• Biomolecules & Therapeutics
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• v.9 no.1
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• pp.15-19
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• 2001

The derivative of chrysin 7-O-cyclopropanecarboxylate was synthesized by condensing cyclopropanecarboxylic acid with chrysin in organic solvent, and its structure was identified by NMR, MS, UV IR etc. We also investigated the physico-chemical properties, anti-diabetic effect and set up the quantitative analytical method of this compound. The correlation coefficient of calibration curve on this compound was approximately 0.9985 by absorption spectrophotometry. And, this study was carried out to investigate the hair-growth effect of chrysin derivative to the black mouse (C57BL/6). When this derivative in ethanol solution was administered to the back of mouse by method of skin paste, this derivative promoted the hair growth of mouse.

• YAKHAK HOEJI
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• v.43 no.3
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• pp.316-319
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• 1999

Chrysin 7-Ο-crotonate was synthesized by condensing crotonic acid with chrysin in organic solvent, tetrahydrofuran (THF) using dicyclohexylcarbodiimide (DCC) and 4-dimethylaminopyridine (DMAP). Its structure was indentified by NMR, MS, UV, IR etc. We also investigated the physico-chemical properties and set up the quantitative anytical method of this compound. The correlation coefficient of calibration curve measured at the isobestic point (340 nm) on this compound was approximately 0.9994 by absorption spetrophtometry. Detection limit was 1.6ng at S/N=3 by using a RP column by HPLC. The hair growth effect fo chrysin 7-Ο-crotonate on the hair of black mouse (C57BL/6), was carried out using paste method. When its ethanol solution was administered to this black mouse by route of skin, this compound promoted the growth of hair.

• YAKHAK HOEJI
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• v.56 no.3
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• pp.198-203
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• 2012

Chrysin and chlorogenic acid are natural products derived from Scutellariae Radix and Lonicerae Flos, respectively. We examined whether chrysin and chlorogenic acid affect airway mucin production induced by TNF-${\alpha}$ in NCI-H292 cells. Cells were pretreated with each agent for 30 min and then stimulated with TNF-${\alpha}$ for 24 h. Of the two compounds, chrysin suppressed airway MUC5AC mucin production. Also, chrysin suppressed MUC5AC mucin gene expression and translocation of NF-${\kappa}B$ p65 induced by TNF-${\alpha}$. This result suggests that chrysin can regulate the production and gene expression of mucin induced by TNF-${\alpha}$ through the inactivation of NF-${\kappa}B$ in airway epithelial cells.

• Biomolecules & Therapeutics
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• v.23 no.5
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• pp.465-470
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• 2015

Chrysin is a 5,7-dihydroxyflavone and was recently shown to potently inhibit enterovirus 71 (EV71) by suppressing viral 3C protease ($3C^{pro}$ activity. In the current study, we investigated whether chrysin also shows antiviral activity against coxsackievirus B3 (CVB3), which belongs to the same genus (Enterovirus) as EV71, and assessed its ability to prevent the resulting acute pancreatitis and myocarditis. We found that chrysin showed antiviral activity against CVB3 at $10{\mu}M$, but exhibited mild cellular cytotoxicity at $50{\mu}M$, prompting us to synthesize derivatives of chrysin to increase the antiviral activity and reduce its cytotoxicity. Among four 4-substituted benzyl derivatives derived from C(5) benzyl-protected derivatives 7, 9-11 had significant antiviral activity and showed the most potent activity against CVB3 with low cytotoxicity in Vero cells. Intraperitoneal injection of CVB3 in BALB/c mice with $1{\times}10^6TCID_{50}$ (50% tissue culture infective dose) of CVB3 induced acute pancreatitis with ablation of acinar cells and increased serum CXCL1 levels, whereas the daily administration of 9 for 5 days significantly alleviated the pancreatic inflammation and reduced the elevation in serum CXCL1 levels. Collectively, we assessed the anti-CVB3 activities of chrysin and its derivatives, and found that among 4-substituted benzyl derivatives, 9 exhibited the highest activity against CVB3 in vivo, and protected mice from CVB3-induced pancreatic damage, simultaneously lowering serum CXCL1 levels.

