• Title, Summary, Keyword: Hispidin

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Peroxidase-mediated Formation of the Fungal Polyphenol 3,14'-Bihispidinyl

  • Lee, In-Kyoung;Yun, Bong-Sik
    • Journal of Microbiology and Biotechnology
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    • v.18 no.1
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    • pp.107-109
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    • 2008
  • Medicinal fungi, Phellinus linteus and Inonotus xeranticus, produce a cluster of yellow pigment in their fermentation broth that acts as an important element of biological activity. The pigment is composed of diverse polyphenols with a styrylpyrone moiety, mainly hispidin and its dimers, 3,14'-bihispidinyl, hypholomine B, and 1,1-distyrylpyrylethan. Although dimeric hispidins were proposed to be biosynthesized from two molecules of monomer via oxidative coupling by ligninolytic enzymes, laccase and peroxidase, the details of this process remain unknown. In this preliminary study, we attempted to achieve enzymatic synthesis of the hispidin dimer from hispidin by using commercially available horseradish peroxidase (HRP). Consequently, a hispidin dimer, 3,14'-bihispidinyl, was synthesized, whereas the other dimers, hypholomine B and 1,1-distyrylpyrylethan, were not produced. This result suggested that the oxidative coupling at the C-3 and C-14' positions of hispidins was dominant in the process of dimerization by HRP, and indicated that additional catalysts or substrates would be needed to synthesize other hispidin dimers present in the fungal metabolite.

An Antioxidant Hispidin from the Mycelial Cultures of Phellinus linteus

  • Park, In-Hye;Chung, Shin-Kyo;Lee, Kyung-Bok;Yoo, Yung-Choon;Kim, Suk-Kyung;Kim, Geum-Soog;Song, Kyung-Sik
    • Archives of Pharmacal Research
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    • v.27 no.6
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    • pp.615-618
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    • 2004
  • In the course of screening for reactive oxygen species scavengers from natural products, an antioxidant was isolated from the mycelial culture broth of Phellinus linteus and identified as hispidin. The hispidin content was reached its maximum level at 12 days after onset of inoculation. About 2.5 mg/mL of hispidin was produced by P linteus in a yeast-malt medium (pH 5.8, $25^{\circ}C$). Hispidin inhibited 22.6 and 56.8% of the super oxide anion radical, 79.4 and 95.3% of the hydroxyl radical, and 28.1 and 85.5% of the DPPH radical at 0.1 and 1.0 mM, respectively. The positive control ${\alpha}-tocopherol$ scavenged 25.6 and 60.3%, 74.6 and 96.3%, and 32.7 and 77.5% of each radical, respectively, at the same concentrations. However, hispidin showed no significant activity on the hydrogen peroxide radical.

β-Secretase (BACE1) Purification by Refolding Method and Complex with Hispidin

  • Lim, Ji-Hong;Lee, Bo Ram;Park, Hee Won;Hong, Bum Soo;Lim, Beong Ou;Kim, Young Jun
    • Journal of the Korean Chemical Society
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    • v.58 no.6
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    • pp.553-559
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    • 2014
  • Alzheimer's disease (AD) is a devastating neurodegenerative disease that represents the most common form of dementia among the elderly population. The deposition of aggregated ${\beta}$-amyloid ($A{\beta}$) senile plaques in the human brain is a classic observation in the neuropathology of AD, yet an understanding of the mechanism of their formation remains elusive. $A{\beta}$ is formed through endoproteolysis of the amyloid precursor protein (APP) by ${\beta}$-secretase (BACE1, ${\beta}$-site APP-cleaving enzyme) and ${\gamma}$-secretase. In this study, BACE1 protein was successfully over-expressed, purified, and refolded and utilized in a binding study with hispidin. We developed a simpler refolding method using a urea gradient and size-exclusion gel filtration to purify an active BACE1 protein variant, in larger quantities than that reported previously, and measured the binding affinity of hispidin to the BACE1 protein variant through isothermal titration calorimetry.

