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

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NMR Spectral Analysis of Steroids Isolated from the Sponge Penares incrustans (핵자기공명분광기를 이용한 해면동물 Penares incrustans에서 분리된 스테로이드 화합물의 분석)

  • 서영완
    • Journal of Aquaculture
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    • v.15 no.3
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    • pp.139-143
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    • 2002
  • Saringosterols have been isolated from the sponge Penares incrustans. The structure of these compounds have been determined by extensive 2-D NMR experiments such as $ ^1 H$ COSY, HMQC, and HMBC and by comparison with published data. Assignment for carbons of saringosterols for the first time has been done.

지초뿌리 유래의 기능성 물질의 탐색

  • 문영환;조정용;위지향;문제학;박근형
    • Proceedings of the Korean Society of Postharvest Science and Technology of Agricultural Products Conference
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    • 2003.10a
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    • pp.134.2-135
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    • 2003
  • 지초(Lithospermum efthrorhizon)뿌리는 예로부터 한방약제로 이용되어져 왔으며, 지초 뿌리에 함유된 naphtoquinon계 색소물질인 shikonin은 항암, 항균, 항바이러스, 항염증 등의 효과가 있다고 보고되었다. 그러나 지초뿌리에 함유된 기능성 물질에 관한 연구는 미비한 실정이다. 이에 본 연구에서는 지초뿌리에서 기능성 물질의 탐색 및 기능성 해명연구를 위하여 지초뿌리를 ethanol로 추출한 후 이 추출물을 n-hexane, EtOAc, MeOH로 순차적으로 추출하여 MeOH추출물을 얻었다. 이 MeOH추출물을 silica gel adsorption column chromatography, ODS column chromatography, Sephadex LH-20 column chromatography로 순차 정제한 후 Shodex Asahipak column을 이용한 GPC-HPLC에 의해 활성 물질을 분리하였다. 분리된 물질들은 1H-NMR, 13C-NMR, COSY, HSQC, HMBC, FAB-MS 등의 기기분석을 통해 당 관련 화합물인 것으로 판명되었다.

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Synthesis, Characterization and in Vitro Identification of $N^7-Guanine$ Adduct of 2-Bromopropane

  • Zhao, Long-Xuan;Kim, Eun-Kyung;Lim, Hyun-Tae;Moon, Yoon-Soo;Kim, Nam-Hee;Kim, Tae-Hyung;Choi, Heesung;Chae, Whigun;Jeong, Tae-Cheon;Lee, Eung-Seok
    • Archives of Pharmacal Research
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    • v.25 no.1
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    • pp.39-44
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    • 2002
  • Recently, we have reported that 2-bromopropane might have an immunotoxic potential in rats when exposed for 28 days. In the present studies, the possibility of 2i-deoxyguanosine abduct formation by 2- bromopropane was investigated in vitro to elucidate molecular mechanism of 2-bromopropane-induced immunosuppression. $N^7-Guanine adduct$ of 2'-bromopropane (i.e., $N^7-isopropyl$ guanine) was chemically synthesized and structurally characterized by analysis of UV,$^1H-NMR,{\;}^{13}C-NMR$, COSY and fast atom bombardment mass spectrometry to use as a reference material. Incubation of 2'-deoxyguanosine with an excess amount of 2-bromopropane in PBS buffer solution, pH 7.4, at $37^{\circ}C$ for 16 h, followed by a thermal hydrolysis, produced a detectable amount of $N^7-isopropyl$ guanine by an HPLC and UV analysis. The present results suggest that 2-bromopropane might form a DNA adduct in $N^7-position$ of 2'-deoxyguanosine at 3 Physiological condition.

Lipolysis Effect of Daucosterol Isolated from Mulberry (Morus alba) Leaves (뽕잎으로부터 순수분리한 daucosterol의 lipolysis 효과)

  • Li, Ke;Lee, Mi Lim;Que, Lu;Li, Mae;Kang, Jum Soon;Choi, Yung Hyun;Kim, Kyung Mi;Jung, Jae-Chul;Hwang, Dae Youn;Choi, Young Whan
    • Journal of Life Science
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    • v.27 no.12
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    • pp.1500-1506
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    • 2017
  • Plants are reservoirs of naturally occurring chemical compounds and of structurally diverse bioactive molecules. The aim of this investigation was to screen for the presence of phytochemicals responsible for the lipolysis activity in mulberry (Morus alba) leaves, which are important in traditional Asian medicinal plants. Powdered mulberry leaves were extracted with hexane, ethyl acetate, and methanol. Daucosterol was isolated from the EtOAc extract of mulberry leaves, and its structure was elucidated by NMR spectral analyses. The NMR assignments for the compound were determined using $^1H$, $^{13}C$, DEPT, COSY, HSQC, and HMBC NMR spectral data. Daucosterol showed a concentration-dependent lipolysis activity that may impart medicinal properties that can be exploited by medical practitioners for the treatment of various diseases. However, further studies should be conducted to elucidate additional mechanisms of daucosterol.

