• Title/Summary/Keyword: 2-D NMR

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Phytochemical and pharmacological evaluation of the flowers of Sarcostemma brevistigma Wight

  • Lalitha, KG;Sethuraman, MG
    • Advances in Traditional Medicine
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    • v.9 no.3
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    • pp.252-258
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    • 2009
  • Shade-dried flowers of Sarcostemma brevistigma Wight Syn (SBF) belonging to Asclepiadaceae yielded a rare flavonol glycoside viz., Quercetin 5a prenyl, 3-O-glucosyl, 7-O-(4c-p-coumaroyl) neohesperidoside which were characterized based on chemical and spectral (including 2D NMR) studies. The ethyl acetate fraction of alcoholic concentrate (test sample) of flowers of this plant (SBF) was evaluated for its hepatoprotective and inhibition of lipid peroxidation activities to investigate the scientific basis of the traditional uses. The oral administration in varying doses viz., 125 and 250 mg/kg of aqueous suspension of SBF to rats for 7 days produced significant (P < 0.01) hepatoprotective effect comparable to that of standard drug silymarin. The SBF afforded good hepatoprotection against $CCl_4$ induced elevation levels of serum marker enzymes, serum bilirubin and liver weight. The free radical scavenging effects of SBF and flavonol glycoside (SA) were assigned by $Fe^{2+}$/ascorbate induction method (in vitro), which revealed the inhibition of lipid peroxidation. The SBF and SA showed prominent anti-lipid peroxidation activity ($IC_{50}$ about $\sim$180 mg/ml and 11.0 mg/ml respectively), which was comparable to standard drug curcumin ($IC_{50}$ about $\sim$8.25 mg/ml). Thus the hepatoprotective activity of SB could be correlated to the free radical scavenging property of the flavonol glycoside.

Isolation of Dibromosceptrin with Antimalarial Activity from the Unidentified Sponge, Agelas sp. (Agelas속의 미동정 해면으로부터 항말라리아 활성을 갖는 Dibromosceptrin의 분리)

  • Park, Yeung-Beom;Lee, Jong-Soo;Lim, Chi-Won
    • Korean Journal of Pharmacognosy
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    • v.35 no.3 s.138
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    • pp.189-193
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    • 2004
  • In order to find some lead compounds for the treatment of opportunistic infections of malaria and pathogenic microbes, an undescribed Indonesian sponge Agelas sp. collected at Manado, Indonesian Waters, was suggested containing active compounds. Crude ethanolic extract of the sponge exhibited significant in vitro antimalarial and antimicrobial activity against Plasmodium falciparum (D6 colne) with $IC_{5O}$ values of $8\;{\mu}/ml$ and against pathogenic microbes such as Candida albicans $(150\;{\mu}/ml)$, Cryptococcus neoformans $(<20\;{\mu}/ml)$, Staphylococcus aureus $25\;{\mu}/ml$, methicillin-resistant Staphylococcus aureus $(<20\;{\mu}/ml)$, and Pseudomonas aeruginosa $(<20\;{\mu}/ml)$. Active compound (5.0 mg) was isolated from the ethanolic extracts of the sponge and purified by using silica gel and ODS column, successively. Active compound was elucidated as dibromosceptrin $(C_{22}H_{24}Br_2N_{10}O_2)$ by detailed analysis of FTESI-MS and comparison of $^1H,\;^{13}C$, DEPT and HMQC NMR spectral data with those reported.

Sesquiterpene-Neolignans from the Stem Bark of Magnolia obovata and Their Cytotoxic Activity

