• Title/Summary/Keyword: HMBC

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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).

Flavanone Glycoside from the Fruits of Chaenomeles sinensis

  • Kim, Ho-Kyoung;Jeon, Won-Kyung;Ko, Byoung-Seob
    • Natural Product Sciences
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    • v.6 no.2
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    • pp.79-81
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    • 2000
  • Investigation of the fruits of Chaenomeles sinensis (Rosaceae) resulted in the isolation of a minor flavonoid. The structure of flavanone glycoside was determined to be as $2-hydroxynaringenin-7-O-{\beta}-glucoside$ on the basis of FAB-MS and spectral evidence, especially by 2D-NMR $(^1H-^1H\;COSY,\;HMQC,\;HMBC\;and\;NOESY)$.

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Verticilloside, a New Daucosteryl Derivative from the Seeds of Malva verticillata

  • Kim, Jeong-Ah;Yang, Seo-Young;Kang, Sang-Jin;Kim, Young-Ho
    • Natural Product Sciences
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    • v.17 no.4
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    • pp.350-353
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    • 2011
  • A new daucosteryl derivative, verticilloside (1), was isolated from the seeds of Malva verticillata L. (Malvaceae). The structure was determined to be 3-O-[${\beta}$-D-(6'-linoleoyl)glucopyranosyl]-${\beta}$-sitosterol based on spectroscopic analyses ($^1H$ and $^{13}C$-NMR, DEPT, COSY, HMQC, and HMBC) and chemical reactions.

Isolation of $n-Butyl-{\beta}-D-fructopyranoside$ from Gastrodia elata Blume

  • Pyo, Mi-Kyung;YunChoi, Hye-Sook;Kim, Yong-Kwon
    • Natural Product Sciences
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    • v.12 no.2
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    • pp.101-103
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    • 2006
  • In the course of the continual work on the fresh tubers of Gastrodia elata, a fructoside constituent was isolated from the n-butanol soluble fraction prepared from the methanol extract. The structure of this compound was identified as $n-butyl-{\beta}-D-fructopyranoside$ from various spectroscopic data including $^1H-\;and\;^{13}C-NMR$, HMQC, HMBC, and FABMS.

Revision of Structures of Flavanoids from Scutellaria indica and Their Protein Tyrosine Phosphatase 1B Inhibitory Activity

  • Min, Byung-Sun
    • Natural Product Sciences
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    • v.12 no.4
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    • pp.205-209
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    • 2006
  • The structures of flavonoids, 2(S)-5,7-dihydroxy-8,2'-dimethoxyflavanone (1), wogonin (2), 2(S)-5,7, 2'-trihydroxy-8-methoxyflavanone (3), and 2(S)-5,2',5'-trihydroxy-7,8-dimethoxyflavanone (4), isolated from Scutellaria indica were revised on the basis of 2D NMR spectroscopy, including to gCOSY, gHSQC, and gHMBC. Compounds 1-4 were tested in vitro protein tyrosine phosphatase 1B (PTP1B) inhibitory activity. Compounds 2 and 4 exhibited weak PTP1B inhibitory activity with $IC_{50}$ values of 208 and $337{\mu}M$, respectively.

A Study on the Chemical Constituents from Marine Sponge Luffariella sp. (해면 Luffariella sp.의 화학적 성분 연구)

  • Park, Sun Ku;Kim, Sung Soo;Park, Jun Dae;Hong, Jung Sun;Kim, In Kyu
    • Journal of the Korean Chemical Society
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    • v.39 no.7
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    • pp.559-563
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    • 1995
  • The three metabolites, Germacrene alcohol(1), Aaptamine(2) and Hexacyclic terpene(3) were isolated from Marine Sponge Luffariella sp., collected in October 1992, Manado Bay, Sulawesi in Indonesia showed in vitro activity against KB cancer cell line, and structure assignment for 1 was corrected by comparison of their spectral data with the literature $values^1$. Their structure were elucidated by $^1H$, $^13C$ NMR, $^1H$ $^13C$(1 bond) Heteronuclear Multiple Quantum Coherence Spectroscopy$(HMQC)^2$, $^1H$ $^13C$(2 and 3 bond) Heteronuclear Multiple Bond Correlation Spectroscopy$(HMBC)^3$, Electron Impact Mass Spectroscopy(EI ms), Ultra-violet Spectroscopy(UV) and Infrared Spectroscopy(IR).

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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.

A New Compound Isolation and Structure Analysis from Phellodendron Amurense Fruit Extract (황벽나무 열매 추출물로부터 신규 화합물의 분리 및 구조분석)

  • Kim, Young-Hee;Choi, Jung Eun;Hong, Jin-Young;Jo, Chang Wook;Lee, Jeung-Min;Kim, Soo Ji
    • Journal of the Korean Wood Science and Technology
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    • v.41 no.4
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    • pp.269-275
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    • 2013
  • Antifungal and insecticidal activity of Korean traditional medicinal plants was carried out to develop natural material for the development of organic cultural heritage conservation. As a result, Phellodendron amurense fruit was finally selected as a candidate of antifungal and insecticidal natural material. An novel active compound was purified from the ethylacetate fraction of Phellodendron amurense fruits using silica gel and Sephadex LH-20 column chromatography and PTLC. The compound was obtained as yellow oil form; UV ${\lambda}_{max}$(MeOH): 260 nm. The chemical structure of novel compound was determined as (4'-ethyl-2'-methylfuranyl)-6-methoxy-7-methylnona-2E,4E,6Z,8E-tetraenoic acid on the basis of various NMR experiments including $^1H$- and $^{13}C$-NMR, HMQC, HMBC and ESI-mass spectrum.

Development of Biologically Active Compound from Edible Plant Sources-XV. Isolation of Triterpene Glycosides from the Leaf of Petasites japonicus (식용식물자원으로부터 활성물질의 탐색-XV. 머위(Petasites japonicus)잎으로부터 Triterpene 배당체의 분리)

  • Bang, Myun-Ho;Park, Jin-Kyu;Song, Myoung-Chong;Yang, Hye-Joung;Yoo, Jong-Su;Ahn, Eun-Mi;Kim, Dae-Keun;Baek, Nam-In
    • Applied Biological Chemistry
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    • v.48 no.4
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    • pp.421-424
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    • 2005
  • The leaf of Petasites japonicus was extracted with 80% aqueous MeOH and solvent fractionated with EtOAc, n-BuOH and water successively. From the EtOAc fractions, two triterpenoids were isolated through the repeated silica gel and ODS column chromatographies. The chemical structures of the isolated terpenoids were determined as rosamutin (1) and peduncloside (2) through the interpretation of several spectral data including 2D-NMR such as $^1H-{^1H}$ gCOSY, gHSQC and gHMBC.