• Title/Summary/Keyword: COSY

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The Structure of Kushenol M from Sophora flavescens

  • Ryu, Shi-Yong;Lee, Seung-Ho;No, Zaesung;Kim, Kye-Young;Lee, Sueg-Geun;Ahn, Jong-Woong
    • Archives of Pharmacal Research
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    • v.18 no.1
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    • pp.41-43
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    • 1995
  • The linkage pattem of two side chains i.e., a isopentenyl and a lavandulyl group in kushenol M(I), a flavonoid from Sophora flavescens was established by the aid of 2-D NMR techniques, especially DEPT, ${13}C-^1H$ COSY and COLOC experiments. Thus, I was unequivocally determined as (2R, 3R)-5, 7, 2', 4'-tetrahydroxy-6-isopentenyl-8-lavandulyflavanonol.

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Two New Phenolic Glycosides from Curculigo orchioides

  • Zuo, Ai-Xue;Shen, Yong;Jiang, Zhi-Yong;Zhang, Xue-Mei;Zhou, Jun;Lu, Jun;Chen, Ji-Jun
    • Bulletin of the Korean Chemical Society
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    • v.32 no.3
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    • pp.1027-1029
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    • 2011
  • Two new phenolic glycosides were isolated from the rhizomes of Curculigo orchioides Gaertn.. Based on comprehensive spectroscopic analyses including IR, MS, 1D- and 2D NMR (COSY, HSQC, and HMBC), their structures were elucidated as 3-hydroxyl-5-methyphenol-1-O-[${\beta}$-D-glucopyranosyl-($1{\rightarrow}3$)-${\beta}$-D-glucopyranoside (1) and 1',3'-dimethoxyl-4-hydroxyalangifolioside (2).

Isolation and Identification of 13-Deacetyl-taxchinin I, a New Taxoid from Plant Cell Cultures of Taxus chinensis (식물세포 Taxus chinensis 배양으로부터 신물질 13-Deacetyl-taxchinin I의 분리 및 동정)

  • 김진현;기은숙;유시용;최형균;홍승서;이현수
    • KSBB Journal
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    • v.15 no.6
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    • pp.560-565
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    • 2000
  • 13-Deacetyl-taxchinin I, a taxoid having a rearranged 11(15\longrightarrow1)-abeo-taxane skeleton, has been isolated and identified from plant cell cultures of Taxus chinensis. The compound has not previously been encountered in nature. Its structure was elucidated by 1-and 2D NMR techniques including H-H COSY, HMQC, and HMBC experiments. This taxoid also provides information for better understanding of structure-activity relationships and biosynthesis, as well as improving the quality control of paclitaxel production.

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Anticomplementary Activity of Ergosterol Peroxide from Naematoloma fasciculare and Reassignment of NMR Data

  • Kim, Dong-Seon;Baek, Nam-In;Oh, Sei-Ryang;Jung, Keun-Young;Lee, Im-Seon;Kim, Jung-Hee;Lee, Hyeong-Kyu
    • Archives of Pharmacal Research
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    • v.20 no.3
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    • pp.201-205
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    • 1997
  • A very high content (at least 0.23%) of ergosterol peroxide was isolated from Naematoloma fasciculare Karst. Not only ergosterol peroxide but also ergosterol showed very strong anticomplementary activity on the classical pathway, the $IC_{50}$ values being $5.0 {\mu}M$ and $1.0 {\mu}M$, respectively. The $ ^{1}H $and $^{13}C$ NMR data of ergosterol peroxide were revised and completely assigned by DEPT, $^{1}H-^{1}H$ COSY, HMQC and HMBC correlations.

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Cytotoxic Polyketides from the Marine Sponge Discodermia calyx

  • Shinde, Pramod B.;Mansoor, Tayyab A.;Luo, Xuan;Hong, Jong-Ki;Lee, Chong-O.;Jung, Jee-H.
    • Bulletin of the Korean Chemical Society
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    • v.28 no.6
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    • pp.990-994
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    • 2007
  • Bioassay-guided fractionation of the MeOH extract from the sponge Discodermia calyx collected off the coast of Jeju Island, South Korea, led to the isolation of a polyketide, icadamide C (1), along with previously reported theopederin K (3). Structure elucidation was performed by a combination of high resolution mass and 2D-NMR (principally COSY, HMBC, HSQC, and NOESY) spectroscopy. Stereochemistry of compound 1 was determined as 2R*, 3R*, 6R*, 10S*, 11S*, 12R*, 13S*, 15R* and 2'S by NMR data and Marfey analysis. Isolated metabolites displayed potent cytotoxic activity against a small panel of five human solid tumor cell lines with ED50 values of less than 0.1 μg/mL.

