• Title/Summary/Keyword: $^{13}C-NMR$ data

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Pyrophen Produced by Endophytic Fungi Aspergillus sp Isolated from Piper crocatum Ruiz & Pav Exhibits Cytotoxic Activity and Induces S Phase Arrest in T47D Breast Cancer Cells

  • Astuti, Puji;Erden, Willy;Wahyono, Wahyono;Wahyuono, Subagus;Hertiani, Triana
    • Asian Pacific Journal of Cancer Prevention
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    • v.17 no.2
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    • pp.615-618
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    • 2016
  • Ethyl acetate extracts obtained from culture of endophytic fungi Aspergillus sp isolated from Piper crocatum Ruiz & Pav, have been shown to possess cytotoxic activity against T47D breast cancer cells. Investigations were here conducted to determine bioactive compounds responsible for the activity. Bioassay guided fractionation was employed to obtain active compounds. Structure elucidation was performed based on analysis of LC-MS, $^1H$-NMR, $^{13}C$-NMR, COSY, DEPT, HMQC, HMBC data. Cytotoxity assays were conducted in 96 well plates against T47D and Vero cell lines. Bioassay guided isolation and chemical investigation led to the isolation of pyrophen, a 4-methoxy-6-(1'-acetamido-2'-phenylethyl)-2H-pyran-2-one. Further analysis of its activity against T47D and Vero cells showed an ability to inhibit the growth of T47D cells with IC50 values of $9.2{\mu}g/mL$ but less cytotoxicity to Vero cells with an $IC_{50}$ of $109{\mu}g/mL$. This compound at a concentration of 400 ng/mL induced S-phase arrest in T47D cells.

Isolation of Flavonoids from Carthami Flos and their Antioxidative Activity (홍화의 플라보노이드 성분 분리 및 항산화 활성)

  • Chung, Sung-Hee;Moon, Ye-Ji;Kim, Sung-Gun;Kim, Kyoung-Young;Lee, Kyoung-Tae;Kim, Ho-Kyoung;Whang, Wan-Kyunn
    • YAKHAK HOEJI
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    • v.52 no.4
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    • pp.241-251
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    • 2008
  • In this study, isolation of antioxidative compounds was performed for development of anti-oxidizing agent. $CHCl_{3}$, $H_{2}O$, 30%, 60% MeOH, MeOH fractions were examined antioxidative activity by DPPH method, TBARS assay, and SOD like activity. It was revealed that 30%, 60% MeOH fractions had significant antioxidative activity. From 30%, 60% MeOH fraction, nine compounds were isolated and elucidated kaempferol $3-O-{\alpha}-L-rhamnopyranosyl$ $(1{\rightarrow}6)-{\beta}-D-glucopyranoside$ (1), quercetin $7-O-{\beta}-D-glucopyranoside$ (II), quercetin $3-O-{\alpha}-L-rhamnopyranosyl$ $(1{\rightarrow}6)$ ${\beta}-D-glucopyranoside(rutin)$ (III), 6-hydroxykaempferol $3-O-{\beta}-D-glucopyranoside$ (lV), kaempferol $3-O-{\beta}-D-glucopyranosyl$ $(1{\rightarrow}2)$ ${\beta}-D-glucopyranoside$ (V), kaempferol $3-O-{\beta}-D-glucopyranoside$ (VI), luteolin (VII), quercetin $3-O-{\beta}-D-glucopyranoside$ (VIII), apigenin $7-O-{\beta}-D-glucuronopyranoside$ (IX) through physicochemical data and spectroscopic methods (Negative FAB-MS, $^1H-NMR$, $^{13}C-NMR$). Entirely, all compounds had similar antioxidative activity, but more OH group had more antioxidative activity.