  • Youn, Ui-Joung;Chen, Quan Cheng;Lee, Ik-Soo;Kim, Hong-Jin;Hung, Tran Manh;Na, Min-Kyun;Lee, Jong-Pill;Min, Byung-Sun;Bae, Ki-Hwan
    • Natural Product Sciences
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    • v.14 no.1
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    • pp.51-55
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    • 2008
  • Three sesquiterpene-lignans, eudeshonokiol B (1), eudesobovatol B (2), and clovanemagnolol (3), were isolated from the stem bark of Magnolia obovata, together with magnolol (4), honokiol (5), and obovatol (6) on the basis of spectroscopic and physicochemical analyses including 2D NMR and Mass. Compounds 1 - 3 were belongs to a unique class of natural products made up of a sesquiterpene and biphenyl-type neolignan via an ether bond. All the isolated compounds were tested in vitro for their cytotoxic activity against the HeLa, A549, and HCTll6 cancer cell lines. Compounds 1 - 6 showed the cytotoxic activity against tested cancer cell lines, with $IC_{50}$ values ranging from 7.1 to 14.4 ${\mu}g/mL$.

Antioxidant Components from Broussonetia kazinoki (닥나무 뿌리껍질의 항산화 성분)

  • Lee, Hwa-Jin;Park, Jae-Hyun;Jang, Dong-Il;Ryu, Jae-Ha
    • YAKHAK HOEJI
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    • v.41 no.4
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    • pp.439-443
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    • 1997
  • From the root bark of Broussonetia kazinoki (Moraceae) two antioxidant components were identified. Their structures were determined as kazinol A (1) and kazinol E (2) (is oprenylated flavan and isoprenylated 1,3-diphenyl propan derivatives) by comparing NMR data with those of the reported compounds from relative plants. The antioxidant activity of 1 and 2 were monitored by the method of DPPH radical scavenging activity, whose $SC_{50}$ values were $41.4{\mu}M\;and\;33.4{\mu}M$, respectively. These compounds also exhibited inhibitory activity against tyrosinase, which is the sole key enzyme for the melanin biosynthesis and play a role in conversion of tyrosine to dopa, and dopa to dopaquinone. The antioxidant effect and the suppression of melanin biosynthesis are useful for anti-aging, increasing vitality in the incidence of major degenerative diseases, and cosmetic products in relation to hyperpigmentation.

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Diels-Alder Type Adducts from Hairy Root Cultures of Morus macroura

  • Happyana, Nizar;Hakim, Euis H.;Syah, Yana M.;Kayser, Oliver;Juliawaty, Lia D.;Mujahidin, Didin;Ermayanti, Tri M.;Achmad, Sjamsul A.
    • Natural Product Sciences
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    • v.25 no.3
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    • pp.233-237
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    • 2019
  • Three Diels-Alder type adducts, guangsangon E (1), chalcomoracin (2) and sorocein I (3) were isolated from hairy root cultures of Morus macroura. The structures of the isolated compounds (1-3) were determined by spectroscopic method (NMR and MS), and spectral comparison to literature. Cytotoxic activities of the isolated compounds (1 - 3) were investigated against P-388 murine leukemia cell line. Guangsangon E (1) showed the most potent cytotoxicity against P-388 murine leukemia cell line with $IC_{50}$ value of $2.75{\pm}0.32{\mu}g/mL$. To the best of our knowledge, guangsangon E (1) and sorocein I (3) were reported for the first time from the tissue cultures of M. macroura.

Isolation and Identification of Phenolic Compounds from the Root Bark of Morus alba L. (상백피(Morus alba root barks)로부터 페놀화합물의 분리 및 동정)

  • Jung, Jae-Woo;Park, Ji-Hae;Seo, Kyeong-Hwa;Baek, Yoon-Su;Oh, Eun-Ji;Lee, Dae-Young;Lim, Dong-Wook;Han, Daeseok;Baek, Nam-In
    • Journal of Applied Biological Chemistry
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    • v.58 no.2
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    • pp.153-155
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    • 2015
  • The root barks of Morus alba L. were extracted with 80% aqueous MeOH, and the concentrated extract was partitioned with EtOAc, n-BuOH, and $H_2O$ fractions. The repeated silica gel, octadecyl silica gel, and Sephadex LH-20 column chromatographies of the EtOAc and n-BuOH fractions led to isolation of four phenolic compounds. The chemical structures of the compounds were determined as norartocarpanone (1), 2',4',7-trihydroxy-(2S)-flavanone (2), methyl ${\beta}$-resorcylate (3), and (Z)-oxyresveratrol-4-O-${\beta}$-$\small{D}$-glucopyranoside (4). Compound 4 was isolated for the first time from the root barks of M. alba L.

