Bulgaria Inquinans Research Articles

Total Synthesis of Bulgarein

AbstractHere we report an efficient and short total synthesis of bulgarein (1), a natural compound from Bulgaria inquinans with cytotoxic activity. Key steps in the total synthesis are a Suzuki‐Miyaura coupling reaction of two substituted naphthalene derivates followed by a polyphosphoric acid (PPA) mediated condensation reaction to form the benzo[j]fluoranthene skeleton. Bulgarein (1) was achieved over 4 steps with an overall yield of 25 %.

Species of fungi recommended for inclusion in the 2nd edition of the Red Data Book of the Oryol Region

Based on the results of the long-term (2008–2020) studies of macromycetes in Oryol Region, a list of 24 fungal species recommended for the second edition of the regional Red Data Book has been compiled. The list includes 4 species of basidial fungi (Clavariadelphus pistillaris, Cortinarius violaceus, Grifola frondosa, and Gyroporus cyanescens) that were included in the first edition of the Red Data Book of Oryol Region (2007) and another 20 species (Aeruginoscyphus sericeus, Bulgaria inquinans, Clavaria zollingeri, Ganoderma lucidum, Gloiodon strigosus, Gyroporus castaneus, Hericium coralloides, Holwaya mucida, Hydnocristella himantia, Metuloidea murashkinskyi, Phellinidium ferrugineofuscum, Polyporus umbellatus, Ramaria fennica, Ramariopsis crocea, Ramariopsis pulchella, Rhizochaete sulphurina, Rhodonia placenta, Rhodotus palmatus, Skeletocutis odora, Triblidium caliciiforme) that are proposed for protection for the first time. Each species is provided with the Latin name, followed by brief characteristics of its current taxonomic position, biology and ecology, population‐limiting factors in the region, data on the range in Russia and on the distribution in Oryol Region, as well as the recommended protection category. The presented species list includes two species (Clavaria zollingeri, Rhodotus palmatus) from the IUCN Red List of Threatened Species and three species (Ganoderma lucidum, Grifola frondosa, Polyporus umbellatus) recorded in the Red Data Book of the Russian Federation (2008). Two species (Aeruginoscyphus sericeus and Rhodotus palmatus) are new to Oryol Region.

Mushroom Bulgaria inquinans Modulates Host Immunological Response and Gut Microbiota in Mice.

We aimed to determine the prebiotic impact of Mushroom Bulgaria inquinans (BI) on the host immune response and gut microbiota. Male C57BL/6 mice were fed a diet supplemented with 0, 1, or 2% BI for 4 wks. Compared to mice fed with a control diet (0% BI), mice fed with 1 or 2% BI had an increase of T cell proliferation from the spleen, but such change was not found between 1 and 2% BI treated mice. Also, BI at 2% increased the production of IL-2 of splenocytes stimulated with T-cell mitogens, but BI at 1 and 2% did not affect productions of other splenic-T cell cytokines including IL-4, IL-10, and IFN-γ. Interestingly, BI at 1 or 2% inhibited T cell proliferation of mesenteric lymph node (mLN) but this effect was not found between 1 and 2% BI treated mice. Furthermore, BI inhibited the production of IL-2 in anti-CD3/CD28-stimulated T cells from mLN in a dose-dependent manner. Meanwhile, BI at 2%, not 1% inhibited the production of IL-4, IL-10, and IFN-γ of mLN. Since BI at 2% produced a more significant effect on the immune response, we further used BI at 2% to evaluate the effect of BI on gut microbiota. Of note, BI reduced the diversity of gut microbiota and resulted in an increase of Faecalibaculum and Parabacteroides abundance and the decrease of Allobaculum, Candidatus_Saccharimonas, and Rikenella abundance at the genus level. Finally, the correlation was observed between specific bacteria genera and the productions of T-cell cytokines from mesenteric lymphocytes: Rikenella and Candidatus_Saccharimonas correlated positively with IL-2, IL-4, IL-10, and IFN-γ; Bacteroides and Parabacteroides correlated negatively with IL-2 and IL-4; Faecalibaculum correlated negatively with IFN-γ and IL-4 and Bacteroides and Bifidobacterium correlated negatively with IFN-γ. The specific role of each intestinal microbiota observed is still unclear, but BI might exert a prebiotic effect on gut microbiota by increasing the abundance of potentially beneficial bacteria (Faecalibaculum). This is helpful for further demonstrating the healthy-promotion mechanism of B. inquinans.

