• Title/Summary/Keyword: 페놀유도체

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Synthesis of Cyclen-Based Copper Complexes as a Potential Estrogen Receptor Ligand (에스트로젠 수용체 리간드로서 사이클렌을 기본 구조로 한 구리 착물의 합성)

  • Park, Jeong-Chan;Pandya, Darpan N.;Jeon, Hak-Rim;Lee, Sang-Woo;Ahn, Byeong-Cheol;Lee, Jae-Tae;Yoo, Jeong-Soo
    • Nuclear Medicine and Molecular Imaging
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    • v.41 no.4
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    • pp.326-334
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    • 2007
  • Purpose: The estrogen receptor (ER), which is over-expressed in ER-positive breast tumors, has been imaged by positron emission tomography (PET) using $[^{18}F]$ labeled estrogen ligands, especially $[^{18}F]FES$. However, $[^{18}F]$ has relatively short-lived half-life ($t_{1/2}$ =1.8 h) and the labeling yield of radio-fluorination is usually low compared with $^{64}Cu\;(t_{1/2}=12.7\;h)$. 1,4,7,10-tetraazacyclododecane (cyclen) is used to form stable metal complexes with copper, indium, gallium, and gadolinium. With these in mind, we prepared cyclen-based Cu complexes which mimic estradiol in aspect of two hydroxyl groups. Materials and Methods: 1.7-Protected cyclen, 1.7-bis (benzyloxycarbonyl)-cyclen was synthesized according to the reported procedure. After introducing two 4-benzyloxybenzyl groups at 4,10-positions, the benzyloxycarbonyl and benzyl groups were removed at the same time by hydrogenation on Pd/C to give 1,7-bis(4-hydroxybenzyl)-1,4,7,10-tetraazacyclododecane (1). Results: The prepared ligand 1 was fully characterized by $^1H,\;^{13}C$ NMR, and mass spectrometer. The synthesized ligand was reacted with copper chloride and copper perchlorate to give copper complexes $[Cu(1)]^{2+}2(CIO_4^-)\;and\;[Cu(1)Cl]^+Cl^-$ which were confirmed by high-resolution mass (FAB). Conclusion: We successfully synthesized a cyclen derivative of which two phenol groups are located on trans position of N-atoms. And, two Cu(ll) complexes of +2 and +1 overall charge, were prepared as a potential PET tracers for ER imaging.

Antioxidative and Anti-Diabetes Activity, and Free Amino Acid and Mineral Contents of Beverage with Gugija (Lycii fructus) Extracts (구기자 추출물 함유 음료의 산화방지활성, 항당뇨효과, 유리아미노산과 무기질 함량)

  • Lee, Kyong-Ae
    • Korean journal of food and cookery science
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    • v.31 no.2
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    • pp.207-213
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    • 2015
  • Free amino acid and mineral analysis of beverages with Gugija (Lycii fructus) extracts performed to determine the antioxidative and anti-diabetes activities of the beverages. The four major free amino acids in the water- or ethanol-extracts of the Gugija beverages were asparagine (115.23, 51.95 mg%), methionine (20.02, 22.07 mg%), aspartic acid (19.65, 13.72 mg%) and taurine (18.64, 22.44 mg%). The mineral contents of the Gugija beverages with water- and ethanol-extracts were in the order K>Mg>Na>Ca>Zn>Fe. Antioxidant activity determined by DPPH and ABTS radical scavenging activity. There was no significant difference in DPPH and ABTS radical scavenging activities between the water-extract beverages and the ethanol-extract beverages, although more phenolics and flavonoids were found in the ethanol-extract beverage. Higher anti-${\alpha}$-glucosidase activity was observed in the ethanol-extract beverage compared to acabose, which was used as the control and is an inhibitor of ${\alpha}$-glucosidase, suggesting that the Gugija beverage with ethanol extract could be a potential hypoglycemic agent.

