Stachybotrys Sp Research Articles

Phenylspirodrimane with Moderate Reversal Effect of Multidrug Resistance Isolated from the Deep-Sea Fungus Stachybotrys sp. 3A00409.

Two new phenylspirodrimanes, stachybotrins K and L (1 and 2), together with eight known analogues (3-10), were isolated from deep-sea-derived Stachybotrys sp. MCCC 3A00409. Their structures were determined by extensive NMR data and mass spectroscopic analysis. Absolute configurations of new compounds were determined through a comparison of their circular dichroism (CD) spectra with other reported compounds. The possible reversal effects of all compounds were assayed in the resistant cancer cell lines. Stachybotrysin B (8) can reverse multidrug resistance (MDR) in ABCB1-overexpression cells (KBv200, Hela/VCR) at the non-cytotoxic concentration. Doxorubicin accumulation assay and molecular-docking analysis reveal that the mechanism of its reversal MDR effect may be related to the increase in the intracellular concentration of substrate anticancer drugs.

Three new phenylspirodrimanes from a conch-derived fungus Stachybotrys sp. NF02434

Three new phenylspirodrimanes from a conch-derived fungus Stachybotrys sp. NF02434

Biosynthetic melanin with excellent performance can be used for heavy metal adsorption

Melanin is a complex polymer composed of indole and/or phenolic monomers, which show the potential to adsorb heavy metals in water due to their numerous functional groups. However, the artificial synthesis of melanin is difficult and the natural sources are limited. In this study, we screened the filamentous fungus Stachybotrys sp. HSS-1 to produce 11.56 g/L melanin M1 after fermentation optimization. M1 was identified as eumelanin using UV spectroscopy, elemental analysis, HPLC-MS, infrared spectroscopy, and nuclear magnetic resonance. Melanin M1 nano-materials showed the ability to adsorb the heavy metals Cd2+, Cu2+ and Pb2+ in water; in particular, the adsorption upper limit of Pb2+ reached 45 mg/g. Melanin M1 nano-materials also exhibited excellent thermal stability and radiation resistance, with a residual rate of 96.46% after heating at 100 °C for 2 h and more than 98% after 60 min of UV irradiation and 5 d of sunlight exposure. In addition, melanin M1 nano-materials strongly inhibited Staphylococcus aureus, Bacillus megaterium, and Salmonella, and the scavenging rates of 1 g/L M1 on superoxide radicals and hydroxyl radicals in the solution reached 97.33% and 98.59%, respectively. Therefore, melanin M1 nano-materials can not only adsorb heavy metals but also show the ability to resist the complex natural environment. Overall, this study developed high-yield, stable microbial melanin nano-materials that was shown to be an excellent adsorbent for heavy metal removal from water.

Insights into the Chemical Diversity of Selected Fungi from the Tza Itzá Cenote of the Yucatan Peninsula.

Cenotes are habitats with unique physical, chemical, and biological features. Unexplored microorganisms from these sinkholes represent a potential source of bioactive molecules. Thus, a series of cultivable fungi (Aspergillus spp. NCA257, NCA264, and NCA276, Stachybotrys sp. NCA252, and Cladosporium sp. NCA273) isolated from the cenote Tza Itzá were subjected to chemical, coculture, and metabolomic analyses. Nineteen compounds were obtained and tested for their antimicrobial potential against ESKAPE pathogens, Mycobacterium tuberculosis, and nontuberculous mycobacteria. In particular, phenylspirodrimanes from Stachybotrys sp. NCA252 showed significant activity against MRSA, MSSA, and mycobacterial strains. On the other hand, the absolute configuration of the new compound 17-deoxy-aspergillin PZ (1) isolated from Aspergillus sp. NCA276 was established via single-crystal X-ray crystallography. Also, the chemical analysis of the cocultures between Aspergillus and Cladosporium strains revealed the production of metabolites that were not present or were barely detected in the monocultures. Finally, molecular networking analysis of the LC-MS-MS/MS data for each fungus was used as a tool for the annotation of additional compounds, increasing the chemical knowledge on the corresponding fungal strains. Overall, this is the first systematic chemical study on fungi isolated from a sinkhole in Mexico.

