Hirokazu Kawagishi

Hirokazu Kawagishi
Shizuoka University · Research Institute of Green Science and Technology

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327
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Introduction
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Publications

Publications (327)
Article
Five compounds including a new compound (1) were isolated from mycelia of a mushroom-forming fungus Agaricus blazei. Compound 2 was isolated from nature for the first time. Their structures were determined by the interpretation of spectroscopic data. In the bioassay examining growth inhibitory activity against phytopathogenic bacteria Clavibacter m...
Article
Fungi belonging to the Ascomycete genus Cordyceps are endoparasitoids and parasites, mainly of insects and other arthropods. Cordyceps militaris has been used as a therapeutic drug for cancer patients. However, the infection, parasitism, and fruiting body formation mechanisms of this fungus are still unknown. Based on our hypothesis that lectin(s)...
Article
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As a traditional Chinese medicine, Crocus sativus Linn has been used for a long time in China. However, the studies on secondary metabolites of its endophytic fungi were not fully sufficient. Thus, the endophytic fungus, Aspergillus fumigatus, collected from the lateral buds of C. sativus, was here investigated. An approach combining UHPLC-HRMS/MS...
Article
A novel compound (1) and three known compounds (2−4) were isolated from the fruiting bodies of Hypholoma fasciculare. The structure of 1 was determined by the interpretation of spectroscopic data. Compounds 2−4 were identified by comparing the spectra data of known compounds. In the bioassay examining growth inhibitory activity against phytopathoge...
Article
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Lepista sordida is a fairy ring-forming fungus that belongs to the family Tricholomataceae and is widely distributed in the Northern Hemisphere. Here, we report the complete mitochondrial genome sequence of L. sordida. The mitochondrial genome (57,375 bp) contained 20 protein-coding genes, 2 ribosomal RNA genes, and 26 transfer RNA genes. Phylogene...
Article
2-Azahypoxanthine (AHX) was first isolated from the culture broth of the fungus Lepista sordida as a fairy ring-inducing compound. It has since been found that a large number of plants and mushrooms produce AHX endogenously and that AHX has beneficial effects on plant growth. The AHX molecule has an unusual, nitrogen-rich 1,2,3-triazine moiety of u...
Article
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The leading cause of death worldwide is cancer. Many reports have proved the beneficial effect of mushrooms in cancer. However, the precise mechanism is not completely clear. In the present study, we focused on the medicinal properties of biomolecules released by fairy ring-forming mushrooms. Fairy chemicals generally stimulate or inhibit the growt...
Article
Among the "fairy chemicals" involved in forming the natural phenomenon of "fairy rings," we focused on 2-aza-8-oxohypoxanthine (AOH) as a candidate functional cosmetic ingredient. In previous studies, AOH was confirmed to be safe for use on human skin, and no adverse reactions were observed in any of the safety studies. In this study, we report the...
Article
Here, we report the draft genome sequence of the white-rot basidiomycete fungus Phanerochaete sordida YK-624 (ATCC 90872), which was isolated in Yakushima, Kagoshima, Japan. The genome of this strain was found to be 41.2 Mbp, with a G+C content of 58.7%, and to comprise 17,108 predicted protein-coding sequences.
Article
In this study, major factors involved in regulating ethanol production from wood by the saprotrophic white-rot fungus Phanerochaete sordida YK-624 were investigated. P. sordida YK-624 produced ethanol from wood meal culture without the addition of any nutrients, and ethanol was produced from wood culture only when the oxygen concentration in headsp...
Article
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A clinical study was conducted to evaluate the efficacy of 2-aza-8-oxohypoxanthine (AOH) on human skin in a double-blind, placebo-controlled, and split-face comparative trial. To this end, a topical lotion containing 0.1% of AOH and its placebo formulation were applied in 20 Japanese subjects (age: 41–58 years, average: 48.4 ± 4.7 years) to their f...
Article
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In this study, we verified the effects of 2-aza-8-oxohypoxanthine (AOH) on human epidermal cell proliferation by performing DNA microarray analysis. Cell proliferation was assessed using the 3-(4,5-dimethylthiazol-2-yl)-2,5-diphenyltetrazolium bromide assay, which measures mitochondrial respiration in normal human epidermal keratinocyte (NHEK) cell...
