Two new 4,6-dimethyl-3,4-dihydrochromen-2-one derivatives from Craterellus odoratus.

Two rare types of 4,6-dimethyl-3,4-dihydrochromen-2-one derivatives, named cralactones A and B (1 and 2), were isolated from the culture broth of Craterellus odoratus. The structures of the new ones were established on the basis of extensive spectroscopic analysis, and it was found that the new compounds did not show pancreatic lipase inhibitory activity. Compounds 1 and 2 are the first examples of 4,6-dimethyl-3,4-dihydrochromen-2-one.

Two new compounds from Xanthium strumarium.

One new lignan, fructusol A (1), and one new thiazine derivative, 2-hydroxy-xanthiazone (2), along with eight known ones, were isolated from the seeds of Xanthium strumarium. The structures of new compounds were elucidated on the basis of extensive spectroscopic methods. Meanwhile, compounds 1-3 were tested for their antifungal activities against Candida albicans (ATCC 10231) in vitro. No one showed obvious inhibitions (MIC90 > 128 µg/ml).

A new bisabolane-type sesquiterpenoid from the fermentation broth of fungus Antrodiella gypsea.

Studies of the fermentation broth of fungus Antrodiella gypsea led to the isolation of a new bisabolane-type sesquiterpenoid that was named gypseatriol (1), together with the known compound 2,10-dodecadiene-1,6,7-triol (2). The structure of this new metabolite was assigned by analysis of 2D NMR and HR-EI-MS. Absolute configuration was assigned by single crystal X-ray diffraction analysis. Compound 1 was evaluated for its antifungal activity on Candida albicans.

Two new sesquiterpenoids from cultures of the basidiomycete Tremella foliacea.

Two new sesquiterpenoids, trefoliol B (1) and trefoliol C (2), together with known echinocidin A (3), were isolated from cultures of the basidiomycetes Tremella foliacea. The new structures were elucidated on the basis of extensive spectroscopic methods. At the same time, trefoliol B (1) and echinocidin A (3) were tested for their cytotoxicities against five human cancer cell lines and for their inhibitory activities against isozymes of 11ß-hydroxysteroid dehydrogenases (11ß-HSD). No compound showed significant activity (IC50 > 40 µM). Compound 1 showed moderate inhibitory activities against 11ß-HSD1 (human IC50 = 13.1 µM; mouse IC50 = 91.8 µM).

Lucidimine A-D, four new alkaloids from the fruiting bodies of Ganoderma lucidum.

Four new polycylic alkaloids, lucidimine A-D, were isolated from the fruiting bodies of Ganoderma lucidum. Their chemical structures were established based on 1D and 2D NMR data as well as HREIMS/HRESIMS analyses.

Three new sesquiterpenoids from cultures of the basidiomycete Conocybe siliginea.

Three new sesquiterpenoids (1-3), along with four known compounds (4-7), were isolated from cultures of the fungus Conocybe siliginea. The structures of new compounds were elucidated using spectroscopic methods. The known compounds were identified by comparing their spectroscopic data with those reported in the literature. All new compounds were evaluated for cytotoxicity against five human cancer cell lines, but none of them possesses significant activity (IC50>40µM).

Two new triterpenoids from fruiting bodies of fungus Ganoderma lucidum.

Two new triterpenoids, (24E)-9α,11α-epoxy-3ß-hydroxylanosta-7,24-dien-26-al (1) and (22Z,24Z)-13-hydroxy-3-oxo-14(13 â†’ 12)abeo-lanosta-8,22,24-trien-26,23-olide (2) were isolated from dried fruiting bodies of fungus Ganoderma lucidum. The structures of these two new compounds were elucidated on the basis of extensive spectroscopic analyses. Compound 1 possessed a lanostane skeleton, while compound 2 was based on a rare 14 (13 â†’ 12)abeo-lanostane skeleton with a 26,23-olide moiety. Both of them were evaluated for their antifungal and cytotoxic activities. Neither of them displayed obvious inhibition on Candida albicans and five human cancer cell lines.

Two new illudin type sesquiterpenoids from cultures of Phellinus tuberculosus and Laetiporus sulphureus.

