Anti-hepatitis C Virus Natural Product from a Fungus, <i>Penicillium herquei</i>

Nishikori, Shu; Takemoto, Kenji; Kamisuki, Shinji; Nakajima, Shingo; Kuramochi, Kouji; Tsukuda, Senko; Iwamoto, Masashi; Katayama, Yoshikazu; Suzuki, Takahiro; Kobayashi, Susumu; Watashi, Koichi; Sugawara, Fumio

doi:10.1021/acs.jnatprod.5b00555

Cited by 35 publications

(13 citation statements)

References 28 publications

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“…Herqueorum produce atrovenetin, herqueinone, herqueichrysin, peniciherqueinone, peniciphenalines, sclerodin, scleroderolide, sclerodione, sculenonone A & B, and xanthoherquein ( Stodola et al., 1951 , Galarraga et al., 1955 , Harman et al., 1955 , Barton et al., 1959 , Narasimhachari et al., 1963 , Narasimhachari and Vining, 1963 , Narasimhachari and Ramaswami, 1966 , Narasimhachari and Vining, 1972 , Simpson, 1976 , Robinson et al., 1992 , Trotter, 1992 , Tansakul et al., 2014 , Nishikori et al., 2016 , Li et al., 2018a ), herqulines ( Furusaki et al., 1980 , Enomoto et al., 1996 , Chiba et al., 2017 , Yang et al., 2018 ), neocyclocitrinol ( Marinho et al. 2009 ), peniciherquamides ( Nishikori et al. 2016 ), hualyzin ( Ding et al.…”

Section: Resultsmentioning

confidence: 99%

Classification of Aspergillus, Penicillium, Talaromyces and related genera (Eurotiales): An overview of families, genera, subgenera, sections, series and species

Houbraken¹,

Kocsubé²,

Visagie³

et al. 2020

Studies in Mycology

373

458

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The Eurotiales is a relatively large order of Ascomycetes with members frequently having positive and negative impact on human activities. Species within this order gain attention from various research fields such as food, indoor and medical mycology and biotechnology. In this article we give an overview of families and genera present in the Eurotiales and introduce an updated subgeneric, sectional and series classification for Aspergillus and Penicillium . Finally, a comprehensive list of accepted species in the Eurotiales is given. The classification of the Eurotiales at family and genus level is traditionally based on phenotypic characters, and this classification has since been challenged using sequence-based approaches. Here, we re-evaluated the relationships between families and genera of the Eurotiales using a nine-gene sequence dataset. Based on this analysis, the new family Penicillaginaceae is introduced and four known families are accepted: Aspergillaceae , Elaphomycetaceae , Thermoascaceae and Trichocomaceae . The Eurotiales includes 28 genera: 15 genera are accommodated in the Aspergillaceae ( Aspergillago , Aspergillus , Evansstolkia , Hamigera , Leiothecium , Monascus , Penicilliopsis , Penicillium , Phialomyces , Pseudohamigera , Pseudopenicillium , Sclerocleista , Warcupiella , Xerochrysium and Xeromyces ), eight in the Trichocomaceae ( Acidotalaromyces , Ascospirella , Dendrosphaera , Rasamsonia , Sagenomella , Talaromyces , Thermomyces , Trichocoma ), two in the Thermoascaceae ( Paecilomyces , Thermoascus ) and one in the Penicillaginaceae ( Penicillago ). The classification of the Elaphomycetaceae was not part of this study, but according to literature two genera are present in this family ( Elaphomyces and Pseudotulostoma ). The use of an infrageneric classification system has a long tradition in Aspergillus and Penicillium . Most recent taxonomic studies focused on the sectional l...

