• 제목/요약/키워드: benzoic acid derivatives

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폐광지역에서 분리한 quinoline 분해 세균인 Pseudomonas sp. NFQ-1의 특성연구 (Characterization of the Quinoline-Degrading Bacterium Pseudomonas sp. NFQ-1 Isolated from Dead Coal Pit Areas)

  • 윤경하;황선영;권오성;오계헌
    • KSBB Journal
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    • 제18권3호
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    • pp.174-179
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    • 2003
  • 폐광지역으로부터 quinoline (2,3-benzopyridine)을 유일한 탄소원, 질소원, 그리고 에너지원으로 이용하는 세균 NFQ-1을 농화 배양기법을 통하여 분리하였다. 분리된 세균은 그람음성의 간균으로서 BIOLOG 시험을 통하여 Pseudomonas nitroreducens로 동정되었으며, 본 연구에서는 Pseudomonas sp. NFQ-1으로 명명하였다. Quinoline의 분해는 호기적 조건하의 B-배지에서 Pseudomonas sp. NFQ-1를 이용하여 실시되었다. 균주 NFQ-1 세균은 2.5 mM quinoline을 9시간 이내 완전히 분해하였다. 배양기간 동안 quinoline 분해의 중간대사산물인 2-hydroxyquinoline이 일시적으로 생성되었다가 배양기간 후반부에 사라졌다. 배양의 초기 pH 8.0은 6.8로 감소하다가 배양이 진행됨에 따라 7.0이 되었다. 대상 기질로서 quinoline의 농도가 증가함에 따라 생장곡선에서 유도기가 길어졌으며, 고농도의 quinoline (>15 mM)은 주어진 조건에서 균주의 생장과 quinoline의 분해를 억제하였다. 부가 질소원으로 7.6 mM $(\textrm{NH}_{4})_{2}\textrm{SO}_{4}$의 첨가조건하에서 Pseudomonas sp. NFQ-1은 2-hydroxyquinoline, p-coumaric acid, benzoic acid, p-cresol, p-hydroxybenzoate, protocatechuic acid, catechol 등의 다양한 화합물을 이용할 수 있었으나 일부 화합물들 (예, 6-hydroxyquinoline, 8-hydroxyquinoline, coumarin, indoline, pyridine, lepidine, quinaldine, 4-bydroxycournarin, benzene, salicylic acid, phenol, phthalate)은 탄소원으로 이용되지 못하였다. euinoline의 분해경로를 규명하기 위하여 catechol dioxygenases의 specific activity를 결정하였다. 그 값은 catechol 1,2-dioxygenase에서 약 184.7 U/mg, 그리고 catechol 1,2-dioxygenase에서 약 33.19 U/mg이었다. 그 결과 균주 NFQ-1은 quinoline를 분해하기 위하여 주로 ortho-분해경로를, 그리고 부분적으로 meta-분해경로를 이용하는 것을 보여주었다.

Gallic Acid Inhibits STAT3 Phosphorylation and Alleviates DDS-induced Colitis via Regulating Cytokine Production

  • Jeong, Ji Hyun;Kim, Eun Yeong;Choi, Hee Jung;Chung, Tae Wook;Kim, Keuk Jun;Kim, So Yeon;Ha, Ki Tae
    • 동의생리병리학회지
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    • 제30권5호
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    • pp.338-346
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    • 2016
  • Signal transducer and activator of transcription 3 (STAT3) is associated with various human diseases, such as cancer, auto-immune disease, and intestinal inflammation. The limited and inadequate effect of standard approaches for treating inflammatory bowel disease (IBD) has prompted to develop alternative anti-colitis agents through inhibition of STAT3. Here, we show that gallic acid (GA), a 3,4,5-trihydroxybenzoic acid, markedly reduced phosphorylation of STAT3. Among the derivatives of benzoic acids, GA showed significant inhibition on STAT3 phosphorylation. In addition, GA ameliorated the dextran sodium sulfate (DSS)-induced acute colitis as determined by the measurement of symptomatic and histological indices. The suppression of DSS-induced acute colitis by GA treatment may be related to the regulation of cytokines and growth factors. Furthermore, GA inhibited phosphorylation of STAT3 in the colon tissue of DSS-treated mice. These findings may be useful in comprehending the molecular action of GA on STAT3 phosphorylation and provide novel insights into the potential application of GA in the treatment of STAT3-related inflammatory disease, such as IBD.

