Naturally occurring regulators of histone acetylation/deacetylation

Current Nutrition and Food Science

Volumn 6, Issue 1, 2010, Pages 78-99

  Folmer, Florence ^a   Orlikova, Barbora ^a   Schnekenburger, Michael ^a   Dicato, Mario ^a   Diederich, Marc ^a  

^a LABORATOIRE DE BIOLOGIE MOLÉCULAIRE ET CELLULAIRE DU CANCER   (Luxembourg)

Author keywords

Acetylome; Cancer; HDAC HAT inhibitors; Histone acetyl transferase; Histone deacetylase; Natural products

Indexed keywords

2 PROPENE 1 THIOL; 6 (METHYLSULFINYLHEXYL) ISOTHIOCYANATE; ALLYL SULFIDE; ALLYLMERCAPTOCYSTEINE; ALPHA TOCOPHEROL; APICIDIN D; BIOTIN; BIS(4 HYDROXYBENZYL)SULFIDE; BUTYRIC ACID; CHLAMYDOCIN; CYCLO[LEUCYLPIPECOLYL (2 AMINO 8 OXO 9,10 EPOXYDECANOYL) DEXTRO PHENYLALANYL]; ERUCIN; FR 225497; FR 235222; FR 90137; HISTONE ACETYLTRANSFERASE; HISTONE DEACETYLASE; HISTONE DEACETYLASE INHIBITOR; HYDROXAMIC ACID; LINOLEIC ACID; PACLITAXEL; PHENETHYL ISOTHIOCYANATE; PSAMMAPLIN A; ROMIDEPSIN; STAVZOR; SULFORAPHANE; SULFORAPHANE CYSTEINE; THIOCTIC ACID; TRAPOXIN A; TRAPOXIN B; TRICHOSTATIN A; UNCLASSIFIED DRUG; UNINDEXED DRUG; VALPROATE SEMISODIUM; VALPROIC ACID; VORINOSTAT;

ACETYLATION; CHROMATIN; CLINICAL TRIAL; CONFORMATION; DEACETYLATION; DRUG INHIBITION; DRUG ISOLATION; DRUG POTENTIATION; DRUG STRUCTURE; ENDOMETRIUM CANCER; GENE EXPRESSION; HUMAN; INFECTION; INFLAMMATION; OVARY CANCER; PRIORITY JOURNAL; REVIEW; SKIN LYMPHOMA; STRUCTURE ACTIVITY RELATION;

EID: 77949705465     PISSN: 15734013     EISSN: None     Source Type: Journal    
DOI: 10.2174/157340110790909581     Document Type: Review

References (130)

1. Lodish H, Berk A, Kaiser CA, et al. Molecular cell biology. New York: Freemann WH. 2008; p. 1150.
2. Batty N, Malouf GG, Issa JPJ Histone deacetylase inhibitors as anti-neoplastic agents. Cancer Lett 2009; 280: 192-200.
3. Delage B, Dashwood RH. Dietary manipulation of histone structure and function. Annu Rev Nutr 2008; 28: 347-66.
4. Dashwood RH, Ho E. Dietary histone deacetylase inhibitors: From cells to mice to man. Semin Cancer Biol 2007; 17: 363-9.
5. Acharya MR, Sparreboom A, Venitz J, Figg WD. Rational development of histone deacetylase inhibitors as anticancer agents: a review. Mol Pharmacol 2005; 68: 917-32.
6. Arif M, Pradhan SK, Thanuja GR, et al. Mechanism of p300 specific histone acetyltransferase inhibition by small molecules. J Med Chem 2009; 52: 267-77.
7. Davis CD, Ross SA. Dietary components impact histone modifications and cancer risk. Nutr Rev 2007; 65: 88-94.
8. Inche AG, La Thangue NB. Chromatin control and cancer-drug discovery: realizing the promise. Drug Discov Today 2006; 11: 97-109.
9. Liu T, Liu PY, Marshall GM. The critical role of the class III histone deacetylase SIRT1 in cancer. Cancer Res 2009; 69: 1702-5.
10. Nian H, Delage B, Ho E, Dashwood RH. Modulation of histone deacetylase activity by dietary isothiocyanates and allyl sulfides: Studies with sulforaphane and garlic organosulfur compounds. Environ Mol Mutag 2009; 50: 213-21.