• Archives of Pharmacal Research
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• v.19 no.6
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• pp.514-519
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• 1996

In order to understand the mechanism of action of flavonoids on the drug metabolizing enzyme, cytochrome P450IA1, this study was undertaken to examine the effect of chrysin, morin, myricetin and aminopyrine on the activities of ethoxyresorufin O-deethylase and benzo(.alpha.) pyrene hydroxylase in the liver. In the isolated perfused rat liver that was pretreated with 3-methylcholanthrene (3MC), chrysin, morin, myricetin and aminopyrine inhibited the activity of ethoxyresorufin O-deethylase with concentration dependent manner. The isolated liver perfusion with chrysin, morin, myricetin and aminopyrine showed inhibition on the induction of ethoxyresorufin O- deethylase by 3MC. And also, in mouse liver hepa I cells, 3MC-stimulated the benzo(.alpha.)pyrene hydroxylase activity which was inhibited by chrysin, morin, myricetin and aminopyrine. These results strongly suggested that hydoxylated flavonoids interfered not only the induction of cytochrome P45OIA1 enzymes by 3MC but also the interaction of substrates and enzyme.

• Asian Pacific Journal of Cancer Prevention
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• v.16 no.9
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• pp.3753-3758
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• 2015

Background: Polymeric nanoparticles are attractive materials that have been widely used in medicine for drug delivery, with therapeutic applications. In our study, polymeric nanoparticles and the anticancer drug, chrysin, were encapsulated into poly (D, L-lactic-co-glycolic acid) poly (ethylene glycol) (PLGA-PEG) nanoparticles for local treatment. Materials and Methods: PLGA: PEG triblock copolymers were synthesized by ring-opening polymerization of D, L-lactide and glycolide as an initiator. The bulk properties of these copolymers were characterized using 1H nuclear magnetic resonance spectroscopy and Fourier transform infrared spectroscopy. In addition, the resulting particles were characterized by scanning electron microscopy. Results: The chrysin encapsulation efficiency achieved for polymeric nanoparticles was 70% control of release kinetics. The cytotoxicity of different concentration of pure chrysin and chrysin loaded in PLGA-PEG ($5-640{\mu}M$) on T47-D breast cancer cell line was analyzed by MTT-assay. Conclusions: There is potential for use of these nanoparticles for biomedical applications. Future work should include in vivo investigation of the targeting capability and effectiveness of these nanoparticles in the treatment of breast cancer.

• Journal of Life Science
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• v.29 no.5
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• pp.607-613
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• 2019

The purpose of this study was to investigate the effects of either chrysin or exercise on the inflammasome and thermogenic markers in the livers of high-fat fed mice. C57BL/6 mice were randomly assigned to four groups: normal diet control (NC; n=5), high-fat diet control (HC; n=5), high-fat diet with chrysin (Hch; n=5), and high-fat diet with moderate exercise (HME; n=5). The mice were fed a high-fat diet (60% of calories from fat) or normal diet (18% of calories from fat). Chrysin was supplemented orally as 50mg/kg/day dissolved in a 0.1ml solution of dimethyl sulfoxide. The exercised mice ran on a treadmill at 12-20 m/min for 30-60 min/day, 5 times/week, for 16 weeks. After the intervention, the epididymal fat and liver weights were significantly decreased in the HME group compared with HC and Hch groups. The adipocyte size was effectively decreased in the Hch and HME groups compared with the HC group. The inflammasome markers NLRP3, $IL-1{\beta}$, and caspase1 were significantly decreased in the Hch and HME groups compared with the HC group. The thermogenic markers $PGC-1{\alpha}$ and BMP7 were significantly lower in the HC than in the NC group. However, the HME group showed an increase in the thermogenic markers. In conclusion, chrysin and moderate exercise have positive effects on obese metabolic complications induced by high-fat diets by reducing inflammasome genes. However, chrysin supplementation had no effect on thermogenic gene expression. Moderate exercise would therefore seem to be more effective in controlling obesity-induced metabolic deregulation.

