• Title/Summary/Keyword: 화합물 생성

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Inhibitory Effect of Active Compounds Isolated from Impatiens balsamina(Garden Balsam) for Melanogenesis (봉선화 내에 함유 된 레톡시나프타퀴논의 미백활성에 미치는 영향)

  • Roh, Seok-Seon;Hwang, Dong-Sung
    • Journal of Haehwa Medicine
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    • v.21 no.1
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    • pp.125-133
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    • 2012
  • 본 논문은 피부미백에 관한 실험적 연구로서, 봉선화(Impatiens balsamina Linne)의 성분 중에서 하이드록시-나프타-퀴논(hydroxynaphthoquinone)이 멜라닌 생성억제 효능, 색소침착 저해 효과 등의 미백 활성이 있는 것으로 밝혀졌다. 피부흑화(melanogenesis)는 멜라닌 색소생성세포(melanocyte)에서 자외선 등의 자극에 대한 방어기작으로 멜라닌 생성 활동이 증가되고 이로 말미암아 만들어진 다량의 멜라닌이 각질형성세포(keratinocyte)로 전이되어 피부 표피층에 축척된 결과이다. 비록 멜라닌이 피부에 보호작용을 하나 피부의 과색소 침착은 기미, 주근깨, 피부염증 후의 피부흑화, 노인성 색소반점 등을 일으키며 이로 인해 피부미용 상의 불편뿐만 아니라 정신적으로 부정적인 영향을 미쳐 사회활동에 불편을 초래하기도 한다. 멜라닌 생성 과정은 아미노산의 일종인 티로신(tyrosine)에 티로시나제(tyrosinase)라는 효소가 작용하여 도파(DOPA), 도파퀴논(dopaquinone)으로 바뀐 후 비효소적인 산화 반응을 거쳐 만들어 지며, 이것이 피부 내에 이상 침착하여 기미, 검버섯 등이 생기는 것이라고 알려져 있다. 이와 같은 색소침착, 기미, 반점 등의 완화, 예방 및 치료에는 멜라닌 생성을 억제하는 물질, 예를 들면 하이드로퀴논(hydroquinone), 알부틴, 비타민 C 및 그 유도체 등이 개발되어 사용되고 있으나 이 중, 하이드로퀴논은 일단 효과가 인정되고 있지만 감작성이 있기 때문에 일반적으로 사용이 제한되고 있다. 아스콜빈산은 쉽게 산화되어, 이를 배합한 제품에는 변색, 변취가 되는 문제를 야기하고, 식물추출물 유래의 물질들은 식물의 산지에 따라 효능의 차이가 심하여 제품의 균질성이 유지되기 어렵다. 이러한 이유로 많은 멜라닌 생성을 억제하는 물질을 개발하기 위한 연구들이 계속 진행하고 있다. 2-히드록시-[1,4]나프토퀴논 유도체는 다음과 같은 구조를 나타낸다. 상기 구조에서 R은 포화 혹은 불포화된 직쇄 또는 분지쇄의 알킬로서, 바람직하게는 C1 내지 C10의 포화 혹은 불포화된 직쇄 또는 분지쇄의 알킬이고, 보다 바람직하게는 C1 내지 C5의 포화 혹은 불포화된 직쇄 또는 분지쇄의 알킬이다. 실험에 활용된 화합물은 다음과 같은 반응식으로 얻어졌다. 2-히드록시-[1,4]나프토퀴논과 포타슘카보네이트(K2CO3)를 아세토니트릴에 용해한 후, 저온수조로 냉각하고 알킬할라이드를 적당한 당량비로 천천히 적하하여 히드록시기와 에테르(ether) 반응을 통하여 얻어질 수 있다. 상기 반응식에서 R은 C1~10의 포화 또는 불포화된 알킬기로서 직쇄형 또는 분지쇄형 모두 가능하다. 상기 화합물인 2-히드록시-[1,4]나프토퀴논(2-hydroxynaphthoquinone)은 배양된 쥐의 멜라노마 세포에 대하여 하이드로퀴논과 대등한 멜라닌 생성 억제효과를 보였다. 하이드로퀴논은 저농도에서 강력한 멜라닌 생성 억제효과를 보이지만 상기 화합물들은 보다 낮은 농도에서도 세포독성을 나타내지 않으며 하이드로퀴논보다 높은 멜라닌 생성 억제 효과를 보였다.