Catálogo de la micobiota del Complejo Volcánico de Colima, México

Antecedentes y Objetivos: El Complejo Volcánico de Colima (CVC) forma parte del Eje Volcánico Transversal Mexicano, localizado en el sureste de Jalisco y norte de Colima. Comprende cinturones de vegetación que cambian a través de un gradiente altitudinal desde 1200 hasta poco más de 4000 m, en donde es posible observar bosques tropicales, bosques templados y zonas semiáridas, así como bosque mesófilo de montaña. Respecto a estudios previos sobre diversidad fúngica en esta región, solo se contaba con la cita de 140 especies registradas en los diferentes municipios que comprende el área del CVC. El objetivo del presente trabajo es actualizar el conocimiento de la micobiota registrada dentro de la zona de estudio.Métodos: Se recolectaron ejemplares fúngicos durante los meses de junio a octubre entre 2011 y 2018. Adicionalmente, se realizó la revisión de material de la colección micológica del herbario IBUG. El estudio macro y micromorfológico se realizó con las técnicas convencionales en micología y el uso de bibliografía especializada para la determinación del material.Resultados clave: Un total de 2082 ejemplares fueron determinados hasta especie, corresponden a 408 taxones; de ellos 360 son Basidiomycota y 48 Ascomycota. Se citan dos registros nuevos para la micobiota de México: Ductifera exidioidea y Psathyrella longistriata, y 11 para el estado de Jalisco: Bulgaria inquinans, Crepidotus applanatus, Gymnopilus sapineus, Hohenbuehelia spathulata, Hygrocybe spadicea, Inocybe obsoleta, Lepiota cristata, Pholiota lubrica, Rhizina undulata, Scleroderma aff. pseudostipitatum y Trichoderma alutaceum, mientras que para el estado de Colima se aportan 20 registros nuevos.Conclusiones: Se considera importante incrementar estudios sistemáticos y exploraciones micológicas que permitan conocer más sobre este recurso, su posible uso y manejo racional, así como el análisis de especies endémicas o en riesgo y aspectos ecológicos que puedan mostrar la distribución actual y diversidad fúngica en dicha región.

Expanding the chemical diversity of an endophytic fungus Bulgaria inquinans, an ascomycete associated with mistletoe, through an OSMAC approach.

An endophytic fungus Bulgaria inquinans (isolate MSp3-1), isolated from mistletoe (Viscum album), was subjected to fermentation on solid Czapek medium. Chromatographic workup of the crude EtOAc extract yielded five new natural products (1–5). Subsequent application of the “One Strain, MAny Compounds” (OSMAC) strategy on this strain by the addition of a mixture of salts (MgSO4, NaNO3 and NaCl) to solid Czapek medium induced the accumulation of nine additional new secondary metabolites (6–13, 16), with most of them (8, 10–12) not detectable in cultures lacking the salt mixture. The structures of the new compounds were established on the basis of the 1D/2D NMR and HRESIMS data. The TDDFT-ECD method was applied to determine the absolute configurations of the new compounds 1, 4 and 6 as well as of the previously reported bulgarialactone B (14), for which the absolute configuration was unknown so far. The modified Mosher's method was performed to assign the absolute configurations of 12 and 13. TDDFT-ECD analysis also allowed determining the absolute configuration of (+)-epicocconone, which had an enantiomeric absolute configuration in the tricyclic moiety compared to that of bulgarialactone B (14). All the isolated metabolites were evaluated for their cytotoxic activity. Compound 2 was found to possess strong cytotoxic activity against the murine lymphoma cell line L5178Y with an IC50 value of 1.8 μM, while the remaining metabolites were shown to be inactive.

Structures of (1 → 6)-β-d-glucans from Bulgaria inquinans (Fries) and their immunological activities

In previous study, an unbranched (1→6)-β-d-glucan with Mw 2.6kDa was isolated from fruit bodies of Bulgaria inquinans (Fries). In present paper, three branched (1→6)-β-d-glucans were obtained from the water-extracted residues by a sequential KOH-extraction, namely BIK2, BIK10 and BIK30. Their molecular weights were determined to be 37.5kDa (BIK2), 288.9kDa (BIK10) and 175.5kDa (BIK30). Structural analysis indicated that their backbones were substituted by single glucosyls at C-3 positions, the branching ratios were 0.01 (BIK2), 0.17 (BIK10), 0.25 (BIK30). Immunological tests showed that all the four β-d-glucans could significantly increase the ConA or LPS-induced lymphocytes proliferation in vivo. Moreover, branched (1→6)-β-d-glucans have more significantly lymphocytes proliferation activities than unbranched (1→6)-β-d-glucan, and the effect of (1→6)-β-d-glucans on lymphocytes proliferation increases along with molecular weights. The present results well enrich the structure–activity relationships of (1→6)-β-d-glucan, and indicate (1→6)-β-d-glucans from B. inquinans (Fries) are potential immunostimulating agents.

