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Planta Med 2016; 82(17): 1456-1462
DOI: 10.1055/s-0042-109173
Biological and Pharmacological Activity
Original Papers
Georg Thieme Verlag KG Stuttgart · New York

Protective Effects of a Diarylheptanoid from Curcuma comosa Against Hydrogen Peroxide-Induced Astroglial Cell Death

Jaturavit Vattanarongkup
1   Department of Pharmacology, Faculty of Science, Mahidol University, Bangkok, Thailand
,
Pawinee Piyachaturawat
2   Department of Physiology, Faculty of Science, Mahidol University, Bangkok, Thailand
,
Patoomratana Tuchinda
3   Department of Chemistry, Faculty of Science, Mahidol University, Bangkok, Thailand
,
Pimtip Sanvarinda
1   Department of Pharmacology, Faculty of Science, Mahidol University, Bangkok, Thailand
,
Yupin Sanvarinda
1   Department of Pharmacology, Faculty of Science, Mahidol University, Bangkok, Thailand
,
Nattinee Jantaratnotai
1   Department of Pharmacology, Faculty of Science, Mahidol University, Bangkok, Thailand
› Author Affiliations
Further Information

Publication History

received 06 January 2016
revised 16 May 2016

accepted 18 May 2016

Publication Date:
24 June 2016 (online)

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Abstract

Oxidative stress is one of the major mechanisms causing neuronal and astroglial cell death in various neurological disorders such as Alzheimerʼs disease, Parkinsonʼs disease, and brain ischemia. Two diarylheptanoids, (3R)-1,7-diphenyl-(4E,6E)-4,6-heptadien-3-ol (ASPP 049) and (3S)-7-(3,4-dihydroxyphenyl)-1-phenyl-(1E)-1-hepten-3-ol (ASPP 092), isolated from Curcuma comosa were investigated for cytoprotective effects on C6 astroglial cells using hydrogen peroxide (H2O2) exposure as a model of oxidative stress. ASPP 092 demonstrated free radical scavenging activity comparable to that of vitamin C, while ASPP 049 showed no antioxidant activity. Treatment with H2O2 at 400 µM for 12 h caused 79 % C6 astroglial cell death which was significantly reduced to 37 % by pretreatment with ASPP 092 (5 µM). In addition, ASPP 092 attenuated the increase in reactive oxygen species production and the decrease in total glutathione level induced by H2O2. The mechanism of ASPP 092 protection against H2O2-induced apoptotic signaling appeared to involve prevention of increase in the level of phosphorylated p53 and the Bax/Bcl-2 ratio as well as cleaved caspase-3. These findings provide new evidence that the diarylheptanoid ASPP 092 from C. comosa possesses antiapoptotic properties and could be further developed as a potential treatment for oxidative stress-related neuronal diseases.

Key words

Curcuma comosa - Zingiberaceae - apoptosis - C6 astroglia - diarylheptanoid - hydrogen peroxide - oxidative stress
 