Biolosical Activities of Isolated Compounds from Peucedani Radix (식방풍의 성분분리 및 생리활성)

  • Kim, Do-Hoon;Han, Chi-Su;Kim, Gi-Eun;Kim, Jin-Hyo;Kim, Sung-Gun;Kim, Ho-Kyoung;Oh, O-Jin;Whang, Wan-Kyunn
    • YAKHAK HOEJI
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    • v.53 no.3
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    • pp.130-137
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    • 2009
  • In this study, isolation of antioxidative compounds was performed for development of anti-oxidizing agent. $CHCl_3$, $H_2O$, 30%, 60% MeOH, MeOH fractions were examined antioxidative activity by DPPH, test of inhibition on NO production. It was revealed that 30%, 60% MeOH and $CHCl_3$ fractions had significant antioxidative activity. In 30% MeOH and 60% MeOH, $CHCl_3$ fraction, six compounds were isolated and elucidated as adenosine(I), guanosine(II), peucedanol 7-O-$\beta$-D-apiofuranosyl(1$\rightarrow$6)-$\beta$-glucopyranoside(III), peucedanol 7-O-$\beta$-D-glucopyranoside(IV), peucedanol(V) and scopoletin(VI) by physicochemical data and spectroscopic methods. (Negative FAB-MS, $^{1}H-NMR$, $^{13}C-NMR$). The results from antioxidative activity screening for the each compound showed that compound IV was relatively superior antioxidant ability. In anti-inflammatory activation assay, compound III, IV, VI had concentration-dependent-activity and compound IV had superior anti-inflammatory ability. These results suggest that Peucedani Radix might be developed as a potent anti-oxidative, anti-inflammatory agents and ingredients for related functional foods.

Antishigellosis and Cytotoxic Potency of Crude Extracts and Isolated Constituents from Duranta repens

  • Nikkon, Farjana;Habib, M. Rowshanul;Karim, M. Rezaul;Hossain, M. Shamim;Mosaddik, M. Ashik;Haque, M. Ekramul
    • Mycobiology
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    • v.36 no.3
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    • pp.173-177
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    • 2008
  • The crude ethanol extracts (stem and fruits), their fractions and two triterpenes, $\beta$-Amyrin and 12-Oleanene 3$\beta$, 21$\beta$-diol, isolated as a mixture from the chloroform soluble fraction of an ethanolic extract of Duranta repens stem, were evaluated for antibacterial, antifungal activities by the disc diffusion method and cytotoxicity by brine shrimp lethality bioassay. The structures of the two compounds were confirmed by IR, $^1H$-NMR, $^{13}C$-NMR and LC-MS spectral data. The chloroform soluble fraction of stem and ethanol extract of fruits possess potent antishigellosis activity and also exhibited moderate activity against some pathogenic bacteria and fungi but the isolated compound 1 (mixture of $\beta$-Amyrin and 12-Oleanene 3$\beta$, 21$\beta$-diol) showed mild to moderate inhibitory activity to microbial growth. The minimum inhibitory concentrations (MICs) of the extracts (stem and fruits), their fractions and compound 1 were found to be in the range of 32$\sim$128 ${\mu}g/ml$. The chloroform soluble fractions of stem and ethanol extract of fruit showed significant cytotoxicity with $LC_{50}$ value of 0.94 ${\mu}g/ml$ and 0.49 ${\mu}g/ml$, respectively against brine shrimp larvae.

Transition Metal Complexes Derived From 2-hydroxy-4-(p-tolyldiazenyl)benzylidene)-2-(p-tolylamino)acetohydrazide Synthesis, Structural Characterization, and Biological Activities

  • Alhakimi, Ahmed N.;Shakdofa, Mohamad M.E.;Saeed, S. El-Sayed;Shakdofa, Adel M.E.;Al-Fakeh, Maged S.;Abdu, Ashwaq M.;Alhagri, Ibrahim A.
    • Journal of the Korean Chemical Society
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    • v.65 no.2
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    • pp.93-105
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    • 2021
  • Mononuclear Cu(II), Ni(II), Co(II), Mn(II), Zn(II), Fe(III), Ru(III), and UO2(II) complexes of 2-hydroxy-4-(p-tolyldiazenyl)benzylidene)-2-(p-tolylamino)acetohydrazide (H2L) were prepared by direct method. The ligand and its complexes were isolated in solid state and characterized by analytical techniques such as elemental and thermal analyses, molar conductance, magnetic susceptibility measurements and spectroscopic techniques such as UV-Visible, IR, 1H-NMR and 13C-NMR. The spectral data indicated that the ligand acted as neutral/monobasic bidentate or monobasic/dibasic tridentate ligand bonded to the metal ions through the oxygen atom of ketonic or enolic carbonyl group, azomethine nitrogen atom and deprotonated/protonated phenolic oxygen atom forming either tetragonally distorted octahedral or octahedral. Antimicrobial activities of the ligand and its complexes were evaluated against Escherichia coli, Bacillus subtilis and Aspergillus niger by well diffusion method. The results of antifungal activity showed that the Fe(III) complex (10) exhibited higher antifungal against Aspergillus niger than the other complexes. However, the results of antibacterial activity revealed that Cu(II) complex (4) is the most active against Escherichia coli while the Cu(II) complex (5) and Fe(III) complex (10) exhibited higher antibacterial effect on Bacillus subtilis than the other complexes.

