Tyrosine oxime derivatives from the fruiting bodies of basidiomycete .

Three undescribed -prenyl-tyrosine oxime derivatives, serpulanines D-F (), were isolated from natural fruiting bodies of the basidiomycete together with serpulanine C (), and other known compounds (). The structures were elucidated based on NMR spectroscopic and mass spectrometry data. Compounds - were screened for their antibacterial activities against (MRSA and MSSA) and using the agar well diffusion method at 1 mg/mL.

Ganopyrone A, a highly rearranged lanostane triterpenoid with antimalarial activity from artificially cultivated fruiting bodies of Ganoderma colossus.

Three previously undescribed highly modified lanostane triterpenoids, ganopyrone A, ganocolossusin I, and ganodermalactone Y, were isolated from the artificially cultivated fruiting bodies of the basidiomycete Ganoderma colossus TBRC-BCC 17711. Ganopyrone A possesses an unprecedented polycyclic carbon skeleton with an α-pyrone ring and C-18/C-23 bond. It showed antimalarial activity against Plasmodium falciparum K1 (multidrug-resistant strain) with an IC value of 7.

Antimalarial 9-methoxystrobilurin derivatives from cultures of the basidiomycete Favolaschia minutissima.

Investigation of cultures of the basidiomycete Favolaschia minutissima TBRC-BCC 19434 led to the isolation of two undescribed β-methoxyacrylate metabolites, 9-methoxystrobilurins R (1) and S (2), and a degraded aldehyde derivative, favodehyde E (3). 9-Methoxystrobilurin derivatives 1 and 2 exhibited significant antimalarial activity against Plasmodium falciparum K1 (multidrug-resistant strain) with IC values of 0.12 and 0.

Fungal Depsidones Stimulate AKT-Dependent Glucose Uptake in 3T3-L1 Adipocytes.

Enhanced glucose uptake in insulin-sensitive tissues is one of the therapeutic strategies to ameliorate hyperglycemia and maintain glucose homeostasis in type 2 diabetes. This study disclosed the role of fungal depsidones in glucose uptake and the underlying mechanism in 3T3-L1 adipocytes. Depsidones, including nidulin, nornidulin, and unguinol, isolated from , stimulate glucose uptake in adipocytes.

Antimalarial Lanostane Dimers from Artificially Cultivated Fruiting Bodies of .

Investigation of cultivated fruiting bodies of led to the isolation of 11 previously unreported lanostane dimers, ganoweberianones C (), D (), E (), F (), G (), and H () and isoganoweberianones A (), B (), D (), G (), and H (). Six new ganodermanontriol derivatives as three pairs of diastereomers (/, /, and /) and five new ganoweberianic acids (-) were also isolated. A method for semisynthesis of lanostane dimers by condensation of natural lanostanes was established, which was utilized in the structure elucidation and NMR data assignments of the undescribed natural lanostane dimers.

Oudemansin and 9-methoxystrobilurin derivatives with antimalarial activity from cultures of the basidiomycete : assignments of the absolute configurations of the isoprene-derived units.

Five undescribed polyketide metabolites, oudemansins E (1), M (2), P (3), and Q (4), and 9-methoxystrobilurin I (5), were isolated from cultures of basidiomycete TBRC-BCC 19434. A γ-lactone derivative (6) of noroudemansin A (8), which was previously reported as a semisynthetic compound, was also isolated. The absolute configuration of the isoprene-derived moiety of the known cometabolite 9-methoxystrobilurin E (9) was determined to be 2',6' by comparison of the experimental and calculated ECD data, which was correlated to the new derivative 1.

Pyridylnidulin exerts anti-diabetic properties and improves non-alcoholic fatty liver disease in diet-induced obesity mice.

Non-alcoholic fatty liver disease (NAFLD) is one of the metabolic disorders related to the pathophysiology of type 2 diabetes mellitus (T2DM). Therapeutic strategies are focused on the improvement of energy balance and lifestyle modification. Additionally, the derivative of the bioactive fungal metabolite is of interest to provide health benefits, especially in obese and pre-diabetic conditions.

Chemical analysis and antitubercular activity evaluation of the dried mycelial powders of the basidiomycete Ganoderma australe TBRC-BCC 22314.