Chemical investigation on the cultures of Phellinus tuberculosus and Laetiporus sulphureus lead to the isolation of two new illudin-type sesquiterpenoids (phellinuin J and sulphureuine A). Their structures were elucidated by 1D, 2D NMR and MS spectroscopic data. These compounds were purposely evaluated for their cytotoxicity against HL-60, SMMC-7721, A549, MCF-7, and SW480 cell lines.

Chemical and toxicological investigations of a previously unknown poisonous European mushroom Tricholoma terreum.

The established tradition of consuming and marketing wild mushrooms has focused attention on mycotoxicity, which has become a global issue. In the present study, we describe the toxins found in a previously unknown poisonous European mushroom Tricholoma terreum. Fifteen new triterpenoids terreolides A-F (1-6) and saponaceolides H-P (8-16) were isolated from the fruiting bodies of the toxic mushroom T. terreum. Terreolides A-C (1-3) possessed a unique 5/6/7 trioxaspiroketal system, whereas terreolides D-F (4-6) possessed an unprecedented carbon skeleton. Two abundant compounds in the mushroom, saponaceolide B (7) and saponaceolide M (13), displayed acute toxicity, with LD50 values of 88.3 and 63.7 mg kg(-1) when administered orally in mice. Both compounds were found to increase serum creatine kinase levels in mice, indicating that T. terreum may be the cause of mushroom poisoning ultimately leading to rhabdomyolysis.

Two new ylangene-type sesquiterpenoids from cultures of the fungus Postia sp.

Two new ylangene-type sesquiterpenoids, postinins A (1) and B (2), were isolated from cultures of the fungus Postia sp. Structures 1 and 2 were elucidated on the basis of extensive spectroscopic analysis. The bioactivity evaluation showed that both compounds had significant inhibitory activities against protein tyrosine phosphatase 1B, and SH2-containing cytoplasmic tyrosine phosphatase-1 and -2 with IC50 values of 1.6-6.2 µg/ml.

Four new sesquiterpenoids from fruiting bodies of the fungus Inonotus rickii.

Three new bisabolane sesquiterpenoids, inonotic acid A (1), 3-O-formyl inonotic acid A (2), inonotic acid B (3), and one new drimane sesquiterpenoid 3α,6ß-dihydroxycinnamolide (4), were isolated from the fruiting bodies of mushroom Inonotus rickii. Their structures were elucidated by means of extensive spectroscopic methods. Compound 4 had moderate inhibitory activity on human colon cancer SW480 (IC50 = 20.4 µmol).

Highly oxygenated meroterpenoids from fruiting bodies of the mushroom Tricholoma terreum.

Four new meroterpenoids, terreumols A-D (1-4), with a rare 10-membered ring system, were isolated from the fruiting bodies of Tricholoma terreum. Their structures with absolute stereochemistry were determined by comprehensive spectroscopic methods, as well as single-crystal X-ray diffractions. Compounds 1, 3, and 4 were evaluated for their cytotoxicities against five human cancer cell lines; all of them exhibited inhibitory effects, with IC50 values comparable to those of cisplatin.

Meroterpenoid pigments from the basidiomycete Albatrellus ovinus.

Eight grifolin derivatives, involving three new monomers, albatrelins A-C (1-3), three novel dimers (meroterpenoid pigments), albatrelins D-F (4-6), and two known ones, 6a,7,8,9,10,10a-hexahydro-3,6,9-trimethyl-6-(4-methyl-3-penten-1-yl)-1,9-epoxy-6H-dibenzo[b,d]pyran (7) and confluentin (8), were isolated from Albatrellus ovinus. Their structures were established by extensive spectroscopic analysis. The absolute configurations of compounds 2-4 were determined as 9R by comparing their optical rotations with data reported in the literature. Albatrelin F (6) was isolated as a pair of C-2' tautomers with a ratio of 1.3:1. Confluentin (8) showed weak cytotoxicity against four human tumor cell lines, HL-60, SMMC-7712, A-549, and MCF-7, in vitro.

Two new sesquiterpenoids from the fungus Ceriporia alachuana.