• Korean Journal of Pharmacognosy
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• v.48 no.1
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• pp.88-92
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• 2017

In the present study, we carried out quantitative analysis of chrysin and pinocembrin in Korean propolis by ultra performance liquid chromatography (UPLC) equipped with diode array detector. The separation was done using BEH C18 ($2.1{\times}50mm$, $1.7{\mu}m$) column with a mobile phase consisting of MeCN and 0.1% $H_3PO_4$ at 280 nm. The chromatographic method was validated for specificity, limit of detection, limit of quantification, linearity, precision, and accuracy. A quantitative analysis exhibited that the contents of the two compounds in Korean propolis collected from 8 inland areas except Jeju-do ranged from 3.1-46.0 mg/g. These results will be valuable as basic data for standardization of Korean propolis.

• Natural Product Sciences
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• v.23 no.1
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• pp.46-52
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• 2017

The aim of this study was to evaluate the anti-Helicobacter pylori activity of fractions and major aglycon compounds (baicalein, chrysin, oroxylin A, wogonin) of Scutellariae Radix. Minimum inhibitory concentration (MIC) measurement, DPPH radical-scavenging assay, DNA protection assay, and urease inhibition analysis were performed. The ethyl acetate (EtOAc) fraction showed the potent anti-Helicobacter activity, and therefore, compounds in the EtOAc fraction were subjected to further assay. The MICs of chrysin, oroxylin A, and wogonin against Helicobacter pylori 26695 were 6.25, 12.5 and $25{\mu}g/mL$, respectively. Baicalein exhibited the most effective DPPH radical-scavenging activity. DNA protection using Fenton reaction, chrysin, oroxylin A, and wogonin showed effective DNA protective effect. This result was also confirmed by quantitative real-time polymerase chain reaction (qRT-PCR). Regarding Jack bean urease (0.5 mg/mL, 50 unit/mg) inhibition, 20 mM ofbaicalein and chrysin inhibited urease activity by 88.2% and 72.5%, respectively.

• Archives of Pharmacal Research
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• v.28 no.10
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• pp.1114-1121
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• 2005

Flavonoids are polyphenols composed of two aromatic rings (A, B) and a heterocyclic ring (C). In order to determine the effects of the number of hydroxyl groups in the B-ring of the flavonoids on human cytochrome P450 (CYP) 1 family enzymes, we evaluated the inhibition of CYP1A-dependent 7-ethoxyresorufin O-deethylation activity by chrysin, apigenin and luteolin, using bacterial membranes that co-express human CYP1A1, CYP1A2, or CYP1B1 with human NADPH-cytochrome P450 reductase. Chrysin, which possesses no hydroxyl groups in its B-ring, exhibited the most pronounced inhibitory effects on CYP1A2-dependent EROD activity, followed by apigenin and luteolin. On the contrary, CYP1A1-mediated EROD activity was most potently inhibited by luteolin, which is characterized by two hydroxyl groups in its B-ring, followed by apigenin and chrysin. However, all of the 5,7-dihydroxyflavones were determined to similarly inhibit CYP1B1 activity. Chrysin, apigenin, and luteolin exhibited a mixed-type mode of inhibition with regard to CYP1A2, CYP1B1, and CYP1A1, with apparent Ki values of 2.4, 0.5, and 2.0 ${\mu}M$, respectively. These findings suggested that the number of hydroxyl groups in the B-ring of 5,7-dihydroxyflavone might have some influence on the degree to which CYP1A enzymes were inhibited, but not on the degree to which CYP1B1 enzymes were inhibited.