• 제목/요약/키워드: Alpha Hydroxy Acid

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Synthesis and Anticonvulsant Evaluations of N-Cbz-$\alpha$-amino-N- alkoxyglutarimides

  • Kim, Min-Jeong;Byun, Ae-Sun;Choi, Jong-Won;Moon, Kyung-Ho;Lee, Chung-Kyu;Park, Min-Soo
    • Archives of Pharmacal Research
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    • 제27권2호
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    • pp.151-155
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    • 2004
  • In our previous studies for the development of new anticonvulsant of broad spectrum, we found that N-cbz-$\alpha$-aminoglutarimides showed significant anticonvulsant activities of broad spectrum enough to be recommended for the new anticonvulsants and their anticonvulsant activities were dependent on their imide substituent groups. Based on these results, various N-cbz--$\alpha$-amino-N-alkoxyglutarimides, where the imide N-H was substituted with the hydroxy and alkoxy group, were prepared and evaluated for their anticonvulsant activities using the Maximal electroshock seizure (MES) and Pentylenetetrazole induced seizure (PTZ) tests and also the rotorod test. A series of (R) or (S)-N-cbz--$\alpha$-amino-N-alkoxyglutarimides could be prepared from the corresponding (R) or (S)-N-cbz-glutamic acid following the usual synthetic procedure. Among them, (R)-N-cbz--$\alpha$-amino-N-hydroxyglutarimide ($ED_{50}$=86.25 mg/kg) was most active in the MES test. In the case of the PTZ test, (R)-N-cbz--$\alpha$-amino-N-benzyloxyglutarimide ($ED_{50}$= 62.5 mg/kg) was most active. Among the tested compounds, 2a-c, 3a, and 3b showed anticonvulsant activities in the MES and PTZ test. All of the tested compounds, except 2f and 3f, showed significant anticonvulsant activities in the MES or PTZ test. In addition, the neurotoxicities of these compounds were comparable to other anticonvulsant drugs.

Isolation and Structural Determination of Free Radical Scavenging Compounds from Korean Fermented Red Pepper Paste (Kochujang)

  • Chung, Jin-Ho;Shin, Heung-Chule;Cho, Jeong-Yong;Kang, Seong-Koo;Lee, Hyoung-Jae;Shin, Soo-Cheol;Park, Keun-Hyung;Moon, Jae-Hak
    • Food Science and Biotechnology
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    • 제18권2호
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    • pp.463-470
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    • 2009
  • Sixteen antioxidative active compounds isolated from the EtOAc layer of MeOH extracts of kochujang, Korean fermented red pepper paste, were structurally elucidated as fumaric acid, methyl succinate, succinic acid furan-2-yl ester methyl ester (gochujangate, a novel compound), 2-hydroxy-3-phenylpropanoic acid, 3,4-dihydroxybenzoic acid, 2,3-dihydroxybenzoic acid, 2,4-dihydroxybenzoic acid, 6,7-dihydroxy-2H-chromen-2-one (esculetin), caffeic acid, cis-p-coumaric acid, trans-p-coumaric acid, daidzin, genistin, apigenin 7-O-$\beta$-D-apiofuranosyl($1{\rightarrow}2$)-$\beta$-D-glucopyranoside, apigenin 7-O-$\beta$-Dglucopyranoside, and quercetin 3-O-$\alpha$-L-rhamnopyranoside by mass spectrometry (MS) and nuclear magnetic resonance (NMR) experiments. These compounds were analyzed for the first time as antioxidants from kochujang.

