• 제목/요약/키워드: Liquiritigenin

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The Memory-Enhancing Effects of Liquiritigenin by Activation of NMDA Receptors and the CREB Signaling Pathway in Mice

  • Ko, Yong-Hyun;Kwon, Seung-Hwan;Hwang, Ji-Young;Kim, Kyung-In;Seo, Jee-Yeon;Nguyen, Thi-Lien;Lee, Seok-Yong;Kim, Hyoung-Chun;Jang, Choon-Gon
    • Biomolecules & Therapeutics
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    • 제26권2호
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    • pp.109-114
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    • 2018
  • Liquiritigenin (LQ) is a flavonoid that can be isolated from Glycyrrhiza radix. It is frequently used as a tranditional oriental medicine herbal treatment for swelling and injury and for detoxification. However, the effects of LQ on cognitive function have not been fully explored. In this study, we evaluated the memory-enhancing effects of LQ and the underlying mechanisms with a focus on the N-methyl-D-aspartic acid receptor (NMDAR) in mice. Learning and memory ability were evaluated with the Y-maze and passive avoidance tests following administration of LQ. In addition, the expression of NMDAR subunits 1, 2A, and 2B; postsynaptic density-95 (PSD-95); phosphorylation of $Ca^{2+}$/calmodulin-dependent protein kinase II (CaMKII); phosphorylation of extracellular signal-regulated kinase 1/2 (ERK 1/2); and phosphorylation of cAMP response element binding (CREB) proteins were examined by Western blot. In vivo, we found that treatment with LQ significantly improved memory performance in both behavioral tests. In vitro, LQ significantly increased NMDARs in the hippocampus. Furthermore, LQ significantly increased PSD-95 expression as well as CaMKII, ERK, and CREB phosphorylation in the hippocampus. Taken together, our results suggest that LQ has cognition enhancing activities and that these effects are mediated, in part, by activation of the NMDAR and CREB signaling pathways.

Identification of 3'-Hydroxymelanetin and Liquiritigenin as Akt Protein Kinase Inhibitors

  • Yang Hye-Young;Lee Hong-Sub;Ko Jong-Hee;Yeon Seung-Woo;Kim Tae-Yong;Hwang Bang-Yeon;Kang Sang-Sun;Chun Jae-Sun;Hong Soon-Kwang
    • Journal of Microbiology and Biotechnology
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    • 제16권9호
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    • pp.1384-1391
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    • 2006
  • The signal transduction system is one of the most important devices involved in maintaining life, and many protein kinases are included in the cellular signal transduction system. Finding a protein kinase inhibitor is very valuable, as it can be used to study cell biology and applied to pharmaceuticals. For the efficient and rapid screening of protein kinase inhibitors, two assay systems were combined; the nonradioactive protein kinase assay system that uses an FITC-labeled IRS-2 peptide and the cell-based paper disc assay system that uses Streptomyces griseus as the indicator strain. Among 330 kinds of herb extracts tested, the extract of Dalbergia odorifera exhibited the strongest inhibitory activity in the two assay systems and was selected for further isolation. Based on solvent extraction and many steps of chromatography, seven compounds were finally separated to homogeneity and their structures determined by $^{1}H$ and $^{13}C$ NMR spectroscopies. Four were to be flavonoids and identified as butin ($C_{15}H_{12}O_5$, Mw=272.07), 3'-hydroxymelanetin ($C_{16}H_{12}O_6$, Mw=300.06), liquiritigenin ($C_{15}H_{12}O_4$, Mw=256.07), and 2'-hydroxyformononetin ($C_{16}H_{12}O_{5}$, Mw=284.07). 3'-Hydroxymelanetin inhibited the phosphorylation of the GSK3 protein by Akt to 37% at a concentration of $10{\mu}g/ml$ and showed the strongest cytotoxicity ($ED_{50}<50{\mu}g/ml$) against the human cancer cell line HCT116. Under the same conditions, liquiritigenin also inhibited the phosphorylation of GSK3 by Akt to 26%, and its cytotoxicity against the HCT116 cell line was lower than $100{\mu}g/ml$.

