RESUMEN
Ten new diterpene glycosides virescenosides Z9-Z18 (1-10) together with three known analogues (11-13) and aglycon of virescenoside A (14) were isolated from the marine-derived fungus Acremonium striatisporum KMM 4401. These compounds were obtained by cultivating fungus on wort agar medium with the addition of potassium bromide. Structures of the isolated metabolites were established based on spectroscopic methods. The effects of some isolated glycosides and aglycons 15-18 on urease activity and regulation of Reactive Oxygen Species (ROS) and Nitric Oxide (NO) production in macrophages stimulated with lipopolysaccharide (LPC) were evaluated.
Asunto(s)
Acremonium/química , Diterpenos/química , Glicósidos/química , Glicósidos/farmacología , Macrófagos/efectos de los fármacos , Animales , Diterpenos/aislamiento & purificación , Hongos , Glicósidos/aislamiento & purificación , Holothuria/microbiología , Lipopolisacáridos , Ratones , Estructura Molecular , Óxido Nítrico , Especies Reactivas de Oxígeno , Ureasa/efectos de los fármacosRESUMEN
Six new carotane sesquiterpenoids piltunines A-F (1-6) together with known compounds (7-9) were isolated from the marine-derived fungus Penicillium piltunense KMM 4668. Their structures were established using spectroscopic methods. The absolute configurations of 1-7 were determined based on circular dichroism (CD) and nuclear Overhauser spectroscopy (NOESY) data as well as biogenetic considerations. The cytotoxic activity of some of the isolated compounds and their effects on regulation of reactive oxygen species (ROS) and nitric oxide (NO) production in lipopolysaccharide-stimulated macrophages were examined.
Asunto(s)
Antineoplásicos/farmacología , Macrófagos/efectos de los fármacos , Penicillium/química , Sesquiterpenos/farmacología , Animales , Antineoplásicos/química , Antineoplásicos/aislamiento & purificación , Línea Celular Tumoral , Células Cultivadas , Dicroismo Circular , Ensayos de Selección de Medicamentos Antitumorales , Humanos , Macrófagos/metabolismo , Ratones , Ratones Endogámicos BALB C , Óxido Nítrico/metabolismo , Especies Reactivas de Oxígeno/metabolismo , Sesquiterpenos/química , Sesquiterpenos/aislamiento & purificaciónRESUMEN
Four new compounds were isolated from the Vietnamese marine sediment-derived fungus Aspergillus flocculosus, one aspyrone-related polyketide aspilactonol G (2), one meroterpenoid 12-epi-aspertetranone D (4), two drimane derivatives (7,9), together with five known metabolites (1,3,5,6,8,10). The structures of compounds 1-10 were established by NMR and MS techniques. The absolute stereoconfigurations of compounds 1 and 2 were determined by a modified Mosher's method. The absolute configurations of compounds 4 and 7 were established by a combination of analysis of ROESY data and coupling constants as well as biogenetic considerations. Compounds 7 and 8 exhibited cytotoxic activity toward human prostate cancer 22Rv1, human breast cancer MCF-7, and murine neuroblastoma Neuro-2a cells.
Asunto(s)
Antineoplásicos/farmacología , Organismos Acuáticos/metabolismo , Aspergillus/metabolismo , Productos Biológicos/farmacología , Hongos/metabolismo , Animales , Línea Celular Tumoral , Ensayos de Selección de Medicamentos Antitumorales/métodos , Sedimentos Geológicos/microbiología , Humanos , Células MCF-7 , Espectroscopía de Resonancia Magnética/métodos , Biología Marina/métodos , Ratones , Sesquiterpenos Policíclicos/farmacología , Policétidos/farmacología , Sesquiterpenos/farmacologíaRESUMEN
Four new indole-diterpene alkaloids asperindoles Aâ»D (1â»4) and the known p-terphenyl derivative 3″-hydroxyterphenyllin (5) were isolated from the marine-derived strain of the fungus Aspergillus sp., associated with an unidentified colonial ascidian. The structures of 1â»5 were established by 2D NMR and HRESIMS data. The absolute configurations of all stereocenters of 1â»4 were determined by the combination of ROESY data, coupling constants analysis, and biogenetic considerations. Asperindoles C and D contain a 2-hydroxyisobutyric acid (2-HIBA) residue, rarely found in natural compounds. Asperindole A exhibits cytotoxic activity against hormone therapy-resistant PC-3 and 22Rv1, as well as hormone therapy-sensitive human prostate cancer cells, and induces apoptosis in these cells at low-micromolar concentrations.