Structural elucidation and antioxidant activity of a water-soluble polysaccharide from the fruit bodies of Bulgaria inquinans (Fries)

The non-lichenized ascomycete Bulgaria inquinans (Fries), growing in the Changbai Mountain of China, has been used as medicinal diet for many years. In a previous study, we have reported that a heteropolysaccharide BIWS-4b from the fruit bodies of B. inquinans (Fries) exhibited markedly antimalarial and immunostimulating activities. In this paper, the structural features and antioxidant activity of BIWS-4b were investigated. The results showed that BIWS-4b contains an α-(1→2), (1→6)-mannan core to which the glucogalactan chains are attached. The glucogalactan chains were composed of (1→6)-, (1→5)- and (1→5,6)-linked β-Galf, (1→4)-linked and non-reducing terminal β-Glcp units, and might be attached to the mannan core at the O-2 positions of α-Manp units. The antioxidant assays showed that BIWS-4b exhibited good activities, including free radicals scavenging effects, ferrous ion-chelating ability and reducing power. Thus, BIWS-4b could be used as a natural antioxidant agent for food and pharmaceutical industries.

Structural characterization and immunostimulatory activity of a novel linear α-(1 → 6)-D-glucan isolated from Panax ginseng C. A. Meyer

Panax ginseng C. A. Meyer is a well-known plant medicine in the world. Ginseng polysaccharides mainly contain starch-like glucan and pectin. In this paper, a novel glucan WGPA-UH-N1 was purified from ginseng pectin by the treatment of de-esterification and endo-polygalacturonase, followed by the chromatographies on DEAE-Sepharose Fast Flow and Sephadex G-50 column. WGPA-UH-N1 has molecular weight about 17 kDa. WGPA-UH-N1 was determined to be a linear α-(1→6)-D-glucan without side chains by FT-IR, (13)C-NMR, (1)H-NMR, HMQC and HMBC spectra. It is the first time to isolate a linear α-(1→6)-D-glucan from Panax ginseng C. A. Meyer. Immunological activity assays showed that WGPA-UH-N1, although not effective on the phagocytosis of macrophage, could significantly induce lymphocyte proliferation without mitogenic stimuli at 1.0 mg/mL or with LPS at 0.5 mg/mL, also significantly increase NO production at the range of 0.1-1.0 mg/mL in a dose-dependent manner. The immunological activities of WGPA-UH-N1 are different from those of the β-(1→6)-D-glucan (BIWP2) isolated from the fruit bodies of Bulgaria Inquinans (Fries).

A Water‐Soluble Polysaccharide from the Fruit Bodies of Bulgaria inquinans (Fries) and Its Anti‐Malarial Activity

A water-soluble polysaccharide (BIWS-4b) was purified from the fruit bodies of Bulgaria inquinans (Fries). It is composed of mannose (27.2%), glucose (15.5%) and galactose (57.3%). Its molecular weight was estimated to be 7.4 kDa (polydispersity index, Mw/Mn: 1.35). Structural analyses indicated that BIWS-4b mainly contains (1 → 6)-linked, (1 → 5)-linked and (1 → 5,6)-linked β-Galf units; (1 → 4)-linked and non-reducing terminal β-Glcp units; and (1 → 2)-linked, (1 → 6)-linked, (1 → 2,6)-linked and non-reducing terminal α-Manp units. When examined by the 4-day method and in a prophylactic assay in mice, BIWS-4b exhibited markedly suppressive activity against malaria while enhancing the activity of artesunate. Immunological tests indicated that BIWS-4b significantly enhanced macrophage phagocytosis and splenic lymphocyte proliferation in malaria-bearing mice and normal mice. The anti-malarial activity of BIWS-4b might be intermediated by enhancing immune competence and restoring artesunate-suppressed immune function. Thus, BIWS-4b is a potential adjuvant of anti-malaria drugs.