감초로부터 항균활성 물질의 분리 및 구조 동정 (Isolation and Identification of Antimicrobial Active Substance from Glycyrrhiza uralensis FISCH)

  • 안은영;신동화;백남인;오진아
    • 한국식품과학회지
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    • 제30권3호
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    • pp.680-687
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    • 1998
  • 감초(Glycyrrhiza uralensis FISCH) 75% 에탄올 추출물이 L. monocytogenes 5 균주에 대하여 뚜렷한 항균 활성이 인정되어 용매 분획한 후 활성이 높은 에틸아세테이트 분획물을 얻었고 이를 silica gel column chromatography로 연속으로 2회 정제하여 황색 분말의 항균 활성 소획분을 분리하였다. 활성 소획분은 L. monocytogenes에 대해서는 $10{\sim}50\;ppm$ 수준에서 증식억제 효과를 보였고 50 및 100 ppm 농도에서는 살균 효과가 인정되었으며 S. aureus에 대해서는 $30{\sim}50\;ppm$ 수준에서 증식억제 효과를 보였으며 E. coli에 대해서는 100 ppm 농도에서도 증식억제 효과가 전혀 나타나지 않았다. IR, $^1H-NMR$$^{13}C-NMR$로 기기분석하여 활성 획분의 구조를 분석한 결과 감초에 함유된 flavanone 화합물의 하나인 liquiritigenin으로 동정되었다.

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유산균 발효에 의한 소청룡탕의 발효 전 후 성분 변화 연구 (Analysis of Constituents in Socheongryong-tangs Fermented by Lactic acid bacteria)

  • 양민철;김동선;정상원;마진열
    • 한국한의학연구원논문집
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    • 제17권3호
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    • pp.115-121
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    • 2011
  • Objective : The purpose of this study was to investigate the changes in the contents of constituents in Socheongryong-tang (CY) and its fermentations (FCY) with 10 species of lactic acid bacteria. Methods : Ten strains of lactic acid bacteria, Lactobacillus casei 127, L. acidophilus 128, L. casei 129, L. plantarum 144, L. amylophilus 161, L. curvatus 166, L. delbruekil subsp. lactis 442, L. casei 693, B. breve 744, and B. thermophilum 748, were used for the fermentation of Socheongryong-tang. The increased and decreased constituents were identified using HPLC/DAD and various liquid chromatographic techniques, and the structure was elucidated using NMR and MS. These compounds were quantitatively analyzed using an HPLC/DAD system. Results : The increased constituents were identified to be liquiritigenin (1) and cinnamyl alcohol (2), and the decreased constituent was determined to be liquiritin (3). Liquiritigenin (1) and cinnamyl alcohol (2) were increased in all of the FCYs, while liquiritin (3) was decreased. The fermentation of the ten lactic acid bacteria demonstrated that the decomposable rate of these three compounds in FCYs were different. Socheongryong-tang fermented by L. plantarum 144 and L. amylophilus 161 showed the most remarkable changes. Conclusions : CY could be increased antibacterial, neuroprotective, or antiinflammatory effect by fermentation with lactic acid bacteria, especially with L. plantarum and L. amylophilus, considering their known biological activities. In addition, it is expected that this study will help to establish quality control parameters for FCY.

잎새버섯 균사체를 이용한 감초추출발효물의 플라보노이드 생성과 항염 활성 연구 (Production of Flavonoid Compounds and Anti-inflammatory Property of Fermented Licorice Extract with the Basidiomycete Grifola frondosa HB0071)

