• Title/Summary/Keyword: $^1H$-$^1H$ COSY

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Nucleoside Constituents of the Egyptian Tunicate Eudistoma laysani

  • Abou-Hussein, Dina R.;Badr, Jihan M.;Youssef, Diaa T.A.
    • Natural Product Sciences
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    • v.13 no.3
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    • pp.229-233
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    • 2007
  • Chemical investigation of the crude extract of the Egyptian marine tunicate Eudistoma laysani led to the isolation of a new nucleoside; 3-deazainosine and four known ones; inosine, 2'-deoxyuridine, adenosine and 2'-deoxyadenosine. Structural elucidation of the isolated compounds was based on intensive studies of their spectral data including 1D ($^{1}H$ and $^{13}C$) and 2D ($^{1}H-^{1}H$ COSY, HMQC, HMBC) NMR together with mass spectra. The antioxidant effects of the isolated compounds were determined using DPPH, where they exhibited significant activities.

Synthesis and the Absolute Configurations of Isoflavanone Enantiomers

  • Won, Dong-Ho;Shin, Bok-Kyu;Han, Jae-Hong
    • Journal of Applied Biological Chemistry
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    • v.51 no.1
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    • pp.17-19
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    • 2008
  • Isoflavanone has been synthesized from the reduction of isoflavone in nearly quantitative yield. Isoflavone with seven equivalents of ammonium formate in the presence of Pd/C in ethanol under $N_2$ atmosphere exclusively produced the two-electron reduced product in two hours. It was characterized by various spectroscopic methods, including UV-VIS, EI-MS, $^1H$-NMR, $^{13}C$-NMR and $^1H$, $^1H$-COSY. The racemic mixture was separated by Sumi-Chiral column chromatography and the absolute configurations of the enantiomers were characterized by circular dichroism spectroscopy.

Identification of Anti-Oxidant and Anti-Tyrosinase Activity of Phenolic Components Isolated from Betula schmidtii (박달나무로부터 분리된 페놀성 화합물의 항산화 및 Tyrosinase 저해 활성 연구)

  • Wang, Da-Hye;Chung, Ha Sook
    • The Korean Journal of Food And Nutrition
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    • v.34 no.5
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    • pp.553-559
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    • 2021
  • The aim of study to investigate the phytochemicals and biological activities the bark of Betula schmidtii. The studies consisted of the solvent extraction, followed by the isolation of phenolic components 1~3 from ethyl acetate-soluble fraction of Betula schmidtii Bark. Their chemical structures were identified as arbutin (1), ρ-coumaric acid (2) and ferulic acid (3) using Ultraviolet-Visible (UV-Vis) Spectrophotometer, Electrospray Ionization Mass Spectrometry (ESI-MS) (negative ion mode), 1H-Nuclear Magnetic Resonance (NMR), 13C-NMR, 1H-1H Correlation Spectroscopy (COSY) and 1H-13C Hetero Nuclear Multiple Quantum Correlation (HMQC) spectral data. Compounds 1~3 shows the anti-oxidant effect with IC50 values of 29.74±1.52, 21.32±1.07 and 34.41±1.24 in 1,1-diphenyl-2-picrylhydrazyl (DPPH) free radical scavenging activity, respectively. Also, compounds 1~3 exhibited mushroom tyrosinase inhibitory activity with IC50 values of 31.14±1.07, 42.54±1.46 and 69.22±1.43 µM, respectively.

