• 제목/요약/키워드: Spectroscopic studies

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

  • 정혜실;이은주;이제현;김주선;강삼식
    • 생약학회지
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    • 제39권3호
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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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    • 제17권3호
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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.

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

  • 이승주;팽기정;황규자
    • 대한화학회지
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    • 제36권5호
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    • pp.744-752
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    • 1992
  • 철(III) protoporphyrin과 망간(II) tetrakis(4-N-carboxyphenyl) Porphyrin을 polystyrene divinylbenzene 공중합체 수지와 반응시켜 고분자결합 금속포피린을 합성하였다. 고분자와 결합된 포피린은 공명라만분광기를 이용, 합성과정에서 포피린과 중심금속의 산화상태 등 여러가지 화학적 성질이 변화되지 않았음으로 확인하였다. 합성된 고분자결합 금속포피린은 싸이토크롬 P-450과 같은 산화촉매효소의 모형화합물로서 과산화수소에 의한 olefin의 epoxidation과 alkane의 oxidation의 촉매로서 사용이 가능하였다. 그 효율은 고분자와 결합하지 않은 동종의 포피린에 비하여 현저히 증가되었으며, 특히 포피린이 산화제에 의해 분해되지 않아 재사용이 가능하였다. 실제 효소에서와 같이 imidazole 유도체와 같은 전자주게 배위자가 포피린 중심금속에 배위한 경우 촉매효과가 더욱 향상되었다.

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

  • 조종수;김윤근
    • Journal of the Korean Wood Science and Technology
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    • 제33권6호통권134호
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    • pp.71-78
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    • 2005
  • 임산바이오매스 자원 이용의 일환으로 율추(栗皺) 열수추출물의 디에틸에테르 가용부 및 초산에틸 가용부로부터 칼럼크로마토그래피 등을 이용하여 3종의 물질을 단리하여 화학구조를 동정한 결과, 3,5-dihydroxybenzoic acid, 3,4,5-trihydroxybenzoic acid 그리고 (+)-catechin을 확인하였다. 이들 단리화합물의 항산화활성을 DPPH 라디칼 전자공여능(EDA)으로 측정한 결과, 10 ppm에서 화합물 3,4,5-trihydroxybenzoic acid (gallic acid)와 (+)-catechin은 대조구인 ascorbic acid와 $\alpha$-tocopherol 보다 높게 나타났고, 특히 화합물 gallic acid는 ascorbic acid보다 약 21배, $\alpha$-tocopherol보다 약 6배 높게 나타났으며 화합물 catechin보다 약 2.7배 높게 나타났다.

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.

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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    • 제20권3호
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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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    • 제18권2호
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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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    • 제21권3호
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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.

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

  • 이청학;안달래;최훈;양재헌;이은별;형명명;도초;신태용;조종현;이재혁;박정숙;김대근
    • 생약학회지
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    • 제43권4호
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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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    • 제23권4호
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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.