• Title/Summary/Keyword: EtOAc fraction

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Isolation of ${\beta}-sitosterol$, Phytol and Zingerone $4-O-{\beta}-D-glucopyranoside$ from Chrysanthemum Boreale Makino

  • Kim, Dong-Hyun;Bang, Myun-Ho;Song, Myoung-Chong;Kim, Soon-Un;Chang, Young-Jin;Baek, Nam-In
    • Korean Journal of Medicinal Crop Science
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    • v.13 no.5
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    • pp.284-287
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    • 2005
  • The flowers of Chrysanthemum boreale Makino were extracted with 80% aqueous MeOH, and the concentrated extract was partitioned with n-hexane, EtOAc, n-BuOH and $H_2O$. Two compounds from the n-hexane fraction and one glucoside from the n-BuOH fraction were isolated through the repeated silica gel and ODS column chromatographies. From the result of physico-chemical data including NMR, MS and IR, the chemical structures of the compounds were determined as ${\beta}-sitosterol$ (1), phytol (2) and zingerone $4-O-{\beta}-D-glucopyranoside$ (3). Compounds 2 and 3 were isolated for the first time from this plant.

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

  • Na, In-Su;Park, Min-Ju;Noh, Chong-Hoon;Min, Jin-Woo;Bang, Myun-Ho;Yang, Deok-Chun
    • Journal of Physiology & Pathology in Korean Medicine
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    • v.22 no.3
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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.

Anti-inflammatory effects of ethanol extract from Orostachys japonicus on modulation of signal pathways in LPS-stimulated RAW 264.7 cells

  • Jeong, Jae-Han;Ryu, Deok-Seon;Suk, Dong-Hee;Lee, Dong-Seok
    • BMB Reports
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    • v.44 no.6
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    • pp.399-404
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    • 2011
  • In this study, powder of Orostachys japonicus A. Berger (O. japonicus) was extracted with 95% ethyl alcohol and fractionated using a series of organic solvents, including n-hexane (hexane), dichloromethane (DCM), ethylacetate (EtOAc), n-butanol (BuOH), and water ($H_2O$). We investigated the anti-inflammatory effects of these O. japonicus extracts on lipopolysaccharide (LPS)-stimulated RAW 264.7 cells. Their effects on the expression of inflammatory mediators and transcription factors were analyzed by Western blotting. DCM fraction significantly inhibited formation of reactive oxygen species (ROS) as well as nitric oxide (NO) in LPS-stimulated RAW 264.7 cells. Phosphorylation of the pro-inflammatory transcription factor complex nuclear factor-kappa B (NF-${\kappa}$B) p65 and expression of inducible nitric oxide synthase (iNOS), one of its downstream proteins, were also suppressed by DCM fraction. These effects were regulated by upsteam proteins in the mitogen-activated protein kinase (MAPK) and phosphoinositide 3-kinase/Akt (PI3K/Akt) signaling pathways. Taken together, our data suggest that O. japonicus could be used as a potential source for anti-inflammatory agents.

Anti-invasive Activity against Cancer Cells of Phytochemicals in Red Jasmine Rice (Oryza sativa L.)