11. Butler MS, Newman DJ. Mother nature' gifts to disease s of man: The impact of natural products on anti-infective, anticholestemics and anticancer drug discovery. In: Petersen F, Amstutz R, Eds. Natural compounds as drugs. New York: Springer 2008; pp. 1-44.
12. Cragg GM, Grothaus PG, Newman DJ. Impact of natural products on developing new anti-cancer agents. Chem Rev 2009; 109: 3012-43.
13. Botrugno OA, Santoro F, Minucci S. Histone deacetylase inhibitors as a new weapon in the arsenal of differentiation therapies of cancer. Cancer Lett 2009; 280: 134-44.
14. Bieliauskas AV, Pflum MKH. Isoform-selective histone deacetylase inhibitors. Chem Soc Rev 2008; 37: 1402-13.
15. Porcu M, Chiarugi A. The emerging therapeutic potential of sirtuin-interacting drugs: from cell death to lifespan extension. Trends Pharmacol Sci 2006; 26: 94-103.
16. Miller TA, Witter DJ, Belvedere S. Histone deacetylase inhibitors. J Med Chem 2003; 46: 5097-116.
17. Grozinger CM, Schreiber SL. Deacetylase enzymes: biological functions and the use of small-molecule inhibitors. Chem Biol 2002; 9: 3-16.
18. Gallinari P, Di Marco S, Jones P, Pallaoro M, Steinkühler C. HDACs, histone deacetylation and gene transcription: from molecular biology to cancer therapeutics. Cell Res 2007; 17: 195-211.
19. Di Gennaro E, Bruzzese F, Caraglia M, Abruzzese A, Budillon A. Acetylation of proteins as novel target for antitumor therapy: review article. Amino Acids 2004; 26: 435-41.
20. Luger K, Mader AW, Richmond RK, Sargent DF, Richmond TJ. Crystal structure of the nucleosome core particle at 2.8 A resolution. Nature 1997; 389: 251-60.
21. Struhl K. Histone acetylation and transcriptional regulatory mechanisms. Genes Dev 1998; 12: 599-606.
22. Widom J. Chromatin structure: linking structure to function with histone H1. Curr Biol 1998; 8: R788-91.
23. Oberdoerffer P, Sinclair DA. The role of nuclear architecture in genomic instability and ageing. Nat Rev Mol Cell Biol 2007; 8: 692-702.
24. Rea S, Eisenhaber F, O'Carroll D, et al. Regulation of chromatin structure by site-specific histone H3 methyltransferases. Nature 2000; 406: 593-9.
25. Zhu P, Zhou W, Wang J, et al. A histone H2A deubiquitinase complex coordinating histone acetylation and H1 dissociation in transcriptional regulation. Mol Cell 2007; 27: 609-21.
26. Dover J, Schneider J, Tawiah-Boateng MA, et al. Methylation of histone H3 by COMPASS requires ubiquitination of histone H2B by Rad6. J Biol Chem 2002; 277: 28368-71.
27. Kwon P, Hsu M, Cohen D, Atadja P. HDAC Inhibitors: An emerging anticancer therapeutic strategy. In: Verdin E, Ed. Histone deacetylases: Transcriptional regulation and other cellular functions. Totowa, NJ: Humana Press 2006; pp. 315-32.
28. Gregoire S, Yang XJ. Association with class IIa histone deacetylases upregulates the sumoylation of MEF2 transcription factors. Mol Cell Biol 2005; 25: 2273-87.
29. Sapetschnig A, Rischitor G, Braun H, et al. Transcription factor Sp3 is silenced through SUMO modification by PIAS1. EMBO J 2002; 21: 5206-15.
30. Geiss-Friedlander R, Melchior F. Concepts in sumoylation: a decade on. Nat Rev Mol Cell Biol 2007; 8: 947-56.
31. Caron C, Boyault C, Khochbin S. Regulatory cross-talk between lysine acetylation and ubiquitination: role in the control of protein stability. Bioassays 2005; 27: 408-15.
32. Eskeland R, Eberharter A, Imhof A. HP1 binding to chromatin methylated at H3K9 is enhanced by auxiliary factors. Mol Cell Biol 2007; 27: 453-65.
