• 제목/요약/키워드: $\beta$-Lactone

검색결과 54건 처리시간 0.03초

Characterization of an Antibiotic Produced by Bacillus subtilis JW-1 that Suppresses Ralstonia solanacearum

  • Kwon, Jae Won;Kim, Shin Duk
    • Journal of Microbiology and Biotechnology
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    • 제24권1호
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    • pp.13-18
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    • 2014
  • Bacillus subtilis JW-1 was isolated from rhizosphere soil as a potential biocontrol agent of bacterial wilt caused by Ralstonia solanacearum. Seed treatment followed by a soil drench application with this strain resulted in >80% reduction in bacterial wilt disease compared with that in the untreated control under greenhouse conditions. The antibacterial compound produced by strain JW-1 was purified by bioactivity-guided fractionation. Based on mass spectroscopy and nuclear magnetic resonance spectral data ($^1H$, $^{13}C$, $^1H-^1H$ correlation spectroscopies, rotating frame nuclear Overhauser effect spectroscopy, and heteronuclear multiple-bond correlation spectroscopy), the structure of this compound was elucidated as a cyclic lipopeptide composed of a heptapeptide (Gln-Leu-Leu-Val-Asp-Leu-Leu) bonded to a ${\beta}$-hydroxy-iso-hexadecanoic acid arranged in a lactone ring system.

6-히드록시알킬리덴페니실란산 염의 합성 (Synthesis of 6-Hydroxyalkylidenepenicillanates)

  • 이중환;고재영;서경재;구양모;이윤영
    • 대한화학회지
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    • 제43권4호
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    • pp.447-455
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    • 1999
  • Allyl (5R)-dibromopenicillanate(6)의 2,3-O-isopropylidene-D-glyceraldehyde와의 축합, $Zn-NH_4OAc$에 의한 환원 및 Mitsunobu 제거반응의 일련의 과정을 거처서 allyl (5R)-(Z) 및 (5R)-(E)-6-[(2S)-2,3-isopropylidenedioxypropylidene]penicillanate(10a 및 10b)를 합성하였다. 화합물10a의 이소프로필리덴 및 알릴 보호기를 제거하여 potassium (5R)-(Z)-6-[(2S)-2,3-dihydroxypropylidene]penicilla-nate(4)를 얻었다. 그러나 화합물 10b의 이소프로필리덴 보호기를 제거한 결과 ${\alpha},\;{\beta}$-unsaturated-lactone(12)이 얻어짐을 확인하였다. Allyl(5R)-6,6-dibromopenicillanate(6)의 (2S)-2-(t-butyldimethyl-silyloxy)propanal(15)과의 축합, $Zn-NH_4OAc$에 의한 환원 및 Mitsunobu 제거반응 또는 메실화-제거반응의 일련의 과정을 거처서 allyl (5R)-(Z)- 및 (5R)-(E)-6-[(2S)-2-(t-butyldimethylsilyloxy)propylidene]-penicillanate(18a 및 18b)를 합성하였다. 화합물 18a 및 18b의 t-부틸디메틸실릴 및 알릴 보호기를 제거하여 potassium (5R)-(Z)- 및 (5R)-(E)-6-[(2S)-2-hydroxypropylidene]penillanate(5a 및 5b)를 얻었다.

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황소의 정액에서 베타-굴룩 유로니다아제의 정제 및 그 성질에 관한 연구 (STUDY OF ${\beta}$-GLUCURONIDASE FROM SULL SEMINAL PLASMA:PURIFICATION AND PROPERTIES)

  • 양철학;이희영
    • Clinical and Experimental Reproductive Medicine
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    • 제10권2호
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    • pp.1-11
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    • 1983
  • 황소의 정액에서 베타 굴룩유로니다아제를 부분적으로 정제하였다. 이 정제과정에는 $(NH_4)_2SO_4$ 의 분획분리법, 두개의 연속적인 DEAE-셀루로오즈 콜럼 및 등전초점화법(pH4-6) 및 세파덱스 G-200의 절여과 방법이 쓰여졌다. 등전초점화(lsoelectric focusing)법을 사용했을때 pH5.13에서 베타 굴룩유로니다아제는 한 형태의 단백질로 존재하였다. 고도로 정제된 베타 굴룩유로니다아제는 전기영동법에 의해 한개의 주된 띠와 약간의 불순물의 띠로 나타났고 특수활동도는 34Units/mg 단백질로 나타났다. 이 효소는 pH 5.2 와 $48^{\circ}C$ 에서 가장 높은 활동도를 나타냈다. 알부민이나 0.15M 소금용액에서 베타 굴룩유로니다아제는 활동도가 상승됐다. 페놀프타레인-모노-베타-굴룩 유로닉산을 기질로 사용했을때 km값은 2.9mM 이었고 Vmax값은 $0.8{\mu}$mole/min 이었다. 대두의 콘카나발린 A에 흡착하는 것으로 보아 이 효소는 당단백질임이 확인됐다. 토끼, 사람의 정자 아크롬좀 추출물 및 정액에서 이 효소는 높은 활성도를 나타냈다.

