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Judy L Bolton - One of the best experts on this subject based on the ideXlab platform.

  • induction of nAd p h quinone oxidoreductAse 1 nqo1 by glycyrrhizA species used for women s heAlth differentiAl effects of the michAel Acceptors isoliquiritigenin And LicochAlcone A
    Chemical Research in Toxicology, 2015
    Co-Authors: Atieh Hajirahimkhan, Charlotte Simmler, Shaonong Chen, Guido F Pauli, Birgit M Dietz, Huali Dong, Daniel D Lantvit, Dejan Nikolic, Richard B Van Breemen, Judy L Bolton
    Abstract:

    For the AlleviAtion of menopAusAl symptoms, women frequently turn to botAnicAl dietAry supplements, such As licorice And hops. In Addition to estrogenic properties, these botAnicAls could Also hAve chemopreventive effects. We hAve previously shown thAt hops And its MichAel Acceptor xAnthohumol (XH) induced the chemoprevention enzyme, NAD(P)H:quinone oxidoreductAse 1 (NQO1), in vitro And in vivo. Licorice species could Also induce NQO1, As they contAin the MichAel Acceptors isoliquiritigenin (LigC) found in GlycyrrhizA glAbrA (GG), G. urAlensis (GU), G. inflAtA (GI), And LicochAlcone A (LicA) which is only found in GI. These licorice species And hops induced NQO1 Activity in murine hepAtomA (HepA1c1c7) cells; hops ≫ GI > GG ≅ GU. SimilAr to the known chemopreventive compounds curcumin (turmeric), sulforAphAne (broccoli), And XH, LigC And LicA were Active dose-dependently; sulforAphAne ≫ XH > LigC > LicA ≅ curcumin ≫ liquiritigenin (LigF). Induction of the AntioxidAnt response element luciferAse in humAn he...

  • differentiAl effects of glycyrrhizA species on genotoxic estrogen metAbolism LicochAlcone A downregulAtes p450 1b1 whereAs isoliquiritigenin stimulAtes it
    Chemical Research in Toxicology, 2015
    Co-Authors: Tareisha L Dunlap, Shuai Wang, Charlotte Simmler, Shaonong Chen, Guido F Pauli, Birgit M Dietz, Judy L Bolton
    Abstract:

    Estrogen chemicAl cArcinogenesis involves 4-hydroxylAtion of estrone/estrAdiol (E1/E2) by P450 1B1, generAting cAtechol And quinone genotoxic metAbolites thAt cAuse DNA mutAtions And initiAte/promote breAst cAncer. InflAmmAtion enhAnces this effect by upregulAting P450 1B1. The present study tested the three AuthenticAted medicinAl species of licorice [GlycyrrhizA glAbrA (GG), G. urAlensis (GU), And G. inflAtA (GI)] used by women As dietAry supplements for their Anti-inflAmmAtory Activities And their Ability to modulAte estrogen metAbolism. The pure compounds, liquiritigenin (LigF), its chAlcone isomer isoliquiritigenin (LigC), And the GI-specific LicochAlcone A (LicA) were Also tested. The licorice extrActs And compounds were evAluAted for Anti-inflAmmAtory Activity by meAsuring inhibition of iNOS Activity in mAcrophAge cells: GI ≫ GG > GU And LigC ≅ LicA ≫ LigF. The MichAel Acceptor chAlcone, LicA, is likely responsible for the Anti-inflAmmAtory Activity of GI. A sensitive LC-MS/MS AssAy wAs employed to...

  • differentiAl effects of glycyrrhizA species on genotoxic estrogen metAbolism LicochAlcone A downregulAtes p450 1b1 whereAs isoliquiritigenin stimulAtes it
    Chemical Research in Toxicology, 2015
    Co-Authors: Tareisha L Dunlap, Shuai Wang, Charlotte Simmler, Shaonong Chen, Guido F Pauli, Birgit M Dietz, Judy L Bolton
    Abstract:

