• Title/Summary/Keyword: 2-D NMR

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Soluble Epoxide Hydrolase Inhibitory Activity from Euphorbia supina Rafin

  • Luyen, Bui Thi Thuy;Thao, Nguyen Phuong;Tai, Bui Huu;Dat, Le Duc;Kim, Ji Eun;Yang, Seo Young;Kwon, Se Uk;Lee, Young Mi;Kim, Young Ho
    • Natural Product Sciences
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    • v.21 no.3
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    • pp.176-184
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    • 2015
  • In our search for natural soluble epoxide hydrolase (sEH) inhibitors from plants, an extract of the dried whole plants of Euphorbia supina Rafin was found to significantly inhibit sEH activity in vitro. Phytochemical investigation of E. supina resulted in isolation of 17 compounds (1 - 17), including triterpenes (1 - 4), phenolic compounds (5 - 8), and flavonoid derivatives (9 - 17). The structures of the isolated compounds were established mainly by extensive analysis of the 1D and 2D NMR, and MS data. All of the isolated compounds were evaluated for their sEH inhibitory activity. Among the isolated phenolic compounds, 8 was identified as a significant inhibitor of sEH, with an IC50 value of 15.4 ± 1.3 μM. Additionally, a kinetic analysis of isolated compounds (2, 5, 8 - 11, 13, and 17) indicated that the inhibitory effects of flavonoid derivatives 10 and 11 were of mixed-type, with inhibitory constants (Ki) ranging from 3.6 ± 0.8 to 21.8 ± 1.0 μM, whereas compounds 2, 5, 8, 9, 13, and 17 were non-competitive inhibitors with inhibition Ki values ranging from 3.3 ± 0.2 to 39.5 ± 0.0 μM.

Two New Diphenylethylenes from Arundina graminifolia and Their Cytotoxicity

  • Li, Yin-Ke;Zhou, Bin;Ye, Yan-Qing;Du, Gang;Niu, De-Yun;Meng, Chun-Yang;Gao, Xue-Mei;Hu, Qiu-Fen
    • Bulletin of the Korean Chemical Society
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    • v.34 no.11
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    • pp.3257-3260
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    • 2013
  • Two new diphenylethylenes, gramniphenols H and I (1 and 2), together with six known diphenylethylenes (3-8), were isolated from Arundina graminifolia. The structures of 1-8 were elucidated by spectroscopic methods including extensive 1D- and 2D-NMR techniques. Compounds 1 and 2 were evaluated for their cytotoxicity against five human tumor cell lines. Compound 1 showed cytotoxicity against PC3 cells with $IC_{50}$ value of 3.5 ${\mu}M$. Compound 2 showed cytotoxicity against NB4 and PC3 cells with $IC_{50}$ values of 3.6 and 3.8 ${\mu}M$, respectively.

Synthesis of Curcumin Glycosides with Enhanced Anticancer Properties Using One-Pot Multienzyme Glycosylation Technique

  • Gurung, Rit Bahadur;Gong, So Youn;Dhakal, Dipesh;Le, Tuoi Thi;Jung, Na Rae;Jung, Hye Jin;Oh, Tae Jin;Sohng, Jae Kyung
    • Journal of Microbiology and Biotechnology
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    • v.27 no.9
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    • pp.1639-1648
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    • 2017
  • Curcumin is a natural polyphenolic compound, widely acclaimed for its antioxidant, anti-inflammatory, antibacterial, and anticancerous properties. However, its use has been limited due to its low-aqueous solubility and poor bioavailability, rapid clearance, and low cellular uptake. In order to assess the effect of glycosylation on the pharmacological properties of curcumin, one-pot multienzyme (OPME) chemoenzymatic glycosylation reactions with UDP-${\alpha}-{\text\tiny{D}}$-glucose or UDP-${\alpha}-{\text\tiny{D}}$-2-deoxyglucose as donor substrate were employed. The result indicated significant conversion of curcumin to its glycosylated derivatives: curcumin 4'-O-${\beta}$-glucoside, curcumin 4',4"-di-O-${\beta}$-glucoside, curcumin 4'-O-${\beta}$-2-deoxyglucoside, and curcumin 4',4"-di-O-${\beta}$-2-deoxyglucoside. The products were characterized by ultra-fast performance liquid chromatography, high-resolution quadruple-time-of-flight electrospray ionization-mass spectrometry, and NMR analyses. All the products showed improved water solubility and comparable antibacterial activities. Additionally, the curcumin 4'-O-${\beta}$-glucoside and curcumin 4'-O-${\beta}$-2-deoxyglucoside showed enhanced anticancer activities compared with the parent aglycone and diglycoside derivatives. This result indicates that glycosylation can be an effective approach for enhancing the pharmaceutical properties of different natural products, such as curcumin.