Quantitative Determination of Phenol in Water Using GC-MS after Liquid-Liquid Extraction and Acetylation (액-액 추출과 아세틸화 후 GC-MS를 이용한 물 중 phenol의 분석)

  • Park, Sunyoung;Kim, Yunjeong;Jung, Sungjin;Kim, Hekap
    • Korean Journal of Environmental Agriculture
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    • v.36 no.1
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    • pp.63-66
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    • 2017
  • BACKGROUND: The phenol concentrations in water samples were determined using gas chromatography after derivatization of the analyte to phenyl acetate followed by extraction using a large volume of solvent. However, this procedure requires an additional purification step and is not analytically efficient. METHODS AND RESULTS: In this study, phenol was first extracted from an acidified water sample using ethyl acetate and then acetylated using acetic anhydride in the presence of a small amount of water and $K_2CO_3$. The derivative was extracted using 1mL of n-butyl acetate. One microliter of the extract was analyzed by GC-MS without further purification. The calibration curve showed good linearity with the $r^2$ value of 0.9968. The method detection limit and the limit of quantitation were estimated to be $0.18{\mu}g/L$ and $0.56{\mu}g/L$, respectively. Repeatability (RSD, n=3) and recovery (n=3) were 9.1%-4.3% and 90.6%-110.5%, respectively. The concentrations of phenol in a few samples of stream water were distributed in the range of $2.51-7.51{\mu}g/L$. CONCLUSION: This method is simpler and faster to implement than those currently utilized and shows high analytical reliability. It can be applied to the quantitative determination of phenol concentrations in surface water and groundwater samples.

Composition and Contents of Free Amino Acids and Phenolic Acid and Flavonoids of Imperata cylindrica Beauvois var. koenigii Root extracts (백모근 추출물의 유리아미노산 및 Phenolic acid와 Flavonoids 조성 및 함량)

  • Lee, Soon-suk;Lee, Keun-Kwang
    • Journal of Digital Convergence
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    • v.18 no.7
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    • pp.397-403
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    • 2020
  • This study was carried out to investigate the free amino acid and derivatives and phenolic acid and flavonoid compositions and contents of hot water and 95% ethanol extracts of Imperata cylindrica Beauvois var. koenigii root. The purpose of this study is to obtain basic data and to confirm their applicability as functional cosmetic and functional food ingredients on extracts. 15 kinds and 9 kinds of free amino acids were detected in both extracts, respectively. 5 kinds and 4 kinds of protein free-amino acid derivatives were detected in both extracts, respectively. Total phenol contents were 116.50 ± 0.06 and 140.10 ± 0.04 mg% in both extracts, respectively. The total flavonoid contents were 31.80 ± 0.03 and 43.90 ± 0.05 mg% in both extracts, respectively. 5 kinds and 6 kinds of phenolic acids were detected in both extracts, respectively. In the case of flavonoid analysis, no flavonoid compound was detected in the hot water extract while taxifolin was identified in the 95% ethanol extract. Based on the above results, the hot water and 95% ethanol extracts of I. cylindrica Beauvois var. koenigii root are rich in free amino acids, amino acid derivatives, phenolic acids and flavonoids which confirm their potential for applications in cosmeceuticals, nutricosmetics formulations and functional foods.

Development of Analytical Method for Rutin in Buckwheat Plant using High Performance Liquid Chromatography (메밀 식물체 함유 Rutin의 HPLC 분석방법 개발)

  • Choung Myoung-Gun
    • KOREAN JOURNAL OF CROP SCIENCE
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    • v.50 no.spc1
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    • pp.181-186
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    • 2005
  • This experiment was conducted to know the appropriate methods for extraction and determination of rutin contained buckwheat plants. The efficient HPLC analytical condition of rutin contained buckwheat plants was developed. The gradient elution employed a $250mm\times4.6mm$ i.d. Tosoh ODS 120T column. The gradient system was used two mobile phases. A gradient elution was performed with mobile phase A, consisting of $2\%$ Acetic $acid-45\%$ Acetonitrile, and mobile phase B, comprising $2\%$ aqueous acetic acid, and delivered at a flow rate of 1mL/min as follows: 0-18 min, $50-100\%$ A; 18-20 min, $100-50\%$ A; 20-22 min, $50\%$ A. The UV detection wavelength was set at 355 nm. The limit of detection (LOD) for rutin standard compound was 20 ng/mL. And, the higher content of rutin in the extracts was obtained by $80^{\circ}C$ reflex extraction for 120 min. from plants of buckwheat using ethanol.