The isolation of lanostane triterpenoids possessing significant anti-tuberculosis (anti-TB) activity from mycelial cultures of the basidiomycete Ganoderma australe strain TBRC-BCC 22314 was previously reported. To demonstrate the potential of the dried mycelial powder for utilization in anti-TB medicinal products, its authentic chemical analysis was performed. Considering the possibility of the changes in the lanostane compositions and anti-TB activity by sterilization, both autoclave treated and non-autoclaved mycelial powder materials were chemically investigated.

Lanostane triterpenoids from artificially cultivated fruiting bodies of cf. .

In the quest for bioactive compounds from , artificially cultivated fruiting bodies of cf. , strain TBRC-BCC 47851 were chemically investigated. The study led to the isolation of three undescribed lanostane triterpenoids () together with twelve known compounds.

Colossolactone J, a highly modified lanostane triterpenoid from a natural fruiting body of .

Colossolactone J (), an undescribed lanostane triterpenoid was isolated from a natural fruiting body of using silica gel column chromatography and preparative HPLC. Its structure was elucidated on the basis of the spectroscopic method. The absolute configuration was determined by the combination of the modified Mosher's method and detailed NMR data analysis.

Antroxazole A, an oxazole-containing chamigrane dimer from the fungus with immunosuppressive activity.

Antroxazole A (1), a chamigrane type sesquiterpene dimer containing an oxazole moiety, has been characterized from cultures of the fungus . The structure with absolute configuration was determined by extensive spectroscopic methods and single crystal X-ray diffraction. A plausible biosynthetic pathway for 1 was proposed.

[20(22)]-Lanostane Triterpenes from the Fungus .

Twelve new lanostane triterpenoids (-, -) were isolated from the fruiting bodies of the fungus . The structures of the new compounds were elucidated by extensive 1D and 2D NMR, and HRESIMS spectroscopic analysis. All the triterpenes are featured by 20(22) configurations which are uncommon in the triterpene family.

Lanostane triterpenoids from cultivated fruiting bodies of basidiomycete Ganoderma mbrekobenum.

In the quest for medicinally active compounds in mushrooms of the genus Ganoderma, eleven undescribed lanostane triterpenoids, including a novel chlorinated derivative, i.e., (20S,24E)-21-chloro-15β,20,29-trihydroxy-3,7,11-trioxolanosta-8,24-dien-26-oic acid, were isolated from artificially cultivated fruiting bodies of the basidiomycete Ganoderma mbrekobenum.

Lanostane triterpenoids from cultivated fruiting bodies of Ganoderma sichuanense: Determination of the C-25 absolute configuration of ganoderic acid A and its derivatives using the phenylglycine methyl ester (PGME) method.

Three undescribed lanostane triterpenoids, together with twenty-one known compounds, were isolated from artificially cultivated fruiting bodies of the basidiomycete Ganoderma sichuanense. The absolute configuration at C-25 of ganoderic acid A and its derivatives was determined to be 25R by application of the phenylglycine methyl ester (PGME) method. Among the isolated compounds, ganoderiol F exhibited the most potent activity against Mycobacterium tuberculosis H37Ra with an MIC value of 0.

Semisynthetic modifications of antitubercular lanostane triterpenoids from Ganoderma.

Antitubercular lanostane triterpenoids isolated from mycelial cultures of the basidiomycete Ganoderma australe were structurally modified by semisynthesis. One of the synthetic compounds, named GA003 (9), showed more potent activity against Mycobacterium tuberculosis H37Ra than the lead natural lanostane (1). GA003 was also significantly active against the virulent strain (H37Rv) as well as extensively drug-resistant tuberculosis strains.

Furan Derivatives and Polyketides from the Fungus Irpex lacteus.

Eight new furan derivatives, irpexins A‒H (1‒8), two new polyketides, irpexins I and J (9 and 10), together with nine known compounds were isolated from the fermentation of Irpex lacteus. The structures and absolute configurations were elucidated on the basis of extensive spectroscopic methods and Mosher ester reaction. All compounds shows no cytotoxicity to human MCF-7 and Hela cancer cell lines at the concentration of 10 μM.

