Bisbynin, a novel secondary metabolite from the fungus Stachybotrys bisbyi (Srinivasan) Barron

Silva, L.B. De; Herath, Wimal; Gunawardena, D.S.S.; Wijesundera, R.L.C.; Medis, Sohani; Choudhary, M. Iqbal; Clardy, Jon

doi:10.1016/0040-4039(95)00211-t

Cited by 10 publications

(8 citation statements)

References 10 publications

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“…1-(2′-Hydroxy-4′-methoxy-5′-hydroxymethylphenyl)-E-4-hexen-1-one (5): white powder, mp 59-61 °C; UV (CH3OH) λmax 216 ( 9000), 230 ( 7000), 275 ( 6000), 320 ( 3000) nm; IR (film on NaCl plate) νmax 3307, 1635, 1498, 1446, 1378, 1273, 1209, 1141, 1029 cm -1 ; 1 H and 13 C NMR data, see Table 3; EIMS (70 eV) m/z 250 (M + ; rel int 6), 232 (19), 217 (4), 181 (100), 77 (12), 69 (13), 65 (18), 55 (50).…”

Section: Methodsmentioning

confidence: 99%

Phaeofurans and Sorbicillin Analogues from a FungicolousPhaeoacremoniumSpecies (NRRL 32148)

2006

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Two new benzofuran-derived metabolites of polyketide origin called phaeofurans A and B (1-2), along with three sorbicillin analogs (3-5) have been obtained from a fungicolous isolate of the genus Phaeoacremonium (NRRL 32148). The structures were determined by analysis of MS and 2D NMR data. The antifungal effects of the extract were ascribed to the sorbicillin analogs.Previous chemical studies of mycoparasites and fungicolous fungi that attack the nutrient-rich stromata of wood-decay fungi have yielded novel metabolites with antifungal effects and other biological activities. 1-6 As part of our ongoing studies of these types of fungi, chemical investigations of a culture identified as Phaeoacremonium sp. (Incertae sedis; NRRL 32148) isolated from field-collected stromata of Hypoxylon truncatum (Xylariaceae) produced two new polyketides named phaeofurans A and B (1-2) and three sorbicillin analogs (3-5), two of which have not been previously reported. Details of the isolation and structure determination of these compounds are presented here. Results and discussionSolid-substrate fermentation cultures of a Phaeoacremonium species grown on rice were extracted with ethyl acetate. The resulting extract showed antifungal activity against Aspergillus flavus and Fusarium verticillioides, and was partitioned between acetonitrile and hexane to yield an acetonitrile-soluble mixture that was subsequently fractionated over Sephadex LH-20. Active fractions were subjected to silica gel flash chromatography and/or reversed phase HPLC to yield compounds 1-5.Phaeofuran A (1) was isolated as a white film that formed fine needles upon evaporation of an acetone solution. The formula of 1 was tentatively assigned as CgHgCX based on analysis of EIMS (apparent M + at m/z 168) and NMR data ( Table 1). The intensities of the EIMS M + ion and the ESIMS M+H ion proved to be insufficient for obtaining high resolution MS data, but the NMR data suggested the presence of two exchangeable protons in the molecule, so a diacetate derivative of 1 was prepared. With five unsaturations, four olefinic or aromatic sp 2 carbon atoms (two of them protonated), four oxygenated sp 3 methines, and no carbonyl carbons, phaeofuran A (1) must contain three rings, two double bonds, and two OH groups. In addition, observation of four pairs of signals with very similar 13 C NMR chemical shifts (Table 1) suggested a pseudo-symmetrical structure. The NMR shifts for two of the oxymethine units (δ C 55.9 and 55.5/δ H 3.40 and 3.38) were diagnostic for the presence of a 1,2-disubstituted epoxide. Each of the epoxide protons was coupled to one of the other two oxymethines with a small J-value, enabling construction of a substructure corresponding to the C4-C7 unit in 1. The same unit was evident in the 1 H NMR spectrum of the diacetate, except that the signals for the oxymethine protons at C-4 and C-7 were downfield shifted from δ 5.05/5.06 to δ 6.12/6.18. The remaining two 1 H NMR signals in the spectrum of 1 corresponded to olefinic/aromatic protons that show...