The Pharmacological Activity of Coffee Fermented Using Monascus purpureus Mycelium Solid-state Culture Depends on the Cultivation Area and Green Coffees Variety (원산지 및 품종에 따라 조제된 홍국균 균사체-고체발효 원두커피의 생리활성)

  • Kim, Hoon;Yu, Kwang-Won;Lee, Jun-Soo;Baek, Gil-Hun;Shin, Ji-Young
    • Korean Journal of Food Science and Technology
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    • v.46 no.1
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    • pp.79-86
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    • 2014
  • In previous work, we fermented coffee beans using solid-state culture with various fungal mycelia to enhance the physiological activity of the coffee. The coffee fermented with Monascus sp. showed a higher physiological activity than non-fermented coffee or other coffees fermented with mushroom mycelium. The aim of this study was to characterize the various fermented coffees with respect to their area of cultivation and their variety using Monascus purpureus (MP) mycelium solid-state culture. Thirty types of green coffee beans, which varied in terms of their cultivation area or variety, were purchased from different suppliers and fermented with MP under optimal conditions. Each MP-fermented coffee was medium roasted and extracted further using hot water (HW) under the same conditions. Of the HW extracts, those derived from MP-Mandheling coffees had the highest yield (13.6-15.5%), and MP-Robusta coffee showed a significantly higher polyphenolic content (3.03 mg gallic acid equivalent/100 mg) and 2,2'-azino-bis(3-ethylbenzthiazoline-6-sulphonic acid) free radical scavenging activity (27.11 mg ascorbic acid equivalent antioxidant capacity/100 mg). Furthermore, in comparison to other MP-fermented coffees at $1,000{\mu}g/mL$, MP-Robusta coffee showed not only the most effective inhibition of tumor necrosis factor-${\alpha}$ (TNF-${\alpha}$) production in LPS-stimulated RAW 264.7 cells (67.1% of that in LPS-stimulated control cells), but also an effective inhibition of lipogenesis in 3T3-L1 adipose cells (22.2% of that in differentiated control cells). In conclusion, these results suggest that Vietnam Robusta coffee beans solid-state fermented with MP mycelium are amenable to industrial applications as a functional coffee beverage or material.

Analysis of Antioxidant Activity and Serotonin Derivatives in Safflower (Carthamus tinctorius L.) Germplasm Collected from Five Countries (국외 수집 홍화 유전자원의 항산화 활성 및 세로토닌 유도체 함량 분석)

  • Jung, Yi Jin;Assefa, Awraris Derbie;Lee, Jae Eun;Lee, Ho Sun;Rhee, Ju Hee;Sung, Jung Sook
    • 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.

Physicochemical Properties and Protective Effects of Corni fructus Treated with Pressurized-Steam against H2O2-Induced Cytotoxicity on L132 Cells (가압증숙공정에 의한 산수유의 이화학적 특성 및 과산화수소에 의해 유도된 산화적 L132 세포 사멸에 대한 보호 효과)

