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.

Novel Natural Oximes and Oxime Esters with a Vibralactone Backbone from the Basidiomycete Boreostereum vibrans.

A variety of novel natural products with significant bioactivities are produced by the basidiomycete Boreostereum vibrans. In the present study, we describe 16 novel natural oximes and oxime esters with a vibralactone backbone, vibralactoximes, which were isolated from the scale-up fermentation broth of B. vibrans.

Leucocontextins A-R, lanostane-type triterpenoids from Ganoderma leucocontextum.

Eighteen new lanostane-type triterpenoids, namely leucocontextins A-R (1-18) were isolated from the fruiting bodies of Ganoderma leucocontextum. Their structures were established by 1D and 2D NMR data in conjunction with HRESIMS/HREIMS, X-ray single crystal diffraction analysis. Compound 18 exhibited weak cytotoxicity against K562 and MCF-7 cell lines with IC50 of 20-30 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.

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.

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.

Four new spiroaxane sesquiterpenes and one new rosenonolactone derivative from cultures of Basidiomycete Trametes versicolor.

Four new spiroaxane sesquiterpenes, tramspiroins A-D (1-4), one new rosenonolactone 15,16-acetonide (5), and the known drimane sesquiterpenes isodrimenediol (6) and funatrol D (7) have been isolated from the cultures of Basidiomycete Trametes versicolor. The structures of new compounds were elucidated by means of spectroscopic methods. Compounds 1-7 were investigated for their cytotoxicities against five human cancer cell lines.

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 11β-hydroxysteroid dehydrogenases (11β-HSD).

Structure-Based Optimization and Biological Evaluation of Pancreatic Lipase Inhibitors as Novel Potential Antiobesity Agents.

The unusual fused β-lactone vibralactone was isolated from cultures of the basidiomycete Boreostereum vibrans and has been shown to significantly inhibit pancreatic lipase. In this study, a structure-based lead optimization of vibralactone resulted in three series of 104 analogs, among which compound C1 exhibited the most potent inhibition of pancreatic lipase, with an IC50 value of 14 nM. This activity is more than 3000-fold higher than that of vibralactone.

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.

Brasilane sesquiterpenoids and alkane derivatives from cultures of the basidiomycete Coltricia sideroides.

Three new brasilane-type sesquiterpenoids, brasilanes A-C (1-3), together with two new alkane derivatives, colisiderin A (4) and 7(E),9(E)-undecandiene-2,4,5-triol (5), were isolated from cultures of the basidiomycete Coltricia sideroides. Their structures were elucidated by NMR and MS data analyses. The absolute configuration of 4 was determined by TDDFT ECD calculations while brasilane-type sesquiterpenoids were isolated from cultures of mushroom for the first time.

New Diterpenes from Cultures of the Fungus Engleromyces goetzii and Their CETP Inhibitory Activity.

One new cleistanthane-type diterpene named engleromycenolic acid A (1), one new rosane-type diterpene named engleromycenolic acid B (2) and one new natural rosane-type diterpene, engleromycenol (3), along with three known rosane-type diterpenes, rosololactone (4), rosenonolactone (5) and 7-deoxyrosenonolactone (6) were isolated from cultures of the fungus Engleromyces goetzii, where it naturally grows on Alpine bamboo culms. The new compounds were elucidated based on their spectroscopic data. In addition, compounds 1-6 were evaluated for their cholesterol ester transfer protein (CETP) inhibition activity.

A Viscidane Diterpene and Polyacetylenes from Cultures of Hypsizygus marmoreus.

Investigation on the cultures of Hypsizygus marmoreus resulted in the isolation of a new viscidane diterpene, 8-oxoviscida-3,11(18)-diene-13,14,15,19-tetraol (1) and two new polyacetylenes, (E)-10-(1,1-dimethyl-2-propenyloxy)-2-decene-4,6,8-triyn-1-ol (2) and 10-(1,1-dimethyl-2-propenyloxy)deca-4,6,8-triyn-1-ol (3), together with two known polyacetylenes, (E)-2-decen-4,6,8-triyn-1-ol (4) and 4,6,8-decatriyn-1-ol (5). Their structures were elucidated on the basis of extensive spectroscopic studies. Compound 1 is the first finding of viscidane diterpene in mushrooms.

Seven new drimane-type sesquiterpenoids from cultures of fungus Laetiporus sulphureus.

Seven new drimane-type sesquiterpenoids, sulphureuines B-H (1-7), together with four known compounds (8-11), were obtained from cultures of mushroom Laetiporus sulphureus. All of these compounds were tested for their cytotoxicities against five human cancer cell lines (HL-60, SMMC-721, A-549, MCF-7, SW-480), compound 10 showed potent cytotoxic activity against HL-60, SMMC-721, A-549, SW-480, with IC50 values of 37.5, 14.

