Neuroprotective effects of chrysin: From chemistry to medicine

Neurochemistry International

Volumn 90, Issue , 2015, Pages 224-231

  Nabavi, Seyed Fazel ^a   Braidy, Nady ^b   Habtemariam, Solomon ^c   Orhan, Ilkay Erdogan ^d   Daglia, Maria ^e   Manayi, Azadeh ^f   Gortzi, Olga ^g   Nabavi, Seyed Mohammad ^a  

^a BAQIYATALLAH UNIVERSITY OF MEDICAL SCIENCES   (Iran)

^b UNIVERSITY OF NEW SOUTH WALES   (Australia)

^c UNIVERSITY OF GREENWICH   (United Kingdom)

^d GAZI UNIVERSITY   (Turkey)

^e UNIVERSITY OF PAVIA   (Italy)

^f TEHRAN UNIVERSITY OF MEDICAL SCIENCES   (Iran)

^g Technological Educational Institution of Thessaly Terma N   (Greece)

Author keywords

Antioxidant; Chrysin; Depression; Epilepsy; Neurodegeneration; Neuroprotective

Indexed keywords

CHRYSIN; ANTIOXIDANT; FLAVONOID; NEUROPROTECTIVE AGENT; TUMOR NECROSIS FACTOR;

ANTIAMYLOIDOGENIC EFFECT; ANTIATHEROGENIC EFFECT; ANTICONVULSANT ACTIVITY; ANTIDEPRESSANT ACTIVITY; ANTIINFLAMMATORY ACTIVITY; ANTIOXIDANT ACTIVITY; CHEMISTRY; DRUG ACTIVITY; DRUG BIOAVAILABILITY; HUMAN; NERVOUS SYSTEM INFLAMMATION; NEUROPROTECTION; NEUROTROPHIC EFFECT; NONHUMAN; PARKINSON DISEASE; PRIORITY JOURNAL; REVIEW; SPINAL CORD INJURY; STRUCTURE ACTIVITY RELATION; ANIMAL; MENTAL DISORDERS; METABOLISM; NEURODEGENERATIVE DISEASES;

ANIMALS; ANTIOXIDANTS; FLAVONOIDS; HUMANS; MENTAL DISORDERS; NEURODEGENERATIVE DISEASES; NEUROPROTECTIVE AGENTS; TUMOR NECROSIS FACTOR-ALPHA;

EID: 84946559335     PISSN: 01970186     EISSN: 18729754     Source Type: Journal    
DOI: 10.1016/j.neuint.2015.09.006     Document Type: Review

References (84)

