• Title/Summary/Keyword: silica gel column chromatography

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Anti-complement Activity of Triterpenoids from the Whole Plant of Patrinia saniculaefolia

  • An, Ren-Bo;Na, Min-Kyun;Min, Byung-Sun;Lee, Hyeong-Kyu;Bae, Ki-Hwan
    • Natural Product Sciences
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    • v.14 no.4
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    • pp.249-253
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    • 2008
  • Two oleanane-type triterpenes (1, 2) and their glycosides (4-6), and one ursane-type triterpene (3) have been isolated from a methanolic extract of Patrinia saniculaefolia Hemsley (Valerianaceae) through repeated silica gel and reversed-phase C-18 column chromatography. Their chemical structures were determined as oleanolic acid (1), oleanonic acid (2), 23-hydroxyursolic acid (3), 3-O-${\alpha}$-L-arabinopyranosyl-oleanolic acid (4), 3-O-${\beta}$-D-glucopyranosyl-oleanolic acid (5), and oleanolic acid 3-O-[${\alpha}$-D-xylopyranosyl-($1{\rightarrow}3$)-${\beta}$-D-glucuronopyranoside-6-O-butyl-ester] (6) on the basis of their MS, $^1H$-, and $^{13}C$-NMR spectral data. All compounds were isolated from the whole plant of the P. saniculaefolia for the first time. These compounds were examined for their anti-complement activity against the classical pathway of the complement system. Among them, compounds 1 - 3 exhibited anti-complement activity with $IC_{50}$ values of 470.1, 212.2, and 121.0 ${\mu}M$, respectively, whereas compounds 4 - 6 were inactive. These results suggest that the carbonyl or hydroxy group at C-3 in the oleananeand/or ursane-triterpenes are important for the anti-complement activity against the classical pathway.

Neuroprotective Activity of Phytosterols Isolated from Artemisia apiacea (청호의 Phytosterol 성분 분리 및 뇌세포 보호 활성)

  • Lee, Jiwoo;Weon, Jin Bae;Ma, Choong Je
    • Korean Journal of Pharmacognosy
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    • v.45 no.3
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    • pp.214-219
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    • 2014
  • Artemisia apiacea is a traditional herbal medicine using treatment of eczema and jaundice in Eastern Asia including China, Korea, and Japan. In this study, the three phytosterol constituents were isolated and identified from the hexane fraction of 80% aqueous methanol extract of A. apiacea. Compounds were isolated using open column chromatography (silica gel). Their chemical structures were also established using $^1H$-NMR and $^{13}C$-NMR. Moreover, neuroprotective activity of each compound against glutamate-induced neurotoxicity in hippocampal HT-22 cell line was evaluated by 3-(4,5-dimethylthiazol-2-yl)-2,5-diphenyltetrazolium bromide (MTT) assay. Furthermore, Inhibition of reactive oxygen species (ROS) and calcium ion ($Ca^{2+}$) accumulation were measured for elucidation of neuroprotective mechanism of isolated compounds. They showed that stigmasterol had neuroprotective activity against the glutamate-induced toxicity by inhibition of ROS and $Ca^{2+}$ production. In conclusion, isolated compound of A. apiacea might be useful for therapeutic agent against neurodegenerative diseases.

Inhibition of HBV ]Replication by the Extract of Phyllanthus ussuriensis (여우주머니(Phyllanthus ussuriensis) 추출물의 B헝 간염바이러스 증식 억제)

  • Kim, Chul-Young;Kim, Jeong-Min;Kim, Tae-Gyun;Kim, Seung-Hee;Huh, Hoon
    • Biomolecules & Therapeutics
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    • v.6 no.2
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    • pp.139-144
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    • 1998
  • Abstract -Phyllanthus ussuriensis which belongs to Euphorbiaceae has been used as a component of Korean traditional remedy against hepatitis and jaundice. Aqueous methanolic extract of P. ussuriensis was tested for antiviral activity of hepatitis B virus (HBV) in HepG2 2.2.15 cells which were derived through transfection of cloned HBV DNA into HepG2 human hrpatoblastoma cells. P. ussuriensis extract decreased the levels of extracellular HBV virion DNA and inhibited HBV replication at concentrations ranging from 50 to 500$\mu$g/ml. Partitioning of water suspension of the extract revealed that the activity mainly resides in the EtOAc fraction. Consecutive purification of the EtOAc fraction by silica-gel column chromatography resulted in the two active anti-HBV fractions. Southern blot analysis shows that the action mechanisms or active site of the two fractions seems to be different in terms of their inhibition of HBV replication steps.