Asunto(s)
Antineoplásicos/farmacología , Aspergillus/química , Diterpenos/farmacología , Alcaloides Indólicos/farmacología , Urocordados/microbiología , Animales , Antineoplásicos/química , Antineoplásicos/aislamiento & purificación , Apoptosis/efectos de los fármacos , Organismos Acuáticos/microbiología , Línea Celular Tumoral , Diterpenos/química , Diterpenos/aislamiento & purificación , Docetaxel , Ensayos de Selección de Medicamentos Antitumorales , Humanos , Alcaloides Indólicos/química , Alcaloides Indólicos/aislamiento & purificación , Estructura Molecular , Estereoisomerismo , Taxoides/farmacologíaRESUMEN
Twelve new polyketides, zosteropenillines A-L (1-12), together with known polyketide pallidopenilline A (13), were isolated from the ethylacetate extract of the fungus Penicillium thomii associated with the seagrass Zostera marina. Their structures were established based on spectroscopic methods. The absolute configuration of zosteropenilline A (1) as 4R, 5S, 8S, 9R, 10R, and 13S was determined by a combination of the modified Mosher's method, X-ray analysis, and NOESY data. Absolute configurations of zosteropenillines B-D (2-4) were determined by timedependent density functional theory (TD-DFT) calculations of ECD spectra. The effect of compounds 1-3, 7, 8, 10, and 11 on the viability of human drug-resistant prostate cancer cells PC3 as well as on autophagy in these cancer cells and inhibitory effects of compounds 1, 2, and 8-10 on NO production in LPS-induced RAW 264.7 murine macrophages were examined.
Asunto(s)
Antineoplásicos/farmacología , Organismos Acuáticos/química , Autofagia/efectos de los fármacos , Penicillium/química , Policétidos/farmacología , Animales , Antineoplásicos/química , Antineoplásicos/aislamiento & purificación , Línea Celular Tumoral , Cristalografía por Rayos X , Humanos , Ratones , Estructura Molecular , Óxido Nítrico/metabolismo , Resonancia Magnética Nuclear Biomolecular , Policétidos/química , Policétidos/aislamiento & purificación , Células RAW 264.7 , Zosteraceae/microbiologíaRESUMEN
Eleven new polyketides, pallidopenillines 1-11, were isolated from the alga-derived fungus Penicillium thomii. The structures of these compounds were established based on spectroscopic methods. The absolute configuration of pallidopenilline A (1) as 4R, 5S, 8S, 9R, 10R, 13R was established using a combination of the modified Mosher's method, X-ray analysis, and NOESY data. The absolute configurations of 2-5 were determined by time-dependent density functional theory calculations of the ECD spectra and ECD and NOESY data. It was shown that 1-acetylpallidopenilline A (2) and pallidopenilline G (10) inhibit the growth of colonies of 22Rv1 cells by 40% at 2 and 1 µM, respectively.
Asunto(s)
Antineoplásicos/aislamiento & purificación , Penicillium/química , Policétidos/aislamiento & purificación , Antineoplásicos/química , Antineoplásicos/farmacología , Ensayos de Selección de Medicamentos Antitumorales , Células HCT116 , Humanos , Estructura Molecular , Resonancia Magnética Nuclear Biomolecular , Policétidos/química , Policétidos/farmacología , Sargassum/microbiologíaRESUMEN
Three new epidithiodiketopiperazines pretrichodermamides D-F (1-3), together with the known N-methylpretrichodermamide B (4) and pretrichodermamide С (5), were isolated from the lipophilic extract of the marine algae-derived fungus Penicillium sp. KMM 4672. The structures of compounds 1-5 were determined based on spectroscopic methods. The absolute configuration of pretrichodermamide D (1) was established by a combination of modified Mosher's method, NOESY data, and biogenetic considerations. N-Methylpretrichodermamide B (5) showed strong cytotoxicity against 22Rv1 human prostate cancer cells resistant to androgen receptor targeted therapies.