Development of Biologically Active Compounds from Edible Plant Sources-XVII. Chemical Constituents from the Aerial Parts of Artemisia princeps PAMPANINI (Sajuarissuk) (식용식물자원으로부터 활성물질의 탐색-XVII. 싸주아리쑥(Artemisia princeps PAMPANINI, Sajuarissuk) 지상부의 화학성분)

  • Yoo, Jong-Su;Bang, Myun-Ho;Ahn, Eun-Mi;Song, Myoung-Chong;Chung, Hae-Gon;Jeong, Tae-Sook;Lee, Kyung-Tae;Choi, Myung-Sook;Baek, Nam-In
    • Applied Biological Chemistry
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    • v.50 no.1
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    • pp.53-56
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    • 2007
  • The aerial parts of Artemisia princeps PAMPANINI were extracted with 80% aqueous MeOH and the concentrated extract was partitioned with EtOAc, n-BuOH and $H_2$O, successively. From the EtOAc fraction, five compounds were isolated through the repeated silica gel and ODS column chromatog-raphies. They were determined as friedelin (1), ${\beta}$-amyrin (2), ${\beta}$-amyrin acetate (3), camphanediol (4) and hispidulin (5) on the basis of spectral data, respectively.

Effect of 1,2,3,4,6-penta-O-galloyl-$\beta$-D-glucose isolated from Galla Rhois on gap junctional intercellular communication and antiangiogenic activity (오배자 BuOH층에서 분리한 1,2,3,4,6-penta-O-galloyl-$\beta$-D-glucose의 세포간교통 회복 및 혁관형성 억제작용에 대한 효과)

  • Huh Jeong Eun;Lee Hyo Jung;Song Gyu Yong;Cha Bae Cheon;Kim Han Sung;Yoo Dong Youl;Ryu Shi Yong;Kim Sung Hoon
    • Journal of Physiology & Pathology in Korean Medicine
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    • v.16 no.3
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    • pp.452-457
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    • 2002
  • Galla Rhois is a gallnut of Rhus javanica Linne used for treatment of diarrhea, hemorrhage, cough, leukorrhea and toxic tumor etc in oriental medicine. For the evaluation of antitumor effect of Galla Rhois, activity based fractionation was done. We isolated an effective compound and identified 1,2,3,4,6-penta-O-galloyl-β-D-glucose(PGG) by photometric analysis such as NMR and MASS. Then, we studied the angiogenic activity of PGG. It showed a cytotoxicity against SK-OV-3, SK-OV-3, HT1080 with IC/sub 50/ of 50 ug/ml approximately. It also effectively inhibited proliferation of HUVEC cells treated by bFGF to 30% of control at 20 ug/ml and cell migration to 80% at 10 ug in a dose dependent fashion. Tube formation of HUVEC cells on matrigel was effectively suppressed from 2.5 ug/ml of concentration by PGG. Moreover, it effectively recovered the dysfunction of gap junctional intercellular communication in WB-F344 rat liver epithelial cells caused by hydrogen peroxide at 4 ug/ml suggesting it potently can inhibit tumor promotion. Taken together, it indicates 1,2,3,4,6-penta-O-galloyl- β -D-glucose has antiangiogenic activity.