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Biodegradation of Aromatic Compounds by Nocardioform Actinomycetes

  • CHA CHANG-JUN;CERNIGLIA CARL E.
    • 한국미생물학회:학술대회논문집
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    • 한국미생물학회 2001년도 추계학술대회
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    • pp.157-163
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    • 2001
  • Mycolic acid-containing gram-positive bacteria, so called nocardioform actinomycetes, have become a great interest to environmental microbiologists due to their metabolic versatility, multidegradative capacity and potential for bioremediation of priority pollutants. For example, Rhodococcus rhodochrous N75 was able to metabolize 4-methy1catechol via a modified $\beta$-ketoadipate pathway whereby 4-methylmuconolactone methyl isomerase catalyzes the conversion of 4-methylmuconolactone to 3-methylmuconolactone in order to circumvent the accumulation of the 'dead-end' metabolite, 4-methylmuconolactone. R. rhodochrous N75 has also shown the ability to transform a range of alkyl-substituted catechols to the corresponding muconolactones. A novel 3-methylmuconolactone-CoAsynthetase was found to be involved in the degradation of 3-methylmuconolactone, which is not mediated in a manner analogous to the classical $\beta$-ketoadipate pathway but activated by the addition of CoA prior to hydrolysis of lactone ring, suggesting that the degradative pathway for methylaromatic compounds by gram-positive bacteria diverges from that of proteobacteria. Mycobacterium sp. Strain PYR-l isolated from oil-contaminated soil was capable of mineralizing various polyaromatic hydrocarbons (PAHs), such as naphthalene, phenanthrene, pyrene, fluoranthrene, 1-nitropyrene, and 6-nitrochrysene. The pathways for degradation of PAHs by this organism have been elucidated through the isolation and characterization of chemical intermediates. 2-D gel electrophoresis of PAH-induced proteins enabled the cloning of the dioxygenase system containing a dehydrogenase, the dioxygenase small ($\beta$)-subunit, and the dioxygenase large ($\alpha$)-subunit. Phylogenetic analysis showed that the large a subunit did not cluster with most of the known sequences except for three newly described a subunits of dioxygenases from Rhodococcus spp. and Nocardioides spp. 2-D gel analysis also showed that catalase-peroxidase, which was induced with pyrene, plays a role in the PAH metabolism. The survival and performance of these bacteria raised the possibility that they can be excellent candidates for bioremediation purposes.

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Parthenolide Suppresses the Expression of Cyclooxygenase-2 and Inducible Nitric Oxide Synthase Induced by Toll-Like Receptor 2 and 4 Agonists

  • ;;;;;윤형선
    • 대한의생명과학회지
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    • 제16권1호
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    • pp.39-45
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    • 2010
  • Toll-like receptors (TLRs), which are pattern recognition receptors (PRRs), recognize pathogen-associated molecular patterns (PAMPs) and regulate the activation of innate immunity. All TLR signaling pathways culminate in the activation of NF-${\kappa}B$, leading to the induction of inflammatory gene products such as cyclooxygenase-2 (COX-2) and inducible nitric oxide synthase (iNOS). Parthenolide, a sesquiterpene lactone isolated from the herb feverfew (Tanacetum parthenium), has been used as folk remedies to treat many chronic diseases for many years. In the present report, we present biochemical evidence that parthenolide inhibits the NF-${\kappa}B$ activation induced by TLR agonists and the overexpression of downstream signaling components of TLRs, MyD88, $IKK{\beta}$, and p65. Parthenolide also inhibits TLR agonists-induced COX-2 and iNOS expression. These results suggest that parthenolide can modulate the immune responses regulated by TLR signaling pathways.