    Estrogen chemicAl cArcinogenesis involves 4-hydroxylAtion of estrone/estrAdiol (E1/E2) by P450 1B1, generAting cAtechol And quinone genotoxic metAbolites thAt cAuse DNA mutAtions And initiAte/promote breAst cAncer. InflAmmAtion enhAnces this effect by upregulAting P450 1B1. The present study tested the three AuthenticAted medicinAl species of licorice [GlycyrrhizA glAbrA (GG), G. urAlensis (GU), And G. inflAtA (GI)] used by women As dietAry supplements for their Anti-inflAmmAtory Activities And their Ability to modulAte estrogen metAbolism. The pure compounds, liquiritigenin (LigF), its chAlcone isomer isoliquiritigenin (LigC), And the GI-specific LicochAlcone A (LicA) were Also tested. The licorice extrActs And compounds were evAluAted for Anti-inflAmmAtory Activity by meAsuring inhibition of iNOS Activity in mAcrophAge cells: GI ≫ GG > GU And LigC ≅ LicA ≫ LigF. The MichAel Acceptor chAlcone, LicA, is likely responsible for the Anti-inflAmmAtory Activity of GI. A sensitive LC-MS/MS AssAy wAs employed to quAntify estrogen metAbolism by meAsuring 2-MeOE1 As nontoxic And 4-MeOE1 As genotoxic biomArkers in the nontumorigenic humAn mAmmAry epitheliAl cell line, MCF-10A. GG, GU, And LigC increAsed 4-MeOE1, whereAs GI And LicA inhibited 2- And 4-MeOE1 levels. GG, GU (5 μg/mL), And LigC (1 μM) Also enhAnced P450 1B1 expression And Activities, which wAs further increAsed by inflAmmAtory cytokines (TNF-α And IFN-γ). LicA (1, 10 μM) decreAsed cytokine- And TCDD-induced P450 1B1 gene expression And TCDD-induced xenobiotic response element luciferAse reporter (IC50 = 12.3 μM), suggesting An AntAgonistic effect on the Aryl hydrocArbon receptor, which regulAtes P450 1B1. SimilArly, GI (5 μg/mL) reduced cytokine- And TCDD-induced P450 1B1 gene expression. Collectively, these dAtA suggest thAt, of the three licorice species thAt Are used in botAnicAl supplements, GI represents the most promising chemopreventive licorice extrAct for women's heAlth. AdditionAlly, the differentiAl effects of the GlycyrrhizA species on estrogen metAbolism emphAsize the importAnce of stAndArdizAtion of botAnicAl supplements to species-specific bioActive compounds.

  • DifferentiAl Effects of GlycyrrhizA Species on Genotoxic Estrogen MetAbolism: LicochAlcone A DownregulAtes P450 1B1, whereAs Isoliquiritigenin StimulAtes It
    2015
    Co-Authors: Tareisha L. Dunlap, Shuai Wang, Charlotte Simmler, Shaonong Chen, Birgit M Dietz, Guido F. Pauli, Judy L Bolton
    Abstract:

    Estrogen chemicAl cArcinogenesis involves 4-hydroxylAtion of estrone/estrAdiol (E1/E2) by P450 1B1, generAting cAtechol And quinone genotoxic metAbolites thAt cAuse DNA mutAtions And initiAte/promote breAst cAncer. InflAmmAtion enhAnces this effect by upregulAting P450 1B1. The present study tested the three AuthenticAted medicinAl species of licorice [GlycyrrhizA glAbrA (GG), G. urAlensis (GU), And G. inflAtA (GI)] used by women As dietAry supplements for their Anti-inflAmmAtory Activities And their Ability to modulAte estrogen metAbolism. The pure compounds, liquiritigenin (LigF), its chAlcone isomer isoliquiritigenin (LigC), And the GI-specific LicochAlcone A (LicA) were Also tested. The licorice extrActs And compounds were evAluAted for Anti-inflAmmAtory Activity by meAsuring inhibition of iNOS Activity in mAcrophAge cells: GI ≫ GG > GU And LigC ≅ LicA ≫ LigF. The MichAel Acceptor chAlcone, LicA, is likely responsible for the Anti-inflAmmAtory Activity of GI. A sensitive LC-MS/MS AssAy wAs employed to quAntify estrogen metAbolism by meAsuring 2-MeOE1 As nontoxic And 4-MeOE1 As genotoxic biomArkers in the nontumorigenic humAn mAmmAry epitheliAl cell line, MCF-10A. GG, GU, And LigC increAsed 4-MeOE1, whereAs GI And LicA inhibited 2- And 4-MeOE1 levels. GG, GU (5 μg/mL), And LigC (1 μM) Also enhAnced P450 1B1 expression And Activities, which wAs further increAsed by inflAmmAtory cytokines (TNF-α And IFN-γ). LicA (1, 10 μM) decreAsed cytokine- And TCDD-induced P450 1B1 gene expression And TCDD-induced xenobiotic response element luciferAse reporter (IC50 = 12.3 μM), suggesting An AntAgonistic effect on the Aryl hydrocArbon receptor, which regulAtes P450 1B1. SimilArly, GI (5 μg/mL) reduced cytokine- And TCDD-induced P450 1B1 gene expression. Collectively, these dAtA suggest thAt, of the three licorice species thAt Are used in botAnicAl supplements, GI represents the most promising chemopreventive licorice extrAct for women’s heAlth. AdditionAlly, the differentiAl effects of the GlycyrrhizA species on estrogen metAbolism emphAsize the importAnce of stAndArdizAtion of botAnicAl supplements to species-specific bioActive compounds

Guang Liang - One of the best experts on this subject based on the ideXlab platform.

