• 제목/요약/키워드: Flavan

검색결과 62건 처리시간 0.029초

Jack Fruit 잎으로부터 새로운 Glucosyltransferase 저해물질 분리 및 화학구조 (Chemical Structure and Isolation of Novel Glucosyltransferase Inhibitor from Artocarpus heterophyllus folium)

  • 안봉전
    • 한국식품과학회지
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    • 제29권6호
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    • pp.1304-1308
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    • 1997
  • 충치 예방물질의 지속적인 연구로 Jack Fruit 잎으로부터 새로운 procyanidin류를 분리하였고 thiolysis 및 기기 분석에 의해 구조를 결정하였다. 신규화합물의 화학 구조는 flavan-3-ol 화합물의 삼량체인 $(-)-epiafzele-chin-(4{\beta}{\rightaroow}8)-afzelechin-(4{\alpha}{\rightaroow}8)-catechin$의 구조로, 분자량이 $833\;[M-H]^-$ 이었다. 화학 구조가 결정된 신규화합물의 glucosyltransferase저해 실험 결과 1.0 mM에서 완벽한 저해 효과가 관찰되었고 저해기작은 비경쟁적 저해제임을 알았다.

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측백나무(Thuja orientalis Linnaeus) 잎의 추출성분 (Extractives from the leaves of Thuja orientalis Linnaeus)

  • 이상극;김진규;함연호;배영수
    • 임산에너지
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    • 제21권1호
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    • pp.56-64
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    • 2002
  • 측백나무 잎을 채취하여 건조시킨 후 분말로 제조하여 아세톤-물(7:3, v/v)로 추출하고 hexane, CH₂C1₂, EtOAc, 그리고 수용성으로 분획하여 동결건조 시켰다. 그 중에서 EtOAc 분획을 Sephadex LH-20으로 충진한 칼럼에서 메탄올과 에탄올-헥산 혼합액을 용리용매로 사용하여 칼럼크로마토그래피를 실시하였다. 단리된 화합물들은 TLC로 확인한 후 NMR스펙트럼을 사용하여 정확한 구조규명을 하였고 FAB-MS로써 분자량을 측정하였다. 주로 quercetin-3-O-a-L-rhamnopyranoside와 myricetin-3-O-α-L-rhamnopyranoside 같은 flavononol 유도체들이 다량으로 포함되어 있었으며 비교적 적은 양의 (+)-catechin과 (+)-gallocatechin 같은 flavan 화합물들도 함께 단리 되었다. 각 분획물들과 단리된 화합물들은 DPPH 라디칼 소거법을 이용하여 항산화실험을 실시하였으며, 모두 우수한 항산화 효능이 있는 것으로 나타났다.

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Tannins from Rubus coreanum

  • Lee, Yeon-Ah;Lee, Min-Won
    • 생약학회지
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    • 제26권1호
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    • pp.27-30
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    • 1995
  • Tannins were isolated from the stems of Rubus coreanum and identified as (-)-epicatechin, (+)-catechin, procyanidin B-4 and sanguiin H-4 by spectral analysis.

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Determination of Phytochemical Contents and Biological Activities from the Fruits of Elaeagnus multiflora

  • Lee, Jin-Hwan;Seo, Weon-Taek;Cho, Kye-Man
    • Preventive Nutrition and Food Science
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    • 제16권1호
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    • pp.29-36
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    • 2011
  • The purpose of this study was to investigate the phytochemical contents and biological activities, including $\alpha$-glucosidase inhibitory activity and antioxidant activity, from the fruits of Elaeagnus multiflora using different solvent systems. The 50% ethanol extract of this species showed the most potent $\alpha$-glucosidase inibitory activity (88.5%) at a concentration of 1 mg/mL. Moreover, this extract also displayed the strongest antioxidant activity in each assay, showing 96.3% in DPPH scavenging activity, 98.2% in ABTS scavenging activity, and 2.5% in reducing power. The highest total phytochemical contents, including flavan-3-ols, phenolic acids, and flavonoids, were observed in the 50% ethanol extract. Interestingly, flavan-3-ols (3.150 mg/g) were detected at a significantly higher total content than those of phenolic acids (0.380 mg/g) and flavonoids (not detected). Additionally, the contents of individual phytochemicals showed remarkable differences, especially the epicatechin gallate (2.008 mg/g) and gallic acid (0.099 mg/g), which were the predominant constituents of each phytochemical type. Therefore, our results suggest that the 50% ethanol extract of E. multiflora fruits has strong biological activities, which are correlated with high phytochemical contents.

