RESUMO
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.
Assuntos
Basidiomycota/química , Cromonas/isolamento & purificação , Lipase/antagonistas & inibidores , Cromonas/química , Cromonas/farmacologia , Estrutura Molecular , Pâncreas/enzimologiaRESUMO
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).
Assuntos
Antifúngicos/isolamento & purificação , Lignanas/isolamento & purificação , Tiazinas/isolamento & purificação , Xanthium/química , Antifúngicos/química , Antifúngicos/farmacologia , Candida albicans/efeitos dos fármacos , Lignanas/química , Lignanas/farmacologia , Estrutura Molecular , Sementes/química , Tiazinas/química , Tiazinas/farmacologiaRESUMO
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.
Assuntos
Basidiomycota/química , Sesquiterpenos/isolamento & purificação , Coriolaceae , Cristalografia por Raios X , Fermentação , Estrutura Molecular , Ressonância Magnética Nuclear Biomolecular , Sesquiterpenos/química , Sesquiterpenos/farmacologiaRESUMO
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).
Assuntos
11-beta-Hidroxiesteroide Desidrogenase Tipo 1/antagonistas & inibidores , Antineoplásicos/isolamento & purificação , Basidiomycota/química , Sesquiterpenos/isolamento & purificação , Animais , Antineoplásicos/química , Antineoplásicos/farmacologia , Ensaios de Seleção de Medicamentos Antitumorais , Feminino , Humanos , Isoenzimas , Camundongos , Estrutura Molecular , Ressonância Magnética Nuclear Biomolecular , Sesquiterpenos/química , Sais de Tetrazólio/farmacologia , Tiazóis/farmacologiaRESUMO
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.
Assuntos
Alcaloides/isolamento & purificação , Reishi/química , Alcaloides/química , Carpóforos/química , Estrutura Molecular , Ressonância Magnética Nuclear BiomolecularRESUMO
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).
Assuntos
Basidiomycota/química , Sesquiterpenos/isolamento & purificação , Ensaios de Seleção de Medicamentos Antitumorais , Humanos , Estrutura Molecular , Ressonância Magnética Nuclear Biomolecular , Sesquiterpenos/química , Sesquiterpenos/farmacologiaRESUMO
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.
Assuntos
Ganoderma/química , Triterpenos/isolamento & purificação , Candida albicans/efeitos dos fármacos , China , Ensaios de Seleção de Medicamentos Antitumorais , Carpóforos/química , Células HL-60 , Humanos , Testes de Sensibilidade Microbiana , Estrutura Molecular , Ressonância Magnética Nuclear Biomolecular , Triterpenos/química , Triterpenos/farmacologiaRESUMO
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.
Assuntos
Agaricales/química , Antineoplásicos/isolamento & purificação , Sesquiterpenos/isolamento & purificação , Antineoplásicos/química , Antineoplásicos/farmacologia , Coriolaceae , Ensaios de Seleção de Medicamentos Antitumorais , Células HL-60 , Humanos , Estrutura Molecular , Sesquiterpenos/química , Sesquiterpenos/farmacologiaRESUMO
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 terreolidesâ A-F (1-6) and saponaceolidesâ H-P (8-16) were isolated from the fruiting bodies of the toxic mushroom T. terreum. Terreolidesâ 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, saponaceolideâ B (7) and saponaceolideâ M (13), displayed acute toxicity, with LD50 values of 88.3 and 63.7â 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.
Assuntos
Tricholoma/metabolismo , Animais , Creatina Quinase/sangue , Cristalografia por Raios X , Feminino , Dose Letal Mediana , Masculino , Camundongos , Camundongos Endogâmicos ICR , Conformação Molecular , Intoxicação Alimentar por Cogumelos , Tricholoma/química , Triterpenos/química , Triterpenos/isolamento & purificação , Triterpenos/toxicidadeRESUMO
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.
Assuntos
Coriolaceae/química , Proteína Tirosina Fosfatase não Receptora Tipo 1/antagonistas & inibidores , Sesquiterpenos/isolamento & purificação , Animais , Concentração Inibidora 50 , Estrutura Molecular , Ressonância Magnética Nuclear Biomolecular , Sesquiterpenos/química , Sesquiterpenos/farmacologiaRESUMO
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).
