• Title/Summary/Keyword: spectroscopic studies

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Phytochemical Studies on Astragalus Root (3);Triterpenoids and Sterols (황기의 성분연구 (3);Triterpenoids and Sterols)

  • Jung, Hye-Sil;Lee, Eun-Ju;Lee, Je-Hyun;Kim, Ju-Sun;Kang, Sam-Sik
    • Korean Journal of Pharmacognosy
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    • v.39 no.3
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    • pp.186-193
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    • 2008
  • Astragali Radix, known as Huangqi, is the most important tonic in the traditional oriental medicine. It reinforces 'qi' (vital energy), strengthens the superficial resistance and promotes the discharge of pus and the growth of new tissue. It has long been used as an anti-perspirant, anti-diuretic or a tonic. Eleven compounds were isolated from the hexane and EtOAc fractions from the roots of Astragalus membranaceus (Leguminosae) and their structures were identified as four triterpenoids [lupenone (1), friedelin (2), lupeol (3), soyasapogenol E (9)] and seven sterols [${\beta}-sitosterol$ (4), stigmastane-3,6-dione (5), $7{\alpha}-hydroxysitosterol$ (6), $5{\alpha},6{\beta}-dihydroxysitosterol$ (7), $7-oxo-{\beta}-sitosterol$ (8), ${\beta}-sitosterol$ glucoside 6'-O-palmitate (10), ${\beta}-sitosterol$ glucoside (11)]. The chemical structures of these compounds were identified on the basis of spectroscopic methods and comparison with literature values. Among these compounds, lupenone (1), friedelin (2), lupeol (3), stigmastane-3,6-dione (5), $7{\alpha}-hydroxysitosterol$ (6), $5{\alpha},6{\beta}-dihydroxysitosterol$ (7), $7-oxo-{\beta}-sitosterol$ (8), soyasapogenol E (9), and ${\beta}-sitosterol$ glucoside 6'-O-palmitate (10) were isolated from this plant for the first time.

Inhibitory Effects of Gallic Acid Isolated from Caesalpinia mimosoides Lamk on Cholangiocarcinoma Cell Lines and Foodborne Pathogenic Bacteria

  • Rattanata, Narintorn;Klaynongsruang, Sompong;Daduang, Sakda;Tavichakorntrakool, Ratree;Limpaiboon, Temduang;Lekphrom, Ratsami;Boonsiri, Patcharee;Daduang, Jureerut
    • Asian Pacific Journal of Cancer Prevention
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    • v.17 no.3
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    • pp.1341-1345
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    • 2016
  • Gallic acid was isolated from Caesalpinia mimosoides Lamk and the structure s identified based on spectroscopic analysis and comparison with authentic compound. In this study we compared the ability of natural gallic acid (nGA) and commercial gallic acid (cGA) to inhibit the proliferation of cholangiocarcinoma cell lines (M213, M214) and foodborne pathogenic bacteria (Salmonella spp. and Plesiomonas shigelloides). Both nGA and cGA had the same inhibitory effects on cell proliferation by inducing apoptosis of cholangiocarcinoma cell lines. In addition, nGA inhibited growth of foodborne pathogenic bacteria in the same manner as cGA. Our results suggest that nGA from Caesalpinia mimosoides Lamk is a potential anticancer and antibacterial compound. However, in vivo studies are needed to elucidate the specific mechanisms involved.

Studies on the Catalytic Effects of Organic Compounds by Polymer-bonded Metalloporphyrins (고분자 결합 Metalloporphyrin을 이용한 유기물질의 산화촉매에 대한 연구)

  • Lee Sung-Ju;Paeng Ki-Jung;Whang Kyu-Ja
    • Journal of the Korean Chemical Society
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    • v.36 no.5
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    • pp.744-752
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    • 1992
  • Polymer bonded metalloporphyrins are synthesized by reaction between Fe(III) protoporphyrin or Mn(II) tetrakis(4-N-carboxyphenyl)porphyrin with polystyrene divinylbenzene copolymer. The spectroscopic properties of synthetic polymer bonded metalloporphyrins are investigated by using resonance Raman spectrometer. By synthetic polymer bonded metalloporphyrins as catalyst, which are model of cytochrome P-450 and peroxidases, epoxidation of olefins and oxidation of alkanes are achieved with H2O2 as oxidant. The catalytic efficiencies with polymer bonded metalloporphyrins are improved on that with corresponding nonpolymer bonded metalloporphyrins. Especially those can be reused because of stability against oxidant. Electron donating imidazole derivatives, which are attached in 5th position of central metal of metalloporphyrins, enhance the catalytic efficiencies.