Article
Lignocellulosic biomass is an organic matrix composed of cellulose, hemicellulose, and lignin. In nature, lignin degradation by basidiomycetes is the key step in lignocellulose decay. The white-rot fungus Phanerochaete sordida YK-624 (YK-624) has been extensively studied due to its high lignin degradation ability. It was demonstrated that YK-624 ca...
Article
White-rot fungi are thought to hold promise for development of a delignification pretreatment process for wood biorefinery that is less energy-consuming than current processes. However, the reaction must take place over weeks and consumes non-neglectable amounts of saccharides. To establish a biological process for wood biorefinery would first requ...
Article
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The development of methods for the detection and qualification of toxic substances in mushrooms is a rapidly growing research area in forensic toxicology. This study aimed to determine liquid chromatographic and mass spectrometric conditions applicable to the analysis of ustalic acid (UA) in Tricholoma ustale. We used HPLC coupled with single quadr...
Article
In this study, we report a more efficient heterologous expression of lectin from Pleurocybella porrigens (PPL) using an Escherichia coli-based expression system. The yield (9.3 mg/L culture broth) of recombinant PPL (rPPL) using this expression system was increased approximately 9-fold compared to our previous study. The rPPL obtained in this study...
Article
During the course of our investigations of fairy chemicals (FCs), we found S-ICAr-H (8a), as a metabolite of imidazole-4-carboxamide (ICA) in rice and yeast (Saccharomyces cerevisiae). In order to determine its absolute configuration, an efficient synthetic method of 8a was developed. This synthetic strategy was applicable to the preparation of ana...
Article
We previously identified a cytochrome P450 (CYP) derived from the white-rot fungus Phanerochaete chrysosporium as involved in degradation of acetamiprid, a neonicotinoid (NEO) insecticide. In the present study, we investigated biodegradation of other NEOs by P. chrysosporium, and attempted to identify the CYP enzyme responsible for NEO degradation....
Article
Hericium erinaceus (Yamabushitake in Japan) is a well-known edible and medicinal mushroom. We discovered antidementia compounds, hericenones C to H, from the fruiting bodies and erinacine A to I from the cultured mycelia of the fungus. Based on the data of the compounds, several clinical experiments were performed using the fungus. “Fairy rings” is...
Article
2-Azahypoxanthine (AHX) is a compound isolated from the agaricomycete Lepista sordida that forms fairy rings and 2-aza-8-oxohypoxanthine (AOH) is a metabolite of AHX in plants. In the present study, we assessed the safety of AOH for cosmetic applications via in vitro skin sensitization tests and human skin sensitization, phototoxicity, and photosen...
Article
Full-text available
Neovascular retinal degeneration is a leading cause of blindness in advanced countries. Anti-vascular endothelial growth factor (VEGF) drugs have been used for neovascular retinal diseases; however, anti-VEGF drugs may cause the development of chorioretinal atrophy in chronic therapy as they affect the physiological amount of VEGF needed for retina...
Article
Fairy rings resulting from a fungus-plant interaction appear worldwide. 2-Azahypoxanthine (AHX) and imidazole-4-carboxamide (ICA) were first isolated from the culture broth of one of the fairy ring-forming fungi, Lepista sordida. Afterward, a common metabolite of AHX in plants, 2-aza-8-oxohypoxanthine (AOH), was found in AHX-treated rice. The biosy...
Article
Plants interact with fungi in their natural growing environments, and relationships between plants and diverse fungal species impact plants in complex symbiotic, parasitic, and pathogenic ways. Over the past 10 years, we have intensively investigated plant growth regulators produced by mushrooms, and we succeeded in finding various regulators from...
Article
2-Azahypoxanthine (AHX) and imidazole-4-carboxamide (ICA) are fairy-ring causing compounds from a mushroom-forming fungus, Lepista sordida, and 2-aza-8-oxohypoxanthine (AOH) is a metabolite of AHX in plants. However, the safety of AOH had not yet been elucidated. In this study, we focused on AOH and performed safety evaluations of the compound usin...
Article
Lascivol was identified as the bitter compound in two Tricholoma species, T. aestuans and T. virgatum, and was previously isolated from the European mushroom T. lascivum. The structure of lascivol was previously solved by X-ray crystallographical analysis but its stereochemistry at C3 remained ambiguous. We thus re-examined the absolute configurati...