Asunto(s)
Productos Biológicos/química , Diterpenos/química , Hongos/química , Penicillium/química , Piperazinas/química , Productos Biológicos/farmacología , Línea Celular Tumoral , Diterpenos/farmacología , Ensayos de Selección de Medicamentos Antitumorales , Humanos , Biología Marina/métodos , Estructura Molecular , Piperazinas/farmacologíaRESUMEN
Six new highly oxygenated chromene derivatives, oxirapentyns F-K (2-7), one new polyketide (8), one new benzofurane (9), and two known cyclodepsipeptides, isoisariin B and isaridin E, were isolated from the lipophilic extract of the marine-derived fungus Isaria felina KMM 4639. The structures of compounds 2-9 were determined using spectroscopic methods. The relative configurations of compounds 2-7 were established through a combination of NOE data and spin coupling constants, and these results were confirmed by X-ray crystallographic analysis of 4. The absolute structures of all oxirapentyns were assumed based on their biogenetic relationship and confirmed using the modified Mosher's method on 2 and 7. Isariketide (8) showed moderate cytotoxicity toward HL-60 cells.
Asunto(s)
Alquinos/aislamiento & purificación , Antineoplásicos/aislamiento & purificación , Benzopiranos/aislamiento & purificación , Depsipéptidos/aislamiento & purificación , Sedimentos Geológicos/química , Hypocreales/química , Alquinos/química , Alquinos/farmacología , Antineoplásicos/química , Antineoplásicos/farmacología , Benzopiranos/química , Benzopiranos/farmacología , Supervivencia Celular/efectos de los fármacos , Cristalografía por Rayos X , Depsipéptidos/química , Ensayos de Selección de Medicamentos Antitumorales , Células HL-60 , Humanos , Biología Marina , Pruebas de Sensibilidad Microbiana , Conformación Molecular , Estructura Molecular , Resonancia Magnética Nuclear Biomolecular , Océanos y MaresRESUMEN
Ten new austalide meroterpenoids (1-10) were isolated from the alga-derived fungi Penicillium thomii KMM 4645 and Penicillium lividum KMM 4663. Their structures were elucidated by extensive spectroscopic analysis and by comparison with related known compounds. The absolute configurations of some of the metabolites were assigned by the modified Mosher's method and CD data. Compounds 1, 2, 8, and 9 were able to inhibit AP-1-dependent transcriptional activity in JB6 Cl41 cell lines at noncytotoxic concentrations. Austalides 1-5, 8, and 9 exhibited significant inhibitory activity against endo-1,3-ß-D-glucanase from a crystalline stalk of the marine mollusk Pseudocardium sachalinensis.
Asunto(s)
Penicillium/química , Terpenos/aislamiento & purificación , Animales , Aspergillus/química , Ensayos de Selección de Medicamentos Antitumorales , Japón , Ratones , Estructura Molecular , Resonancia Magnética Nuclear Biomolecular , Océanos y Mares , Sargassum/microbiología , Terpenos/química , Terpenos/farmacología , Factor de Transcripción AP-1/efectos de los fármacosRESUMEN
Seven new 6,6-spiroketals, sargassopenillines A-G (1-7) were isolated from the alga-derived fungi Penicillium thomii KMM 4645 and Penicillium lividum KMM 4663. The structures of these metabolites were determined by HR-MS and 1D and 2D NMR. The absolute configurations of compounds 1, 5 and 6 were assigned by the modified Mosher's method and by CD data. Sargassopenilline C (3) inhibited the transcriptional activity of the oncogenic nuclear factor AP-1 with an IC50 value of 15 µM.
Asunto(s)
Hongos/química , Furanos/química , Furanos/farmacología , Penicillium/química , Phaeophyceae/microbiología , Compuestos de Espiro/química , Compuestos de Espiro/farmacología , Animales , Espectroscopía de Resonancia Magnética/métodos , Ratones , Factor de Transcripción AP-1/metabolismoRESUMEN
Six new triterpenoids (1-6) and the previously known penasterone, acetylpenasterol, and ergosta-4,24(28)-dien-3-one were isolated from a Penares sp. sponge collected from Vietnamese waters. Structures of the obtained compounds were established by extensive 1D and 2D NMR spectroscopy and mass spectrometry. Configurations of the triterpene epoxy lactones (1-4) were determined on the basis of NOESY and CD data and calculation of spin coupling constants and confirmed by X-ray crystallographic analysis of compound 2. The isolated triterpenoid 6 was cytotoxic against human leukemia HL-60 cells (IC50 = 9.7 µM).
