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In the quest for bioactive compounds from Ganoderma , artificially cultivated fruiting bodies of Ganoderma cf. mastoporum , strain TBRC-BCC 47851 were chemically investigated. The study led to the isolation of three undescribed lanostane triterpenoids ( 1-3 ) together with twelve known compounds. The structures were elucidated on the basis of NMR spectroscopic and mass spectrometry data. The new compounds were inactive in the antimalarial and antitubercular activity assays.

Metabolites 1 and 2 , isolated from cultures of the basidiomycete Resupinatus sp. BCC84615, collected in a tropical forest in northeastern Thailand, showed weak antibiotic activity against Bacillus subtilis and Staphylococcus aureus and cytotoxicity against cancer cell lines. Their planar structures were elucidated by high-resolution electrospray ionization mass spectrometry and NMR spectroscopy as clavilactone J, known from the basidiomycete Ampulloclitocybe clavipes , and its new 1,4-benzoquinone derivative. A detailed analysis of the ROESY correlations in 1 confirmed the recent revision of the relative configuration of clavilactone J. However, specific rotation and Cotton effects observed by electronic circular dichroism were contrary to those of the clavilactones; thus, we assigned a rare antipodal absolute configuration.

Investigation of cultivated fruiting bodies of Ganoderma weberianum led to the isolation of 11 previously unreported lanostane dimers, ganoweberianones C ( 3a ), D ( 4a ), E ( 5a ), F ( 6a ), G ( 7a ), and H ( 8a ) and isoganoweberianones A ( 1b ), B ( 2b ), D ( 4b ), G ( 7b ), and H ( 8b ). Six new ganodermanontriol derivatives as three pairs of diastereomers ( 11 / 12 , 13 / 14 , and 15 / 16 ) and five new ganoweberianic acids ( 17 - 21 ) 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. Ganoweberianone D ( 4a ) and isoganoweberianone D ( 4b ) showed significant antimalarial activity against Plasmodium falciparum K1 (multidrug-resistant strain) with IC 50 values of 0.057 and 0.035 μM, respectively, whereas their cytotoxicity to Vero cells was weaker (IC 50 8.1 and 19 μM, respectively).

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 Favolaschia minutissima 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' R ,6' S by comparison of the experimental and calculated ECD data, which was correlated to the new derivative 1. These compounds exhibited antimalarial activity against Plasmodium falciparum K1 (multidrug-resistant strain). A putative minor natural product, namely 9-methoxystrobilurin P (13), was prepared by semisynthesis, which exhibited significant antimalarial activity (IC 50 0.086 μM).

Colossolactone J ( 1 ), an undescribed lanostane triterpenoid was isolated from a natural fruiting body of Ganoderma colossus 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.

Five new drimane-type sesquiterpenoids were isolated from cultures of the tropical basidiomycetes, Perenniporia centrali-africana (originating from Kenya) and Cerrena sp. nov. (originating from Thailand). A new pereniporin A derivative ( 1 ), a new drimane-type sesquiterpene lactam ( 2 ), and the new 6,7-Dehydro-isodrimenediol ( 3 ) were isolated from P. centrali-africana. In parallel, the two new drimane-type sesquiterpene lactams 5 and 6 were isolated together with known isodrimenediol ( 4 ) from Cerrena sp. This is the first report of drimane-type sesquiterpene lactams from basidiomycetes. The structures were elucidated based on 1D and 2D nuclear magnetic resonance (NMR) spectroscopic data, in combination with high-resolution electrospray mass spectrometric (HR-ESIMS) data. The compounds were devoid of significant antimicrobial and cytotoxic activities.

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. The structures were elucidated on the basis of NMR spectroscopic and mass spectrometry data. The configuration of the C-20 atom in the most abundant 20-hydroxy-lanostane, (20S,24E)-15β,20,29-trihydroxy-3,7,11-trioxolanosta-8,24-dien-26-oic acid, was established by chemical derivatization, and the absolute configuration of the lanostane skeleton was determined by ECD calculation. Two of the undescribed compounds exhibited moderate antimalarial activity., (Copyright © 2021 Elsevier Ltd. All rights reserved.)