  • LicochAlcone A inhibits the proliferAtion of humAn lung cAncer cell lines A549 And h460 by inducing g2 m cell cycle Arrest And er stress
    International Journal of Molecular Sciences, 2017
    Co-Authors: Tingting Zhang, Wenxin Zhang, Lina Zhou, Bin Yu, Wei Wang, Zhihong Yang, Guang Liang
    Abstract:

    : LicochAlcone A (LicA), A flAvonoid isolAted from the fAmous Chinese medicinAl herb GlycyrrhizA urAlensis Fisch, hAs wide spectrum of phArmAcologicAl Activities. In this study, the Anti-cAncer effects And potentiAl mechAnisms of LicA in non-smAll cell lung cAncer (NSCLC) cells were studied. LicA decreAsed cell viAbility And induced Apoptosis in A dose-dependent mAnner in NSCLC cells. LicA inhibited lung cAncer cells growth by blocking cell cycle progression At the G2/M trAnsition And inducing Apoptosis. LicA treAtment decreAsed the expression of MDM2, Cyclin B1, Cdc2 And Cdc25C in H460 And A549 cAncer cell lines. In Addition, LicA induced cAspAse-3 ActivAtion And poly-ADP-ribose polymerAse (PARP) cleAvAge, which displAyed feAtures of Apoptotic signAls. Furthermore, LicA increAsed the expression of endoplAsmic reticulum (ER) stress relAted proteins, such As p-EIF2α And ATF4. These dAtA provide evidence thAt LicA hAs the potentiAl to be used in the treAtment of lung cAncer.

  • LicochAlcone A Inhibits the ProliferAtion of HumAn Lung CAncer Cell Lines A549 And H460 by Inducing G2/M Cell Cycle Arrest And ER Stress
    MDPI AG, 2017
    Co-Authors: Chenyu Qiu, Tingting Zhang, Wenxin Zhang, Lina Zhou, Wei Wang, Zhihong Yang, Zhiguo Liu, Peng Zou, Guang Liang
    Abstract:

    LicochAlcone A (LicA), A flAvonoid isolAted from the fAmous Chinese medicinAl herb GlycyrrhizA urAlensis Fisch, hAs wide spectrum of phArmAcologicAl Activities. In this study, the Anti-cAncer effects And potentiAl mechAnisms of LicA in non-smAll cell lung cAncer (NSCLC) cells were studied. LicA decreAsed cell viAbility And induced Apoptosis in A dose-dependent mAnner in NSCLC cells. LicA inhibited lung cAncer cells growth by blocking cell cycle progression At the G2/M trAnsition And inducing Apoptosis. LicA treAtment decreAsed the expression of MDM2, Cyclin B1, Cdc2 And Cdc25C in H460 And A549 cAncer cell lines. In Addition, LicA induced cAspAse-3 ActivAtion And poly-ADP-ribose polymerAse (PARP) cleAvAge, which displAyed feAtures of Apoptotic signAls. Furthermore, LicA increAsed the expression of endoplAsmic reticulum (ER) stress relAted proteins, such As p-EIF2α And ATF4. These dAtA provide evidence thAt LicA hAs the potentiAl to be used in the treAtment of lung cAncer

Paulo Henrique Dias De ,carvalho - One of the best experts on this subject based on the ideXlab platform.

  • IsolAmento e identificAção dA licochAlconA A A pArtir dA GlycyrrhizA inflAtA e AvAliAção de suAs AtividAdes citotóxicA in vitro e hepAtoprotetorA em modelo de lesão hepáticA em rAtos
    Universidade Federal de Juiz de Fora, 2013
    Co-Authors: Paulo Henrique Dias De ,carvalho
    Abstract:

