- Liquiritigenin inhibits hepatic fibrogenesis and TGF-β1/Smad with Hippo/YAP signal
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Background: Recent reports highlighted the possibility that Yes-associated protein (YAP) and transforming growth factor-β1 (TGF-β1) can act as critical regulators of hepatic stellate cells (HSCs) activation; therefore, it is natural for compounds targeting Hippo/YAP and TGF-β1/Smad signaling pathways to be identified as potential anti-fibrotic candidates. Purpose: Liquiritigenin (LQ) is an aglycone of liquiritin and has been reported to protect the liver from injury. However, its effects on the Hippo/YAP and TGF-β1/Smad pathways have not been identified to date. Methods: We conducted a series of experiments using CCl4-induced fibrotic mice and cultured LX-2 cells. Result: LQ significantly inhibited liver fibrosis, as indicated by decreases in regions of hepatic degeneration, inflammatory cell infiltration, and the intensity of α-smooth muscle actin (α-SMA) staining in mice. Moreover, LQ blocked the TGF-β1-induced phosphorylation of Smad 3, and the transcript levels of plasminogen activator inhibitor-1 (PAI-1) and matrix metalloproteinase-2 (MMP-2) in LX-2 cells, which is similar with resveratrol and oxyresveratrol (positive controls). Furthermore, LQ increased activation of large tumor suppressor kinase 1 (LATS1) with the induction of YAP phosphorylation, thereby preventing YAP transcriptional activity and suppressing the expression of exacerbated TGF-β1/Smad signaling molecules. Conclusion: These results clearly show that LQ ameliorated experimental liver fibrosis by acting on the TGF-β1/Smad and Hippo/YAP pathways, indicating that LQ has the potential for effective treatment of liver fibrosis.
- Lee, Eun Hye,Park, Kwang-Il,Kim, Kwang-Youn,Lee, Ju-Hee,Jang, Eun Jeong,Ku, Sae Kwang,Kim, Sang Chan,Suk, Ho Young,Park, Ji Young,Baek, Su Youn,Kim, Young Woo
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- Identification of metabolites of liquiritin in rats by UHPLC-Q-TOF-MS/MS: Metabolic profiling and pathway comparison: In vitro and in vivo
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Liquiritin (LQ), the main bioactive constituent of licorice, is a common flavoring and sweetening agent in food products and has a wide range of pharmacological properties, including antidepressant-like, neuroprotective, anti-cancer and anti-inflammatory properties. This study investigated the metabolic pathways of LQ in vitro (rat liver microsomes) and in vivo (rat model) using ultra high-performance liquid chromatography coupled with hybrid triple quadrupole time-of-flight mass spectrometry (UHPLC-Q-TOF-MS/MS). Moreover, supplementary tools such as key product ions (KPIs) were employed to search for and identify compounds. As a result, 56 in vivo metabolites and 15 in vitro metabolites were structurally characterized. Oxidation, reduction, hydrolysis, methylation, acetylation, and sulfate and glucuronide conjugation were determined to be the major metabolic pathways of LQ, and there were differences in LQ metabolism in vitro and in vivo. In addition, the in vitro and in vivo metabolic pathways were compared in this study.
- Zhang, Xia,Liang, Caijuan,Yin, Jintuo,Sun, Yupeng,Zhang, Lantong
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p. 11813 - 11827
(2018/04/05)
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- METHOD FOR PRODUCING LIQUIRITIGENIN PRECURSOR
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An objective of this invention is to provide a mass manufacturing method for providing liquiritigenin by a proper method. The present invention provides a method for producing isoliquiritigenin by bringing a 4-alkoxy cinnamic acid represented by formula (I) and a 1,3-alkoxybenzene represented by formula (II) into Friedel-Crafts reaction (A) for coupling to a trialkoxy isoliquiritigenin represented by a synthesis formula (III) and allowing it to be crystal, and removing protection group to obtain an isoliquiritigenin represented by formula (IV), wherein, an in situ liquiritigenin (-) pharmacological effect is obtained by administrating the isoliquiritigenin represented by formula (IV)as a precursor of liquiritigenin into body.
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- MICROBIAL PRODUCTION OF THE FLAVONOIDS GARBANZOL, RESOKAEMPFEROL AND FISETIN
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The invention provides a genetically modified micro-organism comprising one or more transgene for the production of one or more of the flavonoids garbanzol, resokaempferol and fisetin. The micro-organism may be a bacterial or yeast cell engineered to express a metabolic pathway for garbanzol, resokaempferol and/or fisetin biosynthesis. The invention further provides a method for producing garbanzol, resokaempferol and/or fisetin employing the genetically modified micro-organism of the invention. The genetically modified micro- organism may be used to convert a number of substrates and/or co-substrates into fisetin via a fisetin biosynthetic pathway.
