• Title/Summary/Keyword: Structural elucidation

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Structural determination of triterpenic acids in Prunellae Spica by fast atom bombardment tandem mass spectrometry (하고초의 생리활성 성분 Triterpenic Acids의 FAB-MS를 이용한 구조 규명)

  • Ahn, Young Min;Lee, Kang Ro;Hong, Jongki
    • Analytical Science and Technology
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    • v.21 no.4
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    • pp.245-258
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    • 2008
  • Five triterpenic acids as marker compounds were extracted and isolated from Prunellae Spica by column chromatography and reversed-phase high-performance liquid chromatography (HPLC), and their purity was determinated by HPLC (purity ${\geq}90%$). Molecular weight and elemental compositions of the five marker compounds were determined by fast atom bombardment high-resolution mass spectrometry (FAB-HRMS). The structural determination of the five marker compounds was carried out fast atom bombardment collision-induced dissociation tandem mass spectrometry (FAB-CID-MS/MS). The collision-induced dissociation (CID) of protonated molecules $[M+H]^+$ and deprotonated molecules $[M-H]^-$ produced diverse product ions due mainly to retro Diels-Alder reaction (RDA), dehydration and decarboxylation. Moreover, the CID-MS/MS spectra of the $[M-H]^-$ ions were observed charge-remote fragmentation (CRF) patterns. On the basis of interpretation of CID-MS/MS spectra, structural elucidation of triterpenic acids isolated from Prunellae Spica was clearly performed.

Ribosomal Crystallography: Peptide Bond Formation, Chaperone Assistance and Antibiotics Activity

  • Yonath, Ada
    • Molecules and Cells
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    • v.20 no.1
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    • pp.1-16
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    • 2005
  • The peptidyl transferase center (PTC) is located in a protein free environment, thus confirming that the ribosome is a ribozyme. This arched void has dimensions suitable for accommodating the 3'ends of the A-and the P-site tRNAs, and is situated within a universal sizable symmetry-related region that connects all ribosomal functional centers involved in amino-acid polymerization. The linkage between the elaborate PTC architecture and the A-site tRNA position revealed that the A-to P-site passage of the tRNA 3'end is performed by a rotatory motion, which leads to stereochemistry suitable for peptide bond formation and for substrate mediated catalysis, thus suggesting that the PTC evolved by genefusion. Adjacent to the PTC is the entrance of the protein exit tunnel, shown to play active roles in sequence-specific gating of nascent chains and in responding to cellular signals. This tunnel also provides a site that may be exploited for local co-translational folding and seems to assist in nascent chain trafficking into the hydrophobic space formed by the first bacterial chaperone, the trigger factor. Many antibiotics target ribosomes. Although the ribosome is highly conserved, subtle sequence and/or conformational variations enable drug selectivity, thus facilitating clinical usage. Comparisons of high-resolution structures of complexes of antibiotics bound to ribosomes from eubacteria resembling pathogens, to an archaeon that shares properties with eukaryotes and to its mutant that allows antibiotics binding, demonstrated the unambiguous difference between mere binding and therapeutical effectiveness. The observed variability in antibiotics inhibitory modes, accompanied by the elucidation of the structural basis to antibiotics mechanism justifies expectations for structural based improved properties of existing compounds as well as for the development of novel drugs.

Studies on the Presence of all $cis-{\Delta}^{5,11,14}-C_{20:3}$ Fatty Acid in the Seed Oils of Ginkgo (은행종실유의 all $cis-{\Delta}^{5,11,14}-C_{20:3}$ 지방산 존재에 관한 연구)

  • Kim, Seong-Jin;Lee, Kyeng-Hee;Kim, Yeon-Sim;Joh, Yong-Goe
    • Journal of the Korean Applied Science and Technology
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    • v.10 no.1
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    • pp.57-65
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    • 1993
  • The fatty acid, all $cis-{\Delta}^{5,11,14}-C_{20:3}$, in the Gingko nuts oils, was isolated and, purified by urea-adduct method, silver ion silica gel chromatography and HPLC equipped with reversed phase ${\mu}-Bondapak$ $C_{18}$ column. Its structural elucidation was conducted by IR and $^1H$-, $^{13}C$-NMR technique. The fatty acid composition of seed oils mainly consists of linoleic acid(37.73%), vaccenic acid(18.30%), oleic acid(15.18%), palmitic acid(3.37%), palmitoleic acid(3.37%) and ${\Delta}^5$ NMDB fatty acids(8.50%) in which all $cis-{\Delta}^{5,11,14}-C_{20:2}$ predominates.

