Isolation of Aromatic Compounds Produced by Eurotium herbariorum NU-2 from Karebushi, a Katsuobushi, and their DPPH-Radical Scavenging Activities

Miyake, Yoichi; Ito, Chihiro; Kimura, Takeshi; Suzuki, Ayaka; Nishida, Yoshio; Itoigawa, Masataka

doi:10.3136/fstr.20.139

Cited by 21 publications

(16 citation statements)

References 23 publications

(30 reference statements)

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“…and (δ c 127.5, C-2) which confirms the presence of the unsaturation protons at H-1 and its relation to C-2 in the aromatic ring. The NMR data of compound 1 were identical with the published for dihydroauroglaucin with molecular formula C 19 H 24 O 3 [21][22][23].…”

Section: Identification and Elucidation Of The Isolated Compoundssupporting

confidence: 52%

Bio-guided fractionation of prenylated benzaldehyde derivatives as potent antimicrobial and antibiofilm from Ammi majus L. fruits-associated Aspergillus amstelodami

Salama

Fathallah

Raafat

et al. 2019

67th International Congress and Annual Meeting of the Society for Medicinal Plant and Natural Product Research (GA) in Cooperat

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Ammi majus L.; Family Apiaceae; is a plant indigenous to Egypt. Its fruits contain bioactive compounds such as furanocoumarins and flavonoids of important biological activities. An endophytic fungus was isolated from the fruits and identified as Aspergillus amstelodami (MK215708) by morphology, microscopical characterization, and molecular identification. To our knowledge this is the first time an endophytic fungus has been isolated from the fruits. The antimicrobial activity of the Ammi majus ethanol fruits extract (AME) and fungal ethyl acetate extract (FEA) were investigated, where the FEA showed higher antimicrobial activity, against all the tested standard strains. Phytochemical investigation of the FEA extract yielded five prenylated benzaldehyde derivative compounds isolated for the first time from this species: Dihydroauroglaucin (1), tetrahydroauroglaucin (2), 2-(3,6-dihydroxyhepta-1,4-dien-1-yl)-3,6-dihydroxy-5-(dimethylallyl)benzaldehyde (3), isotetrahydroauroglaucin)4), and flavoglaucin (5). Structure elucidation was carried out using (1Hand 13C-NMR). Fractions and the major isolated compound 1 were evaluated for their antimicrobial and antibiofilm activity. Compound 1 showed high antimicrobial activity against Escherichia coli with minimum inhibitory concentration (MIC) = 1.95 µg/mL, Streptococcus mutans (MIC = 1.95 µg/mL), and Staphylococcus aureus (MIC = 3.9 µg/mL). It exhibited high antibiofilm activity with minimum biofilm inhibitory concentration (MBIC) = 7.81 µg/mL against Staphylococcus aureus and Escherichia coli biofilms and MBIC = 15.63 µg/mL against Streptococcus mutans and Candida albicans and moderate activity (MBIC = 31.25 µg/mL) against Pseudomonas aeruginosa biofilm. This reveals that dihydroauroglaucin, a prenylated benzaldehyde derivative, has a broad spectrum antimicrobial activity. In conclusion, it was observed that the MICs of the FEA are much lower than that of the AME against all susceptible strains, confirming that the antimicrobial activity of Ammi majus may be due to the ability of its endophytic fungi to produce effective secondary metabolites.

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Section: Identification and Elucidation Of The Isolated Compoundssupporting

confidence: 52%

Bio-guided fractionation of prenylated benzaldehyde derivatives as potent antimicrobial and antibiofilm from Ammi majus L. fruits-associated Aspergillus amstelodami

Salama

Fathallah

Raafat

et al. 2019

67th International Congress and Annual Meeting of the Society for Medicinal Plant and Natural Product Research (GA) in Cooperat

