Fusarin C and 8Z-fusarin C from Gibberella fujikuroi

Barrero, Alejandro F.; Sánchez, Juan Francisco López; Oltra, J. Enrique; Tamayo, Nuria; Cerdá‐Olmedo, Enrique; Candau, Reyes; Ávalos, Javier

doi:10.1016/0031-9422(91)83625-u

Cited by 48 publications

(53 citation statements)

References 19 publications

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“…1 H NMR spectra of 4-8 and 12, as well as 13 C NMR of 6, agreed with those previously reported. [19][20][21][22] In the 1 21,23 confirmed their structures. The TMSsterol at T RR′ ) 1.325 showed an MS which matched both mass spectra of TMS derivatives from sitosterol (21) 12 and clionasterol (24-epi-sitosterol).…”

Section: Resultsmentioning

confidence: 85%

“…Searching for new bioactive products from filamentous fungi, chemical analysis and biological screening of metabolites from Gibberella fujikuroi have been the subject of our work over the past few years. [1][2][3] We recently began studying Phycomyces blakesleeanus (Mucoraceae), which is a fungal producer of -carotene (provitamin A), riboflavine (vitamin B 2 ), pyridoxine (vitamin B 6 ), ergosterol (provitamin D 2 ), biotin, and nicotinic acid. 4,5 Therefore, oil from Phycomyces could be an interesting alimentary vitamin complement, if it were proven to be free of mycotoxins.…”

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confidence: 99%

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Phycomysterols and Other Sterols from the Fungus Phycomyces blakesleeanus

Oltra

et al. 1998

J. Nat. Prod.

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In the search for novel bioactive products from filamentous fungi, sterols and triterpenoids found in Phycomyces blakesleeanus were analyzed using semipreparative HPLC, GC-MS, and NMR techniques. Structures proposed for the three new compounds identified, phycomysterol A (1), phycomysterol B (2), and neoergosterol (3), were confirmed by chemical synthesis. Phycomysterols possess a new natural 19-norergostane skeleton with an aromatic B ring. Phycomysterol A showed anti-HIV activity.Fungi have been one of the main natural sources of biologically active substances since the discovery of antibiotics. Searching for new bioactive products from filamentous fungi, chemical analysis and biological screening of metabolites from Gibberella fujikuroi have been the subject of our work over the past few years. [1][2][3] We recently began studying Phycomyces blakesleeanus (Mucoraceae), which is a fungal producer of -carotene (provitamin A), riboflavine (vitamin B 2 ), pyridoxine (vitamin B 6 ), ergosterol (provitamin D 2 ), biotin, and nicotinic acid. 4,5 Therefore, oil from Phycomyces could be an interesting alimentary vitamin complement, if it were proven to be free of mycotoxins. We have identified more than forty nontoxic compounds among the acidic metabolites from P. blakesleeanus 6 and are now working on neutral metabolites. In the mycelium of P. blakesleeanus (NRRL1555 wild strain) we have found eleven sterols previously unreported in Phycomyces. These include the new natural sterols (1-3; Chart 1) with a 19-norergostane skeleton and an aromatic B ring. Previous studies of sterols from Phycomyces at the University College of Wales yielded a number of new sterols (4-13) and certain aspects of fungal ergosterol biosynthesis were resolved. 7-11 However, some sterols present in the fungus were not identified. 9 Results and DiscussionSterol and triterpene mixtures isolated from P. blakesleeanus were subjected to semipreparative HPLC. Fractions obtained were studied by NMR spectroscopy and aliquots were treated with N,O-bis(trimethylsilyl)trifluoroacetamide (BSTFA) to form TMS derivatives for analysis by GC-MS. The sterol ester mixture was saponified, and the nonsaponifiable fraction was analyzed as described above. Results are shown in Table 1. Proportions are only approximate because they were determined from the area of the gas chromatogram peaks, based on total ion current response data. TMS-ethers of sterols were used for GC-MS analysis, instead of free sterols, because the former have better chromatographic properties and afford highly characteristic modes of fragmentation from which structural details may be inferred. 12 In the mass spectrum of 1, as the TMS-ether, the molecular ion was consistent with the TMS derivative of a sterol with the molecular formula C 27 H 40 O, containing four double bonds. The fragment ions [M -TMSOH -C 9 H 17 ] + , [M -TMSOH -C 6 H 11 ] + , and [M -(C 6 H 11 + H)] + indicated a side chain with nine carbon atoms and a double bond. Thus, 1 must possess a nucleus with three double bonds and ...

