• Title/Summary/Keyword: 4-(3, 4-dihydroxyphenyl)-3-buten-2-one

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Inhibition on LDL-oxidation by Phenolic Compounds from the Fruit Body of Phellinus linteus

  • Lyu, Ha-Na;Lee, Dae-Young;Lee, Min-Kyung;Cho, Moon-Hee;Jeong, Tae-Sook;Kim, In-Ho;Lee, Chang-Ho;Baek, Nam-In
    • Journal of Applied Biological Chemistry
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    • v.52 no.3
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    • pp.147-150
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    • 2009
  • The fruit body of Phellinus linteus was extracted with 80% aqueous MeOH, and the concentrated extract was successively partitioned using EtOAc, n-BuOH and $H_2O$. From the EtOAc and n-BuOH fractions, three phenolic compounds were isolated through repeated silica gel and ODS column chromatography. The chemical structures of these compounds were determined as 2-(3',4'-dihydroxyphenyl)-1,3-benzodioxole-5-aldehyde (1), 4-(3,4-dihydroxyphenyl)-3-buten-2-one (2), and protocatechuic acid methyl ester (3) by spectroscopic data including NMR, MS and IR. Compounds $1{\sim}3$ exhibited low density lipoprotein (LDL) antioxidant activity with $IC_{50}$ values of 1.7, 0.7, and $2.4{\mu}M$, respectively.

Neuraminidase Inhibitors from the Fermentation Broth of Phellinus linteus

  • Hwang, Byung Soon;Lee, Myeong-Seok;Lee, Seung Woong;Lee, In-Kyoung;Seo, Geon-Sik;Choi, Hwa Jung;Yun, Bong-Sik
    • Mycobiology
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    • v.42 no.2
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    • pp.189-192
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    • 2014
  • During a search for neuraminidase inhibitors derived from medicinal fungi, we found that the fermentation broth of Phellinus linteus exhibited potent neuraminidase inhibitory activity. Through bioassay-guided fractionation, two active compounds were purified from the ethyl acetate-soluble portion of the fermentation broth of P. linteus. These structures were identified as inotilone (1) and 4-(3,4-dihydroxyphenyl)-3-buten-2-one (2) by spectroscopic methods. Compounds 1 and 2 inhibited H1N1 neuraminidase activity with $IC_{50}$ values of 29.1 and 125.6 $125.6{\mu}M$, respectively, in a dose-dependent manner. They also exhibited an antiviral effect in a viral cytopathic effect reduction assay using MDCK cells. These results suggest that compounds 1 and 2 from the culture broth of P. linteus would be good candidates for the prevention and therapeutic strategies towards viral infections.

Protective Effect of 4-(3,4-Dihydroxyphenyl)-3-Buten-2-One from Phellinus linteus on Naproxen-Induced Gastric Antral Ulcers in Rats

  • Kim, Jeong-Hwan;Kwon, Hyun Ju;Kim, Byung Woo
    • Journal of Microbiology and Biotechnology
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    • v.26 no.5
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    • pp.823-828
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    • 2016
  • The present study investigated the protective effect of naturally purified 4-(3,4-dihydroxyphenyl)-3-buten-2-one (DHP) from Phellinus linteus against naproxen-induced gastric antral ulcers in rats. To verify the protective effect of DHP on naproxen-induced gastric antral ulcers, various doses (1, 5, and 10 μg/kg) of DHP were pretreated for 3 days, and then gastric damage was caused by 80 mg/kg naproxen applied for 3 days. DHP prevented naproxen-induced gastric antral ulcers in a dose-dependent manner. In particular, 10 μg/kg DHP showed the best protective effect against naproxen-induced gastric antral ulcers. Moreover, DHP significantly attenuated the naproxen-induced lipid peroxide level in gastric mucosa and increased the activities of radical scavenging enzymes, such as superoxide dismutase, catalase, and glutathione peroxidase, in a dose-dependent manner. A histological examination clearly demonstrated that the gastric antral ulcer induced by naproxen nearly disappeared after the pretreatment of DHP. These results suggest that DHP can inhibit naproxen-induced gastric antral ulcers through prevention of lipid peroxidation and activation of radical scavenging enzymes.

