Antibiotic Y: biosynthesis by Fusarium avenaceum (Corda ex Fries) Sacc., isolation, and some physicochemical and biological properties

Goliński, Piotr; Wnuk, Stanislaw F.; Chełkowski, J.; Visconti, Angelo; Schollenberger, M.

doi:10.1128/aem.51.4.743-745.1986

Cited by 20 publications

(5 citation statements)

References 6 publications

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“…Ascochitine spot after esterification on the TLC plate also did not migrate during the redeveloping of chromatogram and the colour of the fluorescence changed to green. Above chemical confirmatory tests definitively distinguished the three compounds[12]. Aluminium plates impregnated with 0.3 M H,SO, and dryed at 50 "C Tab.…”

mentioning

confidence: 87%

Biosynthesis, preparation and properties of ascochitine

Foremska¹,

Kostecki²,

Chełkowski³

1992

Acta Biotechnologica

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confidence: 87%

Biosynthesis, preparation and properties of ascochitine

Foremska¹,

Kostecki²,

Chełkowski³

1992

Acta Biotechnologica

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“…The structure was later amended and named antibiotic Y . This compound is produced by several Fusarium species, including F. avenaceum , F. lateritium , F. torulosum, F. acuminatum , F. flocciferum , and F. tricinctum ,− , and it has, as the name suggests, antibiotic properties . Aurofusarin is a red pigment belonging to the naphthoquinone group and is produced by several Fusarium species , .…”

Section: Introductionmentioning

confidence: 99%

“…Fusarin AandCaremetabolitesproducedbyseveralFusariumspecies (15,16) and show mutagenic properties (17). Antibiotic Y was originally (18,(20)(21)(22), and it has, as the name suggests, antibiotic properties (18). Aurofusarin is a red pigment belonging to the naphthoquinone group and is produced by several Fusarium species (21,22).…”

Section: Introductionmentioning

confidence: 99%

Analysis ofFusarium avenaceumMetabolites Produced during Wet Apple Core Rot

Sørensen¹,

Phipps²,

Nielsen³

et al. 2009

J. Agric. Food Chem.

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Wet apple core rot (wACR) is a well-known disease of susceptible apple cultivars such as Gloster, Jona Gold, and Fuji. Investigations in apple orchards in Slovenia identified Fusarium avenaceum, a known producer of several mycotoxins, as the predominant causal agent of this disease. A LC-MS/MS method was developed for the simultaneous detection of thirteen F. avenaceum metabolites including moniliformin, acuminatopyrone, chrysogine, chlamydosporol, antibiotic Y, 2-amino-14,16-dimethyloctadecan-3-ol (2-AOD-3-ol), aurofusarin, and enniatins A, A1, B, B1, B2, and B3 from artificially and naturally infected apples. Levels of moniliformin, antibiotic Y, aurofusarin, and enniatins A, A1, B, and B1 were quantitatively examined in artificially inoculated and naturally infected apples, whereas the remaining metabolites were qualitatively detected. Metabolite production was examined in artificially inoculated apples after 3, 7, 14, and 21 days of incubation. Most metabolites were detected after 3 or 7 days and reached significantly high levels within 14 or 21 days. The highest levels of moniliformin, antibiotic Y, aurofusarin, and the combined sum of enniatins A, A1, B, and B1 were 7.3, 5.7, 152, and 12.7 microg g(-1), respectively. Seventeen of twenty naturally infected apples with wACR symptoms contained one or more of the metabolites. Fourteen of these apples contained moniliformin, antibiotic Y, aurofusarin, and enniatins in levels up to 2.9, 51, 167, and 3.9 microg g(-1), respectively. Acuminatopyrone, chrysogine, chlamydosporol, and 2-AOD-3-ol were detected in 4, 11, 4, and 10 apples, respectively. During wet apple core rot, F. avenaceum produced high amounts of mycotoxins, which may pose a risk for consumers of apple or processed apple products.

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“…Antibiotic Y ( 13 ) (avenacein Y) was first isolated from F. avenaceum in 1986, and although its biosynthetic pathway is unknown, it displays several structural features in common with YWA1 and rubrofusarin. This suggest that it may also be formed via the nonreducing polyketide biosynthetic pathway .…”

mentioning

confidence: 97%

“…27 After release from the PKS, YWA1 is converted into nor-rubrofusarin (9), rubrofusarin (10), 9-hydroxyrubrofusarin, and finally the dimers fuscofusarin (11) and aurofusarin. 29 Antibiotic Y (13) (avenacein Y) was first isolated from F. avenaceum in 1986, and although its biosynthetic pathway is unknown, 30 it displays several structural features in common with YWA1 and rubrofusarin. This suggest that it may also be formed via the nonreducing polyketide biosynthetic pathway.…”

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confidence: 99%

Combining UHPLC-High Resolution MS and Feeding of Stable Isotope Labeled Polyketide Intermediates for Linking Precursors to End Products

et al. 2015

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We present the results from stable isotope labeled precursor feeding studies combined with ultrahigh performance liquid chromatography-high resolution mass spectrometry for the identification of labeled polyketide (PK) end-products. Feeding experiments were performed with (13)C8-6-methylsalicylic acid (6-MSA) and (13)C14-YWA1, both produced in-house, as well as commercial (13)C7-benzoic acid and (2)H7-cinnamic acid, in species of Fusarium, Byssochlamys, Aspergillus, and Penicillium. Incorporation of 6-MSA into terreic acid or patulin was not observed in any of six evaluated species covering three genera, because the 6-MSA was shunted into (2Z,4E)-2-methyl-2,4-hexadienedioic acid. This indicates that patulin and terreic acid may be produced in a closed compartment of the cell and that (2Z,4E)-2-methyl-2,4-hexadienedioic acid is a detoxification product toward terreic acid and patulin. In Fusarium spp., YWA1 was shown to be incorporated into aurofusarin, rubrofusarin, and antibiotic Y. In A. niger, benzoic acid was shown to be incorporated into asperrubrol. Incorporation levels of 0.7-20% into the end-products were detected in wild-type strains. Thus, stable isotope labeling is a promising technique for investigation of polyketide biosynthesis and possible compartmentalization of toxic metabolites.

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Antibiotic Y: biosynthesis by Fusarium avenaceum (Corda ex Fries) Sacc., isolation, and some physicochemical and biological properties

Cited by 20 publications

References 6 publications

Biosynthesis, preparation and properties of ascochitine

Biosynthesis, preparation and properties of ascochitine

Analysis ofFusarium avenaceumMetabolites Produced during Wet Apple Core Rot

Combining UHPLC-High Resolution MS and Feeding of Stable Isotope Labeled Polyketide Intermediates for Linking Precursors to End Products

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