    A descobertA de protótipos nAturAis AssociAdA às metodologiAs de isolAmento e identificAção químicA de constituintes A pArtir de novAs fontes botânicAs, bem como dA AvAliAção dAs AtividAdes fArmAcológicAs e toxicológicAs dessAs moléculAs demonstrAm grAndes perspectivAs pArA o desenvolvimento rAcionAl de novos fármAcos. Tendo em vistA A AltA incidênciA de doençAs do fígAdo, no BrAsil e no mundo, e que existem poucos medicAmentos eficAzes e cApAzes de reverter ou reduzir A progressão destAs, o isolAmento e A identificAção de substânciAs com potenciAl hepAtoprotetor é, hoje, umA áreA promissorA nA buscA de novAs substânciAs bioAtivAs. TrAdicionAlmente, As rAízes de GlycyrrhizA sp., conhecidAs como licorice, são usAdAs nA medicinA AlternAtivA com inúmerAs finAlidAdes, dentre elAs hepAtoprotetorA. EntretAnto, Até o momento, não existem relAtos destA AtividAde vinculAdA à licochAlconA A, umA dAs substânciAs mAjoritáriAs nAs rAízes de GlycyrrhizA inflAtA. No presente trAbAlho AvAliArAm-se As AtividAdes dA licochAlconA A em ensAios de viAbilidAde celulAr dAs linhAgens de fibroblásto (NIH/3T3) e cArcinomA hepAtocelulAr humAno (HepG-2), Adesão celulAr de HepG-2 e em modelo de lesão hepáticA induzidA por ligAção do ducto biliAr (BDL) em rAtos WistAr. Além disso, desenvolveu-se umA metodologiA pArA determinAção dA licochAlconA A em CLAE-UV, utilizAndo colunA C18, fAse móvel em grAdiente de águA AcidificAdA (0,1% H3PO4) e metAnol (50:50 – 20:80 v/v), fluxo de 1,1 mL/min e comprimento de ondA pArA detecção em 372 nm. A licochAlconA A isolAdA A pArtir do extrAto seco dAs rAízes de G. inflAtA foi identificAdA por RMN 1H e 13C. O isolAmento Apresentou-se sAtisfAtório, bem como A metodologiA propostA pArA quAntificAção destA substânciA por CLAE-UV, que Apresentou excelente lineAridAde, precisão e exAtidão. Nos experimentos in vitro, A licochAlconA A não demonstrou redução significAtivA nA viAbilidAde dAs célulAs dA linhAgem HepG-2 (IC50 > 200 μM) e dA NIH/3T3 (IC50 > 100 μM), bem como no experimento de Adesão dAs célulAs HepG-2 (IC50 > 200 μM) (p>0,05). Estes dAdos corroborAm com Aqueles encontrAdos no experimento in vivo, no quAl A licochAlconA A (50 mg/Kg) tAmbém não Apresentou toxicidAde Ao fígAdo, já que os resultAdos encontrAdos não forAm significAtivAmente diferentes Aos do grupo controle (p>0,05). Contudo, elA tAmbém não demonstrou cApAcidAde de promover ou reduzir os dAnos hepáticos cAusAdo pelo BDL, no tempo de trAtAmento do estudo reAlizAdo (48 h).The nAturAl prototypes discovery AssociAted with methods of chemicAl constituents isolAtion And identificAtion from new botAnicAl sources, As well As the evAluAtion of phArmAcologicAl And toxicologicAl Activities of these molecules show greAt prospects for the new drugs rAtionAl development. In view of the high incidence of liver diseAse in BrAzil And the world, And there Are few effective drugs And Able to reverse or slow the progression of these diseAse, the substAnces isolAtion And identificAtion with potentiAl hepAtoprotective todAy is A promising AreA in seArch for new bioActive substAnces. TrAditionAlly, the roots of GlycyrrhizA sp., known As licorice, Are used in AlternAtive medicine with numerous purposes, Among them hepAtoprotective. However, to dAte, there Are no reports of this Activity linked to licochAlconA A, one mAjority of the substAnces in the roots of GlycyrrhizA inflAtA. In the present study evAluAted the Activities of LicochAlcone A in cell viAbility AssAys of strAins fibroblAst (NIH/3T3) And humAn hepAtocellulAr cArcinomA (HepG-2), cell Adhesion HepG-2 And model of liver injury induced by bile duct ligAtion (BDL) in WistAr rAts. In Addition, we developed A methodology for determining the LicochAlcone A quAntitAtive HPLC-UV, using C18 column And A mobile phAse grAdient of Acidified wAter (0.1% H3PO4) And methAnol (50:50 - 20:80 v/v), flow rAte of 1.1 mL/min And detection wAvelength At 372 nm. The LicochAlcone A isolAted from the dried extrAct of the roots of G. inflAtA wAs identified by 1H And 13C NMR. The isolAtion hAd to be sAtisfActory, As well As the proposed methodology for quAntificAtion of this substAnce by HPLC-UV, which showed excellent lineArity, reproducibility And AccurAcy. In in vitro experiments, LicochAlcone A showed no significAnt reduction in the viAbility of the cell line HepG-2 (IC50 > 200 μM) And NIH/3T3 (IC50 > 100 μM), As well As in cell Adhesion HepG-2 experiments (IC50 > 200 μM) (p> 0.05). These dAtA corroborAte those found in the in vivo experiment, in which the LicochAlcone A (50 mg/kg) Also showed no toxicity to the liver, since the results were not significAntly different to the control group (p>0.05). Nevertheless, it hAs not shown the Ability to promote or reduce liver dAmAge cAused by BDL, At the treAtment time of the study (48 h)

  • IsolAmento e identificAção dA licochAlconA A A pArtir dA GlycyrrhizA inflAtA e AvAliAção de suAs AtividAdes citotóxicA in vitro e hepAtoprotetorA em modelo de lesão hepáticA em rAtos
    'Revista Educacao em Foco (UFJF)', 2013
    Co-Authors: Paulo Henrique Dias De ,carvalho
    Abstract:

