• Title/Summary/Keyword: ergosta-4, 6, 8 (14)

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Chemical Constituents of the Sclerotia of Grifola umbellata (저령(Grifola umbellata)균핵의 추출성분)

  • 이학주;이경태;박영기;이민웅
    • Journal of Korea Foresty Energy
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    • v.21 no.1
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    • pp.16-24
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    • 2002
  • Three alkaloids and two steroids were isolated from the sclerotia of Grifola umbellata. Structures of the isolated compounds were determined as 9-$\beta$-D-ribofuranosyladenine (adenosine), 1-$\beta$-D-ribofuranosyluracil (uridine), 2,4-pyrimidinedione (uracil), ergosta-4, 6, 8 (14), 22-tetraen-3-one and ergosta-5, 7, 22-tritene-$3\beta$-ol (ergosterol) respectively on the basis of spectroscopic data and chemical correlations.

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Chemical Constituents from the Fruit Bodies of Tricholoma matsutake (송이(Tricholoma matsutake) 자실체의 화학성분)

  • Lee, Hak-Ju;Choi, Yun-Jeong;Ka, Kang-Hyeon;Bak, Won-Chul
    • Journal of the Korean Wood Science and Technology
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    • v.31 no.4
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    • pp.63-70
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    • 2003
  • One alkaloid derivatives, one amide and two steroids were isolated from the fruit bodies of Tricholoma matsutake. The structures were determinded as adenosine, methyl trans-cinnamate, ergosterol and ergosta-4, 6, 8 (14), 22-tetraen-3-one, respectively, on the basis of spectroscopic data.

Cytotoxic Ergosterols from Paecilomyces sp. J300

  • Kwon, Hak-Cheol;Zee, Sang-Deuk;Cho, Sae-Yun;Choi, Sang-Un;Lee, Kang-Ro
    • Archives of Pharmacal Research
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    • v.25 no.6
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    • pp.851-855
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    • 2002
  • Seven ergosterol derivatives (1-7) were isolated from silkworm larvae infected with Paecilomyces sp. J300. On the basis of spectroscopic means, their structures have been elucidated as 3$\beta$,5$\alpha$-dihydroxy-ergosta-7,22-diene (1), 5$\alpha$,6$\alpha$-epoxy-(22E,24R)-ergosta-8(14), 22-diene-3$\beta$,7$\alpha$-diol (2), 5$\alpha$,6$\alpha$-epoxy-(22E,24R)-ergosta-8, 22-diene-3$\beta$,7$\alpha$-diol (3), ergosta-4, 6, 8(14), 22-tetraene-3-one (4), ergosterol (5), ergosterol endoperoxide (6), 3$\beta$,5$\alpha$-dihydroxy-6$\beta$-methoxyergosta-7,22-diene (7). Compounds 3~7 showed moderate cytotoxicity against five tumor cells.

Cytotoxicity of Ergosterol Derivatives from the Fruiting Bodies of Hygrophorus russula

  • Lee, Ik-Soo;Kim, Jin-Pyo;Na, Min-Kyun;Jung, Hyun-Ju;Min, Byung-Sun;Bae, Ki-Hwan
    • Natural Product Sciences
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    • v.17 no.2
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    • pp.85-89
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    • 2011
  • Bioassay-guided fractionation of the $CHCl_3$-soluble fraction of a MeOH extract of the fruiting bodies of Hygrophorus russula led to the isolation of five ergosterol derivatives (1 - 5). The structures of these compounds were identified as ergosterol peroxide (1), ergosta-4,6,8(14),22-tetraen-3-one (2), ergosta-7,22-diene-3${\beta}$,5${\alpha}$,6${\alpha}$-triol (3), ergosta-7,22-diene-3${\beta}$,5${\alpha}$,6${\beta}$,9${\alpha}$-tetraol (4), and 5${\alpha}$,6${\alpha}$-epoxy-ergosta-8(14),22-diene-3${\beta}$,7${\alpha}$-diol (5) by comparing their physicochemical and spectral data with those in the literature. These compounds were evaluated for in vitro cytotoxicity against A549 and XF498 cancer cell lines. Most of the tested compounds, except for compound 3, exhibited moderate cytotoxicity against both A549 and XF498 cell lines with $IC_{50}$ values ranging from 10.2 to 18.3 ${\mu}g/ml$ and from 11.4 to 24.6 ${\mu}g/ml$, respectively.