Biological Characterization of the Chemical Structures of Naturally Occurring Substances with Cytotoxicity

  • Park, Hee-Juhn;Jung, Hyun-Ju;Lee, Kyung-Tae;Choi, Jong-Won
    • Natural Product Sciences
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    • 제12권4호
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    • pp.175-192
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    • 2006
  • Screening for the cytotoxicity from plant origin is the first stage for anti-cancer drug development. A variety of terpenoids with exomethylene, epoxide, allyl, $\alpha,\beta-unsaturated$ carbonyl, acetylenes, and $\alpha-methylene-\gamma-lactone$ induces apoptosis and/or differentiation as well as cytotoxicity through the ROS signal transduction pathways. These are found among monoterpenes, sesquiterpenes, triterpenes, flavonoids, coumarins, diarylheptanoids, and even organosulfuric compounds. The most essential characteristics of natural cytotoxic substances is to possess the strong electrophilicity that is susceptible to nucleophilic biomolecules in the cell. Thiol-reductants and superoxide dismutase can block or delay apoptosis. Thus, ROS and the resulting cellular redox-potential changes can be parts of the signal transduction pathway during apoptosis. Disturbance of the balance of oxireduction by the pigment of natural quinones also caused the induction of the differentiation and apoptosis. Saponins with the cytotoxicity are restricted to their monodesmosides, rather than to bisdesmosides. Those saponins exhibited calcium ion-mediated apoptosis in addition to cytotoxicity whereas they showed also differentiation without extracellular calcium ion. The properties on cytotoxicity, apoptosis, and differentiation were assumed to depend on resultant oxidative stress to the cells. In this review, we describe a spectrum of cytotoxic compounds with various action mechanisms.

The Genome-Wide Expression Profile of Saussurea lappa Extract on House Dust Mite-Induced Atopic Dermatitis in Nc/Nga Mice

  • Lim, Hye-Sun;Ha, Hyekyung;Shin, Hyeun-Kyoo;Jeong, Soo-Jin
    • Molecules and Cells
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    • 제38권9호
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    • pp.765-772
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    • 2015
  • Saussurea lappa has been reported to possess anti-atopic properties. In this study, we have confirmed the S. lappa's anti-atopic properties in Nc/Nga mice and investigated the candidate gene related with its properties using microarray. We determined the target gene using real time PCR in in vitro experiment. S. lappa showed the significant reduction in atoptic dermatitis (AD) score and immunoglobulin E compared with the AD induced Nc/Nga mice. In the results of microarray using back skin obtained from animals, we found that S. lappa's properties are closely associated with cytokine-cytokine receptor interaction and the JAK-STAT signaling pathway. Consistent with the microarray data, real-time RT-PCR confirmed these modulation at the mRNA level in skin tissues from S. lappa-treated mice. Among these genes, PI3Kca and $IL20R{\beta}$ were significantly downregulated by S. lappa treatment in Nc/Nga mouse model. In in vitro experiment using HaCaT cells, we found that the S. lappa components, including alantolactone, caryophyllene, costic acid, costunolide and dehydrocostus lactone significantly decreased the expression of PI3Kca but not $IL20R{\beta}$ in vitro. Therefore, our study suggests that PI3Kca-related signaling is closely related with the protective effects of S. lappa against the development of atopic-dermatitis.

두릅의 휘발성 향기성분에 관한 연구 (Volatile Compounds Isolated from Edible Korean Fatsia Shoots (Aralia elata Seem.))

  • 김소미;정태영
    • Applied Biological Chemistry
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    • 제39권5호
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    • pp.389-397
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    • 1996
  • 연속수증기증류장치를 이용하여 두릅으로부터 얻어진 휘발성농축물은 탄화수소구분 및 함산소구분으로 분리되었고, 함산소구분은 실리카겔 관 크로마토그래피에 의해서 9개의 계대구분으로 다시 분획하였다. 기체크로마토그래피와 기체크로마토그래피에 질량분석계를 연결시킨 장치는 휘발성성분을 동정하기 위하여 사용하였다. 동정된 167개의 휘발성성분은 72개의 탄화수소, 31개의 알콜, 23개의 알데히드, 16개의 에스테르, 10개의 산, 6개의 케톤, 3개의 푸론, 2개의 페놀, 1개의 인돌, 1개의 산화물, 1개의 설파이드 및 1개의 락톤이었다. Sesquiterpene 탄화수소인 ${\beta}-caryopyllene$은 두릅에서 동정된 휘발성 성분중에서 함량이 가장 높았으며, 19.53%를 차지하였다. 두릅정유는 관능검사용 기체크로마토그래피를 사용하여 각 구분에 함유된 개별 휘발성성분을 평가에 의해서 초목 모양의 향기를 함유하고 있음이 밝혀졌다.