감잎의 성장시기별 향기성분의 변화 (Changes of Flavor Compounds in Persimmon Leaves(Diospyros kaki folium) during Growth)

  • 김종국;강우원;김귀영;문혜경
    • 동아시아식생활학회지
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    • 제11권6호
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    • pp.472-478
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    • 2001
  • 감잎의 성장시기별 일반성분과 감잎차의 주요한 품질 특성인 향기성분을 연속수증기증류추출법(SDE) 으로 추출하여 GC-MS에 의하여 분리 동정하여 감잎차를 제조하기 위한 감잎의 최적 채취시기를 조사하였다. 감잎에서의 향기성분은 alcohol류 23종, aldehyde류 18종, ester류 4종, acid류 15종, hydrocarbon류 37종. ketone류 14종, phenol류 6종 및 기타 9종 등 126종의 휘발성 향기성분이 동정되었다. 감잎의 주요 향기성분 중 alcohol류는 linalool. cis-3-hexanal, 1-$\alpha$-terpineol, 3,7,11,15-tetramethyl-2-hexadecen-1-ol이며. aldehyde류는 trans-2-hexanal, nonanal. 2-decenal이며 acid류는 hexanoic acid, nonanoic acid, palmitic acid이며, hydrocarbon류는 1.1-dimethylethyl cyclohexane, 1-methyl-4- [ (2 methylpropyl) ] -benzene이며, ketone류는 2-hydroxy-3-propyl-2-cyclopenten-1-one이며, phenol류는 2.6is(1,1-dimethylethyl)-4-methyl phenol이었다. 감잎의 향기성분은 감잎이 성장함에 따라 그 종류 및 상대적인 함량이 증가하였으며 6월 중순 이후에는 감소하였고 7월 초순에는 현저한 감소를 나타내었다. 감잎의 성장시기에 따른 유효성분의 함량은 향기성분과 병행하여 조사한 결과 감잎이 성장함에 따라 증가하다가 6월 20일 이후에는 감소하였는데 감잎차의 제조를 위한 채취시기는 유용성분과 향기성분의 상대적인 함량이 높은 6월 중순경이 가장 적합할 것으로 생각된다.

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Chemical Constituents from the Hydrangea chinensis

  • Khalil, Ashraf-Taha;Chang, Fang-Rong;Lee, Yue-Han;Chen, Chung-Yi;Liaw, Chih-Chuang;Patnam Ramesh;Shyng Shiou F.Yuan;Wu, Yang-Chang
    • Archives of Pharmacal Research
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    • 제26권1호
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    • pp.15-20
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    • 2003
  • Two quinazolone alkaloids, (+)-febrifugine (1) and isofebrifugine (2), along with three coumarin derivatives, 6-hydroxy coumarin (3), skimmin (5), and $umbelliferone-7-O-{\alpha}-L-rhamnopyranosyl(1{\rightarrow}4)-{\beta}-D-glucopyranoside$ (6), were isolated from the roots of Hydrangea chinensis. Compound 6 is a new compound. In addition, umbelliferone (4), linoleic acid (7), two steroidal glycosides (8, 9), three furfural derivatives (10-12), and butyl-$\beta$-D-fructofuranoside (13) were isolated from the leaves of the same plant. The structures of all isolates were elucidated by spectral methods.

AMPA 수용체의 조절이 지니는 정신과적 의의 (Psychiatric Implication for the Regulation of AMPA Receptor)

  • 오대영;이은이
    • 생물정신의학
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    • 제20권1호
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    • pp.1-5
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    • 2013
  • Glutamate receptors are important components of synaptic transmission in the nervous system. Especially, ${\alpha}$-amino-3-hydroxy-5-methyl-4-isoxazole propionic acid (AMPA) receptors mediate most abundant excitatory synaptic transmission in the brain. There is elaborate mechanism of regulation of AMPA receptors including protein synthesis/degradation, intracellular trafficking, exocytosis/endocytosis and protein modification. In recent studies, it is revealed that functional dysregulation of AMPA receptors are related to major psychiatric disorders. In this review, we describe the structure and function of AMPA receptors in the synapse. We will introduce three steps of mechanism involving trafficking of AMPA receptors to neuronal membrane, lateral diffusion into synapses and synaptic retention by membrane proteins and postsynaptic scaffold proteins. Lastly, we will describe recent studies showing that regulation of AMPA receptors is important pathophysiological mechanism in psychiatric disorders.