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Section: Methodsmentioning

confidence: 99%

Phaeofurans and Sorbicillin Analogues from a FungicolousPhaeoacremoniumSpecies (NRRL 32148)

2006

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“…Only by evaluating each single source it is possible to filter those out. An example would be the Bisbynin [25] which is a metabolite of the fungus Stachybotrys bisbyi from seeds of Oryza sativa (see Figure 1 ).…”

Section: Resultsmentioning

confidence: 99%

How Large Is the Metabolome? A Critical Analysis of Data Exchange Practices in Chemistry

2009

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BackgroundCalculating the metabolome size of species by genome-guided reconstruction of metabolic pathways misses all products from orphan genes and from enzymes lacking annotated genes. Hence, metabolomes need to be determined experimentally. Annotations by mass spectrometry would greatly benefit if peer-reviewed public databases could be queried to compile target lists of structures that already have been reported for a given species. We detail current obstacles to compile such a knowledge base of metabolites.ResultsAs an example, results are presented for rice. Two rice (oryza sativa) subspecies have been fully sequenced, oryza japonica and oryza indica. Several major small molecule databases were compared for listing known rice metabolites comprising PubChem, Chemical Abstracts, Beilstein, Patent databases, Dictionary of Natural Products, SetupX/BinBase, KNApSAcK DB, and finally those databases which were obtained by computational approaches, i.e. RiceCyc, KEGG, and Reactome. More than 5,000 small molecules were retrieved when searching these databases. Unfortunately, most often, genuine rice metabolites were retrieved together with non-metabolite database entries such as pesticides. Overlaps from database compound lists were very difficult to compare because structures were either not encoded in machine-readable format or because compound identifiers were not cross-referenced between databases.ConclusionsWe conclude that present databases are not capable of comprehensively retrieving all known metabolites. Metabolome lists are yet mostly restricted to genome-reconstructed pathways. We suggest that providers of (bio)chemical databases enrich their database identifiers to PubChem IDs and InChIKeys to enable cross-database queries. In addition, peer-reviewed journal repositories need to mandate submission of structures and spectra in machine readable format to allow automated semantic annotation of articles containing chemical structures. Such changes in publication standards and database architectures will enable researchers to compile current knowledge about the metabolome of species, which may extend to derived information such as spectral libraries, organ-specific metabolites, and cross-study comparisons.

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“…While the reverse side of the colony remains black all the time, secondary mycelium, most often white in color, may develop on the obverse [54]. Mentioned ability to form dark pigmented structures of mycelium, specifically rich in 1,8-dihydroxynaphthalene (DHN) melanin, is typical for members of the Stachybotrys genus with the exception of Stachybotrys bisby, which forms hyaline mycelia and conidia and can be found on Oryza sativa [55]. Moreover, for S. chartarum, a specific feature is the ability to produce extracellular dark pigment on a Czapek yeast extract agar (CYA) and MEA medium, respectively [34,56].…”

Section: Species Descriptionmentioning

confidence: 99%

Update on Stachybotrys chartarum—Black Mold Perceived as Toxigenic and Potentially Pathogenic to Humans

Dyląg

Spychała

Zielinski

et al. 2022

Biology

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In nature, there are many species of fungi known to produce various mycotoxins, allergens and volatile organic compounds (VOCs), as well as the commonly known etiological agents of various types of mycoses. So far, none of them have provoked so much emotion among homeowners, builders, conservators, mycologists and clinicians as Stachybotrys chartarum. This species compared to fungi of the genera Fusarium and Aspergillus is not as frequently described to be a micromycete that is toxigenic and hazardous to human and animal health, but interest in it has been growing consistently for three decades. Depending on the authors of any given review article, attention is focused either on the clinical aspects alongside the role of this fungus in deterioration of biomaterials, or aspects related to its biology, ecology and taxonomic position. On the one hand, it is well established that inhalation of conidia, containing the highest concentrations of toxic metabolites, may cause serious damage to the mammalian lung, particularly with repeated exposure. On the other hand, we can find articles in which authors demonstrate that S. chartarum conidia can germinate and form hyphae in lungs but are not able to establish an effective infection. Finally, we can find case reports that suggest that S. chartarum infection is linked with acute pulmonary hemorrhage, based on fungal structures recovered from patient lung tissue. New scientific reports have verified the current state of knowledge and note that clinical significance of this fungus is exceedingly controversial. For these reasons, understanding S. chartarum requires reviewing the well-known toxigenic features and harmful factors associated with this fungus, by gathering the newest ones into a coherent whole. The research problem related to this fungus seems to be not overly publicized, and there is still a demand to truthfully define the real threats of S. chartarum and phylogenetically related species. The most important problem, which should be fully elucidated as soon as possible, remains the clarification of the pathogenicity of S. chartarum and related species. Maybe it is urgent time to ask a critical question, namely what exactly do we know 28 years after the outbreak of pulmonary hemorrhage in infants in Cleveland, Ohio, USA most likely caused by S. chartarum?

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Bisbynin, a novel secondary metabolite from the fungus Stachybotrys bisbyi (Srinivasan) Barron

Cited by 10 publications

References 10 publications

Phaeofurans and Sorbicillin Analogues from a FungicolousPhaeoacremoniumSpecies (NRRL 32148)

Phaeofurans and Sorbicillin Analogues from a FungicolousPhaeoacremoniumSpecies (NRRL 32148)

How Large Is the Metabolome? A Critical Analysis of Data Exchange Practices in Chemistry

Update on Stachybotrys chartarum—Black Mold Perceived as Toxigenic and Potentially Pathogenic to Humans

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