  • References

  • 1 Andersen JK. Oxidative stress in neurodegeneration: cause or consequence?. Nat Med 2004; 10: S18-S25
    CrossrefPubMedGoogle Scholar
  • 2 Smaga I, Niedzielska E, Gawlik M, Moniczewski A, Krzek J, Przegalinski E, Pera J, Filip M. Oxidative stress as an etiological factor and a potential treatment target of psychiatric disorders. Part 2. Depression, anxiety, schizophrenia and autism. Pharmacol Rep 2015; 67: 569-580
    CrossrefPubMedGoogle Scholar
  • 3 Trushina E, McMurray CT. Oxidative stress and mitochondrial dysfunction in neurodegenerative diseases. Neuroscience 2007; 145: 1233-1248
    CrossrefPubMedGoogle Scholar
  • 4 Jaisin Y, Thampithak A, Meesarapee B, Ratanachamnong P, Suksamrarn A, Phivthong-Ngam L, Phumala-Morales N, Chongthammakun S, Govitrapong P, Sanvarinda Y. Curcumin I protects the dopaminergic cell line SH-SY5Y from 6-hydroxydopamine-induced neurotoxicity through attenuation of p 53-mediated apoptosis. Neurosci Lett 2011; 489: 192-196
    CrossrefPubMedGoogle Scholar
  • 5 Koh K, Cha Y, Kim S, Kim J. tBHQ inhibits LPS-induced microglial activation via Nrf2-mediated suppression of p 38 phosphorylation. Biochem Biophys Res Commun 2009; 380: 449-453
    CrossrefPubMedGoogle Scholar
  • 6 Martin-Moreno AM, Reigada D, Ramirez BG, Mechoulam R, Innamorato N, Cuadrado A, de Ceballos ML. Cannabidiol and other cannabinoids reduce microglial activation in vitro and in vivo: relevance to Alzheimerʼs disease. Mol Pharmacol 2011; 79: 964-973
    CrossrefPubMedGoogle Scholar
  • 7 Allaman I, Belanger M, Magistretti PJ. Astrocyte-neuron metabolic relationships: for better and for worse. Trends Neurosci 2011; 34: 76-87
    CrossrefPubMedGoogle Scholar
  • 8 Maragakis NJ, Rothstein JD. Mechanisms of disease: astrocytes in neurodegenerative disease. Nat Clin Pract Neurol 2006; 2: 679-689
    PubMedGoogle Scholar
  • 9 Rossi D, Volterra A. Astrocytic dysfunction: insights on the role in neurodegeneration. Brain Res Bull 2009; 80: 224-232
    CrossrefPubMedGoogle Scholar
  • 10 Abbott NJ, Ronnback L, Hansson E. Astrocyte-endothelial interactions at the blood-brain barrier. Nat Rev Neurosci 2006; 7: 41-53
    CrossrefPubMedGoogle Scholar
  • 11 Desagher S, Glowinski J, Premont J. Astrocytes protect neurons from hydrogen peroxide toxicity. J Neurosci 1996; 16: 2553-2562
    CrossrefPubMedGoogle Scholar
  • 12 Rocha SM, Cristovão AC, Campos FL, Fonseca CP, Baltazar G. Astrocyte-derived GDNF is a potent inhibitor of microglial activation. Neurobiol Dis 2012; 47: 407-415
    CrossrefPubMedGoogle Scholar
  • 13 Su J, Sripanidkulchai K, Hu Y, Sripanidkulchai B. Curcuma comosa prevents the neuron loss and affects the antioxidative enzymes in hippocampus of ethanol-treated rats. Pak J Biol Sci 2012; 15: 367-373
    CrossrefPubMedGoogle Scholar
  • 14 Prasannarong M, Saengsirisuwan V, Piyachaturawat P, Suksamrarn A. Improvements of insulin resistance in ovariectomized rats by a novel phytoestrogen from Curcuma comosa Roxb. BMC Complement Altern Med 2012; 12: 28
    CrossrefPubMedGoogle Scholar
  • 15 Intapad S, Suksamrarn A, Piyachaturawat P. Enhancement of vascular relaxation in rat aorta by phytoestrogens from Curcuma comosa Roxb. Vascul Pharmacol 2009; 51: 284-290
    CrossrefPubMedGoogle Scholar
  • 16 Thampithak A, Jaisin Y, Meesarapee B, Chongthammakun S, Piyachaturawat P, Govitrapong P, Supavilai P, Sanvarinda Y. Transcriptional regulation of iNOS and COX-2 by a novel compound from Curcuma comosa in lipopolysaccharide-induced microglial activation. Neurosci Lett 2009; 462: 171-175
    CrossrefPubMedGoogle Scholar
  • 17 Jitsanong T, Khanobdee K, Piyachaturawat P, Wongprasert K. Diarylheptanoid 7-(3,4dihydroxyphenyl)-5-hydroxy-1-phenyl-(1E)-1-heptene from Curcuma comosa Roxb. protects retinal pigment epithelial cells against oxidative stress-induced cell death. Toxicol In Vitro 2011; 25: 167-176
    CrossrefPubMedGoogle Scholar
