The antioxidant flavonoid monoHER provides efficient protection and induces the innate Nrf2 mediated adaptation in endothelial cells subjected to oxidative stress

PharmaNutrition

Volumn 2, Issue 3, 2014, Pages 69-74

  Lemmens, Kristien J A ^a   Sthijns, Mireille M J P E ^a   van der Vijgh, Wim J F ^a   Bast, Aalt ^a   Haenen, Guido R M M ^a  

^a MAASTRICHT UNIVERSITY   (Netherlands)

Author keywords

7 Mono O ( hydroxyethyl) rutoside (PubChem CID 5464100); Adaptation; HUVEC; Keap1; MonoHER; Nrf2; Reactive oxygen species

Indexed keywords

7 MONO O (BETA HYDROXYETHYL)RUTOSIDE; ANTIOXIDANT; FLAVONOID; HEME OXYGENASE 1; HYDROGEN PEROXIDE; KELCH LIKE ECH ASSOCIATED PROTEIN 1; REACTIVE OXYGEN METABOLITE; TRANSCRIPTION FACTOR NRF2; UNCLASSIFIED DRUG;

ADAPTATION; ARTICLE; CELL PROTECTION; CONTROLLED STUDY; DRUG EFFECT; GENE EXPRESSION; HO 1 GENE; HUMAN; HUMAN CELL; HUMAN CELL CULTURE; MASS SPECTROMETRY; OXIDATIVE STRESS; PRIORITY JOURNAL; UMBILICAL VEIN ENDOTHELIAL CELL; UPREGULATION;

EID: 84905389338     PISSN: None     EISSN: 22134344     Source Type: Journal    
DOI: 10.1016/j.phanu.2014.05.003     Document Type: Article

References (24)