Dry dipterocarp forests are among the most common habitat types in Thailand. Russulaceae are known as common ectomycorrhizal symbionts of Dipterocarpaceae trees in this type of habitat. The present study aims to identify collections of Russula subsection Amoeninae Buyck from dry dipterocarp forests in Thailand. A multi-locus phylogenetic analysis placed Thai Amoeninae collections in two novel lineages, and they are described here as R. bellissima sp. nov. and R. luteonana sp. nov. The closest identified relatives of both species were sequestrate species suggesting that they may belong to drought-adapted lineages. An analysis of publicly available ITS sequences in R. subsect. Amoeninae did not confirm evidence of any of the new species occurring in other Asian regions, indicating that dry dipterocarp forests might harbor a novel community of ectomycorrhizal fungi. Macromorphological characters are variable and are not totally reliable for distinguishing the new species from other previously described Asian Amoeninae species. Both new species are defined by a combination of differentiated micromorphological characteristics in spore ornamentation, hymenial cystidia and hyphal terminations in the pileipellis. The new Amoeninae species may correspond to some Russula species collected for consumption in Thailand, and the detailed description of the new species can be used for better identification of edible species and food safety in the region., (© 2022. The Author(s).)

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 0.781 μg/ml., (Copyright © 2021 Elsevier Ltd. All rights reserved.)

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. Compounds 1, 3, 5, and 7 showed moderate antimalarial activity (IC 50 3.8-7.6 μg ml -1 ).

Fourteen new compounds, oudemansins 1 - 4 , oudemansinols 5 - 7 , favolasins 8 - 10 , favolasinin ( 12 ), polyketides 13 - 15 , and ( R , E )-2,4-dimethyl-5-phenyl-4-pentene-2,3-diol ( 16 ), together with nine known compounds were isolated from the basidiomycete fungus Favolaschia sp. BCC 18686. Two new compounds, favolasin E ( 11 ) and 9-oxostrobilurin E ( 17 ), were isolated from the closely related organism Favolaschia calocera BCC 36684 along with nine β-methoxyacrylate-type derivatives. Compounds in the class of oudemansins and strobilurins exhibited moderate to strong antimalarial activity with relatively low cytotoxicity against Vero cells (African green monkey kidney fibroblasts). Potent antimalarial activity was demonstrated for 9-methoxystrobilurins G, K, and E (IC 50 values 0.061, 0.089, and 0.14 μM, respectively). The structure-activity relationships (SAR) for antimalarial activity is proposed on the basis of the activity of the new and several known β-methoxyacrylate derivatives in combination with the data from previously isolated compounds. Furthermore, several compounds showed specific cytotoxicity against NCI-187 cells (human small-cell lung cancer), although the SAR was different from that for antimalarial activity.

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. This paper also discusses structural revisions of several known derivatives. Some of the isolated compounds exhibited moderate antimalarial activity against Plasmodium falciparum K1 (IC 50 5.1-19 μM).

In a continuation of our research into antitubercular lanostane triterpenoids from submerged cultures of Ganoderma species, three strains, Ganoderma orbiforme BCC 22325, Ganoderma sp. BCC 60695, and Ganoderma australe BCC 22314, have been investigated. Fourteen new lanostane triterpenoids, together with 35 known compounds, were isolated. Antitubercular activities of these mycelium-associated Ganoderma lanostanoids against Mycobacterium tuberculosis H37Ra were evaluated. Taken together with the assay data of previously isolated compounds, structure-activity relationships of the antitubercular activity are proposed. Most importantly, 3β- and 15α-acetoxy groups were shown to be critical for antimycobacterial activity. The most potent compound was (24E)-3β,15α-diacetoxylanosta-7,9(11),24-trien-26-oic acid (35).

Nine alliacane sesquiterpenoids, inonoalliacanes A-I, were isolated from culture broth of the basidiomycete Inonotus sp. BCC 22670. The structures were elucidated on the basis of NMR spectroscopic and mass spectrometry data. The absolute configuration of inonoalliacane F was determined by application of the modified Mosher's method. Inonoalliacane A, the most abundant sesquiterpene constituent, exhibited moderate antibacterial activity against Bacillus cereus, whereas inonoalliacane B showed antiviral activity against herpes simplex virus type 1., (Copyright © 2017 Elsevier Ltd. All rights reserved.)

