Hydroxycinnamic acids in crepidiastrum denticulatum protect oxidative stress-induced retinal damage

Journal of Agricultural and Food Chemistry

Volumn 62, Issue 6, 2014, Pages 1310-1323

  Ahn, Hong Ryul ^a   Lee, Hee Ju ^a   Kim, Kyung A ^a   Kim, Chul Young ^b   Nho, Chu Won ^a   Jang, Holim ^a,c   Pan, Cheol Ho ^a   Lee, Chang Yong ^c   Jung, Sang Hoon ^a  

^a Korea Institute of Science and Technology   (South Korea)

^b Hanyang University   (South Korea)

^c Department of Obstetrics Gynecology   (United States)

Author keywords

chicoric acid; Crepidiastrum denticulatum; glaucoma; neuroprotection; RGC 5

Indexed keywords

EYE PROTECTION;

CHICORIC ACIDS; CREPIDIASTRUM DENTICULATUM; GLAUCOMA; NEUROPROTECTION; RGC-5;

OPHTHALMOLOGY;

RATTUS; YOUNGIA DENTICULATA;

3,5-DICAFFEOYLQUINIC ACID; CAFFEIC ACID DERIVATIVE; CHLOROGENIC ACID; CICHORIC ACID; COUMARIC ACID; DRUG DERIVATIVE; ISOCHLOROGENIC ACID; N METHYLASPARTIC ACID; NEUROPROTECTIVE AGENT; PLANT EXTRACT; SUCCINIC ACID DERIVATIVE;

ANIMAL; APOPTOSIS; ARTICLE; ASTERACEAE; CHEMISTRY; DISEASE MODEL; DRUG EFFECT; GLAUCOMA; INSTITUTE FOR CANCER RESEARCH MOUSE; LIPID PEROXIDATION; MALE; MOUSE; NERVE CRUSH; OPTIC NERVE; OXIDATIVE STRESS; RAT; RETINA DISEASE; SPRAGUE DAWLEY RAT;

ANIMALS; APOPTOSIS; ASTERACEAE; CAFFEIC ACIDS; CHLOROGENIC ACID; COUMARIC ACIDS; DISEASE MODELS, ANIMAL; GLAUCOMA; LIPID PEROXIDATION; MALE; MICE; MICE, INBRED ICR; N-METHYLASPARTATE; NERVE CRUSH; NEUROPROTECTIVE AGENTS; OPTIC NERVE; OXIDATIVE STRESS; PLANT EXTRACTS; RATS; RATS, SPRAGUE-DAWLEY; RETINAL DISEASES; SUCCINATES;

EID: 84894122362     PISSN: 00218561     EISSN: 15205118     Source Type: Journal    
DOI: 10.1021/jf4046232     Document Type: Article

References (60)