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Utilization of Biomass Resources(II) Analysis of Polyphenol Components and Antioxidative Activities from Chestnut Inner Bark (Biomass 자원의 활용(II) 율추로부터 폴리페놀 성분의 분석과 항산화활성)

  • Jo, Jong-Soo;Kim, Yun-geun
    • Journal of the Korean Wood Science and Technology
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    • v.33 no.6 s.134
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    • pp.71-78
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    • 2005
  • For the utilization of chestnut inner bark as forest biomass, this studies have been carried out cleary investigated about phenolic compounds from the diethyl ether solubles and ethyl acetate solubles of hot water extract from chestnut inner bark. 3 compound were isolated and their structures were identified by spectroscopic methods. They were known compounds, 3,5-dihydroxybenzoic acid, 3,4,5-trihydrixybenzoic acid and catechin. Electron donating ability (EDA) of 3 compounds were investigated. Gallic acid and catechin were found to higher EDA than control, ascorbic acid and $\alpha$-tocopherol in 10 ppm, and especially gallic acid has very higher EDA, 21 times than ascorbic acid. This gallic acid of chemical structure were substituted with free phenolic hydroxyl groups at meta and para position. It was supposed that phenolic hydroxyl groups in chemical structure was a EDA factor.

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

  • Kwon, Dong-Joo;Kim, Jin-Kyu;Bae, Young-Soo
    • Journal of the Korean Wood Science and Technology
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    • v.39 no.1
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    • pp.104-112
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    • 2011
  • There have been few reports on the constituents and biological activity of stem bark of $Acer$ $tegmentosum$, and no phytochemical and biological studies have been reported for stem wood of $A.$ $tegmentosum$. Two flavan 3-ols (1 and 2), three phenolic acid/alcohols (3~5), and two coumarins (6 and 7) were isolated from the stem wood of $A.$ $tegmentosum$ by repeated column chromatography. The structure of isolated compounds were identified as (+)-catechin (1), (-)-epicatechin (2), $p$-hydroxybenzaldehyde (3), syringic alcohol (4), $p$-tyrosol (5), scopoletin (6), and cleomiscosin A (7) on the basis of spectroscopic evidences such as $^1H$-NMR, $^{13}C$-NMR, 2D-NMR and MS spectrum. $p$-Hydroxybenzaldehyde (3), syringic alcohol (4), scopoletin (6), and cleomiscosin A (7) have not been reported from this plant so far. (+)-Catechin (1) and (-)-epicatechin (2) showed the higher 1, 1-diphenyl-2-picrylhydrazyl (DPPH) radical scavenging activity than butylated hydroxyanisole (BHA) used as a positive control.

Biochemical and Cellular Investigation of Vitreoscilla Hemoglobin (VHb) Variants Possessing Efficient Peroxidase Activity

