• Title/Summary/Keyword: stilbene

검색결과 162건 처리시간 0.022초

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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    • 제31권4호
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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.

Determination of Fluorescent Whitening Agents in Paper Materials by Ion-Pair Reversed-Phase High-Performance Liquid Chromatography

  • Kim, Jeong Soo;Kim, Do Hwan;Kim, Keon
    • Bulletin of the Korean Chemical Society
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    • 제33권12호
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    • pp.3971-3976
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    • 2012
  • A simple method was developed for the analysis of seven stilbene-type fluorescent whitening agents (FWAs) in paper materials by ion-pair reversed-phase high-performance liquid chromatography with fluorescence detection. These stilbene-type FWAs included two disulfonate, two tetrasulfonate, and three hexasulfonate compounds. After optimization of chromatographic conditions, the FWAs were satisfactorily separated using a reversed-phase column (RP-18) with the following isocratic mobile phase: methanol-water (60:40) containing 17.5 mM TBABr and 10 mM citrate buffer (pH = 7.0). The calibration plot was linear in the range from 5 to 500 ng/mL for two disulfo-FWAs and from 1 to 500 ng/mL for the other five FWAs. Precision levels of the calibration curve as indicated by RSD of response factors were 1.2 and 8.1%. Limits of quantitation (LOQ) ranged from 1.2 to 11 ng/mL.

호장으로부터 분리한 안트라퀴논 및 스틸벤 화합물의 지질과산화 저해활성 (Antilipoperoxidant Activity of Antraquinone and Stilbene from Polygonum cuspidatum)

  • 주시몽;이민원;양기숙
    • 약학회지
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    • 제51권2호
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    • pp.140-144
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    • 2007
  • Polygonum cuspidatum has been used as treatments of dermatitis, gonorrhea, inflammation, and hyperlipidaemia in traditional medicine. We examined liver protective effect on CCl$_4$ inducing hepatotoxicity and anti-oxidative activity by TBA method. Phytochemical examination of Polygonum cuspidatum led to the isolation and characterization of emodin 8-O-${\beta}$-D-glucopyranoside (compound 1), and trans-resveratrol 3-O-${\beta}$-D-glucopyranoside (compound 2). Compounds 1 and 2 enhanced the inhibition of anti-lipid peroxidative effects in liver homogenate. In chemical parameters obtained from serum analysis, compounds 1 and 2 also revealed significant decrease in hepatotoxicity. These results suggested that the antraquinone and stilbene which were isolated from Polygonum cuspidatum might be used as therapeutic agent of hepatitis.

한국산 재배대황 근경의 스틸벤 (Stilbene Compounds from Cultivated Korean Rhubarb Rhizomes)

  • 고성권;황완균;김일혁
    • 약학회지
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    • 제42권1호
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    • pp.1-4
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    • 1998
  • In continued studies on cultivated Korean rhubarb rhizomes, three additional stilbene compounds were isolated from water extract by column chromatographic separation using Sepha dex LH-20, ODS-gel. Compound I, desoxyrhapontigenin(3,5-dihydroxy-4`-methoxystilbene), Compound II, rhapontigenin(3,3`,5-trihydroxy-4`-methoxystilbene), and compound III, piceatannol(3,3`,4`,5-tetrahydroxystilbene) were elucidated based on physico-chemical and spectroscopic evidences(UV, IR, $^1H$-NMR, $^13C$-NMR and Mass).

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Modulation of Cytochrome P450 1B1 Expression by A Stilbene Analog and its Effect on the Sensitivity to Anticancer Agents in Human Cancer Cells.

  • Lee, Sang-Kwang;Park, Sung-Sik;Kim, Mie-Young;Chun, Young-Jin
    • 대한약학회:학술대회논문집
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    • 대한약학회 2003년도 Proceedings of the Convention of the Pharmaceutical Society of Korea Vol.1
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    • pp.209.1-209.1
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    • 2003
  • We have previously shown that 2, 3', 4, 5' -tetramethoxystilbene(TMS) from synthetic trans-stilbene analogues, is one of the most potently selective inhibitor of recombinant human cytochrome P450 1B1 in vitro. In the present studies. the effects of TMS on the expression of cytochrome P450 1B1 were investigated in human cancer cell lines such as MCF-7 and HL -60. TCDD-stimulated P450 1B1 protein and mRNA expression was significantly suppressed by TMS in a dose-dependent manner. (omitted)

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Modulation of carcinogen-activating enzymes by synthetic trans-stilbene analogs

  • Lee, Sang-Kwang;Kim, Sang-Hee;Kim, Mie-Young;Chun, Young-Jin
    • 대한약학회:학술대회논문집
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    • 대한약학회 2002년도 Proceedings of the Convention of the Pharmaceutical Society of Korea Vol.2
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    • pp.312.1-312.1
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    • 2002
  • Previous studies have demonstrated that 2,3',4,5' -tetramethoxystilbene (TMS) and 3,3',4',5,5'-pentamethoxystilbene (PMS) showed selective inhibition of human cytochrome P450 1 Bl and 1A1 in vitro., respectively, In the present study, the effects of synthetic stilbene analogs on the expression of cytochrome P450 1Al or lBl were investigated in human tumor cell lines such as HepG2, MCF-7 and MCF-l0A, TCDD caused a dramatic increase in the amount of P450 1A1 or 1B1 proteins and mRNA levels. (omitted)