Assuntos
Agaricales/química , Antineoplásicos/isolamento & purificação , Sesquiterpenos/isolamento & purificação , Antineoplásicos/química , Antineoplásicos/farmacologia , China , Ensaios de Seleção de Medicamentos Antitumorais , Carpóforos/química , Humanos , Concentração Inibidora 50 , Estrutura Molecular , Ressonância Magnética Nuclear Biomolecular , Sesquiterpenos Policíclicos , Sesquiterpenos/química , Sesquiterpenos/farmacologiaRESUMO
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.
Assuntos
Antineoplásicos/isolamento & purificação , Terpenos/isolamento & purificação , Tricholoma/química , Agaricales/química , Antineoplásicos/química , Antineoplásicos/farmacologia , Ensaios de Seleção de Medicamentos Antitumorais , Feminino , França , Carpóforos/química , Células HL-60 , Humanos , Concentração Inibidora 50 , Estrutura Molecular , Oxigênio/análise , Terpenos/química , Terpenos/farmacologiaRESUMO
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.
Assuntos
Antineoplásicos/isolamento & purificação , Basidiomycota/química , Produtos Biológicos/isolamento & purificação , Pigmentos Biológicos/isolamento & purificação , Antineoplásicos/química , Antineoplásicos/farmacologia , Produtos Biológicos/química , Produtos Biológicos/farmacologia , China , Ensaios de Seleção de Medicamentos Antitumorais , Feminino , Células HL-60 , Humanos , Estrutura Molecular , Ressonância Magnética Nuclear Biomolecular , Fenóis/química , Fenóis/isolamento & purificação , Pigmentos Biológicos/química , Pigmentos Biológicos/farmacologia , Terpenos/química , Terpenos/isolamento & purificação , Terpenos/farmacologiaRESUMO
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.
Assuntos
Polyporales/química , Sesquiterpenos/isolamento & purificação , China , Estrutura Molecular , Ressonância Magnética Nuclear Biomolecular , Sesquiterpenos Policíclicos , Sesquiterpenos/química , EstereoisomerismoRESUMO
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.
Assuntos
Antineoplásicos/isolamento & purificação , Medicamentos de Ervas Chinesas/isolamento & purificação , Polyporaceae/química , Triterpenos/isolamento & purificação , Antineoplásicos/química , Antineoplásicos/farmacologia , Ensaios de Seleção de Medicamentos Antitumorais , Medicamentos de Ervas Chinesas/química , Medicamentos de Ervas Chinesas/farmacologia , Células HL-60 , Humanos , Estrutura Molecular , Ressonância Magnética Nuclear Biomolecular , Triterpenos/química , Triterpenos/farmacologiaRESUMO
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.
Assuntos
Agaricales/química , Etilenoglicóis/isolamento & purificação , Etilenoglicóis/química , Carpóforos/química , Estrutura Molecular , Ressonância Magnética Nuclear BiomolecularRESUMO
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.
Assuntos
Agaricus/química , Antineoplásicos/isolamento & purificação , Sesquiterpenos/isolamento & purificação , Antineoplásicos/química , Antineoplásicos/farmacologia , China , Ensaios de Seleção de Medicamentos Antitumorais , Feminino , Células HL-60 , Humanos , Estrutura Molecular , Ressonância Magnética Nuclear Biomolecular , Sesquiterpenos/química , Sesquiterpenos/farmacologiaRESUMO
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).
Assuntos
11-beta-Hidroxiesteroide Desidrogenases/antagonistas & inibidores , 11-beta-Hidroxiesteroide Desidrogenases/metabolismo , Basidiomycota/química , Lactonas/análise , Lactonas/farmacologia , 11-beta-Hidroxiesteroide Desidrogenases/genética , Animais , Linhagem Celular , Cristalografia por Raios X , Humanos , Lactonas/isolamento & purificação , Camundongos , Modelos Moleculares , TransfecçãoRESUMO
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.
Assuntos
Basidiomycota/química , Cicloexanóis/química , Cicloexanóis/isolamento & purificação , China , Cristalografia por Raios X , Conformação Molecular , Estrutura Molecular , Ressonância Magnética Nuclear Biomolecular , OxirreduçãoRESUMO
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.