  • 18 Shang F, Lu M, Dudek E, Reddan J, Taylor A. Vitamin C and vitamin E restore the resistance of GSH-depleted lens cells to H2O2 . Free Radic Biol Med 2003; 34: 521-530
    CrossrefPubMedGoogle Scholar
  • 19 Priyadarsini KI, Maity DK, Naik GH, Kumar MS, Unnikrishnan MK, Satav JG, Mohan H. Role of phenolic O-H and methylene hydrogen on the free radical reactions and antioxidant activity of curcumin. Free Radic Biol Med 2003; 35: 475-484
    CrossrefPubMedGoogle Scholar
  • 20 Jariyawat S, Thammapratip T, Suksen K, Wanitchakool P, Nateewattana J, Chairoungdua A, Suksamrarn A, Piyachaturawat P. Induction of apoptosis in murine leukemia by diarylheptanoids from Curcuma comosa Roxb. Cell Biol Toxicol 2011; 27: 413-423
    CrossrefPubMedGoogle Scholar
  • 21 Tantikanlayaporn D, Robinson LJ, Suksamrarn A, Piyachaturawat P, Blair HC. A diarylheptanoid phytoestrogen from Curcuma comosa, 1,7-diphenyl-4,6-heptadien-3-ol, accelerates human osteoblast proliferation and differentiation. Phytomedicine 2013; 20: 676-682
    CrossrefPubMedGoogle Scholar
  • 22 Dringen R, Gutterer JM, Hirrlinger J. Glutathione metabolism in brain metabolic interaction between astrocytes and neurons in the defense against reactive oxygen species. Eur J Biochem 2000; 267: 4912-4916
    CrossrefPubMedGoogle Scholar
  • 23 Fernandez-Fernandez S, Almeida A, Bolaños JP. Antioxidant and bioenergetic coupling between neurons and astrocytes. Biochem J 2012; 443: 3-11
    CrossrefPubMedGoogle Scholar
  • 24 Culmsee C, Mattson MP. p 53 in neuronal apoptosis. Biochem Biophys Res Commun 2005; 331: 761-777
    CrossrefPubMedGoogle Scholar
  • 25 Datta K, Babbar P, Srivastava T, Sinha S, Chattopadhyay P. p 53 dependent apoptosis in glioma cell lines in response to hydrogen peroxide induced oxidative stress. Int J Biochem Cell Biol 2002; 34: 148-157
    CrossrefPubMedGoogle Scholar
  • 26 Yang B, Johnson TS, Thomas GL, Watson PF, Wagner B, Furness PN, El Nahas AM. A shift in the Bax/Bcl-2 balance may activate caspase-3 and modulate apoptosis in experimental glomerulonephritis. Kidney Int 2002; 62: 1301-1313
    CrossrefPubMedGoogle Scholar
  • 27 Kitamura Y, Ota T, Matsuoka Y, Tooyama I, Kimura H, Shimohama S, Nomura Y, Gebicke-Haerter PJ, Taniguchi T. Hydrogen peroxide-induced apoptosis mediated by p 53 protein in glial cells. Glia 1999; 25: 154-164
    CrossrefPubMedGoogle Scholar
  • 28 Tochigi M, Inoue T, Suzuki-Karasaki M, Ochiai T, Ra C, Suzuki-Karasaki Y. Hydrogen peroxide induces cell death in human TRAIL-resistant melanoma through intracellular superoxide generation. Int J Oncol 2013; 42: 863-872
    CrossrefPubMedGoogle Scholar
  • 29 Suksamrarn A, Ponglikitmongkol M, Wongkrajang K, Chindaduang A, Kittidanairak S, Jankam A, Yingyongnarongkul BE, Kittipanumat N, Chokchaisiri R, Khetkam P, Piyachaturawat P. Diarylheptanoids, new phytoestrogens from the rhizomes of Curcuma comosa: Isolation, chemical modification and estrogenic activity evaluation. Bioorg Med Chem 2008; 16: 6891-6902
    CrossrefPubMedGoogle Scholar
  • 30 Jantaratnotai N, Utaisincharoen P, Piyachaturawat P, Chongthammakun S, Sanvarinda Y. Inhibitory effect of Curcuma comosa on NO production and cytokine expression in LPS-activated microglia. Life Sci 2006; 78: 571-577
    CrossrefPubMedGoogle Scholar
  • 31 Trayner ID, Rayner AP, Freeman GE, Farzaneh F. Quantitative multiwell myeloid differentiation assay using dichlorodihydrofluorescein diacetate (H2DCF-DA) or dihydrorhodamine 123 (H2R123). J Immunol Methods 1995; 186: 275-284
    CrossrefPubMedGoogle Scholar
  • 32 Rahman I, Kode A, Biswas SK. Assay for quantitative determination of glutathione and glutathione disulfide levels using enzymatic recycling method. Nat Protoc 2006; 1: 3159-3165
    CrossrefPubMedGoogle Scholar
  • 33 Lowry OH, Rosebrough NJ, Farr AL, Randall RJ. Protein measurement with the Folin phenol reagent. J Biol Chem 1951; 193: 265-275
    PubMedGoogle Scholar