- 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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- 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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- Cloning and functional characterization of a chalcone isomerase from trigonella foenum-graecum L
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Flavonoids belong to a group of plant natural products with variable phenolic structures and play important roles in protection against biotic and abiotic stress. Fenugreek (Trigonella foenum-graecum L.) seeds and stems contain flavonol glycosides and isoflavone derivatives. Up to now, the molecular features of fenugreek flavonoid biosynthesis have not been characterized. Here we present cloning of a cDNA encoding a chalcone isomerase (namely TFGCHI1) from the leaves of T. foenum-graecum which convert chalcones to flavanones in vitro. Transformation of Arabidopsis loss-of-function tt5 (chi) mutant with a TFGCHI1 cDNA complemented tt5 and produced higher levels of flavonol glycosides than wild-type Col-0. Georg Thieme Verlag KG Stuttgart · New York.
- Qin, Jian-Chun,Zhu, Lin,Gao, Ming-Jun,Wu, Xian,Pan, Hong-Yu,Zhang, Yan-Sheng,Li, Xiang
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Read Online
- Design, synthesis, and cholinesterase inhibition assay of liquiritigenin derivatives as anti-Alzheimer's activity
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The marine environment is a rich resource for discovering functional materials, and seaweed is recognized for its potential use in biology and medicine. Liquiritigenin has been isolated and identified from Sargassum pallidum. To find new anti-Alzheimer's activity, we designed and synthesized thirty-two 7-prenyloxy-2,3-dihydroflavanone derivatives (3a-3p) and 5-hydroxy-7-prenyloxy-2,3-dihydro-flavanone derivatives (4a-4p) as cholinesterases inhibitors based on liquiritigenin as the lead compound. Inhibition screening against acetylcholinesterase (AChE) and butyrylcholinesterase (BuChE) indicated that all synthesized compounds possessed potent AChE inhibitory activity and moderated to weak BuChE inhibitory activity in vitro. Kinetic studies demonstrated that compound 4o inhibited AChE via a dual binding site ability. In addition, all compounds displayed the radical scavenging effects. Finally, the molecular docking simulation of 4o in AChE active site displayed good agreement with the obtained the pharmacological results.
- Guan, Liping,Jia, Jinjing,Jiang, Haiying,Peng, Dingxin,Zhang, Li
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supporting information
(2021/10/01)
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- Synthesis and studies of flavone and bis-flavone derivatives
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Flavonoids are widely occurring polyphenols of plant origin and well explored in the field of pharmacological activities. Recent studies showed this scaffold to be more dynamic as fluorescent probe. Very rare reports are there in literature on flavones as liquid crystals, for the first time we have synthesized and characterized flavone and bis-flavone derivatives for mesomorphic properties. Compounds 9a–d and 13a–d were studied for liquid crystalline properties by Differential scanning calorimetry (DSC) and Polarizing optical microscopy (POM) studies. The compounds 8, 9a–d, 12, and 13a–d were also studied for antioxidant property by DPPH assay.
