• Title/Summary/Keyword: NMR spectroscopic analysis

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Glycerides from the Aerial Parts of Garland (Chrysanthemum coronarium L.) and Their Inhibitory Effects on ACAT, DGAT, FPTase, and $\beta$-Secretase

  • Song, Myoung-Chong;Yang, Hye-Joung;Cho, Jin-Gyeong;Chung, In-Sik;Kwon, Byoung-Mog;Kim, Dae-Keun;Baek, Nam-In
    • Food Science and Biotechnology
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    • v.18 no.1
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    • pp.95-102
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    • 2009
  • The aerial parts of garland (Chrysanthemum coronarium L.) were extracted in 80% aqueous methanol (MeOH) and the concentrated extract was then partitioned using ethyl acetate (EtOAc), n-butanol (n-BuOH), and $H_2O$, successively. EtOAc and n-BuOH fractions resulted in 4 glycerides with the application of octadecyl silica gel and silica gel column chromatography. The chemical structures of the glycerides were determined using several spectroscopic methods, including nuclear magnetic resonance (NMR) and mass spectrometry (MS) as (2S)-1-O-palmitoyl-sn-glycerol (1), (2S)-1-O-oleoyl-2-O-oleoyl- 3-O-$\beta$-D-galactopyranosyl-sn-glycerol (2), (2S)-1-O-palmitoyl-2-O-linoleoyl-3-O-phosphorouscholine-sn-glycerol (3), and (2S)-1-O-linolenoyl-2-O-palmitoyl-3-O-[$\alpha$-D-galactopyrasyl-($1{\rightarrow}6$)-$\beta$-D-galactopyranosyl]-sn-glycerol (4). The free fatty acids of these glycerides were determined with gas chromatography (GC)-MS analysis following alkaline hydrolysis and methylation. These glycerides demonstrated an inhibitory effect on acyl-CoA: cholesterol acyltransferase (ACAT, compound 1: $45.6{\pm}0.2%$ at $100{\mu}g/mL$), diacylglycerol acyltransferase (DGAT, compound 1: $59.1{\pm}0.1%$ at $25{\mu}g/mL$), farnesyl protein transferase (FPTase, compound 2: $98.0{\pm}0.1%$; compound 3: $55.2{\pm}0.1%$ at $100{\mu}g/mL$), and $\beta$-secretase ($IC_{50}$, compound 4: $2.6{\mu}g/mL$) activity. This paper is the first report on the isolation of these glycerides from garland and their inhibitory activity on ACAT, DGAT, FPTase, and $\beta$-secretase.

Purification and Characterization of Glyoxalase I from Pleurotus ostreatus (Pleurotus ostreatus에서 분리된 Glyoxalase I의 특성)

  • Kim, Seong-Tae;Yang, Kap-Seok;Seok, Yeong-Jae;Huh, Won-Ki;Kang, Sa-Ouk
    • Korean Journal of Microbiology
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    • v.32 no.4
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    • pp.315-321
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    • 1994
  • Glyoxalase I was purified 2,294-fold from Pleurotus ostreatus by S-hexylglutathione affinity chromatography, Sephadex G-150 gel filtration chromatography and DEAE-sepharose A-50 CL-6B ion exchange chromatography with an overall yield of 21.7%. The molecular mass determined by gel filtration was found to be approx. 34 kDa. SDS-PAGE revealed that the enzyme consists of two identical subunits with a molecular mass of approx. 17 kDa. The K sub(m) values of this enzyme for methylglyoxal and phenylglyoxal were 0.39 mM and 0.22 mM, respectively. And this enzyme had a strong affinity for L-xylosone and hydroxypyruvaldehyde. The enzyme showed its optimal activity at pH 6.5-7.5 and at $40^{\circ}C$. $^1H$-NMR spectroscopic analysis of enzymic reaction showed that this enzyme catalyzes intramolecular proton transfer.