Anti-melanogenesis Active Constituents from the Extracts of Carpinus turczaninowii Leaves (소사나무 잎 추출물 유래 멜라닌합성 저해 활성 성분)

  • Kang, Ji Mi;Kim, Jung Eun;Lee, Nam Ho
    • Journal of the Society of Cosmetic Scientists of Korea
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    • v.43 no.1
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    • pp.35-41
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    • 2017
  • Melanin synthesis inhibition activities were investigated for the extracts prepared from the leaves of Carpinus turczaninowii (C. turczaninowii) by using B16F10 melanoma cells. As a result, the ethanol extract ($100{\mu}g/mL$) showed 72.2% inhibition activities without cell toxicities in MTT assays. For the solvent fractions (n-hexane, ethyl acetate, n-butanol, water), the most potent activities were observed at the ethyl acetate fraction. To isolate the active constituents, the ethyl acetate fraction was further purified to afford four compounds; ethyl gallate (1), quercetin rhamnose (2), kaempferol rhamnose (3) and quercetin galloylrhamnose (4). The identification of the isolates was made by spectroscopic data including NMR spectra, and all of the compounds 1-4 were isolated for the first time from the leaves of C. turczaninowii. Anti-melanogenesis activities were studied for the isolates 1-4, and the compound 4 was determined to decrease the melanin synthesis dose-dependently without causing cell toxicities. ELISA measurement indicated that the isolate 4 decreased the contents of cell tyrosinase, a critical enzyme in melanogenesis. Based on these results, the extracts of C. turczaninowii were found to be applicable as whitening ingredients in cosmetic formulations.

Thermal Degradation Characteristics of Carbon Tetrachloride in Excess Hydrogen Atmosphere (과잉수소 반응조건하에서 사염화탄소의 고온 분해반응 특성 연구)

  • Won, Yang-Soo;Jun, Kwan-Soo;Choi, Seong-Pil
    • Journal of Environmental Science International
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    • v.5 no.5
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    • pp.569-577
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    • 1996
  • pure compound chloromethanes; methyl chloride, methylene chloride, chloroform and The carbon tetrachloride were used as a model of chlorocarbon system with Cl/H ratio to investigate thermal stability and hydrodechlorination process of carbon tetrachloride under excess hydrogen atmosphere. The parent thermal stability on basis of temperature required for 99% destruction at 1 second no was evaluated as $875^{\circ}C$ for $CH_3Cl$, $780^{\circ}C$ for $CH_2Cl_2$, $675^{\circ}C$ for $CHCl_3$ and $635^{\circ}C$ for $CCl_4$. Chloroform was thermally less stable than $CCl_4$ at fairly low temperatures $(<570^{\circ}C).$ The lion of $CCl_4$ became more sensitive to increasing temperature, and $CCl_4$ was degraded CHCl3 at above $570^{\circ}C.$ The number and quantity of chlorinated products decreases with increasing temperature for the Product distribution of $CCl_4$ decomposition reaction system. Formation of non-chlorinated hydrocarbons such as $CH_4$, $C_2H_4$ and C_2H_6$ increased as the temperature rise and particularly small amount of methyl chloride was observed above $850^{\circ}C$ in $CC1_4$/$H_2$ reaction system. The less chlorinated products are more stable, with methyl chloride the most stable chlorocarbon in this reaction system.

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Modulatory Effect of Four Azulene Derivatives from the Fruiting Bodies of Lactarius hatsudake on Interferon-$\gamma$ Production (젖버섯아재비 자실체로부터 분리한 Azulene계 화합물이 Interferon-$\gamma$ 생성에 미치는 영향)

  • Xu, Guang Hua;Kim, Jae-Wha;Li, Gao;Yoo, Ick-Dong
    • Journal of the Society of Cosmetic Scientists of Korea
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    • v.36 no.2
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    • pp.151-156
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    • 2010
  • Investigation of secondary bioactive metabolites from the fruiting bodies of Lactarius hatsudake led to the isolation of four azulene derivatives by means of repeated column chromatography and preparative HPLC, and they were identified as 1-formyl-4-methyl-7-isopropyl azulene (1), lactaroviolin (2), 4-methyl-7-isopropyl-azulene-1-carboxylic acid (3), and 1-formyl-4-methyl-7-(1-hydroxy-1-methylethyl) azulene (4) by their physico-chemical properties and spectroscopic analysis. The isolated compounds were evaluated for the effects on modulation of cytokines in natural killer cell line (NK92 cells). Compounds 1 and 4 strongly inhibited IFN-$\gamma$ production in a dose-dependent manner, corresponding to 101.3 % and 92.7 % inhibition at 400 ${\mu}M$, and 11.9 % and 24.1 % at 100 ${\mu}M$, respectively, whereas compounds 2 and 3 showed weak inhibitory effect on INF-$\gamma$ production, corresponding to 45.9 % and 18.0 % inhibition at 400 ${\mu}M$.