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“…2016 ) Asperflavins Anhydroasperflavin, asperflavin, asperflavin ribofuranoside, isoasperflavin Grove 1972a (misidentified as A. flavus ), Anke et al., 1978 , Fujimoto et al., 1999 , Li et al., 2006 (misidentified as Microsporum ), Smetanina et al., 2007 , Du et al., 2008 , Du et al., 2014 A. glaucus , A. pseudoglaucus , A. megasporus Isotorachrysones Isotorachrysone, isotarachrysone 6-O-α-D-ribofuranoside, 8-methoxy-3-methyl-1-naphthalenol-6-O-α-D-ribofuranoside, 8-methoxy-1-naphthalenol-6-O-α-D-ribofuranoside, (+)-variecolorquinone A, aspergiodiquinone Wang et al. 2007a (misidentified as A. variecolor ), Du et al., 2008 , Sun et al., 2013 A. glaucus Aspergiolides Aspergiolide A, B, C, D Du et al., 2007 , Du et al., 2008 , Du et al., 2011 , Sun et al., 2009 , Sun et al., 2013 , Tao et al., 2009 A. glaucus Eurotionones Eurotinone, variecolorquinone B, 2-methyleurotinone, 9-dehydroxyeurotinone, 2-O-methyl-9-dehydroxyeurotinone, 2-O-methyl-4-O-(α-D-ribofuranosyl)-9-dehydroxyeurotinone, all related to anthraquinones, (+) & (−) europhenol A Wang et al., 2007c , Li et al., 2009 , Yan et al., 2012 , Miyake et al., 2014 , Meng et al., 2016 A. ruber Bianthrons ( trans ) & ( cis )-emodin-physcion bianthrone, physcionanthrone (= physciondianthranol), physcion bianthrone (= physcion-dianthrone = physcion anthrone dimer), physcion-anthrone A (= physcion-9-anthrone), physcion anthrone B Ashley et al., 1939 , Bachmann et al., 1979 , Anke et al., 1980a , Anke et al., 1980b A. cristatus , A. chevalieri Asperentins ...…”

Section: Resultsmentioning

confidence: 99%

“…2014 A. cristatus Kotanins Desmethylkotanin, kotanin Büchi et al. 1971 A. glaucus Auroglaucins Auroglaucin, flavoglaucin, dihydroauroglaucin, isodihydroauroglaucin, isotetrahydroauroglaucin (= dihydroflavoglaucin), chaetopyranin, 2-(2′,3-epoxy-1′,3-heptadienyl)-6-hydroxy-5-(3-methyl-2-butenyl)benzaldehyde, tetrahydroauroglaucin, (E)-2-(hept-1-enyl)-3-(hydroxymethyl)-5-(3-methylbut-2-enyl)benzene-1,4-diol, (E)-4-(hept-1-enyl)-7-(3-methylbut-2-enyl)-2,3-dihydrobenzofuran-2,5-diol, eurotirumin, 2-(2′,3-epoxy-1′-heptenyl)-6-hydroxy-5-(3″-methyl-2″-butenyl)benaldehyde, (E)-6-hydroxy-7-(3-methyl-2-butenyl)-2-(3-oxobut-1-enyl)chroman-5-carbaldehyde, 2-(1′,5′-heptadienyl)3,6-dihydroxy-5-(3″-methyl-2″butenyl)benzaldehyde, aspergentisyl A, B, aspergin Gould and Raistrick, 1934 , Ashley et al., 1939 , Quilico et al., 1949 , Birch, 1958 , Inoue et al., 1977c , Hamasaki et al., 1980 , Hamasaki et al., 1981 , Ishikawa et al., 1984 , Ishikawa et al., 1985 , Li et al., 2006 , Wang et al., 2006 (as Chaetomium globosum ), Li et al., 2008a , Li et al., 2008b , Miyake et al., 2009 , Slack et al., 2009 , Almeida et al., 2010 , Miyake et al., 2010a , Miyake et al., 2010b , Gao et al., 2011 , Gao et al., 2012a , Gao et al., 2012b , Gao et al., 2013 (misidentified as A. effusus ), Sun et al., 2013 , Wu et al., 2013 , Miyake et al., 2014 , Visagie et al., 2017 A. brunneus , A. glaucus , A. glaucus ? (as Microsporum sp.…”

Section: Resultsmentioning

confidence: 99%

Polyphasic taxonomy of Aspergillus section Aspergillus (formerly Eurotium), and its occurrence in indoor environments and food