33. Verschure PJ, van der Kraan I, de Leeuw W, et al. In vivo HP1 targeting causes large-scale chromatin condensation and enhanced histone lysine methylation. Mol Cell Biol 2005; 25: 4552-64.
34. Davie JR. Covalent modifications of histones: expression from chromatin templates. Curr Opin Genet Dev 1998; 8: 173-8.
35. Grunstein M. Histone acetylation in chromatin structure and transcription. Nature 1997; 389: 349-52.
36. Ropero S, Esteller M. The role of histone deacetylases (HDACs) in human cancer. Mol Oncol 2007; 1: 19-25.
37. Park JH, Cosgrove MS, Youngman E, Wolberger C, Boeke JD. A core nucleosome surface crucial for transcriptional silencing. Nat Genet 2002; 32: 273-9.
38. Spange S, Wagner T, Heinzel T, Kramer OH. Acetylation of non-histone proteins modulates cellular signalling at multiple levels. Int J Biochem Cell Biol 2009; 41: 185-98.
39. Gregoretti IV, Lee YM, Goodson HV. Molecular evolution of the histone deacetylase family: functional implications of phylogenetic analysis. J Mol Biol 2004; 338: 17-31.
40. Pérez-Balado C, Nebbioso A, Rodríguez-Graña P, et al. Bispyridium dienes: Histone deacetylase inhibitors with selective activities. J Med Chem 2007; 50: 2497-505.
41. Howitz KT, Bitterman KJ, Cohen HY, et al. Small molecule activators of sirtuins extend Saccharomyces cerevisiae lifespan. Nature 2003; 425: 191-6.
42. de Ruijter AJ, van Gennip AH, Caron HN, Kemp S, van Kuilenburg ABBJ. Histone deacetylases (HDACs): characterization of the classical HDAC family. Biochem J 2003; 370: 737-49.
43. Verdin E, Dequiedt F, Kasler HG. Class II histone deacetylases: versatile regulators. Trends Genet 2003; 19: 286-93.
44. Xu WS, Parmigiani RB, Marks PA. Histone deacetylase inhibitors: molecular mechanisms of action. Oncogene 2007; 26: 5541-52.
45. Hodawadekar SC, Marmorstein R. Chemistry of acetyl transfer by histone modifying enzymes: structure, mechanism and implications for effector design. Oncogene 2007; 26: 5528-40.
46. Balasubramanyam K, Swaminathan V, Ranganathan A, Kundu TK. Small molecule modulators of histone acetyltransferase p300. J Biol Chem 2003; 278: 19134-40.
47. Tang Y, Zhao W, Chen Y, Zhao Y, Gu W. Acetylation is indispensable for p53 activation. Cell 2008; 133: 612-26.
48. Martin A, Odajima J, Hunt SL, et al. Cdk2 is dispensable for cell cycle inhibition and tumor suppression mediated by p27(Kip1) and p21(Cip1). Cancer Cell 2005; 7: 591-8.
49. Tang Y, Luo J, Zhang W, Gu W. Tip60-dependent acetylation of p53 modulates the decision between cell-cycle arrest and apoptosis. Mol Cell 2006; 24: 827-39.
50. Stimson L, La Thangue NB. Biomarkers for predicting clinical responses to HDAC inhibitors. Cancer Lett 2009; 280: 177-83.
51. van der Horst A, Tertoolen LG, de Vries-Smits LM, et al. FOXO4 is acetylated upon peroxide stress and deacetylated by the longevity protein hSir2(SIRT1). J Biol Chem 2004; 279: 28873-9.
52. Binda O, Nassif C, Branton PE. SIRT1 negatively regulates HDAC1-dependent transcriptional repression by thr RBP1 family of proteins. Oncogene 2008; 27: 3384-92.
53. Krämer OH, Baus D, Knauer SK, et al. Acetylation of Stat1 modulates NF-kappaB activity. Genes Dev 2006; 20: 473-85.
54. Buerki C, Rothgiesser KM, Valovka T, et al. Functional relevance of novel p300-mediated lysine 314 and 315 acetylation of relA/p65. Nucleic Acids Res 2008; 36: 1665-80.