Synthesis and Properties of Oxygen-bridged Aromatic Polyesters Based on Isomeric Naphthalenediols

  • Park, E-Joon;Park, Bong-Ku;Kim, Jae-Hoon;Lee, Sang-Chul;David J. T. Hill
    • Macromolecular Research
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    • 제8권1호
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    • pp.12-18
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    • 2000
  • Six aromatic polyesters with ether-linkages were prepared from 4,4'-oxybis(benzoic acid) and naphthalenediol (ND) isomers which were 1,4-, 1,5-, 1,6-, 2,3-, 2,6- and 2,7-derivatives. The solution viscosity numbers ranged from 0.23 to 0.65 dL/g. The glass transition temperatures ranged from 142 to 179$\^{C}$. The initial decomposition temperatures were all above 400$\^{C}$, and the residue weights at 600$\^{C}$ were in the range of 50-64%. Only the polyesters derived from 1,5- and 2,6-NDs, which have a linear linking mode, were found to be semicrystalline and could form thermotropically nematic phase. Multiple melting phenomena and annealing of the polyester derived from 1,5-ND and related polymers are described. The experimental results show that the polyester derived from 1,4-ND of linear shape was amorphous and non-liquid crystalline. Particularly, the polyester derived from 2,3-ND could form a smectic mesophase as banana-shaped molecules, and this is ascribed to the C/sub_2v/ symmetry where highly kinked molecules are packed in the same direction.

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Development of a Single Chain Antibody Using a Phage Display Cloning Method for the Detection of 2,4-Dinitrotoluene

  • Na, Jung-Hyun;Joo, Man-Seok;Lee, Won-Kyu;Shim, Hyunbo;Lim, Si-Hyung;Jung, Sang Taek;Yu, Yeon Gyu
    • Bulletin of the Korean Chemical Society
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    • 제34권2호
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    • pp.460-464
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    • 2013
  • Single-chain variable fragments of antibodies (scFv) specific to 2,4-dinitrotoluene (DNT) were isolated from a phage library displaying synthetic human scFv fragments with 6 diversified complementary determining regions (CDRs). A DNT derivative that contained an extended amine group was synthesized and conjugated to the NHS-group that was linked to magnetic beads. Phages specific to the immobilized DNT derivatives were isolated from the library after 4 rounds of sequential binding and elution processes. The displayed scFv fragments from the isolated phages showed consensus CDR sequences. One DNT-specific scFv was expressed in E. coli and purified using Ni-affinity chromatography. The purified DNT-specific scFv binds specifically to the immobilized DNT-derivative with $K_D$ value of $6.0{\times}10^{-7}$ M. The scFv and DNT interaction was not disrupted by the addition of 4-nitrotoluene or benzoic acid. These data demonstrate that the screened scFv from the phage displayed library could be used for selective and sensitive detection of explosives such as TNT.

신령버섯에서 분리된 Glucosylceramide 및 Sterol의 피부 세포 개선 효과 (Effect of Glucosylceramides and Sterols Isolated from Agaricus Blazei Extract on Improvement of Skin Cell)