IMPACTO DEL CAMBIO EN EL MANEJO DEL CULTIVO DE TRIGO DE CONVENCIONAL A ORGÁNICO SOBRE LAS COMUNIDADES FÚNGICAS CULTIVABLES DEL SUELO EN EL VALLE DEL YAQUI, MÉXICO

El uso de fertilizantes orgánicos en el Valle del Yaqui tiende a reducir la degradación del suelo en la producción de trigo, sin embargo, todavía no se han evaluado los impactos biológicos de esta práctica en el suelo. El objetivo de este experimento fue cuantificar el impacto del cambio en el manejo del cultivo de trigo, de convencional a orgánico, sobre la reducción de la degradación fúngica del suelo, por medio del análisis de sus poblaciones fúngicas cultivables y su diversidad. La hipótesis fue que la aportación de fertilizantes orgánicos al cultivo de trigo produce cambios positivos en las propiedades fisicoquímicas del suelo, lo cual beneficia a las poblaciones de hongos, y disminuye su degradación. Tres campos comerciales de trigo se seleccionaron con 1) fertilización sintética convencional (SF), 2) fertilización sintética más fertilización orgánica (SF+OF) y 3) sólo fertilización orgánica (OF). Los sitios de estudio bajo OF y SF+OF vs. SF mostraron mayores, contenidos de materia orgánica (1.5, 1.6 vs. 0.45%), población de hongos (1.7x105, 9.1x104 vs. 1.6x104 CFU g-1 de suelo seco) y diversidad (12, 12 vs. 2). Con base en el análisis filogenético, se aislaron 9, 11 y 2 géneros de hongos de los sitios de estudio bajo fertilización orgánica, sintética + orgánica y sintética, respectivamente. La diversidad metabólica de las cepas fúngicas obtenidas mostró que la producción de indoles osciló entre 0.5 y 65.4 μg mL-1; el hongo Stachybotrys sp. TSM35 fue el productor de indoles mayor. La solubilización de fosfatos mayor (21%) se observó en la cepa Talaromyces pinophilus TSO42 y la cepa con producción de sideróforos mayor (33.9%) fue Volutella ciliata TSM43. Además, el 60% de las cepas mostraron riesgos potenciales para la salud (α- o β-hemólisis). La rotación de convencional a orgánico en el cultivo del trigo logró cambios positivos en las propiedades fisicoquímicas del suelo, en la diversidad y características metabólicas de las poblaciones fúngicas cultivable. El control de la calidad microbiológica de los fertilizantes orgánicos se necesita para evitar riesgos microbiológicos en los sistemas agronómicos, causados por la introducción de cepas con potencial patogénico.

Antibacterial phenylspirodrimanes from the marine-derived fungus Stachybotrys sp. SCSIO 40434

Five new phenylspirodrimanes, stachybomycins A − E (1–5), together with four known compounds (6–9), were isolated from the marine-derived fungus Stachybotrys sp. SCSIO 40434. Their structures were elucidated by comprehensive spectroscopic analyses of NMR and HRESIMS. The absolute configuration of 1 was confirmed by single crystal X-ray diffraction analysis. Compounds 5 and 7 showed moderate antibacterial activities against Micrococcus luteus, Staphylococcus aureus and methicillin resistant Staphylococcus aureus with minimal inhibition concentration (MIC) values of 8, 16 and 16 μg mL−1, respectively.

Bioreactivity, Guttation and Agents Influencing Surface Tension of Water Emitted by Actively Growing Indoor Mould Isolates.