Asunto(s)
Antineoplásicos/aislamiento & purificación , Antineoplásicos/farmacología , Poríferos/química , Triterpenos/aislamiento & purificación , Triterpenos/farmacología , Animales , Antineoplásicos/química , Cristalografía por Rayos X , Ensayos de Selección de Medicamentos Antitumorales , Células HL-60 , Humanos , Lanosterol/análogos & derivados , Biología Marina , Estructura Molecular , Resonancia Magnética Nuclear Biomolecular , Triterpenos/química , VietnamRESUMEN
Nine naphto-γ-pyrones rubrofusarine B (1), TMC 256 A1 (2), fansecinones A (3) and B (4), aurasperones A (5), B (6) and F (7), dianhydro-aurasperone C (8) and asperpyrone B (9) were isolated from the marine-derived fungus Aspergillus foetidus KMM 4694. Their structures were established based on spectroscopic methods. The effect of the substances on viability and colony formation of human drug-resistant prostate cancer 22Rv1 cell was evaluated.
Asunto(s)
Antineoplásicos/farmacología , Aspergillus/química , Pironas/química , Pironas/farmacología , Antineoplásicos/química , Línea Celular Tumoral , Resistencia a Antineoplásicos , Ensayos de Selección de Medicamentos Antitumorales , Humanos , Espectroscopía de Resonancia Magnética , Masculino , Estructura Molecular , Neoplasias de la Próstata/tratamiento farmacológico , Neoplasias de la Próstata/patologíaRESUMEN
One new dihydrobenzofuran derivative (1), known depsipeptide emericellamide A (2), three known drimanes (3-5) and two artifact drimane derivatives (6, 7) were isolated from the marine-derived fungus Aspergillus ustus KMM 4664. Their structures were determined by detailed analysis of spectroscopic data and by comparison with related known compounds. The absolute configuration of 1 was determined by time-dependent density functional theory (TD-DFT) calculations of ECD spectra. Compound 7 showed significant ability of the inhibition of spermatozoa to fertilize egg-cells of the sea urchin Strongylocentrotus intermedius with IC50 value 21 µM.
Asunto(s)
Aspergillus , Furanos/farmacología , Animales , Aspergillus/química , Furanos/aislamiento & purificación , Masculino , Estructura Molecular , Espermatozoides/efectos de los fármacos , StrongylocentrotusRESUMEN
Four new diketopiperazine alkaloids, citriperazines A-D were isolated from algae-derived Penicillium sp. KMM 4672. The structures of compounds 1-4 were determined using spectroscopic methods. The absolute configurations of compounds 1 and 4 were established by comparison of calculated and experimental ECD spectra. The cytotoxicity of compounds 1-4 against several human prostate cell lines was evaluated.
Asunto(s)
Dicetopiperazinas/aislamiento & purificación , Penicillium/química , Alcaloides/química , Alcaloides/aislamiento & purificación , Línea Celular Tumoral , Citotoxinas/química , Citotoxinas/aislamiento & purificación , Citotoxinas/farmacología , Dicetopiperazinas/química , Humanos , Conformación Molecular , Estructura Molecular , Análisis EspectralRESUMEN
Two new auroglaucin-derived compounds, niveoglaucins A (1) and B (2), together with four known related compounds were isolated from extract of the marine sediment-derived strain of Aspergillus niveoglaucus. The structures of these compounds were determined by 1D and 2D NMR spectroscopy and high resolution MS. The plausible biosynthetic pathway was proposed for new compounds 1 and 2. The neuroprotective activity in 6-OHDA-induced Parkinson's disease cell model was shown for niveoglaucin A (1).
Asunto(s)
Aspergillus/química , Sedimentos Geológicos/química , Fármacos Neuroprotectores/aislamiento & purificación , Animales , Antiparkinsonianos/aislamiento & purificación , Línea Celular , Hongos/química , Sedimentos Geológicos/microbiología , Humanos , Espectroscopía de Resonancia Magnética , Espectrometría de Masas , Ratones , Modelos Biológicos , Estructura Molecular , Fármacos Neuroprotectores/química , Fármacos Neuroprotectores/farmacología , Oxidopamina/efectos adversos , Trastornos Parkinsonianos/inducido químicamente , Trastornos Parkinsonianos/tratamiento farmacológico , Trastornos Parkinsonianos/patología , VietnamRESUMEN
Five new prenylated indole alkaloids, 17-hydroxynotoamide D (1), 17-O-ethylnotoamide M (2), 10-O-acetylsclerotiamide (3), 10-O-ethylsclerotiamide (4), and 10-O-ethylnotoamide R (5) were isolated from a co-culture of marine-derived fungi Aspergillus sulphureus KMM 4640 and Isaria felina KMM 4639. The structures of 1-5 were determined by detailed analysis of spectroscopic data and by comparison with related known compounds. The absolute configurations of 1-5 were determined by time-dependent density functional theory (TD-DFT) calculations of ECD spectra. Compound 2 is able to inhibit the colony formation of human prostate cancer cells 22Rv1 at non-cytotoxic concentration of 10 µM.
