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The wood-rot basidiomycete Ganoderma colossushas 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 falciparumK1 (multi-drug-resistant strain) with an IC50value of 2.4 μM, while it was noncytotoxic to Vero cells at 50 μg/mL.

In a continuation of our research into antitubercular lanostane triterpenoids from submerged cultures of Ganodermaspecies, three strains, Ganoderma orbiformeBCC 22325, Ganodermasp. BCC 60695, and Ganoderma australeBCC 22314, have been investigated. Fourteen new lanostane triterpenoids, together with 35 known compounds, were isolated. Antitubercular activities of these mycelium-associated Ganodermalanostanoids against Mycobacterium tuberculosisH37Ra 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).

Two new hirsutane sesquiterpenes, marasmiellins A (1) and B (2), were isolated from cultures of the basidiomycete Marasmiellussp. 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.

Sixteen new lanostane triterpenoids (1–16), together with 26 known compounds (17–42), were isolated from cultures of the basidiomycete Ganodermasp. BCC 16642. Antitubercular activities of these Ganodermalanostanoids against Mycobacterium tuberculosisH37Ra were evaluated, and structure–activity relationships are proposed.

Seven new lanostane-type triterpenes, hypocrellols A–G (1–7), and six new hopane-type triterpenes, 7β,15α-dihydroxy-22(29)-hopene (8), 3β,7β-dihydroxy-22(29)-hopene (9), 3β-acetoxy-15α-hydroxy-22(29)-hopene (10), 3β,7β,15α,22-tetrahydroxyhopane (11), 3β-acetoxy-7β,15α,22-trihydroxyhopane (12), and 7β,15α,22-trihydroxyhopane (13), were isolated from the scale insect pathogenic fungus Hypocrellasp. BCC 14524. The structures of the new compounds were elucidated by analyses of the NMR spectroscopic and mass spectrometry data. The structure of 1was confirmed by X-ray crystallography.

A novel cyclodepsipeptide, cordycommunin (1), and two dihydroisocoumarins (2and 3) were isolated from the insect pathogenic fungus Ophiocordyceps communisBCC 16475. The absolute configurations of the amino acid residues of 1were addressed by application of Marfey’s method. Cordycommunin (1) showed growth inhibition of Mycobacterium tuberculosisH37Ra with an MIC value of 15 μM. This compound also exhibited weak cytotoxicity to KB cells with an IC50of 45 μM, while it was inactive against BC, NCI-H187, and Vero cell lines at a concentration of 88 μM (50 μg/mL).

Two new prenylhydroquinone-derived compounds, lentinospirol (1)and 1-(2,5-dihydroxyphenyl)-4-hydroxy-3-methyl-1-butanone (2), were isolated from cultures of the basidiomycete Lentinus similisBCC 52578, together with the known compounds panepoxydone (3), panepoxydione (4), isopanepoxydone (5), 2,2-dimethyl-6-hydroxy-2H-chromene (6), and (3R,4S)-3,4-dihydroxy-2,2-dimethyl-6-methoxychroman (7). Compounds 3and 4exhibited cytotoxicity against all cell-lines tested, while the other compounds were inactive.