Chemical constituents of the toxic mold Stachybotrys chartarum

Kadirova, D. B.; Kamalov, L. S.; Бобакулов, Х. М.; Aripova, S. F.

doi:10.1007/s10600-013-0681-2

Cited by 5 publications

(3 citation statements)

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“…Mass spectrum, m / z (%): М + 485 (50), 469 (25), 454 (100), 438 (9,2), 425 (13,1), 409 (5,3), 396 (7,8), 383 (6,9), 320 (6,9), 302 (2,6), 284 (5,3), 256 (19,7), 129 (35,7), 107 (15,7), 97 (36,8), 91 (18,4), 83 (27,6), 73 (42,1), 69 (65,8), 55 (100).…”

Section: Isolation Of 133-dimethoxystachibotrinunclassified

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Low Molecular Metabolites of Fungi. 13, 3-Dimetoxystachibotrinis Stachybotrys Chartarum

Kamolov¹

2022

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Stachybotrys chartarum produces a number of low molecular weight compounds. Column chromatography of the latter isolated the nitrogen-containing compound 3-methoxystachibotrin. The structure of 13,3-dimethoxystachibotrin was established on the basis of chemical transformations using the data of ЯМР1H, 13C, 2МЯМР1H-1H, 1H -13C chemical shift correlations (COSY), long-range 1H -13C interaction (НМВС) correlation, NOE measurements in a rotating coordinate system (ROESY), IR and mass- spectra of electron impact.

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Section: Isolation Of 133-dimethoxystachibotrinunclassified

“…2. The alicyclic part of the molecule consists of 15 carbon atoms and resembles the skeleton of the dryman sesquiterpenoid [14][15][16][17][18][19][20][21][22].…”

Section: Isolation Of 133-dimethoxystachibotrinmentioning

confidence: 99%

Low Molecular Metabolites of Fungi. 13, 3-Dimetoxystachibotrinis Stachybotrys Chartarum

Kamolov¹

2022

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“…Memnoniella and Stachybotrys are two closely related fungal genera from the microbial part of this chemical space that have been extensively studied over the years for their rich endowment with a wide diversity of biologically active natural products [ 7 ]. From these two fungal genera alone, over 200 secondary metabolites of wide chemical diversity have been isolated [ 7 ], including trichothecenes [ 8 ], triprenyl phenols [ 9 ], diterpenoids [ 7 , 10 ], isochromanes [ 11 ], polyketides [ 12 ], cochlioquinones [ 13 ], cyclic peptides [ 14 ], griseofulvins [ 15 ] and others [ 16 , 17 ].…”

Section: Introductionmentioning

confidence: 99%

Antiparasitic Meroterpenoids Isolated from Memnoniella dichroa CF-080171

et al. 2023

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Memnoniella is a fungal genus from which a wide range of diverse biologically active compounds have been isolated. A Memnoniella dichroa CF-080171 extract was identified to exhibit potent activity against Plasmodium falciparum 3D7 and Trypanosoma cruzi Tulahuen whole parasites in a high-throughput screening (HTS) campaign of microbial extracts from the Fundación MEDINA’s collection. Bioassay-guided isolation of the active metabolites from this extract afforded eight new meroterpenoids of varying potencies, namely, memnobotrins C-E (1–3), a glycosylated isobenzofuranone (4), a tricyclic isobenzofuranone (5), a tetracyclic benzopyrane (6), a tetracyclic isobenzofuranone (7), and a pentacyclic isobenzofuranone (8). The structures of the isolated compounds were established by (+)-ESI-TOF high-resolution mass spectrometry and nuclear magnetic resonance spectroscopy. Compounds 1, 2, and 4 exhibited potent antiparasitic activity against P. falciparum 3D7 (EC50 0.04–0.243 μM) and T. cruzi Tulahuen (EC50 0.266–1.37 μM) parasites, as well as cytotoxic activity against HepG2 tumoral liver cells (EC50 1.20–4.84 μM). The remaining compounds (3, 5–8) showed moderate or no activity against the above-mentioned parasites and cells.

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Crystal Structure of a Cyclopentanone Oxime from the Toxic Fungus Stachybotrys Chartarum

2015

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We previously observed E-sitosterol, the hydrocarbon undecane, and a compound identified as 5-[(2-methoxyphenoxy)methyl]-1,3-oxazolidin-2-one in metabolic products from the microscopic fungus Stachybotrys chartarum [1].In continuation of research in this area, crystalline compound 1 that was unstable (hygroscopic) and deliquesced on standing was isolated from fractions obtained by chromatographic separation of total extracted substances. Its structure was established by an x-ray crystal structure analysis (XSA).Single crystals of 1 (C 5 H 9 NO) were transparent elongated plates that crystallized in the hexagonal system with a = b = 19.843(3), c = 7.796(2) A° , J = 120°, V = 2658.5(8) A° 3 , U calc = 1.115 g/cm 3 , space group P6 3 , and Z = 18. Unit-cell constants were determined and refined on an Xcalibur Ruby CCD diffractometer (Oxford Diffraction) using Cu KD-radiation (300 K, graphite monochromator). A three-dimensional dataset of reflections was obtained on the same diffractometer. Absorption corrections were applied semi-empirically using the SADABS program [2]. A high-quality XSA could not be performed because of the small amount of isolated compound and the hygroscopicity.The structure was solved by direct methods using the SHELXS-97 program suite. The structure was refined using the SHELXL-97 program [3]. All non-hydrogen atoms were refined by anisotropic full-matrix least-squares methods (over F 2 ). Positions of H atoms were found geometrically and refined with fixed isotropic thermal parameters U iso = nU eq , where n = 1.5 for methyls and 1.2 for others, and U eq is the equivalent isotropic thermal parameter of the corresponding C atoms. Hydroxyl H atoms were located in a difference electron-density synthesis and were refined isotropically. The final agreement factors (R) were 0.094 (wR2 = 0.263) over 895 reflections [I > 2V(I)] and 0.229 (wR2 = 0.321) over all 2023 reflections. The XSA data were deposited in the Cambridge Crystallographic Data Centre (CCDC No. 1042802).The XSA results showed that the isolated compound was the known cyclopentanone oxime (1). The CCDC database contains crystallographic data for its oxygen derivatives [4-6] and metal complexes [7,8] but not for the molecule itself.The asymmetric unit in the crystal included three molecules of 1 that were bound through a sequence of H-bonds between the hydroxyl of one molecule and the N atom of another (Table 1). As a result, the molecules formed a closed planar cluster with a pseudo-axis of three-fold symmetry that was perpendicular to the cluster plane (Fig. 1). The pseudo-axis was directed along the c axis (parallel to the 6 3 symmetry axis). The conformations of the three cyclopentanone rings in these molecules were different, i.e., planar, twist, and 4s D-envelope, but canonical ones that are observed in cyclopentanone oxime derivatives [4][5][6][7][8].Discrete small spherical cavities of radius 1.2 A° that repeated in steps of 0.7 A° and volumes of 12.29 A° 3 (2.7% of the total volume) formed in the crystal packing along the c axi...

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Chemical constituents of the toxic mold Stachybotrys chartarum

Cited by 5 publications

References 0 publications

Low Molecular Metabolites of Fungi. 13, 3-Dimetoxystachibotrinis Stachybotrys Chartarum

Low Molecular Metabolites of Fungi. 13, 3-Dimetoxystachibotrinis Stachybotrys Chartarum

Antiparasitic Meroterpenoids Isolated from Memnoniella dichroa CF-080171

Crystal Structure of a Cyclopentanone Oxime from the Toxic Fungus Stachybotrys Chartarum

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