A novel water-soluble β-(1→6)- d-glucan isolated from the fruit bodies of Bulgaria inquinans (Fries)

A low molecular-weight polysaccharide named BIWP2 was purified from the fruit bodies of Bulgaria Inquinans (Fries) via hot-water extraction, followed by freeze-thawing and gel filtration chromatography on Sephadex G-75. Monosaccharide composition analysis revealed that BIWP2 contained exclusively glucose. High performance size exclusion chromatography (HPSEC) showed that it was a homogeneous polysaccharide fraction. Its molecular weight was estimated to be 2.6 KD and the polydispersity index ( M w/ M n) was calculated to be 1.4. Periodate oxidation, methylation, and NMR analyses indicated that BIWP2 was a linear β-(1→6)- d-glucan without side chains. This is the first time to report a linear β-(1→6)- d-glucan with low molecular weight in non-lichenized ascomycete.

Antibacterial constituents from fruit bodies of AscomyceBulgaria inquinans

Two ergosterins and two triterpenoids were isolated from the dried fruit bodies of Ascomyce Bulgaria inquinans. By means of chemical (hydrolysis) and spectroscopic methods (NMR, El-MS), their structures were established as betuinic acid (1), cerevisterol (2), (24R)ergosta-7, 22E-diene-3beta, 5alpha, 6beta-triol-3-O-palmitate (3) and ursolic acid (4). Compound 3 is a new compound.

Antipruritic and Antierythema Effects of Ascomycete Bulgaria inquinans Extract in ICR Mice

The effect of ethanol extract obtained from Bulgaria inquinans on the scratching behavior and vascular permeability changes induced by compound 48/80, histamine and serotonin in ICR mice was studied. The extract dose-dependently inhibited scratching behavior induced by compound 48/80 and serotonin. A significant inhibition was observed at doses of 300 and 600 mg/kg when Bulgaria inquinans extract was administered orally. However, no inhibitory effect was observed on the histamine-induced scratching behavior by the extract, even at a dose of 600 mg/kg. In addition, it also inhibited the increase in the vascular permeability induced by compound 48/80 and serotonin at doses of 300 and 600 mg/kg; however, it failed to inhibit the increased vascular permeability induced by histamine, even at a dose of 600 mg/kg. Bulgaria inquinans extract showed a potent inhibitory effect on histamine release induced by compound 48/80. These results suggest that Bulgaria inquinans extract is effective in cutaneous pruritus and erythema, which were probably mediated by inhibiting the release of histamine from mast cells and antagonizing the effect on serotonin.

Novel Bioactive Azaphilones from Fruit Bodies and Mycelial Cultures of the Ascomycete Bulgaria inquinans (Fr.)

Abstract Three new azaphilones, bulgarialactone A (1), B (2) and C (3), were isolated from both the mycelia and fruit bodies of the Ascomycete Bulgaria inquinans. Bulgarialactone A (1) and B (2) possess antimicrobial, cytotoxic and nematicidal activities, and inhibit the binding of 3H-SCH 23390 to the dopamine D1 receptor. The isolation, structure determination and biological activities of the bulgarialactones are reported.

Hyphal and conidial germination of ascospores in Bulgaria inquinans and of basidiospores in Ditiola peziziformis

In Bulgaria inquinans, in which there are two types of ascospore in the ascus, the ascospore germinates either by a single, long germ-tube or with the production of conidia. The larger, pigmented spores exhibit lateral germination, but the smaller, hyaline spores germinate terminally. On virgin MA both types produce mainly germ-tubes, the hyaline spores giving a higher percentage germination. Under the immediate influence of a mature parent mycelium, the larger spores rarely germinate, but many of the smaller ones germinate to produce conidia. The development of blastoconidia and arthroconidia in culture is also described. In Ditiola peziziformis well-scattered basidiospores on MA germinate by hyphal germtubes, but close to a mature parent colony only conidia are formed.

Constituents of the higher fungi. Part XVI. Bulgarhodin and Bulgarein, novel benzofluoranthenequinones from the fungus Bulgaria inquinans(Fries)

Three crystalline quinones have been isolated from the fungus Bulgaria inquinans. Two of these have been identified as derivatives of benzo[j]fluoranthene and the third characterised as 4,9-dihydroxyperylene-3,10-quinone. This is the first recorded isolation of a natural product with structure based on the benzofluoranthene nucleus.

Jelly as a water-reserve in fungi

In Bulgaria inquinans spore discharge continues even when the drying gelatinous apothecium has lost four-fifths of its original weight. In Phallus impudicus evidence is given that the rapid elongation of the stalk involves a considerable increase in weight. In both these fungi the fruit-body is richly supplied with jelly. It is suggested that this represents a water reserve used for spore discharge in the first species and for stipe elongation in the other.

Ascospore Dimorphism of Bulgaria inquinans, Fr

THE adult ascus of Bulgaria inquinans typically contains eight spores, four of which are large, dark and thick-walled, the rest being small, thin-walled and hyaline.