• 약학회지
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• 제48권2호
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• pp.135-140
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• 2004

For the development of new COX-2 inhibitors, 1,5-diarylhydantoins 5a∼5c and 1,5-diaryl-2-thiohydantoin 6a∼6c were synthesized from commercially available phenylacetic acids through esterification, bromination, C-N bond formation and cyclization. Esters 2a∼c were efficiently synthesized from the starting materials 1a∼c by refluxing in absolute methanol for 3 hours with catalytic concentrated sulfuric acid. Bromination of 2a∼c was carried out with use of N-bomosuccinimide at rt in dichloromethane. The bromine of 3a∼c was substituted with aniline in ethanol or N,N-dimethylformamide to provide 4a∼c. Hydantoins and 2-thiohydantoins were synthesized from 4a∼c by treatment of potassium isocyanate or potassium thiocyanate in dil-ethanol with triethylamine.

• Bulletin of the Korean Chemical Society
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• 제28권5호
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• pp.751-757
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• 2007

To develop new COX-2 inhibitors, 1,5-diarylhydantoins and 1,5-diaryl-2-thiohydantoins were synthesized from phenylacetic acids by esterification, bromination, C-N bond formation and cyclization. Esters 1-3 were efficiently synthesized from the starting materials by reflux in absolute methanol for 3 h containing concentrated sulfuric acid as catalyst. Bromination was carried out with N-bromosuccinimide at rt in dichloromethane. Bromides 4-6 were reacted with aniline, p-anisidine, sulfanilamide in ethanol (or N,N-dimethylformamide) to provide the amines 7-15. Hydantoins and 2-thiohydantoins 16-46 were synthesized from amines 7-15 by treating them with potassium isocyanate (or potassium thiocyanate) and triethylamine. The synthetic process from alkyl α-anilinophenylacetate 7-15 to 3-alkylhydantoins was carried out in a one-pot reaction using alkyl isocyanate (alkyl isothiocyanate).

• 한국임상약학회지
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• 제16권1호
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• pp.52-56
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• 2006

Aceclofenac, a nonsteroidal antiinflammatory agent of a phenylacetic acid type, has been used for rheumatoid arthritis and osteoarthrits. Although the metabolic pathway of aceclofenc is relatively well-known in vitro, pharmacokinetic profiles of its three major or metabolites are still unclear in human. The present study was designed to investigate pharmacokinetic profiles of the metabolites of aceclofenac, and to evaluate the bioequivalence of the generic preparation of aceclofenac 100 mg tablet. Blood samples were serially collected for a period of 12 hours following a single oral administration of 100 mg aceclofenac in 20 healthy human volunteers. A simple protein precipitation with acetonitrile was employed to purify those substances from plasma. Aceclofenac, diclofenac, 4'-hydroxyaceclofenac and 4'-hydroxy-diclofenac in heparinized plasma were simultaneously measured with flufenamic acid, an internal standard, using HPLC coupled to a tandem mass spectrometer. Time courses of 4'-hydroxydiclofenac, diclofenac and aceclofenac plasma concentrations were clearly revealed, and the pharmacokinetic properties were analyzed. The 90% confidence intervals for the ratios of test/reference for log-transformed AUC and $C_{max}$ lie within 0.80-1.25.

• The Plant Pathology Journal
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• 제29권2호
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• pp.174-181
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• 2013

The plant growth-promoting rhizobacterium Ochrobactrum lupini KUDC1013 elicited induced systemic resistance (ISR) in tobacco against soft rot disease caused by Pectobacterium carotovorum subsp. carotovorum. We investigated of its factors involved in ISR elicitation. To characterize the ISR determinants, KUDC1013 cell suspension, heat-treated cells, supernatant from a culture medium, crude bacterial lipopolysaccharide (LPS) and flagella were tested for their ISR activities. Both LPS and flagella from KUDC1013 were effective in ISR elicitation. Crude cell free supernatant elicited ISR and factors with the highest ISR activity were retained in the n-butanol fraction. Analysis of the ISR-active fraction revealed the metabolites, phenylacetic acid (PAA), 1-hexadecene and linoleic acid (LA), as elicitors of ISR. Treatment of tobacco with these compounds significantly decreased the soft rot disease symptoms. This is the first report on the ISR determinants by plant growth-promoting rhizobacteria (PGPR) KUDC1013 and identifying PAA, 1-hexadecene and LA as ISR-related compounds. This study shows that KUDC1013 has a great potential as biological control agent because of its multiple factors involved in induction of systemic resistance against phytopathogens.

