• Title/Summary/Keyword: naringenin $7-O-{\beta}-D-glucopyranoside$

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Constituents of Cudrania tricuspidata in Korea (한국산 꾸지 뽕나무의 성분)

  • Park, Jong-Cheol;Young, Han-Suk;Choi, Jae-Sue
    • YAKHAK HOEJI
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    • v.36 no.1
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    • pp.40-45
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    • 1992
  • Four flavonoids have been isolated from the leaves and stems of Cudrania tricuspidata Bureau (Moraceae) in Korea. They were kaempferol and kaempferol $7-O-{\beta}-D-glucopyranoside$ from the leaves, and kaempferide $7-O-{\beta}-D-glucopyranoside$ and naringenin $7-O-{\beta}-D-glucopyranoside$ from the stem respectively. The structures were established by spectroscopic and chemical methods.

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A Study on the Extractives of Domestic Major Softwood Needles(I) - Antioxidant Activity of the Extractives from the Needles of Abies koreana Maximowicz and Abies holophylla Wilson - (국내산 주요 침엽수 잎의 추출성분(I) - 구상나무(Abies koreana Maximowicz)와 전나무(Abies holophylla Wilson) 잎 추출성분의 항산화 활성 -)

  • Lee, Sang-Keug;Choi, Don-Ha;Bae, Young-Soo
    • Journal of the Korean Wood Science and Technology
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    • v.34 no.3
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    • pp.73-83
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    • 2006
  • The dried needles (1.5 kg) of Abies koreana and Abies holophylla were ground, extracted with acetone-$H_2O$ (7:3, v/v), concentrated, and fractionated with a series of hexane, methylene chloride, ethyl acetate and water on a separatory funnel. Each fraction was freeze dried, then a portion of ethyl acetate soluble powder was chromatographed on a Sephadex LH-20 column using a series of aqueous methanol and ethanol-hexane mixture as eluents. The isolated compounds were identified by cellulose TLC, $^1H$, $^{13}C-NMR$, COSY, HETCOR, FAB and EI-MS. The needles of Abies koreana and Abies holophylla contained a large amount of aromadendrin-7-O-${\beta}$-D-glucopyranoside (compound III), polydatin (compound VI), (-)-rhododendrol-2-O-${\beta}$-D-glucopyranoside (compound VII), in addition to a small amount of (+)-catechin (compound I), kaempferol-3-O-${\beta}$-D-glucopyranoside (compound IV), myricetin-3-O-${\beta}$-D-glucopyranoside (compound V), naringenin-7-O-${\beta}$-D-glucopyranoside (compound II). DPPH analysis was also tested to investigate the antioxidative effects on the isolated compounds and (+)-catechin and polydatin were effective.

A Novel Benzoyl Glucoside and Phenolic Compounds from the Leaves of Camellia japonica

  • Cho, Jeong-Yong;Ji, Soo-Hyun;Moon, Jae-Hak;Lee, Kye-Han;Jung, Kyung-Hee;Park, Keun-Hyung
    • Food Science and Biotechnology
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    • v.17 no.5
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    • pp.1060-1065
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    • 2008
  • A novel benzoyl glucoside (4) and 13 known phenolic compounds were isolated from the leaves of Camellia japonica by a guided 1,1-diphenyl-2-picrylhydrazyl (DPPH) radical scavenging assay. The structure of 4 was determined to be 4-hydroxy-2-methoxyphenol 1-O-$\beta$-D-(6'-O-p-hydroxylbenzoyl)-glucopyranoside (camelliadiphenoside). The 13 known compounds were identified as (E)-coniferyl alcohol (1), (-)-epicatechin (2), 4-hydroxyphenol 1-O-$\beta$-D-(6-O-p-hydroxybenzoyl) glucopyranoside (3), naringenin 7-O-$\beta$-D-glucopyranoside (5), quercetin 3-O-$\beta$-L-rhamnopyranosyl(1$\rightarrow$6)-$\beta$-D-glucopyranoside (6), kaempferol 3-O-$\beta$-L-rhamnopyranosyl(1$\rightarrow$6)-$\beta$-D-glucopyranoside (7), (+)-catechin (8), 1,6-di-O-p-hydroxybenzoyl-$\beta$-D-glucopyranoside (9), phloretin 2'-O-$\beta$-D-glucopyranoside (10), quercetin 3-O-$\beta$-D-glucopyranoside (11), quercetin 3-O-$\beta$-D-galactopyranoside (12), kaempferol 3-O-$\beta$-D-galactopyranoside (13), and kaempferol 3-O-$\beta$-D-glucopyranoside (14). Their chemical structures were determined by the spectroscopic data of fast atom bondardment mass spectrometry (FABMS) and nuclear magnetic resonance (NMR). Flavonoids having the catechol moiety showed significantly higher DPPH radical scavenging activity than other isolated compounds having monohydroxy phenyl group.