55. Choi KC, Jung MG, Lee YH, et al. Epigallocatechin-3-gallate, a histone acetyltransferase inhibitor, inhibits EBV-induced B lymphocyte transformation via suppression of RelA acetylation. Cancer Res 2009; 69: 583-92.
56. Williams PG. Panning for chemical gold: marine bacteria as a source of new therapeutics. Trends Biotechnol 2008; 27: 45-50.
57. Guan JS, Haggarty SJ, Giacometti E, et al. HDAC2 negatively regulates memory formation and synaptic plasticity. Nature 2009; 459: 55-9.
58. Alcain FJ, Villalba JM. Sirtuin activators. Exp Opin Ther Pat 2009; 19: 403-14.
59. Singh SB, Zink DL, Liesch JM, et al. Structure and chemistry of apicidins, a class of novel cyclic tetrapeptides without a terminal α-keto epoxide as inhibitors of histone deacetylase with potent antiprotozoal activities. J Org Chem 2002; 67: 815-25.
60. Cui L, Miao J, Furuya T, et al. Histone acetyltransferase inhibitor anacardic acid causes changes in global gene expression during in vitro Plasmodium falciparum development. Eukaryot Cell 2008; 7: 1200-10.
61. Schemies J, Sippl W, Jung M. Histone deacetylase inhibitors that target tubulin. Cancer Lett 2009; 280: 222-32.
62. Rotili D, Simonetti G, Savarino A, et al. Non-cancer uses of histone deacetylase inhibitors: Effects on infectious diseases and betahemoglobinopathies. Curr Top Med Chem 2009; 9: 272-91.
63. Rider SD, Zhu G. An apicomplexan ankyrin-repeat histone deacetylase with relatives in photosynthetic eukaryotes. Int J Parasitol 2009; 39: 747-54.
64. Rahman MM, Kukita A, Kukita T, et al. Two histone deacetylase inhibitors, trichostatin A and sodium butyrate, suppress differentiation into osteoclasts but not into macrophages. Blood 2003; 101: 3451-9.
65. ten Holte P, Van Emelen K, Janicot M, et al. HDAC inhibition in cancer therapy: an increasingly intriguing tale of chemistry, biology and clinical benefit. Cancer. Berlin: Springer 2007; pp. 293-331.
66. Fraga MF, Esteller M. Towards the human cancer epigenome: a first draft of histone modifications. Cell Cycle 2005; 4: 1377-81.
67. Manzo F, Tambaro FP, Mai A, Altucci L. Histone acetyltransferase inhibitors and preclinical studies. Exp Opin Ther Pat 2009; 19: 761-74.
68. Racanicchi S, Maccherani C, Liberatore C, et al. Targeting fusion protein/corepressor contact restores differentiation response in leukemia cells. EMBO J 2005; 24: 1232-42.
69. Wang J, Hoshino T, Redner RL, Kajigaya S, Liu JM. ETO, fusion partner in t(8;21) acute myeloid leukemia, represses transcription by interaction with the human N-CoR/mSin3/HDAC1 complex. Proc Natl Acad Sci USA 1998; 95: 10860-5.
70. Zhu P, Martin E, Mengwasser J, et al. Induction of HDAC2 expression upon loss of APC in colorectal tumorigenesis. Cancer Cell 2004; 5: 455-63.
71. Jin KL, Pak JH, Park JY, et al. Expression profile of histone deacetylases 1, 2 and 3 in ovarian cancer tissues. J Gynecol Oncol 2008; 19: 185-90.
72. Ouaïssi M, Sielezneff I, Silvestre R, et al. High histone deacetylase 7 (HDAC7) expression is significantly associated with adenocarcinomas of the pancreas. An Surg Cancer 2008; 15: 2318-28.
73. Choi JH, Kwon HJ, Yoon BI, et al. Expression profile of histone deacetylase 1 in gastric cancer tissues. Jpn J Cancer Res 2001; 92: 1300-4.
74. Zhang Z, Yamashita H, Toyama T, et al. Quantitation of HDAC1 mRNA expression in invasive carcinoma of the breast. Breast Cancer Res Treat 2005; 94: 11-6.