  • Park, Hye-Mi;Hong, Joo-Heon
    • Journal of the Korean Society of Food Science and Nutrition
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    • v.46 no.9
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    • pp.1061-1070
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    • 2017
  • This study examined the physicochemical properties and protective effects of Corni fructus treated with pressurized-steam (through $121^{\circ}C$, $1.2kgf/cm^2$, 0.5 h, 1 h, 2 h, and 3 h) against $H_2O_2$-induced cytotoxicity on L132 cells. The color values of the untreated Corni fructus powder were higher than those of Corni fructus after the pressurized-steam treatment (PSC), and those of PSC improved with a decrease in treatment time. At the observation by pressurized-steam treatment for more than 2 h, the color was changed to black, and its gloss was lost. The major constituents in PSC (2 hours) were the total sugar (468.53 mg/g), reducing sugar (385.55 mg/g), and total phenol (37.32 mg/g), respectively. The main components in the free sugars of PSC (2 h) were fructose, glucose, and sucrose, at 207.72 mg/g, 219.40 mg/g, and 4.31 mg/g, respectively. The gallic acid in the phenol compounds and 5-(hydroxymethyl) furfural in the furan compounds of PSC (2 h) improved with increasing treatment time. The main components in iridoid glycoside of PSC (2 h) were morroniside, loganin, and lognic acid, which improved with decreasing treatment time. The L132 cell growth inhibition activities of all the extracts were significantly higher than that of the control. The protective effects against the $H_2O_2$-induced cytotoxicity on L132 cells of PSC (2 h) was 102.82% (at $1,000{\mu}g/mL$) higher than those of the other extracts. This suggests that Corni fructus by PSC is useful for functional food materials in the food industry.

Metabolizing analysis according to the sawdust media of the known anticancer trees by Pleurotus ostreatuss (느타리버섯의 항암수목자원 배지속 함유성분의 분해능 평가)

  • Shin, Yu-Su;Yang, Bo-Hyun;Kang, Bo-Yeon;Kim, Hyun-Soo;Lee, Ji-Hyun;Hong, Yoon-Pyo;Lee, Sang-Won;Lee, Chan-Jung;Kim, Seung-Yoo
    • Journal of Mushroom
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    • v.9 no.4
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    • pp.186-189
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    • 2011
  • The transitivity of Chemical constituents by Pleurotus ostreatus cultivated in different raw sawdusts, which are Juglans mandchurica, Cudrania tricuspidata and Lindera glauca, was investigated. The HPLC chromatography patterns on the chemical constituents of P. ostreatus showed the similar chromatography patterns in all different raw sawdusts and control sawdust. The unknown chemical constituents of P. ostreatus cultivated in the 10%, 20% mixed medium added 10 %, 20% different raw sawdusts, respectively, were increased. But the significance results in the mixed medium added 50% different raw sawdusts were not showed. The chromatography patterns of mycelia grown in media added the 80% MeOH extracts of three tree species showed the similar patterns in comparison with control mycelia. In the results, the secondary metabolites of functional media were not degrade and changed to other derivatives compounds by P. ostreatus.

Surface Modification Using Spiropyran-Derivative and Its Analysis of Surface Potential Induced by UV (스파이로파이란에 의한 표면 개질 및 자외선에 의해 유도된 표면 전위에 대한 분석)

  • Lee, Bong-Soo;Han, Dong-Keun;Son, Tae-Il;Jung, Young-Hwan
    • Journal of the Korean Chemical Society
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    • v.55 no.3
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    • pp.478-485
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    • 2011
  • Merocyanine derivatives transformed from spiropyran-containing compounds by irradiating the light of ultraviolet (UV) include zwitterion of phenolate anion and amine cation. Complexation of this phenolate anion on merocyaninemodified surface and Ni ion among metal ions led to a change of surface charge and it was measured with kelvin prove force microscopy (KFM). We found that the resultant surface potential decreased linearly as UV-exposed time increased, and finally were saturated. Also it was analyzed through XPS the immobilized amount of Ni ions was increased according to increase of UV-exposed time. It is considered that these properties could be applied for detection and a quantitative control of different metal ions. Further research is to aim construct specific scaffold/matrix which enable high selective, high sensitive and, especially, a quantitative immobilization of metal ions-binding biomaterials such as proteins and cells.