  • 배준태;송민현;김진화;이근수;표형배
    • 대한화장품학회지
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    • 제38권4호
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    • pp.327-338
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    • 2012
  • 리퀴리티게닌과 이소리퀴리티게닌은 감초의 주요 플라보노이드 성분이다. 이들 플라보노이드는 수용성 감초 추출물과 ${\beta}$-glucosidase를 생성하는 잎새버섯 HB0071 균사체 발효배양을 통하여 생산하였다. 감초추출물 내 리퀴리티게닌과 이소리퀴리티게닌은 잎새버섯 발효배양 동안 현저히 증가하였다. 이 균주의 ${\beta}$-glucosidase의 활성은 배양 96시간을 기준으로 최고 91.5 mU/mL로 확인되었으며, 감초추출발효물로부터 생성된 리퀴리티게닌과 이소리퀴리티게닌의 함량은 HPLC 분석을 통하여 최대 $568.5{\mu}g/mL$$89.6{\mu}g/mL$로 확인되었다. 본 연구에서는 감초추출물의 잎새버섯 발효 전 후의 시료가 처리된 각질형성세포를 이용하여 자외선 UVB에 조사로 발현된 염증유발인자(COX-2)와 사이토카인(IL-$1{\beta}$, IL-6) 모두 감초추출발효물(FLEx)에서 농도의존적으로 발현이 억제되는 것을 확인하였다. 결론적으로 리퀴리티게닌과 이소리퀴리티게닌의 함량이 증가된 감초추출발효물은 자외선으로부터 손상된 피부 염증반응을 완화시켜줄 것으로 사료된다.

발효법제에 의한 감초의 Flavonoid 무배당체의 생산 (Production of Flavonoid Aglycone from Korean Glycyrrhizae Radix by Biofermentation Process)

  • 나인수;박민주;노종훈;민진우;방면호;양덕춘
    • 동의생리병리학회지
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    • 제22권3호
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    • pp.569-574
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    • 2008
  • The GUE6 was isolated from ethyl acetate fraction of Glycyrrhiza uralensis and confirmed as liquiritin. Liquiritin(LQ) treated with ${\beta}$-glucosidase from plant(Prunus dulcis) and bacteria(Lactobacillus pentosus) crude enzymes. The ${\beta}$-glucosidase activities of crude enzymes were 229.8 U/g(Prunus dulcis) and 19.17 U/ml(Lactobacillus pentosus), respectively. Liquiritin(LQ) biotransformed into liquiritigenin(LQG) by ${\beta}$-glucosidase from crude enzymes. The EtOAc fraction(GUE6) and the converted product were identified as liquiritin and liquiritigenin, by TLC chromatogram, $^{1}H$-NMR and $^{13}C$-NMR.

Screening of Bioconversion Components from Gumiganghwal-tang on Fermentation by Lactobacillus Strains

  • Liang, Chun;Lee, Kwang Jin;Cho, Chang-Won;Ma, Jin Yeul
    • Natural Product Sciences
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    • 제20권2호
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    • pp.102-106
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    • 2014
  • Gumiganghwal-tang (GMT) is a traditional herbal prescription used for treatment of the common cold, pain, and inflammatory diseases. Variations in the amounts of bioactive components of GMT and GMT fermented with 10 Lactobacillus strains were investigated by high-performance liquid chromatography coupled with diode array detection (HPLC-DAD). Simultaneous qualitative and quantitative analyses of eleven bioactive compounds (prim-O-glucosylcimifugin, liquiritin, cimifugin, baicalin, liquiritigenin, wogonoside, baicalein, wogonin, butylphthalide, imperatorin, and isoimperatorin) were performed, with comparison of their retention times (tR) and UV spectra with those of standard compounds. The amounts of baicalin (8.71 mg/g), liquiritigenin (5.28 mg/g) and butylphthalide (5.10 mg/g) were the major compounds in GMT. We found that L. fermentum KFRI 145 fermented wogonoside and baicalin to their aglycones, wogonin and baicalein, respectively. These results indicated that L. fermentum KFRI 145 has potential as a functional starter culture for manufacturing fermented GMT.

Isolation of Flavonoids from Processed Aconiti Tuber

  • Lyu, Ha-Na;Kwak, Ho-Young;Lee, Dae-Young;Kim, Kyong-Tai;Kim, Se-Young;Baek, Nam-In
    • Journal of Applied Biological Chemistry
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    • 제51권4호
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    • pp.165-168
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    • 2008
  • A processed Aconiti tuber (Korean name, Kyeong-Po Buja) was extracted with 80% aqueous EtOH, and the concentrated extract was partitioned with EtOAc and water ($H_2O$). From the EtOAc fraction, two flavonoids were isolated through repeated silica gel column chromatographies. From the result of physico-chemical data including NMR, mass spectrometry and IR, the chemical structures of the compounds were determined to be liquiritin (1) and liquiritigenin (2). This is the first study to isolate flavonoids (1) and (2) from the processed Aconiti tuber.