75. Tai KY, Shiah SG, Shieh YS, et al. DNA methylation and histone modification regulate silencing of epithelial cell adhesion molecule for tumor invasion and progression. Oncogene 2007; 26: 3989-97.
76. Myzak MC, Ho E, Dashwood RH. Dietary agents as histone deacetylase inhibitors. Mol Carcinog 2006; 45: 443-6.
77. Kumagai T, Wakimoto N, Yin D, et al. Histone deacetylase inhibitor, suberoylanilide hydroxamic acid (Vorinostat, SAHA) profoundly inhibits the growth of human pancreatic cancer cells. Int J Cancer 2007; 121: 656-65.
78. Wang J, Saunthararajah Y, Redner RL, Liu JM. Inhibitors of histone deacetylase relieve ETO-mediated repression and induce differentiation of AML1-ETO leukemia cells. Cancer Res 1999; 59: 2766-9.
79. Prince HM, Bishton MJ, Harrison SJ. Clinical studies of histone deacetylase inhibitors. Clin Cancer Res 2009; 15: 3958-69.
80. Delage B, Dashwood RH. Nutrients, histone modifications, and chromatin remodeling in chronic inflammation. In: Choi SW, Friso S, Eds. Nutrients and epigenetics. Boca Raton, FL: CRC Press 2009; pp. 135-40.
81. Dashwood RH, Myzak MC, Ho E. Dietary HDAC inhibitors: time to rethink weak ligands in cancer prevention? Carcinogenesis 2006; 27: 344-9.
82. Gibbons RJ. Histone modifying and chromatin remodelling enzymes in cancer and dysplastic syndromes. Hum Mol Genet 2005; 14 Spec no. 1: R85-92.
83. Witt O. HDAC inhibitors; magic bullets, dirty drugs or just another targeted therapy. Cancer Lett 2009; 280: 123-4.
84. Taori K, Liu Y, Paul VJ, Luesch H. Combinatorial strategies by marine cyanobacteria : Symplostatin 4, an antimitotic natural dolastatin 10/15 hybrid that synergizes with the coproduced HDAC inhibitor largazole. ChemBioChem 2009; 10: 1634-9.
85. Crabb SJ, Howell M, Rogers H, et al. Characterisation of the in vitro activity of the depsipeptide histone deacetylase inhibitor spiruchostatin A. Biochem Pharmacol 2008; 76: 463-75.
86. Khan N, Jeffers M, Kumar S, et al. Determination of the class and isoform selectivity of small-molecule histone deacetylase inhibitors. Biochem J 2008; 409: 581-9.
87. Myzak MC, Hardin K, Wang R, Dashwood RH, Ho E. Sulforaphane inhibits histone deacetylase activity in BPH-1, LnCaP and PC-3 prostate epithelial cells. Carcinogenesis 2006; 27: 811-9.
88. Plate AY, Gallaher DD. Effects of indole-3-carbinol and phenethyl isothiocyanate on colon carcinogenesis induced by azoxymethane in rats. Carcinogenesis 2006; 27: 287-92.
89. Son IH, Lee SI, Yang HD, Moon HI. Bis(4-hydroxybenzyl)sufide: a sulfur compound inhibitor of histone deacetylase isolated from root extract of Pleuropterus ciliinervis. Molecules 2007; 12: 815-20.
90. Nakao Y, Yoshida S, Matsunaga S, et al. Azumamides A-E: Histone deacetylase inhibitory cyclic tetrapeptides from the marine sponge Mycale izuensis. Angew Chem Int Ed 2006; 45: 7553-7.
91. Rodriquez M, Bruno I, Cini E, et al. Synthesis of 2-amino-8-oxodecanoic acids (Aodas) present in natural histone deacetylase inhibitors. J Org Chem 2006; 71: 103-7.
92. Montero A, Beierle JM, Olsen CA, Ghadiri MR. Design, synthesis, biological evaluation, and structural characterization of potent histone deacetylase inhibitors based on cyclic α/β. J Am Chem Soc 2009; 131: 3033-41.
93. Maulucci N, Chini MG, Di Micco S, et al. Molecular insights into azumamide E histone deacetylase inhibitory activity. J Am Chem Soc 2007; 129: 3007-12.
