTICLE; CONTROLLED STUDY; ELECTROPHILIC STRESS; HUMAN; HUMAN CELL; NERVE CELL; NEUROPROTECTION; OXIDATIVE STRESS; PRIORITY JOURNAL;

3-(4,5-DIMETHYLTHIAZOL-2-YL)-2,5-DIPHENYL TETRAZOLIUM BROMIDE; ANTIOXIDANT-RESPONSIVE ELEMENT; ARE; CA; CARNOSIC ACID; CRYPTOQUINONE; DA1; DIMETHYL SULFOXIDE; DMSO; FDA; FLUORESCEIN DIACETATE; GCLC; GLUTAMYL CYSTEINE LIGASE CATALYTIC SUBUNIT; GLUTATHIONE S-TRANSFERASE; GSH; GSSG; GST; H(2)O(2); HEME OXYGENASE-1; HO-1; HYDROGEN PEROXIDE; MTT; NADPH QUINONE OXIDOREDUCTASE 1; NQO-1; NRF2; OXIDIZED GLUTATHIONE; PARA-HYDROQUINONE; PED; PRO-ELECTROPHILIC DRUG; PRO-ELECTROPHILIC DRUGS; REDUCED GLUTATHIONE; REVERSE TRANSCRIPTION-POLYMERASE CHAIN REACTION; RT-PCR; SD; STANDARD DEVIATION; STR; STRONGYLOPHORINE;

APOPTOSIS; CARBOXYLIC ESTER HYDROLASES; CELL LINE; CELLS, CULTURED; HUMANS; HYDROQUINONES; NEURONS; NEUROPROTECTIVE AGENTS; NF-E2-RELATED FACTOR 2; OXIDATIVE STRESS; SIGNAL TRANSDUCTION;

EID: 84880135556     PISSN: 03043940     EISSN: 18727972     Source Type: Journal    
DOI: 10.1016/j.neulet.2013.04.047     Document Type: Article

References (39)