  • Pintha, Komsak;Yodkeeree, Supachai;Pitchakarn, Pornsirit;Limtrakul, Pornngarm
    • Asian Pacific Journal of Cancer Prevention
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    • v.15 no.11
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    • pp.4601-4607
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    • 2014
  • Red rice contains pharmacological substances including phenolics, oryzanol, tocotrienol and tocopherol. Recently, red rice extract has been employed as a source of antioxidants for inhibition of tumor growth. This study was carried out to evaluate the anti-invasion effects of red rice extract fractions on cancer cells. It was found that at $100{\mu}g/ml$ of crude ethanolic extract (CEE), hexane fraction (Hex) and dichloromethane fraction (DCM) could reduce HT1080 and MDA-MB-231 cancer cell invasion. Hex and DCM revealed higher potency levels than CEE, whereas an ethyl acetate fraction (EtOAc) had no effect. Gelatin zymography revealed that Hex decreased the secretion and activity of matrix metalloproteinase-2 and -9 (MMP-2 and-9). In contrast, the DCM fraction exhibited slightly effect on MMPs secretion and had no effect on MMPs activity. Collagenase activity was significantly inhibited by the Hex and DCM fractions. High amounts of ${\gamma}$-oryzanol and ${\gamma}$-tocotrienol were found in the Hex and DCM fractions and demonstrated an anti-invasion property. On the other hand, proanthocyanidin was detected only in the CEE fraction and reduced MDA-MB-231 cells invasion property. These observations suggest that proanthocyanidin, ${\gamma}$-oryzanol and ${\gamma}$-tocotrienol in the red rice fractions might be responsible for the anti invasion activity. The red rice extract may have a potential to serve as a food-derived chemotherapeutic agent for cancer patients.

Studies on the Chemical Constituents Biological Activities of Mulberry Extracts (오디(Mulberry) 추출물의 성분분석 및 생리활성에 관한 연구)

  • Lee, Sang-Keug;Lee, Hak-Ju;Kang, Ha-Youg;Choi, Don-Ha;Jo, Hyun-Jin;Lee, Tae-Seong
    • Journal of the Korean Wood Science and Technology
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    • v.37 no.1
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    • pp.105-113
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    • 2009
  • The freezed Mulberry (10 kg) was extracted with 80% EtOH, concentrated, and fractionated with a series of n-hexane, ethyl acetate, and water on a separatory funnel. A portion of ethyl acetate soluble (22 g) was chromatographed on a Sephadex LH-20 column using a series of aqueous methanol as eluents. The isolated compounds were identified by cellulose TLC, $^1H-$,$^{13}C$-NMR, FAB, and EI-MS. Quercetin-3-O-${\beta}$-D-glucopyranoside (Compound I), protocatechuic acid (Compound II), p-hydroxybenzoic acid (Compound III) were isolated from the ethyl acetate soluble fraction. In antioxidative activities of the fractionated extractives using DPPH radical scavenging test, EtOAc and water soluble fractions indicated better than BHT as contro and in in vitro tests using MTT assay, there was no cytotoxicity. Also, tyrosinase inhibition and anticancer activities were not so good, but there may be a potential as a cosmetic raw material because the cell extension effect was excellent.

Isolation of Compounds with Antioxidative Activity from Quickly Fermented Soy-Based Foods

  • Jang, Mi-Young;Cho, Jeong-Yong;Cho, Jeong-Il;Moon, Jae-Hak;Park, Keun-Hyung
    • Food Science and Biotechnology
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    • v.15 no.2
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    • pp.214-219
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    • 2006
  • A bacterial strain, initially identified as B1-3, was isolated from cheonggukjang, a traditional Korean dish made from fermented soybeans. Using the Biolog system and 16S rRNA sequence analysis, we identified B1-3 as Bacillus mojavensis. We manufactured a quickly fermented soybean (QFS) food product using the B. mojavensis, and guided by their 1,1-diphenyl-2-picrylhydrazyl (DPPH) radical-scavenging ability. We isolated substances with antioxidative activity from it. Using mass spectrometry (MS) and nuclear magnetic resonance (NMR) techniques, we isolated 4 compounds from the ethyl acetate (EtOAc)-soluble neutral fraction of methyl alcohol (MeOH) extracts of the QFS food product (genistein, daidzein, 3R,4R-3-methyl-3,4-dihydroxy-2-pentanone, and 3S,4R-3-methyl-3,4-dihydroxy-2-pentanone) and 3 compounds from its acidic fraction (4-hydroxyphenylacetic acid, genistin, and daidzein). Two compounds from the neutral fraction (3R,4R-3-methyl-3,4-dihydroxy-2-pentanone and 3S,4R-3-methyl-3,4-dihydroxy-2-pentanone) were not detected in nonfermented soybeans (NFS) or in the filtrate of the LB broth used to culture B. mojavensis. However, they were detected in the filtrate of the same broth when it contained 2% glucose. These results suggest that these 2 compounds were derived from glucose (or other saccharides) in the soybean during fermentation. One compound that was found in the acidic fraction (4-hydroxyphenylacetic acid) was readily detected in NFS, but not in the culture broth. This suggests that 4-hydroxyphenylacetic acid was derived from NFS. We concluded that the antioxidative activity of cheonggukjang is a result of the interactions between soybean components and the microorganisms used in the fermentation of cheonggukjang.