Molecular Analysis of Freeze-Tolerance Enhanced by Treatment of Trinexapac-Ethyl in Kentucky Bluegrass

  • Hwang, Cheol Ho
    • 한국작물학회지
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    • 제44권2호
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    • pp.176-179
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    • 1999
  • Trinexapac-ethyl[ 4-(cyclopropyl- $\alpha$ -hydroxy-methylene)-3,5-dioxocyclohexane carboxylic acid ethylester] is a growth-retardant for plants by inhibiting a key step in biosynthesis of GA. A treatment of trinexapacethyl generally induces a reduction in vegetative growth and also inhibits heading. In addition, the trinexapacethyl was known to enhance the freeze-tolerance in annual bluegrass, however, the mechanism is not known yet. One possible reason for the enhanced freeze-tolerance may be the antifreeze protein known to be accumulated in intercellular space of the leaf during cold acclimation. In order to see the possible in-duction of the synthesis of antifreeze proteins by trinexacpacethyl, the apoplastic proteins extracted from Kentucky bluegrass treated with trinexapacethyl were analyzed by SDS-PAGE and the presence of the antifreeze protein was observed. In addition, western analysis showed the identity of the protein induced by both a cold acclimation and a trinexapacethyl treatment. It appears that an enhanced freeze-tolerance of the turf grass by trinexapacethyl is due to the synthesis and/or accumulation of the antifreeze protein similar to the enhanced freeze tolerance induced by cold acclimation.

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해동피성분(海桐皮成分)에 관(關)한 연구(硏究) ( II ) - Hederine의 분리(分離)및 동정(同定)에 대(對)하여 - (Studies on the Constituents of Kalopanax Pictum Nakai var Typicum Nakai ( II ) - Isolation and Identification of Hederine-)

  • 김학성;박재영
    • Journal of Pharmaceutical Investigation
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    • 제5권1호
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    • pp.23-27
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    • 1975
  • Hederine, m. p. $256{\sim}257^{\circ}\;C_{41}H_{64}O_{11}\;{\cdot}\;2H_{2}O$ : $23-hydroxy-3{\beta}-({\beta}-{\alpha}-arabinosidor hamnoside)-olenana-12-ene-oique,$ was obtained from the cortex of Kalopanax pictum. Acid hydrolysis of hederine yielded hederagenin, arabinose and rhamnose. Hederagenin was identified by comparison of it's mixed melting point and IR spectra against authentic sample. Arabinose and rhamnose were identified by TLC against standards.

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TRIMETHYLGLYCINE: A VEGETAL STRESS-MOLECULE PERFORMING A WIDE RANGE OF COSMETIC ACTIVITY

  • L. Rigano;K. Jutila
    • 대한화장품학회:학술대회논문집
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    • 대한화장품학회 2003년도 IFSCC Conference Proceeding Book II
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    • pp.192-199
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    • 2003
  • Trimethylglycine, commonly named betaine, is the most simple amphoteric molecule. It is completely vegetal (1,2), as it is produced in the sugar industry by industrial chromatography of molasses. While abundantly used in foods and diet supplements, many interesting applications in cosmetics have recently been investigated, like its capability to increase the volume and stability of foams in surfactant solutions. For its special chemical structure (it is the internal salt of a weak acid and a strong alkali) trimethylglycine is a solvent and buffering agent for strong acids and Lewis' acids. It allows to improve the efficiency of $\alpha$- and $\beta$-hydroxy acids in increasing the physiological rate of epidermal cell renewal, while keeping a low skin-irritation level. In oral care cosmetics, it acts as a mucous membrane protectant (3). For its special water co-ordination capability, its solubilising power, polymer swelling capability, after-feel improvement in hair products, skin moisturization and elasticity enhancing properties, trimethylglycine provides unusual characteristics to many products intended for skin maintenance (4).(omitted)