1. Bast A., Haenen G.R., Doelman C.J. Oxidants and antioxidants: state of the art. American Journal of Medicine 1991, 91:2S-13S. http://www.ncbi.nlm.nih.gov/pubmed/1928207, 10.1016/0002-9343(91)90278-6.
2. Sies H. Strategies of antioxidant defense. European Journal of Biochemistry/FEBS 1993, 215:213-219. http://www.ncbi.nlm.nih.gov/pubmed/7688300, 10.1111/j.1432-1033.1993.tb18025.x.
3. Chaudiereand J., Ferrari-Iliou R. Intracellular antioxidants: from chemical to biochemical mechanisms. Food and Chemical Toxicology 1999, 37:949-962. 10.1016/S0278-6915(99)00090-3.
4. Sthijns M.M., Randall M.J., Bast A., Haenen G.R. Adaptation to acrolein through upregulating the protection by glutathione in human bronchial epithelial cells: the materialization of the hormesis concept. Biochemical and Biophysical Research Communications 2014, 446:1029-1034. http://www.ncbi.nlm.nih.gov/pubmed/24667599.
5. Kobayashi M., Yamamoto M. Nrf2-Keap1 regulation of cellular defense mechanisms against electrophiles and reactive oxygen species. Advances in Enzyme Regulation 2006, 46:113-140. http://www.ncbi.nlm.nih.gov/pubmed/16887173, 10.1016/j.advenzreg.2006.01.007.
6. Vetrani C., Costabile G., Di Marino L., Rivellese A.A. Nutrition and oxidative stress: a systematic review of human studies. International Journal of Food Sciences and Nutrition 2013, 64:312-326. http://www.ncbi.nlm.nih.gov/pubmed/23121370, 10.3109/09637486.2012.738651.
7. Boots A.W., Haenen G.R., Bast A. Health effects of quercetin: from antioxidant to nutraceutical. European Journal of Pharmacology 2008, 585:325-337. http://www.ncbi.nlm.nih.gov/pubmed/18417116, 10.1016/j.ejphar.2008.03.008.
8. Rietjens S.J., Bast A., de Vente J., Haenen G.R. The olive oil antioxidant hydroxytyrosol efficiently protects against the oxidative stress-induced impairment of the NObullet response of isolated rat aorta. American Journal of Physiology. Heart and Circulatory Physiology 2007, 292:H1931-H1936. http://www.ncbi.nlm.nih.gov/pubmed/17172277.
9. Haenen G.R., Jansen F.P., Bast A. The antioxidant properties of five O-(β-hydroxyethyl)-rutosides of the flavonoid mixture venoruton. Phlebology 1993, 1:10-17.
10. Lemmens K.J., van de Wier B., Vaes N., Ghosh M., van Zandvoort M.A., van der Vijgh W.J., Bast A., Haenen G.R. The flavonoid 7-mono-O-(beta-hydroxyethyl)-rutoside is able to protect endothelial cells by a direct antioxidant effect. Toxicology in Vitro: An International Journal Published in Association with BIBRA 2014, 28:538-543. http://www.ncbi.nlm.nih.gov/pubmed/24412621, 10.1016/j.tiv.2013.12.019.
11. Cesarone M.R., Belcaro G., Pellegrini L., Ledda A., Vinciguerra G., Ricci A., Gizzi G., Ippolito E., Fano F., Dugall M., Acerbi G., Cacchio M., Di Renzo A., Hosoi M., Stuard S., Corsi M. Circulating endothelial cells in venous blood as a marker of endothelial damage in chronic venous insufficiency: improvement with venoruton. Journal of Cardiovascular Pharmacology and Therapeutics 2006, 11:93-98. http://www.ncbi.nlm.nih.gov/pubmed/16703224, 10.1177/107424840601100109.
12. Miller E.W., Dickinson B.C., Chang C.J. Aquaporin-3 mediates hydrogen peroxide uptake to regulate downstream intracellular signaling. Proceedings of the National Academy of Sciences of the United States of America 2010, 107:15681-15686. http://www.ncbi.nlm.nih.gov/pubmed/20724658, 10.1073/pnas.1005776107.
13. Itoh K., Mimura J., Yamamoto M. Discovery of the negative regulator of Nrf2, Keap1: a historical overview. Antioxidants & Redox Signaling 2010, 13:1665-1678. http://www.ncbi.nlm.nih.gov/pubmed/20446768, 10.1089/ars.2010.3222.
14. Rushmore T.H., Morton M.R., Pickett C.B. The antioxidant responsive element. Activation by oxidative stress and identification of the DNA consensus sequence required for functional activity. Journal of Biological Chemistry 1991, 266:11632-11639. http://www.ncbi.nlm.nih.gov/pubmed/1646813.
15. Itoh K., Chiba T., Takahashi S., Ishii T., Igarashi K., Katoh Y., Oyake T., Hayashi N., Satoh K., Hatayama I., Yamamoto M., Nabeshima Y. An Nrf2/small Maf heterodimer mediates the induction of phase II detoxifying enzyme genes through antioxidant response elements. Biochemical and Biophysical Research Communications 1997, 236:313-322. http://www.ncbi.nlm.nih.gov/pubmed/9240432, 10.1006/bbrc.1997.6943.
16. Itoh K., Tong K.I., Yamamoto M. Molecular mechanism activating Nrf2-Keap1 pathway in regulation of adaptive response to electrophiles. Free Radical Biology & Medicine 2004, 36:1208-1213. http://www.ncbi.nlm.nih.gov/pubmed/15110385, 10.1016/j.freeradbiomed.2004.02.075.
17. Neumann H.A., Carlsson K., Brom G.H. Uptake and localisation of O-(beta-hydroxyethyl)-rutosides in the venous wall, measured by laser scanning microscopy. European Journal of Clinical Pharmacology 1992, 43:423-426. http://www.ncbi.nlm.nih.gov/pubmed/1451724, 10.1007/BF02220620.
18. Bastand A., Haenen G.R. The toxicity of antioxidants and their metabolites. Environmental Toxicology and Pharmacology 2002, 11:251-258. http://www.ncbi.nlm.nih.gov/pubmed/21782609, 10.1016/S1382-6689(01)00118-1.
19. Jacobs H., van der Vijgh W.J., Koek G.H., Draaisma G.J., Moalin M., van Strijdonck G.P., Bast A., Haenen G.R. Characterization of the glutathione conjugate of the semisynthetic flavonoid monoHER. Free Radical Biology & Medicine 2009, 46:1567-1573. http://www.ncbi.nlm.nih.gov/pubmed/19272444, 10.1016/j.freeradbiomed.2009.02.031.
20. Jacobs H., Moalin M., Bast A., van der Vijgh W.J., Haenen G.R. An essential difference between the flavonoids monoHER and quercetin in their interplay with the endogenous antioxidant network. PLoS ONE 2010, 5:e13880. http://www.ncbi.nlm.nih.gov/pubmed/21079733, 10.1371/journal.pone.0013880.
21. Hollandand R., Fishbein J.C. Chemistry of the cysteine sensors in Kelch-like ECH-associated protein 1. Antioxidants & Redox Signaling 2010, 13:1749-1761. http://www.ncbi.nlm.nih.gov/pubmed/20486763, 10.1089/ars.2010.3273.
22. Itoh K., Wakabayashi N., Katoh Y., Ishii T., Igarashi K., Engel J.D., Yamamoto M. Keap1 represses nuclear activation of antioxidant responsive elements by Nrf2 through binding to the amino-terminal Neh2 domain. Genes & Development 1999, 13:76-86. http://www.ncbi.nlm.nih.gov/pubmed/9887101, 10.1101/gad.13.1.76.
23. Arinzeand I.J., Kawai Y. Transcriptional activation of the human Galphai2 gene promoter through nuclear factor-kappaB and antioxidant response elements. Journal of Biological Chemistry 2005, 280:9786-9795. http://www.ncbi.nlm.nih.gov/pubmed/15640523, 10.1074/jbc.M414006200.
24. Kwak M.K., Kensler T.W., Casero R.A. Induction of phase 2 enzymes by serum oxidized polyamines through activation of Nrf2: effect of the polyamine metabolite acrolein. Biochemical and Biophysical Research Communications 2003, 305:662-670. http://www.ncbi.nlm.nih.gov/pubmed/12763045, 10.1016/S0006-291X(03)00834-9.