- Durgapal, Sunil Dutt,Soman, Shubhangi S.,Umar, Shweta,Balakrishnan, Suresh
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supporting information
p. 2502 - 2510
(2020/07/07)
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- A method of synthesizing the glycyrrhizin (by machine translation)
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The invention relates to a synthetic chemical method of glycyrrhizin. In order to 2, 4 - dihydroxy acetophenone and 4 - hydroxy benzoic acid ethyl ester as the raw material, the protective group for a hydroxyl, keto ester condensation, cyclization and hyd
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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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- METHOD FOR PRODUCING LIQUIRITIGENIN PRECURSOR
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PROBLEM TO BE SOLVED: To provide a method which is suitable as a mass production method of liquiritigenin. SOLUTION: Provided is a method for producing liquiritigenin, comprising: synthesizing and crystallizing a trialkoxy-isoliquiritigenin represented by a formula (iii) by coupling a 4-alkoxycinnamic acid represented by a formula (i) and a 1,3-alkoxybenzene represented by a formula (ii) by a Friedel-Craft reaction (A); and eliminating a protective group to obtain isoliquiritigenin represented by a formula (iv). The isoliquiritigenin represented by a formula (iv) is administered in a body as a precursor of liquiritigenin represented by a formula (v), which is converted to a (-) form of liquiritigenin in the body. COPYRIGHT: (C)2016,JPOandINPIT
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Paragraph 0011
(2016/11/24)
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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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- In vitro and in vivo synergistic interaction of substituted chalcone derivatives with norfloxacin against methicillin resistant Staphylococcus aureus
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Thirty chalcone derivatives were synthesized via a base catalyzed Claisen Schmidt condensation and evaluated for their anti-methicillin-resistant Staphylococcus aureus (MRSA) activity alone and in combination with norfloxacin. Among these, 5 derivatives namely trans-3-(1H-indol-3-yl)-1-(4′-benzyloxyphenyl)-2-propen-1-one (2), 1-(4″-biphenyl)-3-(3′4′-dihydroxyphenyl)-2-propen-1-one (11), 1-(4″-hydroxy-3″-methylphenyl)3-(4′-hydroxyphenyl)-2-propen-1-one (14), 3-(4′-chlorophenyl)-1-(4″-hydroxyphenyl)2-propen-1-one (17), and LTG-oxime (27) showed significant antibacterial activity with MIC 12.5-50 g mL-1 respectively. In combination studies, derivatives 2 and 14 significantly reduced the MIC of norfloxacin by up to 16 fold (FICI 0.5), while derivatives 11, 17 and 27 reduced it by up to eight fold (FICI ≤ 0.5). Flow cytometry analysis results clearly indicated that derivatives 2 and 14 significantly promote the accumulation and inhibition of the Et-Br efflux, which was further validated through spectrofluorimeter using clinical isolate MRSA-ST2071. In systemically infected Swiss albino mice model, both the compounds significantly (P 0.001, P 0.01) lowered the systemic bacterial load in blood, liver, kidney, lung and spleen tissues. This study supports the promising use of chalcones in the development of economical antibacterial combinations.
- Gaur, Rashmi,Gupta, Vivek Kumar,Pal, Anirban,Darokar, Mahendra Padurang,Bhakuni, Rajendra Singh,Kumar, Brijesh
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p. 5830 - 5845
(2015/03/05)
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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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- Synthesis of oxygenated 4-arylisoflavans and 4-arylflavans
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Oxygenated 4-arylisoflavans and 4-heteroarylisoflavans were synthesized in good yields via BF3·OEt2 catalyzed arylation reactions of 4′,7-diacetoxyisoflavan-4-ol 8 with activated aryl and heteroaryl compounds. These reactions were found to produce stereoselectively the trans isomers. Similar reactions of 4′,7-diacetoxyflavan-4-ol 16 afforded the corresponding 4-arylflavans and 4-heteroarylflavans as mixtures of cis/trans isomers.
- Deodhar, Mandar,Wood, Kasey,Black, David Stc,Kumar, Naresh
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p. 6697 - 6700,4
(2012/12/13)
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- Synthesis of oxygenated 4-arylisoflavans and 4-arylflavans
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Oxygenated 4-arylisoflavans and 4-heteroarylisoflavans were synthesized in good yields via BF3·OEt2 catalyzed arylation reactions of 4′,7-diacetoxyisoflavan-4-ol 8 with activated aryl and heteroaryl compounds. These reactions were found to produce stereoselectively the trans isomers. Similar reactions of 4′,7-diacetoxyflavan-4-ol 16 afforded the corresponding 4-arylflavans and 4-heteroarylflavans as mixtures of cis/trans isomers.
- Deodhar, Mandar,Wood, Kasey,Black, David Stc,Kumar, Naresh
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p. 6697 - 6700
(2013/01/15)
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- An efficient catalytic synthesis of flavanones under green conditions
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An efficient and "green" catalytic conversion of 2′-hydroxychalcones to flavanones in 15 min in the presence of a simple amino acid and a base at room temperature is reported. Liquiritigenin was also efficiently synthesised under these conditions.