1. Calkins M.J., Townsend J.A., Johnson D.A., Johnson J.A. Cystamine protects from 3-nitropropionic acid lesioning via induction of nf-e2 related factor 2 mediated transcription. Exp. Neurol. 2010, 224:307-317.
2. Groeger A.L., Freeman B.A. Signaling actions of electrophiles: anti-inflammatory therapeutic candidates. Mol. Interv. 2010, 10:39-50.
3. Itoh K., Tong K.I., Yamamoto M. Molecular mechanism activating Nrf2-Keap1 pathway in regulation of adaptive response to electrophiles. Free Radic. Biol. Med. 2004, 36:1208-1213.
4. Jiang H., Tian X., Guo Y., Duan W., Bu H., Li C. Activation of nuclear factor erythroid 2-related factor 2 cytoprotective signaling by curcumin protect primary spinal cord astrocytes against oxidative toxicity. Biol. Pharm. Bull. 2011, 34:1194-1197.
5. Kofujita H., Ota M., Takahashi K., Kawai Y., Hayashi Y. A diterpene quinone from the bark of Cryptomeria japonica. Phytochemistry 2002, 61:895-898.
6. Kosaka K., Mimura J., Itoh K., Satoh T., Shimojo Y., Kitajima C., Maruyama A., Yamamoto M., Shirasawa T. Role of p62/ZIP in the neurite outgrowth by carnosic acid in PC12h cells. J. Biochem. 2010, 147:73-82.
7. Kraft A.D., Johnson D.A., Johnson J.A. Nuclear factor E2-related factor 2-dependent antioxidant response element activation by tert-butylhydroquinone and sulforaphane occurring preferentially in astrocytes conditions neurons against oxidative insult. J. Neurosci. 2004, 24:1101-1112.
8. Kwak M.K., Itoh K., Yamamoto M., Sutter T.R., Kensler T.W. Role of transcription factor Nrf2 in the induction of hepatic phase 2 and antioxidative enzymes in vivo by the cancer chemoprotective agent, 3H-1, 2-dimethiole-3-thione. Mol. Med. 2001, 7:135-145.
9. Mandel M.N., Patlolla J.M., Zheng L., Agbaga M.P., Tran J.T., Wicker L., Kasus-Jacobi A., Elliott M.H., Rao C.V., Anderson R.E. Curcumin protects retinal cells from light-and oxidant stress-induced cell death. Free Radic. Biol. Med. 2009, 46:672-679.
10. Matsushita Y., Iwakiri Y., Yoshida S., Sugamoto K., Matsui T. Synthesis of 12-deoxyroyleanone, cryptoquinone, 11,14-dihydroxy-8,11,13-abietatrien-7-one, and related derivatives from dehydroabietic acid. Tetrahedron Lett. 2005, 46:3629-3632.
11. Mattson M.P., Cheng A. Neurohormetic phytochemicals: low-dose toxins that induce adaptive neuronal stress response. Trends Neurosci. 2006, 29:632-639.
12. Mimura J., Kosaka K., Maruyama A., Satoh T., Harada N., Yoshida H., Satoh K., Yamamoto M., Itoh K. Nrf2 regulates NGF mRNA induction by carnosic acid in T98G glioblastoma cells and normal human astrocytes. J. Biochem. 2010, 150:209-217.
13. Nakamura T., Lipton S.A. Cell death: protein misfolding and neurodegenerative diseases. Apoptosis 2009, 14:455-468.
14. Park H.M., Kim J.A., Kwak M.K. Protection against amyloid beta cytotoxicity by sulforaphane: role of the proteasome. Arch. Pharm. Res. 2009, 32:109-115.
15. Rezaie T., McKercher S.R., Kosaka K., Seki M., Wheeler L., Viswanath V., Chun T., Joshi R., Valencia M., Sasaki S., Tozawa T., Satoh T., Lipton S.A. Protective effect of carnosic acid, a pro-electrophilic compound, in models of oxidative stress and light-induced retinal degeneration. Invest. Ophthalmol. Vis. Sci. 2012, 53:7847-7854.
16. Sasaki S., Tozawa T., Van Wagoner R.M., Ireland C.M., Harper M.K., Satoh T. Strongylophorine-8, a pro-electrophilic compound from the marine sponge Petrosia (Strongylophora) corticata, provides neuroprotection through Nrf2/ARE pathway. Biochem. Biophys. Res. Commun. 2011, 415:6-10.
17. Satoh T., Akhtar M.W., Lipton S.A. Combating oxidative/nitrosative stress with electrophilic counterattack strategies. Oxidative Stress and Redox Regulation 2013, Springer, (in press). U. Jakob, D. Reichmann (Eds.).
18. Satoh T., Baba M., Nakatsuka D., Ishikawa Y., Aburatani H., Furuta K., Ishikawa T., Hatanaka H., Suzuki M., Watanabe Y. Role of heme oxygenase-1 protein in the neuroprotective effects by cyclopentenone prostaglandin derivatives as a sustained phase of neuronal survival promoting mechanism under oxidative stress. Eur. J. Neurosci. 2003, 17:2249-2255.
19. Satoh T., Furuta K., Tomokiyo K., Nakatsuka D., Miura M., Hatanaka M., Ikuta K., Suzuki M., Watanabe Y. Facilitatory roles of novel compounds designed from cyclopentenone prostaglandins on the neurite outgrowth-promoting activities of NGF. J. Neurochem. 2000, 75:1092-1102.