1. T. Akaishi, T. Morimoto, M. Shibao, S. Watanabe, K. Sakai-Kato, N. Utsunomiya-Tate, and K. Abe Structural requirements for the flavonoid fisetin in inhibiting fibril formation of amyloid beta protein Neurosci. Lett. 444 2008 280 285
2. R. Anandhi, T. Annadurai, T.S. Anitha, A.R. Muralidharan, K. Najmunnisha, V. Nachiappan, P.A. Thomas, and P. Geraldine Antihypercholesterolemic and antioxidative effects of an extract of the oyster mushroom, Pleurotus ostreatus, and its major constituent, chrysin, in triton WR-1339-induced hypercholesterolemic rats J. Physiol. Biochem. 69 2013 313 323
3. R. Anandhi, P.A. Thomas, and P. Geraldine Evaluation of the anti-atherogenic potential of chrysin in wistar rats Mol. Cell. Biochem. 385 2014 103 113
4. Y. Bae, S. Lee, and S.H. Kim Chrysin suppresses mast cell-mediated allergic inflammation: involvement of calcium, caspase-1 and nuclear factor-κB Toxicol. Appl. Pharmacol. 254 2011 56 64
5. J. Bai, Y. Luo, Z. Song, W. Fan, Z. Wang, T. Luan, J. Jiang, and B. Zang Effects and the mechanisms of chrysin on sepsis-associated acute lung injury of rats chrysin inhibits acute lung injury Life Sci. J. 10 2013 1052 1058
6. S.P. Bajgai, V. Prachyawarakorn, C. Mahidol, S. Ruchirawat, and P. Kittakoop Hybrid flavan-chalcones, aromatase and lipoxygenase inhibitors, from Desmos cochinchinensis Phytochemistry 72 2011 2062 2067
7. K. Balakrishnan, A. Rijal Upadhaya, J. Steinmetz, J. Reichwald, D. Abramowski, M. Fandrich, S. Kumar, H. Yamaguchi, J. Walter, M. Staufenbiel, and D.R. Thal Impact of amyloid beta aggregate maturation on antibody treatment in APP23 mice Acta Neuropathol. Commun. 3 2015 41
8. J. Bertoncelj, T. Polak, U. Kropf, M. Korošec, and T. Golob LC-DAD-ESI/MS analysis of flavonoids and abscisic acid with chemometric approach for the classification of Slovenian honey Food Chem. 127 2011 296 302
9. D.W. Boulton, U.K. Walle, and T. Walle Extensive binding of the bioflavonoid quercetin to human plasma proteins J. Pharm. Pharmacol. 50 1998 243 249
10. S. Chakraborty, S. Basu, A. Lahiri, and S. Basak Inclusion of chrysin in β-cyclodextrin nanocavity and its effect on antioxidant potential of chrysin: a spectroscopic and molecular modeling approach J. Mol. Struct. 977 2010 180 188
11. H. Che, H. Lim, H.P. Kim, and H. Park A chrysin analog exhibited strong inhibitory activities against both PGE 2 and NO production Eur. J. Med. Chem. 46 2011 4657 4660
12. F. Chen, H.L. Li, Y.F. Tan, Y.H. Li, W.Y. Lai, W.W. Guan, J.Q. Zhang, Y.S. Zhao, and Z.M. Qin Identification of known chemicals and their metabolites from Alpinia oxyphylla fruit extract in rat plasma using liquid chromatography/tandem mass spectrometry (LC-MS/MS) with selected reaction monitoring J. Pharm. Biomed. Anal. 97 2014 166 177
13. T.T. Dao, Y.S. Chi, J. Kim, H.P. Kim, S. Kim, and H. Park Synthesis and inhibitory activity against COX-2 catalyzed prostaglandin production of chrysin derivatives Bioorg. Med. Chem. Lett. 14 2004 1165 1167
14. K. Deckers, M.P. van Boxtel, O.J. Schiepers, M. de Vugt, J.L. Munoz Sanchez, K.J. Anstey, C. Brayne, J.F. Dartigues, K. Engedal, M. Kivipelto, K. Ritchie, J.M. Starr, K. Yaffe, K. Irving, F.R. Verhey, and S. Kohler Target risk factors for dementia prevention: a systematic review and Delphi consensus study on the evidence from observational studies Int. J. Geriatr. Psychiatry 30 2015 234 246
15. V.K. Dubey, F. Ansari, D. Vohora, and R. Khanam Possible involvement of corticosterone and serotonin in antidepressant and antianxiety effects of chromium picolinate in chronic unpredictable mild stress induced depression and anxiety in rats J. Trace Elem. Med. Biol. 29 2015 222 226
