Trans-Stilbene

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Sangwon Choi - One of the best experts on this subject based on the ideXlab platform.

  • antioxidative activity of resveratrol and its derivatives isolated from seeds of paeonia lactiflora
    Bioscience Biotechnology and Biochemistry, 2002
    Co-Authors: Eun Ju Chang, Shinkyo Chung, Heui-dong Park, Sangwon Choi
    Abstract:

    Seven stilbenes, a new cis-e-viniferin and the six known stilbenes, trans-resveratrol, trans-resveratrol-4′-O-β-D-glucopyranoside, trans-e-viniferin, gnetin H, and suffruticosol A and B, were isolated and identified from seeds of Paeonia lactiflora. The antioxidative activity of these stilbene derivatives was evaluated against the 2-deoxyribose degradation and rat liver microsomal lipid peroxidation induced by the hydroxyl radical generated via a Fenton-type reaction. Among these stilbenes, trans-e-viniferin and gnetin H significantly inhibited 2-deoxyribose degradation and lipid peroxidation in rat liver microsomes. In addition, cis-e-viniferin, and suffruticosol A and B also exhibited moderate antioxidative activity. These results suggest that resveratrol dimers and trimers, together with resveratrol from seeds of Paeonia lactiflora may be useful as potential sources of natural antioxidants.

  • Cytotoxic and antimutagenic stilbenes from seeds ofPaeonia lactiflora
    Archives of Pharmacal Research, 2002
    Co-Authors: Eun Ju Chang, Heui-dong Park, Sun Mi Shim, Chang Ho Rhee, Jun Hong Park, Sangwon Choi
    Abstract:

    Cytotoxic and antimutagenic effects of a novel cis -ε-viniferin and five known stilbenes, trans -resveratrol, frans -ε-viniferin, gnetin H, suffruticosols A and B, isolated from the seeds of Paeonia lactiflora Pall. (Paeoniaceae) were determined against five different cancer cell lines, and mutagenicity of N -methyl- N '-nitro- N -nitrosoguanidine (MNNG) in Salmonella typhimurium TA100, respectively. Six stilbenes showed cytotoxic activity in a dose-dependent manner, and especially did potent cytotoxic activity against C6 (mouse glioma) cancer cell with IC_50 values ranging from 8.2 to 20.5 ug/ml. trans -Resveratrol showed significant cytotoxic activity against HepG2 (liver hepatoma) and HT-29 (colon) human cancer cell lines with IC_50 values of 11.8 and 25.2 g/ml, respectively. In contrast, trans -ε-viniferin and cis --viniferin, and gnetin H exhibited marked cytotoxic activity against Hela (cervicse) and MCF-7 (breast) human cancer cell lines with IC_50 values of 20.4, 21.5, and 12.9 μg/ml, respectively. However, suffruticosol A and B had less cytotoxic effect against all cancer cells except C6. Meanwhile, six stilbenes exerted antimutagenic activity in a dose-dependent fashion. Of them, trans -resveratrol exhibited the strongest antimutagenic effect against MNNG with IC_50 value of 27.0 μg/plate, while other five resveratrol oligomers also did moderate antimutagenic activity with IC_50 values ranging from 31.7 to 35.2 μg/plate.

  • cytotoxic and antimutagenic stilbenes from seeds of paeonia lactiflora
    Archives of Pharmacal Research, 2002
    Co-Authors: Eun Ju Chang, Heui-dong Park, Sun Mi Shim, Chang Ho Rhee, Jun Hong Park, Sangwon Choi
    Abstract:

    Cytotoxic and antimutagenic effects of a novelcis-e-viniferin and five known stilbenes,trans-resveratrol,frans-e-viniferin, gnetin H, suffruticosols A and B, isolated from the seeds ofPaeonia lactiflora Pall. (Paeoniaceae) were determined against five different cancer cell lines, and mutagenicity ofN-methyl-N'-nitro-N-nitrosoguanidine (MNNG) inSalmonella typhimurium TA100, respectively. Six stilbenes showed cytotoxic activity in a dose-dependent manner, and especially did potent cytotoxic activity against C6 (mouse glioma) cancer cell with IC50 values ranging from 8.2 to 20.5 ug/ml.trans-Resveratrol showed significant cytotoxic activity against HepG2 (liver hepatoma) and HT-29 (colon) human cancer cell lines with IC50 values of 11.8 and 25.2 g/ml, respectively. In contrast,trans-e-viniferin andcis--viniferin, and gnetin H exhibited marked cytotoxic activity against Hela (cervicse) and MCF-7 (breast) human cancer cell lines with IC50 values of 20.4, 21.5, and 12.9 μg/ml, respectively. However, suffruticosol A and B had less cytotoxic effect against all cancer cells except C6. Meanwhile, six stilbenes exerted antimutagenic activity in a dose-dependent fashion. Of them,trans-resveratrol exhibited the strongest antimutagenic effect against MNNG with IC50 value of 27.0 μg/plate, while other five resveratrol oligomers also did moderate antimutagenic activity with IC50 values ranging from 31.7 to 35.2 μg/plate.

Tai Gyu Lee - One of the best experts on this subject based on the ideXlab platform.

  • Highly selective synthesis of Trans-Stilbene oxide over mesoporous Mn-MCM-41 and Zr–Mn-MCM-41 molecular sieves
    Microporous and Mesoporous Materials, 2005
    Co-Authors: Manickam Selvaraj, K. S. Seshadri, A. Pandurangan, Tai Gyu Lee
    Abstract:

    Abstract trans -Stilbene oxide have been synthesized under liquid phase reaction conditions using trans -stilbene in the presence of different oxidants and different solvents over synthesized and characterized Zr–Mn-MCM-41 and Mn-MCM-41 as catalysts. On increasing the Si/(Zr + Mn) ratios of Zr–Mn-MCM-41 and Si/Mn ratios of Mn-MCM-41 catalysts from 49 to 327 and 15 to 102, respectively, the conversion of trans -stilbene, yield and selectivity of trans -stilbene oxide decreased. This may be due to the number of Lewis acid sites in Zr–Mn-MCM-41 and Mn-MCM-41 are found to decrease almost linearly with increasing ratios of Si/(Zr + Mn) and Si/Mn, respectively. Both the Zr–Mn-MCM-41(49) and Mn-MCM-41(31) possesses stronger affinity with trans -stilbene and TBHP, but, the conversion of trans -stilbene, yield and selectivity of Trans-Stilbene oxide decreased in only recyclable Mn-MCM-41. This may be due to decreasing the catalytic activity on the surface of catalysts. In the context, the Si/(Zr + Mn) ratio of 49 is found to be more suitable for the epoxidation of trans -stilbene to highly selective synthesis of trans -stilbene oxide. Thus the yield (76.3%) and selectivity of trans -stilbene oxide (84.58%) are higher in Zr–Mn-MCM-41(49) than that in other Zr–Mn-MCM-41 and Mn-MCM-41 catalysts.

Eun Ju Chang - One of the best experts on this subject based on the ideXlab platform.

  • antioxidative activity of resveratrol and its derivatives isolated from seeds of paeonia lactiflora
    Bioscience Biotechnology and Biochemistry, 2002
    Co-Authors: Eun Ju Chang, Shinkyo Chung, Heui-dong Park, Sangwon Choi
    Abstract:

    Seven stilbenes, a new cis-e-viniferin and the six known stilbenes, trans-resveratrol, trans-resveratrol-4′-O-β-D-glucopyranoside, trans-e-viniferin, gnetin H, and suffruticosol A and B, were isolated and identified from seeds of Paeonia lactiflora. The antioxidative activity of these stilbene derivatives was evaluated against the 2-deoxyribose degradation and rat liver microsomal lipid peroxidation induced by the hydroxyl radical generated via a Fenton-type reaction. Among these stilbenes, trans-e-viniferin and gnetin H significantly inhibited 2-deoxyribose degradation and lipid peroxidation in rat liver microsomes. In addition, cis-e-viniferin, and suffruticosol A and B also exhibited moderate antioxidative activity. These results suggest that resveratrol dimers and trimers, together with resveratrol from seeds of Paeonia lactiflora may be useful as potential sources of natural antioxidants.