Chemical Constituents of Abies koreana Leaves with Inhibitory Activity against Nitric Oxide Production in BV2 Microglia Cells

  • Baek, Sa-Wang;Kim, E. Ray;Kim, Jin-Woong;Kim, Young-Choong
    • Natural Product Sciences
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    • v.17 no.3
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    • pp.175-180
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    • 2011
  • Eleven compounds were isolated from fresh leaves of Abies koreana (Pinaceae), and structures of these compounds were determined to be 3-hydroxy-2-methyl-4-pyrone (1), maltol-3-O-${\beta}$-D-glucoside (2), (-)-epicatechin (3), naringenin 7-O-${\beta}$-D-glucopyranoside (4), naringenin-7-O-rhamnoglucoside (5), kaempferol 3-O-${\beta}$-D-glucopyranoside (6), (+)-isolariciresinol (7), secoisolariciresinol (8), rhododendrol (9), ferulic acid (10) and 4-(4-hydroxyphenyl)butan-2-one (rheosmin) (11) by comparing $^1H$-, $^{13}C$-NMR and MS spectroscopic data with reference values. Compounds 3, 5, 7, 8, 9, 10, 11 were isolated for the first time from A. koreana. Among eleven isolates, compounds 1, 7 and 11 showed inhibitory activities against lipopolysaccharide (LPS)-induced nitric oxide (NO) production in BV-2 microglia in a concentration dependent manner.

Studies on Biological Activity of Wood Extractives(VI) - Flavonoids in heartwood of Prunus sargentii - (수목추출물의 생리활성에 관한 연구(VI) - 산벚나무 심재의 Flavonoids -)

  • Lee, Hak-Ju;Lee, Sung-Suk;Choi, Don-Ha;Kato, Atsushi
    • Journal of the Korean Wood Science and Technology
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    • v.29 no.2
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    • pp.133-139
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    • 2001
  • The structures of six flavonoids isolated from heartwood of Prunus sargentii(Rosaceae) were analyzed by Mass and NMR spectrometry. These flavonoids were grouped into dihydroflavonol, flavanone, and flavanone glycoside, and identified as follows : 3,3',4',5,7-pentahydroxyflavanone(taxifolin) as a dihydroflavonol, 5-hydroxy-7-methoxyflavanone(pinostrobin), 4',5,7-trihydroxyflavanone(naringenin), 3',4',5,7-tetrahydroxyflavanone(eriodictyol), 5,7-dihydroxyflavanone(pinoccmbrin) as a flavanone and 7-hydroxyflavanone 5-O-${\beta}$-D-glucopyranoside(verecundin) as a flavanone glycoside.

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Chemical Components from the Stems of Pueraria lobata and Their Tyrosinase Inhibitory Activity