Studies on the Constituents of Ulmus parvifolia (참느릅나무의 성분에 관한 연구)

  • Moon, Young-Hee;Rim, Gi-Ryong
    • Korean Journal of Pharmacognosy
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    • v.26 no.1
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    • pp.1-7
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    • 1995
  • The bark of Ulmus parvifolia Jacq. (Ulmaceae) has been used for the treatment of gonorhea, edema, scabies and eczema marginatum. Previous investigations conducted with the heartwood and leaves have demonstrated it to contain sesquiterpenes as well as fat acids from the heartwood and flavonol glycosides from leaves. However, no phytochemical work has been done on the bark parts of this plant. Investigation of the phytochemical constituents in the barks of U. parvifolia has resulted in the isolation of sterols, sterol glucoside and a catechin glycoside, $(+)-catechin\;7-O-{\alpha}-{_L}-rhamnopyranoside$, all of which were isolated for the first time from this plant. Sterols were consisted of the three components, ${\beta}-sitosterol$, stigmasterol and campesterol in a ratio of 92.1:4.1:3.8, and sterol glucoside was identified as ${\beta}-sitosterol\;3-O-{\beta}-{_D}-glucoside$. The structure of the catechin $7-O-{\alpha}-{_L}-rhamnoside$ was established primarily by analysis of $^1H-and$ COSY-45 NMR, HMQC and HMBC and EI mass spectra of the heptaacetate. Especially, HMBC spectrum provides effective way for the determination of the point of attachment of the rhamnosyl group to catechin moiety.

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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).

Identification of insecticidal compounds from Streptomyces sp. no. 46 (Streptomyces sp.no. 46이 생산하는 살충성 물질의 구조 동정)

  • Oh, Sei-Ryang;Lee, Hyeong-Kyu;Koo, Bon-Tak;Choi, Soo-Keun;Park, Sang-Gu;Shin, Byung-Sik;Park, Seung-Hwan;Kim, Jeong-Il
    • Applied Biological Chemistry
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    • v.37 no.2
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    • pp.110-114
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    • 1994
  • In searching for new insecticidal compounds from soil microorganisms, strains of streptomyces species showed insecticidal activities on Musca domestica and Bombyx mori were selected. Compounds I-IV, which were isolated from the metabolites of no. 46 strain, were identified as piericidin $C_1$, $C_2$, $C_3$ and $D_1$, respectively by UV and NMR data analyses.

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Adipocyte Differentiation Inhibitor Isolated from the Barks of Phellodendron amurense (황백(Phellodendri Cortex)으로부터 분리한 지방세포 분화 저해물질)

  • Kim, Kyung-Hee;Ahn, Soon-Cheol;Lee, Myung-Sun;Kweon, Oh-Song;Oh, Won-Keun;Kim, Min-Soo;Sohn, Cheon-Bae;Ahn, Jong-Seog
    • Korean Journal of Food Science and Technology
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    • v.35 no.3
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    • pp.503-509
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    • 2003
  • For the development of the anti-obesity natural drug, the inhibitor of adipocyte differentiation was screened from Korean traditional medicinal plants. Phellodendri Cortex was selected as a candidate of adipocyte differentiation inhibitor. An inhibitory compound PC-4 was purified from the methanol (MeOH) extract of Phellodendri Cortex using silica gel and ODS RP-18 column chromatography and HPLC. PC-4 was obtained as yellow powder; UV ${\lambda}_{max}$ (MeOH): 230, 260, 340 and 430 nm. The chemical structure of PC-4 was determined as an isoquionoline alkaloid, berberine, on the basis of various NMR experiments including $^1H-\;and\;^{13}C-NMR$. The PC-4 inhibited the differentiation of preadipocyte NIH-3T3 L1 cells at a concentration of $1\;{\mu}g/mL$.

Sesquiterpene Glycosides from the whole Plant Extract of Youngia japonica (뽀리뱅이 전초로부터 분리한 Sesquiterpene 배당체)

  • Kim, Mi-Ri;Cha, Mi-Ran;Choi, Yeon-Hee;Choi, Chun-Whan;Choi, Sang-Un;Kim, Young-Sup;Kim, Young-Kyoon;Kim, Young-Ho;Ryu, Shi-Yong
    • Korean Journal of Pharmacognosy
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    • v.41 no.2
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    • pp.103-107
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    • 2010
  • Extensive phytochemical investigation of the methanol extract from the whole plant of Youngia japonica (Asteraceae) led us to the isolation of a new guaiane-type sesquiterpene (1), together with three related guaianolides, youngiajaponicoside A (2), crepiside H (3) and crepeside E (4). The chemical structure of 1 was elucidated by the aid of spectroscopic analyses including 2D-NMR experiments (COSY, HMBC, HMQC and ROESY). The isolated components (1-4) were evaluated for the inhibitory effect on the proliferation of four cultured human tumor cell lines such as A549, SK-OV-3, SK-MEL-2 and HCT-15, in vitro.

Alkyl Glycosides from the Flowers of Magnolia obovata (황목련 꽃으로부터 Alkyl Glycoside의 분리 동정)

  • Oh, Eun-Ji;Seo, Kyeong-Hwa;Kwon, Jung-Hwa;Lee, Dae-Young;Baek, Nam-In
    • Journal of Applied Biological Chemistry
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    • v.58 no.3
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    • pp.233-236
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    • 2015
  • The flowers of Magnolia obovata were extracted with aqueous MeOH and fractionated into EtOAc, n-BuOH, and $H_2O$ fractination. Three alkyl glycosides were isolated from the EtOAc fraction through repeated silica gel and ODS column chromatography. The structures were identified to be 2-methylbutan-1-ol-${\beta}$-$\small{D}$-galacto-pyranoside (1), 2-methylbutan-1-ol-${\beta}$-$\small{D}$-glucopyranoside (2), and 2-methylpropan-1-ol-${\beta}$-$\small{D}$-glucopyranoside (3) on the basis of spectroscopic analyses such as fast atom bombardment mass spectrometry, infrared spectroscopy, 1D nuclear magnetic resonance (NMR) ($^1H$ and $^{13}C-NMR$), and 2D NMR (gCOSY, gHSQC, and gHMBC). These compounds were isolated for the first time from the flower of M. obovata in this study.