    The nAturAl prototypes discovery AssociAted with methods of chemicAl constituents isolAtion And identificAtion from new botAnicAl sources, As well As the evAluAtion of phArmAcologicAl And toxicologicAl Activities of these molecules show greAt prospects for the new drugs rAtionAl development. In view of the high incidence of liver diseAse in BrAzil And the world, And there Are few effective drugs And Able to reverse or slow the progression of these diseAse, the substAnces isolAtion And identificAtion with potentiAl hepAtoprotective todAy is A promising AreA in seArch for new bioActive substAnces. TrAditionAlly, the roots of GlycyrrhizA sp., known As licorice, Are used in AlternAtive medicine with numerous purposes, Among them hepAtoprotective. However, to dAte, there Are no reports of this Activity linked to licochAlconA A, one mAjority of the substAnces in the roots of GlycyrrhizA inflAtA. In the present study evAluAted the Activities of LicochAlcone A in cell viAbility AssAys of strAins fibroblAst (NIH/3T3) And humAn hepAtocellulAr cArcinomA (HepG-2), cell Adhesion HepG-2 And model of liver injury induced by bile duct ligAtion (BDL) in WistAr rAts. In Addition, we developed A methodology for determining the LicochAlcone A quAntitAtive HPLC-UV, using C18 column And A mobile phAse grAdient of Acidified wAter (0.1% H3PO4) And methAnol (50:50 - 20:80 v/v), flow rAte of 1.1 mL/min And detection wAvelength At 372 nm. The LicochAlcone A isolAted from the dried extrAct of the roots of G. inflAtA wAs identified by 1H And 13C NMR. The isolAtion hAd to be sAtisfActory, As well As the proposed methodology for quAntificAtion of this substAnce by HPLC-UV, which showed excellent lineArity, reproducibility And AccurAcy. In in vitro experiments, LicochAlcone A showed no significAnt reduction in the viAbility of the cell line HepG-2 (IC50 > 200 μM) And NIH/3T3 (IC50 > 100 μM), As well As in cell Adhesion HepG-2 experiments (IC50 > 200 μM) (p> 0.05). These dAtA corroborAte those found in the in vivo experiment, in which the LicochAlcone A (50 mg/kg) Also showed no toxicity to the liver, since the results were not significAntly different to the control group (p>0.05). Nevertheless, it hAs not shown the Ability to promote or reduce liver dAmAge cAused by BDL, At the treAtment time of the study (48 h).A descobertA de protótipos nAturAis AssociAdA às metodologiAs de isolAmento e identificAção químicA de constituintes A pArtir de novAs fontes botânicAs, bem como dA AvAliAção dAs AtividAdes fArmAcológicAs e toxicológicAs dessAs moléculAs demonstrAm grAndes perspectivAs pArA o desenvolvimento rAcionAl de novos fármAcos. Tendo em vistA A AltA incidênciA de doençAs do fígAdo, no BrAsil e no mundo, e que existem poucos medicAmentos eficAzes e cApAzes de reverter ou reduzir A progressão destAs, o isolAmento e A identificAção de substânciAs com potenciAl hepAtoprotetor é, hoje, umA áreA promissorA nA buscA de novAs substânciAs bioAtivAs. TrAdicionAlmente, As rAízes de GlycyrrhizA sp., conhecidAs como licorice, são usAdAs nA medicinA AlternAtivA com inúmerAs finAlidAdes, dentre elAs hepAtoprotetorA. EntretAnto, Até o momento, não existem relAtos destA AtividAde vinculAdA à licochAlconA A, umA dAs substânciAs mAjoritáriAs nAs rAízes de GlycyrrhizA inflAtA. No presente trAbAlho AvAliArAm-se As AtividAdes dA licochAlconA A em ensAios de viAbilidAde celulAr dAs linhAgens de fibroblásto (NIH/3T3) e cArcinomA hepAtocelulAr humAno (HepG-2), Adesão celulAr de HepG-2 e em modelo de lesão hepáticA induzidA por ligAção do ducto biliAr (BDL) em rAtos WistAr. Além disso, desenvolveu-se umA metodologiA pArA determinAção dA licochAlconA A em CLAE-UV, utilizAndo colunA C18, fAse móvel em grAdiente de águA AcidificAdA (0,1% H3PO4) e metAnol (50:50 – 20:80 v/v), fluxo de 1,1 mL/min e comprimento de ondA pArA detecção em 372 nm. A licochAlconA A isolAdA A pArtir do extrAto seco dAs rAízes de G. inflAtA foi identificAdA por RMN 1H e 13C. O isolAmento Apresentou-se sAtisfAtório, bem como A metodologiA propostA pArA quAntificAção destA substânciA por CLAE-UV, que Apresentou excelente lineAridAde, precisão e exAtidão. Nos experimentos in vitro, A licochAlconA A não demonstrou redução significAtivA nA viAbilidAde dAs célulAs dA linhAgem HepG-2 (IC50 > 200 μM) e dA NIH/3T3 (IC50 > 100 μM), bem como no experimento de Adesão dAs célulAs HepG-2 (IC50 > 200 μM) (p>0,05). Estes dAdos corroborAm com Aqueles encontrAdos no experimento in vivo, no quAl A licochAlconA A (50 mg/Kg) tAmbém não Apresentou toxicidAde Ao fígAdo, já que os resultAdos encontrAdos não forAm significAtivAmente diferentes Aos do grupo controle (p>0,05). Contudo, elA tAmbém não demonstrou cApAcidAde de promover ou reduzir os dAnos hepáticos cAusAdo pelo BDL, no tempo de trAtAmento do estudo reAlizAdo (48 h).CAPES - CoordenAção de AperfeiçoAmento de PessoAl de Nível SuperiorCNPq - Conselho NAcionAl de Desenvolvimento Científico e TecnológicoFAPEMIG - FundAção de AmpAro à PesquisA do EstAdo de MinAs GerAi

Birgit M Dietz - One of the best experts on this subject based on the ideXlab platform.

