• Title/Summary/Keyword: sterol peroxide

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Sterol Peroxide Derivatives from the Marine Sponge Spirastrella abata (국내산 해면 Spirastrella abata로부터 Sterol Peroxide 유도체의 분리)

  • Im, Kwang-Sik;Nam, Kyung-In;Sim, Chung-J.;Jung, Jee-H.
    • Korean Journal of Pharmacognosy
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    • v.31 no.4
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    • pp.401-406
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    • 2000
  • Marine sponges are known to be a source of diverse sterols. In our study on the cytotoxic components of the marine sponge Spirastrella abata, $5{\alpha},8{\alpha}-epidioxy\;{\Delta}^6$ sterols (1-5) and $5{\alpha},8{\alpha}-epidioxy\;{\Delta}^{6,9(11)}$ sterols (6-7) were isolated. The structures were identified based on the analyses of $^1H-NMR,\;^{13)C-NMR$, and MS data. These compounds were assayed for cytotoxicity against 5 human solid tumor cell lines including A549, SK-OV- 3, SK-MEL-2, XF498, and HCT15.

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Isolation of Sterols from the Methanol Extracts of Cymbidium goeringii REICHB. fil (춘란(Cymbidiym goeringii REICHB. fil)의 메탄올 추출물로부터 Sterol 화합물의 분리)

  • Lee, Jin-Hee;Kim, Dong-Hyun;Bang, Myun-Ho;Yang, Hye-Joung;Bang, Sung-Hoon;Chung, In-Sik;Kwon, Byoung-Mog;Kim, Sung-Hoon;Kim, Dae-Keun;Park, Mi-Hyun;Baek, Nam-In
    • Applied Biological Chemistry
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    • v.48 no.3
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    • pp.263-266
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    • 2005
  • Cymbidium goeringii REICHB. fil was extracted with 80% MeOH and solvent-fractionated with EtOAc, n-BuOH and $H_2O$, successively. From EtOAc fraction, three sterols were isolated on repeated silica gel and ODS column chromatographies. The chemical structures were determined as ${\beta}-sitosterol$ (1), daucosterol (2) and ergosterol peroxide (3) by NMR, MS and IR, which is the first to be isolated from Cymbidium goeringii REICHB. fil.

Some Sesquiterpenoids and $5{\alpha},8{\alpha}-$Epidioxysterols from Solanum lyratum

  • Yu, Su-Mi;Kim, Hyoung-Ja;Woo, Eun-Rhan;Park, Ho-Koon
    • Archives of Pharmacal Research
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    • v.17 no.1
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    • pp.1-4
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    • 1994
  • From the stems of Solanum lyratum Thunb.(Solanaceae), two sesquiterpenoids together with two 5$\alpha$, 8$alpha-epidioxy sterols have been isolated and identified as atractylenolide I, dehydrocarissone, engosterol peroxide, 9, 11-dehydroergosterol peroxide. These compounds never previously isolated from this genus.

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Antitumor Sterol Isolated from the Fruiting Body of Pleurotus eryngii (Pleurotus eryngii 로부터 항암물질의 분리)

  • Lee Young-Hoon;Park Ki-Hun;Lee Byong-Won;Cho Yong-Un;Choi Young-Ju;Gal Sang-Wan
    • Journal of Life Science
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    • v.16 no.2 s.75
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    • pp.282-288
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    • 2006
  • Activity-guided fractionations led to the isolation of antitumor compound, ergosterol peroxide ($5{\alpha},\;8{\alpha}-epideoxy-24(R)-methylcholesta-6,\;22-dien-3{\beta}-ol$) from the fruiting body of Pleuratus eryngii that was cultivated artificially. This sterol structure was established by using spectroscopic methods ($^1H\;and\;^{13}C$ nuclear magnetic resonance and high resolution mass spectra). The purified compound showed a molecular formular of $C_{28}H_{44}O_3$ displaying characteristic features of epidioxy sterols. The 50% inhibitory concentrations ($IC_{50}$) of ergosterol peroxide against human lung cancer cell line (A549) and human ovarian cell line (SK-OV3) were $7{\mu}M\;and\;14{\mu}M$, respectively. In the DNA fragmentation assay, the compound showed the programmed cell death causing the chromosomal DNA fragmentation. It reveals that ergosterol peroxide arrests G1 phase of the cell division cycle.