A Study on the Extractives of Domestic Major Softwood Needles (II) - Antioxidant Activity of the Extractives from the Needles of Chamaecyparis pisifera (Sieb. et Zucc.) Endlicher - (국내산 주요 침엽수 잎의 추출성분 (II) - 화백나무 (Chamaecyparis pisifera (Sieb. et Zucc.) Endlicher)잎 추출성분 및 항산화 활성 -)

  • Lee, Sang-Keug;Bae, Young-Soo
    • Journal of the Korean Wood Science and Technology
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    • v.34 no.4
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    • pp.76-82
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    • 2006
  • The dried ground needles (2.0 kg) of Chamaecyparis pisifera (Sieb. et Zucc.) Endlicher were extracted with acetone-$H_2O$ (7:3, v/v), concentrated, and fractionated with a series of n-hexane, methylene chloride, ethyl acetate and water on a separation funnel. Each fraction was freeze dried, then a portion of ethyl acetate soluble powder was chromatographed on a Sephadex LH-20 column using a series of aqueous methanol and ethanol-n-hexane mixture as eluents. The isolated compounds were identified by cellulose TLC, $^1H$-, $^{13}C$-NMR, COSY, HETCOR, FAB and EI-MS. (+)-catechin, taxifolin-3-O-${\beta}$-D-xylopyrano-side, quercetin-3-O-${\alpha}$-L-rhamnopyranoside were isolated from the ethyl acetate soluble fraction of Chamaecypairs pisifera needle. Antioxidative tests on the isolated compounds indicated that all of the compounds showed similar values to ${\alpha}$-tocopherol and BHT as controls.

New Stigmastane Steroids Constituents from Rice Hulls of Oryza sativa and Inhibitory Activity on Radish seed

  • Jeong, Il-Min;Ali, Mohd;Khanh, Tran Dang;Choung, Myoung-Gun;Park, Hong-Jae;Ahmad, Ateeque
    • Bulletin of the Korean Chemical Society
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    • v.27 no.1
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    • pp.93-98
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    • 2006
  • Two new compounds 1'-(stigmast-11,20(21),25-trien 3$\alpha$,9$\alpha$-diolyl)-3'-(pimara-11,15-dien-3$\alpha$-olyl) glycerol (1) and stigmast-5-en-3$\alpha$,26-diol (2) along with known fatty acids n-hexacosanoic acid (3) and hexadecanoic acid (4), have been isolated from the methanol extract of rice hulls of Oryza sativa. The structures of the compounds were elucidated using 1D and 2D NMR spectral methods, viz; $^1H, ^{13}C, ^{13}C$-DEPT, $^1H-^1H$ COSY, $^1H-^{13}C$ HETCOR, HSQC and HMBC aided by IR, EIMS, FABMS and HRFABMS. Compound (1) showed inhibition to radish germination, growth of shoot and root length.

Chemical Investigation on an Endophytic fungus Gibberella moniliformis JS1055 Derived from a Halophyte Vitex rotundifolia

  • Kim, Jung Wha;Ryu, Jiyoung;Shim, Sang Hee
    • Natural Product Sciences
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    • v.24 no.3
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    • pp.189-193
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    • 2018
  • Chemical investigation of the ethyl acetate extract of Gibberella moniliformis JS1055 endophytic fungus derived from a halophyte, Vitex rotundifolia, led to the isolation of nine compounds including 7-butyl-6,8-dihydroxy-3(R)-pent-11-enylisochroman-1-one (1), 7-butyl-6,8-dihydroxy-3(R)-pentylisochroman-1-one (2), 7-butyl6,8-dihydroxy-3(R)-pentylisochroman-1-one (3), $5{\alpha},8{\alpha}$-epidioxyergosta-6,9(11),22-trien-3-ol (4), ergosterol peroxide (5), tetradecanoic acid (6), 8-O-methylfusarubin (7), nicotinic acid (8) and adenosine (9). They were identified by extensive spectroscopic data analysis including 1D, 2D ($^1H-^1H$ COSY, HSQC, HMBC) NMR, and ESIMS. All the isolates (1-9) are reported for the first time from this endophytic fungus.