Article
A novel compound (1) and three known ones (2−4) were isolated from the fruiting bodies of Pleurocybella porrigens. The structure of the novel compound was determined by 1D and 2D NMR and HRESIMS data. The biological activity of 1−3 was evaluated using the A549 lung cancer cell line. The results showed the inhibitory activity of compounds 1−3 on the...
Article
Imidazole-4-carboxamide (ICA) and 2-azahypoxanthine (AHX) obtained from Lepista sordida inhibit and promote the growth of herbaceous plants, respectively. In this study, we examined the effects of these compounds on the growth and ectomycorrhizal (EM) colonization of Pinus densiflora seedlings inoculated with Tricholoma matsutake that forms EM asso...
Article
Full-text available
Idiopathic pulmonary fibrosis (IPF) is a chronic and fatal disease of unknown etiology; however, apoptosis of lung alveolar epithelial cells plays a role in disease progression. This intractable disease is associated with increased abundance of Staphylococcus and Streptococcus in the lungs, yet their roles in disease pathogenesis remain elusive. He...
Article
A novel compound, (R)-4-ethoxy-2-hydroxy-4-oxobutanoic acid (1), and six known compounds (2–7) were isolated from the fruiting bodies of the wild edible mushroom Leucopaxillus giganteus. The planar structure of 1 was determined by the interpretation of spectroscopic data analysis. The absolute configuration of 1 was determined by comparing specific...
Article
The highly oxidized natural products chaxine B and BB have been synthesized from ergosterol in eight steps according to a route inspired by their proposed biosynthesis; key steps were an oxidative cascade from a furan intermediate to an enol ester using MCPBA, followed by diastereoselective epoxidation and acyloxy migration. This concise synthesis...
Article
Using activity guided purification, four known compounds, sesquiterpene atractylenolide III (1), and the polyacetylenes 14-acetoxy-12-senecioyloxytetradeca-2E,8E,10E-trien-4,6-diyn-1-ol (2), 14-acetoxy-12-α-methylbutyl-2E,8E,10E-trien-4,6-diyn-1-ol (3), and 14-acetoxy-12-β -methylbutyl-2E,8E,10E-trien-4,6-diyn-1-ol (4), were isolated from a traditi...
Preprint
Full-text available
Background Lignocellulosic biomass is an organic matrix composed of cellulose, hemicellulose, and lignin. In nature, lignin degradation by basidiomycetes is the key step in lignocellulose decay. The white-rot fungus Phanerochaete sordida YK-624 (YK-624) has been extensively studied due to its high lignin degradation ability. In our previous study,...
Article
Full-text available
Exposure to corticosterone attenuates hippocampal CA1 long-term potentiation (LTP) via intracellular Zn²⁺ dysregulation. Here we report that effusol, a phenanthrene isolated from Chinese medicine Juncus effusus, rescues CA1 LTP attenuated by corticosterone. In vivo microdialysis experiment indicated that both increases in extracellular glutamate in...
Article
Full-text available
Hericium erinaceus is a medicinal mushroom that contains many molecules promising a plethora of therapeutic properties. In this study, the strain H.e.2 (MicUNIPV, University of Pavia, Italy) was isolated from a sporophore collected in Tuscany (Italy). Mycelium, primordium, and wild type and cultivated sporophores were analyzed by HPLC-UV-ESI/MS. Er...
Article
To develop the versatile methodology for genome mining of mushroom metabolites, we examined the production of bioactive diterpenes erinacines using genomic DNA sequences. In this report, we initially identified high expression loci (hot spots) in Aspergillus oryzae by sequencing the genomic DNAs from highly yielding transformants which were obtaine...
Article
The metabolism of imidazole-4-carboxamide (ICA) in plants has been unknown. Two metabolites (1 and 2) were isolated from ICA-treated rice, and their structures were determined by spectroscopic analysis including the single-crystal X-ray diffraction technique and synthesis. The ribotide of ICA (3), whose existence was predicted, was also synthesized...
Article
In order to develop a simple method for crossing two transformants, we first attempted to elucidate the fusion type (self-compatibility or -incompatible) of Phanerochaete sordida YK-624. Two transformants expressing green or red fluorescent protein derived from an auxotrophic mutant were constructed. Each recombinant protein fluoresced by expressio...
Article
Neonicotinoid insecticides have been widely used throughout the world over the last two decades. In the present study, we investigated the degradation of neonicotinoid insecticides nitenpyram (NIT) and dinotefuran (DIN) by the white-rot fungus Phanerochaete sordida YK-624. While NIT was completely degraded by P. sordida YK-624 under ligninolytic co...