  • Morgan, Abubaker M.A.;Jeon, Mi Ni;Jeong, Min Hye;Yang, Seo Young;Kim, Young Ho
    • Natural Product Sciences
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    • v.22 no.2
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    • pp.111-116
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    • 2016
  • Phytochemical investigation of the stems of Pueraria lobata (Wild) Ohwi (Leguminosae), led to the isolation of eighteen known compounds: ${\beta}$-amyrone (1), (+)-pinoresinol (2), (+)-syringaresinol (3) $(+)-syringaresinol-O-{\beta}-{\small{D}}-glucoside$ (4), (+)-lariciresinol (5), (-)-tuberosin (6), naringenin (7), liquiritigenin (8), isoliquiritigenin (9) genistein (10), daidzein (11) daidzin (12) daidzein 4',7-diglucoside (13) 2,4,4'-trihydroxy deoxybenzoin (14), S-(+)-1-hydroxy-3-(4-hydroxyphenyl)-1-(4-hydroxy-2-methoxy-phenyl)propan-2-one (15), methyl $2-O-{\beta}-{\small{D}}-glucopyranosylbenzoate$ (16), pyromeconic acid $3-O-{\beta}-{\small{D}}-glucopyranoside$ 6'- (O-4''-hydroxy-3-methoxybenzoate) (17), and allantion (18). The chemical structures of these compounds were elucidated from spectroscopic data and by comparison of those data with previously published results. The effects of isolated compounds on mushroom tyrosinase enzymatic activity were screened. The results indicated that, chloroform extract of P. lobata stems turned out to be having tyrosinase inhibitory effect, and only compounds 5, 8, 9, and 11 showed enzyme inhibitory activity, with $IC_{50}$ values of $21.49{\pm}4.44$, $25.24{\pm}6.79$, $4.85{\pm}2.29$, and $17.50{\pm}1.29{\mu}M$, respectively, in comparison with these of positive control, kojic acid ($IC_{50}\;12.28{\pm}2.72{\mu}M$). The results suggest that P. lobata stems extract as well as its chemical components may represent as potential candidates for tyrosinase inhibitors.

Studies on Biological Activity of Wood Extractives(VII) - Antimicrobial and Antioxidation Activities of Extractives from the Heartwood of Prunus sargentii - (수목추출물의 생리활성에 관한 연구(VII) - 산벚나무 심재 추출성분의 항균 및 항산화활성 -)

  • Lee, Sung-Suk;Lee, Hak-Ju;Choi, Don-Ha
    • Journal of the Korean Wood Science and Technology
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    • v.29 no.2
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    • pp.140-145
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    • 2001
  • Antimicrobial and antioxidative activities on heartwood extractives of domestic species were investigated to develop a natural fungicide or preservative. Six flavanones including pinostrobin, eriodictyol, naringenin, pinocembrin, taxifolin and verecundin were isolated from Prunus sargentii which has been selected due to its high antimicrobial and antioxidative activities among the tested species. According to the results of antifungal test, pinocembrin was evaluated as the highest antifungal compound among the test compounds, which showed 80% of hyphal growth inhibition rate. Antifungal activity of pinocembrin was similar to hinokitiol(${\beta}$-thujaplicin), strong antimicrobial compound isolated from Thujopsis dolabrata. Naringenin followed pinocembrin in its antifungal activity. However, verecundin did not show any antifungal activity. No compound was effective in antibacterial activities. As a result of the measurement of free radical scavenging activity, antioxidative activities of taxifolin and eriodictyol were 2 times that of ${\alpha}$-tocopherol, and antioxidative index of these compounds were even superior to that of ${\alpha}$-tocopherol. In this regard, it could inferred that high antifungal and antioxidative activities of extractives of P. sargentii were derived from pinocembrin, taxifolin and eriodictyol, respectively.

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Anti-inflammatory Activity of Flavonoids from Populus davidiana

  • Zhang, XinFeng;Hung, Tran Manh;Phuong, Phuong Thien;Ngoc, Tran Minh;Min, Byung-Sun;Song, Kyung-Sik;Seong, Yeon-Hee;Bae, Ki-Hwan
    • Archives of Pharmacal Research
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    • v.29 no.12
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    • pp.1102-1108
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    • 2006
  • An in vitro bioassay-guide revealed that the methanol (MeOH) extract of the stem bark of Populus davidiana showed considerable inhibitory activity against cyclooxygenase (COX-1, COX-2). Continuous phytochemical study of the MeOH extract of this plant led to the isolation of ten flavonoids; sakuranetin (1), rhamnocitrin (2), 7-O-methylaromadendrin (3), naringenin (4), eriodictyol (5), aromadendrin (6), kaempferol (7), neosakuranin (8), sakuranin (9) and sakurenetin-5,4'-di-${\beta}$-D-glucopyranoside (10). Their structures were identified on the basis of their physicochemical and spectroscopic analyses. The isolated compounds, 1-10, were tested for their inhibitory activities against COX-1 and COX-2. Compound 7 was found to have potent inhibitory effect on COX-1 and a moderate effect on COX-2, meanwhile, compounds 1-6 showed moderate inhibition against COX-1 only. Moreover, compounds 5-8 exhibited suppressive effects on xanthine oxidase (XO). These results may explain, in part, the traditional uses of P. davidiana in ethnomedicine.