16. M.R.P. Elmore, R.J. Lee, B.L. West, and K.N. Green Characterizing newly repopulated microglia in the adult mouse: impacts on animal behavior, cell morphology, and neuroinflammation PLoS One 10 2015 e0122912
17. O. Escuredo, L.R. Silva, P. Valentão, M.C. Seijo, and P.B. Andrade Assessing Rubus honey value: pollen and phenolic compounds content and antibacterial capacity Food Chem. 130 2012 671 678
18. C.B. Filho, C.R. Jesse, F. Donato, R. Giacomeli, L. Del Fabbro, M. da Silva Antunes, M.G. de Gomes, A.T. Goes, S.P. Boeira, M. Prigol, and L.C. Souza Chronic unpredictable mild stress decreases BDNF and NGF levels and Na(+),K(+)-ATPase activity in the hippocampus and prefrontal cortex of mice: antidepressant effect of chrysin Neuroscience 289 2015 367 380
19. A.-M. Gao, Z.-P. Ke, F. Shi, G.-C. Sun, and H. Chen Chrysin enhances sensitivity of BEL-7402/ADM cells to doxorubicin by suppressing PI3K/Akt/Nrf2 and ERK/Nrf2 pathway Chem. Biol. Interact. 206 2013 100 108
20. I. Gardner, M. Popovic, N. Zahid, and J.P. Uetrecht A comparison of the covalent binding of clozapine, procainamide, and vesnarinone to human neutrophils in vitro and rat tissues in vitro and in vivo Chem. Res. Toxicol. 18 2005 1384 1394
21. I. Gardner, N. Zahid, D. MacCrimmon, and J.P. Uetrecht A comparison of the oxidation of clozapine and olanzapine to reactive metabolites and the toxicity of these metabolites to human leukocytes Mol. Pharmacol. 53 1998 991 998
22. N. Gresa-Arribas, J. Serratosa, J. Saura, and C. Sola Inhibition of CCAAT/enhancer binding protein delta expression by chrysin in microglial cells results in anti-inflammatory and neuroprotective effects J. Neurochem. 115 2010 526 536
23. S.K. Ha, E. Moon, and S.Y. Kim Chrysin suppresses LPS-stimulated proinflammatory responses by blocking NF-kappaB and JNK activations in microglia cells Neurosci. Lett. 485 2010 143 147
24. S. Habtemariam Flavonoids as inhibitors or enhancers of the cytotoxicity of tumor necrosis factor-α in L-929 tumor cells J. Nat. Prod. 60 1997 775 778
25. M.R. Hadjmohammadi, S. Saman, and S.J. Nazari Separation optimization of quercetin, hesperetin and chrysin in honey by micellar liquid chromatography and experimental design J. Sep. Sci. 33 2010 3144 3151
26. G.K. Harris, Y. Qian, S.S. Leonard, D.C. Sbarra, and X.L. Shi Luteolin and chrysin differentially inhibit cyclooxygenase-2 expression and scavenge reactive oxygen species but similarly inhibit prostaglandin-E-2 formation in RAW 264.7 cells J. Nutr. 136 2006 1517 1521
27. X.L. He, Y.H. Wang, M.G. Bi, and G.H. Du Chrysin improves cognitive deficits and brain damage induced by chronic cerebral hypoperfusion in rats Eur. J. Pharmacol. 680 2012 41 48
28. K.E. Heim, A.R. Tagliaferro, and D.J. Bobilya Flavonoid antioxidants: chemistry, metabolism and structure-activity relationships J. Nutr. Biochem. 13 2002 572 584
29. D.X. Hou, T. Yanagita, T. Uto, S. Masuzaki, and M. Fujii Anthocyanidins inhibit cyclooxygenase-2 expression in LPS-evoked macrophages: structure-activity relationship and molecular mechanisms involved Biochem. Pharmacol. 70 2005 417 425
30. H. Izuta, M. Shimazawa, S. Tazawa, Y. Araki, S. Mishima, and H. Hara Protective effects of Chinese propolis and its component, chrysin, against neuronal cell death via inhibition of mitochondrial apoptosis pathway in SH-SY5Y cells J. Agric. Food Chem. 56 2008 8944 8953
31. Y. Jiang, F.L. Gong, G.B. Zhao, and J. Li Chrysin suppressed inflammatory responses and the inducible nitric oxide synthase pathway after spinal cord injury in rats Int. J. Mol. Sci. 15 2014 12270 12279
32. V.E. Kagan, A.I. Kuzmenko, Y.Y. Tyurina, A.A. Shvedova, T. Matsura, and J.C. Yalowich Pro-oxidant and antioxidant mechanisms of etoposide in HL-60 cells: role of myeloperoxidase Cancer Res. 61 2001 7777 7784