Stereochemistry of the Degradation Product of (-)-α-Narcotine and Its Analogs with Ethyl Chloroformate ((-)-α-Narcotine과 유사화합물을 ethyl chloroformate로 반응시 생성된 분해물의 입체화학)

  • Lee Dong-Ung
    • Journal of Life Science
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    • v.15 no.1 s.68
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    • pp.147-151
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    • 2005
  • A$(-)-\alpha$-narcotine from Papaver sommiferum was refluxed with ethyl chloroformate to give the diastereomeric chloro-carbamate mixture and the Z/E-enol lactones as Z:E=1:1.1 ratio in HPLC analysis. After photoisomerization with UV (254 nm), the Z/E ratio was drastically changed to Z:E=7:1, which may indicate that the E-isomer was easily converted to the Z-isomer due to photoisomerization. The photoisomerization of the Z/E-enol lactones and the different stereochemistry of the degradation product of $\beta-narcotine$, deuterated $\beta-narcotine$ and $\beta-narcotine$ with ethyl chloroformate will also be discussed.

Palladium Catalyzed Synthesis of Aryl Conjugated Enamides (팔라듐 촉매를 이용한 Aryl Conjugated Enamides의 합성)

  • Young Taik Hong;Jong Tae Lee;Cheol Mo Ryu;Kim, Jin Il
    • Journal of the Korean Chemical Society
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    • v.29 no.3
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    • pp.287-294
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    • 1985
  • Acrylamide, N-alkyl substituted acrylamides and N,N-diethylacrylamide were reacted with aryl bromides in the presence of triethylamine and palladium acetate-triorthotolyl phosphine catalyst to form the various substituted aryl conjugated enamides. These reactions proceeded selectively and (E)-isomer of aryl conjugated enamides was obtained. N-alkyl substituted acrylamides were more reactive than acrylamide or N,N-diethylacrylamide and gave high yields of vinylated products. Aryl bromides with electron withdrawing group showed good reactivity but aryl bromides with electron donating group showed poor reactivity or no reactivity for acrylamide or N,N-diethylacrylamide.

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Characterization of Bio-oils Produced by Fluidized Bed Type Fast Pyrolysis of Woody Biomass (목질바이오매스의 급속열분해에 의해 생산된 바이오오일의 특성 분석)

  • Choi, Joon-Weon;Choi, Don-Ha;Cho, Tae-Su;Meier, Dietrich
    • 한국신재생에너지학회:학술대회논문집
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    • 2006.06a
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    • pp.474-477
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    • 2006
  • 유동형 급속열분해기((fluidized bed type fast pyrolyzer, 용량 300g/h)를 이용하여 너도밤나무와 침엽수 흔합재(독일가문비나무/전나무, 50:50)로부터 바이오오일을 생산하였다. 목질바이오매스의 열분해는 약 $470{\pm}5^{\circ}C$에서 1-2초 간 진행되었다. 목질바이오매스의 열분해 생성물의 조성을 살펴보면, 너도밤나무는 바이오오일이 약 60%, 탄이 약 9% 피리 고 가스가 31% 가량 생산되었으며, 침엽수 혼합재는 49%의 바이오오일, 9%의 탄, 그리고 42% 가량의 가스가 생성되었다. 두 종류의 목질바이오매스에서 생산된 바이오오일에는 약 17-22% 가량의 수분이 포함되어 있었으며, 비중은 약 1.2kg/L 이었다. 바이오오일의 원소 조성은 탄소가 45%, 산소가 47% 수소가 7%, 그리 고 질소가 1% 로서 일반적 인 목질바이오매스와 큰 차이는 없는 것으로 나타났다. 그러나 화석자원에서 생산되는 오일류와 비교하여 산소함량은 매우 높았으나 황은 전혀 포함하고 있지 않았다. 바이오오일의 GC분석 결과 총 90여종의 고리형, 또는 비고리형 저분자량 화합물이 검출되었으며 이들의 함량은 바이오오일 전건중량의 31-33% 정도로 측정되었다.