- Jiang, Heyan,Zheng, Xuxu,Yin, Zhongyi,Xie, Jingjing
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experimental part
p. 220 - 221
(2011/07/29)
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- Synthesis and antitumoractivity of liquiritigenin thiosemicarbazone derivatives
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In an attempt to develop potent and selective antitumor agents,a series of liquiritigenin thio-semicarbazone derivatives were designed and synthesized. The cytotoxicities of these compounds were evaluated in vitro against K562,DU-145,SGC-7901,HCT-116 and Hela cell lines. The pharmacological results showed that most of the prepared compounds displayed excellent selective cytotoxicity toward K562 and DU-145 cells. From the structureeactivity relationships we may conclude that the introduction of a thiosemicarbazone functional group at the 4-position in the skeleton of liquiritigenin is associated with an increase in cytotoxicity.
- Hu, Kun,Yang, Ze-Hua,Pan, Sha-Sha,Xu, Hua-Jin,Ren, Jie
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experimental part
p. 3453 - 3458
(2010/08/13)
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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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- Synthesis of (±)Abyssinone I and related compounds: Their anti-oxidant and cytotoxic activities
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An efficient and facile synthesis of naturally occurring prenylated flavonoids and their analogs have been described. Abyssinone I (9a) was prepared by condensing 2,2-dimethyl chrom-3-en-6-carboxaldehyde (5a) with protected resacetophenone under phase transfer conditions followed by deprotection and cyclization. The influence of prenyl group on anti-oxidant and cytotoxic activities was studied. The presence of 3′-prenyl group as in 8c enhanced radical scavenging activity but decreased reducing power activity when compared to non-prenylated analog 8f. In vitro testing in MCF-7 cell line revealed that prenylated chalcones and flavanones showed better inhibitory activity than their non-prenylated counterparts. Abyssinone I and its chalcone though exhibited negligible anti-oxidant activity their cytotoxic activities were comparable with other prenylated analogs.
- Rao, Gudapati Venkateswara,Swamy, Badrappa Narayana,Chandregowda, Venkateshappa,Reddy, G. Chandrasekara
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experimental part
p. 2239 - 2245
(2009/09/08)
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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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- Acid catalyzed stereoselective rearrangement and dimerization of flavenes: synthesis of dependensin
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Appropriately substituted flavenes undergo stereoselective rearrangement and dimerization when treated with methanolic hydrochloric acid to give benzopyranobenzopyrans. A rationale for the rearrangement is proposed. This synthetic methodology has been used for a high yield synthesis of the natural product dependensin.
- Deodhar, Mandar,Black, David StC,Kumar, Naresh
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p. 5227 - 5235
(2008/02/01)
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- A new synthesis of flavonoids via Heck reaction
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Several naturally occuring flavonoids have been synthesised following a new proposed method based on the use of the Heck reaction. The key step involves the coupling of an aryl vinyl ketone with an aryl iodide. This procedure affords the flavonoid moiety in a single step.
- Bianco, Armandodoriano,Cavarischia, Claudia,Farina, Angela,Guiso, Marcella,Marra, Carolina
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p. 9107 - 9110
(2007/10/03)
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- Peroxidase from cell cultures of cassia didymobotrya: A review and comparison with horseradish peroxidase
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The catalytic activity on flavonoids and dibenzylbutanolides and the specificity of the peroxidase isolated from 29d-old cell cultures of Cassia didymobotrya are reported. Studies on several substrates in comparison with horseradish peroxidase revealed pe
- Botta, Bruno,Ricciardi, Paola,Vitali, Alberto,Vinciguerra, Vittorio,Garcia, Carlos,Delle Monache, Giuliano
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p. 757 - 766
(2007/10/03)
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- An improved procedure for flavanones
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Trifluoroacetic acid is found to be an efficient reagent for the isomerisation of chalcones to flavanones.