Glycosyl flavones from Humulus japonicus suppress MMP-1 production via decreasing oxidative stress in UVB irradiated human dermal fibroblasts

  • Nam, Eui Jeong;Yoo, Gyhye;Lee, Joo Young;Kim, Myungsuk;Jhin, Changho;Son, Yang-Ju;Kim, Sun Young;Jung, Sang Hoon;Nho, Chu Won
    • BMB Reports
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    • v.53 no.7
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    • pp.379-384
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    • 2020
  • Exposure to Ultraviolet (UV) light induces photoaging of skin, leading to wrinkles and sunburn. The perennial herb Humulus japonicus, widely distributed in Asia, is known to have anti-inflammatory, antimicrobial, and antioxidant effects. However, the physiological activities of isolated compounds from H. japonicus have rarely been investigated. This study focused on the isolation of active compounds from H. japonicus and the evaluation of their effects on photoaging in UVB-irradiated human fibroblast (Hs68) cells. When the extract and four fractions of H. japonicus were treated respectively in UVB-irradiated Hs68 cells to investigate anti-photoaging effects, the ethyl acetate (EtOAc) fraction showed the strongest inhibitory effect on MMP1 secretion. From EtOAc fraction, we isolated luteolin-8-C-glucoside (1), apigenin-8-C-glucoside (2), and luteolin-7-O-glucoside (3). These compounds suppressed UVB-induced MMP-1 production by inhibiting the phosphorylation of the mitogen-activated protein kinases (MAPKs) and activator protein-1 (AP-1). When the antioxidant activity of the compounds were estimated by conducting western blot, calculating the bond dissociation energies of the O-H bond (BDE) at different grade, and measuring radical scavenging activity, we found luteolin-8-C-glucoside (1) showed the strongest activity on the suppression of UVB-induced photoaging. These results demonstrate the inhibitory effect of three flavone glycosides derived from H. japonicus on MMP-1 production, MAPK and AP-1 signaling, and oxidative stress; this could prove useful in suppressing UVB induced photoaging.

Anti-Inflammatory Activity of Three Kinds of Salvia and Its Active Compounds (3종의 배암차즈기에 대한 염증억제 활성 비교 및 활성성분 구명)

  • Shin, Han Jae;Gwak, Hyo Min;Jang, Mi;Park, Si Hwan;Min, Hye Jeong;Lee, Jeong Min;Lee, Moon Yong;Kim, Jong Han;Kim, Sung Won;Han, Chang Kyun;Kim, Seung Hyung
    • Korean Journal of Medicinal Crop Science
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    • v.24 no.5
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    • pp.401-407
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    • 2016
  • Background: Salvia has been widely cultivated for use in flavoring and folk medicines in many countries, including Korea and China. In this study, we investigated the anti-inflammatory activity and the underlying active compounds of Salvia extract and its fractions. Methods and Results: The anti-inflammatory activity was measured by assessing the inhibition of cysteinyl leukotriene production in rat basophilic leukemia (RBL)-2H3 mast cells. Salvia plebeia R. Br. was found to have the most potent inhibitory activity on leukotriene production than S. japonica and S. chanroenica had. Fifty percent ethanol extracts of S. plebeia R. Br. were successively partitioned with n-hexane, methylene chloride, ethyl acetate, 1-butanol and water. The ethyl acetate (EtOAc) fraction showed stronger anti-inflammatory activity than other solvent fractions did. The EtOAc fraction was subjected to silica gel column chromatography elution with a chloroform and methanol gradient system (100 : 1 ${\rightarrow}$ 1 : 1) yielding 10 fractions. Three kinds of fractions (chloroform:methanol = 20 : 1, 10 : 1 and 5 : 1) showed high inhibitory activity on leukotriene production. We confirmed the major compounds with anti-inflammatory activity from S. plebeia R. Br. Conclusions: In this study, the major components of S. plebeia that showed leukotriene production inhibitory activity were isolated using solvent extraction and silica gel column chromatography. Rosmarinic acid, hispidulin and luteolin were identified as the major compounds with anti-inflammatory effect.