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Characteristics of Thiosulfinates and Volatile Sulfur Compounds from Blanched Garlic Reacted with Alliinase (Alliinase 첨가에 의한 열처리 마늘로부터 생성된 함황 화합물의 특성)

  • Choi, Yoon-Hee;Shim, You-Sin;Kim, Cheong-Tae;Lee, Chan;Shin, Dong-Bin
    • Korean Journal of Food Science and Technology
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    • v.39 no.6
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    • pp.600-607
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    • 2007
  • In this study, attempts were made to develop a method for controlling the volatile sulfur compounds in garlic. Crude alliinase extracted from fresh garlic was applied to garlic pulp blanched far 5 min at $100^{\circ}C$, and the changes in the thiosulfinates and volatile compounds of the blanched garlic pulp reacted with the enzyme were investigated. Eight kinds of thiosulfinates from garlic were separated by HPLC, and identified by LC/MS/MS. When the alliinase was added to the blanched garlic pulp at 100, 200, 300, or 400 units, and reacted for 15 min, respectively, thiosulfinates were generated in the amounts of 37, 68, 77, and 80% of the fresh garlic content (control). Under the same conditions, we analyzed the volatile compounds, where 28 peaks were identified by GC/MSD. Of the 28 peaks, 23 were volatile sulfur compounds. The results of the analysis showed that all the volatile compounds were generated at amounts of 25, 36, 66, and 76% of the content of the control, respectively. These results indicate that the sulfur compound content of garlic can be regulated, depending upon the reaction conditions of allinase.

Anti-inflammatory and Anti-bacterial Constituents from the Extracts of Daucus carota var. sativa Aerial Parts (당근 지상부 추출물 유래 항염 및 항균 활성 성분)

  • Kim, Jung Eun;Jo, Yeon Jeong;Lee, Nam Ho
    • Journal of the Society of Cosmetic Scientists of Korea
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    • v.44 no.4
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    • pp.427-436
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    • 2018
  • In this study, we investigated anti-inflammatory and anti-bacterial constituents from Daucus carota var. sativa (carrot) areal parts. For the extract and solvent fractions, the anti-inflammatory activities were examined by measuring the nitric oxide (NO) production using LPS-stimulated RAW 264.7 cells. Among them, the ethyl acetate (EtOAc) fraction decreased the NO level in a dose-dependent manner. To elucidate further anti-inflammatory mechanisms, EtOAc fraction was evaluated by estimating their effects on the production of prostaglandin $E_2$ and pro-inflammatory cytokines as well as on the expression of inducible nitric oxide synthase (iNOS) and cyclooxygenase-2 (COX-2). As a result, the EtOAc fraction was determined to inhibit the production of $PGE_2$, IL-$1{\beta}$, IL-6 and reduce the iNOS, COX-2 protein expression. Upon the anti-bacterial tests using Staphylococcus epidermidis and Propionibacterium acnes, n-hexane (Hex) and EtOAc fractions showed the most potent activities. Three phytochemicals were isolated form the EtOAc fraction; diosmetin (1), diosmin (2), cynaroside (3). The chemical structures of the isolated compounds were elucidated based on the spectroscopic data including $^1H$ and $^{13}C$ NMR spectra, as well as comparison of the data to the literatures. Anti-inflammatory and anti-bacterial effects were studied for the isolates. All of the compounds (1 - 3) decreased the NO production, effectively. Also, compound 3 showed anti-bacterial activity on P. acnes. Based on these results, D. carota var. sativa extract could be potentially applicable as anti-inflammatory and anti-bacterial ingredients in cosmetic formulations.

Stenotrophomons maltophilia에 의한 방향족 화합물의 생분해

  • 최창석;박진희;김영식;이태진
    • Proceedings of the Korean Society of Soil and Groundwater Environment Conference
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    • 2002.09a
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    • pp.71-74
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    • 2002
  • 다고리방향족 탄화수소를 페놀에 적응된 미생물을 이용하여 분해하고자 하였다. 분리된 Stenotrophomons maltophilia는 나프탈렌과 페난스렌을 탄소원 및 에너지원으로 이용하였으며 10mg/$\ell$의 나프탈렌과 0.9mg/$\ell$의 페난스렌이 완전히 분해되는데 지체기후 약 2일과 3일이 소요되었다. 나프탈렌, 페난스렌의 분해시 중간생성물로 chromatography 상에 새로운 피크들이 생성되었으며, 이러한 중간생성물을 파악하여 다고리 방향족 탄화수소의 분해경로를 모색하고자 하였다.

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