• Title/Summary/Keyword: $\beta$-Lactone

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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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    • v.24 no.1
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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.

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

  • Lee, Jung Hwan;Ko, Jae Young;Seo, Kyung Jae;Goo, Yang Mo;Lee, Youn Young
    • Journal of the Korean Chemical Society
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    • v.43 no.4
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    • pp.447-455
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    • 1999
  • Allyl (5R)-(Z)- and (5R)-(E)-6-[(2S)-2,3-isopropylidenedioxypropylidene]Penicillanate(10a and 10b) were prepared from allyl (5R)-dibromopenicillanate(6) via a sequence of reactions involving condensation with 2,3-O-isopropylidene-D-glyceraldehyde, reduction with $Zn-NH_4OAc$, and Mitsunobu elimination. Deprotection of isopropylidene and allyl groups of 10a gave potassium (5R)-(Z)-6-[(2S)-2,3-dihydroxypropylidene]penicillanate(4). However, deprotection of isopropylidene group of 10b afforded ${\alpha},\;{\beta}$-unsaturated-lactone(12). Allyl (5R)-(Z)- and (5R)-(E)-6-[(2S)-2-(t-butyldimethlsilyloxy)propylidene]penicillanate(18a and 18b) were prepared from ally (5R)-dibromopenicillanate(6) via a sequence of reactions involving condensation with (2S)-2-(t-butyldimethylsilyloxy)propanal(15), reduction with $Zn-NH_4OAc$ and Mitsunobu elimination or mesylation-elimination. Deprotection of t-butyldimethylsilyl and allyl groups of 18a and 18b gave potassium (5R)-(Z)- and (5R)-(E)-6-[(2S)-2-hydroxypropylidene]penicillanate(5a and 5b), respectively.

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

  • Yang, Chul-Hak;Lee, Hee-Yong
    • Clinical and Experimental Reproductive Medicine
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    • v.10 no.2
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    • pp.1-11
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    • 1983
  • ${\beta}$-Glucuronidase from bull seminal plasma was partially purified by $(NH_4)_2SO_4$fractionation, two successive DEAE-cellulose columns, isoelectric focusing (pH 4 to 6) and Gel filtration on Sephadex G-200. Only one form of ${\beta}$-glucuronidase was obtained by isoelectric focusing at pH 5.13. Highly purified ${\beta}$-glucuronidase had specific activity of 34 units/mg protein and showed one major and some minor contaminants by disc gelk electrophoresis. The enzyme showed maximum activity at pH 5.2 and at $48^{\circ}C$. The enzyme was completely inhibited by 1,4 saccharo-${\alpha}$-lactone (5 mM). Albumin and 0.15 M NaCl increased the ${\beta}$-glucuronidase activity. Km of ${\beta}$-glucuronidase using phenolphthalein mono-${\beta}$-glucuronic acid as substrate was 2.9 mM and Vmax was $0.8{\mu}$mole/min. The enzyme appeared to be a glycoprotein by its binding to concanvalin·A. Rabbit and human sperm-acrosomal extracts and seminal plasma showed high ${\beta}$-glucuronidase activity.

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Biodegradation of Aromatic Compounds by Nocardioform Actinomycetes

  • CHA CHANG-JUN;CERNIGLIA CARL E.
    • Proceedings of the Microbiological Society of Korea Conference
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    • 2001.11a
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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

  • Lee, A-Neum;Park, Se-Jeong;Yun, Sae-Mi;Lee, Mi-Young;Son, Bu-Soon;Youn, Hyung-Sun
    • Biomedical Science Letters
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    • v.16 no.1
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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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    • v.12 no.4
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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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    • v.38 no.9
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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.

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

  • Kim, So-Mi;Chung, Tae-Young
    • Applied Biological Chemistry
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    • v.39 no.5
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    • pp.389-397
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    • 1996
  • The volatile concentrate obtained from the edible Korean dureup plant (Aralia elata Seem.) by a distillation-extraction system was separated into hydrocarbon and oxygen-containing fractions, and the latter was further separated into nine subfractions by silica gel column chromatography. Gas chromatography (GC) and gas chromatography/mass spectrometry (GC/MS) were utilized to identify 167 volatile compounds in the fractions. The volatile compounds included 72 hydrocarbons, 31 alcohols, 23 aldehydes, 16 esters, 10 acids, 6 ketons, 3 furans, 2 phenols, 1 indole, 1 oxide, 1 sulfide, and 1 lactone. ${\beta}-Caryopyllene$, a sesquiterpene hydrocarbon, was the most abundant volatile compound identified in Korean dureup (19.53%). Dureup oil was found to possess a woody or herbaceous aroma following sensory evaluation of each fraction and individual volatile component using a GC-sniff apparatus.

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

  • Yun, Mi-Sun;Yeon, Bo-Ram;Cho, Hae-Me;Lee, Sa-Eun;Jhoo, Jin-Woo;Jung, Ji-Wook;Park, Yu-Hwa;Kim, Song-Mun
    • Korean Journal of Weed Science
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    • v.32 no.3
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    • pp.195-203
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    • 2012
  • The essential oil was extracted by steam distillation from the aerial part of erect bur-marigold (Bidens tripartita L.), one of the noxious weed in paddy field. The composition of the essential oil was analyzed by gas chromatography-mass spectrometry. The fragrance of the essential oil was green, herbal, oily, spicy. There were 42 constituents in the essential oil:17 hydrocarbons, 6 alcohols, 6 acetates, 5 N-containing compounds, 3 ethers, 3 ketones, 1 lactone and 1 S-containing compound. Major constituents were ${\alpha}$-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%), and ${\beta}$-cubebene (5.27%). The $IC_{50}$ value in MTT assay using HaCaT keratinocyte cell line was 0.018%. However, attachment of patch with 0.1% of the erect bur-marigold essential oil for 24 hr did not show any skin toxicity. Overall results of this study suggest that the essential oil of erect bur-marigold could be used as a source for the development of perfumery industrial products.

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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    • v.30 no.4
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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.