• Title/Summary/Keyword: $catechin-7-O-\

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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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    • v.29 no.12
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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 $1.32\;to\;3.85\;{\mu}M$.

Free Radical Scavenging Activity of the Seed of Phaseolus calcaratus Roxburgh

  • Fang, Minghao;Cho, Hyoung-Kwon;Ahn, Yun-Pyo;Ro, Sang-Jeong;Jeon, Young-Mi;Whang, Wan Kyuun;Lee, Jeong-Chae
    • Natural Product Sciences
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    • v.16 no.3
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    • pp.169-174
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    • 2010
  • The seed of Phaseolus calcaratus Roxburgh (PHCR) is traditionally used for anti-pyretic and antiinflammatory effects. Although these effects are believed to be related to its antioxidant potential, little information is available for the mechanisms by which PHCR seed might scavenge free radicals or otherwise act as an antioxidant. In the present study, we purified some fractions from the ethanol extract of PHCR seed and evaluated each fraction's ability to scavenge free radicals generated by cell-free systems. We also identified active compound that is putatively responsible for free radical scavenging by analyzing NMR spectra. PHCR samples exhibited a concentration-dependent radical scavenging activity against hydroxyl radicals, superoxide anions, and DPPH radicals. Of the samples tested, a methanol-eluted sub-fraction from the PHCR extract, named $FF_4$, scavenged these radicals more effectively than the other fractions. We identified catechin-7-O-$\beta$-Dglucopyranoside as the active compound responsible for free radical scavenging potential of $FF_4$.

Cytotoxic constituents from the stem of Rhododendron mucronulatum (진달래 줄기의 세포독성 성분)

  • Hong, He-Sun;Jeon, Seung-Ho;Kwon, Yong-Soo
    • Korean Journal of Pharmacognosy
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    • v.38 no.3 s.150
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    • pp.227-233
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    • 2007
  • Seven compounds were isolated from the n-BuOH soluble fraction of stem of Rhododendron mucronulatum as cytotoxic principles against brine shrimp lethality test. On the basis of spectral data, seven compounds were identified as (-)-catechin (1), (+)-epicatechin (2), taxifolin (3), scopoletin (4), quercetin (5), $taxifolin-3-O-{\alpha}-L- arabinopyranoside$ (6), and astragalin (7). Among tested compounds, $taxifolin-3-O-{\alpha}-L-arabinopyranoside$ (6) exhibited potent activity with $LC_{50}$ value at 4.6 ${\mu}g/ml$.

Flavonoid Glycosides from Needles of Larix leptolepis(Pinaceae) (일본잎갈나무 잎의 후라보노이드 배당체)

  • Kim, Jin-Kyu;Park, Wan-Geun;Bae, Young-Soo
    • Journal of the Korean Wood Science and Technology
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    • v.25 no.2
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    • pp.81-87
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    • 1997
  • 일본잎갈나무잎을 채취하여 아세톤 : 물 (7 : 3, v/v) 의 혼합용액으로 추출한 후 에틸아세테이트용성 화합물과 수용성 화합물로 분리하였으며 Sephadex LH-20으로 충진한 칼럼을 사용하여 화합물을 단리 하였다. 단리 화합물을 확인하기 위하여 셀룰로오스 박층 크로마토그래피(TLC)를 실시한 후 자외선 램프 하에서 관찰하였다. 바닐린 발색제를 분무히여 정색반응을 조사하고 $R_r$ 값을 구하였다. 단리된 화합물들의 구조는 $^1H$-NMR과 $^{13}C$-NMR 스펙트럼을 이용하여 그 구조를 규명하였으며 에틸아세테이트용성 화합물에서는 (+)-catechin, (-)-epicatechin, kaempferol-O-arabinofuranoside와 kaempferol-3-O-arabinopyranoside, 수용성 화합물에서는 apigenin-8-C-rhamnosyl-($1"'{\rightarrow}2"$)-glucoside(2"-O-rhamnosylvitexin)을 단리 하였다.