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Page/Page column 39; 40
(2016/06/01)
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- Highly efficient and green synthesis of flavanones and tetrahydroquinolones
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Highly efficient and green catalytic conversion of 2′-hydroxy and 2′-amino chalcones to flavanones and tetrahydroquinolones is reported herein. 2′-Hydroxy and 2′-amino chalcones can be almost completely converted to flavanones and tetrahydroquinolones in just 2 min in the presence of piperidine and KOH under room temperature. Liquiritigenin is also efficiently synthesized under similar conditions.
- Zheng, Xuxu,Jiang, Heyan,Xie, Jingjing,Yin, Zhongyi,Zhang, Haidong
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p. 1023 - 1029
(2013/03/13)
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- Flavone synthase II (CYP93B16) from soybean (Glycine max L.)
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Flavonoids are a very diverse group of plant secondary metabolites with a wide array of activities in plants, as well as in nutrition and health. All flavonoids are derived from a limited number of flavanone intermediates, which serve as substrates for a variety of enzyme activities, enabling the generation of diversity in flavonoid structures. Flavonoids can be characteristic metabolites, like isoflavonoids for legumes. Others, like flavones, occur in nearly all plants. Interestingly, there exist two fundamentally different enzymatic systems able to directly generate flavones from flavanones, flavone synthase (FNS) I and II. We describe an inducible flavone synthase activity from soybean (Glycine max) cell cultures, generating 7,4′-dihydroxyflavone (DHF), which we classified as FNS II. The corresponding full-length cDNA (CYP93B16) was isolated using known FNS II sequences from other plants. Functional expression in yeast allowed the detailed biochemical characterization of the catalytic activity of FNS II. A direct conversion of flavanones such as liquiritigenin, naringenin, and eriodictyol into the corresponding flavones DHF, apigenin and luteolin, respectively, was demonstrated. The enzymatic reaction of FNS II was stereoselective, favouring the (S)- over the (R)-enantiomer. Phylogenetic analyses of the subfamily of plant CYP93B enzymes indicate the evolution of a gene encoding a flavone synthase which originally catalyzed the direct conversion of flavanones into flavones, via early gene duplication into a less efficient enzyme with an altered catalytic mechanism. Ultimately, this allowed the evolution of the legume-specific isoflavonoid synthase activity.
- Fliegmann, Judith,Furtw?ngler, Katarina,Malterer, Georg,Cantarello, Corrado,Schüler, G?de,Ebel, Jürgen,Mith?fer, Axel
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experimental part
p. 508 - 514
(2010/06/17)
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- Composition Comprising Liquiritigenin for Preventing and Treating Liver Disease
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The present invention is related to a composition comprising an extract of licorice or liquiritigenin isolated therefrom significantly decrease the blood concentration of LDH and ALT enzyme, central necrosis and inflammation in acetaminophen-induced hepat
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- LIQUIRITIGENIN AND DERIVATIVES AS SELECTIVE ESTROGEN RECEPTOR BETA AGONISTS
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The disclosure provides compositions comprising liquiritigenin, or derivatives, or prodrugs, useful as estrogen receptor beta selective agonists. The disclosure also provides methods of treating menopausal symptoms, and estrogen-dependent disorders, with
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- Neolicuroside - a New Chalcone Glycoside from the Roots of Glycyrrhiza glabra
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Licuroside (1), first isolated by Litvinenko from the roots of Glycyrrhiza glabra, is not a homogeneous compound.It is separated into two isomeric glycosides 1 and 2 using modern chromatographic techniques (HPLC, LPLC).The structure of 2 is confirmed as isoliquiritigenin-4-β-D-apiofuranosyl-2''-β-D-glucopyranoside.So far 2 has not been described.The name neolicuroside is proposed.The structure of 1 is established as isoliquirtigenin-4'-β-D-apiofuranosyl-2''-β-D-glucopyranoside by spectroscopic methods.
- Miething, Holger,Speicher-Brinker, Annette
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p. 141 - 143
(2007/10/02)
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- FLAVONOID GLUCOSIDES FROM LICORICE
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Two new flavanone glycosides, liquiritigenin 4'-apiosyl(1->2)-glucoside and liquiritigenin 7,4'-diglucoside together with a known flavone, apigenin 6,8-di-C-glucoside, have been isolated from licorice.Key Word Index- Glycyrrhiza uralensis; Leguminosae; li
- Yahara, Shoji,Nishioka, Itsuo
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p. 2108 - 2109
(2007/10/02)
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