• 제목/요약/키워드: catechin-7-O-$\beta$-D-glucopyranoside

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왕느릅나무 수피의 페놀성 화합물 및 항산화 활성 (Phenolic Compounds from Barks of Ulmus macrocarpa and Its Antioxidative Activities)

  • 권영민;이재희;이민원
    • 생약학회지
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    • 제33권4호통권131호
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    • pp.404-410
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    • 2002
  • Phytochemical examination of Barks of Ulmus macrocarpa has led to the isolation and characterization of two fla-vanonol, taxifolin $7-O-{\beta}-D-glucopyranoside$ (1), taxifolin $3'-0-7-{\beta}-glucopyranoside$ (2), two flavanone eriodictyol $7-O-{\beta}-D-glucopyranoside$ (3), nalingenin $7-O-{\beta}-D-glucopyranoside$ (4), three flavan 3-ol, (+)-catechin (5), (-)-epicatechin (6), (+)-catechin 7-O-{\beta}-D-glucopyranoside (7) and one proanthocyanidin, procyanidin B-1 (8). Antioxidative activity of these compounds was determined by measuring the radical scavenging effect on 1,1-diphenyl-2- picrylhydrazyl (DPPH) radicals . (+)-Catechin (5) , (-)-epicatechin (6), (+)-catechin $7-O-{\beta}-D-glucopyranoside$ (7) and procyanidin B-1 (8) showed significant antioxidative activity.

국내산 주요 침엽수 잎의 추출성분(I) - 구상나무(Abies koreana Maximowicz)와 전나무(Abies holophylla Wilson) 잎 추출성분의 항산화 활성 - (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 -)

  • 이상극;최돈하;배영수
    • Journal of the Korean Wood Science and Technology
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    • 제34권3호
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    • pp.73-83
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    • 2006
  • 구상나무(Abies koreana Maximowicz)와 전나무(Abies holophylla Wilson) 잎을 채취하여 건조시킨 후 분말로 제조하여 각각 1.5 kg을 아세톤-물(7:3, v/v)로 추출하고 헥산, 메틸렌클로라이드, 에틸아세테이트 및 수용성으로 분획하여 동결건조 시켰다. 에틸아세테이트용성 분획을 Sephadex LH-20으로 충진한 칼럼에서 메탄올과 에탄올-헥산 혼합액을 용리용매로 사용하여 칼럼크로마토그래피를 실시하였다. 단리된 화합물들은 TLC로 확인한 후 $^1H-$, $^{13}C-NMR$, COSY, HETCOR 등의 스펙트럼을 사용하여 정확한 구조를 규명하였고 FAB 및 EI-MS로써 분자량을 측정하였다. 많은 양의 aromadendrin-7-O-${\beta}$-D-glucopyranoside (화합물 III), polydatin (화합물 VI), (-)-rhododendrol-2-O-${\beta}$-D-glucopyranoside (화합물 VII)가 단리되었으며, 소량의 (+)-catechin (화합물 I), kaempferol-3-O-${\beta}$-D-glucopyranoside (화합물IV), myricetin-3-O-${\beta}$-D-glucopyranoside (화합물 V), naringenin-7-O-${\beta}$-D-glucopyranoside (화합물 II)도 단리 되었다. DPPH 라디칼 소거법을 이용하여 단리된 화합물들에 대한 항산화 활성시험을 실시하였으며 (+)- catechin과 polydatin이 항산화 효능을 나타내었다.

상수리나무(Querus acutissima)와 굴참나무(Querus vcariabilis) 수피의 추출성분 (Extractives from the barks of Querus acutissima and Quercus variabilis)