1. Akihisa, T.; Franzblau, S. G.; Ukiya, M.; Okuda, H.; Zhang, F.; Yasukawa, K.; Suzuki, T.; Kimura, Y. Antitubercular activity of triterpenoids from Asteraceae flowers Biol. Pharm. Bull. 2005, 28, 158-160
2. Yun, J. H.; Lee, S. B.; Lee, H. J.; Kim, C. Y.; Kim, M. A.; Sohn, Y. C.; Nho, C. W. Bi-functional induction of the quinone reductase and cytochrome P450 1A1 by youngiasides via Nrf2-ARE and AhR-XRE pathways Biol. Pharm. Bull. 2010, 33, 1650-1657
3. Kang, K.; Jho, E. H.; Lee, H. J.; Oidovsambuu, S.; Yun, J. H.; Kim, C. Y.; Yoo, J. H.; Kim, Y. J.; Kim, J. H.; Ahn, S. Y.; Nho, C. W. Youngia denticulata protects against oxidative damage induced by tert-butylhydroperoxide in HepG2 cells J. Med. Food 2011, 14, 1198-1207
4. Maeda, G.; Takara, K.; Wada, K.; Oki, T.; Masuda, M.; Ichiba, T.; Chuda, Y.; Ono, H.; Suda, I. Evaluation of antioxidant activity of vegetables from Okinawa prefecture and determination of some antioxidative compound Food Sci. Technol. Res. 2006, 12, 8-14
5. Meyer, A. S.; Frankel, E. N. Antioxidant activity of hydroxycinnamic acids on human low-density lipoprotein oxidation Methods Enzymol. 2001, 335, 256-265
6. Tousch, D.; Lajoix, A. D.; Hosy, E.; Azay-Milhau, J.; Ferrare, K.; Jahannault, C.; Cros, G.; Petit, P. Chicoric acid, a new compound able to enhance insulin release and glucose uptake Biochem. Biophys. Res. Commun. 2008, 377, 131-135
7. Kim, H. G.; Oh, M. S. Natural products as potential anticonvulsants: caffeoylquinic acids Arch. Pharm. Res. 2012, 35, 389-392
8. Nakajima, Y.; Shimazawa, M.; Mishima, S.; Hara, H. Water extract of propolis and its main constituents, caffeoylquinic acid derivatives, exert neuroprotective effects via antioxidant actions Life Sci. 2007, 80, 370-377
9. Chu, K. O.; Chan, K. P.; Wang, C. C.; Chu, C. Y.; Li, W. Y.; Choy, K. W.; Rogers, M. S.; Pang, C. P. Green tea catechins and their oxidative protection in the rat eye J. Agric. Food Chem. 2010, 58, 1523-1534
10. Sacca, S. C.; Izzotti, A.; Rossi, P.; Traverso, C. Glaucomatous outflow pathway and oxidative stress Exp. Eye Res. 2007, 84, 389-399
11. Tanaka, J.; Nakanishi, T.; Ogawa, K.; Tsuruma, K.; Shimazawa, M.; Shimoda, H.; Hara, H. Purple rice extract and anthocyanidins of the constituents protect against light-induced retinal damage in vitro and in vivo J. Agric. Food Chem. 2011, 59, 528-536
12. Kumar, D. M.; Agarwal, N. Oxidative stress in glaucoma: A burden of evidence J. Glaucoma 2007, 16, 334-343
13. Jung, S. H.; Kim, B. J.; Lee, E. H.; Osborne, N. N. Isoquercitrin is the most effective antioxidant in the plant Thuja orientalis and able to counteract oxidative-induced damage to a transformed cell line (RGC-5 cells) Neurochem. Int. 2010, 57, 713-721
14. Kim, K. A.; Kang, K. D.; Lee, E. H.; Nho, C. W.; Jung, S. H. Edible wild vegetable, Gymnaster koraiensis protects retinal ganglion cells against oxidative stress Food Chem. Toxicol. 2011, 49, 2131-2143
15. Kalt, W.; Hanneken, A.; Milbury, P.; Tremblay, F. Recent research on polyphenolics in vision and eye health J. Agric. Food Chem. 2010, 58, 4001-4007
16. Quigley, H. A. Number of people with glaucoma worldwide Br. J. Ophthalmol. 1996, 80, 389-393
17. Nucci, C.; Tartaglione, R.; Rombola, L.; Morrone, L. A.; Fazzi, E.; Bagetta, G. Neurochemical evidence to implicate elevated glutamate in the mechanisms of high intraocular pressure (IOP)-induced retinal ganglion cell death in rat Neurotoxicology 2005, 26, 935-941
18. Levin, L. A.; Peeples, P. History of neuroprotection and rationale as a therapy for glaucoma Am. J. Manag. Care 2008, 14, S11-14
19. Leske, M. C.; Heijl, A.; Hussein, M.; Bengtsson, B.; Hyman, L.; Komaroff, E. Factors for glaucoma progression and the effect of treatment: the early manifest glaucoma trial Arch. Ophthalmol. 2003, 121, 48-56
20. Baltmr, A.; Duggan, J.; Nizari, S.; Salt, T. E.; Cordeiro, M. F. Neuroprotection in glaucoma-Is there a future role? Exp. Eye Res. 2010, 91, 554-566