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Isolation and Characterization of Antitumor Agents from Dictamnus albus

  • Kim, Se-Won;Yeo, Woon-Hyung;Ko, Young-Su;Kim, Si-Kwan
    • Korean Journal of Pharmacognosy
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    • v.28 no.4
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    • pp.209-214
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    • 1997
  • This study was carried out to find new antitumor agents from plant resource. Three cytotoxic agents were isolated from the root of Dictamnus albus by hexane extraction, silica gel column chromatography and HPLC. They were identified to be dictamnine $(C_{12}H_9NO_2)$, preskimmianine $(C_{17}H_{21}NO_4)$ and fraxinellone $(C_{14}H_{16}O_3)$ on the basis of spectroscopic evidences. In this study, it was newly found that these compounds possess a cytotoxic activity against lung lymphoma L1210 cell line. Among them. Preskimmianine was the most potent against the lymphoma L1210 with a $IC_{50}$ of $3.125\;{\mu}g/ml\;(10.3\;{\mu}M)$. Toxicity of preskimmianine against normal Iymphocyte was observed at the concentration of $50\;{\mu}g/ml\;(165\;{mu}M)$. These results support the pharmacological role of D. albus, a herb known as Paeksun in Korea and used as an anticancer agent in folk medicine.

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Screening for Antioxidant Activity of Plants and Marine Algae and Its Active Principles from Prunus davidiana

  • Choi, Jae-Sue;Lee, Ji-Hyeon;Park, Hae-Jin;Kim, Hyung-Geun;Young, Han-Suk;Mun, Sook-Im
    • Korean Journal of Pharmacognosy
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    • v.24 no.4
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    • pp.299-303
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    • 1993
  • The antioxidant activity of methanol extracts of plants and marine algae was tested by using 1,1-diphenyl-2-picrylhydrazyl(DPPH). Five plant extracts(Prunus davidiana, Eriobotrya japonica, Artemisia iwayomogi, Stirodella tolyrrhiza and Ulmus davidiana) and two algae (Ecklonia stolonifera and Symphycoladia latiuscula) were found to be the most effective in DPPH radical scavenging activity. The methanol extract obtained from the stems of Prunus davidiana was fractionated with several solvents. The ethylacetate soluble fraction exhibiting the strongest antioxidant activity was further purified by repeated silica gel and Sephadex LH-20 column chromatography. Antioxidant flavonoids and flavonoid glycosides were isolated and the most active ones was identified as (+)-catechin by MS, $^1H-NMR$ and $^{13}C-NMR$. Its antioxidant activity was higher than that oil vitamin C.

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Isolation and Identification of Antimicrobial Compound from Sancho (Zanthoxylum Schinifolium) (산초로부터 항균성 화합물의 분리 및 동정)

  • 김순임;한영실
    • Korean journal of food and cookery science
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    • v.13 no.1
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    • pp.56-63
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    • 1997
  • Antimicrobial activity of Sancho (Zanthoxylum schinifolium) was investigated. Methanol extract of dried Sancho was fractionated to hexane, chloroform, ethylacetate, butanol, and aqueous fractions. Chloroform fraction among these fractions showed the highest inhibitory effect on the microorganisms such as Escherichia coli, Bacillus subtilis, Staphylococcus aureus and Lactobacillus plantarum at 1000 $\mu\textrm{g}$/$m\ell$. Chloroform fraction was further fractionated into 4 fractions by silica gel column and thin layer chromatography (TLC). The fraction 3 on TLC exhibited the highest antimicrobial activity. In the 2nd fractionation, subfration 2 was identified as hexadecanoic acid by MS, $^1$H-NMR and IR.

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Evaluation on the Safety of ${\gamma}$-Irradiated Angelica gigas Nakai: Stability of Active Components and Safety in Genotoxicity Test (감마선 조사 당귀(Angelica gigas Nakai)의 유효성분 안정성 및 유전독성학적 안전성 연구)

  • 조성기;유영법
    • Journal of the Korean Society of Food Science and Nutrition
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    • v.29 no.2
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    • pp.300-306
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    • 2000
  • In the present studies, we assessed the stability of active components and toxicological safety of irradiated Angelica gigas Nakai(Danggui). In order to confirm the stability of active components in the ${\gamma}$-irradiated roots of Danggui, the quantitative analysis of decursin and decursinol angelate of ${\gamma}$-irradiated sample was carried out by high performance liquid chromatographic (HPLC) methods using reverse phase columns and normal phase columns. From the root of Danggui, decursin and decursinol angelate were isolated by a silica gel column chromatography(toluene : ether (1 : 1), Hexane : EtOAc(15 : 1)). And then the structures were confirmed in the 1H and 13C-NMR analysis. The HPLC chromatograms of decursin and decursinol angelate in ${\gamma}$-irradiated Danggui were similar with those of non-irradiated sample. In the examination of in vitro genotoxicity of the water extract from ${\gamma}$-irradiated Danggui using Salmonella reversion assay(Ames test) and micronucleus test in Chinese hamster ovary (CHO) cells, mutagenicity was not exhibited in the two assays with or without metabolic activation. These resutls suggest that active components in the ${\gamma}$-irradiated Danggui should be stable and that the safety of ${\gamma}$-irradiated Danggui could be revealed in further test in vivo.