  • 김진규;이상극;함연호;배영수
    • 임산에너지
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    • 제21권1호
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    • pp.41-48
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    • 2002
  • 참나무속 상수리나무와 굴참나무 수피를 채취하여 아세톤-물(7:3, v/v) 혼합용액으로 추출하고 유기용매를 제거한 후 hexane, CH₂C1₂, EtOAc 및 수용성으로 분획하여 동결건조하였다. 두 수종의 EtOAc용성 분획물은 MeOH 수용액 및 EtOH-hexane 혼합용액을 사용하여 Sephadex LH-20 칼럼크로마토그래피를 수행하였다. 단리된 화합물의 구조는 ¹H, /sup 13/C 및 2D-NMR spectrum으로 구조를 구명하였다. 화합물의 분자량은 FAB-MS로 측정하였다. 굴참나무에서는 (+)-catechin, caffeic acid, taxifolin-3-O-β-D-glucopyranoside를 단리 하였으며 상수리나무에서는 (+)-catechin, (+)-gallocatechin, gallic acid, taxifolin-3-O-β-D-glucopyranoside를 단리 하였다.

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큰잎자작(Betula maximowicziana) 변재의 추출성분 (Extractives from the Sapwood of Betula maximowicziana)

  • 이학주;加藤厚
    • Journal of the Korean Wood Science and Technology
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    • 제31권2호
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    • pp.45-51
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    • 2003
  • 큰잎자작 변재의 메탄올(methanol, MeOH) 조추출물로부터 silica gel column, CPC 등의 크로마토그라피를 이용하여 4종의 화합물을 단리하였으며, 단리물질에 대한 NMR 등의 기기분석 결과, flavonoid 및 lignan 배당체인 catechin 7-O-𝛽-D-xylopyranoside, lyoniresinol 9'-O-𝛽-D-glucopyranoside, 그리고 diarylheptanoid인 11-oxo-3, 8, 12, 17-tetrahydroxy-9-ene [7, 0]-metacyclophane 및 11-oxo-3, 8, 9, 10, 12, 17-hexahydroxy [7, 0]-metacyclophane으로 각각 동정하였다.

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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    • 제17권5호
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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.

Phenolic Compounds on the Leaves of Betula Platyphylla var. latifolia

  • Lee, Min-Won;Takashi Tanaka;Gen-Ichiro Nonaka;Hahn, Dug-Ryoung
    • Archives of Pharmacal Research
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    • 제15권3호
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    • pp.211-214
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    • 1992
  • Chemical examination of Betula platyphylla var. latifolia afforded a novel diarylheptanoid named betulateraol, together with a phenylpropanoid (3, 4'-dihydroxypropio-phenone), flavan-3-ol [(+)-catechin] and its glycosides [(+)-catechin 5-O-$\beta$-glucopyranoside, (+)-catechin 7-0-$\beta$-D-glucopyranoside] and two proanthocyanidins (procyanidins B-1 and B-3).

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Anti-oxidative Activities of Phenolic Compounds from barks of Pinus densiflora Siebold et Zuccarini

  • Kwon, Joo-Hee;Kwon, Yong-Min;Choi, Sun-Eun;Park, Kwan-Hee;Lee, Min-Won
    • Natural Product Sciences
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    • 제16권1호
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    • pp.10-14
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    • 2010
  • Phytochemical examination of the barks of Pinus densiflora Siebold et Zuccarini has led to the isolation of one phenylpropanoid, one lignan, one flavonoid, one flavan 3-ol and two procyanidins : 4-O-$\beta$-D-glucopyranosyl-p-coumaric acid (1), 2,3-dihydro-2-(4-methoxy)-7-hydroxy-3-hydroxymethyl-5-(3-hydroxy propyl)-benzofuran 3-O-$\alpha$-D-glucopyranoside (2), taxifolin 3'-O-$\beta$-D-glucopyranoside (3), (+)-catechin (4), procyanidin B1 (5) and epicatechin-($4{\beta}$-8)-catechin-($4{\alpha}$-8)-catechin (6). Among them, Compound 4, 5 and 6 showed potent anti-oxidative activities and these anti-oxidative activities were significantly different compared with ascorbic acid as positive control.