Synthesis and Spectroscopic Characterization of Manganese(II), Iron(III) and Cobalt(III) Complexes of Macrocyclic Ligand. Potential of Cobalt(III) Complex in Biological Activity

  • El-Tabl, Abdou S.;Shakdofa, Mohamad M.E.;El-Seidy, Ahmed M.A.
    • Journal of the Korean Chemical Society
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    • v.55 no.6
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    • pp.919-925
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    • 2011
  • A new series of manganese(II), iron(III) and cobalt(III) complexes of 14-membered macrocyclic ligand, (3,6,10,13,16,19-hexaazabicyclo[6.6.6]icosane-1,8-diamine) have been prepared and characterized by elemental analyses, IR, UV-VIS, $^1H$- and $^{13}C$- NMR spectra, magnetic susceptibilities, conductivities, and ESR measurements. Molar conductance measurements in DMF solution indicate that the complexes are electrolytes. The ESR spectrum for cobalt(III) complex in $CD_3OD+10%D_2O$ after exposure to $^{60}Co-{\gamma}$-rays at 77 K using a 0.2217 M rad $h^{-1}$ vicrad source showed $g_{\perp}$ > $g_{\parallel}$ > $g_e$, indicating that, the unpaired electron site is mainly present in the $d_z2$ orbital with covalent bond character. In this case, the ligand hyperfine tensors are nearly collinear with ${\gamma}$-tensors, so there is no major tendency to bend. Therefore, little extra delocalization via the ring lobe of the $dz^2$ orbital occurs. However, the ESR spectrum in solid state after exposure to $^{60}Co-{\gamma}$-rays at 77 K showed $g_{\parallel}$ > $g_{\perp}$ > $g_e$, indicating that, the unpaired electron site is mainly present in the $d_x2_{-y}2$ ground state as the resulting spectrum contains a large number of randomly oriented molecules provided that, the principle directions of g and A tensors. Manganese (II) complex 2, $[H_{12}LMn]Cl_4.2H_2O$, showed six isotropic lines characteristic to an unpaired electron interacting with a nucleus of spin 5/2, however, iron(III) complex 3, $[H_{12}LFe]Cl_5.H_2O$, showed spectrum of a high spin $^{57}Fe$ (I=1/2), $d^5$ configuration. The geometry of these complexes was supported by elemental analyses, IR, electronic and ESR spectral studies. Complex 1 showed exploitation in reducing the amount of electron adducts formed in DNA during irradiation with low radiation products.

Antioxidant and α-Glucosidase Inhibitory Activities of the Extract from Sparganium stoloniferum Buch.-Ham. Root and Its Constituent Compounds

  • Xu, Ming Lu;Wang, Lan;Hu, Jian He;Wang, Myeong-Hyeon
    • Preventive Nutrition and Food Science
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    • v.14 no.4
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    • pp.354-357
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    • 2009
  • Three compounds, vanillic acid, p-hydroxylcinnamic acid, p-hydroxybenzaldehyde have been isolated from the ethylacetate extract of Sparganium stoloniferum Buch.-Ham roots using silica gel open column chromatography, preparative thin-layer chromatography (pTLC) and reverse phase high performance liquid chromatography. The structures of the compounds were established on the basis of IR, extensive 1D NMR, and MS analyses. The ethylacetate (EtOAc) extract, vanillic acid, and p-hydroxybenzaldehyde showed $\alpha$-glucosidase inhibition activity of 72.71%, 20.13%, and 30.42%, at the concentration of 10 ${\mu}g/mL$, respectively. The EtOAc extract exhibited strong antioxidant activity with an $IC_50$ value of 24.37 ${\mu}g/mL$ against DPPH radical scavenging activity, the vanillic acid, p-hydroxylcinnamic acid, and p-hydroxybenzaldehyde with an $IC_50$ value of 2.10 ${\mu}M$, 1.59 ${\mu}M$, and 2.72 ${\mu}M$ against DPPH, respectively.