20. Satoh T., Furuta K., Tomokiyo K., Namura S., Nakatsuka D., Sugie Y., Ishikawa Y., Hatanaka H., Suzuki M., Watanabe Y. Neurotrophic actions of novel compounds designed from cyclopentenone prostaglandins. J. Neurochem. 2001, 77:50-62.
21. Satoh T., Harada N., Hosoya T., Tohyama K., Yamamoto M., Itoh K. Keap1/Nrf2 system regulates neuronal survival as revealed through study of keap1 gene knockout mice. Biochem. Biophys. Res. Commun. 2009, 380:298-302.
22. Satoh T., Ishige K.K., Sagara Y. Protective effects on neuronal cells of mouse afforded by ebselen against oxidative stress at multiple steps. Neurosci. Lett. 2004, 371:1-5.
23. Satoh T., Izumi M. Neuroprotective effects of phenylenediamine derivatives independent of an antioxidant pathway in neuronal HT22 cells. Neurosci. Lett. 2007, 418:102-105.
24. Satoh T., Izumi M., Inukai Y., Tsutumi Y., Nakayama N., Kosaka K., Kitajima C., Itoh K., Yokoi T., Shirasawa T. Carnosic acid protects neuronal HT22 cells through activation of the antioxidant-responsive element in free carboxylic acid- and catechol hydroxyl moieties-dependent manners. Neurosci. Lett. 2008, 434:260-265.
25. Satoh T., Kosaka K., Itoh K., Kobayashi A., Yamamoto M., Shimojo Y., Kitajima C., Cui J., Kamins J., Okamoto S., Shirasawa T., Lipton S.A. Carnosic acid, a catechol-type electrophilic compound, protects neurons both in vitro and in vivo through activation of the Keap1/Nrf2 pathway via S-alkylation of specific cysteines. J. Neurochem. 2008, 104:1116-1131.
26. Satoh T., Lipton S.A. Redox regulation of neuronal survival by electrophilic compounds. Trends Neurosci. 2007, 30:37-45.
27. Satoh T., Okamoto S., Cui J., Watanabe Y., Furuta K., Suzuki M., Tohyama K., Lipton S.A. Activation of the Keap1/Nrf2 pathway for neuroprotection by electrophilic phase II inducers. Proc. Natl. Acad. Sci. U.S.A. 2006, 103:768-773.
28. Satoh T., Reraie T., Seki M., Sunico C.R., Tabuchi T., Kitagaw T., Yanagitai M., Senzaki M., Kosegawa C., Taira H., Mckercher S.R., Hoffman J.K., Roth G.P., Lipton S.A. Dual neuroprotective pathways of a pro-electrophilic compound via HSF-1-activated heat-shock proteins and Nrf2-activated phase 2 antioxidant response enzymes. J. Neurochem. 2011, 19:569-578.
29. Satoh T., Saitoh S., Hosaka H., Kosaka K. Simple ortho- and para-hydroquinones as neuroprotective compounds against oxidative stress associated with a specific transcriptional activation. Biochem. Biophys. Res. Commun. 2009, 379:537-541.
30. Shah Z.A., Li R.C., Ahmad A.S., Kensler T.W., Yamamoto M., Biswal S., Doré S. The flavanol (-)-epicatechin prevents stroke damage through the Nrf2/HO1 pathway. J. Cereb. Blood Flow Metab. 2010, 30:1951-1961.
31. Son T.G., Camandola S., Arumugam T.V., Cutler R.G., Telljohann R.S., Mughal M.R., Moore T.A., Luo W., Yu Q.S., Johnson D.A., Johnson J.A., Greig N.H., Mattson M.P., Plumbagin a novel Nrf2/ARE activator, protects against cerebral ischemia. J. Neurochem. 2010, 112:1316-1326.
32. 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 phase 2 enzymes and activation of glutathione metabolism. Biochem. Biophys. Res. Commun. 2009, 382:549-554.
33. Talalay P. Chemoprotection against cancer by induction of phase 2 enzymes. Biofactors 2000, 12:5-11.
34. Tamaki Y., Tabuchi T., Takahashi T., Kosaka K., Satoh T. Activated glutathione metabolism participates in protective effects of carnosic acid against oxidative stress in neuronal HT22 cells. Planta Med. 2010, 76:683-688.
35. Tan N., Kaloga M., Radtke O.A., Kiderlen A.F., Öksüz S., Ulubelen A., Kolodziej H. Abietane diterpenoids and triterpenoic acids from Salvia cilicica and their antileishmanial activities. Phytochemistry 2002, 61:881-884.
36. Wang T., Takikawa Y., Satoh T., Yoshioka Y., Kosaka K., Tatemichi Y., Suzuki K. Carnosic acid prevents obesity and hepatic steatosis in ob/ob mice. Hep. Res. 2011, 41:87-92.
37. Wang T., Takikawa Y., Tabuchi T., Satoh T., Kosaka K., Suzuki K. Carnosic acid (CA) prevents lipid accumulation in hepatocytes through the EGFR/MAPK pathway. J. Gastroenterol. 2012, 47:805-813.
38. Yanagitai M., Kitagawa T., Okawa K., Koyama H., Satoh T. Phenylenediamine derivatives induce GDF-15/MIC-1 and inhibit adipocyte differentiation of mouse 3T3-L1 cells. Biochem. Biophys. Res. Commun. 2012, 417:294-298.
39. Yanagitai M., Kitagawa T., Takenouchi T., Kitani H., Satoh T. Carnosic acid, a pro-electrophilic compound, inhibits LPS-induced activation of microglia. Biochem. Biophys. Res. Commun. 2012, 417:22-26.