  • Isarankura-Na-Ayudhya, Chartchalerm;Tansila, Natta;Worachartcheewan, Apilak;Bulow, Leif;Prachayasittikul, Virapong
    • Journal of Microbiology and Biotechnology
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    • v.20 no.3
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    • pp.532-541
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    • 2010
  • Peroxidase-like activity of Vitreoscilla hemoglobin (VHb) has been recently disclosed. To maximize such activity, two catalytically conserved residues (histidine and arginine) found in the distal pocket of peroxidases have successfully been introduced into that of the VHb. A 15-fold increase in catalytic constant ($k_{cat}$) was obtained in P54R variant,which was presumably attributable to the lower rigidity and higher hydrophilicity of the distal cavity arising from substitution of proline to arginine. None of the modifications altered the affinity towards either $H_2O_2$ or ABTS substrate. Spectroscopic studies revealed that VHb variants harboring the T29H mutation apparently demonstrated a spectral shift in both ferric and ferrous forms (406-408 to 411 nm, and 432 to 424-425 nm, respectively). All VHb proteins in the ferrous state had a $\lambda_{soret}$ peak at ~419 nm following the carbon monoxide (CO) binding. Expression of the P54R mutant mediated the downregulation of iron superoxide dismutase (FeSOD) as identified by two-dimensional gel electrophoresis (2-DE) and peptide mass fingerprinting (PMF). According to the high peroxidase activity of P54R, it could effectively eliminate autoxidation-derived $H_2O_2$, which is a cause of heme degradation and iron release. This decreased the iron availability and consequently reduced the formation of the $Fe^{2+}$-ferric uptake regulator protein ($Fe^{2+}$-Fur), an inducer of FeSOD expression.

Radical Scavenging Constituents of Cyperus flaccidus

  • Ahn, Dal-Rae;Lee, Hyun-Jin;Xing, Ming Ming;Tao, Chao;Lee, Eun-Byeol;Lee, Tae-Gwan;Shin, Tae-Yong;Eun, Jae-Soon;Jeon, Hoon;Lim, Jong-Pil;Kim, Dae-Keun
    • Natural Product Sciences
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    • v.18 no.2
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    • pp.111-115
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    • 2012
  • In the course of screening for antioxidant compounds by measuring the DPPH (1,1-diphenyl-2-picrylhydrazyl) radical scavenging effect and superoxide quenching activity, methanol extract of Cyperus flaccidus (Cyperaceae) was found to show potent antioxidant activities. Subsequent activity-guided fractionation of the methanolic extract led to the isolation of ten compounds, kaempferol-3,7-O-${\alpha}$-L-dirhamnopyranoside (1), caffeic acid (2), quercetin-3-O-${\alpha}$-L-rhamnopyranosyl($1{\rightarrow}6$)-${\beta}$-D-glucopyranoside (3), kaempferol-3-O-${\alpha}$-L-rhamnopyranoside (4), quercetin-3-O-${\alpha}$-L-rhamnopyranoside (5), luteoiln-7-O-${\beta}$-D-glucopyranoside (6), kaempferol-3-O-${\alpha}$-L-rhamnopyranosyl($1{\rightarrow}6$)-${\beta}$-D-glucopyranoside (7), luteoiln (8), quercetin (9) and quercetin-3-O-${\beta}$-D-glucuronide (10). Their structures were elucidated by spectroscopic studies. Compounds 1 - 10 were isolated for the first time from this plant. Among them, compounds 2, 8 and 9 showed the significant radical scavenging effects on DPPH, and the potent xanthine-originated superoxide quenching activities.

Phenolic Constituents from the Flowers of Hamamelis japonica Sieb. et Zucc.

  • Yim, Soon-Ho;Lee, Young Ju;Park, Ki Deok;Lee, Ik-Soo;Shin, Boo Ahn;Jung, Da-Woon;Williams, Darren R.;Kim, Hyun Jung
    • Natural Product Sciences
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    • v.21 no.3
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    • pp.162-169
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    • 2015
  • Hamamelis japonica (Hamamelidaceae), widely known as Japanese witch hazel, is a deciduous flowering shrub that produces compact clumps of yellow or orange-red flowers with long and thin petals. As a part of our ongoing search for phenolic constituents from this plant, eleven phenolic constituents including six flavonol glycosides, a chalcone glycoside, two coumaroyl flavonol glycosides and two galloylated compounds were isolated from the flowers. Their structures were elucidated as methyl gallate (1), myricitrin (2), hyperoside (3), isoquercitrin (4), quercitrin (5), spiraeoside (6), kaempferol 4'-O-β-glucopyranoside (7), chalcononaringenin 2'-O-β-glucopyranoside (8), trans-tiliroside (9), cis-tiliroside (10), and pentagalloyl-O-β-D-glucose (11), respectively. These structures of the compounds were identified on the basis of spectroscopic studies including the on-line LCNMR-MS and conventional NMR techniques. Particularly, directly coupled LC-NMR-MS afforded sufficient structural information rapidly to identify three flavonol glycosides (2 - 4) with the same molecular weight in an extract of Hamamelis japonica flowers without laborious fractionation and purification step. Cytotoxic effects of all the isolated phenolic compounds were evaluated on HCT116 human colon cancer cells, and pentagalloyl-O-β-D-glucose (11) was found to be significantly potent in inhibiting cancer cell growth.

