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Abstarct New 1,3,6-trihydroxy-7-(dihydroxypropyl)-anthraquinone (1) and 6-(3′-hydroxybutan-2′-yl)-3,5-dimethyltetrahydro-2H-pyran-2-one (2), along with three previously known compounds, 1,3-dihydroxy-6-hydroxymethyl-7-methoxyanthraquinone (3), 1,3-dihydroxy-6-methyl-7-methoxyanthraquinone (4) and biphenyl-2,2′-diyl-diacetate (5) were isolated from the lipophilic extract of the marine sediment-derived fungus Thermomyces lanuginosus KMM 4681. The structures of the isolated compounds were established based on spectroscopic data. The absolute configurations of the stereocentres of 1 were determined using the time-dependent density functional theory (TD-DFT) calculation of ECD spectra. The effects of 1-4 on viability and colony formation of drug-resistant prostate cancer 22Rv1 and human PNT-2 cells were examined.

Three new tripeptide derivatives asterripeptides A–C (1–3) were isolated from Vietnamese mangrove-derived fungus Aspergillus terreus LM.5.2. Structures of isolated compounds were determined by a combination of NMR and ESIMS techniques. The absolute configurations of all stereocenters were determined using the Murfey’s method. The isolated compounds 1–3 contain a rare fungi cinnamic acid residue. The cytotoxicity of isolated compounds against several cancer cell lines and inhibition ability of sortase A from Staphylococcus aureus of asterripeptides A–C were investigated.

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 fungu...

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.

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.

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).

Seven new deoxyisoaustamide derivatives (1&ndash, 7) together with known compounds (8&ndash, 10) were isolated from the coral-derived fungus Penicillium dimorphosporum KMM 4689. Their structures were established using spectroscopic methods, X-ray diffraction analysis and by comparison with related known compounds. The absolute configurations of some alkaloids were determined based on CD and NOESY data as well as biogenetic considerations. The cytotoxic and neuroprotective activities of some of the isolated compounds were examined and structure-activity relationships were pointed out. New deoxyisoaustamides 4&ndash, 6 at concentration of 1 &micro, M revealed a statistical increase of PQ(paraquat)-treated Neuro-2a cell viability by 30&ndash, 39%.

Seven new deoxyisoaustamide derivatives (1–7) together with known compounds (8–10) were isolated from the coral-derived fungus Penicillium dimorphosporum KMM 4689. Their structures were established using spectroscopic methods, X-ray diffraction analysis and by comparison with related known compounds. The absolute configurations of some alkaloids were determined based on CD and NOESY data as well as biogenetic considerations. The cytotoxic and neuroprotective activities of some of the isolated compounds were examined and structure-activity relationships were pointed out. New deoxyisoaustamides 4–6 at concentration of 1 µM revealed a statistical increase of PQ(paraquat)-treated Neuro-2a cell viability by 30–39%.

Six new carotane sesquiterpenoids piltunines A&ndash, F (1&ndash, 6) together with known compounds (7&ndash, 9) were isolated from the marine-derived fungus Penicillium piltunense KMM 4668. Their structures were established using spectroscopic methods. The absolute configurations of 1&ndash, 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.

One new dihydrobenzofuran derivative (

Nine naphto-γ-pyrones rubrofusarine B (

Four new diketopiperazine alkaloids, citriperazines A-D were isolated from algae-derived

Two new auroglaucin-derived compounds, niveoglaucins A (

Two new sesterterpenoids, terretonins H ( 1 ) and I ( 2 ), together with two known compounds, strobilactone A ( 3 ) and cerebroside D ( 4 ), were isolated from the lipophilic extract of the marine-derived fungus Aspergillus ustus KMM 4664. The structures of compounds 1 and 2 were determined based on spectroscopic methods and confirmed by X-ray crystallographic analysis of terretonin H. All compounds were tested for cytotoxic and embryotoxic effects using sperm and developing embryos of the sea urchin Strongylocentrotus intermedius and human cancer cells.

Four new diterpene glycosides, virescenosides R1 (1), R2 (2), R3 (3) and Z (4) were isolated from a marine strain of Acremonium striatisporum KMM 4401 associated with the holothurian Eupentacta fraudatrix. Structures of 1–3 were determined as the corresponding biosides having isopimaradiene-type aglycons with additional oxidation and unsaturation patterns. Virescenosides Z (4) was structurally identified as altroside, containing 7-en-6-one group in the tricyclic aglycon moiety. The compounds 1–4 were examined for inhibition of non-specific esterase activity in mouse lymphocytes.

