• Title/Summary/Keyword: stilbene derivatives

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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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Inhibitory Effects of Stilbene Derivatives from Rheum undulatum on Cyclooxygenase Activity (종대황 스틸벤 유도체의 Cyclooxygenase 저해작용)

  • Lee, Chung-Ryul;Lee, Hak-Sung;Kim, Hyun;Baek, Koo-Hyun;Tokuoka, Kiyoshi;Chung, Sung-Hyun;Ko, Sung-Kwon
    • Korean Journal of Pharmacognosy
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    • v.34 no.1 s.132
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    • pp.25-27
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    • 2003
  • In order to clarify the anti-thrombosis activity of rhubarb, we investigated the effect of stilbene derivatives from rhizomes of Rheum undulatun on cyclooxygenase activity. Stilbene derivatives (desoxyrhapontigenin, rhapontigenin, piceatannol) exhibited the inhibitory effects on COX-1, and desoxyrhapontigenin showed inhibitory effect on COX-2. These inhibitory effect may partially contributed to anti-thrombosis activity of rhubarb.

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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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.

First Hyperpolarizabilities of Heteroaromatic Stilbene Derivatives

  • Cho, Bong-Rae;Lee, Sang-Hae;Yosep Min;Kang, Tae-Im;Jeon, Seung-Joon
    • Journal of Photoscience
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    • v.8 no.2
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    • pp.79-82
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    • 2001
  • 2-(p-Diethylaminostyryl)pyrrole (I) and 2-[5-diethylaminothienyl]vinyl]pyrrole (II) derivatives with systematic variation of the acceptors have been synthesized and their first hyperpolarizabilities were measured. The $\beta$ values increased systematically as the aromatic resonance energy decreased. Moreover, the value of $\beta$ for the former increased gradually as the acceptor strength increased. The opposite trend observed in the latter series of compounds has been attributed to the distorted structure caused by the steric hindrance between the N-methyl group and the acceptor moiety.

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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.

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.

Synthesis and Electroluminescent Properties of Imidazole Derivatives (Imidazole 유도체들의 합성과 유기 발광 특성 연구)

  • 박종욱;서현진
    • Journal of the Korean Institute of Electrical and Electronic Material Engineers
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    • v.16 no.12
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    • pp.1121-1124
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    • 2003
  • We report the photo (PL) and electro luminescence (EL) properties of new conjugated compounds based on imidazole moiety, 4,4' -di(4,5 diphenyl-N-imidazolyl)stilbene(DDPIS) and 4,4'-di(2,4,5-triphenyl-N-imidazolyl)stilbene(DTPIS), as emitting materials. ITO/m-MTDATA/NPB/DDPIS/Alq3/LiF/AI device shows blue EL spectrum at 456 ㎚ and 0.3 cd/ A and turn on voltage at 7 ∼ 8 V. DTPIS shows blue EL spectrum at around λmax=453㎚ and 0.5 cd/A efficiency in ITO/m-MTDATA/NPB/DTPIS/Alq3/LiF/Al device.

Syntheses of Resveratrol and its Hydroxylated Derivatives as Radical Scavenger and Tyrosinase Inhibitor

  • Lee, Hyun-Suck;Lee, Byung-Won;Kim, Mi-Ran;Jun, Jong-Gab
    • Bulletin of the Korean Chemical Society
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    • v.31 no.4
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    • pp.971-975
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    • 2010
  • Eight hydroxylated stilbene derivatives including resveratrol, desoxyrhapontigenin and piceatannol as potential radical scavenger and tyrosinase inhibitor are synthesized using optimized Wittig-Horner reaction for excellent trans-selectivity in good yields. Antioxidant activity was tested against ABTS radical and tyrosinase inhibitory activity was performed with L-tyrosine as the substrate based on previous procedure with some modification. In general, catecholic stilbenes showed stronger activity against ABTS radical and resorcinolic moiety showed stronger tyrosinase inhibitory activity. Synthetic piceatannol which containing both catecholic and resorcinolic moieties showed the strongest activity in both as ABTS radical scavenger and tyrosinase inhibitor with $IC_{50}$ values of 4.1 and $8.6\;{\mu}M$, respectively.