Smilax riparia 잎의 항산화 성분 (The Anti-oxidative Compounds of Smilax riparia Leaves)

  • 조은선;김정일;김호현;전인주;함인혜;황완균
    • 약학회지
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    • 제47권5호
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    • pp.300-306
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    • 2003
  • Rhizoma of Smilax china has been used as anti-inflammatory and analgesic, antiedemic agent in Korean folk medicine. In order to investigate the efficacy of anti-oxidative activity, the activity-guided fractionation and the isolation were performed. Each fractions ($H_2O$ fraction, 20%, 40%, 60%, 100% MeOH fractions and CHCl$_3$ fraction) was examined antioxidant activity by 1,1-diphenyl-2-picrylhydrazyl (DPPH) free radical scavenging potential. It was revealed that 40%, 20% MeOH fractions and $H_2O$ fractions have significant anti-oxidative activity. From 40% and 20% MeOH fractions two flavonoid glycosides and one procyanidin were isolated and elucidated apigenin-7-Ο-$\alpha$-L-rhamnopyranosyl(1\longrightarrow2)-$\beta$-D-glucopyranoside, apigenin-7-Ο-$\alpha$-L-rhamnopyranosyl(1\longrightarrow6)-$\beta$-D-glucopyranoside and catechin(4$\alpha$\longrightarrow6)epicatechin through their physicochemical data and IR, FAB-MS, $^{13}$ C-NMR, and $^1$H-NMR analysis with authentics, respectively. The isolated compounds were examined by DPPH method. Apigenin-7-Ο-$\alpha$-L-rhamnopyranosyl(1\longrightarrow2)-$\beta$-D-glucopyranoside and catechin (4$\alpha$\longrightarrow6) epicatechin showed powerful radical scavenging activities on DPPH radical among three compounds.

다래나무뿌리의 식물화학적 성분 (Phytochemical Constituents of Actinidia arguta)

  • 황준이;지옥표;문형인
    • 생약학회지
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    • 제31권3호
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    • pp.357-363
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    • 2000
  • The root of Actinidia arguta was extracted with methanol and the methanol extract was suspended in $H_2O$ and successively partitioned with n-hexane, $CH_2Cl_2$, EtOAc and n-BuOH. Repeated column chromatographic separation of the EtOAc extract resulted in the isolation of two flavonoids (compounds 2 and 3) and two triterpenes (compounds 1 and 4) and $CH_2Cl_2$, extract to afford three lignans (compounds 5-7). Their structures have been established by spectroscopic, means to be (+)-tormentoside(1), (-)-catechin(2), (-)-epicatechin(3), (+)-uscaphic $acid-28-O-[\beta}-D-glucopyranoside$(4), (+)-pinoresinol(5), (+)-medioresinol(6), and (-)-syringaresinol(7).

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Cytotoxic Phenolic Constituents of Acer tegmentosum Maxim

  • Park, Ki-Myun;Yang, Min-Cheol;Lee, Kyu-Ha;Kim, Kyung-Ran;Choi, Sang-Un;Lee, Kang-Ro
    • Archives of Pharmacal Research
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    • 제29권12호
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    • pp.1086-1090
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    • 2006
  • The chromatographic separation of the MeOH extract from the twigs of Acer tegmentosum led to the isolation of ten phenolic compounds. The structures of these compounds were determined using spectroscopic methods as 3,7,3',4'-tetramethyl-quercetin (1), 5,3'-dihydroxy-3,7,4'-trimethoxy flavone (2), 2,6-dimethoxy-p-hydroquinone (3), (-)-catechin (4), morin-3-O-${\alpha}$-L-lyxoside (5), p-hydroxy phenylethyl-O-${\beta}$-D-glucopyranoside (6), 3,5-dimethoxy-4-hydroxy phenyl-1-O-${\beta}$-D-glucoside (7), fraxin (8), 3,5-dimethoxy-benzyl alcohol 4-O-${\beta}$-D-glucopyranoside (9) and 4-(2,3-dihydroxy propyl)-2,6-dimethoxy phenyl ${\beta}$-D-glucopyranoside (10). The compounds were examined for their cytotoxic activity against five cancer cell lines. Compound 3 exhibited good cytotoxic activity against five human cancer cell lines with $ED_{50}$ values ranging from $1.32\;to\;3.85\;{\mu}M$.