- Chaturvedi, R.,Patil, P. N.,Mulchandani, N. B.
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p. 340 - 341
(2007/10/02)
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- Syntheses of Flavonoids via the Isoxazoline Route
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Syntheses of naturally occuring 7-hydroxyflavonone, liquiritigenin and the corresponding chalcones (isoliquiritigenin) are described.
- Almtorp, Gunvor T.,Bachmann, Torben L.,Torsell, Kurt B. G.
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p. 212 - 215
(2007/10/02)
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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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- A Convient Synthesis of Polyhydroxylated Chalcones and Flavanones
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A convenient route has been described for the synthesis of polyhydroxy chalcones and flavanones involving demethylation of their methyl ethers with pyridinium bromide.
- Ahluwalia, Vinod K.,Khanduri, Chandra H.,Mehta, Vimal D.,Sharma, Narain D.
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- Cyclization of Substituted 2'-Hydroxychalcones to Flavanones. Solvent and Isotope Effects
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The kinetic isotope effects on the cyclization of substituted 2'-hydroxychalcones (R=3-hydroxy, 4'-hydroxy, 4,4'-dihydroxy, 4'-hydroxy-4-nitro, 4-nitro, or 5'-methyl) into the corresponding substituted flavanones have been measured in water and/or methanol.The pronounced isotope effects observed are consistent with the slow rupture of a bond to hydrogen.The effect of the medium permittivity on the rate of cyclization of 2'-hydroxy, 2',4-dihydroxy-, and 2',4'-dihydroxychalcones have been also studied in several mixed solvents and the observed dependence is consistent with a reaction between one ion and one dipole.These results confirm a mechanism that involves general acid attack of the ionized form of the 2'-hydroxychalcones, concerted rotation through the CO-Cα bond, and annelation to the flavanone.
- Furlong, Jorge J. P.,Nudelman, N. Sbarbati
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p. 1213 - 1218
(2007/10/02)
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- FLAVONOID GLYCOSIDES OF THE ROOTS OF GLYCYRRHIZA URALENSIS
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The structure of a flavanone glycoside from the roots of Glycyrrhiza uralensis has been confirmed as 4'-O- 2)-β-D-glucopyranosyl>liquiritigenin.In addition, two known flavonoid glucosides, ononin (a minor component) and liquiritin (a major component) were isolated from the same extract. - Key Word Index - Glycyrrhiza uralensis; Leguminosae; licorice roots; water extract; flavonoid glycosides; ononin; liquiritin; 4'-O-2)-β-D-glucopyranosyl>liquiritigenin.
- Nakanishi, Tsutomu,Inada, Akira,Kambayashi, Kazuko,Yoneda, Kaisuke
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p. 339 - 342
(2007/10/02)
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- Chalaurenol: a Novel Product from Enzymic Oxidation of 2',4,4'-Trihydroxychalcone
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Peroxidase enzymes from various sources convert 2',4,4'-trihydroxychalcone (1) into the novel quinol ether of 2-formyl-6-hydroxycoumaranone (6), the structure of which was determined by X-ray diffraction; a biosynthetic pathway is suggested and capillarisin (11) may arise by a similar route.
- Begley, Michael J.,Crombie, Leslie,London, Martin,Savin, John,Whiting, Donald A.
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p. 1319 - 1321
(2007/10/02)
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- New Syntheses of 4',7-Dihydroxy-6,8-di-C-prenylflavanone, Bavachin, Isobavachin and Related Compounds
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The titel compounds have been synthesised by nuclear prenylation of 4',7-dihydroxyflavanone(liquiritigenin, III), Cyclodehydrogenation of bavachin and isobavachin with DDQ yields the chromenoflavanones (VIII) and (X) respectively which on dehydrogenation
- Krishnamurti, M.,Parthasarathi, J.
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p. 247 - 248
(2007/10/02)
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