Identification and Cytotoxic Activities of Two New Trichothecenes and a New Cuparane-Type Sesquiterpenoid from the Cultures of the Mushroom Engleromyces goetzii.

Engleromyces goetzii is a traditional medicinal mushroom that is widely used to treat infection, inflammation and cancer in Tibet, Sichuan and Yunnan provinces of China. Two new trichothecenes, engleromycones A and B (1 and 2), one new cuparane-type sesquiterpenoid named infuscol F (11), eight known trichothecene analogs, sambucinol (3), 3-deoxysambucinol (4), trichothecolone (5), trichodermol (6), 8-deoxytrichothecin (7), trichothecin (8), trichothecinol B (9) and trichothecinol A (10), and one known cyclopentanoid sesquiterpene cyclonerodiol (12) were isolated from the cultures of E. goetzii.

Two new triterpenoids from fruiting bodies of fungus Ganoderma lucidum.

Two new triterpenoids, (24E)-9α,11α-epoxy-3β-hydroxylanosta-7,24-dien-26-al (1) and (22Z,24Z)-13-hydroxy-3-oxo-14(13 → 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 → 12)abeo-lanostane skeleton with a 26,23-olide moiety.

Four New Sesquiterpenoids from Cultures of the Fungus Phellinidium sulphurascens.

Four new sesquiterpenoids, namely 12-hydroxy-3-oxodrimenol (1), 11-hydroxyacetoxydrim-7-en-3β-ol (2), 2,6-dimethyl-7,10-epoxy-10-hydroxymethyldodeca-2,11-dien-6-ol (3), and 7,10-epoxy-2,6,10-trimethyldodeca-2,11-diene-4,6-diol (4), along with fourteen known compounds, were isolated from the cultures of Phellinidium sulphurascens. The structures of compounds 1-4 were established on the basis of extensive spectroscopic analysis. All of them were evaluated for their cytotoxic activities.

Steroids and Sesquiterpenes From Cultures of the Fungus Phellinus igniarius.

Two new steroids, 3α,17α,19,20-tetrahydroxy-4α-methylpregn-8-ene (1) and 3α,12α,17α,20-tetrahydroxy-4α-methylpregn-8-ene (2) and three new sesquiterpenoids, 12-hydroxy-α-cadinol (3), 3α,12-dihydroxy-δ-cadinol (4), and 3α,6α-dihydroxyspiroax-4-ene (5), have been isolated from cultures of the fungus Phellinus igniarius. Their structures were characterized based on extensive spectroscopic data. In preliminary in vitro assays, compounds 3 and 4 exhibited the vascular-activities against phenylephrine-induced vasoconstriction with the relaxing rates of 11.

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.

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,6β-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.

Nine new farnesylphenols from the basidiomycete albatrellus caeruleoporus.

Nine previously-unreported farnesylphenols, involving eight neogrifolin derivatives (1-8) and one grifolin analogue (9), together with three known compounds, were isolated from the fruiting bodies of the mushroom Albatrellus caeruleoporus. Their structures were elucidated as (S)-17-hydroxy-18,20-ene-neogrifolin (1), (S)-18,19-dihydroxyneogrifolin (2), (S)-9-hydroxy-10,22-ene-neogrifolin (3), (9S,10R)-6,10-epoxy-9-hydroxyneo grifolin (4), (9S,10R)-6,9-epoxy-10-hydroxyneogrifolin (5), (-)-13,14-dihydroxyneogrifolin (6), albatrelin G (7), albatrelin H (8), and one grifolin analogue, (S)-10-hydroxygrifolin (9), grifolin (10), neogrifolin (11), and albatrellin (12) by extensive spectroscopic analyses and chemical methods. Compounds 7 and 8 showed weak cytotoxic activity to cell lines HL-60, SMMC-7721, A-549, and MCF-7, in vitro.

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.

Seven New Drimane-Type Sesquiterpenoids from Cultures of Fungus Phellinus tuberculosus.

Seven new drimane-type sesquiterpennoids, phellinuins A-G (1-7), together with one known compound 3β,11,12-trihydroxydrimene (8) were isolated from the cultures of mushroom Phellinus tuberculosus. Their structures were elucidated on the basis of NMR and MS spectroscopic data and by comparison with data reported in the literature.

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.

Norbisabolane and eremophilane sesquiterpenoids from cultures of the Basidiomycete Polyporus ellisii.

Three new 11,12,15-norbisabolane sesquiterpenoids, polisins A-C (1-3), and four new eremophilane sesquiterpenoids, polylisins A-D (4-7), were isolated from cultures of the Basidiomycete Polyporus ellisii. These new structures were elucidated based on extensive spectroscopic studies and the structures of polisin A (1) and polylisin A (4) were confirmed by single-crystal X-ray crystallographic analysis. All compounds were evaluated for their inhibitory activities against two isozymes of 11β-hydroxysteroid dehydrogenases (11β-HSD1 and 11β-HSD2).