Free Radical Scavengers of Taxillus delavayi (Van Tiegh.) Danser. (류수기생(柳樹奇生)의 라디칼 소거활성 성분)

  • Lee, Chung Hak;Ahn, Dalrae;Cui, Xun;Yang, Jae-Heon;Lee, Eun Byeol;Xing, Ming Ming;Tao, Chao;Shin, Tae-Yong;Cho, Chong Hyeon;Lee, Jae Hyeok;Park, Jeong-Suk;Kim, Dae Keun
    • Korean Journal of Pharmacognosy
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    • v.43 no.4
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    • pp.297-301
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    • 2012
  • In the course of screening for antioxidant compounds by measuring the radical scavenging effect on 1,1-diphenyl-2-picrylhydrazyl (DPPH), a total extract of the twigs of Taxillus delavayi (Loranthaceae) was found to show potent radical scavenging activity. Subsequent activity-guided fractionation of the methanolic extract led to the isolation of two phenolic compounds, catechin (1) and galloyl catechin (2), as active principles. Their structures were elucidated by spectroscopic studies. These two compounds showed the significant antioxidative effects on DPPH, and riboflavin- and xanthin-originated superoxide quenching activities. And these two compounds also showed strong nitric oxide radical scavenging effects. In riboflavin- and xanthin-originated superoxide quenching activities and nitric oxide radical scavenging effect, compound 2 showed better antioxidant activities than vitamin C.

Studies on the Chemical Constituents from the Seeds of Zizyphus jujuba var. inermis

  • Lee, Nam Kyung;Shin, Hyun Jung;Kim, Wan-Seok;In, Gyo;Han, Chang Kyun
    • Natural Product Sciences
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    • v.23 no.4
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    • pp.258-264
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    • 2017
  • This study analyzed the seeds of Zizyphus jujuba var. inermis commonly used as a remedy in traditional Chinese medicine, in order to determine its various biologically active compounds. Through process 3-pentadecylcatechol, ${\rho}$-menth-8-ene, and ${\gamma}$-bisabolene were isolated and identified for the first time which are urushiol, monoterpenoidal, and sesquiterpenoidal compounds, respectively. Also, found were another sesquiterpenoidal compounds, vomifoliol, and four steroidal compounds, ${\beta}$-sitosterol, stigmasterol, stigmasta-5,23-dien-$3{\beta}$-ol, and stigmast-4-en-3-one. In addition, fourteen triterpenoidal compounds were isolated and identified. These were lupeol, betulinic acid, betulinaldehyde, alphitolic acid, 3-O-cis-${\rho}$-coumaroyl-alphitolic acid, 3-O-trans-${\rho}$-coumaroyl-alphitolic acid, 2-O-cis-${\rho}$-coumaroyl-alphitolic acid, 2-O-trans-${\rho}$-coumaroyl-alphitolic acid, zizyberanalic acid, ceanothic acid, oleanolic acid, maslinic acid, 3-O-cis-${\rho}$-coumaroyl-maslinic acid, and 3-O-trans-${\rho}$-coumaroyl-maslinic acid. The structures were identified by comparing of the spectroscopic experiments, NMR and MS, and then compared that reported data, respectively. Three extracts of water, methanol, and chloroform from the seeds showed a weak anti-proliferative effect, anti-microbial activity, and anti-oxidant effect, respectively.