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.

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.

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.

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.

Maleic anhydride and chromone derivatives from the endophytic fungus BCC 54265 (Botryosphaeriaceae).

A maleic anhydride derivative, botryoanhydride (1), and a chromone derivative, botryochromone (2), together with three known chromones, eugenitin (3), 6-hydroxymethyleugenin (4) and 6-methoxymethyleugenin (5), were isolated from cultures of the endophytic fungus BCC 54265 of the family Botryosphaeriaceae. The structures were elucidated on the basis of NMR, HRMS and CD data. Compound 2 showed weak cytotoxic activity to cancer cell-lines.

Hirsutane Sesquiterpenes from Cultures of the Basidiomycete Marasmiellus sp. BCC 22389.

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.

Prenylhydroquinone-Derived Secondary Metabolites from Cultures of the Basidiomycete Lentinus similis BCC 52578.

Two new prenylhydroquinone-derived compounds, Ientinospirol (1) and 1-(2,5-dihydroxyphenyl)-4-hydroxy-3-methyl-l-butanone (2), were isolated from cultures of the basidiomycete Lentinus similis BCC 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 3 and 4 exhibited cytotoxicity against all cell-lines tested, while the other compounds were inactive.

Bioactive anthraquinone dimers from the leafhopper pathogenic fungus Torrubiella sp. BCC 28517.

Torrubiellins A (1) and B (2), two new dimeric anthraquinones were isolated from the leafhopper pathogenic fungus Torrubiella sp. BCC 28517. The structures of the new compounds were elucidated by analyses of the NMR spectroscopic and mass spectrometry data.

Pimarane diterpenes from the endophytic fungus Eutypella sp. BCC 13199.

Two new pimarane-type diterpenes, eutypellones A (1) and B (2), were isolated from the endophytic fungus Eutypella sp. BCC 13199. Cytotoxic activities of the pimaranes 1-5, isolated from this fungus, were evaluated.

Bioactive compounds from the scale insect pathogenic fungus Conoideocrella tenuis BCC 18627.

A new cyclohexadepsipeptide, conoideocrellide A (1), its linear derivatives, conoideocrellides B-D (2-4), three new hopane triterpenoids (5-7), two new bioxanthracenes (9 and 10), and a new isocoumarin glycoside (13) were isolated from the scale insect pathogenic fungus Conoideocrella tenuis BCC 18627. Biological activities of the new compounds were evaluated.

Gamma-lactones and ent-eudesmane sesquiterpenes from the endophytic fungus Eutypella sp. BCC 13199.

Two new gamma-lactones, eutypellins A (1) and B (2), and two ent-eudesmane sesquiterpenes, ent-4(15)-eudesmen-11-ol-1-one (3) and ent-4(15)-eudesmen-1alpha,11-diol (4), together with three known pimarane diterpenes, diaporthein B, scopararane A, and libertellenone C, were isolated from the endophytic fungus Eutypella sp. BCC 13199. The structures of these compounds were elucidated by interpretation of spectroscopic data.

Comparison of the bioactive secondary metabolites from the scale insect pathogens, Anamorph Paecilomyces cinnamomeus, and Teleomorph Torrubiella luteorostrata.

A scale insect pathogen Paecilomyces cinnamomeus BCC 9616 and its teleomorph Torrubiella luteorostrata BCC 9617, collected on the same host specimen, were fermented and chemically explored. Both fungi produced paecilodepsipeptide A (1) and zeorin (4) as major constituents of mycelia extracts. The culture broth extract of BCC 9616 provided a known diketopiperazine, terezine D (5), and a new xanthone glycoside, norlichexanthone-6-O-beta-(4-O-methylglucopyranoside) (6).

Paecilodepsipeptide A, an antimalarial and antitumor Cyclohexadepsipeptide from the insect pathogenic fungus Paecilomyces cinnamomeus BCC 9616.

Paecilodepsipeptide A (1), a new cyclohexadepsipeptide possessing three d-amino acid residues, together with its linear analogues paecilodepsipeptides B (2) and C (3), was isolated from the insect pathogenic fungus Paecilomyces cinnamomeus BCC 9616. Structures of these compounds were elucidated primarily by NMR and mass spectroscopic analyses. The absolute configurations of the amino acid and hydroxy acid residues of 1 were addressed by HPLC analysis of its acid hydrolyzate using a chiral column and Marfey's method.

Cyclohexadepsipeptides from the insect pathogenic fungus Hirsutella nivea BCC 2594.

Two new cyclohexadepsipeptides, hirsutatins A (1) and B (2), were isolated from a culture filtrate of the insect pathogenic fungus Hirsutella nivea BCC 2594. Structures of these compounds were elucidated primarily by NMR and mass spectroscopic analyses. The alpha-carbon stereochemistry of 1 was established by HPLC analysis of its acid hydrolysate using a chiral column.

A cytotoxic xanthone dimer from the entomopathogenic fungus Aschersonia sp. BCC 8401.

Ascherxanthone A (1), a novel symmetrical tetrahydroxanthone dimer, was isolated from the entomopathogenic fungus Aschersonia sp. BCC 8401. The structure of 1 was elucidated by spectroscopic analysis, especially 2D-NMR.

Unique diketopiperazine dimers from the insect pathogenic fungus Verticillium hemipterigenum BCC 1449.

[structure: see text]. Vertihemiptellides A (1) and B (2), unique diketopiperazine dimers, were isolated from the insect pathogenic fungus Verticillium hemipterigenum BCC 1449. Structures of these compounds were elucidated by NMR and mass spectral analysis, and the stereochemistry of 1 was determined by X-ray crystallography.