The secretion of metabolites in guttation droplets by indoor moulds is not well documented. This study demonstrates the guttation of metabolites by actively growing common indoor moulds. Old and fresh biomasses of indoor isolates of Aspergillus versicolor, Chaetomium globosum, Penicillium expansum, Trichoderma atroviride, T. trixiae, Rhizopus sp. and Stachybotrys sp. were compared. Metabolic activity indicated by viability staining and guttation of liquid droplets detected in young (<3 weeks old) biomass were absent in old (>6 months old) cultures consisting of dehydrated hyphae and dormant conidia. Fresh (<3 weeks old) biomasses were toxic more than 10 times towards mammalian cell lines (PK-15 and MNA) compared to the old dormant, dry biomasses, when calculated per biomass wet weight and per conidial particle. Surfactant activity was emitted in exudates from fresh biomass of T. atroviride, Rhizopus sp. and Stachybotrys sp. Surfactant activity was also provoked by fresh conidia from T. atroviride and Stachybotrys sp. strains. Water repealing substances were emitted by cultures of P. expansum, T. atroviride and C. globosum strains. The metabolic state of the indoor fungal growth may influence emission of liquid soluble bioreactive metabolites into the indoor air.

New Bisabosquals from Stachybotrys sp. PH30583 Elicited on Solid Media.

Stachybotrys sp. PH30583 cultured in liquid medium only led to one structure type of novel isochroman dimers. Using the one strain-many compounds strategy, the reinvestigation of the metabolites from Stachybotrys sp. PH30583 cultured in rice solid medium led to the isolation of four triprenyl phenols, including two new bisabosquals and two known phenylspirodrimanes. Nitrobisabosquals A and B (1 and 2) are the first case of pyrrolidone-bisabosquals reported in literature. Totally different compounds were isolated using rice solid medium, compared with those isolated using liquid medium, so that rice solid medium presents a key factor in the production of triprenyl phenols. Compound 1 exhibited cytotoxicity against tumor cells, A-549, HL-60, MCF-7 SMMC-7721, and SW480, as well as weak anticoagulant activity with activated partial thromboplastin time (APTT) of 32.1 ± 0.17 s (p < 0.05 vs. Con.) at a concentration of 5 mM. Triprenyl phenol metabolites could be used as chemotaxonomic markers for Stachybotrys.

Two new phenylspirodrimanes from the deep-sea derived fungus Stachybotrys sp. MCCC 3A00409

Two new phenylspirodrimanes, stachybotrin H (1) and stachybotrysin H (9) together with eleven known analogues (2–8, 10–13) were isolated from deep-sea derived Stachybotrys sp. MCCC 3A00409. Their structures were determined by extensive NMR data and mass spectroscopic analysis. Compounds 9–12 showed weak cytotoxicity against three human cancer cell lines K562, Hela and HL60 with IC50 in the range of 18.5–52.8 μM.

Novel Isochroman Dimers from Stachybotrys sp. PH30583: Fermentation, Isolation, Structural Elucidation and Biological Activities.

The rare anishidiol and five new isochromans, including three novel dimers with unprecedented skeletons, were isolated from Stachybotrys sp. PH30583. Their structures were determined by spectral analyses. The bioactivities of these compounds were also investigated. The dimers (6-10) inhibited acetylcholinesterase at 50 µM, but the monomers did not. To investigate the biogenesis of the novel dimers, a time-course investigation of metabolite production was undertaken.

Stachybotrysin, an Osteoclast Differentiation Inhibitor from the Marine-Derived Fungus Stachybotrys sp. KCB13F013.

Two new phenylspirodrimane derivatives, stachybotrysin (1) and stachybotrylactone B (2), were isolated from the cultures of the marine-derived fungus Stachybotrys sp. KCB13F013. The structures were determined by analyzing the spectroscopic data (1D and 2D NMR and MS) and chemical transformation, including the modified Mosher's method and single-crystal X-ray structure analysis. Compound 1 exhibited an inhibitory effect on osteoclast differentiation in bone marrow macrophage cells via suppressing the RANKL-induced activation of p-ERK, p-JNK, p-p38, c-Fos, and NFATc1.

Spirocyclic drimanes from the marine fungus Stachybotrys sp. strain MF347.