  • Cytotoxic and antimutagenic stilbenes from seeds ofPaeonia lactiflora
    Archives of Pharmacal Research, 2002
    Co-Authors: Eun Ju Chang, Heui-dong Park, Sun Mi Shim, Chang Ho Rhee, Jun Hong Park, Sangwon Choi
    Abstract:

    Cytotoxic and antimutagenic effects of a novel cis -ε-viniferin and five known stilbenes, trans -resveratrol, frans -ε-viniferin, gnetin H, suffruticosols A and B, isolated from the seeds of Paeonia lactiflora Pall. (Paeoniaceae) were determined against five different cancer cell lines, and mutagenicity of N -methyl- N '-nitro- N -nitrosoguanidine (MNNG) in Salmonella typhimurium TA100, respectively. Six stilbenes showed cytotoxic activity in a dose-dependent manner, and especially did potent cytotoxic activity against C6 (mouse glioma) cancer cell with IC_50 values ranging from 8.2 to 20.5 ug/ml. trans -Resveratrol showed significant cytotoxic activity against HepG2 (liver hepatoma) and HT-29 (colon) human cancer cell lines with IC_50 values of 11.8 and 25.2 g/ml, respectively. In contrast, trans -ε-viniferin and cis --viniferin, and gnetin H exhibited marked cytotoxic activity against Hela (cervicse) and MCF-7 (breast) human cancer cell lines with IC_50 values of 20.4, 21.5, and 12.9 μg/ml, respectively. However, suffruticosol A and B had less cytotoxic effect against all cancer cells except C6. Meanwhile, six stilbenes exerted antimutagenic activity in a dose-dependent fashion. Of them, trans -resveratrol exhibited the strongest antimutagenic effect against MNNG with IC_50 value of 27.0 μg/plate, while other five resveratrol oligomers also did moderate antimutagenic activity with IC_50 values ranging from 31.7 to 35.2 μg/plate.

  • cytotoxic and antimutagenic stilbenes from seeds of paeonia lactiflora
    Archives of Pharmacal Research, 2002
    Co-Authors: Eun Ju Chang, Heui-dong Park, Sun Mi Shim, Chang Ho Rhee, Jun Hong Park, Sangwon Choi
    Abstract:

    Cytotoxic and antimutagenic effects of a novelcis-e-viniferin and five known stilbenes,trans-resveratrol,frans-e-viniferin, gnetin H, suffruticosols A and B, isolated from the seeds ofPaeonia lactiflora Pall. (Paeoniaceae) were determined against five different cancer cell lines, and mutagenicity ofN-methyl-N'-nitro-N-nitrosoguanidine (MNNG) inSalmonella typhimurium TA100, respectively. Six stilbenes showed cytotoxic activity in a dose-dependent manner, and especially did potent cytotoxic activity against C6 (mouse glioma) cancer cell with IC50 values ranging from 8.2 to 20.5 ug/ml.trans-Resveratrol showed significant cytotoxic activity against HepG2 (liver hepatoma) and HT-29 (colon) human cancer cell lines with IC50 values of 11.8 and 25.2 g/ml, respectively. In contrast,trans-e-viniferin andcis--viniferin, and gnetin H exhibited marked cytotoxic activity against Hela (cervicse) and MCF-7 (breast) human cancer cell lines with IC50 values of 20.4, 21.5, and 12.9 μg/ml, respectively. However, suffruticosol A and B had less cytotoxic effect against all cancer cells except C6. Meanwhile, six stilbenes exerted antimutagenic activity in a dose-dependent fashion. Of them,trans-resveratrol exhibited the strongest antimutagenic effect against MNNG with IC50 value of 27.0 μg/plate, while other five resveratrol oligomers also did moderate antimutagenic activity with IC50 values ranging from 31.7 to 35.2 μg/plate.

Akihiro Ito - One of the best experts on this subject based on the ideXlab platform.

