Isolation of Isoterrein from Neosartorya fischeri

Wakana, Daigo; Hosoe, Tomoo; Itabashi, Takeshi; Nozawa, Koohei; Kawai, Ken‐ichi; Okada, Kaoru; Takaki, Galba Maria de Campos; Yaguchi, Takashi; Fukushima, Kazutaka

doi:10.2520/myco.56.3

Cited by 31 publications

(22 citation statements)

References 8 publications

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“…A literature search revealed that the NMR data of the isolated compound corresponded very well to those of acetylaszonalenin (3,4). Aszonalenin was previously isolated from another N. fischeri strain IFM52672 (7). MS data confirmed the structure of the isolated compound as acetylaszonalenin.…”

Section: Resultsmentioning

confidence: 54%

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Acetylaszonalenin Biosynthesis in Neosartorya fischeri

Yin

Grundmann

Cheng

et al. 2009

Journal of Biological Chemistry

153

129

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Based on the structural information of acetylaszonalenin isolated from Neosartorya fischeri, a putative biosynthetic gene cluster was identified in the genome sequence of this fungus by genomic mining. This cluster consists of three genes coding for a putative non-ribosomal peptide synthetase (AnaPS), a prenyltransferase (AnaPT), and an acetyltransferase (AnaAT). The coding sequences of anaPT and anaAT were cloned in pQE70 and pQE60, respectively, and overexpressed in Escherichia coli. The soluble His 6 fusion proteins were purified to near homogeneity and characterized biochemically. The structures of the enzymatic products were elucidated by NMR and mass spectroscopy analysis. AnaPT was found to catalyze the reverse prenylation of (

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Section: Resultsmentioning

confidence: 54%

“…Together with its non-acetylated form aszonalenin, it was also identified in various fungal strains, e.g. Aspergillus zonatus (4), Aspergillus fumigatus (5), Aspergillus carneus (6), and Neosartorya fischeri IFM52672 (7). Their stereoisomer epiaszonalenins A ( Fig.…”

Section: From the Philipps-universität Marburg Institut Für Pharmazementioning

confidence: 99%

Acetylaszonalenin Biosynthesis in Neosartorya fischeri

Yin

Grundmann

Cheng

et al. 2009

Journal of Biological Chemistry

153

129

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“…Fungus A. terreus PT06-2 was incubated in a high-salt medium containing 10% salt and extracted with EtOAc to afford a crude extract. The crude extract (31.2 g) was separated by extensive chromatography using silica gel, Sephadex LH-20 and HPLC to give compounds 1 – 15 ( Figure 1 ), including three new compounds: terremides A and B ( 1 , 2 ), terrelactone ( 3 ), and twelve known ones: methyl 3,4,5-trimethoxy-2-(2-(nicotinamido)benzamido)benzoate ( 4 ) [ 15 ], (+)-butyrolactones I–III ( 5 – 7 ) [ 16 – 19 ], 3-hydroxy-5-[[4-hydroxy-3-(3-methyl-2-buten-1-yl)phenyl]methyl]-4-(4-hydroxyphenyl)-2(5 H )-furanone ( 8 ) [ 20 ], aspernolide A ( 9 ) [ 16 ], 5-[(3,4-dihydro-2,2-dimethyl-2 H -1-benzopyran-6-yl)-methyl]-3-hydroxy-4-(4-hydroxyphenyl)-2(5 H )-furanone ( 10 ) [ 18 ], territrem B ( 11 ) [ 22 ], (−)-(1 R ,4 R )-1,4-(2,3)-indomethane-1-methyl-2,4-dihydro-1 H -pyrazino[2,1- b ]quinazoline-3,6-dione ( 12 ) [ 23 ], R (−)-6-hydroxymellein ( 13 ) [ 24 ], trans -4,6-dihydroxymellein ( 14 ) [ 25 ], and (+)-terrein ( 15 ) [ 26 ].…”