Chemical Constituents from the Aerial Parts of Aster yomena

  • Jin, Qinglong;Ko, Hae Ju;Chang, Young-Su;Woo, Eun-Rhan
    • Natural Product Sciences
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    • v.19 no.3
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    • pp.269-274
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    • 2013
  • Nine terpenoids, spinasterone (1), simiarenol (2), phytol (3), lupeol (4), ${\alpha}$-amyrin (5), $1{\beta},4{\beta}$-dihydroxyeudesman-11-ene (6), 3,7-dihydroxyhumula-4,8(15),10(E)-triene (7), 2,6-dihydroxyhumula-3(12),7(13), 9E-triene (8), 23-hydroxybetulin (9) were isolated from the aerial parts of Aster yomena M. Their structures were identified based on 1D and 2D NMR, including $^1H-^1H$ COSY, HSQC, HMBC and NOESY spectroscopic analyses. Compounds 1 - 9 were isolated from this plant for the first time.

Three Norisoprenoids from the Brown Alga Sargassum thunbergii (갈조류 지충으로부터 분리한 3개의 Norisoprenoids 화합물)

  • Park, Ki-Eui;Kim, You-Ah;Jung, Hyun-Ah;Lee, Hee-Jung;Ahn, Jong-Woong;Lee, Burm-Jong;Seo, Young-Wan
    • Journal of the Korean Chemical Society
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    • v.48 no.4
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    • pp.394-398
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    • 2004
  • From Sargassum thunbergii which is widely distributed in coastal area of Korea, three norisoprenoids, (+)-epiloliolide (1), (-)-loliolide (2), and apo-9'-fucoxanthinone (3) were isolated by using column chromatography and reverse-phase HPLC. Compound 1, 2 and 3 were for the first time isolated from the Brown Alga Sargassum thunbergii. Particularly, Compound 1 was for the first time isolated the marine organism although it was reported from the terrestrial plant. Their structures have been determined by extensive 2-D NMR experiments such as $^1H COSY, NOESY, HMQC$, and HMBC and by comparison with the reported data in the literature.

Structure Elucidation of New Cochlioquinol Derivatives from Pathogenic Fungus Bipolaris cynodontis (식물 병원균 Bipolaris cynodontis로부터 분리한 새로운 Cochlioquinol 유도체의 구조 분석)

  • Lim, Chi-Hwan
    • Analytical Science and Technology
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    • v.9 no.1
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    • pp.112-117
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    • 1996
  • Three active compounds were isolated from the culture of a plant pathogenic fungus, Bipolaris cynodontis. The structure elucidation of these compounds was accomplished by 2D NMR techniques, such as $^1H-^1H$ and $^{13}C-^1H$ COSY, COLOC, HMBC and rotating frame NOE(ROESY). Compounds were found as derivatives of cochlioquinone and cochlioquinol that were previously isolated as phytotoxins from B. bicolor and B. cynodontis, respectively. The compounds showed phytotxicity against Italian ryegrass, one of the host plants of B. cynodontis.

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NMR Studies of Zinc-binding Luteinizing Hormone Releasing Hormone

  • Kim, Dae-Sung;Lee, Mi-Sun;Lee, Chang-Jun;Won, Ho-Shik
    • Journal of the Korean Magnetic Resonance Society
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    • v.10 no.2
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    • pp.163-174
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    • 2006
  • Luteinizing Hormone Releasing Hormone(LHRH) is a decapeptide neurotransmitter known to be regulated by metal ions in the hyperthalamus. Zn-binding LHRH complex was systhesized, and zinc-LHRH complex was studied to understand what kinds of structural modifications would be critical in the LHRH releasing mechanism. Both nonexchangeable and exchangeable $^1H-NMR$ signal assignments were accomplished by pH-dependent and COSY NMR experiments. In addition, $^1H-NMR$ chemical shift changes of a-proton and peptide NH NMR signals at different pH condition, and $^1H-NMR$ signal differences between metal free and metallo-LHRH complex was monitored. NMR signals exhibit that primary metal-binding sites are nitrogens donor of imidazole ring and Arg, and peptide oxygen of Pro-His in the sequence. Structure obtained in this study has a cyclic conformation which is similar to that of energy minimized, and exhibits a specific a-helical turn with residue numbers $(2{\sim}7)$ out of 10 amino acids.

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