• Title/Summary/Keyword: ESI-MS/MS

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Isolation and Structure Determination of a Proteasome Inhibitory Metabolite from a Culture of Scytonema hofmanni

  • Shim, Sang-Hee;Chlipala, George;Orjala, Jimmy
    • Journal of Microbiology and Biotechnology
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    • v.18 no.10
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    • pp.1655-1658
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    • 2008
  • Cyanobacteria, blue-green algae, are a rich source of bioactive secondary metabolites with many potential applications. The ubiquitin-proteasome proteolytic system plays an important role in selective protein degradation and regulates cellular events including apoptosis. Cancer cells are more sensitive to the proapoptotic effects of proteasome inhibition than normal cells. Thus, proteasome inhibitors can be potential anticancer agents. Cyanobacteria have been shown to be a rich source of highly effective inhibitors of proteases. A proteasome inhibitor was screened from an extract of the culture of Scytonema hofmanni on the basis of its inhibitory activity, which led to the isolation of nostodione A with an $IC_{50}$ value of 50${\mu}M$. Its structure was determined by spectroscopic methods such as $^{1}H$-NMR and ESI-MS spectral analyses.

Chemical and Biological Investigations of the Constitutive Phenolics of Two Egyptian Folk-Medicinal Plants; A Novel Phenolic from the Galls of Tamarix aphylla

  • Barakat, Heba H.;Nada, Somaia A.
    • Natural Product Sciences
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    • v.2 no.2
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    • pp.96-101
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    • 1996
  • A new natural product, 3,4,8-trihydroxybenzopyranopyran-6,9-dione was isolated from the aqueous ethanolic gall extract of Tamarix aphylla (Tamaricaceae) along with the known phenolics, monodecarboxyellagic acid and brevifolin carboxylic acid as well. The structures have been established by ESI-MS, $^1H$ and $^{13}C$ NMR spectral analysis. Antiinflammatory, antipyretic and ulcerogenic activities determination for both plant (Tamarix aphylla and Phragmites australis) were carried out on aq. ethanolic of extracts.

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Structure elucidation of 11-epiterpestacin glycoside (11-ETG) isolated from Bipolaris sorokiniana NSDR-011

  • Lim, Chi-Hwan;Nihashi, Youichirou
    • Journal of Applied Biological Chemistry
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    • v.61 no.1
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    • pp.79-82
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    • 2018
  • An ${\alpha}-{\text\tiny{D}}-glucoside$ of sesterterpene, 11-epiterpestacin, was isolated from the culture of a filamentous fungus Bipolaris sorokiniana NSDR-011. The structure was elucidated by chemical studies and spectroscopic methods including NMR and ESI-MS. 11-ETG (1) named arbitrarily did not inhibit the root growth of Italian ryegrass seedlings even at the level of 200 ppm, while its aglycone 11-ET (2) completely inhibited root growth at level of 100 ppm.

Synthesis of 2'-Hydroxydihydrochalcone from Flavone

  • Kim, Mi-Hyang;Shin, Bok-Kyu;Won, Dong-Ho;Han, Jae-Hong
    • Journal of Applied Biological Chemistry
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    • v.50 no.2
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    • pp.85-87
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    • 2007
  • To establish the synthetic method for dihydrochalcones as an important bioactive compounds, 2'-hydroxydihydrochalcone has been synthesized from the reduction of flavone in 20% yield. Flavone with five equivalents of ammonium formate in the presence of Pd/C in methanol under $N_2$ atmosphere produced the C-ring opened product. It was characterized by UV-VIS, ESI-MS and $^1H-NMR$ spectroscopy, and identified as 2'-hydroxydihydrochalcone.

Production of 1,5-Dihydroxy-3-Methoxy-7-Methylanthracene-9,10-Dione by Submerged Culture of Shiraia bambusicola

  • Cai, Yujie;Ding, Yanrui;Tao, Guanjun;Liao, Xiangru
    • Journal of Microbiology and Biotechnology
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    • v.18 no.2
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    • pp.322-327
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    • 2008
  • 1,5-Dihydroxy-3-methoxy-7-methylanthracene-9,10-dione (shiraiarin) is a kind of antitumor and antibacterial anthraquinone, and was produced for the first time from the submerged fermentation of Shiraia bambusicola, as confirmed by ESI-MS and NMR. The production of shiraiarin was significantly influenced when varying the carbon source, and a high amount of shiraiarin was only achieved when using lactose. The production of shiraiarin was also stimulated when using $NaNO_3$ as the nitrogen source, whereas other nitrogen sources inhibited its production. Shiraiarin was formed during the stationary phase with a pH value higher than 8. The production of shiraiarin was inhibited by sporulation.