Two new hirsutane sesquiterpenes, marasmiellins A (1) and B (2), were isolated from cultures of the basidiomycete Marasmiellus sp. BCC 22389. The structures were elucidated on the basis of NMR spectroscopic and mass spectrometry data. The absolute configuration of marasmiellin B was determined by application of the modified Mosher's method., Competing Interests: Complianace with Ethical Standards Conflict of Interest The authors declare no conflicts of interest.

Cases of mushroom poisoning in Thailand have increased annually. During 2008 to 2014, the cases reported to the National Institute of Health included 57 deaths; at least 15 died after ingestion of amanitas, the most common lethal wild mushrooms inhabited. Hence, the aims of this study were to identify mushroom samples from nine clinically reported cases during the 7-year study period based on nuclear ITS sequence data and diagnose lethal peptide toxins using a reversed phase LC-MS method. Nucleotide similarity was identified using BLAST search of the NCBI database and the Barcode of Life Database (BOLD). Clade characterization was performed by maximum likelihood and Bayesian phylogenetic approaches. Based on BLAST and BOLD reference databases our results yielded high nucleotide similarities of poisonous mushroom samples to A. exitialis and A. fuliginea. Detailed phylogenetic analyses showed that all mushroom samples fall into their current classification. Detection of the peptide toxins revealed the presence of amatoxins and phallotoxins in A. exitialis and A. fuliginea. In addition, toxic α-amanitin was identified in a new provisional species, Amanita sp.1, with the highest toxin quantity. Molecular identification confirmed that the mushrooms ingested by the patients were members of the lethal amanitas in the sections Amanita and Phalloideae. In Thailand, the presence of A. exitialis was reported here for the first time and all three poisonous mushroom species provided new and informative data for clinical studies.

Sixteen new lanostane triterpenoids (1-16), together with 26 known compounds (17-42), were isolated from cultures of the basidiomycete Ganoderma sp. BCC 16642. Antitubercular activities of these Ganoderma lanostanoids against Mycobacterium tuberculosis H37Ra were evaluated, and structure-activity relationships are proposed.

Twelve aromadendrane sesquiterpenoids, inonotins A-L, and a previously unknown cyclofarnesane, i.e., inonofarnesane, together with two known compounds, were isolated from cultures of the wood-rotting basidiomycete Inonotus sp. BCC 23706. Inonotin I is identical to a previously reported compound with an incorrect structure. Structures of the compounds were elucidated by spectroscopic analysis and X-ray crystallography. The absolute configurations of inonotin D and inonofarnesane were determined by application of the modified Mosher's method., (Copyright © 2015 Elsevier Ltd. All rights reserved.)

Stereumins Q-U, together with known stereumins A, B, K, L, and N, as well as ent-strobilols E and G were isolated from the culture of Stereum cf. sanguinolentum BCC 22926. Their structures were elucidated by extensive spectroscopic analyses. The absolute configurations of stereumins A and Q, as well as ent-strobilol E were established by application of the modified Mosher's method. Stereumin T displayed antibacterial activity against Bacilluscereus with a MIC value of 3.97μM., (Copyright © 2014 Elsevier Ltd. All rights reserved.)

Sterostreins F-O (1-10), 10 illudalanes and norilludalanes, were isolated from cultures of the Basidiomycete Stereum ostrea BCC 22955. Their structures were elucidated by analyses of the NMR spectroscopic and mass spectrometry data. Sterostreins M (8), N (9), and O (10) are pyridine-containing illudalanes., (Copyright © 2012 Elsevier Ltd. All rights reserved.)

Sterostreins A-E (1, 2, 3a/3b, 4, and 5), five novel terpenoids, were isolated from cultures of the mushroom fungus Stereum ostrea BCC 22955. Sterostrein A (1) exhibited antimalarial activity (IC(50) 2.3 μg/mL) and cytotoxicity (IC(50) 5.3-38 μg/mL)., (© 2011 American Chemical Society)