A novel spirocyclic drimane coupled by two drimane fragment building blocks 2 and a new drimane 1 were identified in mycelia and culture broth of Stachybotrys sp. MF347. Their structures were established by spectroscopic means. This is the first example of spirocyclic drimane coupled by a spirodihydrobenzofuranlactam unit and a spirodihydroisobenzofuran unit; and the connecting position being N-C instead of an N and N connecting unit. Strain MF347 produced also the known spirocyclic drimanes stachybocin A (12) and stachybocin B (11) featured by two sesquiterpene-spirobenzofuran structural units connected by a lysine residue; the known spirocyclic drimanes chartarlactam O (5); chartarlactam K (6); F1839A (7); stachybotrylactam (8); stachybotramide (9); and 2α-acetoxystachybotrylactam acetate (10); as well as ilicicolin B (13), a known sesquiterpene. The relative configuration of two known spirobenzofuranlactams (3 and 4) was determined. All compounds were subjected to biological activity tests. The spirocyclic drimane 2, 11, and 12, as well as the sesquiterpene 13, exhibited antibacterial activity against the clinically relevant methicillin-resistant Staphylococcus aureus (MRSA).

The Lactone form of stachybotrydial: a new inhibitor of dihydrofolate reductase from stachybotrys sp. FN298.

Dihydrofolate reductase (DHFR) has been confirmed to be a novel target for antibacterial drug development. In this study, we determined that a fungal metabolite from Stachybotrys sp. FN298 can inhibit the DHFR of Staphylococcus aureus. Its structure was identified as a lactone form of stachybotrydial using mass spectrometry and nuclear magnetic resonance analysis. This compound inhibited S. aureus DHFR with a half-maximal inhibitory concentration of 41 µM. It also prevented the growth of S. aureus and methicillin-resistant S. aureus (MRSA) with a minimum inhibitory concentration of 32 µg·mL(-1). To our knowledge, this is the first description of a DHFR inhibitor of microbial origin. The inhibitory function of the lactone form of stachybotrydial highlights its potential for development into a new broad-spectrum antibacterial agent and as an agent against MRSA.

Purification and biochemical characterization of a transglucosilating β-glucosidase of Stachybotrys strain

The filamentous fungus Stachybotrys sp has been shown to possess a rich beta-glucosidase system composed of five beta-glucosidases. One of them was already purified to homogeneity and characterized. In this work, a second beta-glucosidase was purified and characterized. The filamentous fungal A19 strain was fed-batch cultivated on cellulose, and its extracellular cellulases (mainly beta-glucosidases) were analyzed. The purified enzyme is a monomeric protein of 78 kDa molecular weight and exhibits optimal activity at pH 6.0 and at 50 degrees C. The kinetic parameters, K (m) and V (max), on para-nitro-phenyl-beta-D: -glucopyranosid (p-NPG) as a substrate were, respectively, 1.846 +/- 0.11 mM and 211 +/- 0.08 micromol min(-1) ml(-1). One interesting feature of this enzyme is its high stability in a wide range of pH from 4 to 10. Besides its aryl beta-glucosidase activity towards salicin, methylumbellypheryl-beta-D: -glucoside (MU-Glc), and p-NPG, it showed a true beta-glucosidase activity because it splits cellobiose into two glucose monomers. This enzyme has the capacity to synthesize short oligosaccharides from cellobiose as the substrate concentration reaches 30% with a recovery of 40%. We give evidences for the involvement of a transglucosylation to synthesize cellotetraose by a sequential addition of glucose to cellotriose.

Leaching and microbial treatment of a soil contaminated by sulphide ore ashes and aromatic hydrocarbons