  • Metabolic activation of the proestrogens Trans-Stilbene and Trans-Stilbene oxide by rat liver microsomes
    Toxicology and applied pharmacology, 2000
    Co-Authors: Kazumi Sugihara, Shigeyuki Kitamura, Seigo Sanoh, Shigeru Ohta, Nariaki Fujimoto, Satoshi Maruyama, Akihiro Ito
    Abstract:

    A liver microsome-mediated activation of the proestrogens Trans-Stilbene and Trans-Stilbene oxide was found in this study. Trans-Stilbene and Trans-Stilbene oxide were negative in estrogen reporter assay using estrogen-responsive human breast cancer cell line MCF-7 and growth assay in rat pituitary tumor cell line MtT/E-2. However, these compounds exhibited estrogenic activity after incubation with liver microsomes of 3-methylcholanthrene-treated rats in the presence of NADPH. In contrast, cis-stilbene and cis-stilbene oxide did not show estrogenic activity after such incubation. When Trans-Stilbene was incubated with the liver microsomes of 3-methylcholanthrene-treated rats in the presence of NADPH, two metabolites were detected by HPLC. They were identified unequivocally as trans-4-hydroxystilbene and trans-4, 4'-dihydroxystilbene by mass and UV spectral comparison with authentic samples. The oxidase activity of the liver microsomes toward Trans-Stilbene was inhibited by SKF 525-A and alpha -naphthoflavone. Minor activity was observed when liver microsomes of untreated or phenobarbital-treated rats were used instead of those from 3-methylcholanthrene-treated rats. trans-4-Hydroxystilbene and trans-4,4'-dihydroxystilbene exhibited significant estrogenic activities. These results suggest that the estrogenic activities of Trans-Stilbene and Trans-Stilbene oxide were due to formation of hydroxylated metabolites.

Veronika Somoza - One of the best experts on this subject based on the ideXlab platform.

  • metabolism and bioavailability of trans resveratrol
    Molecular Nutrition & Food Research, 2005
    Co-Authors: Elisabeth Wenzel, Veronika Somoza
    Abstract:

    Resveratrol (3,4′,5-trihydroxy-Trans-Stilbene) is a polyphenolic compound accounting to the stilbene class. Most stilbenes in plants act as antifungal phytoalexins, compounds that are usually synthesized only in response to infection or injury. Resveratrol has been detected in trees, in a few flowering plants, in peanuts, and in grapevines. The major dietary sources of resveratrol include grapes, wine, peanuts, and peanut products. Numerous in vitro studies describe different biological effects of resveratrol. The major impacts are the antioxidative, anti-inflammatory, and estrogenic effects as well as anticancer and chemopreventive activities. In order to reveal information on absorption, metabolism, and the consequent bioavailability of resveratrol, different research approaches were performed, including in vitro, ex vivo, and in vivo models, all of which are considered in this review. Summarizing the data, resveratrol is absorbed and metabolized. Around 75% of this polyphenol are excreted via feces and urine. The oral bioavailability of resveratrol is almost zero due to rapid and extensive metabolism and the consequent formation of various metabolites as resveratrol glucuronides and resveratrol sulfates. The potential biologic activity of resveratrol conjugates should be considered in future investigations.

  • Metabolism and bioavailability of trans‐resveratrol
    Molecular Nutrition & Food Research, 2005
    Co-Authors: Elisabeth Wenzel, Veronika Somoza
    Abstract:

    Resveratrol (3,4′,5-trihydroxy-Trans-Stilbene) is a polyphenolic compound accounting to the stilbene class. Most stilbenes in plants act as antifungal phytoalexins, compounds that are usually synthesized only in response to infection or injury. Resveratrol has been detected in trees, in a few flowering plants, in peanuts, and in grapevines. The major dietary sources of resveratrol include grapes, wine, peanuts, and peanut products. Numerous in vitro studies describe different biological effects of resveratrol. The major impacts are the antioxidative, anti-inflammatory, and estrogenic effects as well as anticancer and chemopreventive activities. In order to reveal information on absorption, metabolism, and the consequent bioavailability of resveratrol, different research approaches were performed, including in vitro, ex vivo, and in vivo models, all of which are considered in this review. Summarizing the data, resveratrol is absorbed and metabolized. Around 75% of this polyphenol are excreted via feces and urine. The oral bioavailability of resveratrol is almost zero due to rapid and extensive metabolism and the consequent formation of various metabolites as resveratrol glucuronides and resveratrol sulfates. The potential biologic activity of resveratrol conjugates should be considered in future investigations.