Engineering Hybrid Proteins by Modular Recombination and Evolutionary Optimization (모듈성 단백질의 재설계 및 개량)

  • Lee, Seung-Goo;Rha, Eu-Gene;Ha, Jae-Seok;Lee, Jeong-Min;Kim, Sun-Hwa
    • Microbiology and Biotechnology Letters
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    • v.36 no.2
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    • pp.149-157
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    • 2008
  • Many proteins consist of distinctive domains that can act independently or cooperatively to achieve a unique function. As these domains evolve from a naturally existing repertoire of functional domains, this implies that domain organization is an intrinsic element involved in building the complex structure and function of proteins. Thus, identifying functional domains would appear to be critical to the elucidation of questions related to protein evolution, folding, and the engineering of hybrid proteins for tai- lored applications. However, the simple application of "Lego-like assembly" to the engineering of hybrid proteins is an oversimplification, as many hybrid constructs lack structural stability, usually due to unfavorable domain contacts. Thus, directed evolution, along with computational studies, may help to engineer hybrid proteins with improved physico-chemical properties. Accordingly, this paper introduces several approaches to functional hybrid protein engineering that potentially can be used to create modulators of gene transcription and cell signaling, and novel biosensors to analyze biological functions in vivo.

Natural Anthraquinone Derivatives from a Marine Mangrove Plant-Derived Endophytic Fungus Eurotium rubrum: Structural Elucidation and DPPH Radical Scavenging Activity

  • Li, Dong-Lil;Li, Xiao-Ming;Wang, Bin-Gui
    • Journal of Microbiology and Biotechnology
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    • v.19 no.7
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    • pp.675-680
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    • 2009
  • There is considerable interest in the isolation of potent radical scavenging compounds from natural resources to treat diseases involving oxidative stress. In this report, four new fungal metabolites including one new bisdihydroanthracenone derivative (1, eurorubrin), two new seco-anthraquinone derivatives [3, 2-O-methyl-9-dehydroxyeurotinone and 4, 2-O-methyl-4-O-(${\alpha}$-D-ribofuranosyl)-9-dehydroxyeurotinone], and one new anthraquinone glycoside [6,3-O-(${\alpha}$-D-ribofuranosyl)-questin], were isolated and identified from Eurotium rubrum, an endophytic fungal strain that was isolated from the inner tissue of the stem of the marine mangrove plant Hibiscus tiliaceus. In addition, three known compounds including asperflavin (2), 2-0-methyleurotinone (5), and questin (7) were also isolated and identified. Their structures were elucidated on the basis of spectroscopic analysis. All of the isolated compounds were evaluated for 1,1-diphenyl-2-picrylhydrazyl (DPPH) radical scavenging activity.

Synthesis and Antimicrobial Activities of Some New Nitroimidazole Derivatives

  • Benkli, Kadriye;Karaburun, Ahmet-Cagrl;Gundogdu-Karaburun, Nalan;Demirayak, Seref;Guven, Klymet
    • Archives of Pharmacal Research
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    • v.26 no.10
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    • pp.773-777
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    • 2003
  • In this study, some new nitroimidazole derivatives were obtained from 2-(2-methyl-5-nitro-1H-imidazol-1-yl)ethylamine dihydrochloride (4) and 1-(2-bromoethyl)-2-methyl-5-nitroimidazole (5), which were prepared using metronidazole. Compound 4 was reacted with arylisothiocyanates (6) to obtain 1-[2-(2-methyl-5-nitroimidazol-1-yl)ethyl]-3-arylthioureas (7) and the latter with $\alpha$-bromoacetophenones (8) to give -3-[2-(2-methyl-5-nitroimidazol-1-yl)ethyl]-2-arylimino-4-aryl-4-thiazolines (9). Also 1-[2-(2-methyl-5-nitroimidazol-1-yl)ethyl]-2-phenyl-4-arylideneimidazolin-5-ones (11) were prepared by reaction of 4 with 2-phenyl-4-arylidene-5-oxazolones (10). The reaction of the other starting material 5 with 5-arylidenethiazolidin-2,4-dione (12) gave 3-[2-(2-methyl-5-nitroimidazol-1-yl)ethyl]-5-arylidenethiazolidin-2,4-dione (13) derivatives. Structural elucidation of the compounds was performed by IR, $^1H-NMR$ and MASS spectroscopic data and elemental analysis results. Antimicrobial activities of the compounds were examined and moderate activity was obtained.