Chen¹,

Hubka²,

Frisvad³

et al. 2017

Studies in Mycology

118

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Aspergillus section Aspergillus (formerly the genus Eurotium) includes xerophilic species with uniseriate conidiophores, globose to subglobose vesicles, green conidia and yellow, thin walled eurotium-like ascomata with hyaline, lenticular ascospores. In the present study, a polyphasic approach using morphological characters, extrolites, physiological characters and phylogeny was applied to investigate the taxonomy of this section. Over 500 strains from various culture collections and new isolates obtained from indoor environments and a wide range of substrates all over the world were identified using calmodulin gene sequencing. Of these, 163 isolates were subjected to molecular phylogenetic analyses using sequences of ITS rDNA, partial β-tubulin (BenA), calmodulin (CaM) and RNA polymerase II second largest subunit (RPB2) genes. Colony characteristics were documented on eight cultivation media, growth parameters at three incubation temperatures were recorded and micromorphology was examined using light microscopy as well as scanning electron microscopy to illustrate and characterize each species. Many specific extrolites were extracted and identified from cultures, including echinulins, epiheveadrides, auroglaucins and anthraquinone bisanthrons, and to be consistent in strains of nearly all species. Other extrolites are species-specific, and thus valuable for identification. Several extrolites show antioxidant effects, which may be nutritionally beneficial in food and beverages. Important mycotoxins in the strict sense, such as sterigmatocystin, aflatoxins, ochratoxins, citrinin were not detected despite previous reports on their production in this section. Adopting a polyphasic approach, 31 species are recognized, including nine new species. ITS is highly conserved in this section and does not distinguish species. All species can be differentiated using CaM or RPB2 sequences. For BenA, Aspergillus brunneus and A. niveoglaucus share identical sequences. Ascospores and conidia morphology, growth rates at different temperatures are most useful characters for phenotypic species identification.

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“…Asperflavin was initially isolated from entomogenous strain of Aspergillus flavus . It was also found in the marine-derived fungi of E urotium rubrum, Eurotium repens , Eurotium cristatum and the fungus of Eurotium herbariorum which was used in the process of manufacturing karebushi (a katsuobushi) [ 33 , 34 , 35 ]. However, there are few reports to date on the biological activity of asperflavin.…”

Section: Discussionmentioning

confidence: 99%

Asperflavin, an Anti-Inflammatory Compound Produced by a Marine-Derived Fungus, Eurotium amstelodami

Yang

Kang

et al. 2017

Molecules

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In the present study, 16 marine-derived fungi were isolated from four types of marine materials including float, algae, animals and drift woods along with the coast of Jeju Island, Korea and evaluated for anti-inflammatory effects in lipopolysaccharide (LPS)-stimulated RAW 24.7 cells. The broth and mycelium extracts from the 16 fungi were prepared and the broth extract (BE) of Eurotium amstelodami (015-2) inhibited nitric oxide (NO) production in LPS-stimulated RAW 264.7 cells without cytotoxicity. By further bioassay-guided isolation, three compounds including asperflavin, neoechinulin A and preechinulin were successfully isolated from the BE of E. amstelodami. It was revealed that asperflavin showed no cytotoxicity up to 200 μM and significantly inhibited LPS-induced NO and PGE2 production in a dose-dependent manner. In the western blot results, asperflavin suppressed only inducible NOS (iNOS), but COX-2 were slightly down-regulated. Asperflavin was also observed to inhibit the production of pro-inflammatory cytokines including TNF-α, IL-1β, and IL-6. In conclusion, this study reports a potential use of asperflavin isolated from a marine fungus, E. amstelodami as an anti-inflammatory agent via suppression of iNOS and pro-inflammatory cytokines as well as no cytotoxicity.

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Isolation of Aromatic Compounds Produced by Eurotium herbariorum NU-2 from Karebushi, a Katsuobushi, and their DPPH-Radical Scavenging Activities

Abstract: Aromatic compounds were isolated from an extract of

Cited by 21 publications

References 23 publications

Bio-guided fractionation of prenylated benzaldehyde derivatives as potent antimicrobial and antibiofilm from Ammi majus L. fruits-associated Aspergillus amstelodami

Bio-guided fractionation of prenylated benzaldehyde derivatives as potent antimicrobial and antibiofilm from Ammi majus L. fruits-associated Aspergillus amstelodami

Polyphasic taxonomy of Aspergillus section Aspergillus (formerly Eurotium), and its occurrence in indoor environments and food

Asperflavin, an Anti-Inflammatory Compound Produced by a Marine-Derived Fungus, Eurotium amstelodami

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