  • 김정은;이소영;장윤희;진무현
    • 대한화장품학회지
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    • 제46권2호
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    • pp.105-117
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    • 2020
  • 신령버섯(Agaricus blazei Murill)은 항암, 면역력 개선, 항비만 등 다양한 효능이 알려져 있으며, 피부 효능으로는 항산화, 항염, 미백 등에 대하여 보고되었다. 이러한 효능을 뒷받침하기 위하여, 신령버섯의 성분 연구가 진행되었다. 따라서 본 연구에서는 신령버섯 추출물의 피부 효능을 재확인하고 유용한 효능성분을 밝혀내어 이를 화장품 소재로서 이용하고자 하였다. 신령버섯 추출물은 100 ㎍/mL에서 멜라닌 합성 저해, 콜라겐 합성 증진, 보습과 관련된 유전자(hyaluronan synthase-2, 3와 aquaporin-3) 발현 증가를 나타내었다. 이들 화합물은 분광학적 데이터와 문헌값을 비교하여 ergosterol (1), 5-dihydroergosterol (2), cerevisterol (3), cerebroside B (4), cerebroside D (5), adenosine (6), 및 benzoic acid (7)로 동정하였다. 이들 중 비교적 효능이 알려지지 않은 3종의 sterol (1-3)과 2종의 glucosylceramide (4, 5)에 대하여 피부효능을 평가하였으며, 그 결과 5-dihydroergosterol (2)이 마우스 흑색종 세포에서 멜라닌 생성을 억제하였으며, 또한 인간 진피 섬유아세포 세포에서 콜라겐 생합성 촉진하였다. 그리고 cerevisterol (3), cerebroside B (4), cerebroside D (5)는 마우스 대식세포에서 NO 생성을 억제하였으며, 특히 cerebroside D (5)는 인간각질형성세포에서 hyaluronan synthase-2와 aquaporin-3 유전자 발현을 증가시켰다. 따라서 신령버섯 추출물과 분리 화합물은 화장품 소재로 활용 가능 할 것으로 생각된다.