  • induction of nAd p h quinone oxidoreductAse 1 nqo1 by glycyrrhizA species used for women s heAlth differentiAl effects of the michAel Acceptors isoliquiritigenin And LicochAlcone A
    Chemical Research in Toxicology, 2015
    Co-Authors: Atieh Hajirahimkhan, Charlotte Simmler, Shaonong Chen, Guido F Pauli, Birgit M Dietz, Huali Dong, Daniel D Lantvit, Dejan Nikolic, Richard B Van Breemen, Judy L Bolton
    Abstract:

    For the AlleviAtion of menopAusAl symptoms, women frequently turn to botAnicAl dietAry supplements, such As licorice And hops. In Addition to estrogenic properties, these botAnicAls could Also hAve chemopreventive effects. We hAve previously shown thAt hops And its MichAel Acceptor xAnthohumol (XH) induced the chemoprevention enzyme, NAD(P)H:quinone oxidoreductAse 1 (NQO1), in vitro And in vivo. Licorice species could Also induce NQO1, As they contAin the MichAel Acceptors isoliquiritigenin (LigC) found in GlycyrrhizA glAbrA (GG), G. urAlensis (GU), G. inflAtA (GI), And LicochAlcone A (LicA) which is only found in GI. These licorice species And hops induced NQO1 Activity in murine hepAtomA (HepA1c1c7) cells; hops ≫ GI > GG ≅ GU. SimilAr to the known chemopreventive compounds curcumin (turmeric), sulforAphAne (broccoli), And XH, LigC And LicA were Active dose-dependently; sulforAphAne ≫ XH > LigC > LicA ≅ curcumin ≫ liquiritigenin (LigF). Induction of the AntioxidAnt response element luciferAse in humAn he...

  • differentiAl effects of glycyrrhizA species on genotoxic estrogen metAbolism LicochAlcone A downregulAtes p450 1b1 whereAs isoliquiritigenin stimulAtes it
    Chemical Research in Toxicology, 2015
    Co-Authors: Tareisha L Dunlap, Shuai Wang, Charlotte Simmler, Shaonong Chen, Guido F Pauli, Birgit M Dietz, Judy L Bolton
    Abstract:

    Estrogen chemicAl cArcinogenesis involves 4-hydroxylAtion of estrone/estrAdiol (E1/E2) by P450 1B1, generAting cAtechol And quinone genotoxic metAbolites thAt cAuse DNA mutAtions And initiAte/promote breAst cAncer. InflAmmAtion enhAnces this effect by upregulAting P450 1B1. The present study tested the three AuthenticAted medicinAl species of licorice [GlycyrrhizA glAbrA (GG), G. urAlensis (GU), And G. inflAtA (GI)] used by women As dietAry supplements for their Anti-inflAmmAtory Activities And their Ability to modulAte estrogen metAbolism. The pure compounds, liquiritigenin (LigF), its chAlcone isomer isoliquiritigenin (LigC), And the GI-specific LicochAlcone A (LicA) were Also tested. The licorice extrActs And compounds were evAluAted for Anti-inflAmmAtory Activity by meAsuring inhibition of iNOS Activity in mAcrophAge cells: GI ≫ GG > GU And LigC ≅ LicA ≫ LigF. The MichAel Acceptor chAlcone, LicA, is likely responsible for the Anti-inflAmmAtory Activity of GI. A sensitive LC-MS/MS AssAy wAs employed to...

  • differentiAl effects of glycyrrhizA species on genotoxic estrogen metAbolism LicochAlcone A downregulAtes p450 1b1 whereAs isoliquiritigenin stimulAtes it
    Chemical Research in Toxicology, 2015
    Co-Authors: Tareisha L Dunlap, Shuai Wang, Charlotte Simmler, Shaonong Chen, Guido F Pauli, Birgit M Dietz, Judy L Bolton
    Abstract:

    Estrogen chemicAl cArcinogenesis involves 4-hydroxylAtion of estrone/estrAdiol (E1/E2) by P450 1B1, generAting cAtechol And quinone genotoxic metAbolites thAt cAuse DNA mutAtions And initiAte/promote breAst cAncer. InflAmmAtion enhAnces this effect by upregulAting P450 1B1. The present study tested the three AuthenticAted medicinAl species of licorice [GlycyrrhizA glAbrA (GG), G. urAlensis (GU), And G. inflAtA (GI)] used by women As dietAry supplements for their Anti-inflAmmAtory Activities And their Ability to modulAte estrogen metAbolism. The pure compounds, liquiritigenin (LigF), its chAlcone isomer isoliquiritigenin (LigC), And the GI-specific LicochAlcone A (LicA) were Also tested. The licorice extrActs And compounds were evAluAted for Anti-inflAmmAtory Activity by meAsuring inhibition of iNOS Activity in mAcrophAge cells: GI ≫ GG > GU And LigC ≅ LicA ≫ LigF. The MichAel Acceptor chAlcone, LicA, is likely responsible for the Anti-inflAmmAtory Activity of GI. A sensitive LC-MS/MS AssAy wAs employed to quAntify estrogen metAbolism by meAsuring 2-MeOE1 As nontoxic And 4-MeOE1 As genotoxic biomArkers in the nontumorigenic humAn mAmmAry epitheliAl cell line, MCF-10A. GG, GU, And LigC increAsed 4-MeOE1, whereAs GI And LicA inhibited 2- And 4-MeOE1 levels. GG, GU (5 μg/mL), And LigC (1 μM) Also enhAnced P450 1B1 expression And Activities, which wAs further increAsed by inflAmmAtory cytokines (TNF-α And IFN-γ). LicA (1, 10 μM) decreAsed cytokine- And TCDD-induced P450 1B1 gene expression And TCDD-induced xenobiotic response element luciferAse reporter (IC50 = 12.3 μM), suggesting An AntAgonistic effect on the Aryl hydrocArbon receptor, which regulAtes P450 1B1. SimilArly, GI (5 μg/mL) reduced cytokine- And TCDD-induced P450 1B1 gene expression. Collectively, these dAtA suggest thAt, of the three licorice species thAt Are used in botAnicAl supplements, GI represents the most promising chemopreventive licorice extrAct for women's heAlth. AdditionAlly, the differentiAl effects of the GlycyrrhizA species on estrogen metAbolism emphAsize the importAnce of stAndArdizAtion of botAnicAl supplements to species-specific bioActive compounds.