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Section: Resultsmentioning

confidence: 85%

mentioning

confidence: 99%

Phycomysterols and Other Sterols from the Fungus Phycomyces blakesleeanus

Oltra

et al. 1998

J. Nat. Prod.

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“…The extracted samples were vacuum dried and resuspended in 0.2 ml of methanol. Fusarin concentrations were determined through absorption at 350 nm using a UV/Vis spectrophotometer (Beckman DU, USA) as described previously (2).…”

Section: Methodsmentioning

confidence: 99%

“…Its production was induced by the lack of zinc (17) and by the presence of a high carbon concentration (16) in F. moniliforme. Fusarin C produced by F. fujikuroi (2) was enhanced upon growth at high temperature, low aeration (15), and nitrogen starvation (41). In addition to F. graminearum, the PKS responsible for fusarin biosynthesis (FusA/Fus1) has been identified in F. moniliforme, F. venenatum, and F. verticillioides (12,32,3).…”

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Identification and Regulation offusA, the Polyketide Synthase Gene Responsible for Fusarin Production in Fusarium fujikuroi

Díaz-Sánchez

Ávalos

Limón

2012

Appl Environ Microbiol

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Fusarins are a class of mycotoxins of the polyketide family produced by different Fusarium species, including the gibberellinproducing fungus Fusarium fujikuroi. Based on sequence comparisons between polyketide synthase (PKS) enzymes for fusarin production in other Fusarium strains, we have identified the F. fujikuroi orthologue, called fusA. The participation of fusA in fusarin biosynthesis was demonstrated by targeted mutagenesis. Fusarin production is transiently stimulated by nitrogen availability in this fungus, a regulation paralleled by the fusA mRNA levels in the cell. Illumination of the cultures results in a reduction of the fusarin content, an effect partially explained by a high sensitivity of these compounds to light. Mutants of the fusA gene exhibit no external phenotypic alterations, including morphology and conidiation, except for a lack of the characteristic yellow and/or orange pigmentation of fusarins. Moreover, the fusA mutants are less efficient than the wild type at degrading cellophane on agar cultures, a trait associated with pathogenesis functions in Fusarium oxysporum. The fusA mutants, however, are not affected in their capacities to grow on plant tissues.

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“…fujikuroi is well known for the production of the plant hormone gibberellic acid (GA), the causative agent of bakanae disease on rice, for more than 100 years (25). Besides gibberellins, the fungus produces a wide range of other secondary metabolites, such as the red polyketide pigments bikaverin (26,27) and fusarubins (28,29) and mycotoxins such as fusarin C (30), fusaric acid (31), or fumonisins (32). Furthermore, recent sequencing of the genome of F. fujikuroi wild-type (WT) strain IMI58289 revealed the presence of about 40 additional putative secondary-metabolite gene clusters, most of which are cryptic and silent under laboratory conditions (17).…”

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Two Histone Deacetylases, FfHda1 and FfHda2, Are Important for Fusarium fujikuroi Secondary Metabolism and Virulence

Studt

Schmidt

Jahn

et al. 2013

Appl Environ Microbiol

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Histone modifications are crucial for the regulation of secondary metabolism in various filamentous fungi. Here we studied the involvement of histone deacetylases (HDACs) in secondary metabolism in the phytopathogenic fungus Fusarium fujikuroi, a known producer of several secondary metabolites, including phytohormones, pigments, and mycotoxins. Deletion of three Zn 2؉ -dependent HDAC-encoding genes, ffhda1, ffhda2, and ffhda4, indicated that FfHda1 and FfHda2 regulate secondary metabolism, whereas FfHda4 is involved in developmental processes but is dispensable for secondary-metabolite production in F. fujikuroi. Single deletions of ffhda1 and ffhda2 resulted not only in an increase or decrease but also in derepression of metabolite biosynthesis under normally repressing conditions. Moreover, double deletion of both the ffhda1 and ffhda2 genes showed additive but also distinct phenotypes with regard to secondary-metabolite biosynthesis, and both genes are required for gibberellic acid (GA)-induced bakanae disease on the preferred host plant rice, as ⌬ffhda1 ⌬ffhda2 mutants resemble the uninfected control plant. Microarray analysis with a ⌬ffhda1 mutant that has lost the major HDAC revealed differential expression of secondarymetabolite gene clusters, which was subsequently verified by a combination of chemical and biological approaches. These results indicate that HDACs are involved not only in gene silencing but also in the activation of some genes. Chromatin immunoprecipitation with the ⌬ffhda1 mutant revealed significant alterations in the acetylation state of secondary-metabolite gene clusters compared to the wild type, thereby providing insights into the regulatory mechanism at the chromatin level. Altogether, manipulation of HDAC-encoding genes constitutes a powerful tool to control secondary metabolism in filamentous fungi.

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Fusarin C and 8Z-fusarin C from Gibberella fujikuroi

Cited by 48 publications

References 19 publications

Phycomysterols and Other Sterols from the Fungus Phycomyces blakesleeanus

Phycomysterols and Other Sterols from the Fungus Phycomyces blakesleeanus

Identification and Regulation offusA, the Polyketide Synthase Gene Responsible for Fusarin Production in Fusarium fujikuroi

Two Histone Deacetylases, FfHda1 and FfHda2, Are Important for Fusarium fujikuroi Secondary Metabolism and Virulence

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