33. N. Kalogeropoulos, A.E. Yanni, G. Koutrotsios, and M. Aloupi Bioactive microconstituents and antioxidant properties of wild edible mushrooms from the island of Lesvos, Greece Food Chem. Toxicol. 55 2013 378 385
34. A.D. Kandhare, V. Shivakumar, A. Rajmane, P. Ghosh, and S.L. Bodhankar Evaluation of the neuroprotective effect of chrysin via modulation of endogenous biomarkers in a rat model of spinal cord injury J. Nat. Med. 68 2014 586 603
35. M.-K. Kang, S.H. Park, Y.J. Choi, D. Shin, and Y.H. Kang Chrysin inhibits diabetic renal tubulointerstitial fibrosis through blocking epithelial to mesenchymal transition J. Mol. Med. 93 2015 759 772
36. S.S. Kang, J.Y. Lee, Y.K. Choi, G.S. Kim, and B.H. Han Neuroprotective effects of flavones on hydrogen peroxide-induced apoptosis in SH-SY5Y neuroblostoma cells Bioorg. Med. Chem. Lett. 14 2004 2261 2264
37. Y.C. Kao, C. Zhou, M. Sherman, C.A. Laughton, and S. Chen Molecular basis of the inhibition of human aromatase (estrogen synthetase) by flavone and isoflavone phytoestrogens: a site-directed mutagenesis study Environ. Health Perspect. 106 1998 85 92
38. C.H. Ko, S.C. Shen, H.Y. Lin, W.C. Hou, W.R. Lee, L.L. Yang, and Y.C. Chen Flavanones structure-related inhibition on TPA-induced tumor promotion through suppression of extracellular signal-regulated protein kinases: involvement of prostaglandin E-2 in anti-promotive process J. Cell. Physiol. 193 2002 93 102
39. X. Li, J.-N. Wang, J.M. Huang, X.K. Xiong, M.-F. Chen, C.N. Ong, H.M. Shen, and X.F. Yang Chrysin promotes tumor necrosis factor (TNF)-related apoptosis-inducing ligand (TRAIL) induced apoptosis in human cancer cell lines Toxicol. in Vitro 25 2011 630 635
40. H. Lim, J.H. Jin, H. Park, and H.P. Kim New synthetic anti-inflammatory chrysin analog, 5, 7-dihydroxy-8-(pyridine-4yl) flavone Eur. J. Pharmacol. 670 2011 617 622
41. K. Lirdprapamongkol, H. Sakurai, S. Abdelhamed, S. Yokoyama, T. Maruyama, S. Athikomkulchai, A. Viriyaroj, S. Awale, H. Yagita, and S. Ruchirawat A flavonoid chrysin suppresses hypoxic survival and metastatic growth of mouse breast cancer cells Oncol. Rep. 30 2013 2357 2364
42. M. Liu, J. Zhang, J. Yang, B. Yang, and W. Cui An efficient synthesis of chrysin J. Chem. Res. 38 2014 134 136
43. P.C. Lv, T.T. Cai, Y. Qian, J. Sun, and H.L. Zhu Synthesis, biological evaluation of chrysin derivatives as potential immunosuppressive agents Eur. J. Med. Chem. 46 2011 393 398
44. M.H. Madeira, R. Boia, P.F. Santos, A.F. Ambrosio, and A.R. Santiago Contribution of microglia-mediated neuroinflammation to retinal degenerative diseases Mediat. Inflamm. 2015 2015 673090
45. N.Z. Mamadalieva, F. Herrmann, M.Z. El-Readi, A. Tahrani, R. Hamoud, D.R. Egamberdieva, S.S. Azimova, and M. Wink Flavonoids in Scutellaria immaculata and S. ramosissima (Lamiaceae) and their biological activity J. Pharm. Pharmacol. 63 2011 1346 1357
46. J.H. Medina, A.C. Paladini, C. Wolfman, M. Levi de Stein, D. Calvo, L.E. Diaz, and C. Pena Chrysin (5,7-di-OH-flavone), a naturally-occurring ligand for benzodiazepine receptors, with anticonvulsant properties Biochem. Pharmacol. 40 1990 2227 2231
47. L.D. Mercer, B.L. Kelly, M.K. Horne, and P.M. Beart Dietary polyphenols protect dopamine neurons from oxidative insults and apoptosis: investigations in primary rat mesencephalic cultures Biochem. Pharmacol. 69 2005 339 345
48. S. Mouffok, H. Haba, C. Lavaud, C. Long, and M. Benkhaled Chemical constituents of Centaurea omphalotricha Coss. and Durieu ex Batt. and Trab Rec. Nat. Prod. 6 2012 292 295