Contaminated soil from a historical industrial site and containing sulfide ore ashes and aromatic hydrocarbons underwent sequential leaching by 0.5 M citrate and microbial treatments. Heavy metals leaching was with the following efficiency scale: Cu (58.7%) > Pb (55.1%) > Zn (44.5%) > Cd (42.9%) > Cr (26.4%) > Ni (17.7%) > Co (14.0%) > As (12.4%) > Fe (5.3%) > Hg (1.1%) and was accompanied by concomitant removal of organic contaminants (about 13%). Leached metals were concentrated into an iron gel, produced during ferric citrate fermentation by the metal-resistant strain BAS-10 of Klebsiella oxytoca. Concomitantly, the acidic leached soil was bioaugmented with Allescheriella sp. DABAC 1, Stachybotrys sp. DABAC 3, Phlebia sp. DABAC 9, Pleurotus pulmonarius CBS 664.97, and Botryosphaeria rhodina DABAC P82. B. rhodina was most effective, leading to a significant depletion of the most abundant contaminants, including 7-H-benz[DE]anthracene-7-one, 9,10-anthracene dione and dichloroaniline isomers, and to a marked detoxification as assessed by the mortality test with the Collembola Folsomia candida Willem. The overall degradation activities of B. rhodina and P. pulmonarius appeared to be significantly enhanced by the preliminary metal removal.

ChemInform Abstract: Novel Stachyflin Derivatives from Stachybotrys sp. RF‐7260. Fermentation, Isolation, Structure Elucidation and Biological Activities.

AbstractChemInform is a weekly Abstracting Service, delivering concise information at a glance that was extracted from about 100 leading journals. To access a ChemInform Abstract of an article which was published elsewhere, please select a “Full Text” option. The original article is trackable via the “References” option.

ChemInform Abstract: Stachyflin and Acetylstachyflin, Novel Anti‐Influenza A Virus Substances, Produced by Stachybotrys sp. RF‐7260. Part 2. Synthesis and Preliminary Structure—Activity Relationships of Stachyflin Derivatives.

AbstractChemInform is a weekly Abstracting Service, delivering concise information at a glance that was extracted from about 100 leading journals. To access a ChemInform Abstract of an article which was published elsewhere, please select a “Full Text” option. The original article is trackable via the “References” option.

ChemInform Abstract: Stachyflin and Acetylstachyflin, Novel Anti‐Influenza A Virus Substances, Produced by Stachybotrys sp. RF‐7260. Part 1. Isolation, Structure Elucidation and Biological Activities.

AbstractChemInform is a weekly Abstracting Service, delivering concise information at a glance that was extracted from about 100 leading journals. To access a ChemInform Abstract of an article which was published elsewhere, please select a “Full Text” option. The original article is trackable via the “References” option.

Stachyflin and acetylstachyflin, novel anti-influenza A virus substances, produced by Stachybotrys sp. RF-7260. II. Synthesis and preliminary structure-activity relationships of stachyflin derivatives.

Stachyflin and acetylstachyflin, produced by Stachybotrys sp. RF-7260, were found to have potent anti-influenza A virus activity. Stachyflin is a new class of hemagglutinin fusion inhibitors of influenza A virus. Several derivatives were synthesized from acetylstachyflin and subjected to preliminary examination of their structure-activity relationships. Among them, the 3-oxo and 3,8'-dioxo derivatives showed potent antiviral activity similar to stachyflin. The 3-epi derivative was four times less active than stachyflin. Modification of the 6'-hydroxy group and the C-5' position markedly diminished the antiviral activity.

Novel stachyflin derivatives from Stachybotrys sp. RF-7260. Fermentation, isolation, structure elucidation and biological activities.

Stachybotrys sp. RF-7260 was found to produce stachyflins, novel anti-influenza virus agents, under solid-state fermentation conditions. Feeding DL-lysine to a culture of Stachybotrys sp. RF-7260 induced the formation of the novel compounds, SQ-02-S-L2 and -L1, and feeding DL-valine the formation of SQ-02-S-VI and -V2. The structures of these metabolites were determined by detailed 2D NMR analyses in comparison with acetylstachyflin. SQ-02-S-L2 and -L1 have the lysine moiety and SQ-02-S-V1 has the valine moiety. SQ-02-S-V2 has an amidine moiety instead of the lactam moiety in acetylstachyflin. SQ-02-S-L2, -L1 and -V1, substituted on the lactam amide hydrogen, displayed only a low level of the antiviral activity. However, deacetyl SQ-02-S-V2 showed potent antiviral activity similar to stachyflin.