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Propylene Glycol 용매계에서 DL-Alanine과 D-Glucose의 마이야르 반응에 의한 휘발성 화합물의 생성 (Formation of Volatile Compounds from Maillard Reaction of D-Glucose with DL-Alanine in Propylene Glycol Solution)

  • 김영희;김옥찬;이정일;양광규
    • 한국식품과학회지
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    • 제20권2호
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    • pp.157-163
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    • 1988
  • Propylene glycol 용매계에서 0.5M DL-alanine(${\alpha}-amino-propionic acid$) 와 0.5M D-glucose 를 $100^{\circ}C,\;120^{\circ}C$$140^{\circ}C$에서 각각 20분, 2시간 반응시켜 생성되는 휘발성 화합물을 분석하고 반응온도와 시간이 갈색화반응 및 휘발성 화합물생성에 미치는 영향을 조사하였다. 갈색화반응 및 휘발성 화합물생성에 미치는 영향을 조사하였다. 갈색화반응은 반응온도와 시간이 증가함에 따라 급격히 증가 하였다. 휘발성 화합물은 7종의 alkylpyrazine, 4종의 pyrrole, 3종의 furan, 1종의 furanone 그리고 기타성분으로 2-hydroxy-3-methyl-2-cyclopenten-1-one을 포함하여 11종이 확인되었으며 pyrazine, pyrrole 및 furan화합물의 생성량은 반응온도가 높아지고 반응시간이 길어짐에 따라 급격히 증가하였다. 또한 alanine과 glucose의 마이야르 반응에 의해 생성되는 구수한 카라멜냄새 및 설탕 탄냄새(burnt sugar-like)는 주로 2-hydroxy-3-methyl-2-cyclopenten-1-one, 2, 5-dimethyl-4-hydroxy-3(2H)-furanone과 같은 함 산소화합물과 pyrazine, pyrrole과 같은 함 질소화합물에 의해 생성되는 것으로 추정되었다.

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삼불화메틸기가 포함된 디히드로-1,4-옥사티인 카르복스아닐리드 유도체의 합성과 살균 활성 (Synthesis of Trifluoromethylated Dihydro-1,4-oxathiin Carboxanilides and Their Fungicidal Activity)

  • 남기달;김진철;조광연;한호규
    • Applied Biological Chemistry
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    • 제44권3호
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    • pp.191-196
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    • 2001
  • 새로운 살균제 농약 개발을 목적으로 삼불화메틸기 디히드로-1,4-옥사티인기가 포함된 ${\alpha},{\beta}$-불포화 카르복스아미드 유도체 5를 합성하였다. 삼불화 ${\beta}$케토에스테르 유도체 6을 염화한 다음 1,2-메르캡토에탄을과 반응시켜 중간체 1,4-옥사티안 유도체 11을 얻었다. 중간체 11의 정제없이 히드록시기를 염소로 치환한 다음 중간체 10을거쳐 트리에틸 존재하에서 탈염화하여 삼불화메틸기가 포함된 디히드로-1,4-옥사티인 에틸에스테르 9를 합성하였다. 에스테르 9를 가수분해하여 생성된 카르복실산 12의 히드록시기를 염소로 치환하여 활성화한 다음 여러 가지 아민 유도체와 반응시켜 삼불화메틸기가 포함된 디히드로-1,4-옥사티인 카르복스아미드 유도체 5를 합성하였다. 합성된 화합물을 대표적인 6종의 식물병원균, 벼 도열병, 벼 잎집무의마름병, 오이 잿빛곰팡이병, 토마토 역병, 밀 붉은 녹병, 그리고 보리 흰가루병 등에 대한 in vivo 항균력을 시험하였다. 그 결과, 페닐기의 meta 위치에 이소프로폭시기 또는 이소프로필기가 치환된 화합물이 벼 잎집무의마름병과 밀 붉은녹병에 대한 강한 항균력을 나타냈다.

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