• Title/Summary/Keyword: stilbene

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The Identification of Stilbene Compounds and the Change of Their Contents in UV-irradiated Grapevine Leaves (자외선 조사 포도 잎에서 Stilbene 화합물의 동정과 함량의 변화)

  • Choi, Seong-Jin
    • Horticultural Science & Technology
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    • v.29 no.4
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    • pp.374-381
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    • 2011
  • Stilbenes are polyphenolic natural products, which have antioxidative and antifungal activities. In some plants, including grapevine, the stilbene compounds, as resveratrol derivatives, exist in very diverse forms. Experiments to identify the individual stilbene compounds were carried out first to quantify them in UV-irradiated grapevine leaves. For this, stilbene glycosides were extracted from grapevine leaves which irradiated intensively with UV light. The glycoside samples were hydrolyzed by ${\beta}$-glucosidase, before analyzed by HPLC-mass spectrometer at each m/z corresponding to the mass of specific stilbenes. As results, in chromatograms, the enzymatic hydrolysis resulted in decrease and increase of the peaks expected for glycosides and aglycones, respectively. The samples were also exposed to sunlight in order to photo-isomerize the stilbene compounds. The light exposure resulted in disappearance and appearance of peaks expected for trans- and cis-isomers of stilbenes, respectively. Such a change of the peaks in chromatograms provided information needed for the inference to peak components. In this way, it was possible to identify 16 kinds of stilbene compounds from grapevine leaves. The identified stilbenes were quantified from grapevine leaves irradiated mildly by UV light. The UV-irradiation increased markedly in the content of stilbene compounds, especially trans-resveratrol by several hundredfold. In addition, piceatannol, which is a mere minor component of stilbenes in control leaves and a more active radical scavenger than resveratrol, was also increased by several tenfold by the treatment. The increase in stilbene contents as influenced by UV irradiation seems to be one of the stress coping responses of grapevine as a hormesis phenomenon.

Induction of Quinone Reductase Activity by Stilbene Analogs in Mouse Hepa 1c1c7 Cells

  • Heo, Yoen-Hoi;Kim, Sang-hee;Park, Jae-Eun;Jeong, Lak-Shin;Lee, Sang-Kook
    • Archives of Pharmacal Research
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    • v.24 no.6
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    • pp.597-600
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    • 2001
  • Based on the potential cancer chemoprebentive activity of resveratrol, a trihydroxystilbene with the induction of quinone reductase activeity this study was designed to determine if stilbene-related compounds were inducers of phase ll detoxifying metabolic enzyme quinone reductase (QR) in the mouse hepatoma Hepa 1c1c7 cells. Among the thirteen compounds tested, several compounds including 3,4,5,3',5'-pentamethoxy-trans-stibene were found to potentially induce QR activity in this cell line. In addition, substitution with 3-thiofurane ring instead of phenyl ring in the stilbene skeleton also exhibited potential induction of QR activity. This result will give primary information to design the potential inducers of QR activity in the stilbene analogs.

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Syntheses and Characterization of Polyurethane Polymers with Versatile Stilbene Chromophores (Stilbene 발광 유도체를 가지는 Polyurethane을 기본으로 하는 고분자의 합성 및 특성)

  • Jin, Youngeup;Noh, Ji Young;Park, Seong Soo;Ju, Changsik;Suh, Hongsuk
    • Applied Chemistry for Engineering
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    • v.22 no.4
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    • pp.348-352
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    • 2011
  • In this research, we have synthesized new pendant-type polyurethane polymers by introducing various chromophores with stilbene derivatives in the side-chain of the polymer backbone. The Stilbene monomers, N,N-bis(2-hydroxyethyl) amino-4'-cyanostilbene, N,N-bis(2-hydroxyethyl)amino-4'-methoxy stilbene, N,N-bis(2-hydroxyethyl)amino-4'-acetylstilbene, and N,N-bis(2-hydroxyethyl) amino stilbene, were synthesized by Wittig reaction. Another stilbene monomer, N,N-bis(2-hydroxyethyl)amino-4'-nitrostilbene, was synthesized by Knoevenagel condensation. By the measurement of UV-Vis absorption and Photoluminescence (PL) spectrum, we found that introduction of the electron-withdrawing group as a substituent shifts both UV-Vis and PL spectra to longer wavelength, and the introduction of the electron-donating group results in blue-shift of the spectrum. In case of polymer with $NO_2$ group as a substituent, PL is quenched.

Spectroscopic Evidence for Aggregation of Stilbene Derivatives in Solution

  • Aguiar, M.;Akcelrud, L.;Pinto, M.R.;Atvars, T.D.Z.;Karasz, F.E.;Saltiel, Jack
    • Journal of Photoscience
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    • v.10 no.1
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    • pp.149-155
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    • 2003
  • The absorption, fluorescence and fluorescence-excitation spectra of concentrated toluene solutions of selected para substituted trans-stilbene derivatives provide strong evidence for aggregation. A red-shifted fluorescence spectrum peaking at 420 nm gains in intensity as the stilbene concentration is increased. The excitation spectrum of this new emission is well to the red of the normal stilbene absorption spectrum, consistent with the appearance of a red shifted shoulder in the UV spectrum. Formation of a fluorescent ground state dimer (or higher aggregate) is proposed to account for these observations. The presence of polar substituents is crucial to the formation of this ground state complex.