Sesquiterpenoids Bioconversion Analysis by Wood Rot Fungi

  • Lee, Su-Yeon;Ryu, Sun-Hwa;Choi, In-Gyu;Kim, Myungkil
    • 한국균학회소식:학술대회논문집
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    • 한국균학회 2016년도 춘계학술대회 및 임시총회
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    • pp.19-20
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    • 2016
  • Sesquiterpenoids are defined as $C_{15}$ compounds derived from farnesyl pyrophosphate (FPP), and their complex structures are found in the tissue of many diverse plants (Degenhardt et al. 2009). FPP's long chain length and additional double bond enables its conversion to a huge range of mono-, di-, and tri-cyclic structures. A number of cyclic sesquiterpenes with alcohol, aldehyde, and ketone derivatives have key biological and medicinal properties (Fraga 1999). Fungi, such as the wood-rotting Polyporus brumalis, are excellent sources of pharmaceutically interesting natural products such as sesquiterpenoids. In this study, we investigated the biosynthesis of P. brumalis sesquiterpenoids on modified medium. Fungal suspensions of 11 white rot species were inoculated in modified medium containing $C_6H_{12}O_6$, $C_4H_{12}N_2O_6$, $KH_2PO_4$, $MgSO_4$, and $CaCl_2$ for 20 days. Cultivation was stopped by solvent extraction via separation of the mycelium. The metabolites were identified as follows: propionic acid (1), mevalonic acid lactone (2), ${\beta}$-eudesmane (3), and ${\beta}$-eudesmol (4), respectively (Figure 1). The main peaks of ${\beta}$-eudesmane and ${\beta}$-eudesmol, which were indicative of sesquiterpene structures, were consistently detected for 5, 7, 12, and 15 days These results demonstrated the existence of terpene metabolism in the mycelium of P. brumalis. Polyporus spp. are known to generate flavor components such as methyl 2,4-dihydroxy-3,6-dimethyl benzoate; 2-hydroxy-4-methoxy-6-methyl benzoic acid; 3-hydroxy-5-methyl phenol; and 3-methoxy-2,5-dimethyl phenol in submerged cultures (Hoffmann and Esser 1978). Drimanes of sesquiterpenes were reported as metabolites from P. arcularius and shown to exhibit antimicrobial activity against Gram-positive bacteria such as Staphylococcus aureus (Fleck et al. 1996). The main metabolites of P. brumalis, ${\beta}$-Eudesmol and ${\beta}$-eudesmane, were categorized as eudesmane-type sesquiterpene structures. The eudesmane skeleton could be biosynthesized from FPP-derived IPP, and approximately 1,000 structures have been identified in plants as essential oils. The biosynthesis of eudesmol from P. brumalis may thus be an important tool for the production of useful natural compounds as presumed from its identified potent bioactivity in plants. Essential oils comprising eudesmane-type sesquiterpenoids have been previously and extensively researched (Wu et al. 2006). ${\beta}$-Eudesmol is a well-known and important eudesmane alcohol with an anticholinergic effect in the vascular endothelium (Tsuneki et al. 2005). Additionally, recent studies demonstrated that ${\beta}$-eudesmol acts as a channel blocker for nicotinic acetylcholine receptors at the neuromuscular junction, and it can inhibit angiogenesis in vitro and in vivo by blocking the mitogen-activated protein kinase (MAPK) signaling pathway (Seo et al. 2011). Variation of nutrients was conducted to determine an optimum condition for the biosynthesis of sesquiterpenes by P. brumalis. Genes encoding terpene synthases, which are crucial to the terpene synthesis pathway, generally respond to environmental factors such as pH, temperature, and available nutrients (Hoffmeister and Keller 2007, Yu and Keller 2005). Calvo et al. described the effect of major nutrients, carbon and nitrogen, on the synthesis of secondary metabolites (Calvo et al. 2002). P. brumalis did not prefer to synthesize sesquiterpenes under all growth conditions. Results of differences in metabolites observed in P. brumalis grown in PDB and modified medium highlighted the potential effect inorganic sources such as $C_4H_{12}N_2O_6$, $KH_2PO_4$, $MgSO_4$, and $CaCl_2$ on sesquiterpene synthesis. ${\beta}$-eudesmol was apparent during cultivation except for when P. brumalis was grown on $MgSO_4$-free medium. These results demonstrated that $MgSO_4$ can specifically control the biosynthesis of ${\beta}$-eudesmol. Magnesium has been reported as a cofactor that binds to sesquiterpene synthase (Agger et al. 2008). Specifically, the $Mg^{2+}$ ions bind to two conserved metal-binding motifs. These metal ions complex to the substrate pyrophosphate, thereby promoting the ionization of the leaving groups of FPP and resulting in the generation of a highly reactive allylic cation. Effect of magnesium source on the sesquiterpene biosynthesis was also identified via analysis of the concentration of total carbohydrates. Our current study offered further insight that fungal sesquiterpene biosynthesis can be controlled by nutrients. To profile the metabolites of P. brumalis, the cultures were extracted based on the growth curve. Despite metabolites produced during mycelia growth, there was difficulty in detecting significant changes in metabolite production, especially those at low concentrations. These compounds may be of interest in understanding their synthetic mechanisms in P. brumalis. The synthesis of terpene compounds began during the growth phase at day 9. Sesquiterpene synthesis occurred after growth was complete. At day 9, drimenol, farnesol, and mevalonic lactone (or mevalonic acid lactone) were identified. Mevalonic acid lactone is the precursor of the mevalonic pathway, and particularly, it is a precursor for a number of biologically important lipids, including cholesterol hormones (Buckley et al. 2002). Farnesol is the precursor of sesquiterpenoids. Drimenol compounds, bi-cyclic-sesquiterpene alcohols, can be synthesized from trans-trans farnesol via cyclization and rearrangement (Polovinka et al. 1994). They have also been identified in the basidiomycota Lentinus lepideus as secondary metabolites. After 12 days in the growth phase, ${\beta}$-elemene caryophyllene, ${\delta}$-cadiene, and eudesmane were detected with ${\beta}$-eudesmol. The data showed the synthesis of sesquiterpene hydrocarbons with bi-cyclic structures. These compounds can be synthesized from FPP by cyclization. Cyclic terpenoids are synthesized through the formation of a carbon skeleton from linear precursors by terpene cyclase, which is followed by chemical modification by oxidation, reduction, methylation, etc. Sesquiterpene cyclase is a key branch-point enzyme that catalyzes the complex intermolecular cyclization of the linear prenyl diphosphate into cyclic hydrocarbons (Toyomasu et al. 2007). After 20 days in stationary phase, the oxygenated structures eudesmol, elemol, and caryophyllene oxide were detected. Thus, after growth, sesquiterpenes were identified. Per these results, we showed that terpene metabolism in wood-rotting fungi occurs in the stationary phase. We also showed that such metabolism can be controlled by magnesium supplementation in the growth medium. In conclusion, we identified P. brumalis as a wood-rotting fungus that can produce sesquiterpenes. To mechanistically understand eudesmane-type sesquiterpene biosynthesis in P. brumalis, further research into the genes regulating the dynamics of such biosynthesis is warranted.

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