Chemical Constituents from the Stony Coral Alveopora japonica

  • Youn, Ui-Joung;Lee, Yoo-Jin;Jeon, Ha-Rim;Shin, Hyun-Ji;Son, Young-Min;Nam, Joo-Won;Han, Ah-Reum;Song, Jun-Im;Won, Yong-Jin;Seo, Eun-Kyoung
    • Natural Product Sciences
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    • v.17 no.1
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    • pp.1-4
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    • 2011
  • Chemical investigations of the stony coral Alveopora japonica Eguchi (Poritidae) resulted in the isolation of four known compounds (1 - 4). The structures of 1 - 4 were identified as a sterol, ergosta-5,24(28)-dien-$3{\beta}$-ol (1), a mixture of monoacyl glycrols (2), eicosanoic acid and tetracosanoic acid, and two nucleosides, thymine (3) and 2'-deoxythymidine (4), respectively, on the basis of spectroscopic and physicochemical analyses including 1D- and 2D- NMR techniques as well as by comparison of their data with the published values. Compounds 1 - 4 were isolated from this species for the first time. Moreover, these compounds (1 - 4) were found in the genus Alveopora and the family Poritidae for the first time.

All-trans Retinoic Acid-Associated Low Molecular Weight Water-Soluble Chitosan N anoparticles Based on Ion Complex

  • Kim Dong-Gon;Choi Changyong;Jeong Young-Il;Jang Mi-Kyeong;Nah Jae-Woon;Kang Seong-Koo;Bang Moon-Soo
    • Macromolecular Research
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    • v.14 no.1
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    • pp.66-72
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    • 2006
  • The purpose of this study is to develop novel nanoparticles based on polyion complex formation between low molecular weight water-soluble chitosan (LMWSC) and all-trans retinoic acid (atRA). LMWSC nanoparticles encapsulating atRA based on polyion complex were prepared by mixing of atRA into LMWSC aqueous solution using ultrasonication. In FTIR spectra, the carbonyl group of atRA at 1690 $cm^{-1}$ disappeared or decreased when ion complexes were formed between LMWSC and atRA. In ${1}^H$ NMR spectra, specific peaks of atRA disappeared when atRA-encapsulated LMWSC (RAC) nanoparticles were reconstituted into $D_{2}O$ while specific peaks both of atRA and LMWSC appeared in $D_{2}O$/DMSO (1/3, v/v) mixture. XRD patterns also showed that the crystal peaks of atRA were disappeared by encapsulation into LMWSC nanoparticles. LMWSC nanoparticles encapsulating atRA have spherical shapes with particle size below 200 nm. The mechanism of encapsulation of atRA into LMWSC nanoparticles was thought to be an ion complex formation between LMWSC and atRA. LMWSC nanoparticles showed high atRA loading efficiency over 90$\%$ (w/w). AtRA was continuously released from nanoparticles over 10 days. In in vitro cell cytotoxicity test, free atRA showed higher cytotoxic effect against CT 26 colon carcinoma cell line on 1 day. However, RAC nanoparticles showed similar cytotoxicity against CT 26 cells on 2 day. These results suggest the potential for the introduction of LMWSC nanoparticles into various biomedical fields such as drug delivery.

Butyrolactones Derivatives from the Fermentation Products of an Endophytic Fungus Aspergillus versicolor

  • Ye, Yan-Qing;Xia, Cong-Fang;Yang, Juan-Xia;Yang, Yu-Chun;Qin, Ying;Gao, Xue-Mei;Du, Gang;Li, Xue-Mei;Hu, Qiu-Fen
    • Bulletin of the Korean Chemical Society
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    • v.35 no.10
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    • pp.3059-3062
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    • 2014
  • Two new butyrolactones, asperphenol A (1) and B (2), together with four known butyrolactones (3-6) were isolated from the fermentation products of an endophytic fungus Aspergillus versicolor. Their structures were elucidated by spectroscopic methods including extensive 1D- and 2D-NMR techniques. Compounds 1-6 were also tested for their anti-tobacco mosaic virus (anti-TMV) activities. The results showed that compound 2 exhibited high anti-TMV activity with inhibition rate of 46.7%. The other compounds also exhibited potential anti-TMV activities with inhibition rates in the range of 21.8-28.4%.

