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Aspergillus candidus F1484 균주가 생산하는 항진균 화합물의 분리 및 특성
김성옥,이소영,김성규,손광희,김영국,문석식,복성해 한국미생물생명공학회 ( 구 한국산업미생물학회 ) 1996 한국미생물·생명공학회지 Vol.24 No.5
Candida albicans의 효모형태에 대해 활성을 나타내는 항진균 물질의 탐색 중에 Aspergillus candidus F1484 균주의 발효액으로부터 항진균 화합물 F1484를 단리하고 ethyl acetate 추출, silica gel column chromatography, ODS column chromatography 및 preparative HPLC를 행하여 분리정제하였다. F1484 화합물은 EI-MS, ^13C-, ^1H-NMR, DEPT, HMQC 및 HMBC에 의한 구조분석을 행한 결과 이 화합물은 항진균 물질인 chloroflavonin과 동일한 구조를 나타내었으며 효모형태의 Candida albicans에 대한 항진균 활성뿐만 아니라 여러 종류의 인체 종양 세포주에 대해서도 세포독성을 나타내었다. In the course of screening for the antifungal compounds against Candida albicans, an antifungal compound (F1480) was isolated from the culture broth of Aspergillus candidus F1484. Isolation and purification of compound F1484 were performed using ethyl acetate extraction, silica gel column chromatography, ODS column chromatography, and preparative HPLC. The structure of compound F1484 was determined by the spectroscopic analyses of EI-MS, ^13C-, ^1H-NMR, DEPT, HMQC, and HMBC. This compound appeared to have a structure of antifungal agent, chloroflavonin. In addition to antifungal activities against the yeast phase of Candida species, compound F1484 showed cytotoxic effect against various human tumor cell lines.
Moon, Surk-Sik,Rahman, Md. Aziz Abdur,Manir, Md. Maniruzzaman,Ahamed, V.S. Jamal 대한약학회 2010 Archives of Pharmacal Research Vol.33 No.8
Bioassay-directed fractionation of a methanolic extract from the seeds of Draba nemorosa (Brassicaceae) led to isolation of a new flavonol glycoside, drabanemoroside (5, kaempferol 3-O-${\alpha}$-L-rhamnopyranosyl-(1${\rightarrow}$2)-${\alpha}$-L-arabinopyranose) along with four known flavonoid derivatives (1-4), four cardenolide glycosides (6-9). Kaempferol glycosides 2 and 5 showed strong cytotoxicity against human small lung cancer cell line A549 and melanoma SK-Mel-2 with an $IC_{50}$ of 0.5 ${\mu}g/mL$ and 1.9 ${\mu}g/mL$, respectively. Cardenolide glycosides 6-9 showed potent cyto-toxicity (A549) in the range of 0.01-0.032 ${\mu}g/mL$. Their structures were characterized based on spectroscopic data (2D NMR, HRTOFMS, IR, and UV) and comparison of literature values. The carbohydrate units were also confirmed by comparing the hydrolysate of 5 with authentic monosaccharides.
Tsaokoarylone, a Cytotoxic Diarylheptanoid from Amomum tsao-ko Fruits
Moon, Surk-Sik,Cho, Soon-Chang,Lee, Ji-Young Korean Chemical Society 2005 Bulletin of the Korean Chemical Society Vol.26 No.3
The crude methanol extract of the fruits of Amomum tsao-ko (Zingiberaceae) showed cytotoxic activity. Bioactivity-guided separation led to the isolation of a diarylheptanoid, tsaokoarylone [7-(4-hydroxy-3-methoxyphenyl)-1-(4-hydroxyphenyl)-hepta-4E,6E-dien-3-one] (2). 2 showed cytotoxicity at 4.9 and 11.4 $\mu$g/mL ($IC_{50}$) against human nonsmall cell lung cancer A549 and human melanoma SK-Mel-2, respectively, determined by SRB colorimetric method. During purification-(4-hydroxyphenyl)-4-hydroxyhexan-2-one (4) together with three known diarylheptanoids was also isolated. Their structures were determined from interpretation of spectroscopic data (IR, UV, MS, and NMR) and synthesis confirmed the structure of 2.
The Synthesis of Carbamoylsulfenyl Chloride and its Derivatives
문석식,오동영,Surk Sik Moon,Dong Young Oh Korean Chemical Society 1983 대한화학회지 Vol.27 No.2
N-Methylidene-2,6-diethylaniline (III)은 2,6-diethylaniline (II)과 과량의 paraformaldehyde와의 반응으로 만들었으며, 이 화합물 III에서 N=$CH_2$ 프로톤은 AB 스핀계를 나타냈다. 화합물 III과 chlorocarbonylsulfenyl chloride(IV)를 반응시켜서 N-(chloromethyl)-N-(2,6-diethylphenyl)-carbamoylsulfenyl chloride(V)를 합성하였다. 화합물 V와 여러 종류의 알콜을 반응시켜서 Alkyl N-(chloromethyl)-N-(2,6-diethylphenyl)-carbamoylsulfenate esters(VI ${\sim}$XVI)를 71{\sim}$95%의 수득률로 합성하였다. VI${\sim}$XVI은 서서히 분해되지만 S-O 결합이 S=O결합으로 변하지는 않았다. 과량의 알콜은 V의 2가 황과 N-chloromethyl기의 ${\alpha}$-탄소에 대해 친핵성 공격을 할 수 있었으며, 이렇게 하여 생긴 화합물 (XVII, XVIII)은 상당한 안정성을 가지고 있었다. N-Methylidene-2,6-diethylaniline (III) was prepared by the reaction of 2,6-diethylaniline (II) with an excess paraformaldehyde. The protons of N=$CH_2$in the compound III exhibited a second order NMR spectrum. The compound III reacted with bifunctional chlorocarbonylsulfenyl chloride(IV) to give N-(chloromethyl)-N-(2,6-diethylphenyl)-carbamoylsulfenyl chloride(V). The reaction of the compound V with various alcohols resulted in the formation of Alkyl N-(chloromethyl)-N-(2,6-diethylphenyl)-carbamoylsulfenate esters(VI${\sim}$XVI) in 71${\sim}$95% yields. The compound VI${\sim}$XVI decomposed gradually, but the thermal rearrangement of S-O bonding to S=O bonding was not found. The nucleophilic attack of an excess alcohol to the compound Ⅴ was made on both divalent sulfur and ${\alpha}$-carbon of N-chloromethyl group. The corresponding substituted products(XVII, XVIII) had considerable stability.