49. H. Park, T.T. Dao, and H.P. Kim Synthesis and inhibition of PGE 2 production of 6, 8-disubstituted chrysin derivatives Eur. J. Med. Chem. 40 2005 943 948
50. F. Pasini, S. Gardini, G.L. Marcazzan, and M.F. Caboni Buckwheat honeys: screening of composition and properties Food Chem. 141 2013 2802 2811
51. S.M. Peng, X.Q. Zou, H.L. Ding, Y.L. Ding, and Y.B. Lin Synthesis and promotion angiogenesis effect of chrysin derivatives coupled to NO donors Bioorg. Med. Chem. Lett. 19 2009 1264 1266
52. O.R. Pereira, A.M. Silva, M.R. Domingues, and S.M. Cardoso Identification of phenolic constituents of Cytisus multiflorus Food Chem. 131 2012 652 659
53. E. Pichichero, R. Cicconi, M. Mattei, M.G. Muzi, and A. Canini Acacia honey and chrysin reduce proliferation of melanoma cells through alterations in cell cycle progression Int. J. Oncol. 37 2010 973 981
54. P.G. Pietta Flavonoids as antioxidants J. Nat. Prod. 63 2000 1035 1042
55. P. Russo, A. Del Bufalo, and A. Cesario Flavonoids acting on DNA topoisomerases: recent advances and future perspectives in cancer therapy Curr. Med. Chem. 19 2012 5287 5293
56. C. Sampath, M. Holbik, L. Krenn, and V. Butterweck Anxiolytic effects of fractions obtained from Passiflora incarnata L. in the elevated plus maze in mice Phytother. Res. 25 2011 789 795
57. J.-S. Shin, K.-S. Kim, M.-B. Kim, J.-H. Jeong, and B.-K. Kim Synthesis and hypoglycemic effect of chrysin derivatives Bioorg. Med. Chem. Lett. 9 1999 869 874
58. B. Singh, D. Singh, and R.K. Goel Dual protective effect of Passiflora incarnata in epilepsy and associated post-ictal depression J. Ethnopharmacol. 139 2012 273 279
59. S. Soboɥanec, V. Šverko, T. Balog, A. Šaric, G. Rusak, S. Likic, B. Kušic, V. Katalinic, S. Radic, and T. Marotti Oxidant/antioxidant properties of Croatian native propolis J. Agric. Food Chem. 54 2006 8018 8026
60. L.C. Souza, M.S. Antunes, C.B. Filho, L. Del Fabbro, M.G. de Gomes, A.T. Goes, F. Donato, M. Prigol, S.P. Boeira, and C.R. Jesse Flavonoid chrysin prevents age-related cognitive decline via attenuation of oxidative stress and modulation of BDNF levels in aged mouse brain Pharmacol. Biochem. Behav. 134 2015 22 30
61. A. Spilsbury, D. Vauzour, J.P.E. Spencer, and M. Rattray Regulation of NF-kappa B activity in astrocytes: effects of flavonoids at dietary-relevant concentrations Biochem. Biophys. Res. Commun. 418 2012 578 583
62. G.M. Sulaiman, K.W. Al Sammarrae, A.H. Ad'hiah, M. Zucchetti, R. Frapolli, E. Bello, E. Erba, M. D'Incalci, and R. Bagnati Chemical characterization of Iraqi propolis samples and assessing their antioxidant potentials Food Chem. Toxicol. 49 2011 2415 2421
63. L.P. Sun, A.L. Chen, H.C. Hung, Y.H. Chien, J.S. Huang, C.Y. Huang, Y.W. Chen, and C.N. Chen Chrysin: a histone deacetylase 8 inhibitor with anticancer activity and a suitable candidate for the standardization of Chinese propolis J. Agric. Food Chem. 60 2012 11748 11758
64. L. Testai, A. Martelli, M. Cristofaro, M.C. Breschi, and V. Calderone Cardioprotective effects of different flavonoids against myocardial ischaemia/reperfusion injury in Langendorff-perfused rat hearts J. Pharm. Pharmacol. 65 2013 750 756
65. S.S. Tian, F.S. Jiang, K. Zhang, X.X. Zhu, B. Jin, J.J. Lu, and Z.S. Ding Flavonoids from the leaves of Carya cathayensis Sarg. inhibit vascular endothelial growth factor-induced angiogenesis Fitoterapia 92 2014 34 40
66. L. Tong, M. Wan, L. Zhang, Y. Zhu, H. Sun, and K. Bi Simultaneous determination of baicalin, wogonoside, baicalein, wogonin, oroxylin A and chrysin of Radix scutellariae extract in rat plasma by liquid chromatography tandem mass spectrometry J. Pharm. Biomed. Anal. 70 2012 6 12