21. Marcic, T. S.; Belyea, D. A.; Katz, B. Neuroprotection in glaucoma: A model for neuroprotection in optic neuropathies Curr. Opin. Ophthalmol. 2003, 14, 353-356
22. Adegawa, S.; Miyase, T.; Fukushima, S. Sesquiterpene glycosides from Youngia denticulata (Houtt) Kitam Chem. Pharm. Bull. 1986, 34, 3769-3773
23. Carnat, A.; Heitz, A.; Fraisse, D.; Carnat, A. P.; Lamaison, J. L. Major dicaffeoylquinic acids from Artemisia vulgaris Fitoterapia 2000, 71, 587-589
24. Wang, T.; Jiang, X.; Yang, L.; Wu, S. pH-gradient counter-current chromatography isolation of natural antioxidant chlorogenic acid from Lonicera japonica Thumb. using an upright coil planet centrifuge with three multi-layer coils connected in series J. Chromatogr. A 2008, 1180, 53-58
25. Krishnamoorthy, R. R.; Agarwal, P.; Prasanna, G.; Vopat, K.; Lambert, W.; Sheedlo, H. J.; Pang, I. H.; Shade, D.; Wordinger, R. J.; Yorio, T.; Clark, A. F.; Agarwal, N. Characterization of a transformed rat retinal ganglion cell line Brain Res. Mol. Brain Res. 2001, 86, 1-12
26. Van Bergen, N. J.; Wood, J. P. M.; Chidlow, G.; Trounce, I. A.; Casson, R. J.; Ju, W. K.; Weinreb, R. N.; Crowston, J. G. Recharacterization of the RGC-5 retinal ganglion cell line Invest. Ophthalmol. Vis. Sci. 2009, 50, 4267-4272
27. Mosmann, T. Rapid colorimetric assay for cellular growth and survival: application to proliferation and cytotoxicity assays J. Immunol. Methods 1983, 65, 55-63
28. Shimazawa, M.; Nakajima, Y.; Mashima, Y.; Hara, H. Docosahexaenoic acid (DHA) has neuroprotective effects against oxidative stress in retinal ganglion cells Brain Res. 2009, 1251, 269-275
29. Kim, K. A.; Kim, S. M.; Kang, S. W.; Il Jeon, S.; Um, B. H.; Jung, S. H. Edible seaweed, Eisenia bicyclis, protects retinal ganglion cells death caused by oxidative stress Mar. Biotechnol. 2012, 14, 383-395
30. Kang, K. D.; Majid, A. S. A.; Kim, K. A.; Kang, K.; Ahn, H. R.; Nho, C. W.; Jung, S. H. Sulbutiamine counteracts trophic factor deprivation induced apoptotic cell death in transformed retinal ganglion cells Neurochem. Res. 2010, 35, 1828-1839
31. Huang, H.-L.; Wu, S.-L.; Liao, H.-F.; Jiang, C.-M.; Huang, R.-L.; Chen, Y.-Y.; Yang, Y.-C.; Chen, Y.-J. Induction of apoptosis by three marine algae through generation of reactive oxygen species in human leukemic cell lines J. Agric. Food Chem. 2005, 53, 1776-1781
32. Zhang, B.; Osborne, N. N. Oxidative-induced retinal degeneration is attenuated by epigallocatechin gallate Brain Res. 2006, 1124, 176-187
33. Jung, S. H.; Kang, K. D.; Ji, D.; Fawcett, R. J.; Safa, R.; Kamalden, T. A.; Osborne, N. N. The flavonoid baicalin counteracts ischemic and oxidative insults to retinal cells and lipid peroxidation to brain membranes Neurochem. Int. 2008, 53, 325-337
34. Inokuchi, Y.; Shimazawa, M.; Nakajima, Y.; Suemori, S.; Mishima, S.; Hara, H. Brazilian green propolis protects against retinal damage in vitro and in vivo J. Evidence-Based Complementary Altern. Med. 2006, 3, 71-77
35. Kwong, J. M.; Lam, T. T. N -Methyl- d -aspartate (NMDA) induced apoptosis in adult rabbit retinas Exp. Eye Res. 2000, 71, 437-444
36. Park, Y. W.; Chae, S. H.; Lee, J.; Kwon, O. J.; Shin, J. P.; Jeon, C. J.; Kim, S. Y. N -Methyl- d -aspartate (NMDA)-induced apoptosis in rabbit retina J. Korean Ophthalmol. Soc. 2008, 49, 1146-1153
37. Li, Y.; Schlamp, C. L.; Nickells, R. W. Experimental induction of retinal ganglion cell death in adult mice Invest. Ophthalmol. Vis. Sci. 1999, 40, 1004-1008
38. Danias, J.; Lee, K. C.; Zamora, M. F.; Chen, B.; Shen, F.; Filippopoulos, T.; Su, Y. L.; Goldblum, D.; Podos, S. M.; Mittag, T. Quantitative analysis of retinal ganglion cell (RGC) loss in aging DBA/2NNia glaucomatous mice: comparison with RGC loss in aging C57/BL6 mice Invest. Ophthalmol. Vis. Sci. 2003, 44, 5151-5162
39. Kim, K. A.; Shim, S. H.; Ahn, H. R.; Jung, S. H. Protective effects of the compounds isolated from the seed of Psoralea corylifolia on oxidative stress-induced retinal damage Toxicol. Appl. Pharmacol. 2013, 269, 109-120