Induction of Lipin1 by ROS-Dependent SREBP-2 Activation

  • Seo, Kyuhwa;Shin, Sang Mi
    • Toxicological Research
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    • v.33 no.3
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    • pp.219-224
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    • 2017
  • Lipin1 was identified as a phosphatidate phosphatase enzyme, and it plays a key role in lipid metabolism. Since free radicals contribute to metabolic diseases in the liver, this study investigated the effects of free radicals on the regulation of Lipin1 expression in Huh7 and AML12 cells. Hydrogen peroxide induced mRNA and protein expression of Lipin1 in Huh7 cells, which was assayed by quantitative RT-PCR and immunoblotting, respectively. Induction of Lipin1 by hydrogen peroxide was confirmed in AML12 cells. Hydrogen peroxide treatment significantly increased expression of sterol regulatory element-binding protein (SREBP)-2, but not SREBP-1. Moreover, nuclear translocation of SREBP-2 was detected after hydrogen peroxide treatment. Hydrogen peroxide-induced Lipin1 or SREBP-2 expression was significantly reduced by N-acetyl-$\small{L}$-cysteine treatment, indicating that reactive oxygen species (ROS) were implicated in Lipin1 expression. Next, we investigated whether the hypoxic environments that cause endogenous ROS production in mitochondria in metabolic diseases affect the expression of Lipin1. Exposure to hypoxia also increased Lipin1 expression. In contrast, pretreatment with antioxidants attenuated hypoxia-induced Lipin1 expression. Collectively, our results show that ROS activate SREBP-2, which induces Lipin1 expression.

Ergosterol peroxides from the fruit body of Sparassis crispa (꽃송이버섯(Sparassis crispa) 자실체로부터 ergosteol peroxide의 분리 및 동정)

  • Lee, Yeong-Geun;Thi, Nhan Nguyen;Kim, Hyoung-Geun;Lee, Dae Young;Lee, Seung-Eun;Kim, Geum-Soog;Baek, Nam-In
    • Journal of Applied Biological Chemistry
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    • v.59 no.4
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    • pp.313-316
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    • 2016
  • Sparassis crispa fruits were extracted in 80 % MeOH, and the concentrated extract was partitioned into EtOAc, n-butyl alcohol, and water fractions. The repeated octadecyl $SiO_2$ and silica gel ($SiO_2$) column chromatographies for the EtOAc and nbutyl alcohol fractions led to isolation of two ergosterol peroxides. There chemical structures were determined as ($3{\beta}$,$5{\alpha}$,$8{\alpha}$,22E)-5,8-Epidioxyergosta-6,22-dien-3-ol (ergosterol peroxide) (1) and 3-O-${\beta}$-D-glucopyranosyl ergosterol peroxide (2) based on spectroscopic data analyses including nuclear magnetic resonance, infrared spectrometry, and mass spectrometry (MS). Compounds 1 and 2 were for the first time isolated from S. crispa in this study.

Steroids and Triterpenoid from the Fruit Bodies of Ganoderma lucidum and Their Cytotoxic Activity

  • Lee, Joon-Seok;Lee, Mi-Kyoung;Hung, Tran-Manh;Lee, Ik-Soo;Min, Byung-Sun;Bae, Ki-Hwan
    • Natural Product Sciences
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    • v.15 no.3
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    • pp.173-179
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    • 2009
  • To determine the cytotoxic activity of natural compounds, chromatographic separation of the hexanesoluble fraction from the fruiting body of Ganoderma lucidum led to the isolation of four steroids and one triterpenoid. They were identified as ergosterol peroxide (1), stella sterol (2), ergosterol (3), 9(11)-dehydroergostrol peroxide (4), and ganodermanontriol (5) based on spectroscopic evidence and physicochemical properties. These compounds were examined for their cytotoxic activity against HL-60, MCF-7, and LLC cancer cell lines. Ganodermanontriol (5) showed cytotoxic activity with IC$_{50}$ values of 24.8 and 22.9 $\mu$g/mL against HL-60 and MCF-7 cancer cell lines, respectively, whereas compounds 1 - 4 were inactive.

