• Bulletin of the Korean Chemical Society
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• v.26 no.11
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• pp.1701-1705
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• 2005

We have established an efficient method for the synthesis of the arylpiperazine derivatives in which the acylation of 2-aminopyridine, the coupling reaction of the acyl compound with piperazines, and reduction of the arylpiperazines were performed under a microwave irradiation (300 W) to afford the corresponding target compounds in quantitative yields. In all cases, the reaction times were remarkably reduced when compared with those of the conventional method.

• Bulletin of the Korean Chemical Society
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• v.33 no.8
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• pp.2597-2602
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• 2012

Novel 1,4-substituted piperazine derivatives 5, Series A and B were designed by fragment analysis and molecular modification of 4 selected piperazine-containing compounds which possess antidepressant activity. We synthesized new 39 analogues of Series A and 10 compounds of Series B, respectively. The antidepressant screening against DA, NE, and serotonin neurotransmitter uptake inhibition was carried out using the Neurotransmitter Transporter Uptake Assay Kit. The compounds in Series B showed relatively higher reuptake inhibitory activity for SERT, NET, and DAT than those in Series A. The length of spacer between the central piperazine core and the terminal phenyl ring substituted at the piperazine ring in Series B seems to exert an important role in the activity.

• Korean Journal of Plant Resources
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• v.32 no.5
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• pp.423-432
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• 2019

In order to select potential plant resources as functional materials and natural antioxidants, we evaluated antioxidant activity and serotonin derivatives of safflower germplasm collected from five countries. N-(p-Coumaroyl) serotonin (CS) and N-feruloylserotonin (FS) were analyzed by using Ultra Performance Liquid Chromatography (UPLC). Total polyphenol content (TPC) was determined by Folin-Ciocalteu method and antioxidant activities were estimated by 2,2-diphenyl-1-picryl-hydrazil (DPPH), 2,2'-azino-bis(3-ethylbenzothiazoline-6-sulphonic acid) diammonium salt (ABTS), Ferric reducing antioxidant power (FRAP) and Reducing power (RP) assays. The TPC showed a range of 28.25 to $90.53{\mu}g$ gallic acid equivalent (GAE)/mg dried extract (DE). DPPH, ABTS, FRAP and RP assay were in the range of 18.76 to 93.98, 48.91 to 163.73, 3.80 to 132.29 and 26.32 to $80.08{\mu}g$ ascorbic acid equivalent (ASCE)/mg DE, respectively. Among the five countries, safflower seed collected from Iran had the highest levels of serotonin derivatives and antioxidant activities than other countries (p<0.05). CS showed high correlation with TPC, ABTS and DPPH (r=0.673,0.727,0.820), and FS showed high correlation with DPPH (r=0.740). Accessions IT321214 and IT321215 could be useful for development of new functional materials and could be used as a source of valuable natural antioxidant materials.

• Korean Journal of Food Science and Technology
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• v.38 no.2
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• pp.279-283
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• 2006

This study was conducted to examine the effect of polyphenols from safflower seed on HMG-CoA reductase (HMGR) activity, LDL oxidation and Apo A1 secretion from Hep3B cell. The safflower seed polyphenols were matairesinol (Iignan), enterolactone (lignan metabolite), acacetin (flavone) and serotonin derivative. In addition to safflower polyphenols, mevastatin, ${\alpha}-estradiol,\;{\alpha}-tocopherol$ and soy genistein were tested as reference compounds depending on the type of the test. HMGR source was liver microsome obtained from rat fed 2% cholestyramine for 10 days. Inhibition of HMGR activity was greater with mevastatin (53%) than safflower serotonin derivatives (45%), followed by genistein (35%), but was very small with matairesinol, enterolactone and acacetin. LDL oxidation induced by $CuSO_4$ was suppressed by all the test material used in the present study and in the order of safflower serotonin derivatives> matairesinol > ${\beta}-estradiol$ > genistein > acacetin > enterolactone. Apo A1 secretion from Hep3B cell was significantly stimulated by mevastatin, but moderately (p<0.1) by ${\beta}-estradiol$ and genistein as well as enterolactone. These results suggest that the safflower polyphenols improve body lipid status via inhibition of cholesterol synthesis and suppression of LDL oxidation.