40. Kuehn, M. H.; Fingert, J. H.; Kwon, Y. H. Retinal ganglion cell death in glaucoma: mechanisms and neuroprotective strategies Ophthalmol. Clin. North Am. 2005, 18 (vi) 383-395
41. Galaris, D.; Pantopoulos, K. Oxidative stress and iron homeostasis: mechanistic and health aspects Crit. Rev. Clin. Lab. Sci. 2008, 45, 1-23
42. Andersen, J. K. Oxidative stress in neurodegeneration: cause or consequence? Nat. Med. 2004, 10 (Suppl) S18-25
43. Ko, M. L.; Peng, P. H.; Ma, M. C.; Ritch, R.; Chen, C. F. Dynamic changes in reactive oxygen species and antioxidant levels in retinas in experimental glaucoma Free Radical Biol. Med. 2005, 39, 365-373
44. Izzotti, A.; Bagnis, A.; Sacca, S. C. The role of oxidative stress in glaucoma Mutat. Res. 2006, 612, 105-114
45. Mozaffarieh, M.; Grieshaber, M. C.; Orgul, S.; Flammer, J. The potential value of natural antioxidative treatment in glaucoma Surv. Ophthalmol. 2008, 53, 479-505
46. Kang, K. D.; Majid, A. S.; Kim, K. A.; Kang, K.; Ahn, H. R.; Nho, C. W.; Jung, S. H. Sulbutiamine counteracts trophic factor deprivation induced apoptotic cell death in transformed retinal ganglion cells Neurochem. Res. 2010, 35, 1828-1839
47. Aslan, M.; Cort, A.; Yucel, I. Oxidative and nitrative stress markers in glaucoma Free Radical Biol. Med. 2008, 45, 367-376
48. Babizhayev, M. A.; Bunin, A. Lipid peroxidation in open-angle glaucoma Acta Ophthalmol. 1989, 67, 371-377
49. Lam, T. T.; Abler, A. S.; Kwong, J. M.; Tso, M. O. N -methyl- d -aspartate (NMDA)-induced apoptosis in rat retina Invest. Ophthalmol. Vis. Sci. 1999, 40, 2391-2397
50. Ng, Y. K.; Zeng, X. X.; Ling, E. A. Expression of glutamate receptors and calcium-binding proteins in the retina of streptozotocin-induced diabetic rats Brain Res. 2004, 1018, 66-72
51. Joo, C. K.; Choi, J. S.; Ko, H. W.; Park, K. Y.; Sohn, S.; Chun, M. H.; Oh, Y. J.; Gwag, B. J. Necrosis and apoptosis after retinal ischemia: involvement of NMDA-mediated excitotoxicity and p53 Invest. Ophthalmol. Vis. Sci. 1999, 40, 713-720
52. Brandstatter, J. H.; Hartveit, E.; Sassoe-Pognetto, M.; Wassle, H. Expression of NMDA and high-affinity kainate receptor subunit mRNAs in the adult rat retina Eur. J. Neurosci. 1994, 6, 1100-1112
53. Mizuno, K.; Koide, T.; Yoshimura, M.; Araie, M. Neuroprotective effect and intraocular penetration of nipradilol, a beta-blocker with nitric oxide donative action Invest. Ophthalmol. Vis. Sci. 2001, 42, 688-694
54. Hughes, W. F. Quantitation of ischemic damage in the rat retina Exp. Eye Res. 1991, 53, 573-582
55. Leung, C. K.; Lindsey, J. D.; Crowston, J. G.; Lijia, C.; Chiang, S.; Weinreb, R. N. Longitudinal profile of retinal ganglion cell damage after optic nerve crush with blue-light confocal scanning laser ophthalmoscopy Invest. Ophthalmol. Vis. Sci. 2008, 49, 4898-4902
56. Kreutz, M. R.; Seidenbecher, C. I.; Sabel, B. A. Molecular plasticity of retinal ganglion cells after partial optic nerve injury Restor. Neurol. Neurosci. 1999, 14, 127-134
57. Schuettauf, F.; Rejdak, R.; Thaler, S.; Bolz, S.; Lehaci, C.; Mankowska, A.; Zarnowski, T.; Junemann, A.; Zagorski, Z.; Zrenner, E.; Grieb, P. Citicoline and lithium rescue retinal ganglion cells following partial optic nerve crush in the rat Exp. Eye Res. 2006, 83, 1128-1134
58. Steinsapir, K. D.; Goldberg, R. A. Traumatic optic neuropathy Surv. Ophthalmol. 1994, 38, 487-518
59. Erk, T.; Renouf, M.; Williamson, G.; Melcher, R.; Steiling, H.; Richling, E. Absorption and isomerization of caffeoylquinic acids from different foods using ileostomist volunteers Eur. J. Nutr. 2013, 10.1007/s00394-013-0512-z
60. Park, C. M.; Jin, K. S.; Lee, Y. W.; Song, Y. S. Luteolin and chicoric acid synergistically inhibited inflammatory responses via inactivation of PI3K-Akt pathway and impairment of NF-κB translocation in LPS stimulated RAW 264.7 cells Eur. J. Pharmacol. 2011, 660, 454-459