Spectroscopic Characterization of Soil Humic Acid Fractions by Molecular Weight (토양에서 추출한 흄산의 분자량별 분류에 따른 분광학적 성질 비교)

  • Shin, Hyun Sang;Moon, Hichung;Yang, Han Beom;Yun, Sock Sung
    • Journal of the Korean Chemical Society
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    • v.39 no.1
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    • pp.66-70
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    • 1995
  • The soil humic acid was subdivided into four subfractions by molecular weight (F1: >100.000 dalton; F2: >100.000 dalton; F3: >10.000 dalton; F4: >2.000 dalton) using MP-dual hollow fiber ultrafiltration system. The characterization using IR, 1H and 13C NMR spectroscopy, showed similar spectroscopic features of HA, demonstrating that the bulk properties of HA subfractions are very similar to one another. IR spectral data showed a decrease in polysaccharide contents and increase in carboxylate functionality as molecular weight become smaller.functions. The structure of (NO) can be described by two interactions (N${\cdot}{\cdot}{\cdot}$N, N${\cdot}{\cdot}{\cdot}$O). One is the ONNO structure with an (N${\cdot}{\cdot}{\cdot}$N) interaction. In this structure, acyclic cis-ONNO with $C_{2v}$-symmetry, acyclic trans-ONNO with $C_{2h}$, and cyclic ONNO with trapezoidal structure ($C_{2v}$) are optimized at the MP2 level. The other structure is the ONON structure with an (N${\cdot}{\cdot}{\cdot}$O) interaction. In the structure, acyclic cis-ONON with Cs$^{-symmetry}$ and cyclic ONON of the rectangular ($C_{2h}$), square $(D_{2h})$, rhombic $(D_{2h})$, and parallelogramic $(D_{2h})$ geometries are also optimized. It is found that acyclic cis-ONNO $(^1A_1$) is the most stable structure and cyclic ONNO ($^3A_1$) is the least stable. Acyclic trans-ONNO ($^3A_1$) with an (N${\cdot}{\cdot}{\cdot}$N) interaction, acyclic trans-ONON and bicyclic ONON $(C_{2v})$ with (N${\cdot}{\cdot}{\cdot}$O) interaction, and acyclic cis- and trans-NOON with an (O${\cdot}{\cdot}{\cdot}$O) interaction can not be optimized at the MP2 level. Particularly, acyclic trans-ONNO with $C_{2h}$-symmetry can not be optimized at the CCSD(T) level. Meanwhile, acyclic NNOO ($^1A_1$, $C_s)$ and trianglic NNOO ($^1A_1$,$C_{2v})$ formed by the (O${\cdot}{\cdot}{\cdot}$N) interaction between $O_2$and $N_2$are optimized at the MP2 level. The binding energies and the relative energy gaps among the isomers are found to be relatively small./sec. Spiral CT scans during the arterial phase were obtained 35 seconds after the injection of contrast medium. CT findings of 78 lesions less than 4cm in diameter were correlated with angiographic findings. Results : The attenuation of lesions was high(n = 69), iso(n = 5), and low(n = 4) compared with liver parenchyma during the arterial phase of spiral CT. In lesions with high-, iso-, and low-attenuation during the arterial phase of spiral CT, hypervascularity on angiograms was found in 63 of 69(91.3%), three of five(60%), and three of four lesions(75%), respectively. Six lesions with high-attenuation on the arterial phase of spiral CT were not seen on angiography. Two iso-attenuated and one low-attenuated lesion were hypovascular on angiograms. Conclusion : The results of this study suggest that with some exceptions there was good correlation between the arterial phase of spiral CT and angiography.

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