• Title/Summary/Keyword: HMBC-experiment

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The NMR assignments of anthraquinones from Cassia tora

  • Choi, Jae-Sue;Jung, Jee-Hyung;Lee, Hee-Jung;Kang, Sam-Sik
    • Archives of Pharmacal Research
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    • v.19 no.4
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    • pp.302-306
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    • 1996
  • The $^1H- and^{13}C-NMR$ spectra of alaternin, aurantio-obtusin, chryso-obtusin, obtusin and 2-glucosyl obtusifolin isolated from the seeds of Cassia tora have been assigned based on HMBC, long-range HETCOR, fully $^1H-coupled {13}^C-NMR$, deuterium isotope experiment, and by comparison with the model compounds.

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A Study on the Constituents from the Roots of Polygala tenuifolia (원지뿌리의 성분연구)

  • Park, Jin-Sea;Kim, Ki-Young;Doh, Sang-Hak;Kim, Jin-Sook
    • Korean Journal of Pharmacognosy
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    • v.30 no.4
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    • pp.417-419
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    • 1999
  • $Three\;compounds-ethyl-{\beta}-D-glucopyranoside$, 1,2,3,7-tetramethoxyxanthone, 1,7-dimethoxyxanthone-were isolated from roots of Polygala tenuifolia. The structures of these compounds were establised on the basis of spectral evidence including 2D NMR and HMBC studies. $Ethyl-{\beta}-D-glucopyranoside$ was isolated for the first time from Polygala genus and HMBC data of these compounds were first reported.

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NMR assignments including HMBC and 1D-TOCSY data of Astragaloside I, II and Isoastragaloside I from the Roots of Astragalus membranaceus (황기뿌리에서 분리한 Astragaloside I, II 및 Isoastragaloside I의 HMBC와 1D-TOCSY data를 포함한 nmr assignments)

  • Park, Jin-Seo;Kim, Chung-Sook;Kim, Jong-Moon;Kim, Jin-Sook
    • Korean Journal of Pharmacognosy
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    • v.31 no.1
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    • pp.34-38
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    • 2000
  • Three compounds were isolated from the roots of Astragalus membranaceus (Leguminosae). On the basis of spectroscopic evidences, the structures were characterized as $3-0-{\beta}-D-xylopyranosyl-(2',3'-O-diacetyl)-6-0-{\beta}-D-glucopyranosyl-3{\beta},6{\alpha},16{\beta},25-tetrahydroxy-20(R)$,24(S)-epoxy-cycloartane(Astragaloside I), $3-0-{\beta}-D-xylopyranosyl-(2'-O-acetyl)-6-0-{\beta}-D-glucopyranosyl-3{\beta},6{\alpha},16{\beta},25-tetrahydroxy-20(R)$,24(S)-epoxy-cycloartane(Astragaloside II), $3-0-{\beta}-D-xylopyranosyl-(2',4'-O-diacetyl)-6-0-{\beta}-D-glucopyranosyl-3{\beta},6{\alpha},16{\beta},25-tetrahydroxy-20(R)$,24(S)-epoxycycloartane(Isoastragaloside I). Full data of NMR including HMBC and 1D-TOCSY experiment of these compounds were reported for the first time.

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Isolation and Structure Identification of Antibacterial Substances from the Rhizome of Zingiber mioga Roscoe (양하의 근경에서 항균성 물질 분리 및 구조동정)

  • Kim, Seong-Cheol;Song, Eun-Young;Kim, Kong-Ho;Kwon, Hyeog-Mo;Kang, Sang-Heon;Park, Ki-Hun;Jung, Yong-Hwan;Jang, Ki-Chang
    • Applied Biological Chemistry
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    • v.46 no.3
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    • pp.246-250
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    • 2003
  • In order to isolate antibacterial substances from the rhizome of Zingiber mioga Roscoe, the ethanol extracts was fractionated according to the activity against Bacillus subtilis, B. cereus and Staphylococcus aureus. Three antibacterial substances were isolated and purified by column chromatography and recrystallization. Compounds I and III showed activity against all the tested bacterias and compound II exhibited the activity against B. subtilis and B. cereus S. aureus. Compound I was examined antimicrobial activity against B. subtilis, B. cereus and S. aureus by optical density using Bioscreen C. Compound I showed strong growth inhibition at 10 ppm on B. subtilis and B. cereus for 72 hrs, and at 25 ppm on S. aureus. On the basis of spectrometric studies including $1^H-NMR$, ${13}^C-NMR$, DEPT, IH-lH COSY, HMQC, HMBC and IR, compounds I, II and III were identified as $(E)-8{\beta}(17)-epoxylabd-12-ene-15,16-dial\;(C_{20}H_{30}O_3,\;MW=318)$, galanolactone $(C_{20}H_{30}O_3\;MW=318)$ and galanal A $(C_{20}H_{30}O_3,\;MW=318)$, respectively. These results are the first reports on the isolation of $(E)-8{\beta}(17)-epoxylabd-12-ene-15,16-dial, galanolactone and galanal A from the rhizome of Zingiber mioga.