Neuraminidase Inhibitors from the Culture Broth of Phellinus linteus

  • Yeom, Ji-Hee;Lee, In-Kyoung;Ki, Dae-Won;Lee, Myeong-Seok;Seok, Soon-Ja;Yun, Bong-Sik
    • Mycobiology
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    • v.40 no.2
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    • pp.142-144
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    • 2012
  • During the search for neuraminidase inhibitors from medicinal fungi, we found that the culture broth of Phellinus linteus exhibited potent inhibitory activity. Solvent partition, Sephadex LH-20 column chromatography, and high-performance liquid chromatography (HPLC) were performed for purification of two active substances from the culture broth. According to $^1H$ NMR measurements and comparison of HPLC retention times with those of authentic compounds, their chemical structures were identified as hispidin and hypholomine B. Compounds (hispidin) 1 and 2 (hypholomine B) inhibited neuraminidase, with $IC_{50}$ values of 13.1 and 0.03 ${\mu}M$, 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.

Chemical identification and antioxidant activity of phenolic compounds extracted from the fruiting body of 'Hankyong Sanghwang', Phellinus linteus KACC 93057P (Phellinus linteus KACC 93057P, '한경상황버섯'인공재배 자실체 페놀추출물의 항산화 활성 및 화학적 동정)

  • Min, Gyong-Jin;Jeong, Ee-un;Yun, Bong-Sik;Kang, Hee-Wan
    • Journal of Mushroom
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    • v.16 no.4
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    • pp.311-317
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    • 2018
  • The aim of this study was to identify chemical composition and antioxidant activity of phenolic extract of fruiting bodies of an artificially cultivated Hankyong Sanghwang mushroom, Phellinus linteus KACC 93057P (PLHS). The total phenolic content of 60% ethanolic extract of fruiting bodies of two-year-old PLHS grown on Oak wood logs was $19.05{\pm}0.32mg$ gallic acid equivalent (GAE)/g, which was 4-10 times high compared to the other species of mushrooms. 2,2-diphenyl-1-picrylhydrazyl (DPPH) and 2,2'-azino-bis(3-ethylbisthiazoline-6-sulfonic acid) (ABTS) radical scavenging activities and the ferric reducing antioxidant power (FRAP) value of PLHS were 2-10 and 5 times higher, respectively, than those of the other species of mushrooms. High performance liquid chromatography (HPLC) analysis of ethyl acetate fraction of 70% methanolic extract of the fruiting bodies of PLHS revealed the presence of styrylpyrone-class compounds, davallialactone, hispidin, hypholomine B, and caffeic acid, a compound of the phenylpropanoid pathway.

Comparison of antioxidant activities and polyphenolic compounds of extracts from artificially cultivated Sanghwang mushroom species, Phellinus linteus and P. baumii (인공재배 상황버섯 재배종 Phellinus linteus 와 P. baumii 자실체 추출물의 항산화활성과 폴리페놀 성분 비교)

  • Min, Gyeong-jin;Yun, Bong-Sik;Kang, Hee-Wan
    • Journal of Mushroom
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    • v.18 no.1
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    • pp.29-36
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    • 2020
  • P. linteus (Korea Sanghwang, PLKS) and P. baumii (Jangsoo Sangwhang, PBJS) were artificially cultivated under the same conditions. Fruiting bodies were extracted using 70% methanol, 60% ethanol, and hot water. Phenol and flavonoid contents were optimally extracted using 60% ethanol. Antioxidant activities of 60% ethanol extracts from fruiting bodies and mycelia from each Sanghwang mushroom species were measured using DPPH (2,2-diphenyl-1-picrylhydrazyl), ABTS (2,2'-azino-bis (3-ethylbisthiazoline-6-sulfonic acid) radical scavenging activities, and FRAP (ferric reducing antioxidant power). The antioxidant activities of fruiting bodies were relatively higher in comparison to those of mycelial samples. In high performance liquid chromatography (HPLC) analysis, styrylpyrone-class poly phenolic compounds, davallialactone, hispidin, hypholomine B, and inoscavin A were detected in fruiting body samples of two Sanghwang mushroom species, but not in their mycelial samples.