• Biomolecules & Therapeutics
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• v.31 no.2
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• pp.176-182
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• 2023

Among 14 subtypes of serotonin receptors (5-HTRs), 5-HT_2AR plays important roles in drug addiction and various psychiatric disorders. Agonists for 5-HT_2AR have been classified into three structural groups: phenethylamines, tryptamines, and ergolines. In this study, the structure-activity relationship (SAR) of phenethylamine and tryptamine derivatives for binding 5-HT_2AR was determined. In addition, functional and regulatory evaluation of selected compounds was conducted for extracellular signal-regulated kinases (ERKs) and receptor endocytosis. SAR studies showed that phenethylamines possessed higher affinity to 5-HT_2AR than tryptamines. In phenethylamines, two phenyl groups were attached to the carbon and nitrogen (R³ ) atoms of ethylamine, the backbone of phenethylamines. Alkyl or halogen groups on the phenyl ring attached to the β carbon exerted positive effects on the binding affinity when they were at para positions. Oxygen-containing groups attached to R³ exerted mixed influences depending on the position of their attachment. In tryptamine derivatives, tryptamine group was attached to the β carbon of ethylamine, and ally groups were attached to the nitrogen atom. Oxygen-containing substituents on large ring and alkyl substituents on the small ring of tryptamine groups exerted positive and negative influence on the affinity for 5-HT_2AR, respectively. Ally groups attached to the nitrogen atom of ethylamine exerted negative influences. Functional and regulatory activities of the tested compounds correlated with their affinity for 5-HT_2AR, suggesting their agonistic nature. In conclusion, this study provides information for designing novel ligands for 5-HT_2AR, which can be used to control psychiatric disorders and drug abuse.

• Bulletin of the Korean Chemical Society
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• v.27 no.12
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• pp.1969-1975
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• 2006

3D-QSAR model that correlates the biological activities with the chemical structures of quipazine derivatives acting on the serotonine transporter (SERT) was developed by comparative molecular field analysis (CoMFA). Total 8 models were constructed and a more accurate model, using close 1 $\AA$ grid spacing and StDev*Coefficients weight value gave better results. The contour maps with the best model, the resulting cross-validated correlation ($q^2$ : 0.744), and non-cross-validated correlation ($r^2$ : 0.966) indicate the steric and electrostatic environment of inhibitors in the SERT binding pocket. This study can be used as a putative picture of the pharmacophore in the design of novel and potent inhibitors.

• Journal of the Korean Society of Food Science and Nutrition
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• v.31 no.3
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• pp.367-372
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• 2002

In order to utilize safflower seed effectively as a food material, it was processed at the conditions including roasting temperature/time of 170$\^{C}$/10 min to 210$\^{C}$/30 min, ethanol concentration of 0 to 100% (V/V) and enzyme hydrolysis with $\alpha$-amylase, $\beta$-amylase, amyloglucosidase and cellulase. Safflower seed extracts had the highest soluble solid content at the condition of 60% ethanol concentration, roasting at 190$\^{C}$ for 20 min and hydrolysis with amyloglucosidase. Total phenolic compounds increased with the ethanol concentration, showing the highest at the condition of 80% ethanol, roasting at 170$\^{C}$ for 30 min and hydrolysis with amyloglucosidase. High level total flavonoid was observed at the condition of 80% ethanol, roasting at 210$\^{C}$ for 30 min and hydrolysis with amyloglucosidase. Safflower seed had sucrose as major free sugar as well as xylose and arabinose as minor free sugars. Organic acids in safflower seed included oxalic, citric, magic and fumaric acid. Serotonin I (N-[2-(5-hydroxy-1H-indo-1-3-yl)ethyl]ftrulamide) and serotonin II (N-[2-(5-hydroxy-1H-indol-3yl)ethyl]-p-coumaramide) as antioxidant compounds increased with ethanol concentration, showing the highest revel at 60% ethanol. Acacetin content increased with temperature and roasting time, with a maximum of 69.47 mg% at 210$\^{C}$ for 30 min.