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Phytochemical Studies on Paeoniae Radix (2);Phenolic and Related compounds (작약(芍藥)의 성분연구(成分硏究) (2);Phenol성 물질 및 관련화합물들의 분리)

  • Kim, Ju-Sun;Kim, Yoon-Jung;Lee, Joo-Young;Kang, Sam-Sik
    • Korean Journal of Pharmacognosy
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    • v.39 no.1
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    • pp.28-36
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    • 2008
  • From the 70% EtOH extract of Paeonia lactiflora roots (Paeoniaceae), fourteen phenolic and related compounds were isolated. They were identified as ${\alpha}-tocopherol$ (1), dioctylphthalate (2), ${\alpha}-tocospiro$ B (3), paeonol (4), 3,3'-di-O-methylellagic acid(5), 3,4'-di-O-methylellagic acid (6), benzoic acid (7), aromadendrin (8), p-hydroxybenzoic acid (9), (+)-catechin (10), gallic acid (11), nicotinamide (12), methyl gallate (13) and $1,2,3,4,6-penta-O-galloyl-{\beta}-D-glucose$ (14) by spectroscopic methods. Among these compounds, 1-3, 5, 6, 8 and 12 were isolated for the first time from this plant.

Phenolic Compounds from Japanese anise (Illicium anisatum L.) Twigs

  • Min, Hee-Jeong;Bae, Young-Soo
    • Journal of the Korean Wood Science and Technology
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    • v.45 no.4
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    • pp.456-462
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    • 2017
  • Japanese anise (Illicium anisatum L.) twigs were collected and ground after drying, then immersed with 50% aqueous acetone for 3 days. After filtration, the extracts were fractionated with n-hexane, chloroform ($CHCl_3$), ethylacetate (EtOAc) and $H_2O$, and then freeze-dried after condensation. A portion of EtOAc soluble fraction (5.7 g) was chromatographed on a Sephadex LH-20 column with various aqueous $MeOH-H_2O$. Compound 2 and compound 3 were isolated from fraction 8 and 5, respectively. Compound 1 and compound 4 were isolated after rechromatography of fraction 7. The isolated compounds were elucidated as (+)-catechin (1), taxifolin (2), taxifolin-3-O-${\beta}$-D-(+)-xylopyranose (3) and quercitrin (4) by spectral and literature data, and by comparison with the authentic samples. Of the isolated compounds, taxifolin (2), taxifolin-3-O-${\beta}$-D-(+)-D-xylopyranose (3) and quercitrin (4) were isolated, for the first time, from the extracts of japanese anise twigs.

Biological Activities on Phenolic Compounds of Japanese anise (Illicium anisatum L) Extracts

  • Shinn, Seong-Whan
    • International Journal of Advanced Culture Technology
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    • v.7 no.3
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    • pp.120-125
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    • 2019
  • In this paper, we have isolated six phenolic compounds, such as (+)-catechin (1), taxifolin (2), taxifolin-3-O-${\beta}$-D-(+)-xylose (3), quercetin (4), quercetin-3-O-${\alpha}$-L(+)-rhamnose (quercitrin) (5), apigenin-8-C-rhamnosyl-(1'''${\rightarrow}$2'')-glucoside (2''-O-rhamnosylvitexin) (6) from the EtOAc(Ethyl Acetate) and $H_2O$ soluble fractions of Japanese anise(Illicium anisatum L) leaves and twigs. Also, we have evaluated antioxidative and antiviral activity for each isolated compound. The antioxidative test was DPPH (1,1-diphenyl-2-picrylhydrazyl) radical scavenging activity. According to the experimental results, all of the isolated compounds indicated the increased radical scavenging activities as the concentration increases and most of the isolated compounds indicated generally good antioxidative values compare to the controls, ascorbic acid and ${\alpha}$-tocopherol. In the antiviral activities, all of the isolated compounds had no potentials in rhinovirus 1B (HRV 1B). But in enterovirus 71 (EV 71) and Influenza virus A/PR/8 (Influenza PR8), only quercetin (4) indicated the good antiviral activity compare to the control. Based on the above results, we found that the phenolic compounds of Japanese anise may be applied for one of the natural biomass sources that can be used as an antioxidant and an antiviral substance.

Chemical Components and Physiological Activities of Bamboo (Phyllostachys bambusoides Starf) Extracts Prepared with Different Methods (추출방법에 따른 대나무(왕대) 추출물의 화학성분 및 생리활성)

  • Ju, In-Ok;Jung, Gi-Tai;Ryu, Jeong;Choi, Joung-Sik;Choi, Yeong-Geun
    • Korean Journal of Food Science and Technology
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    • v.37 no.4
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    • pp.542-548
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    • 2005
  • Chemical components and physiological activities Bamboo (Phyllostachys bambusoides Starf) extracts obtained by burning, dry heating or extracting with water or 70% ethanol and were investigated. Contents of soluble solid and total phenolic compounds were highest in the ethanol extract. Contents of polyphenols such as catechin, chlorogenic acid, caffeic acid, 3-hydroxy benzoic acid and ferulic acid were determined. Free sugars consisted of galactose, glucose, fructose, and sucrose. Organic acids including citric, tartaric, malic, succinic, and acetic acid were present in the bamboo extracts. Antioxidant activities of dry heat and ethanol extracts were higher than those of BHA or ${\delta}-tocopherol$. Nitrite- scavenging effect of extracts ranged from 84.7 to 99.6% at pH 1.2 ana 3.0. Tyrosinase-inhibitory activity was higher in the water extract, and SOD-like and ACE-inhibitory activity were highest in tile dry kent extract. Antimicrobial activities of the bamboo extracts were strong against Bacillus subtilis, Escherichia coli O157, and Staphylococcus aureus.