Identification of NMR Data for ginsenoside Rg1 (Ginsenoside Rg1의 NMR 데이터 동정)

  • Lee, Dae-Young;Cho, Jin-Gyeong;Lee, Min-Kyung;Lee, Jae-Woong;Park, Hee-Jeong;Lee, Youn-Hyung;Yang, Deok-Chun;Baek, Nam-In
    • Journal of Ginseng Research
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    • v.32 no.4
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    • pp.291-299
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    • 2008
  • The fresh ginseng roots were extracted in aqueous methanol (MeOH), and the obtained extracts were partitioned using ethyl acetate (EtOA), n-butanol (n-BuOH), and water, successively. The repeated silica gel column chromatography for n-BuOH fraction afforded a purified ginsenoside $Rg_1$. The physico-chemical, spectroscopic and chromatographic data of ginsenoside $Rg_1$, such as crystallization characteristics, melting point, specific rotation, infrared spectrometry (IR) data, fast atom bombardment/mass spectrometry (FAB/MS) data, nuclear magnetic resonance (NMR) data, retention factor (Rf) in thin layer chromatography (TLC) experiment, and retention time (r.t.) in HPLC analysis, were measured and compared with those reported in literatures. Especially, the previous literatures reported different data for ginsenoside $Rg_1$ in the $^{1}H-$ and $^{13}C$-NMR experiments. This paper gives the exactly assigned NMR data through 2D-NMR experiments, such as $^{1}H-^{1}H$ correlation spectroscopy (COSY), hetero nuclear single quantum correlation (HSQC), and hetero nuclear multiple bond connectivity (HMBC).

Isolation of Magnolialide and Artesin from Cichorium intybus: Revised Structures of Sesquiterpene Lactones

  • Park, Hee-Juhn;Kwon, Sang-Hyuk;Yoo, Ki-Oug;Jung, Won-Tae;Lee, Kyung-Tae;Kim, Joo-Il;Han, Yong-Nam
    • Natural Product Sciences
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    • v.6 no.2
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    • pp.86-90
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    • 2000
  • Two known eudesmanolides, magnolialide and artesin, were isolated from the roots of Cichorium intybus. Their structures were confirmed by HMBC and NOESY NMR spectral interpretation. Therefore, guaianolides and eudesmanolides that have been previously reported should be revised.

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A New Triterpenoid Saponin from the Tropical Marine Sponge Lipastrotethya sp. (열대 해면동물 Lipastrotethya sp.에서 분리된 사포닌 화합물)

  • Eom, Tae-Yang;Lee, Yeon-Ju;Lee, Hyi-Seung
    • Ocean and Polar Research
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    • v.38 no.4
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    • pp.287-294
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    • 2016
  • Marine sponges have been a remarkably rich source of pharmacologically active and structurally diverse natural products. As a part of our continuing search for novel secondary metabolites of biomedical importance from marine invertebrate, we encountered the sponge Lipastrotethya sp. from Chuuk, Micronesia. The crude organic extract of this animal exhibited considerable cytotoxicity against the K562 cell line. Guided by the $^1H$ NMR analysis, flash chromatography of the crude extract followed by HPLC yielded a new triterpene glycoside, along with ten known saponins of the sarasinoside class. The structure of this new compound was determined by combined spectroscopic methods such as COSY, HSQC and HMBC experiment. Among these metabolites, six compounds exhibited moderate cytotoxicity against ACHN, MDA-MB-231, NCI-H23 and NUGC-3 cell lines.

Isolation and Structure Identification of Antifungal Substance from Aspergillus terreus (Aspergillus terreus로부터 항진균성 물질의 분리 및 구조분석)

  • Kim, Keun-Ki;Park, Ki-Hun;Moon, Suk-Sik;Kang, Kyu-Young
    • Applied Biological Chemistry
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    • v.40 no.6
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    • pp.593-596
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    • 1997
  • In the course of search antagonistic fungi from soil in green house, four kind of fungi (AF1, AF2, AF3, AF4) were isolated, which have activities against Phytophthora capsici, Botrytis cinera, Rhizoctonia solani, Pythium ultimum and Fusarium oxysporum. The AF2 was identified according to the morphological description of Aspergillus terreus. This antagonistic fungus inhibiting various plant pathogens was effective to reduce disease incidence of cucumber seedlings caused by mixed inoculum of Rhizoctonia solani, Pythium ultimum and Fusarium oxysporum. Antifungal compound I was isolated and purified by fresh chromatography from A. terreus. The $^1H$ and $^{13}C$ assignment of compound I was achieved from two-dimensional $^1H-^1H\;COSY$, HMQC, HMBC with the add of homonuclear and heteronuclear double resonance experiment. The compound I was identified butyrolactone I (${\alpha}$-oxo-${\beta}$-(p-hydroxyphenyl)-${\gamma}$-(p-hydroxy-m-3,3-dimethyl-allylbenzyl)-${\gamma}$-methoxycarbonyl-${\gamma}$-butyrolactone, $C_{24}H_{24}O_7$, M.W.=424).