Synthesis, Urease and Acetylcholine Esterase Inhibition Activities of Some 1,4-Disubstituted Thiosemicarbazides and their 2,5-Disubstituted Thiadiazoles

  • Saleem, Muhammad;Rafiq, Muhammad;Hanif, Muhammad;Rama, Nasim Hasan;Seo, Sung-Yum;Lee, Ki-Hwan
    • Bulletin of the Korean Chemical Society
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    • v.33 no.8
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    • pp.2741-2747
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    • 2012
  • A new series of 2,5-disubstituted-1,3,4-thiadiazoles 6a-i was synthesized by overnight stirring various 1,4-disubstituted thiosemicarbazides 5a-i in polyphosphoric acid followed by neutralization. The structures of newly synthesized compounds 5a-i and 6a-i were characterized by IR, $^1H$ and $^{13}C$ NMR, elemental analysis and mass spectrometric studies. All the synthesized compounds were evaluated for their urease and acetylcholine esterase inhibition activities. Thiosemicarbazides 5a-i are found to possess excellent potential for urease inhibition, more than the standard drug. Thiosemicarbazides 5a-i are more potent urease inhibitor than their cyclic analogues thiadiazoles 6a-i. Almost all of the compounds are excellent inhibitors of acetylcholine esterase. The inhibition of acetylcholine esterase of compounds 5a, 5c, 5d, 5g, 5i, 6e, 6f, 6g, and 6i is much more than that of standard drug.

Synthesis of ${\alpha}-Sulfonated$ Fatty Acid Polyethylene Glycol Ester (알파술폰 고급지방산 폴리에틸렌 글리콜 에스테르류의 합성)

  • Kim, J.H.;Yeon, Y.H.;Jeong, N.H.;Nam, K.D.
    • Journal of the Korean Applied Science and Technology
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    • v.15 no.2
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    • pp.83-92
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    • 1998
  • ${\alpha}-sulfonated$ fatty acid polyethylene glycol esters with polyethylene oxide(addition, 3, 5, 10mol) were synthesized through esterification of ${\alpha}-sulfonated$ fatty acid methyl esters with alkyl chain length $C_{12}{\sim}C_{18}$. Their compounds were separated with column chromatography, and confirmed by TLC. Quantitative analysis of all the sulfonates were performed according to JIS K-3362 method, and ethylene oxide unit number were determined by ISO 2270 method. Structural properties of ${\alpha}-sulfonated$ fatty acid methyl esters and their derivatives were also identified from IR, and $^1H$ NMR spectra.

Inhibition of the expression on MMP-2, 9 and morphological changes via human fibrosarcoma cell line by 6,6'-bieckol from marine alga Ecklonia cava

  • Zhang, Chen;Li, Yong;Shi, Xiujuan;Kim, Se-Kwon
    • BMB Reports
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    • v.43 no.1
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    • pp.62-68
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    • 2010
  • Matrix Metalloproteinases (MMPs) are a family of zinc-endopeptidases which can degrade extracellular matrix (ECM) components and play important roles in a variety of biological and pathological processes. 6,6'-bieckol isolated and characterized from an edible marine brown alga Ecklonia cava (EC), according to the comprehensive spectral analysis of MS and NMR data. Here the influence of 6,6'-bieckol on expressions of MMPs was examined by zymography and western blot analysis via human fibrosarcoma cell line (HT1080). It is shown that 6,6'-bieckol significantly down regulated the expressions of MMP-2 and -9 in dose-dependent manner. The influence of 6,6'-bieckol on the cell viability and cell behavior of HT1080 cells were also investigated, our dates shown that it suppressed the migration and 3D culture in HT1080 cells. Meanwhile, we explored several signal pathways which may contribute to this process, and found the suppressing of MMPs expressions in HT1080 cells might be due to the suppression of NF-${\kappa}B$ signal pathway.