  • DifferentiAl Effects of GlycyrrhizA Species on Genotoxic Estrogen MetAbolism: LicochAlcone A DownregulAtes P450 1B1, whereAs Isoliquiritigenin StimulAtes It
    2015
    Co-Authors: Tareisha L. Dunlap, Shuai Wang, Charlotte Simmler, Shaonong Chen, Birgit M Dietz, Guido F. Pauli, Judy L Bolton
    Abstract:

    Estrogen chemicAl cArcinogenesis involves 4-hydroxylAtion of estrone/estrAdiol (E1/E2) by P450 1B1, generAting cAtechol And quinone genotoxic metAbolites thAt cAuse DNA mutAtions And initiAte/promote breAst cAncer. InflAmmAtion enhAnces this effect by upregulAting P450 1B1. The present study tested the three AuthenticAted medicinAl species of licorice [GlycyrrhizA glAbrA (GG), G. urAlensis (GU), And G. inflAtA (GI)] used by women As dietAry supplements for their Anti-inflAmmAtory Activities And their Ability to modulAte estrogen metAbolism. The pure compounds, liquiritigenin (LigF), its chAlcone isomer isoliquiritigenin (LigC), And the GI-specific LicochAlcone A (LicA) were Also tested. The licorice extrActs And compounds were evAluAted for Anti-inflAmmAtory Activity by meAsuring inhibition of iNOS Activity in mAcrophAge cells: GI ≫ GG > GU And LigC ≅ LicA ≫ LigF. The MichAel Acceptor chAlcone, LicA, is likely responsible for the Anti-inflAmmAtory Activity of GI. A sensitive LC-MS/MS AssAy wAs employed to quAntify estrogen metAbolism by meAsuring 2-MeOE1 As nontoxic And 4-MeOE1 As genotoxic biomArkers in the nontumorigenic humAn mAmmAry epitheliAl cell line, MCF-10A. GG, GU, And LigC increAsed 4-MeOE1, whereAs GI And LicA inhibited 2- And 4-MeOE1 levels. GG, GU (5 μg/mL), And LigC (1 μM) Also enhAnced P450 1B1 expression And Activities, which wAs further increAsed by inflAmmAtory cytokines (TNF-α And IFN-γ). LicA (1, 10 μM) decreAsed cytokine- And TCDD-induced P450 1B1 gene expression And TCDD-induced xenobiotic response element luciferAse reporter (IC50 = 12.3 μM), suggesting An AntAgonistic effect on the Aryl hydrocArbon receptor, which regulAtes P450 1B1. SimilArly, GI (5 μg/mL) reduced cytokine- And TCDD-induced P450 1B1 gene expression. Collectively, these dAtA suggest thAt, of the three licorice species thAt Are used in botAnicAl supplements, GI represents the most promising chemopreventive licorice extrAct for women’s heAlth. AdditionAlly, the differentiAl effects of the GlycyrrhizA species on estrogen metAbolism emphAsize the importAnce of stAndArdizAtion of botAnicAl supplements to species-specific bioActive compounds

  • Induction of NAD(P)H:Quinone OxidoreductAse 1 (NQO1) by GlycyrrhizA Species Used for Women’s HeAlth: DifferentiAl Effects of the MichAel Acceptors Isoliquiritigenin And LicochAlcone A
    2015
    Co-Authors: Atieh Hajirahimkhan, Charlotte Simmler, Shaonong Chen, Guido F Pauli, Huali Dong, Daniel D Lantvit, Dejan Nikolić, Richard B. Van Breemen, Birgit M Dietz
    Abstract:

    For the AlleviAtion of menopAusAl symptoms, women frequently turn to botAnicAl dietAry supplements, such As licorice And hops. In Addition to estrogenic properties, these botAnicAls could Also hAve chemopreventive effects. We hAve previously shown thAt hops And its MichAel Acceptor xAnthohumol (XH) induced the chemoprevention enzyme, NAD­(P)­H:quinone oxidoreductAse 1 (NQO1), in vitro And in vivo. Licorice species could Also induce NQO1, As they contAin the MichAel Acceptors isoliquiritigenin (LigC) found in GlycyrrhizA glAbrA (GG), G. urAlensis (GU), G. inflAtA (GI), And LicochAlcone A (LicA) which is only found in GI. These licorice species And hops induced NQO1 Activity in murine hepAtomA (HepA1c1c7) cells; hops ≫ GI > GG ≅ GU. SimilAr to the known chemopreventive compounds curcumin (turmeric), sulforAphAne (broccoli), And XH, LigC And LicA were Active dose-dependently; sulforAphAne ≫ XH > LigC > LicA ≅ curcumin ≫ liquiritigenin (LigF). Induction of the AntioxidAnt response element luciferAse in humAn hepAtomA (HepG2-ARE-C8) cells suggested involvement of the KeAp1-Nrf2 pAthwAy. GG, GU, And LigC Also induced NQO1 in nontumorigenic breAst epitheliAl MCF-10A cells. In femAle SprAgue–DAwley rAts treAted with GG And GU, LigC And LigF were detected in the liver And mAmmAry glAnd. GG weAkly enhAnced NQO1 Activity in the mAmmAry tissue but not in the liver. TreAtment with LigC Alone did not induce NQO1 in vivo most likely due to its conversion to LigF, extensive metAbolism, And its low bioAvAilAbility in vivo. These dAtA show the chemopreventive potentiAl of licorice species in vitro could be due to LigC And LicA And emphAsize the importAnce of chemicAl And biologicAl stAndArdizAtion of botAnicAls used As dietAry supplements. Although the in vivo effects in the rAt model After four-dAy treAtment Are minimAl, it must be emphAsized thAt menopAusAl women tAke these supplements for extended periods of time And long-term beneficiAl effects Are quite possible

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  • isolAtion And identificAtion of flAvonoids in licorice And A study of their inhibitory effects on tyrosinAse
    Journal of Agricultural and Food Chemistry, 2005
    Co-Authors: Xiaoru Wang, Frank S C Lee, Shufen Cui
    Abstract:

    Five different flAvonoids were isolAted from licorice After multistep chromAtogrAphic frActionAtion. The Aim wAs to identify And chArActerize Active components in licorice responsible for Antibrowning Activities And to seek new tyrosinAse inhibitors for ApplicAtions As Antibrowning And depigmenting Agents in the food And cosmetic industries. The isolAted flAvonoids were identified As liquiritin, licurAside, isoliquiritin, liquiritigenin (from GlycyrrhizA urAlensis Fisch.), And LicochAlcone A (from GlycyrrhizA inflAte BAt.) by UV, MS, (1)H NMR, And (13)C NMR AnAlyses. The inhibitory potencies And cApAcities of these flAvonoids towArd monophenolAse Activity of mushroom tyrosinAse were investigAted. The IC(50) vAlues of licurAside, isoliquiritin, And LicochAlcone A for monophenolAse Activity were 0.072, 0.038, And 0.0258 mM, respectively. A study of the mechAnisms of monophenolAse inhibition by these flAvonoids indicAted thAt they Are All competitive inhibitors. Different from the Above flAvonoids, no inhibitory Activity wAs observed for liquiritin, whereAs liquiritigenin ActivAted the monophenolAse Activity As A cofActor. The inhibitory effect of licurAside, isoliquiritin, And LicochAlcone A on diphenolAse Activity with l-DOPA As the substrAte wAs much lower thAn those with l-tyrosine. Results suggest thAt licurAside, isoliquiritin, And LicochAlcone A hAve the high potentiAl to be further developed into effective Antibrowning And depigmenting Agents.

  • isolAtion And purificAtion of inflAcoumArin A And LicochAlcone A from licorice by high speed counter current chromAtogrAphy
    Journal of Chromatography A, 2004
    Co-Authors: Qiaoe Wang, Frank S C Lee, Xiaoru Wang
    Abstract:

    AbstrAct High-speed counter-current chromAtogrAphy (HSCCC) technique in semi-prepArAtive scAle hAs been Applied to isolAte And purify bioActive flAvone compounds from the ethAnol extrAct of GlycyrrhizA inflAtA BAt., A pArticulAr plAnt species of licorice. HSCCC sepArAtion wAs performed with A two-phAse solvent system composed of n -hexAne–chloroform–methAnol–wAter (5:6:3:2, v/v) by eluting the lower mobile phAse At A flow rAte of 1.8 ml/min And A revolution speed of 800 rpm. PurificAtion wAs performed with A two-phAse solvent system composed of n -hexAne–chloroform–methAnol–wAter (1.5:6:3:2, v/v) by eluting the lower mobile phAse At A flow-rAte of 1.5 ml/min And A revolution speed of 800 rpm. Two mAjor flAvone peAks: inflAcoumArin A And LicochAlcone A were collected And the respective yields of the peAks Amount to 6 mg (8.6%, w/w) And 8 mg (11.4%, w/w) from 70 mg of the crude extrAct sAmple. The purities of inflAcoumArin A And LicochAlcone A reAched 99.6% And 99.1%, respectively, After A sequentiAl purificAtion run. The structures of inflAcoumArin A And LicochAlcone A were positively confirmed by 1 H NMR And 13 C NMR, 1 H– 13 C-COSY, UV, FT-IR And electron ionizAtion MS AnAlyses.