Chemical Constituents of Gymnopilus spectabilis and Their Antioxidant Activity

  • Lee, In-Kyoung;Cho, Sung-Min;Seok, Soon-Ja;Yun, Bong-Sik
    • Mycobiology
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    • v.36 no.1
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    • pp.55-59
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    • 2008
  • Gymnopilus spectabilis, a hallucinogenic mushroom belonging to the family Cortinariaceae, is found growing in dense clusters on stumps and logs of hardwoods and conifers. It contains the hallucinogenic alkaloid psilocybin and its strongly bitter taste makes it undesirable as an edible. In an effort to identify chemical constituents of Korean native wild mushrooms, 4,6-decadiyne-1,3,8-triol (1), ergosta-4,6,8(14), 22-tetraen-3-one (2), bisnoryangonin (3), and hispidin (4) were isolated from the methanolic extract of the fruiting bodies of G. spectabilis. Their structures were assigned on the basis of various spectroscopic studies. Compounds 3 and 4 displayed significant scavenging activity against the ABTS radical cation, DPPH radical, and superoxide radical anion, while 1 and 2 exhibited no antioxidant activity.

Inhibition of Nitric Oxide Synthesis by Ergosterol Derivative from Phellinus pini in LPS-Activated RAW 264.7 Cells (낙엽송층버섯으로부터 Ergosterol 유도체의 분리 및 RAW 264.7 세포주의 Nitric Oxide 생성 저해활성)

  • Jang, Hyun-Jin;Yang, Ki-Sook
    • YAKHAK HOEJI
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    • v.50 no.6
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    • pp.367-371
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    • 2006
  • Phellinus pini (Hymenocaetaceae) has been used for the immunomodulating activity hypolipidemic effect, gastric cancer non-insulin dependant diabetes, diarrhea, and menstrual irregularity. From the screening of each fraction for the inhibitory activity of NO production in lipopolysaccaride (LPS) activated RAW 264.7 cells, methanol extract of Phellinus pini and hexane soluble fraction exhibited inhibition of NO production compared with LPS control without toxicity. The hexane soluble fraction showed dose dependent inhibition of NO production. According to activity guided fractionation, the active hexane fr. was repeatedly chromatographed over silica gel, ergosta-4,6,8(14),22- tetraen-3-one was isolated. The compound inhibited NOS activation (IC$_{50}$ = 29.7 uM) and NO production of activated macrophage at 30 uM.

Inhibition of Nitric Oxide Production, iNOS and COX-2 Expression of Ergosterol Derivatives from Phellinus pini

  • Hong, Yun-Jung;Jang, A-Reum;Jang, Hyun-Jin;Yang, Ki-Sook
    • Natural Product Sciences
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    • v.18 no.3
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    • pp.147-152
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    • 2012
  • Ergosta-4,6,8(14),22-tetraen-3-one (1), ergosta-7,24(28)-dien-3-ol (2), and 5,8-epidioxyergosta-6,22-dien-3-ol(3) were isolated from the fruit body of Phellinus pini. Their structures were based on spectroscopic methods including IR, MS, and NMR (1D and 2D). These compounds were screened for their ability to inhibit nitric oxide (NO) production in LPS-activated RAW 264.7 cells. Compounds 1, 2, and 3 reduced NO production in the assay with $IC_50$ values of 29.7 ${\mu}M$ (1), 15.1 ${\mu}M$ (2), and 18.4 ${\mu}M$ (3) respectively. They also suppressed the expression of protein and m-RNA of iNOS and COX-2 in a dose dependent manner by western blot analysis and RT-PCR experiment in LPS-activated microglial cells.

Inhibition of Melanin Production and Tyrosinase Expression of Ergosterol Derivatives from Phellinus pini

  • Hong, Yun Jung;Jang, A Reum;Yang, Ki Sook
    • Natural Product Sciences
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    • v.19 no.3
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    • pp.258-262
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    • 2013
  • Three ergosterol derivatives, ergosta-4,6,8(14),22-tetraen-3-one (1), ergosta-7,24(28)-dien-3-ol (2), and 5,8-epidioxyergosta-6,22-dien-3-ol(3) were isolated from the fruit body of Phellinus pini. Their structures were based on spectroscopic methods including IR, MS, and NMR (1D and 2D). These compounds were evaluated for their activity to decrease melanin production in ${\alpha}$-MSH (melanocyte stimulating hormone) activated B16F10 cells. Compound 1, 2, and 3 reduced melanin content in a dose-dependent manner at concentrations of 5~15 uM. They also suppressed the tyrosinase expression of protein and m-RNA level dose dependently by western blot analysis and RT-PCR experiment in B16F10 murine melanoma cells.

Secondary Metabolites of Volvariella bombycina and Their Inhibitory Effects on Melanogenesis

  • Xu, Guang-Hua;Choo, Soo-Jin;Kim, Young-Hee;Ryoo, In-Ja;Seok, Soon-Ja;Ahn, Jong-Seog;Yoo, Ick-Dong
    • Journal of Microbiology and Biotechnology
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    • v.20 no.1
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    • pp.78-81
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    • 2010
  • Four compounds were isolated from the culture broth of Volvariella bombycina and they were identified as ergosta-4,6,8(14),22-tetraene-3-one (1), ergosterol peroxide (2), indole-3-carboxaldehyde (3), and indazole (4) by interpretation of spectroscopic data. Among them, compound 2 exhibited melanogenesis inhibitory effect in cultured B16 mouse melanoma cells.