LC-MS/MS를 이용한 향사육군자탕의 주요성분의 함량분석 (Quantitative Analysis of Hyangsayukgunja-Tang Using an Ultra-Performance Liquid Chromatography Coupled to Electrospray Ionization Tandem Mass Spectrometry)

  • 서창섭;신현규
    • 생약학회지
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    • 제46권4호
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    • pp.352-364
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    • 2015
  • The aim of this study was to quantitatively analyze for quality assessment of eighteen marker compounds, including homogentisic acid, 3,4-dihydroxybenzaldehyde, spinosin, liquiritin, hesperidin, ginsenoside Rg1, liquiritigenin, ginsenoside Rb1, glycyrrhizin, 6-gingerol, atractylenolide III, honokiol, costunolide, dehydrocostuslactone, atractylenolide II, nootkatone, magnolol, and atractylenolide I, in Hyangsayukgunja-tang using an ultra-performance liquid chromatography-electrospray ionization-mass spectrometer. The column for separation of eighteen marker components were used a UPLC BEH $C_{18}$ analytical column ($2.1{\times}100mm$, $1.7{\mu}$) and kept at $45^{\circ}C$ by gradient elution with 0.1% (v/v) formic acid in water and acetonitrile as mobile phase. The flow rate and injection volume were 0.3 mL/min and $2.0{\mu}l$, respectively. The correlation coefficient of all marker compounds was ${\geq}0.9914$, which means good linearity, within the test ranges. The limits of detection and quantification values of the all analytes were in the ranges 0.04-1.11 and 0.13-3.33 ng/mL, respectively. As a result, five compounds, homogentisic acid, 3,4-dihydroxybenzaldehyde, spinosin, liquiritigenin, and atractylenolide I, in this sample were not detected and the amounts of the 13 compounds except for the 5 compounds were $8.10-6736.37{\mu}g/g$ in Hyangsayukgunja-tang extract.

구강편평세포암종 세포에서 감초 유래 Liquiritigenin의 항증식, 세포주기 정지 및 세포사멸 유도 (Anti-proliferation, Cell Cycle Arrest, and Apoptosis Induced by Natural Liquiritigenin from Licorice Root in Oral Squamous Cell Carcinoma Cells)

  • 곽아원;윤구;채정일;심정현
    • 생명과학회지
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    • 제29권3호
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    • pp.295-302
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    • 2019
  • Liquiritigenin (LG)은 licorice 뿌리에서 분리된 chiral flavonoid이다. LG는 항산화, 항암 및 항염증 효과를 포함하여 다양한 생물학적 활성을 가지고 있다. 구강편평세포암종에서 LG의 항암 활성은 아직 밝혀지지 않았다. 본 연구에서는 구강편평상피암 세포(HN22)에서 LG의 항암 효능을 시험하였다. HN22 세포에 LG를 처리하여 MTT 분석으로 세포 생존율을 평가하였으며, Annecin V/7-Aminactinomycin D 염색, 세포주기 및 Multi-caspase 활성을 $Muse^{TM}$ cell Analyzer로 분석하여 세포사멸 유도를 확인하였다. 분석결과, 구강편평상피암 HN22 세포에 LG를 처리시 G2/M 세포주기 정지를 일으켰으며, Western blotting 통하여 cyclin B1 및 CDC2 발현 감소와 p27 발현 증가를 확인하였다. LG는 활성산소종의 생성을 유발하고, CCAAT/enhancer-binding protein homologous protein (CHOP) 및 78-kDa glucose regulated protein (GRP78)의 발현을 농도의존적으로 유도하였다. HN22 세포에 LG의 처리는 미토콘드리아 막전위의 손실(${\Delta}{\Psi}m$)을 일으켰다. LG를 처리한 HN22 세포의 단백질 분석결과 apoptotic protease activating factor-1 (Apaf-1), cleaved Poly (ADP-Ribose) Polymerase (C-PARP) 및 Bax의 발현을 증가함을 확인하였다. 따라서 우리의 결과는 LG이 구강편평상피암 세포의 세포사멸을 유도하여 항암제 역할을 할 수 있는 천연 화합물임을 시사한다.