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Section: Resultsmentioning

confidence: 99%

Classification of Aspergillus, Penicillium, Talaromyces and related genera (Eurotiales): An overview of families, genera, subgenera, sections, series and species

Houbraken¹,

Kocsubé²,

Visagie³

et al. 2020

Studies in Mycology

373

458

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“…Natural products were extracted essentially as described 44 . Culture broths of fungal strains isolated from seaweeds, mosses, and other plants were extracted with CH 2 Cl 2 .…”

Section: Methodsmentioning

confidence: 99%

TRPA1-dependent reversible opening of tight junction by natural compounds with an α,β-unsaturated moiety and capsaicin

Kanda

Yamasaki

Sasaki-Yamaguchi

et al. 2018

Sci Rep

Self Cite

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The delivery of hydrophilic macromolecules runs into difficulties such as penetration of the cell membrane lipid bilayer. Our prior experiment demonstrated that capsaicin induces the reversible opening of tight junctions (TJs) and enhances the delivery of hydrophilic macromolecules through a paracellular route. Herein, we screened paracellular permeability enhancers other than capsaicin. As TJ opening by capsaicin is associated with Ca2+ influx, we first screened the compounds that induce Ca2+ influx in layered MDCK II cells, and then we determined the compounds’ abilities to open TJs. Our results identified several natural compounds with α,β-unsaturated moiety. A structure-activity relationship (SAR) analysis and the results of pretreatment with reducing reagent DTT suggested the importance of α,β-unsaturated moiety. We also examined the underlying mechanisms, and our findings suggest that the actin reorganization seen in capsaicin treatment is important for the reversibility of TJ opening. Furthermore, our analyses revealed that TRPA1 is involved in the Ca2+ influx and TJ permeability increase not only by an α,β-unsaturated compound but also by capsaicin. Our results indicate that the α,β-unsaturated moiety can be a potent pharmacophore for TJ opening.

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“…Because of the importance of this genus, chemical assessments on more and more Penicillium species have been investigated from different environmental sources. The endophytic fungi (Arunpanichlert et al 2010; Zhu et al 2015) and soil fungi (Tansakul et al 2014; Daengrot et al 2015) were the most studied fungi in this genus and a number of natural products have been reported to exhibit diverse activities including anti-inflammatory, cytotoxic (Xue et al 2014), or anti-hepatitis C virus (Kozlovskii et al 2013; Nishikori et al 2016). Other strains from extreme conditions also raised the great interest to mine novel structures, such as halotolerant or extremophilic strains (Lu et al 2008; Stierle et al 2012)，deep sea-derived strains (Li et al 2013), and marine animal-derived strains (Qi et al 2013).…”

Section: Introductionmentioning

confidence: 99%

Chemical diversity from the Tibetan Plateau fungi Penicillium kongii and P. brasilianum

Liu

et al. 2017

Mycology

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Two new secondary metabolites, kongiilines A and B (1, 7), and two asperphenamate derivatives, asperphenamates B and C (5–6), together with 16 known compounds (2–4, 8–20), were isolated from Tibetan Plateau fungi Penicillium kongii and Penicillium brasilianum. This is the first report on asperphenamates B and C as naturally occurring compounds, and that aspterric acid is isolated from P. brasilianum for the first time. Their structures were elucidated by different spectroscopic techniques including high-resolution electrospray ionisation mass spectrum, 1D nuclear magnetic resonance (NMR), and 2D NMR as well as electronic circular dichroism. Compounds 4, 5, and 10 exhibited cytotoxicity activities against human colon carcinoma HCT116 cell line with IC50 values of 88.16, 77.68, and 36.92 μM, respectively. Fungi from Tibetan Plateau represent important and rich resources for the investigation of new chemicals.

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Anti-hepatitis C Virus Natural Product from a Fungus, Penicillium herquei

Cited by 35 publications

References 28 publications

Classification of Aspergillus, Penicillium, Talaromyces and related genera (Eurotiales): An overview of families, genera, subgenera, sections, series and species

Classification of Aspergillus, Penicillium, Talaromyces and related genera (Eurotiales): An overview of families, genera, subgenera, sections, series and species

TRPA1-dependent reversible opening of tight junction by natural compounds with an α,β-unsaturated moiety and capsaicin

Chemical diversity from the Tibetan Plateau fungi Penicillium kongii and P. brasilianum

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