• 대한한의학회지
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• 제24권3호
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• pp.23-34
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• 2003

Objective : In 2001, the rate of obesity in Korea reached 30.6%. There are many therapeutic ways to reduce body weight, such as low and very low calorie diet, exercise therapy, behavior modification therapy, etc. However, in many cases the patients feel stress under obesity treatment because of starvation. This study was aimed to evaluate the anti-starvation stress effect of Coicis Semen on mice. Methods : First, the mice were divided into 6 groups : Normal (group with no starvation), Control (administrated normal saline 6 times before starting 36 hours starvation), and Samples A, B, C, and D (administrated 0.25, 0.5, 1.0, 3.0 g/kg Coicis Semen respectively 6 times before starting 36 hours starvation). Then the plasma corticosterone level and rectal temperature were measured. The norepinephrine, dopamine, DOPAC (dihydroxy-phenylacetic acid), 5-HT (5-hydroxytryptamine) and 5- HIAA (5-hydroxy-indole-acetic acid) in the hypothalamus were measured by the HPLC method. Result : I. The rectal temperature in Sample group D showed a significant difference (P<0.05) compared with the Control group. 2. The DOPAC in Sample groups A, C and D showed the significant difference (P<0.05) compared with the Control group. Conclusion : It might be recognized that Coicis Semen has an anti-starvation stress effect.

• Archives of Pharmacal Research
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• 제21권1호
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• pp.17-23
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• 1998

Flavonoid glycosides were metabolized to phenolic acids via aglycones by human intestinal microflora producing ${\alpha}$-rhamnosidase, exo-${\beta}$-glucosidase, endo- ${\beta}$-glucosidase and/or ${\beta}$-glucuronidase. Rutin, hesperidin, naringin and poncirin were transformed to their aglycones by the bacteria producing ${\alpha}$-rhamnosidase and ${\beta}$-glucosidase or endo- ${\beta}$-glucosidase, and baicatin, puerarin and daidzin were transformed to their aglycones by the bacteria producing ${\beta}$glucuronidase, C-glycosidase and ${\beta}$-glycosidase, respectively. Anti-platelet activity and cytotoxicity of the metabolites of flavonoid glycosides by human intestinal bacteria were more effective than those of the parental compounds. 3,4-Dihydroxyphenylacetic acid and 4-hydroxyl-phenylacetic acid were more effective than rutin and quercetin on anti-platelet aggregation activity. 2,4,6-Trihydroxybenzaidehyde, quercetin and ponciretin were more effective than rutin and ponciretin on the cytotoxicity for tumor cell lines. We insist that these flavonoid glycosides should be natural prodrugs.

• 한국연초학회지
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• 제25권2호
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• pp.144-153
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• 2003

This study was carried out to determine the relationship between smoke components and sensory evaluation by changes tobacco leaf blending. Seven different cigarettes were made by adding different types of oriental, reconstituted and expanded tobacco leaves. 62 kinds of smoke components which were 6 of general components, 34 of semi-volatile and volatile components, 9 of acid components, and 13 of phenolic components were analyzed. Eight kinds of sensory item were evaluated and also electronic nose system data was collected. All smoke components and sensory characteristics of mainstream smoke were changed by the different blending. To determine the relationship between smoke components and sensory test, the correlation and regression analysis were carried out by using SPSS statistical program. Tar, pH, and CO showed a high correlation with sensory evaluation item. As tar related to hotness, CO have a high correlation with offensive aroma. Semi-volatile and volatile components of smoke related to sensory characteristics such as aroma, taste, irritation, hotness and smoothness. When propylene, l,3-butadiene, butane, isoprene, and 2-methylfuran showed a high correlation with aroma; methyl chloride, methanol, toluene, ethyl benzene showed a high correlation with irritation. Some acidic components and phenolic components of smoke also had a high relation to smoke volume. Especially the acidic components such as 2-furoic acid, 2-hydroxybutyric acid, phenylacetic acid and palmitic acid; the phenolic components such as 4-vinyl phenol, pyrocatechol, 3-methyl catechol, hydroquinone showed a high correlation with smoke volume. As using regression analysis, it was possible to estimate the results of sensory evaluation from the smoke analysis data. From the results of electronic nose system analysis, we can find the different pattern by adding expanded tobacco leaf.