A New Stilbene Dimer and Other Chemical Constituents from Monanthotaxis littoralis with Their Antimicrobial Activities

  • Dongmo, Arnaud Joseph Nguetse;Ekom, Steve Endeguele;Tamokou, Jean-de-Dieu;Tagousop, Cyrille Ngoufack;Harakat, Dominique;Voutquenne-Nazabadioko, Laurence;Ngnokam, David
    • Natural Product Sciences
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    • v.26 no.4
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    • pp.317-325
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    • 2020
  • A new dimer stilbene [Monalittorin (1)] and ten known compounds [engeletin (2), aurantiamide acetate (3), lupeol (4), friedelin (5), quercetin (6), tiliroside (7), rutoside (8), astragalin (9), isoquercitrin (10) and quercimeritroside (11)] have been isolated from the leaves of Monanthotaxis littoralis (Annonaceae). The structures of these compounds were established by interpretation of their data, mainly, HR-TOFESIMS, 1-D NMR (1H and 13C) and 2-D NMR (1H-1H COSY, HSQC, HMBC and NOESY) and by comparison with the literature. The evaluation of their antimicrobial activities against three bacteria (Staphylococcus aureus ATCC 25923, Escherichia coli S2 (1) and Pseudomonas aeruginosa PA01) and three fungal strains (Candida albicans ATCC10231, Candida tropicalis PK233 and Cryptococcus neoformans H99) using broth micro dilution method, showed the largest antimicrobial activities of EtOAc fraction and compounds 1, 5, 6, 8 and 11 (MIC = 8 - 64 ㎍/mL). In addition, EtOAc fraction presented synergistic effect with Vancomycin and fluconazole against the tested microorganisms.

Isolation and Evaluation of Anti-oxidative Constituents from the Extracts of Ficus erecta var. sieboldii King Leaves (좁은잎천선과 잎 추출물 유래 항산화 활성 성분의 동정 및 효능 확인)

  • Park, Sung Hwan;Kim, Jung Eun;Yeum, Hyun Sook;Lee, Nam Ho
    • Journal of the Society of Cosmetic Scientists of Korea
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    • v.42 no.4
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    • pp.321-328
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    • 2016
  • In this study, we investigated identification of anti-oxidative constituents from Ficus erecta var. sieboldii King (F. erecta) leaves. DPPH and $ABTS^+$ radical scavenging activities were screened for the ethanol extract and solvent fractions, and ethyl acetate fraction showed the most potent scavenging activities. Five constituents were isolated from the ethyl acetate fraction of F. erecta leaves; monoolein (1), oleic acid (2), lutein (3), afzelechin (4), catechin (5). The chemical structures of the isolated compounds were elucidated based on the spectroscopic data including NMR spectra, as well as comparison of the data to the literature values. As far as we know, all of the compounds 1 ~ 5 were isolated for the first time from this plant. Studies on DPPH and $ABTS^+$ radical scavenging activities were conducted for the isolated compounds. Among them, afzelechin (4) and catechin (5) showed strong DPPH and $ABTS^+$ radical scavenging activities, whose activities were comparable to a positive control vitamin C. Also, the content of catechin isolated from this plant was determined by HPLC and it was about 3.8 mg/g for the 70% ethanol extract and 20.8 mg/g for the ethyl acetate fraction. From these results, F. erecta leaves extract could be potentially applicable as anti-oxidant ingredients in cosmetic industries.