Hispidin from the Mycelial Cultures of Phellinus linteus Inhibits A $\beta$-Secreatase(BACE1) and proyl endopeptidase

  • Park, In-Hye;Kim, Sang-In;Jeon, So-Young;Lee, Hee-Ju;Song, Kyung-Sik
    • Proceedings of the PSK Conference
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    • pp.271.2-271
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    • 2003
  • The ${\gamma}$- and ${\beta}$-secretase are one of the most important proteases, which cleave amyloid precursor protein (APP) into neurotoxic A${\beta}$ peptide in Azheimer's type dementia. In the course of screening for anti-dementia agents from natural products, the mycelial culture of mushroom Phellinus linteus showed potent inhibition againt ${\beta}$-secretase (BACE1). (omitted)

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An Antioxidant Davallialactone from Phellinus baumii Enhances Sperm Penetration on In Vitro Fertilization of Pigs

  • Yi, Young-Joo;Lee, In-Kyoung;Lee, Sang-Myeong;Yun, Bong-Sik
    • Mycobiology
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    • v.44 no.1
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    • pp.54-57
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    • 2016
  • Davallialactone (DAVA) is a hispidin analogue derived from the medicinal fungus Phellinus baumii. We examined the effect of DAVA on in vitro fertilization (IVF) of pigs. Boar spermatozoa were incubated in fertilization medium with varying concentrations of DAVA, then sperm motility and reactive oxygen species (ROS) level were evaluated. Higher sperm motility was found following the addition of 0.5 or $1{\mu}M$ DAVA after incubation than addition of other concentrations or controls. ROS level decreased significantly with the addition of DAVA. The rate of normal fertilization was higher in the presence of $1{\mu}M$ DAVA (65.1%) than were those of other concentrations or controls (45.4~59.4%), and the highest total fertilization rate (mono- and polyspermic oocytes) was observed at $1{\mu}M$ DAVA (83%). In conclusion, addition of DAVA to fertilization medium improved sperm motility, and reduced ROS level so as to potentially improve sperm-oocyte binding in IVF, suggesting the potential of a compound isolated from mushrooms in assisted reproductive technology for humans and animals.

진흙버섯의 항인플루엔자 활성 및 활성성분 규명

  • Hwang, Byung Soon;Yun, Bong-Sik
    • 한국균학회소식:학술대회논문집
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    • pp.41-41
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    • 2016
  • Influenza viruses are RNA viruses that belong to the Orthomyxoviridae family, and those can be divided into three types; A, B, and C, which based on the differences of the inner nucleoproteins and genomic structures. All three genera differ in their genomic structure and nucleoprotein content, they are further classified into various serotypes based on the two surface glycoproteins, hemagglutinin (HA) and neuraminidase (NA). These glycoproteins play crucial roles in viral infection and replication. Hemagglutinin mediates binding of virions to sialic acid receptors on the surfaces of target cells at the initial stage of infection. Neuraminidase cleaves the glycosidic bonds of sialic acids from the viral and cell surfaces to release the mature virions from infected cells, after viral replication. Because NA plays an important role in the viral life cycle, it is considered an attractive therapeutic target for the treatment of influenza. The methanolic extracts of Phellinus baumii and Phellinus igniarius exhibited significant activity in the neuraminidase inhibition assay. Polyphenolic compounds were isolated from the methanolic extracts. The structures of these compounds were determined to be hispidin, hypholomine B, inoscavin A, davallialactone, phelligridin D, phelligridin E, and phelligridin G by spectroscopic methods. Compounds inhibited the H1N1 neuraminidase activity in a dose-dependent manner with $IC_{50}$ values of 50.9, 22.9, 20.0, 14.2, 8.8, 8.1 and $8.0{\mu}M$, respectively. Moreover, these compounds showed anti-influenza activity in the viral cytopathic effect (CPE) reduction assay using MDCK cells. These results suggests that the polyphenols from P. baumii and P. igniarius are promising candidates for prevention and therapeutic strategies against viral infection.

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