Section: Resultsmentioning

confidence: 99%

“…Chemical screening for A. terreus PT06-2 showed that the chemical diversity of the secondary metabolites is the richest at 10% salinity compared with those at 0% and 3% salt. Chemical investigation in 10% salinity resulted in isolation and identification of three new compounds, terremides A and B ( 1 , 2 ), terrelactone ( 3 ), along with twelve known compounds ( 4 – 15 ) [ 15 – 26 ]. Antibacterial activity of the new compound 2 against Enterobacter aerogenes , and the new compound 1 and 4 against Pseudomonas aeruginosa were observed.…”

Section: Introductionmentioning

confidence: 99%

Three New Compounds from Aspergillus terreus PT06-2 Grown in a High Salt Medium

et al. 2011

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To investigate the structurally novel and bioactive natural compounds from marine-derived microorganisms under high salinity, the fungus Aspergillus terreus PT06-2 was isolated from the sediment of the Putian Sea Saltern, Fujian, China. Three new compounds, terremides A (1) and B (2) and terrelactone A (3), along with twelve known compounds (4–15) were isolated and identified from the fermentation broth of A. terreus PT06-2 at 10% salinity. Among these metabolites, compounds 4 and 15 only produced in the 10% salinity culture, were identified as methyl 3,4,5-trimethoxy-2-(2-(nicotinamido) benzamido) benzoate, and (+)-terrein, respectively. The new compounds 1 and 2 exhibited antibacterial activity against Pseudomonas aeruginosa and Enterobacter aerogenes with MIC values of 63.9 and 33.5 μM, respectively. Compounds 5 showed moderate anti-H1N1 activity and lower cytotoxicity with IC50 and CC50 values of and 143.1 and 976.4 μM, respectively.

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“…6.1 and 6.4 ). Aszonalenin and its acetylated derivative acetylaszonalenin are produced by Aspergillus zonatus [ 57 ], A. fumigatus [ 58 ], A. carneus [ 59 ], and N. fi scheri NRRL 181 [ 60 ].…”

Section: The Biosynthesis Of Acetylaszonaleninmentioning

confidence: 99%

Roquefortine C and Related Prenylated Indole Alkaloids

2014

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IntroductionMany fungal metabolites, collectively designated as indole alkaloids contain in their structures a prenylated indole nucleus that derives from l -tryptophan and mevalonate. These metabolites include two large groups: (1) the ergot alkaloids produced by plant parasitic Claviceps species [ 1 ], and (2) the indole alkaloids produced by species of Aspergillus , Penicillium , and Neosartorya among others [ 2 ]. These alkaloids differ: (1) in the carbon atom of the indole molecule bearing the isopentenyl group, (2) in modifi cations of the diketopiperazine ring, and (3) in modifi cations of the N1 atom of indole, that are introduced by "late" modifi cation enzymes encoded by additional genes in the clusters.One of the best known indole alkaloid groups is that of the ergot alkaloids [ 1 ] that are reviewed in a separate chapter in this book. Another important group is that of roquefortine C and related indole alkaloids (glandicoline, meleagrin, neoxaline) [ 3 , 4 ]. Several of these mycotoxins are produced by Penicillium species of the Corymbifera family, which infect onions, tulips, and other plant bulbs (Table 6.1 ) [ 5 ]. Others are produced by Penicillium species growing on cheese [ 6 ] or in contaminated food products and cereal grains. The acetylaszonalenin producer N. fi scheri (formerly Aspergillus fi scheri ) is an opportunistic human pathogen closely related to the pathogenic Aspergillus fumigatus [ 7 , 8 ].

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Isolation of Isoterrein from Neosartorya fischeri

Cited by 31 publications

References 8 publications

Acetylaszonalenin Biosynthesis in Neosartorya fischeri

Acetylaszonalenin Biosynthesis in Neosartorya fischeri

Three New Compounds from Aspergillus terreus PT06-2 Grown in a High Salt Medium

Roquefortine C and Related Prenylated Indole Alkaloids

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