Article
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We report here the draft genome sequence of Buttiauxella sp. strain A111, isolated on the basis of bioconversion activity of the plant growth-regulating compound 2-azahypoxanthine to 2-aza-8-oxohypoxanthine. The genome contains 4,388 protein-coding sequences, including several genes possibly involved in the metabolism of the plant growth-regulating...
Article
Full-text available
Rings or arcs of fungus-regulated plant growth occurring on the floor of woodlands and grasslands are commonly called “fairy rings”. Fairy chemicals, 2-azahypoxanthine (AHX), imidazole-4-carboxamide (ICA), and 2-aza-8-oxohypoxanthine (AOH), are plant growth regulators involved in the phenomenon. The endogeny and biosynthetic pathways of AHX and AOH...
Article
Major facilitator superfamily (MFS) transporters are found in all organisms. Although numerous studies have examined the functions of yeast and mold MFS transporters in terms of sugar affinity and metabolic regulation, no functional analyses of MFS sugar transporters in white rot fungi have been reported. This study identified an MFS sugar transpor...
Article
Full-text available
Circular patterns called “fairy rings” in fields are a natural phenomenon that arises through the interaction between basidiomycete fungi and plants. Acceleration or inhibition of plant vegetative growth and the formation of mushroom fruiting bodies are both commonly observed when fairy rings form. The gene of an enzyme involved in the biosynthesis...
Article
Because cyanobacteriochrome photoreceptors need only a single compact domain for chromophore incorporation and for absorption of visible spectra including the long-wavelength far-red region, these molecules have been paid much attention for application to bioimaging and optogenetics. Most cyanobacteriochromes, however, have a drawback to incorporat...
Article
Full-text available
Frailty is a geriatric syndrome associated with both locomotor and cognitive decline, implicated in both poor quality of life and negative health outcomes. One central question surrounding frailty is whether phenotypic frailty is associated with the cognitive impairment during aging. Using spontaneous behavioral tests and by studying the dynamic ch...
Article
Full-text available
Three novel compounds, erinachromanes A and B (1, 2), and erinaphenol A (3), along with eight known compounds (4–11) were isolated from the culture broth of Hericium erinaceus. The structures of 1–3 were determined by the interpretation of spectroscopic data. Although compounds 4 and 9 had been synthesized, they were isolated from a natural source...
Article
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White-rot fungi are microorganisms capable of ethanol fermentation; however, the specific conditions activating ethanol fermentation are unclear in contrast to fermentation by yeasts. In this study, we investigated the conditions favoring ethanol fermentation by the white-rot fungus Phanerochaete sordida YK-624, which is able to produce ethanol fro...
Article
We previously reported that cytochrome P450 s play critical roles in neonicotinoid insecticide biodegradation by white-rot fungi. Here, we investigated the biodegradation of acetamiprid (ACET) by Phanerochaete chrysosporium to identify the cytochrome P450 involved in this degradation process. During a 20-day incubation period, P. chrysosporium degr...
Article
An α-L-fucosidase (Pap-Alf) was purified from the pancreas of a starfish Patiria pectinifera by ammonium sulfate precipitation followed by several column chromatographies. The molecular mass of the purified enzyme was estimated to be 52.6 kDa by SDS-PAGE, although gel filtration analysis of the native enzyme suggests it exists as a homodimer in sol...
Article
Full-text available
2-Azahypoxanthine (AHX, 1) and imidazole-4-carboxamide (ICA, 2) were isolated from a fairy-ring-forming fungus Lepista sordida. AHX was converted into a metabolite 2-aza-8-oxo-hypoxanthine (AOH, 3) in plants. It was found out that these three compounds, named as fairy chemicals (FCs), endogenously exist in plants and are biosynthesized via a new pu...
Article
Full-text available
Stropharia rugosoannulata (Strophariaceae, Basidiomycota) is an edible mushroom distributed in northern temperate zones throughout the world. In this study, the complete mitochondrial genome sequence of S. rugosoannulata was determined. This mitochondrial genome is 60,551 bp in length with a GC content of 31.0% and encodes 14 conserved proteins, 2...