Phenolic Compounds from the Fruit Body of Phellinus linteus Increase Alkaline Phosphatase (ALP) Activity of Human Osteoblast-like Cells

  • Lyu, Ha-Na;Lee, Dae-Young;Kim, Dong-Hyun;Yoo, Jong-Su;Lee, Min-Kyung;Kim, In-Ho;Baek, Nam-In
    • Food Science and Biotechnology
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    • v.17 no.6
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    • pp.1214-1220
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    • 2008
  • Secondary metabolites from the fruit body of Phellinus linteus were evaluated for their proliferative effect on human osteoblast-like cells. 3-[4,5-Dimethylthiazole-2-y1]-2,5-diphenyl-tetraxolium bromide (MTT) assay and alkaline phosphatase (ALP) activity assay were used to assess the effect those isolates on the human osteoblast-like cell line (Saos-2). Activity-guided fractionation led to the isolation of ALP-activating phenolic compounds through the extraction of P. linteus, solvent partitioning, and repeated silica gel and octadecyl silica gel (ODS) column chromatographic separations. From the result of spectroscopic data including nuclear magnetic resonance (NMR), mass spectrometry (MS), and infrared spectroscopy (IR), the chemical structures of the compounds were determined as 4-(4-hydroxyphenyl)-3-buten-2-one(1), 2-(3',4'-dihydroxyphenyl)-1,3-benzodioxole-5-aldehyde (2), 4-(3,4-dihydroxyphenyl)-3-buten-2-one (3), 3,4-dihydroxybenzaldehyde (4), and protocatechuic acid methyl ester (5), respectively. This study reports the first isolation of compounds 1-3 and 5 from P. linteus. In addition, all phenolic compounds stimulated proliferation of the osteoblast-like cells and increased their ALP activity in a dose-dependent manner ($10^{-8}$ to $10^{-1}\;mg/mL$). The present data demonstrate that phenolic compounds in P. linteus stimulated mineralization in bone formation caused by osteoporosis. The bone-formation effect of P. linteus seems to be mediated, at least partly, by the stimulating effect of the phenolic compounds on the growth of osteoblasts.

Chemical Constituents of the Culture Broth of Phellinus linteus and Their Antioxidant Activity

  • Lee, Myeong-Seok;Hwang, Byung Soon;Lee, In-Kyoung;Seo, Geon-Sik;Yun, Bong-Sik
    • Mycobiology
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    • v.43 no.1
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    • pp.43-48
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    • 2015
  • The medicinal fungus Phellinus linteus, in the family Hymenochaetaceae, has been used as a traditional medicine for the treatment of various diseases. In this study, the chemical constituents of the culture broth of P. linteus were investigated. P. linteus was cultured in potato dextrose broth medium, and the culture broth was extracted with ethyl acetate. The ethyl acetate-soluble portion was concentrated and subjected to ODS column chromatography, followed by Sephadex LH-20 column chromatography. Six compounds (1~6) were purified by preparative reversed-phase high-performance liquid chromatography. Spectroscopic methods identified their structures as caffeic acid (1), inotilone (2), 4-(3,4-dihydroxyphenyl)-3-buten-2-one (3), phellilane H (4), (2E,4E)-(+)-4'-hydroxy-${\gamma}$-ionylideneacetic acid (5), and (2E,4E)-${\gamma}$-ionylideneacetic acid (6). Compounds 1, 2, and 3 exhibited potent dose-dependent antioxidant activity.

Antioxidative Activities of Phenolic Compounds Isolated from Inonotus obliquus (차가버섯으로부터 분리한 페놀성 화합물의 항산화효과)

  • Kim, Hyoung-Ja;Jin, Chang-Bae;Lee, Yong-Sup
    • Korean Journal of Pharmacognosy
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    • v.38 no.2 s.149
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    • pp.164-169
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    • 2007
  • ln our continued search for biologically active compounds from traditional medicine, we found that ethyl acetate fraction from Inonotus obliquus showed potent antioxidant activities on three different cell-free bioassay systems. Bioassay-directed chromatographic fractionation of the ethyl acetate fraction from Inonotus obliquus afforded four phenolic compounds, 4-(3,4-dihydroxyphenyl)-(E)-3-buten-2-one (1) , 3,4-dihydroxybenzaldehyde (2), protocatechuic acid (3) and caffeic acid (4) along with three sterols such as lanosterol (5), ergosterol peroxide (6) and 9,11-dehydroergosterol peroxide (7). Among isolates, phenolic compounds (1-4) were assessed for antioxidant activities. Almost phenolic compounds showed potent DPPH and superoxide anion radicals scavenging and lipid peroxidation inhibitory activities indicating that these phenolic compounds contribute to the antioxidative activities of I. obliquus. Compounds 2-3 and 7 were isolated for the first time from this plant.