Proliferative Effects of Flavan-3-ols and Propelargonidins from Rhizomes of Drynaria fortunei on MCF-7 and Osteoblastic Cells

  • Chang, Eun-Ju;Lee, Won-Jung;Cho, Sung-Hee;Choi, Sang-Won
    • Archives of Pharmacal Research
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    • 제26권8호
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    • pp.620-630
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    • 2003
  • The proliferative effects of thirty Oriental medicinal herbs on MCF-7 (estrogen-sensitive breast cancer cell line) and ROS 17/2.8 osteoblast-like cells were determined using the MTT assay. Methanol extracts from several herbs was found to show proliferative activity on the above two cell lines in the range of 5 to 100 $\mu$g/mL. Among these active herbs, the methanol extract from the rhizomes of Drynaria fortunei showed the most potent proliferative activity, and the cell proliferations were significantly increase by 136 and 158% in the MCF-7 and ROS 17/2.8 cells, respectively, when treated with 100 $\mu$ g/mL. Through a bioassay-guided separation, eight flavonoids, including four new flavan-3-ols and two propelargonidins, together with the known (-)-epiafzelechin and naringin, were isolated. Their chemical structures were characterized as (-)-epiafzelechin (1), (-)-epiafzelechin-3-O-$\beta$-D-allopyranoside (2), (-)-epiafzelechin-3-O-(6"-O-acetyl)-$\beta$-D-allopyranoside (3), 4$\beta$-carboxymethyl-(-)-epiafzelechin methyl ester (4), 4$\beta$-car-boxymethyl-(-)-epiafzelechin sodium salt (5), naringin (6), (-)-epiafzelechin-(4$\beta$\rightarrow8)-4$\beta$-car-boxymethylepiafzelechin methyl ester (7) and (-)-epiafzelechin-($4\beta\rightarrow8, 2\beta\rightarrowΟ\rightarrow7)-epiafzelechin-(4\beta\righarrow8)-epiafzelechin (8) by extensive 1D and 2D NMR spectroscopy. Most of these flavonoids, in the range of $10^{-15}∼10^{-6}$ M, accelerated the proliferation of MCF-7 cell, with compounds 7 and 8, in the range of $10^{-15}∼10^{-12}$ M, showing especially potent proliferation effects. Meanwhile, seven flavonoids, with the exception of compound 4, stimulated the proliferation of ROS 17/2.8 cells in the range of $10^{-15}∼10^{-6}$ M, with compounds 5-8 especially accelerating the proliferation, in dose-dependent manners ($10^{-15}∼10^{-9}$ M), and their proliferative effect was much stronger than that of $E_2$ and genistein. These results suggest that propelargonidin dimers and trimers isolated from the rhizomes of Drynaria fortunei may be useful as potential phytoestrogens, which play important physiological roles in the prevention of postmenopausal osteoporosis.

박태기나무의 잎으로부터 피부멜라닌 색소생성 억제성분의 분리 (The Isolation of the Inhibitory Constitutents on Melanin Polymer Formation from the Leaves of Cercis chinensis)