Isolation and Purification of Antibacterial Components in Cortex Phellodendri (황백나무로부터 항균성분의 분리 및 정제)

  • Kim, Jung-Bae;Shin, Woon-Seob;Kwon, Young-In;Bang, Byung-Ho
    • The Korean Journal of Food And Nutrition
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    • v.26 no.3
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    • pp.547-552
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    • 2013
  • Cortex Phellodendri (CP) is derived from the dried bark of Phellodendron amurense. It has been widely used as a drug in traditional Korea medicine for treating diarrhea, jaundice, swelling pains in the knees and feet, urinary tract infections and infections of the body surface. In this study, preparative centrifugal partition chromatography (CPC) was successfully carried out to separate antibacterial compounds from a CP methanol extract. The optimum two-phase CPC solvent system was composed of n-butanol: acetic acid: water (4:1:5 v/v/v). The flow rate of the mobile phase was 3 $m{\ell}/min$ in ascending mode with rotation at 1,000 rpm. The CPC-separated fraction and purification procedures were carried out by preparatory HPLC. Palmatine weas identified by $^1H$, $^{13}C$-nuclear magnetic resonance and electrospray ionization-mass spectroscopy spectral data analysis.

Vitamin B12 Model Complexes: Synthesis and Characterization of Thiocyanato Cobaloximes and Thiocyanato Bridged Dicobaloximes of O-donor Ligands: DNA Binding and Antimicrobial Activity (비타민 B12 모델 착물: O-주개 리간드인 Thiocyanato Cobaloximes 및 Thiocyanato로 연결된 Dicobaloximes의 합성 및 특성규명: DNA 결합 및 향균 활성)

  • Mustafa, Bakheit;Satyanarayana, S.
    • Journal of the Korean Chemical Society
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    • v.54 no.6
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    • pp.687-695
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    • 2010
  • Complexes of thiocyanato(L)cobaloximes where L is urea, acetamide, semicrabazide and formamide were synthesized and characterized. The reaction of thiocyanato (L) cobaloximes (SCNCo$(DH)_2$(L)) with benzyl (aquo) cobaloxime $PhCH_2Co(DH)_2(OH_2)$ was found to produce a series of thiocyanato bridged dicobaloximes of a general formula of $PhCH_2Co(DH)_2SCNCo(DH_2)(L)$. Evidence for formulation as dicobaloximes containing thiocyanato ligand bridges was obtained from infrared data which show $20-45cm^{-1}$ increase in vCN upon formation of the dicobaloxime from the corresponding terminal thiocyanocobaloxime (SCNCo$(DH)_2$(L)). Further characterization of these two series was done on the basis of ($^1H$,$^{13}C$)NMR, LCMS and elemental analysis. Anti-microbial activity of thiocyanato(L)cobaloximes and thiocyanato bridged dicobaloximes were screened against E. Coli. The DNA-binding behaviors of both monomers and dimers were investigated by spectroscopic methods and viscosity measurements. The results indicated that the dimer complexes bind with calf-thymus DNA in an intercalative mode via the terminal benzyl ring into the base pairs of DNA. It was observed that the monomer complexes did not interact with DNA. Fluorescence spectra for the interaction between thiocyanato bridged dicobaloximes and DNA were also studied.

Extractives from the Bark of Platycarya strobilacea (굴피나무(Platycarya strobilancea) 수피의 Flavonol glycosides)

  • Lee, Hak-Ju;Lee, Sang-Keug;Choi, Yun-Jeong;Jo, Hyun-Jin;Kang, Ha-Young;Choi, Don-Ha
    • Journal of Korean Society of Forest Science
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    • v.96 no.4
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    • pp.408-413
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    • 2007
  • The dried bark of Platycarya strobilacea were ground, extracted with 95% EtOH, concentrated, and one of EtOH extracts was fractionated with a series of n-hexane, dichloromethane and another was fractionated with a series of petroleumether, $Et_2O$, ethyl acetate on a separatory funnel. A portion of dichloromethane soluble was chromatographed on a Sephadex LH-20 column ($72.0{\times}5.0cm$) using EtOH-$CHCl_3$ (7:3, v/v) as eluent and A portion of $Et_2O$ soluble was chromatographed on a silica gel column ($42.0{\times}3.5cm$) using $CHCl_3$-MeOH (9:3, v/v) as eluent. The isolated compounds were identified by TLC, $^1H$-, $^{13}C$-NMR, HMBC and EI-MS. Two flavonoids and three flavonoid glycosides were isolated from the bark of P strobilacea. The structures were determined to quercetin (compound 1), myricetin (compound 2) as flavonol compounds and afzelin (compound 3), quercitrin (compound 4), myricitrin (compound 5) as flavonol glycosides, respectively, on the basis of spectrosopic data.