An Antibacterial Compound against Pasteurella haemolytica Poduced by Streptomyces sp. 51086 (반추동물 급성기관지폐렴균 Pasteurella haemolytica에 항균활성을 갖는 물질의 특성규명)

  • 강희철;유인자;윤봉식;전용수;유익동
    • Microbiology and Biotechnology Letters
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    • v.27 no.4
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    • pp.339-343
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    • 1999
  • Pasteurella haemolytica is well known to cause severe pneumonia, consolidation and oedema of the lung, and fibrinous pleurisy under the stress and infection of virus in the cattle. In the course of our screening for antimicrobial agents against P.haemloytica, compound 51086 has been isolated from the fermentation broth of Streptimyces sp. 51086. The compound 51086 was purified by SiO2, Sephadex LH-20 and ODS column chromatographies and HPLC, subsequently. The structure of compound 51086 was determined as hygromycin A by combination of 1H NMR, 13C NMR, HMBC, and ESI-MS. This compound showed significant antibacterial activity against P.haemolytica and P.multocida.

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Isolation and Identification of an Unauthorized Tadalafil Analogue in a Commercial Functional Food (시판 기능성식품으로부터의 타다라필 유도체 부정첨가물질의 분리 및 구조규명)

  • Baek, Du-Jong
    • YAKHAK HOEJI
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    • v.54 no.4
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    • pp.240-243
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    • 2010
  • High-performance liquid chromatography (HPLC) screening method revealed that a propolis product marketed as a functional food contained an undeclared substance similar to tadalafil, the active ingredient of the prescription drug Cialis$^{(R)}$ approved for the treatment of male erectile dysfunction. In order to identify the illegal additive, the propolis product was extracted with methylene chloride, and the extract was purified further using semipreparative HPLC. The chemical structure of the isolated substance was elucidated based on IR, LC/MS-ESI, and $^1H$- and $^{13}C$-NMR spectroscopy, which showed the characteristics similar to tadalafil. The only difference was the substitution of the methyl group at the piperazinedione ring of tadalafil to the amino group of the identified illegal additive.

Synthesis and DNA-binding Properties of Trehalose-tethered Monomeric and Dimeric Berberines

  • Wang, Yong-Min;Zhou, Chun-Qiong;Chen, Jin-Xiang;Chen, Wen-Hua
    • Bulletin of the Korean Chemical Society
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    • v.34 no.3
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    • pp.749-752
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    • 2013
  • Trehalose-tethered monomeric and dimeric berberines were synthesized in 50% and 30% from the reaction of berberrubine with 6-tosyl-${\alpha}$,${\alpha}^{\prime}$-trehalose and 6,6'-ditosyl-${\alpha}$,${\alpha}^{\prime}$-trehalose, respectively, and fully characterized by MS (HR and ESI) and NMR ($^1H$, $^{13}C$, COSY and HSQC). Spectrophotometric and spectrofluorimetric titrations indicated that compared with berberine, trehalose-tethered monomeric berberine had comparable DNA-binding affinity toward calf-thymus DNA, whereas trehalose-spaced dimeric berberine exhibited higher DNA-binding affinity. The potential application of these conjugates is also briefly discussed.

Simple synthesis of Biphosphonates with Excellent Flameproofing Properties

  • Cao, Yang;Zhang, Weiwei;Yang, Xufeng;Yang, Jinfei;Zhi, Huizhen
    • Korean Chemical Engineering Research
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    • v.52 no.2
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    • pp.187-190
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    • 2014
  • Four excellent halogen-free biphosphonate flame retardants (EBDMP, EBDEP, MBDMP, MBDEP) were synthesized through polycondensation and Arbuzov rearrangement reactions without using any solvents. The products were characterized by ESI-MS, FT-IR and $^1H$ NMR. The application of EBDEP in polyurethane soft foam was studied and the results illustrated its excellent flame-proofing properties.

Two New Caffeoyl Threonate Esters from the Leaves of Toxicodendron vernicifluum

  • Jang, Jae Young;Ahn, Jong Hoon;Jo, Yang Hee;Turk, Ayman;Kang, So Young;Hwang, Bang Yeon;Lee, Mi Kyeong
    • Natural Product Sciences
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    • v.25 no.4
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    • pp.354-357
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    • 2019
  • Toxicodendron vernicifluum, also called as Rhus verniciflua is a deciduous tree belonging to Anacardiaceae family. Two new caffeoyl threonate esters, rhuseols A (1) and B (2), together with 5-O-(E)-caffeoylquinic acid methyl ester (3) were isolated from the leaves of T. vernicifluum. The structures of isolated compounds were established by using 1D and 2D NMR in combination with HR-ESI-MS. Compounds 1 - 3 showed DPPH radical scavenging effects with IC50 values of 47.9, 107.8 and 15.4 μM, respectively. Taken together, these compounds might contribute to the antioxidant properties of the leaves of T. vernicifluum, which will be useful for various oxidative stress mediated diseases.