  • 김소영;김진준;장태수;정시련;이승호
    • 생약학회지
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    • 제30권4호
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    • pp.397-403
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    • 1999
  • Tyrosinase plays an important role in the process of melanin polymer biosynthesis. Therefore, the enzyme inhibitors have been of great concern as cosmetics to have skin-whitening effects on the local hyperpigmentation. During the search for new inhibitory compounds on melanin polymer biosynthesis from natural sources, MeOH extracts of 589 higher plants were tested for the inhibitory effect on tyrosinase activity by the muschroom tyrosinase assay in vitro. Among plants tested, the leaves of Cercis chinensis exhibited potent inhibitory effect on mushroom tyrosinase activity. Subsequently seven active compounds were isolated from the ethyl acetate soluble part of acetone extract of the leaves of C. chinensis by the activity guided fractionation monitoring the inhibitory effect on tyrosinase activity. Their chemical structures were identified as $kaempferol-3-0-{\alpha}-L-rhamnoside$, quercitrin, $myricetin-3-0-{\alpha}-L-rhamnoside$, myricetin-3-0-(2'-O-galloyl)- ${\alpha}$ -L-rhamopyranoside (desmanthin), (-)-epicatechin-3-0-gallate, (-)-epigallocatechin-3-0-gallate, and methyl gallate on the basis of the speculation of spectral data and chemical reaction. Among the flavonol rhamnosides, myricetin-3-0-(2'-O-galloyl)- -L-rhamnoside(desmanthin) showed most potent inhibitory effect on tyrosinase activity and the structure of B-ring in flavonol moiety was related to the activity. (-)-Epigallocatechin-3-O-gallate having pyrogallol group in flavan-3-ol moiety exhibited more potent inhibitory effect than (-)-epicatechin-3-0-gallate having catechol group in flavan-3-ol moiety on mushroom tyrosinase activity.

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Evolution of 49 Phenolic Compounds in Shortly-aged Red Wines Made from Cabernet Gernischt (Vitis vinifera L. cv.)

  • Li, Zheng;Pan, Qiu-Hong;Jin, Zan-Min;He, Jian-Jun;Liang, Na-Na;Duan, Chang-Qing
    • Food Science and Biotechnology
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    • 제18권4호
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    • pp.1001-1012
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    • 2009
  • A total of 49 phenolic compounds were identified from the aged red wines made from Cabernet Gernischt (Vitis vinifera L. cv.) grapes, a Chinese characteristic variety, including 13 anthocyanins, 4 pryanocyanins, 4 flavan-3-ol monomers, 6 flavan-3-ol polymers, 7 flavonols, 6 hydroxybenzoic acids, 5 hydroxycinnamic acids, 3 stilbenes, and 1 polymeric pigment. Evolution of these compounds was investigated in wines aged 1 to 13 months. Variance analysis showed that the levels of most phenolics existed significant difference in between wines aged 3 and 9 months. Cluster analysis indicated that 2 groups could be distinguished, one corresponding to wines aged 1 to 3 months and the other to wines aged 4 to 13 months. It was thus suggested that there were 2 key-stages for the development of fine wine quality, at the aged 3 and 9 months, respectively. This work would provide some helpful information for quality control in wine production.

산겨릅나무 목질부에서 분리한 페놀성 화합물의 DPPH 라디칼 소거활성 (DPPH Radical Scavenging Activity of Phenolic Compounds Isolated from the Stem Wood of Acer tegmentosum)

  • 권동주;김진규;배영수
    • Journal of the Korean Wood Science and Technology
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    • 제39권1호
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    • pp.104-112
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    • 2011
  • 현재까지 산겨릅나무의 식물화학적인 연구는 수피부에 국한되어 있으며, 목질부의 성분연구는 전혀 보고된 것이 없다. 본 연구는 산겨릅나무 목질부로부터 2개의 flavan 3-ol, 3개의 phenolic acid/alcohol 및 2개의 coumarin 화합물을 컬럼크로마토그래피를 연속적으로 실시하여 분리하였다. 화합물의 구조는 $^1H$-NMR, $^{13}C$-NMR, 2D-NMR 및 MS 스펙트럼을 분석하여, (+)-catechin (1), (-)-epicatechin (2), $p$-hydroxybenzaldehyde (3), syringic alcohol (4), $p$-tyrosol (5), scopoletin (6) 및 cleomiscosin A (7)으로 동정하였으며, 그 중 $p$-hydroxybenzaldehyde (3), syringic alcohol (4), scopoletin (6) 및 cleomiscosin A (7)는 산겨릅나무에서는 처음 분리하였다. 화합물의 DPPH 라디칼 소거활성 측정 결과 (+)-catechin (1)과 (-)-epicatechin (2)은 양성 대조구로 사용한 BHA보다 우수한 항산화 활성을 나타냈다.