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Isolation of Antifungal Compound and Biocontrol Potential of Lysobacter antibioticus HS124 against Fusarium Crown Rot of Wheat

  • Monkhung, Sararat;Kim, Yun-Tae;Lee, Yong-Seong;Cho, Jeong-Yong;Moon, Jae-Hak;Kim, Kil-Yong
    • Korean Journal of Soil Science and Fertilizer
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    • v.49 no.4
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    • pp.393-400
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    • 2016
  • Fusarium graminearum is the main cause of substantial economic loss in wheat production. The aim of this study is to investigate biocontrol potential of Lysobacter antibioticus HS124 against F. graminearum and to purify an antifungal compound. In preliminary study, n-butanol crude extract revealed destructive alterations in the hyphal morphology of F. graminearum and almost degraded with $1,000{\mu}g\;mL^{-1}$ concentration. For further study, the antifungal compound extracted from the n-butanol crude extract of L. antibioticus HS124 was identified as N-Butyl-tetrahydro-5-oxofuran-2-carboxamide ($C_9H_{16}NO_3$) using NMR ($^1H-NMR$, $^{13}C-NMR$, $^1H-^1H\;COSY$, HMBC, and HMQC), and HR-ESI-MS analysis. To our knowledge, N-Butyl-tetrahydro-5-oxofuran-2-carboxamide may be a novel compound with molecular weight of 186.1130. The minimum inhibitory concentration value of antifungal compound was $62.5{\mu}g\;mL^{-1}$ against F. graminearum. In an in vivo pot experiment, crown rot disease from F. graminearum was inhibited when wheat seeds were treated with both HS124 culture and F. graminearum. Growth of wheat seedling was enhanced by treatment of HS124 compared to control. Our results suggest that L. antibioticus HS124 characterized in this study could be successfully used to control F. graminearum and could be used as an alternative to chemical fungicides in modern agriculture.

Structural Identification of Antibiotics from Pseudomonas sp. RRj 228, a Antifungal Activity of Collectotrichum acutatum Causing Anthracnose on Pepper (Pseudomonas sp. RRj 228이 분비하는 항균물질의 동정과 고추탄저균 C. acutatum에 대한 항균활성)

  • Jeon, Sang-Yoon;Kim, Yong-Gyun;Lee, Sang-Mong;Son, Hong-Joo;Park, Hyean-Cheal;Kim, Sun-Tae;Park, Ki-Do;Kang, Ui-Gum;Kim, Keun-Ki
    • Journal of Life Science
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    • v.20 no.8
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    • pp.1254-1260
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    • 2010
  • Microorganisms near the plant rhizosphere usually inhabit the surface or the inside of the plant roots and have a direct effect on plant growth by secreting plant growth promoters or antagonistic materials which protect the root zone system from various pathogens. This study was carried out to identify and isolate the antagonistic materials after isolation of microorganisms showing high antagonistic activities, in hopes of contributing to the development of sustainable agriculture and the preservation of agricultural environments. A number of antagonistic bacteria were isolated from paddy soil. Among isolates, RRj 228 showed plant growth promotion and antagonistic activity. RRj 228 was identified as Pseudomonas sp. according to the results of physiological properties and genetic methods. On the basis of the results of anti-fungal spectrum against several pathogens by RRj 228, the antagonistic effect of the isolate against Botrytis cinerea, Pythium ultimum, Phytopthola capsici, and Rhizoctonia solani, especially against red-pepper anthracnose caused by Colletotrichum acutatum, was remarkable. The experiment evaluating the biological control effect by RRj 228 revealed that the $ED_{50}$ value by the RRj 228 culture against C. acutatum, R. solani and P. ultimum were 0.14 mg/ml, 0.16 mg/ml and 0.29 mg/ml, respectively. An antagonistic substance was isolated and purified by several chromatographies from the RRj 228 culture. The $^1H$ and $^{13}C$ assignment of the antagonistic substance was achieved from two-dimensional $^1H-^1H$ COSY, HMQC, and HMBC. Finally, the antagonistic substance was identified as Phenazine-1-carboxylic acid ($C_{13}H_8N_2O_2$, M.W.=224).