Limonoids from fruiting bodies of the wood-rot basidiomycete Fulvifomes xylocarpicola associated with the mangrove tree Xylocarpus granatum.

Three previously undescribed limonoids, fulvifomins A-C, together with two known compounds, 6-deoxydetigloyl-swietenine acetate and methyl angolensate, were isolated from fruiting bodies of the wood-rot fungus Fulvifomes xylocarpicola (Hymenochaetaceae), growing on the mangrove tree Xylocarpus granatum (Meliaceae). The structures were elucidated on the basis of NMR spectroscopic and mass spectrometry data, and X-ray crystallographic analysis (for fulvifomin A). A number of similar limonoids have been isolated from higher plants of the family Meliaceae, including X.

Ganoweberianones A and B, Antimalarial Lanostane Dimers from Cultivated Fruiting Bodies of the Basidiomycete .

Two lanostane dimers, ganoweberianones A () and B (), together with seven previously undescribed lanostanes, ganoweberianic acids A-G (-), and three known compounds (-), were isolated from the artificially cultivated fruiting bodies of the basidiomycete . Ganoweberianone A () exhibited significant antimalarial activity against K1 (multidrug-resistant strain) with an IC value of 0.050 μM.

Antimalarial lanostane triterpenoids from cultivated fruiting bodies of the basidiomycete Ganoderma sp.

Ten previously undescribed lanostane-type triterpenoids (1-10), together with 15 known lanostanes, were isolated from artificially cultivated fruiting bodies of the basidiomycete Ganoderma sp. BCC 21329. The structures were elucidated on the basis of NMR spectroscopic and mass spectrometry data and by application of the modified Mosher's method.

Highly Modified Lanostane Triterpenes from the Wood-Rot Basidiomycete : Comparative Chemical Investigations of Natural and Artificially Cultivated Fruiting Bodies and Mycelial Cultures.

The wood-rot basidiomycete has been chemically investigated. Comparative analyses of the natural fruiting body, artificially cultivated fruiting bodies, and mycelial cultures resulted in the isolation, in total, of 13 new highly modified lanostanes, ganocolossusins A-H (-) and ganodermalactones T-X (-), together with 23 known compounds (-). There were significant overlaps of the same compounds among the three different states of the fungal materials.

Antimalarial 9-Methoxystrobilurins, Oudemansins, and Related Polyketides from Cultures of Basidiomycete Species.

Fourteen new compounds, oudemansins -, oudemansinols -, favolasins -, favolasinin (), polyketides -, and (,)-2,4-dimethyl-5-phenyl-4-pentene-2,3-diol (), together with nine known compounds were isolated from the basidiomycete fungus sp. BCC 18686. Two new compounds, favolasin E () and 9-oxostrobilurin E (), were isolated from the closely related organism BCC 36684 along with nine β-methoxyacrylate-type derivatives.

Lanostane triterpenoids from cultivated fruiting bodies of the wood-rot basidiomycete Ganoderma casuarinicola.

Sixteen previously undescribed lanostane-type triterpenoids (1-16), together with fourteen known compounds, were isolated from cultivated fruiting bodies of the basidiomycete Ganoderma casuarinicola, a recently described species. The structures were elucidated on the basis of NMR spectroscopic and mass spectrometry data. Two of these compounds, 9 and 10, showed antimalarial activity with IC values of 9.

Acetylenic sesquiterpenoids from cultures of the basidiomycete cf. BCC 26597.

A new acetylenic sesquiterpenoid, stereyne A (), and its acetonide derivative, stereyne B (), were isolated from cultures of the basidiomycete cf. BCC 26597. The structures were elucidated by spectroscopic analysis and a chemical correlation.

Highly Modified Lanostane Triterpenes from Fruiting Bodies of the Basidiomycete Tomophagus sp.

Thirty-one highly modified lanostanes (1-31), together with 19 known compounds (32-50), were isolated from fruiting bodies of the wood-rot basidiomycete Tomophagus sp. The structures were elucidated by analyses of HRMS and NMR spectroscopic data. The present work demonstrates the high structural diversity of modified lanostane triterpenoids from Tomophagus.