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가막사리 (Bidens tripartita L.) 정유의 향취, 화학성분 및 세포독성 (Fragrance, Chemical Composition and Toxicity of the Essential Oil in Erect Bur-marigold (Bidens tripartita L.))

  • 윤미선;연보람;조해미;이사은;주진우;정지욱;박유화;김성문
    • 한국잡초학회지
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    • 제32권3호
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    • pp.195-203
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    • 2012
  • 가막사리는 우리나라 전역의 논에서 다발생하여 농업에 막대한 피해를 주는 일년생잡초이지만 이를 활용하는 방안에 대해서는 연구된 바가 없다. 본 연구의 목적은 가막사리 정유를 향장산업제품의 소재로 활용할 수 있는지를 구명하는데 있다. 가막사리에 함유된 정유의 함량은 $0.028{\pm}0.003%$이었으며, 역치값은 0.1%이었으며, 향취는 green, herbal, oily, spicy이었다. 가막사리 정유에는 탄화수소 17종, 알코올 6종, 아세테이트 6종, 질소화합물 5종, 에테르 3종, 케톤 3종, 락톤 1종, 황화합물 1종 등 총 42종의 화학성분이 함유되어 있었으며, 다함량 성분은 ${\alpha}$-phellandrene(22.50%), ${\alpha}$-pinene(22.21%), 2,4-dimethyl(2,5-dimethylphenyl)methyl ester benzoic acid(15.11%), limonene(10.66%), ${\beta}$-pinene(35.43%), ${\beta}$-cubebene(5.27%)이었다. 가막사리 정유가 HaCaT 각질형성세포에 미치는 세포독성을 조사하기 위한 MTT assay를 실시한 결과, 가막사리 정유의 $IC_{50}$값은 0.018%이었으며, 피부에 미치는 영향을 조사하기 위하여 피부자극유발시험을 수행한 결과 가막사리 정유 0.1% 처리에도 그 어떠한 발진이나 수포도 발견되지 않았다. 본 연구의 결과는 가막사리 정유가 향장제품을 위한 소재로 활용될 수 있다는 점을 시사하여 준다.

Elucidation of the Biosynthetic Pathway of Vitamin B Groups and Potential Secondary Metabolite Gene Clusters Via Genome Analysis of a Marine Bacterium Pseudoruegeria sp. M32A2M

  • Cho, Sang-Hyeok;Lee, Eunju;Ko, So-Ra;Jin, Sangrak;Song, Yoseb;Ahn, Chi-Yong;Oh, Hee-Mock;Cho, Byung-Kwan;Cho, Suhyung
    • Journal of Microbiology and Biotechnology
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    • 제30권4호
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    • pp.505-514
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    • 2020
  • The symbiotic nature of the relationship between algae and marine bacteria is well-studied among the complex microbial interactions. The mutual profit between algae and bacteria occurs via nutrient and vitamin exchange. It is necessary to analyze the genome sequence of a bacterium to predict its symbiotic relationships. In this study, the genome of a marine bacterium, Pseudoruegeria sp. M32A2M, isolated from the south-eastern isles (GeoJe-Do) of South Korea, was sequenced and analyzed. A draft genome (91 scaffolds) of 5.5 Mb with a DNA G+C content of 62.4% was obtained. In total, 5,101 features were identified from gene annotation, and 4,927 genes were assigned to functional proteins. We also identified transcription core proteins, RNA polymerase subunits, and sigma factors. In addition, full flagella-related gene clusters involving the flagellar body, motor, regulator, and other accessory compartments were detected even though the genus Pseudoruegeria is known to comprise non-motile bacteria. Examination of annotated KEGG pathways revealed that Pseudoruegeria sp. M32A2M has the metabolic pathways for all seven vitamin Bs, including thiamin (vitamin B1), biotin (vitamin B7), and cobalamin (vitamin B12), which are necessary for symbiosis with vitamin B auxotroph algae. We also identified gene clusters for seven secondary metabolites including ectoine, homoserine lactone, beta-lactone, terpene, lasso peptide, bacteriocin, and non-ribosomal proteins.