Cytotoxicity of steroid-saponins from the tuber of Liriope platyphylla W. T. (맥문동(Liriope platyphylla W. T.) 스테로이드 사포닌의 항암활성)

  • Cho, Sung-Ji;Bang, Myun-Ho;Lee, In-Ja;Park, Chang-Gi;Kim, Moo-Sung;Kim, Keum-Sook;Sung, Jae-Duk;Baek, Nam-In
    • Applied Biological Chemistry
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    • v.41 no.5
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    • pp.390-394
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    • 1998
  • The tuber of Liriope platyphylla was extracted with 80% aqueous MeOH and solvent-fractionated with EtOAc, n-BuOH and $H_2O$. Evaluation of growth inhibitory activity of each fractions on various carcinoma cells, A549, SK-OV-3, SK-Mel-2, XF-498 and HCT-15, indicated the n-BuOH fraction to be the highest in the activity. From the fraction, two saponin compounds were isolated through Amberlite XAD-II and silica gel column chromatographies, repeatedly, and their chemical structures were elucidated as spicatoside A and B by interpretation of spectral data, NMR and IR, and adaptation of acid hydrolysis. Spicatoside A showed growth inhibitory activity on carcinoma cells, and the $IC_{50}$ values against A549, SK-OV-3, SK-Mel-2, XF-498 and HCT-15 cells were determined to be 17.3, 21.7, 14.9, 18.8 and $15.6\;{\mu}g/ml$, respectively.

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Antioxidation and Antigenotoxic Effects of Buckwheat Sprout Extracts (메밀싹 추출물의 항산화 효과 및 유전독성억제 효과)

  • Kim, Su-Hyun;Lee, Eue-Yong;Ham, Seung-Si
    • Journal of the Korean Society of Food Science and Nutrition
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    • v.36 no.8
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    • pp.955-959
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    • 2007
  • This study was carried out to determine the antioxidative and antigenotoxic effects of buckwheat (Fagopyrum esculentum Moench) sprout using 1,1-diphenyl-2-picrylhydrazyl (DPPH) radical donating method and micronucleus test. Buckwheat sprout were extracted with 70% ethanol and then further fractionated to n-hexane, chloroform, ethyl acetate (EtOAc), butanol and water. Among the five fractions, the EtOAc fraction showed the highest electron donating activity ($RC_{50}$ 26.1 ${\mu}g/mL$). The effects of buckwheat sprout extracts on the frequencies of micronucleated polychromatic erythrocytes (MNPCEs) induced by MNNG (N-methyl-N'-nitro-N-nitrosoguanidine) were investigated in the bone marrow. 10, 20, 40 and 80 mg/kg of each extract were administered to animals immediately after injection of MNNG and the exposure time was 36 hrs. Inhibition effects of buckwheat sprout ethanol extract were 23.4%, 40.6%, 56.3% and 73.4%, respectively. When the fraction of hexane, chloroform, ethyl acetate, butanol and water from 70% ethanol extract were treated with concentration of 80 mg/kg, the suppression rates of the MNPCE were 64.1, 67.9, 75.8, 74.2 and 63.3%, respectively.