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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. [ABSTRACT FROM AUTHOR]

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. [ABSTRACT FROM AUTHOR]

A new acetylenic sesquiterpenoid, stereyne A (1), and its acetonide derivative, stereyne B (2), were isolated from cultures of the basidiomycete Stereum cf. hirsutum BCC 26597. The structures were elucidated by spectroscopic analysis and a chemical correlation. Their absolute configurations were determined by application of the modified Mosher's method. They represent new structural type of sesquiterpenoids from Stereum. [ABSTRACT FROM AUTHOR]

A new lanostane triterpene (1), together with three known compounds (2-4), were isolated from cultivated fruiting bodies of the basidiomycete Ganoderma australe. The structure was elucidated on the basis of NMR spectroscopic and mass spectrometry data. The olefinic geometry of methyl australate (2) was revised from 20(22)Z to 20(22)E. These compounds (1-4) were different from the lanostanes isolated from mycelial cultures of the same strain source. [ABSTRACT FROM AUTHOR]

A new seco-tremulane, 11,12-epoxy-5,6-secotremula-1,6(13)-dien-5,12-olide ( 1), was isolated together with the known compounds, conocenolides A ( 2) and B ( 3), tremulenediol A ( 4), tremulenolide A ( 5), and two lanostane triterpenoids, trametenolic acid B ( 6), and pinicolic acid A ( 7), from cultures of the basidiomycete Flavodon flavus BCC 17421. Interconversion of conocenolides A/B was demonstrated. Compound 1 exhibited weak cytotoxic activities, whereas tremulenediol A showed antiplasmodial activity ( IC50 8.6 μg/ml). Pinicolic acid A exhibited activity against herpes simplex virus type-1 ( IC50 15 μg/ml) as well as cytotoxic activities. [ABSTRACT FROM AUTHOR]

The wood-rot basidiomycete Ganoderma colossus 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 ( 1 - 8 ) and ganodermalactones T-X ( 9 - 13 ), together with 23 known compounds ( 14 - 36 ). There were significant overlaps of the same compounds among the three different states of the fungal materials. Ganocolossusin D ( 4 ) displayed the most potent antimalarial activity against Plasmodium falciparum K1 (multi-drug-resistant strain) with an IC 50 value of 2.4 μM, while it was noncytotoxic to Vero cells at 50 μg/mL.

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.

A new lanostane triterpene (1), together with three known compounds (2-4), were isolated from cultivated fruiting bodies of the basidiomycete Ganoderma australe. The structure was elucidated on the basis of NMR spectroscopic and mass spectrometry data. The olefinic geometry of methyl australate (2) was revised from 20(22)Z to 20(22)E. These compounds (1-4) were different from the lanostanes isolated from mycelial cultures of the same strain source.

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).

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.