Phytochemical Studies on Lonicera Caulis (1) - Sterols and Triterpenoids (인동의 성분연구 (1) - Sterol 및 Triterpenoid 화합물)

  • Kim, Ju-Sun;Yean, Min-Hye;Lee, So-Young;Lee, Je-Hyun;Kang, Sam-Sik
    • Korean Journal of Pharmacognosy
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    • v.40 no.4
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    • pp.319-325
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    • 2009
  • Twelve compounds were isolated from the 70% ethanol extract of Lonicera Caulis (Caprifoliaceae) and their structures were identified as six triterpenoids [(24S)-cycloart-25-en-$3{\beta}$,24-diol (1), pomolic acid (7), ursolic acid (8), euscaphic acid (9), hederagenin (10), and 23-hydroxytormentic acid (12)] and six sterols [obtusifoliol (2), gramisterol (3), citrostadienol (4), ${\beta}$-sitosterol (5), ergosterol peroxide (6) and ${\beta}$-sitosterol glucoside (11)]. The chemical structures of these compounds were identified on the basis of spectroscopic methods and comparison with literature values. All the compounds were isolated from this plant parts for the first time.

Ergosterol Peroxide from Flowers of Erigeron annuus L.as an Anti-Atherosclerosis Agent

  • Kim, Dong-Hyun;Jung, Sung-Je;Chung, In-Sik;Lee, Youn-Hyung;Kim, Dae-Keun;Kim, Sung-Hoon;Kwon, Byoung-Mog;Jeong, Tae-Sook;Park, Mi-Hyun;Seoung, Nak-Sul;Baek, Nam-In
    • Archives of Pharmacal Research
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    • v.28 no.5
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    • pp.541-545
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    • 2005
  • Flowers of Erigeron annuus L. were extracted with 80% aqueous MeOH, and the concentrated extract was partitioned with EtOAc, n-BuOH, and H$_2$O. Repeated silica gel and OD S column chromatography of the EtOAc fraction led to the isolation of a sterol, through activityguided fractionation, using ACAT inhibitory activity measurements. From the physico-chemical data, including NMR, MS, and IR, the chemical structure of the compound was determined to be an ergosterol peroxide (1), which has been isolated for the first time from this plant. This compound exhibited hACAT-1 and Lp-PLA$_2$ inhibitory effects, with inhibitory values of 51.6 ${\pm}$ 0.9 and 51 .7 ${\pm}$ 1.2%, at a treatment concentration of 0.23 mM.

Antioxidative compounds of Achillea sibirica Ledeb (톱풀의 항산화 성분)

  • Moon, Hyung-In;Lyu, Sung-Hyo;Roh, Jong-Hwa;Zee, Ok-Pyo
    • Korean Journal of Medicinal Crop Science
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    • v.8 no.1
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    • pp.1-8
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    • 2000
  • Achillea sibirica Ledeb. is widely distributed in Korea and has been often used as folk medicine in peptic and tonic. As one of our searches for bioactive (anti oxidation) compounds from medicinal plants, we studied Achillea sibirica Ledeb. (Compositae). Antioxidant activity of Achillea sibirica was determined by measuring lipid peroxide produced when a mouse liver homogenate was exposed at $90^{\circ}C$ using 2-thiobarbituric acid (TBA) and by evaluation the radical scavenging activity on 1, 1-diphenyl-2-picrylhydrazyl (DPPH) radical. Whole parts of Achillea sibirica was extracted with methanol and its extracts was fractionated with organic solvent; n-Hexane, methylene chloride, ethyl acetate, n-Butanol. EtOAc fraction exhibited antioxidant activity and From its, two flavonoid glycosides were isolated by silica gel and gel filtration colume chromatography and identified to kampferol 3-O-glucoside and luteolin 7-O-neo-hesperidoside, respectively, by physico-chemical and spectroscopical method. At antioxidant activity test for two compounds isolated, antioxidant activity was showed too. And from hexane fraction sterol was is isolated and identificated to mixture of campesterol, stigmasterol, and ${\beta}-sitosterol$.

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