Studies on the Chemical Constituents of Lysimachia Clethroides (큰까치수영의 구성성분)

  • 김진숙;김형자;박호군
    • YAKHAK HOEJI
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    • v.37 no.4
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    • pp.325-330
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    • 1993
  • Four flavonoide glycosides and (-)-Epicatechin were isolated from the aqueous extracts of dried whole part of Lysimachia clethroides Duby(Primulaceae). They were 3-0-Methyl-quercetin-7-0-[$\alpha$-L- rhamnopyranosyl (1-2) glucopyranoside], Quercetin-3-0-$\beta$-D-glucopyranoside, Kaempferol-3-0-$\beta$-D-glucopyranoside, Kaempferol-3-0-[$\alpha$-L-rhamnopyranosyl (1-6)-$\beta$-D-glucopyranoside] and (-)-Epicatechin. 3-0-[$\alpha$-L-rhamnopyranosyl (1-6)-$\beta$-D-glucopyranoside]and (-)-Epicatechin. 3-0-Methyl-quercetin-7-0-[$\alpha$-L-rhamnopyranosyl (1-2)-$\beta$-D-glucopyranoside] and (-)-Epicatechin were first isolated from this plant. Their structures were elucidated by spectral analysis [$^{1}$H-, $^{13}C-$ NMR, $^{1}$H-$^{1}$H-COSY, DEPT-analysis, HMQC(Heteronuclear multiple quantum coherence), FAB-MS].

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Flavonoid Glycosides from the Flowers of Pulsatilla koreana Nakai

  • Seo, Kyeong-Hwa;Jung, Jae-Woo;Nhan, Nguyen Thi;Lee, Youn-Hyung;Baek, Nam-In
    • Natural Product Sciences
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    • v.22 no.1
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    • pp.41-45
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    • 2016
  • Extraction and fractionation of Pulsatilla koreana flowers followed by, repeated open column chromatography for EtOAc and n-BuOH fractions yielded four flavonoid glycosides, namely, astragalin (1), tiliroside (2), buddlenoide A (3), and apigenin-7-O-(3"-E-p-coumaroyl)-glucopyranoside (4). The chemical structures of these flavonoid glycosides were elucidated on the basis of various spectroscopic methods including electronic ionization mass spectrometry (EI-MS), 1D NMR ($^1H$, $^{13}C$, DEPT), 2D NMR (gCOSY, gHSQC, gHMBC), and infrared (IR) spectrometry. This study represents the first report of the isolation of the flavonoid glycosides from the flowers of P. koreana.

Study on the Antitumor Activity of Tripterygium Regelii Sprague (미역줄나무의 항암활성에 관한 연구)

  • Park, Wan-Su
    • Journal of Physiology & Pathology in Korean Medicine
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    • v.19 no.2
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    • pp.441-445
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    • 2005
  • Tripterygium regelii has been used as an oriental medicine, especially antiparasitic, anti-inflammatory and detoxifying agents in East asia. During our research to develop new antitumor agents from natural products, MeOH ext. and CH2Cl2 ext. of Tripterygium regelii showed the potent antitumor activity. In order to purify active compounds from Tripterygium regelii, activity-guided fractionation was carried out. Silica gel and RP-18 column chromatography for the active fraction led to the isolation of two compounds and their antitumor activities were studied. Those two compounds didn't show potent antitumor activity against human tumor cell lines. The structure of two compounds were determined by $^1H-NMR$, $^{13}C-NMR$, DEPT, $^1H-^{13}C$ COSY and IR spectrum. Compound I and Compound II were turned out to be Celastrol, and ${\beta}-sitosteryl-3-o-{\beta}-D-glucopyranoside$ respectively.

Isolation of Sinapic Acid Esters from Raphani Semen (내복자(Raphani Semen)로부터 Sinapic acid esters의 분리)

  • Kang, Eun-Jung;Ko, Byoung-Seob;Kim, Ho-Kyoung
    • Korean Journal of Pharmacognosy
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    • v.31 no.4
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    • pp.434-437
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    • 2000
  • Two sinapic acid esters were isolated from the methanol extract of Raphani Semen. The structures were elucidated on the basis of spectroscopic methods $(^1H-NMR,\;^{13}C-NMR,\;HMQC,\;^1H-^1H\;COSY\;and\;HMBC)$ and were identified as methyl sinapate (1) and ${\beta}-D-(3-O- sinapoyl)fructofuranosyl-{\alpha}-D-(6-O-sinapoyl)glucopyranoside$ (2). Compound 1 was first isolated from the genus of Raphanus.

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Anti-Human Immunodeficiency Virus-Type 1 Activity of Constituents from Juglans mandshurica

  • Min, Byung-Sun;Lee, Hyeong-Kyu;Lee, Sang-Myung;Kim, Young-Ho;Bae, Ki-Hwan;Otake, Toru;Nakamura, Norio;Hattori, Masao
    • Archives of Pharmacal Research
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    • v.25 no.4
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    • pp.441-445
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    • 2002
  • Three naphthalene glycosides (1-3), four flavonoids (4-7), and two galloyl glycosides (8-9) were isolated from the stem-bark of Juglans mandshurica (Juglandaceae). Their structures were determined by chemical and spectral means, including to 2D-NMR (COSY, HMQC, and HMBC) experiments. Amongst the isolated compounds, taxifolin (4) showed the most potent HIV-induced cytopethic activity against MT-4 cells with complete inhibitory concentration ($IC_{100}$) value of $25{\;}{\mu\textrm{g}}/ml$ and maximum cytotoxic concentration ($CC_{100}$) value of above $100{\;}{\mu\textrm{g}}/ml$. However, naphthalene glycosides (1-3), flavonoids (5-7)), and galloyl tannins (8-9) were inactive against anti-HIV-1 activity.