• 약학회지
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• 제18권1호
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• pp.59-73
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• 1974

Fifteen derivatives of phthalide were synthesized from m-hemipinic, hydrastic and 4,5-benzophthalic anhydride with acetic, phenylacetic, p-methoxyphenylacetic, p-nitrophenylacetic, ${\alpha}$-nephthylacetic and succinic acid by the Gabriel condensation. In the same way, 13 derivatives of phthalimidine and 4 derivatives of ${\alpha,\beta}$ -benzisothiazoline-1, 1-dioxide were synthesized from diphenylmaleimide, phthalimide, saccharine and 4,5-benzo-phthalimide with previous 6 acids. 3-Substituted derivatives of m-hemipinic anhydride, hydrastic anhydride and 4,5-benzophthalic anhydride were treated with formamide and seven 3-substituted imidines could be synthesized. In case of 4,5-benzophtha lide, two isomers,4,5-benzophthalidene-3-acetic acid and 4,5-benzophthalidene-1-acetic acid, can be obtained theoretically, but only one product we got, and the chemical structure of it was identified by the following way. It was hydrolyzed and then decarboxylated, and this decomposed product was identical with 1-acetyl-2-naphthoic acid which was synthesized from .betha.-naphthylamine. This indicates that by the Gabriel condensatioin 4,5-benzophthalide only produces 4,5-benzophthlidene-3-acetic acid, that is ${\alpha}$-carbonyl substitute.

• The Korean Journal of Ecology
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• 제24권3호
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• pp.125-130
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• 2001

본 연구는 토끼풀 추출액이 잔디의 발아와 생장에 미치는 allelopathy효과를 살펴보기 위해 실시되었다. 토끼풀을 잎, 줄기, 뿌리, 꽃으로 나누어 추출한 후 실험한 잔디종자의 상대 발아율은 꽃, 잎, 줄기, 뿌리의 순으로 억제되었고 75% 이상의 농도에서는 전 실험구에서 발아가 되지 않았다. 파종후 5일, 8일, 11일, 14일의 신장율과 생중량을 조사해본 결과 고농도로 갈수록 억제되었고 길이생장에 있어서 지상부보다 지하부의 생장을 더욱 저해하였으며 상대생중량은 뿌리, 줄기, 잎, 꽃의 순으로 나타났다. 토끼풀 추출액 중 phenolic compounds를 Gas chromatography에 의해 성분분석 한 결과 부위별로 차이가 있었으나 caffeic acid, p-hydroxybenzoic acid, ferulic acid, gallic acid, p-coumaric acid, vanillic acid, trans-cinnamic acid, 2,5-dihydroxybenzoic acid, syringic acid, 2-hydroxycinnamic acid, benzoic acid, salicylic acid, phloroglucinol, phenylacetic acid 등 14종류의 성분을 확인하였고, 이들 중 phloroglucinol, vanillic acid, 2-hydroxycinnamic acid, syringic acid를 제외한 10종류를 공통으로 함유하고 있는 것으로 분석되었다. 분석결과 동정된 14종류의 phenolic compounds에 의한 발아와 생장실험 결과 전체적으로 억제효과를 나타내었으며, 고농도로 갈수록 심화되었고 benzoic acid, salicylic acid, trans -cinnamic acid에서 매우 강한 억제효과를 나타내었다.

• 대한약리학회지
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• 제28권1호
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• pp.11-18
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• 1992

Physostigmine을 급성(0.75 mg/kg), 7일간 매일 1회(0.75 mg/kg) 그리고 7일간 연속(0.15 mg/kg/h) 투여한 쥐의 선조체에 있어서 dopamine(DA) 및 대사체와 tyrosine hydroxylase(TH)활성도의 변화를 검색하였다. 급성 투여 1시간 후 선조체의 DA 농도는 변화가 없었으나 dihydroxy-phenylacetic acid(DOPAC)과 homovanillic acid(HVA)농도는 증가하였다. 또한 DA의 turnover의 증가를 제시하는 DOPAC/DA와 HVA/DA의 비율도 증가하였다. 그러나 TH활성도는 24시간 후 감소를 나타내었다. Physostigmine을 매일 및 연속 투여군에서는 DA과 대사체의 농도에는 변화가 없었으나, DA의 turnover의 감소를 제시하는 DA과 대사체의 비율은 감소하였다. 그러나 TH활성도는 매일 투여군에서만 감소를 나타내었다. 이러한 결과는 physostigmine을 급성 및 아급성으로 투여시 dopamine대사의 변화가 있음을 제시한다. 또한 콜린 신경계의 아급성 자극은 dopamine 대사 및 활성도를 감소 시킬 가능성을 시사해 주었다.