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Primary Screening of QSAR Descriptors to Determine Biological Activities of Stilbene Derivatives (스틸벤유도체의 생물활성도를 예측하기 위한 QSAR 분자표현자의 검색방법에 관한 연구)

  • 김재현;고동수;엄애선
    • Environmental Analysis Health and Toxicology
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    • v.16 no.3
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    • pp.115-120
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    • 2001
  • The predictive screening of various molecular descriptors for predicting cyclooxygenase inhibitor, lipooxygenase inhibitor, leucotriene synthesis inhibitor, leucotriene antagonist activities of Stilbene moieties have been investigated for the application of quantitative structure-activity relationships (QSAR). The biological activities for 36 compounds were computed by the PASS program and molecular descriptors are cited from literatures or calculated, to investigate feasibility of screening relevant descriptors and of their applications among biological endpoints. Fairly good correlations varying from 0.7828 to 0.9032 were obtained using 12 descriptors with 29 Stilbene derivatives and 5 diazo-compounds. Our studies reveal that LogKow, electron density(X), electron density (Y),4th-order valence connectivity and water solubility can be usefully employed to predict biological activities of stilbene derivatives with simple regression models.

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Synthesis and Evaluation of Cytotoxicity of Stilbene Analogues

  • Lee, Sang-Kook;Nam, Kyung-Ae;Hoe, Yeon-Hoi;Min, Hye-Young;Kim, Eun-Young;Ko, Hyojin;Song, Soyoung;Lee, Taeho;Kim, Sanghee
    • Archives of Pharmacal Research
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    • v.26 no.4
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    • pp.253-257
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    • 2003
  • Resveratrol analogs were newly synthesized and evaluated for cytotoxicity in cultured human lung and colon cancer cells. 3,5,4-Trimethoxy-trans-stilbene and 3,5,2',4'-tetramethoxy-trans-stilbene were found to be more potent rather than resveratrol. 3,4,5-Trimethoxy-4'-bromo-cis-stilbene was the most active among the test compounds.

Effect of Stilbene Derivatives from Rheum undulatum on Carrageenan-Induced Acute Edema in Rats (Carrageenan 유발 족부종에 미치는 종대황 스틸벤 유도체의 효과)

  • Ko, Sung-Kwon;Shin, Cha-Gyun;Lee, Hak-Sung;Han, Sung-Tai;Yang, Byung-Wook;Im, Byung-Ok;Chung, Sung-Hyun
    • Korean Journal of Pharmacognosy
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    • v.35 no.2 s.137
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    • pp.171-174
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    • 2004
  • In order to examine the anti-ohyul (anti-inflammatory) activity of rhubarb, we investigated the effects of stilbene derivatives obtained from rhizomes of Rheum undulatum on the carrageenan-induced hind paw edema in rats. Administration of stilbene aglycon (rhapontigenin) at doses of 50 and 100 mg/kg exhibited the anti- edema effect in dose dependent manner and stilbene glycosides $(rhaponticin,\;piceatannol-3'-O-{\beta}-D-glucopyranoside)$ at a dose of 100 mg/kg also showed inhibitory effect on the carrageenan-induced edema. These inhibitory effects may ascribed, at least in part, to the anti-ohyul activity of rhubarb.

Development of an energy and efficiency calibration method for stilbene scintillators

  • Kim, Chanho;Kim, Jaehyo;Hong, Wooseong;Yeom, Jung-Yeol;Kim, Geehyun
    • Nuclear Engineering and Technology
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    • v.54 no.10
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    • pp.3833-3840
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    • 2022
  • A method for calibrating the energy scale and detection efficiency of stilbene scintillators is presented herein. This method can be used to quantitatively analyze the Compton continuum of gamma-ray spectra obtained using such scintillators. First, channel-energy calibration was conducted by fitting a semi-empirical equation for the Compton continuum to the acquired energy spectrum and a new method to evaluate the intrinsic detection efficiency, called intrinsic Compton efficiency, of stilbene scintillators was proposed. The validity of this method was verified by changing experimental conditions such as the number of sources being measured simultaneously and the detector-source distance. According to the energy calibration, the standard error for the estimated Compton edge position was ±1.56 keV. The comparison of the intrinsic Compton efficiencies calculated from the single- and two-source spectra showed that the mean absolute difference and the mean absolute percentage difference are 0.031 %p and 0.557%, respectively, demonstrating reasonable accuracy of this method. The feasibility of the method was confirmed for an energy range of 0.5-1.5 MeV, showing that stilbene scintillators can be used to quantitatively analyze gamma rays in mixed-radiation fields.

Regioselective Benzylic Thioether Formation from Polybydroxy Stilbene

  • Koh, Dongsoo;Park, Jongmin;Lim, Yoongho
    • Journal of Applied Biological Chemistry
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    • v.44 no.1
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    • pp.20-22
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    • 2001
  • We have attempted to synthesize polyhydroxy stilbene compounds through the benzyl thioether moiety. During synthesis, we unexpectedly observed that demethylation of the compound under $AlCl_3$ in ethanethiol resulted in a regioselective addition of thiol to the double bond as well as complete demethylation. We report on the regioselective short synthesis for general structure and its structural identification.

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Effects of Stilbene Derivatives from Rheum undulatum on $5{\alpha}-Reductase$ Activity ($5{\alpha}-Reductase$ 활성에 미치는 종대황 스틸벤 유도체의 영향)

  • Ko, Sung-Kwon
    • Korean Journal of Pharmacognosy
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    • v.31 no.2
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    • pp.245-248
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    • 2000
  • As a series of the studies on cultivated Korean rhubarb rhizomes (Rheum undulatum), five stilbene derivatives were screened for inhibitory activity against $5{\alpha}-reductase$. Of these, desoxyrhapontigenin, rhapontigenin, and piceatannol exhibited inhibition, whereas, two other stilbene glycosides, rhaponticin and $piceatannol-3'-O-{\beta}-D-glucopyranoside$ did not show the inhibition.

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