• Korean Journal of Food Science and Technology
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• v.34 no.4
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• pp.617-624
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• 2002

Health drinks were prepared with freeze dried powder of 60% ethanol extract (60% EFDP), 60% ethanol extract after hydrolysis with amyloglucosidase (60% AEFDP) and 80% ethanol extract (80% EFDP) from roasted safflower seed. Quality characteristics and antioxidative properties were investigated. Yield of freeze dried powders were ranged in $4.67%{\sim}5.62%$. Brix, pH and titratable acidity of safflower drinks were ranged in $11.4{\sim}14.2%$, $2.83{\sim}3.34$ and $0.09{\sim}0.91%$, respectively. Content of total phenolic compounds was much more in 80% EFDP (117 mg/g) and safflower drink-I (SD-I, 440 ppm) than others. Content of total flavonoid was observed in higher level in 60% EFDP (49 mg/g) and safflower drink-V (SD-V, 138 ppm) than others. Antioxidant compounds such as N-[2-(5-hydroxy-1H-indol-3-yl)ethyl]ferulamide(serotonin-I) and N-[2-(5-hydroxy-1H-indol-3yl)ethyl]-p-coumaramide(serotonin-II) exhibited higher contents of 21.09 ppm, 33.56 ppm in 60% EFDP and of 3.83 ppm, 5.81 ppm in safflower drink-II (SD-II) than others. Content of acacetin was much more in 80% EFDP (13.53 ppm) and safflower drink-IV (SD-IV, 1.14 ppm) than others. From the DPPH test to measure antioxidant activity, it was shown that 80% EFDP and SD-I have stronger scavenging activities of 94.58% and 94.88%, respectively, while BHA standard solution does 93.88%. Among drinks, SD-II was revealed to have highest level on overall acceptance, color and flavor through sensory evaluation. These results induced that safflower seed can be used as natural antioxidant and functional food material.

• The Journal of the Korea Contents Association
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• v.9 no.11
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• pp.262-270
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• 2009

$^{18}F$-mefway has been developed as radioligand for serotonin receptor 5-$HT_{1A}$. The object of this study was to obtain the mefway precursor with the higher yield than previous method and to identify whether $^{18}F$-mefway can bind to 5-$HT_{1A}$ or not. from microPET imaging of small animal brain. Precursor was prepared by a modification of the reported procedure then [$^{18}F$] labeling was performed by adding $^{18}F$ ion at $130^{\circ}C$ in the hot cell for 30min. After purification of reaction mixture using alumina Sep-pak and HPLC, microPET images of small animal brain were determined. The chemical yield of precursor was increased from 9% to 34% using oxalyl chloride and LAH/diethylether. We synthesized a precursor which was successfully labeled with no-carrier-added $^{18}F$-by new synthetic route. This research suggest that $^{18}F$-mefway will be used a radiopharmaceutical for evaluation of central nerve system disorder as imaging a gent for 5-$HT_{1A}$ receptor.

• Journal of the Korean Society of Food Science and Nutrition
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• v.37 no.9
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• pp.1162-1167
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• 2008

This study was to investigate the chemical compositions of germinated (GSS)- and ungerminated (UGSS)-safflower (Carthamus tinctorius) seeds. GSS had higher amount of sugar and crude fiber than UGSS, but less amounts of protein and lipid. Levels of $\alpha$-tocopherol and essential amino acids of GSS were higher than those of UGSS, although there are no difference in fatty acid composition between GSS and UGSS. Among the nine phenolic compounds detected, five phenolic compounds, except for two lignans and two flavonoids, were found in both GSS and UGSS. Four serotonin derivatives accounted for about 80 per cent of total phenolic compounds, and levels of five phenolic compounds decreased slightly with germination. These results suggest that germination may enhance the functionality of safflower seed by increasing nutritional compositions and by decreasing phenolic compounds with bitter taste and cathartic effects.