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Neuroprotective effects of phenolic compounds isolated from Spiraea prunifolia var. simpliciflora (조팝나무(Spiraea prunifolia var. simpliciflora)로부터 분리한 페놀 화합물의 신경세포 보호효과)

  • Oh, Seon Min;Choi, Doo Jin;Kim, Hyoung-Geun;Lee, Jae Won;Lee, Young-Seob;Lee, Jeong-Hoon;Lee, Seung-Eun;Kim, Geum-Soog;Baek, Nam-In;Lee, Dae Young
    • Journal of Applied Biological Chemistry
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    • v.61 no.4
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    • pp.397-403
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    • 2018
  • The leaves of Spiraea prunifolia were extracted with 80% aqueous MeOH and the concentrates were partitioned into EtOAc, n-BuOH, and $H_2O$ fractions. The repeated $SiO_2$ or ODS column, and medium pressure liquid chromatographies for the n-BuOH fraction led to isolation of two phenolic glucosides. The chemical structures of these compounds were determined as isosalicin (1) and crenatin (2) based on spectroscopic analyses including Nuclear magnetic resonance and MS. Extracts were analyzed using UPLC-MS/MS providing a short analysis time within 5 min using MRM technique. The concentration of crenatin was higher as 9.53 mg/g and isosalicin was lower as 0.65 mg/g. Neuroprotective effects of these compounds against hydrogen peroxide ($H_2O_2$)-induced neurotoxicity were evaluated. The results showed that exposure to $H_2O_2$ induced morphological changes, cell death and neurotoxicity in SK-N-MC cells. However, pretreatment with crenatin resulted in inhibition of morphological change, reduction of loss of cell viability and attenuation of neuronal damage. These results suggested that neuroprotective effect of crenatin isolated from S. prunifolia can be a good candidate for the development of health beneficial foods which can ameliorate the degenerative neuronal disease caused by oxidative stress.

Effect of Lignans Isolated from Schisandra chinensis Baillon on Seed Germination and Seedling Growth in Radish (오미자 (Schisandra chinensis Baillon)로부터 순수분리한 리그난이 무의 종자발아 및 유묘생육에 미치는 영향)

  • Park, Da-Jung;Kim, Youn-Han;Park, Se-Jin;Rajasekar, Seetharaman;Park, Young-Hoon;Kang, Jum-Soon;Son, Beung-Gu;Lee, Yong-Jae;Kim, Sun-Tae;Yoon, Moo-Kyoung;Choi, Young-Whan
    • Journal of agriculture & life science
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    • v.46 no.1
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    • pp.91-103
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    • 2012
  • The aim of this study was to develop a rapid and cheap bioassay of four lignans (schisandrin, schisandrin C, the gomisin A and gomisin N) isolated from Schizandra chinensis Baill on seed germination and seedling growth of the radish. Its structure was determined by analysis of MS and NMR spectroscopic data. Radish seeds immersed for 1 hr in the solutions of $10^{-5}M$, $10^{-6}M$ and $10^{-7}M$ of schisandrin, schisandrin C, gomisin A, and gomisin N, seed germination was observed with in 60 hr after all of the treatments. Also, the seeds were germinated faster compared to untreated controls. At early germination stage, 48 hr after the treatment of the lignans, the suppression of germination was observed from all treatments; the suppression due to schisandrin and gomisin A was the highest at the concentration of $10^{-6}M$. The level of suppression increased as the concentration increased in the treatment of schisandrin C and gomisin N. Percent germination of seed after 184 hr was increased 90% at all treatments. For the effects of lignan treatment on seedling growth in radish, the growth of hypocotyl was promoted by gomisin A and gomisin N at all concentrations. Root elongation was significantly promoted by schisandrin and gomisin N at $10^{-5}M$ and $10^{-6}M$, respectively. Fresh and dry weights of the seedlings were high at a low concentration of $10^{-7}M$, but significantly reduced by schisandrin C at a high concentration of $10^{-5}M$. The results of the germination activity and seedling growth of the lignans from S. chinensis suggest their potential use as natural growth regulators.