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Inhibitory Effect of Mugwort(Artemisia asiatica Nakai) on the Growth of Food Spoilage Microorganisms and Identification of Antimicrobial Compounds

  • Kim, Soon--Im;Park, Hye-Jin;Han, Young-Sil
    • Preventive Nutrition and Food Science
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    • v.1 no.1
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    • pp.59-63
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    • 1996
  • The antimicrobial activity of mugwort(artemisia asiatica Nakai) was investigated. The methanol extract or dried mugwort was fractionated to hexane, chloroform, ethylacetate, butanol, and aqueous fractions. The hexane fraction among these fractions showed the hifhest inhibitory effect on the growth of microorganisms such as Bacillus subtilis, Escherichia coli, Staphylococcus aureus and Lactobacillus plantarum. Bacillus subtilis, Escherchia coli, and Staphylococcus aureus were completely inhibited at a concentration of 250, 500 , and 750$\mu\textrm{g}$/ml respectively. The hexane fraction was further fractionated into 16 subfractions by silica gel column and thin layer chromatography(TLC). The subfraction No. 8, 9, and 10 on TLC exhibited high antimicrnial activity. At 3rd fractionation, subfraction No. 2 inhibited the growth of microorganisms at 500$\mu\textrm{g}$/ml. Heptadecane, dodecamethyi cyclohexasiloxane, (E,E)-2,4-decadienal, dodecamethul pentasiloxane, coumarin, 5,6,6,6a-tetrahydro-4,4,7a-trimethyl-2(4H)-benzofuranone, neophytadiene, tridecanoic acid, methyl ester, 2-methyl-4,5-nonadiene, (Z,Z)-9-12-octadecadienoyl chloride, and bis(2-ethylhexyl) were identified from this antimicrobial fraction by GC-MS.

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Cytotoxic and COX-2 Inhibitory Constituents from the Aerial Parts of Aralia cordata

  • Lee, Ik-Soo;Jin, Wen-Yi;Zhang, Xin-Feng;Hung, Tran-Manh;Song, Kyung-Sik;Seong, Yeon-Hee;Bae, Ki-Hwan
    • Archives of Pharmacal Research
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    • v.29 no.7
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    • pp.548-555
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    • 2006
  • Three diterpenes (1, 8, and 9), three triterpenes (3, 4, and 7), one saponin (11), four sterols (2, 5, 6, and 12), and one cerebroside (10) were isolated from the EtOH extract of the aerial parts of Aralia cordata by repeated silica gel column chromatography. Their chemical structures were identified by comparing their physicochemical and spectral data with those published in literatures. All isolated compounds were evaluated for their cytotoxicity against L1210, K562, and LLC tumor cell lines using MTT assay. Of which, $3{\beta},5{\alpha}-dihydroxy-6{\beta}-methoxyergosta-7,22-diene$ (6) showed a potent cytotoxicity against all cell lines with $IC_{50}$ values of 11.7, 11.9, and $15.1\;{\mu}M$, respectively, while compounds 1, 5, and 11 showed a moderate or weak cytotoxicity. These isolates were also examined for their inhibitory activity against COX-1 and COX-2. Although most compounds, except for 2, 10, and 12, showed a strong inhibitory activity against COX-1, they exhibited a moderate or weak inhibitory activity against COX-2.

Phytochemical constituents from the aerial parts of Salvia plebeia

  • Paje, Leo Adrianne;Lee, Hak-Dong;Choi, Jungwon;Kim, Juree;Kim, Ki Hyun;Yu, A Ram;Bae, Min-Jung;Lee, Sanghyun
    • Journal of Applied Biological Chemistry
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    • v.64 no.4
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    • pp.391-397
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    • 2021
  • Four compounds were isolated from Salvia plebeia aerial parts. Silica gel open column chromatography with a gradient elution system was used to isolate and purify these compounds. Nuclear magnetic resonance spectroscopy and mass spectroscopy were used for structural elucidation and identification, while electronic circular dichroism was used to confirm the absolute configuration. The structures were determined to be 𝛽-sitosterol (1), (-)-1S,5S,8S,10R-1-acetoxy-8-hydroxy-2-oxoeudesman-3,7(11)-dien-8,12-olide (2), ursolic acid (3), and N-methylhydroxylamine (4). Compounds 2 and 4 were isolated for the first time from this plant. Compound 2 was quantitatively analyzed via HPLC/UV. The results showed that the methanol extract of S. plebeia had a higher content of compound 2 (1.20 mg/g) than the ethanol extract (0.55 mg/g). This study could be used as a preliminary step in conducting HPLC/UV analysis of sesquiterpenoids in S. plebeia extract to assess their bioavailability and potency.