94. Nishino N, Yoshikawa D, Watanabe LA, et al. Synthesis and histone deacetylase inhibitory activity of cyclic tetrapeptides containing a retrohydroxamate as zinc ligand. Bioorg Med Chem Lett 2004; 14: 2427-31.
95. Di Micco S, Terracciano S, Bruno I, et al. Molecular modeling studies toward the structural optimization of new cyclopeptide-based HDAC inhibitors modeled on the natural product FR235222. Bioorg Med Chem Lett 2008; 16: 8635-42.
96. Gu W, Cueto M, Jensen PR, Fenical W, Silverman RB. Microsporins A and B: new histone deacetylase inhibitors from the marine-derived fungus Microsporum cf. gypseum and the solid-phase synthesis of microsporin A. Tetrahedron 2007; 63: 6535-41.
97. Furumai R, Komatsu Y, Nishino N, et al. Potent histone deacetylase inhibitors built from trichostatin A and cyclic tetrapeptide antibiotics including trapoxin. Proc Natl Acad Sci USA 2001; 98: 87-92.
98. Cheng YQ, Yang M, Matter AM. Characterization of a gene cluster responsible for the biosynthesis of anticancer agent FK228 in Chromobacterium violaceum No. 968. Appl Environ Microbiol 2007; 73: 3460-9.
99. Furumai R, Matsuyama A, Kobashi N, et al. FK228 (depsipeptide) as a natural prodrug that inhibits class I histone deacetylases. Cancer Res 2002; 62: 4916-21.
100. Konstantinopoulos PA, Vandoros GP, Papavassiliou AG. FK228 (depsipeptide): a HDAC inhibitor with pleiotropic antitumor activities. Cancer Chemother Pharmacol 2006; 58: 711-5.
101. Fennell KA, Millmann U, Miller MJ. Syntheses and biological activity of amimastatin B and analogues. J Org Chem 2008; 73: 1018-24.
102. Olaharski AJ, Rine J, Marshall BL, et al. The flavoring agent dihydrocoumarin reverses epigenetic silencing and inhibits sirtuin deacetylases. PLoS Genet 2005; 1: 689-94.
103. Pia IC, Gautschi JT, Wang GYS, et al. Psammaplins from the sponge Pseudoceratina purpurea: Inhibition of both histone deacetylase and DNA methyltransferase. J Org Chem 2003; 68: 3866-73.
104. Kim DH, Shin J, Kwon HJ. Psammaplin A is a natural prodrug that inhibits class I histone deacetylase. Exp Mol Med 2007; 39: 47-55.
105. McCulloch MWB, Coombs GS, Banerjee N, et al. Psammaplin A as a general activator of cell-based signaling assays via HDAC inhibition and studies on some bromotyrosine derivatives. Bioorg Med Chem Lett 2009; 17: 2189-98.
106. Catley L, Weisberg E, Tai YT, et al. NVP-LAQ824 is a potent novel histone deacetylase inhibitor with significant activity against multiple myeloma. Blood 2003; 102: 2615-22.
107. Bontempo P, Mita L, Miceli M et al. Feijoa sellowiana derived natural flavone exerts anti-cancer action displaying HDAC inhibitory activities. Int J Biochem Cell Biol 2007; 39: 1902-14.
108. Son IH, Chung, IM, Lee SI, Yang HD, Moon HI. Pomiferin, histone deacetylase inhibitor isolated from the fruits of Maclura pomifera. Bioorg Med Chem Lett 2007; 17: 4753-5.
109. Chung IM, Kim MY, Park WH, Moon HI. Histone deacetylase inhibitors from the rhizomes of Zingiber zerumbet. Pharmazie 2008; 63: 774-6.
110. Xiong SD, Yu K, Liu XH, et al. Ribosome-inactivating proteins isolated from dietary bitter melon induce apoptosis and inhibit histone deacetylase-1 selectively in premalignant and malignant prostate cancer cells. Int J Cancer 2009; 125: 774-82.
111. Oku N, Nagai K, Shindoh N, et al. Three new cyclostellettamines, which inhibit histone deacetylase, from a marine sponge of the genus Xestospongia. Bioorg Med Chem Lett 2004; 14: 2617-20.