Asunto(s)
Ascomicetos/metabolismo , Aspergillus/metabolismo , Técnicas de Cocultivo , Alcaloides Indólicos/metabolismo , Antineoplásicos/química , Antineoplásicos/metabolismo , Antineoplásicos/farmacología , Organismos Acuáticos , Línea Celular Tumoral , Supervivencia Celular/efectos de los fármacos , Humanos , Alcaloides Indólicos/química , Modelos Moleculares , Estructura MolecularRESUMEN
Three new diterpene glycosides, virescenosides V (1), W (2), and X (3) have been isolated from a marine strain of Acremonium striatisporum KMM 4401 associated with the holothurian Eupentacta fraudatrix. Their structures have been elucidated on the basis of high resolution mass spectrometry, 1D and 2D NMR (1H, 13C, DEPT, COSY 45, COSY RCT, HSQC, HMBC, and NOESY spectra) as 19-O-beta-D-altropyranosyl-7-oxo-isopimara-8(14),15-diene-2alpha,3beta-diol (1), 19-O-beta-D-altropyranosyl-isopimara-7,15-diene-2 alpha,3 beta,6 alpha-triol (2), and 19-O-beta-D-altropyranosyl-isopimara-8,15-diene-2 alpha,3 beta,7 alpha-triol (3).
Asunto(s)
Acremonium/química , Diterpenos/aislamiento & purificación , Glicósidos/aislamiento & purificación , Pepinos de Mar/microbiología , Animales , Diterpenos/química , Glicósidos/química , Estructura Molecular , Resonancia Magnética Nuclear Biomolecular , Rotación Óptica , Espectrometría de Masa Bombardeada por Átomos Veloces , Espectrofotometría Ultravioleta , EstereoisomerismoRESUMEN
The new 6,6-spiroketal,sargassopenilline H (1), and known peneciraistin C (2) have been isolated from an EtOAc extract of the marine-derived fungus Penicillium lividumKMM 4663. The structure of the new metabolite was determined by HR ESIMS and 1D and 2D NMR spectroscopy. Sargassopenilline H (1) in non-cytotoxic concentration inhibited colony formation of RPMI-7951 and MDA-MB-231 cell lines.
Asunto(s)
Benzopiranos/química , Benzopiranos/farmacología , Penicillium/química , Compuestos de Espiro/química , Compuestos de Espiro/farmacología , Antineoplásicos/química , Antineoplásicos/farmacología , Línea Celular Tumoral , Proliferación Celular/efectos de los fármacos , Humanos , Estructura MolecularRESUMEN
A new polyketide 1 and a new decaline derivative 2 were isolated from a sediment-derived fungus Aspergillus carneus Blochwitz, together with one known bisabolane sesquiterpenoid and seven known polyketide metabolites. The structures of the isolated compounds were established by HR-MS, and 1D and 2D NMR spectroscopy. The cytotoxic and antiradical activities of the isolated compounds were evaluated.
Asunto(s)
Aspergillus/química , Policétidos/aislamiento & purificación , Animales , Aspergillus/metabolismo , Línea Celular Tumoral , Ensayos de Selección de Medicamentos Antitumorales , Sedimentos Geológicos/microbiología , Ratones , Estructura Molecular , Policétidos/químicaRESUMEN
Oxirapentyn A (1), oxirapentyn B (2), and oxirapentyn E (3) were examined for their ability to stimulate growth of seedling roots of barley (Hordeum vulgare L.), buckwheat (Fagopyrum esculentum Moench), corn (Zea mays L.), soy {Glycine max (L.) Merr.}, and wheat (Triticum aestivum L.). It was shown that the stimulatory effects depend on the chemical structure of the oxirapentyns and on the plant species. Compounds 1, and 2 are efficient for growth of seedling roots of barley, and wheat, whereas compound 3, at different concentrations, stimulates growth of seedling roots of maize, soy, and wheat. These compounds can be recommended for field study as plant growth stimulators.