Structure Determination of the Extractives from the Taxus Cuspidata Fruits (주목열매 추출물 구조분석)

  • Park, Se-Yeong;Choi, In-Gyu;Bae, Young-Soo
    • Journal of the Korean Wood Science and Technology
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    • v.41 no.6
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    • pp.566-575
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    • 2013
  • The fruits of Taxus cuspidata were collected, divided into seeds and fruits, and extracted with 95% EtOH. The extracts were evaporated under the reduced vacuum pressure, concentrated, then successively fractionated with a series of n-hexane, dichloromethane, ethyl acetate and water on a separatory funnel to get some freeze dried samples. A portion of the EtOAc (arils:1.65 g, seeds:1.04 g) and $H_2O$ (arils:7 g, seeds:10 g) soluble samples were chromatographed on a Sephadex column using MeOH-$H_2O$ (1:1, 1:3, 1:5, v/v), EtOH-hexane (3:1, v/v) mixture and 100% $H_2O$ as eluting solvents to isolate pure compounds from the fractions. The isolates were developed by cellulose TLC using t-BuOH-HOAc-$H_2O$ (TBA; 3:1:1, v/v/v) and 6% aqueous HOAc. Visualization was done under ultraviolet light and by spraying the vanillin-HCl-EtOH reagent (4.8:12:480, v/v/v). followed by heating. The structures of the isolates were characterized by $^1H$- and $^{13}C$-NMR, DEPT, 2D-NMR, LC/MS and EI-MS spectra. In addition to the NMR and MS spectra, acid hydrolysis and permethylation were used to determine the correct structure of the isolated sugar compound. Their structures were elucidated as (+)-catechin (1), (-)-epicatechin (2), (+)-gallocatechin (3), (-)-epigallocatechin (4) and ${\beta}$-D-fructofuranose-($2{\rightarrow}4$)-O-${\beta}$-D-glucopyranose($1{\rightarrow}4$)-O-${\alpha}$-D-glucopyranose ($1{\rightarrow}2$)-O-${\beta}$-D-fructofuranose (5) on the basis of the above experimental evidences.

The Changes of Bioactive Component Concentrations in Different Aged-Peony (Paeonia lactiflora Pall.) Root (작약근(芍藥根) 생육년수(生育年數)에 따른 성분(成分) 함양(含量) 변화(變化))

  • Choung, Myoung-Gun;Kang, Kwang-Hee;Kwack, Young-Ho
    • Korean Journal of Medicinal Crop Science
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    • v.7 no.3
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    • pp.193-199
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    • 1999
  • This study was conducted to establish the standard of quality evaluation in Korean cultivated peony root(Paeoniae Radix). The diameter of fresh root and the concentrations of paeoniflorin, abliflorin and five phenolic compounds at different root ages in Euisung cultivar were investigated. The diameters of fresh root were 5.5mm, 10.3mm, 15.6mm and 19.1mm in one-year, two-year, three-year and four-year-old, respectively. It was also found that the diameter of fresh root was uniformly increased with the increase of root age. The concentrations of paeoniflorin, albiflorin, (+) -catechin and benzoic acid in one-year-old peony root(6.44%, 1.55%, 0.80% and 0.36%, respectively) were higher than those in three-(3.49%, 0.62%, 0.43% and 0.26%) or four-year-old(3.28%, 0.47%, 0.34% and 0.20%). The concentrations of gallic acid, (-) -epicatechin and (+) -taxiforin $3-O-{\beta}-D-glucoside$ were higher in three- (0.26%, 0.09% and 0.26%, respectively) or four-year-old (0.26%, 0.10% and 0.29%) than those in one-year-old (0.25 %, 0.08 % and 0.23 %) by contraries. Excepting (-) -epicatecin, the concentrations of paeoniflorin, albiflorin and four phenolic compounds in the root of unremoved cork layer were higher than those in the root of removed cork layer.

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