67. P.A. Tsuji, and T. Walle Cytotoxic effects of the dietary flavones chrysin and apigenin in a normal trout liver cell line Chem. Biol. Interact. 171 2008 37 44
68. N. Volpi, and G. Bergonzini Analysis of flavonoids from propolis by on-line HPLC-electrospray mass spectrometry J. Pharm. Biomed. Anal. 42 2006 354 361
69. P.G. Wadibhasme, M.M. Ghaisas, and P.A. Thakurdesai Anti-asthmatic potential of chrysin on ovalbumin-induced bronchoalveolar hyperresponsiveness in rats Pharm. Biol. 49 2011 508 515
70. T. Walle, Y. Otake, J.A. Brubaker, U.K. Walle, and P.V. Halushka Disposition and metabolism of the flavonoid chrysin in normal volunteers Br. J. Clin. Pharmacol. 51 2001 143 146
71. U.K. Walle, A. Galijatovic, and T. Walle Transport of the flavonoid chrysin and its conjugated metabolites by the human intestinal cell line Caco-2 Biochem. Pharmacol. 58 1999 431 438
72. U.K. Walle, A. Galijatovic, and T. Walle Transport of the flavonoid chrysin and its conjugated metabolites by the human intestinal cell line Caco-2 Biochem. Pharmacol. 58 1999 431 438
73. Q.Q. Wang, N. Cheng, W.B. Yi, S.M. Peng, and X.Q. Zou Synthesis, nitric oxide release, and α-glucosidase inhibition of nitric oxide donating apigenin and chrysin derivatives Bioorg. Med. Chem. 22 2014 1515 1521
74. C.A. Williams, J.B. Harborne, M. Newman, J. Greenham, and J. Eagles Chrysin and other leaf exudate flavonoids in the genus Pelargonium Phytochemistry 46 1997 1349 1353
75. C. Wolfman, H. Viola, A. Paladini, F. Dajas, and J.H. Medina Possible anxiolytic effects of chrysin, a central benzodiazepine receptor ligand isolated from Passiflora caerulea Pharmacol. Biochem. Behav. 47 1994 1 4
76. R.Y. Yan, Y.Y. Cao, C.Y. Chen, H.Q. Dai, S.X. Yu, J.L. Wei, H. Li, and B. Yang Antioxidant flavonoids from the seed of Oroxylum indicum Fitoterapia 82 2011 841 848
77. Y. Yao, L. Chen, J.T. Xiao, C.Y. Wang, W. Jiang, R.X. Zhang, and J.W. Hao Chrysin protects against focal cerebral ischemia/reperfusion injury in mice through attenuation of oxidative stress and inflammation Int. J. Mol. Sci. 15 2014 20913 20926
78. W. Zeng, Y. Yan, F. Zhang, C. Zhang, and W. Liang Chrysin promotes osteogenic differentiation via ERK/MAPK activation Protein Cell 4 2013 539 547
79. T. Zhang, X. Chen, L. Qu, J. Wu, R. Cui, and Y. Zhao Chrysin and its phosphate ester inhibit cell proliferation and induce apoptosis in HeLa cells Bioorg. Med. Chem. 12 2004 6097 6105
80. Z. Zhang, G. Li, S.S. Szeto, C.M. Chong, Q. Quan, C. Huang, W. Cui, B. Guo, Y. Wang, Y. Han, K.W. Michael Siu, S.M. Yuen Lee, and I.K. Chu Examining the neuroprotective effects of protocatechuic acid and chrysin on in vitro and in vivo models of Parkinson disease Free Radic. Biol. Med. 84 2015 331 343
81. Z.J. Zhang, L.C. Cheang, M.W. Wang, G.H. Li, I.K. Chu, Z.X. Lin, and S.M. Lee Ethanolic extract of fructus Alpinia oxyphylla protects against 6-hydroxydopamine-induced damage of PC12 cells in vitro and dopaminergic neurons in zebrafish Cell. Mol. Neurobiol. 32 2012 27 40
82. J.T. Zhu, R.C. Choi, G.K. Chu, A.W. Cheung, Q.T. Gao, J. Li, Z.Y. Jiang, T.T. Dong, and K.W. Tsim Flavonoids possess neuroprotective effects on cultured pheochromocytoma PC12 cells: a comparison of different flavonoids in activating estrogenic effect and in preventing beta-amyloid-induced cell death J. Agric. Food Chem. 55 2007 2438 2445
83. Z.Y. Zhu, W.X. Wang, Z.Q. Wang, L.J. Chen, J.Y. Zhang, X.C. Liu, S.P. Wu, and Y.M. Zhang Synthesis and antitumor activity evaluation of chrysin derivatives Eur. J. Med. Chem. 75 2014 297 300
84. X.Q. Zou, S.M. Peng, C.P. Hu, L.F. Tan, Q. Yuan, H.-W. Deng, and Y.J. Li Synthesis, characterization and vasculoprotective effects of nitric oxide-donating derivatives of chrysin Bioorg. Med. Chem. 18 2010 3020 3025