• 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.

• 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.

• Mycobiology
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• v.47 no.2
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• pp.242-249
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• 2019

Betaine derivatives are considered major ingredients of shampoos and are commonly used as antistatic and viscosity-increasing agents. Several studies have also suggested that betaine derivatives can be used as antimicrobial agents. However, the antifungal activity and mechanism of action of betaine derivatives have not yet been fully understood. In this study, we investigated the antifungal activity of six betaine derivatives against Malassezia restricta, which is the most frequently isolated fungus from the human skin and is implicated in the development of dandruff. We found that, among the six betaine derivatives, lauryl betaine showed the most potent antifungal activity. The mechanism of action of lauryl betaine was studied mainly using another phylogenetically close model fungal organism, Cryptococcus neoformans, because of a lack of available genetic manipulation and functional genomics tools for M. restricta. Our genome-wide reverse genetic screening method using the C. neoformans gene deletion mutant library showed that the mutants with mutations in genes for cell membrane synthesis and integrity, particularly ergosterol synthesis, are highly sensitive to lauryl betaine. Furthermore, transcriptome changes in both C. neoformans and M. restricta cells grown in the presence of lauryl betaine were analyzed and the results indicated that the compound mainly affected cell membrane synthesis, particularly ergosterol synthesis. Overall, our data demonstrated that lauryl betaine influences ergosterol synthesis in C. neoformans and that the compound exerts a similar mechanism of action on M. restricta.

• Natural Product Sciences
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• v.20 no.2
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• pp.76-79
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• 2014

In our ongoing search for structurally interesting and biologically active metabolites from Korean wild mushrooms, bioassay-guided fractionation and a chemical investigation of the MeOH extracts of the fruiting bodies of the mushroom Naematoloma fasciculare resulted in the isolation of three ergosterol derivatives, (22E,24R)-ergosta-7,22-diene-$3{\beta}$,$5{\alpha}$,$6{\beta}$,$9{\alpha}$-tetrol (1), (22E,24R)-$5{\alpha}$,$8{\alpha}$-epidioxyergosta-6,22-diene-$3{\beta}$-ol 3-O-${\beta}$-$\small{D}$-glucopyranoside (2), and (22E,24R)-$5{\alpha}$,$8{\alpha}$-epidioxyergosta-6,9,22-triene-$3{\beta}$-ol 3-O-${\beta}$-$\small{D}$-glucopyranoside (3). The structures of 1 - 3 were determined by comparison of their spectroscopic and physical data with reported values. The isolated steroid derivatives 1 and 3 were reported for the first time from this mushroom. Compounds 1 - 3 were tested for their cytotoxic activities against four human cancer cell lines (A549, SK-OV-3, SK-MEL-2, and HCT-15).

• 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.

• Bulletin of the Korean Chemical Society
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• v.34 no.5
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• pp.1339-1344
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• 2013

We have synthesized several glycosyl ergosterols and 5,6-dihydroergosterols (DHE) and examined their effects on production of nitric oxide (NO) and iNOS protein expression in LPS-treated RAW264.7 macrophage cells. Our results showed that DHE derivatives inhibited production of NO and iNOS protein expression more strongly than ergosterol derivative. Especially, DHE-Glc exhibited most potent inhibitory activity without cytotoxicity up to the concentration of $100{\mu}M$.

• 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.

• YAKHAK HOEJI
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• v.51 no.6
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• pp.430-434
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• 2007

The anti-inflammatory activity of fruit body of Phellinus pini was investigated by activity-guided fractionation. From the screening of each fraction for the inhibitory activity of NO production in lipopolysaccaride (LPS) activated RAW 264.7 cells, methanol extract and its hexane soluble fraction of Phellinus pini exhibited inhibition of NO production compared with LPS control without toxicity. The hexane soluble fraction showed dose-dependent inhibition of NO production. The active hexane fraction was repeatedly chromatographed over silica gel, ergosta-7,24(28)-dien-3-ol(1) and ergosterol peroxide (2) were isolated and identified. Ergosterol derivatives were inhibited NOS activation, $IC_{50}$ of them were $18.9{\pm}3.9{\mu}M$ (1) and $20.4{\pm}4.5{\mu}M$ (2).

• Applied Biological Chemistry
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• v.50 no.1
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• pp.57-62
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• 2007

The fruiting body of Phellinus linteus was extracted with 80% aqueous MeOH, and the concentrated extract was partitioned with EtOAc, n-BuOH and $H_2$O. The repeated silica gel and ODS column chromatographies of the EtOAc fraction led to isolation of four sterols. From the result of spectral data including NMR, MS and IR, the chemical structures of the sterols were determined as ergosta-7,24(28)-dien-3${\beta}$-ol (episterol, 1), 5${\alpha}$,8${\alpha}$-epidioxyergosta-6,9(11),22-trien-3${\beta}$-ol (dehydrop-eroxyergosterol, 2), 5${\alpha}$,8${\alpha}$-epidioxyergosta-6,22-dien-3${\beta}$-ol (ergoterol peroxide, 3), and $3{\beta}$,$5{\alpha}$-dihydroxy-6${\beta}$-methoxyergosta-7,22-diene (6-O-methylcerevisterol, 4). The ergosterols have been first isolated from this mushroom in this study.

• 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.