Article
Grifola gargal is a medicinal mushroom with biological effects, such as antiatherogenic activity, and is used as a treatment for various chronic inflammatory diseases. The aim of this study is to investigate the antidiabetic and antiobesity effects of a low-molecular weight hot water extract from G. gargal (GGL) against diabetes type 2. In a human...
Article
A series of new AHX derivatives were synthesized by Pd-catalyzed C–H arylation. Their rice-growth-promoting activity was evaluated in vivo. Among the synthesized compounds, C8 phenyl-substituted AHX showed remarkable growth-promoting activity on rice. The present study shows the power and significant opportunity of C–H functionalization chemistry t...
Article
Double-¹³C-labeled imidazole-4-carboxamide (ICA: ¹³C2-1) and 5-aminoimidazole-4-carboxamide-1-β-riboside (AICAr: ¹³C2-5) were synthesized from stable isotope-labeled sodium cyanide and triethyl orthoformate. The key intermediate, 4-aminoimidazole-5-carboxamide (AICA: ¹³C2-4), should also provide access to double-¹³C-labeled histidine and adenosine...
Article
We investigated the potential of white-rot fungi for bioremediation of aqueous environments contaminated with diuron (3-(3,4-dichlorophenyl)-1,1-dimethylurea). First, diuron degradation activities of several white-rot fungi (Ceriporia lacerata, Phanerochaete chrysosporium, Phanerochaete sordida, Trametes versicolor) and a brown-rot fungus (Gloeophy...
Article
A homologue gene of the yeast natural resistance–associated macrophage protein (Nramp) family transporter smf2 was identified in the white-rot fungus Phanerochaete sordida YK-624. Relative expression levels of the homologue, designated PsMnt, were roughly equivalent in cultures containing 0 to 1,000 μM Mn(II), a concentration nontoxic to the fungus...
Article
2-Azahypoxanthine (AHX, 1) and imidazole-4-carboxamide (ICA, 2) were isolated from a fairy-ring forming fungus Lepista sordida. AHX was converted into a metabolite, 2-aza-8-oxohypoxanthine (AOH, 3), in plants. Afterward, it turned out that these three compounds, fairy chemicals (FSc), endogenously exist in plants and are biosynthesized via a new pu...
Chapter
This chapter presents some of our studies on biologically functional molecules isolated from mushroom-forming fungi. (1) Antidementia compounds: hericenones C to H were found from Hericium erinaceus. These compounds were the first nerve growth factor stimulators isolated from nature. Later, we also obtained erinacines A to I from the mycelia of the...
Article
2-Azahypoxanthine (AHX, 1) and imidazole-4-carboxamide (ICA, 2) were isolated from a fairy-ring forming fungus Lepista sordida. AHX was converted into a metabolite, 2-aza-8-oxohypoxanthine (AOH, 3), in plants. Afterward, it turned out that these three compounds, fairy chemicals (FCs), endogenously exist in plants and are biosynthesized via a new pu...
Article
Grifola gargal Singer, a medicinal mushroom, has been found to be effective for the prevention and treatment of various chronic inflammatory diseases. However, the effects of G. gargal on allergic diseases are unknown. The present study investigated the effect of G. gargal extract on allergic bronchial asthma. Asthma was induced in mice by ovalbumi...
Article
Plant growth stimulators, 2-azahypoxanthine (AHX) and 2-aza-8-oxohypoxanthine (AOH), were isolated from the fairy-ring-forming fungus, Lepista sordida, and AHX-treated rice, respectively. Further metabolites of AHX were detected in AHX-treated rice by HPLC, and the metabolites 1–4 were isolated from the rice. The structures of 1–4 were determined b...
Article
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Six compounds, 5-(1-hydroxyethyl)dihydrofuran-2(3. H)-one (1), 4-ethoxy-4-oxobutanoic acid (2), 4-ketononanoic acid (3), methyl(2-acetylaminoethyl)sulfoxide (4), methyl benzoate (5) and p-hydroxybenzoic acid (6) were isolated from the fruiting bodies of Cortinarius caperatus. Compounds 1, 3, 5, and 6 inhibited growth of Flammulina velutipes mycelia...
Article
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Burkholderia contaminans strain CH-1 converts 2-azahypoxnathine to 2-aza-8-oxohypoxanthine, plant growth-regulating compounds, by oxidation. We report here the high-quality draft genome sequence of B. contaminans CH-1. The genome contains 8,065 protein-coding sequences, including several genes possibly involved in metabolizing 2-azahypoxanthine.