Sugar Constituents of Jalapin from Sweet Potato Tubers (고구마樹脂중 잘라핀의 糖構成에 관한 硏究)

  • SU RAE LEE;KOO HEUNG CHUNG;HO SIK KIM
    • Journal of the Korean Chemical Society
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    • v.13 no.1
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    • pp.96-101
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    • 1969
  • Jalapin purified from the tubers of the sweet potato (Ipomoea batatas) was deacylated and subjected to structural elucidation. Complete and degraded acid hydrolyses indicated the presence of L-rhamnose, D-fucose and D-glucose in the molar ratio of 1: 1: 1 and in the increasing order of acid-stability. While two moles of periodate were consumed per mole of the product, D-glucose survived in the oxidation. The following structure was, therefore, proposed tentatively for the deacylated jalapin: L-$Rha_f$-(1${\to}$4)-D-$Fuc_p$-(1${\to}$3)-D-$Glu_p$-(1${\to}$11)-jalapinolic acid.

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Isolation and Structural Elucidation of Antimicrobial Compounds from Buckwheat Hull

  • Cho Jeong-Yong;Moon Jae-Hak;Kim Hye-Kyung;Ma Seung-Jin;Kim Seon-Jae;Jang Mi-Young;Kawazoe Kazuyoshi;Takaishi Yoshihisa;Park Keun-Hyung
    • Journal of Microbiology and Biotechnology
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    • v.16 no.4
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    • pp.538-542
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    • 2006
  • Three new compounds were isolated from the methanol extracts of buckwheat (Fagopyrum esculentum) hull, and their structures were determined to be 6,7-dihydroxy-3,7-dimethyl-octa-2(Z),4(E)-dienoic acid (1), 6,7-dihydroxy-3,7-dimethyl-octa-2(E),4(E)-dienoic acid (2), and 4,7-dihydroxy-3,7-dimethyl-octa-2(E),5(E)-dienoic acid (3) by NMR and MS spectroscopic analyses. These compounds at $500{\mu}g$ concentration showed antimicrobial activity against Staphylococcus aureus, demonstrated by the paper disc method.

Compounds from a jellyfish-derived fungus Aspergillus fumigates

  • Tao, Guan-yu;Liu, Juan;Jung, Jee H.;Guo, Wei;Wen, Xiao-qiong;Liu, Yonghong
    • Natural Product Sciences
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    • v.22 no.2
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    • pp.82-86
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    • 2016
  • Six compounds were isolated from the secondary metabolites of the jellyfish-derived fungus Aspergillus fumigates, whose structures were identified by chemical methods and spectroscopic analysis as pseurotin F1 (1), azaspirofurans B (2), $(22E,\;24R)-24-methyl-5{\alpha}-cholesta-7,22-diene-3{\beta},5,6{\beta}-triol$ (3), $5{\alpha},8{\alpha}-epidioxyergosta-6,22-dien-3{\beta}-o1$ (4), $cyclo-({\small{L}}-Pro-{\small{L}}-Tyr)$ (5), fumitremorgin C (6). The compounds 1 - 5 were isolated from the fungus Aspergillus fumigates for the first time. The isolated compounds (1 - 6) were evaluated for antibiotic activity and cytotoxicity against six bacterial strains and ten human tumor cell lines, respectively.

Phytochemical constituents from the aerial parts of Salvia plebeia

  • Paje, Leo Adrianne;Lee, Hak-Dong;Choi, Jungwon;Kim, Juree;Kim, Ki Hyun;Yu, A Ram;Bae, Min-Jung;Lee, Sanghyun
    • Journal of Applied Biological Chemistry
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    • v.64 no.4
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    • pp.391-397
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    • 2021
  • Four compounds were isolated from Salvia plebeia aerial parts. Silica gel open column chromatography with a gradient elution system was used to isolate and purify these compounds. Nuclear magnetic resonance spectroscopy and mass spectroscopy were used for structural elucidation and identification, while electronic circular dichroism was used to confirm the absolute configuration. The structures were determined to be 𝛽-sitosterol (1), (-)-1S,5S,8S,10R-1-acetoxy-8-hydroxy-2-oxoeudesman-3,7(11)-dien-8,12-olide (2), ursolic acid (3), and N-methylhydroxylamine (4). Compounds 2 and 4 were isolated for the first time from this plant. Compound 2 was quantitatively analyzed via HPLC/UV. The results showed that the methanol extract of S. plebeia had a higher content of compound 2 (1.20 mg/g) than the ethanol extract (0.55 mg/g). This study could be used as a preliminary step in conducting HPLC/UV analysis of sesquiterpenoids in S. plebeia extract to assess their bioavailability and potency.