Two new sesquiterpenoids, tremulenolide D (1) and muurolane-10ß,15-diol (2), together with four known sesquiterpenoids, tremulenediol A (3), 2ß-hydroxy-α-candinol (4), epicubenol (5), and 3ß-hydroxy-δ-candinol (6), were isolated from cultures of the fungus Ceriporia alachuana. The structures of new compounds were determined by extensive spectroscopic analyses. Structurally, compounds 1 and 3 are tremulane-type sesquiterpenoids with an unusual perhydroazulene carbon skeleton.

Two new triterpenoids from the fungus Perenniporia maackiae.

Two new triterpenoids, 3ß-(2-methoxy-oxalyloxy)-24-methylene-lanost-8-en-21-oic acid (1) and 3ß-(2-methoxy-oxalyloxy)-15α-hydroxy-24-methylene-lanost-8-en-21-oic acid (2), were isolated from cultures of the fungus Perenniporia maackiae, together with two previously known triterpenoids (3 and 4). Their structures were determined by spectroscopic methods, including 1D and 2D NMR, and MS analyses. All compounds were evaluated for their cytotoxic activities on five tumor cell lines.

Three new phenyl-ethanediols from the fruiting bodies of the mushroom Fomes fomentarius.

Three new phenyl-ethanediols, (1R)-(3-ethenylphenyl)-1,2-ethanediol (1), (1R)-(3-formylphenyl)-1,2-ethanediol (2), and (1R)-(3-acetophenyl)-1,2-ethanediol (3), were isolated from the fruiting bodies of the mushroom Fomes fomentarius, together with two related known compounds, (3-ethylphenyl)-1,2-ethanediol (4) and (4-acetophenyl)-1,2-ethanediol (5). Their structures were elucidated by spectroscopic methods including extensive 2D NMR techniques. Compounds 1-3 showed weak antimicrobial activity.

Two new sesquiterpenes from cultures of the basidiomycete Agaricus arvensis.

Two new drimane sesquiterpenoids, 11,12-dihydroxy-15-drimeneoic acid (1) and 3α,11,15-trihydroxydrimene (2), were isolated from cultures of the basidiomycete Agaricus arvensis, together with one known compound 3ß,11,12-trihydroxydrimene (3). Their structures were established by means of spectroscopic analysis.

Vibralactones D-F from cultures of the basidiomycete Boreostereum vibrans.

Three new metabolites, vibralactones D-F (1-3) were isolated from cultures of the basidiomycete Boreostereum vibrans. The relative configuration of 1 was established on the basis of X-ray diffraction analysis, while the absolute configurations of 1-3 were assigned using a modified Mosher's method. Compound 1 showed weak inhibitory activities against isozymes of 11beta-hydroxysteroid dehydrogenases (HSD) with IC(50) values of 85.7 microM (human HSD1), 295.2 microM (mouse HSD1), and 87.1 microM (human HSD2).

Speciosins A-K, oxygenated cyclohexanoids from the basidiomycete Hexagonia speciosa.

Eleven new oxygenated cyclohexanoids, speciosins A-K (1-11), and aporpinone A (12) were isolated from broth cultures of the basidiomycete Hexagonia speciosa. Their structures were elucidated on the basis of extensive spectroscopic analysis, while the structure of 8 was additionally confirmed by analysis of single-crystal X-ray diffraction data.

Two new cleistanthane diterpenes and a new isocoumarine from cultures of the basidiomycete Albatrellus confluens.

Two new cleistanthane-type diterpenes, 3alpha,5alpha,8beta-trihydroxycleistanth-13(17),15-dien-18-oic acid (1) and 8beta-hydroxy-18-norcleistanth-4(5),13(17),15-trien-3-one (2), a new isocoumarine, 3R-(2R-hydroxypropyl)-8-hydroxyl-7-methyl-3,4-dihydroisocoumarine (3), along with three known aurovertins, aurovertins B (4), C (5) and E (6), four known polyesters, orbuticin (7), BK223A (8), BK223B (9) and 15G256alpha-2-me (10), and a known isocoumarine, 3R-6-hydroxymellein (11), were isolated from cultures of the basidiomycete Albatrellus confluens. The structures of these compounds were established on the basis of spectroscopic and chemical methods.