112. Mukwevho E, Kohn TA, Lang D, et al. Caffeine induces hyperacetylation of histones at the MEF2 site on the Glut4 promoter and increases MEF2A binding to the site via a CaMK-dependent mechanism. Am J Physiol Endocrinol Metab 2008; 294: 582-8.
113. Zhou B, Wu LJ, Li LH, et al. Silibinin protects against isoproterenol-induced rat cardiac myocyte injury through mitochondrial pathway after up-regulation of SIRT1. J Pharmacol Sci 2006; 102: 387-95.
114. Rasbach KA, Schnellmann RG. Isoflavones promote mitochondrial biogenesis. J Pharmacol Exp Ther 2008; 325: 536-43.
115. Cosio BG, Tsaprouni L, Ito K, et al. Theophylline restores histone deacetylase activity and steroid responses in COPD macrophages. J Exp Med 2004; 200: 689-95.
116. Ito K, Lim S, Caramori G, et al. A molecular mechanism of action of theophylline: Induction of histone deacetylase activity to decrease inflammatory gene expression. Proc Natl Acad Sci USA 2002; 99: 8921-6.
117. Barnes PJ, Adcock IM, Ito K. Histone acetylation and deacetylation: importance in inflammatory lung diseases. Eur Respir J 2005; 25: 552-63.
118. Balasubramanyam K, Altaf M, Varier RA, et al. Polyisoprenylated benzophenone, garcinol, a natural histone acetyltransferase inhibitor, represses chromatin transcription and alters global gene expression. J Biol Chem 2004; 279: 33716-25.
119. Lu MC, Du YC, Hwang SL, et al. Active extracts of wild fruiting bodies of Antrodia camphorata (EEAC) induce leukemia HL 60 cells apoptosis partially through histone hypoacetylation and synergistically promote anticancer effect of trichostatin A. Arch Toxicol 2009; 83: 121-9.
120. Kang J, Chen J, Shi Y, Jia J, Zhang Y. Curcumin-induced histone hypoacetylation: The role of reactive oxygen species. Biochem Pharmacol 2005; 69: 1205-13.
121. O'Connor OA, Foss F. HDAC inhibitors: Mechanisms of action and efficacy in the treatment of hematologic malignancy. Hematol Oncol 2006; 4: 1-8.
122. Bravo SB, Garcia-Rendueles MER, Seoane R, et al. Plitidepsin has a cytostatic effect in human undifferentiated (anaplastic) thyroid carcinoma. Clin Cancer Res 2005; 11: 7664-73.
123. Lee YH, Hong SW, Jun W, et al. Anti-histone acetyltransferase activity from allspice extracts Inhibits androgen receptor-dependent prostate cancer cell growth. Biosci Biotechnol Biochem 2007; 71: 2712-9.
124. Nakatani N. Phenolic antioxidants from herbs and spices. BioFactors 2000; 13: 141-6.
125. Lin C, Kang J, Zheng R. Oxidative stress is involved in inhibition of copper on histone acetylation in cells. Chem Biol Interact 2005; 151: 167-76.
126. Xiao JJ, Foraker AB, Swaan PW, et al. Efflux of depsipeptide FK228 (FR901228, NSC-630176) is mediated by P-glycoprotein and multidrug resistance-associated protein 1. J Pharmacol Exp Ther 2005; 313: 268-76.
127. Castro-Galachea MD, Menéndez-Gutiérrezb MP, Garciaa EC, et al. Protein kinase C-alpha antagonizes apoptosis induction by histone deacetylase inhibitors in multidrug resistant leukaemia cells. Int J Biochem Cell Biol 2007; 39: 1877-85.
128. Ruefli AA, Bernhard D, Tainton KM, et al. Suberoylanilide hydroxamic acid (SAHA) overcomes multidrug resistance and induces cell death in P-glycoprotein-expressing cells. Int J Cancer 2002; 99: 292-8.
129. Pulukuri SM, Gorantla B, Rao JS. Inhibition of histone deacetylase activity promotes invasion of human cancer cells through activation of urokinase plasminogen activator. J Biol Chem 2007; 282: 35594-603.
130. Yang Y, Rao R, Shen J, et al. Role of acetylation and extracellular location of heat shock protein 90alpha in tumor cell invasion. Cancer Res 2008; 68: 4833-42.