Lee, Jung Yeop,Moon, Surk Sik,Hwang, Byung Kook John Wiley Sons, Ltd. 2005 Pest management science Vol.61 No.8
<P>An antifungal substance active against Colletotrichum orbiculare (Berk & Mont) Arx was isolated from the methanol extracts of Asarum sieboldii (Miq) Maek rhizomes. High-resolution MS, NMR and UV spectral data confirmed that the antifungal substance is kakuol, 2-hydroxy-4,5-methylenedioxypropiophenone. Colletotrichum orbiculare was most sensitive to kakuol, with MIC of 10 µg ml<SUP>−1</SUP>. Kakuol also completely inhibited the mycelial growth of Botrytis cinerea Pers ex Fr and Cladosporium cucumerinum Ellis & Arthur at 50 µg ml<SUP>−1</SUP> and 30 µg ml<SUP>−1</SUP>, respectively. However, no antimicrobial activity was found against yeast and bacteria even at 100 µg ml<SUP>−1</SUP>. Kakuol exhibited a protective activity against the development of anthracnose disease on cucumber plants. The control efficacy of kakuol against the anthracnose disease was in general somewhat less than that of the commercial fungicide chlorothalonil. This is the first report to demonstrate in vitro and in vivo antifungal activity of kakuol against C orbiculare infection. Copyright © 2005 Society of Chemical Industry</P>
Antimicrobial Phenolic Derivatives from Dendranthema zawadskii var. latilobum Kitamura (Asteraceae)
Md. Aziz Abdur Rahman,Surk-Sik Moon 대한약학회 2007 Archives of Pharmacal Research Vol.30 No.11
A phytochemical study on the root of Dendranthema zawadskii var. latilobum Kitamura, using a series of silica gel column chromatography and reversed phase C-18 HPLC chromatography, led to the isolation of (1S, 2S)-1, 2, 3-trihydroxy-1-(3, 4-methylenedioxyphenyl)propane (1), 4- methoxycinnamic acid (2), acacetin (3) and caffeic acid methyl ester (4). The structures of these compounds were determined using spectroscopic analyses (UV, IR, HRTOFMS and NMR), with comparison of their spectral data with previously reported values. Compound 1 was isolated for the first time, with compounds 2 and 4 from this plant reported for the first time. The antibacterial and antifungal activities of the isolated compounds were measured using the disc diffusion method. Also, their cytotoxicities against the cancer cell lines, A549, B16F1 and SK-Mel-2, and brine shrimp lethalities were evaluated.
Antioxidant Polyphenol Glycosides from the Plant Draba nemorosa
Rahman, Md. Aziz Abdur,Moon, Surk-Sik Korean Chemical Society 2007 Bulletin of the Korean Chemical Society Vol.28 No.5
Bioassay-directed fractionation of Draba nemorosa led to the isolation of two new phenolic glycosides, 1-O- (sinapoyl)-glucitol (2) and 1,3-disinapoylgentiobiose (5) along with five known phenolic glycosides (1, 3, 4, 6, and 7). Their structures were characterized based on spectroscopic methods (2D NMR, HRTOFMS, IR, and UV). The isolated compounds showed antioxidant activities (IC50) in the range of 14-98 mM which were estimated by DPPH radical-scavenging assay.
Antimicrobial Phenolic Derivatives from Dendranthema zawadskii var. latilobum Kitamura (Asteraceae)
Rahman, Md. Aziz Abdur,Moon, Surk-Sik 대한약학회 2007 Archives of Pharmacal Research Vol.30 No.11
A phytochemical study on the root of Dendranthema zawadskii var. latilobum Kitamura, using a series of silica gel column chromatography and reversed phase C-18 HPLC chromatography, led to the isolation of (1S, 2S)-1, 2, 3-trihydroxy-1-(3, 4-methylenedioxyphenyl)propane (1), 4-methoxycinnamic acid (2), acacetin (3) and caffeic acid methyl ester (4). The structures of these compounds were determined using spectroscopic analyses (UV, IR, HRTOFMS and NMR), with comparison of their spectral data with previously reported values, Compound 1 was isolated for the first time, with compounds 2 and 4 from this plant reported for the first time. The antibacterial and antifungal activities of the isolated compounds were measured using the disc diffusion method. Also, their cytotoxicities against the cancer cell lines, A549, B16F1 and SK-Mel-2, and brine shrimp lethalities were evaluated.