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Pulse shape discrimination using a stilbene scintillator array coupled to a large-area SiPM array for hand-held dual particle imager applications

  • Jihwan Boo;Mark D. Hammig;Manhee Jeong
    • Nuclear Engineering and Technology
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    • 제55권2호
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    • pp.648-654
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    • 2023
  • A dual-particle imager (DPI) is configured in a hand-held form factor, then one can efficiently and conveniently deploy the DPI to detect the presence of special nuclear materials (SNM) and identify any isotopic variations that differ from their natural abundances. Here we show that by maximizing the areal coupling between a pixelated scintillator array and the partitioned photosensor readout such as a silicon photomultiplier (SiPM), the information utilization of the gamma-ray and neutron information in the radiation field can be enhanced, thus enabling one to rapidly acquire spatial maps of the distributions on gamma-ray and neutron emitters.

A New Stilbene Dimer and Other Chemical Constituents from Monanthotaxis littoralis with Their Antimicrobial Activities

  • Dongmo, Arnaud Joseph Nguetse;Ekom, Steve Endeguele;Tamokou, Jean-de-Dieu;Tagousop, Cyrille Ngoufack;Harakat, Dominique;Voutquenne-Nazabadioko, Laurence;Ngnokam, David
    • Natural Product Sciences
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    • 제26권4호
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    • pp.317-325
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    • 2020
  • A new dimer stilbene [Monalittorin (1)] and ten known compounds [engeletin (2), aurantiamide acetate (3), lupeol (4), friedelin (5), quercetin (6), tiliroside (7), rutoside (8), astragalin (9), isoquercitrin (10) and quercimeritroside (11)] have been isolated from the leaves of Monanthotaxis littoralis (Annonaceae). The structures of these compounds were established by interpretation of their data, mainly, HR-TOFESIMS, 1-D NMR (1H and 13C) and 2-D NMR (1H-1H COSY, HSQC, HMBC and NOESY) and by comparison with the literature. The evaluation of their antimicrobial activities against three bacteria (Staphylococcus aureus ATCC 25923, Escherichia coli S2 (1) and Pseudomonas aeruginosa PA01) and three fungal strains (Candida albicans ATCC10231, Candida tropicalis PK233 and Cryptococcus neoformans H99) using broth micro dilution method, showed the largest antimicrobial activities of EtOAc fraction and compounds 1, 5, 6, 8 and 11 (MIC = 8 - 64 ㎍/mL). In addition, EtOAc fraction presented synergistic effect with Vancomycin and fluconazole against the tested microorganisms.

Metabolic Engineering for Resveratrol Derivative Biosynthesis in Escherichia coli

  • Jeong, Yu Jeong;Woo, Su Gyeong;An, Chul Han;Jeong, Hyung Jae;Hong, Young-Soo;Kim, Young-Min;Ryu, Young Bae;Rho, Mun-Chual;Lee, Woo Song;Kim, Cha Young
    • Molecules and Cells
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    • 제38권4호
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    • pp.318-326
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    • 2015
  • We previously reported that the SbROMT3syn recombinant protein catalyzes the production of the methylated resveratrol derivatives pinostilbene and pterostilbene by methylating substrate resveratrol in recombinant E. coli. To further study the production of stilbene compounds in E. coli by the expression of enzymes involved in stilbene biosynthesis, we isolated three stilbene synthase (STS) genes from rhubarb, peanut, and grape as well as two resveratrol O-methyltransferase (ROMT) genes from grape and sorghum. The ability of RpSTS to produce resveratrol in recombinant E. coli was compared with other AhSTS and VrSTS genes. Out of three STS, only AhSTS was able to produce resveratrol from p-coumaric acid. Thus, to improve the solubility of RpSTS, VrROMT, and SbROMT3 in E. coli, we synthesized the RpSTS, VrROMT and SbROMT3 genes following codon-optimization and expressed one or both genes together with the cinnamate/4-coumarate:coenzyme A ligase (CCL) gene from Streptomyces coelicolor. Our HPLC and LC-MS analyses showed that recombinant E. coli expressing both ScCCL and RpSTSsyn led to the production of resveratrol when p-coumaric acid was used as the precursor. In addition, incorporation of SbROMT3syn in recombinant E. coli cells produced resveratrol and its mono-methylated derivative, pinostilbene, as the major products from p-coumaric acid. However, very small amounts of pterostilbene were only detectable in the recombinant E. coli cells expressing the ScCCL, RpSTSsyn and SbROMT3syn genes. These results suggest that RpSTSsyn exhibits an enhanced enzyme activity to produce resveratrol and SbROMT3syn catalyzes the methylation of resveratrol to produce pinostilbene in E. coli cells.