New diorcinol J (1) and four known diorcinols B-E (2-5) were isolated from the EtOAc extract of a co-culture of marine isolates of the fungi Aspergillus sulphureus KMM 4640 and Isaria felina KMM 4639. The structure of diorcinol J was established using NMR spectroscopy and high-resolution mass spectrometry. The cytotoxicity of the isolated compounds and their ability to enhance expression of heat shock protein Hsp70 in Ehrlich ascites carcinoma cells were investigated.

A new meroterpenoid, austalide H acid ethyl ester (1), 5-(2′,4′-dihydroxy-6′-methylphenyl)-3-methylfuran-2-carboxylic acid (2), 5-(2′-hydroxy-6′-methylphenyl)-3-methylfuran-2-carboxylic acid (3) and 5-((6′-methyl-4′-oxo-3′,4′-dihydro-2H-pyran-2′-yl)methyl)-3-methylfuran-2-carboxylic acid (4), along with six known compounds, austalides H, J, K, and P (5–8), questin (9) and sulochrin (10) were isolated from the lipophilic extract of the alga-derived fungi Penicillium thomii KMM 4645 and Penicillium lividum KMM 4663. The structures of the isolated compounds were determined based on spectroscopic methods. The austalides showed significant inhibitory activity against endo-1,3-β-d-Glucanase from a crystalline stalk of the marine mollusk Pseudocardium sachalinensis.

Four new indole-diterpene alkaloids asperindoles A&ndash, D (1&ndash, 4) and the known p-terphenyl derivative 3&Prime, hydroxyterphenyllin (5) were isolated from the marine-derived strain of the fungus Aspergillus sp., associated with an unidentified colonial ascidian. The structures of 1&ndash, 5 were established by 2D NMR and HRESIMS data. The absolute configurations of all stereocenters of 1&ndash, 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.

Four new indole-diterpene alkaloids asperindoles A–D (1–4) 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 1–5 were established by 2D NMR and HRESIMS data. The absolute configurations of all stereocenters of 1–4 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.

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.

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.

A new aromatic nucleoside kipukasin J (1) and two known compounds decumbenone B (2) and cyclopenol (3) were separated from marine isolate of the fungus Aspergillus flavus. The structure of kipukasin J was elucidated using NMR spectroscopy and high-resolution mass spectrometry. The antimicrobial activity of the separated compounds was investigated.

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.

Prenylated indole alkaloids, carneamides A-C (1-3), quinazolinone derivatives, carnequinazolines A-C (5-7), aryl C-glycosides, carnemycin A, B (8, 9) and a drimane sesquiterpenoid (10), together with known compounds (11-21) were isolated from the marine-derived fungus Aspergillus carneus (Trichocomaceae) KMM 4638. The antimicrobial and cytotoxic activities of the several alkaloids were examined.

The new spirocyclic diketopiperazine alkaloid spirotryprostatin F was isolated from the marine isolate of the fungus Aspergillus fumigatus. The structure of the compound was established using on NMR spectroscopy, high-resolution mass spectrometry, and acid hydrolysis. Spirotryprostatin F in low and ultralow doses (10–6–10–17 M) exhibited stimulating action on the growth of sprout roots of soy [Glycine max (L.) Merr.], buckwheat (Fagopyrum esculentum Moench), and corn (Zea mays L.). The dose-effect curve had a bimodal character.

The effect of decumbenones A (1), B (2) and C (3) from the marine-derived strain of the fungus Aspergillus sulphureus on the growth of seedling roots of buckwheat, wheat, barley and corn at the concentration range 10﹣5 - 10﹣18 M was studied. It was shown that decumbenone B had a stimulatory effect on the growth of seedling roots of buckwheat, decumbenone A—on the growth of seedling roots of spring soft wheat, decumbenone C—on the growth of seedling roots of spring barley, decumbenone A, B and C —on the growth of seedling roots of corn. The stimulatory effect for some substances was shown at ultra-low concentrations 10﹣12 - 10﹣18 M. It is possible to recommend decumbenones A, B and C for studying in field conditions as growth factors of buckwheat, wheat, barley and corn.

New C14-surfactin methyl ester and eight earlier described surfactins were isolated from the marine bacterium Bacillus pumilus associated with zoantharia Palythoa sp. The structure of the compounds isolated was established based on the data from amino acid analysis, one- and two-dimensional NMR spectroscopy, and tandem nanoelectrospray mass spectrometry. The absolute configurations of amino acids were determined by Marfey’s method. Cytotoxic activity of a number of surfactins with respect to the tumor cells HCT-116 and MDA-MB-231 was studied.

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-β-d-glucanase from a crystalline stalk of the marine mollusk Pseudocardium sachalinensis.

The new oxepin-containing (1) and quinazolinone (2) alkaloids and new dihydrobenzofuran derivative (3) have been isolated from a marine strain of Aspergillus carneus KMM 4638. The structures of these metabolites were determined by HR-MS and 1D and 2D NMR, along with Marfey's method.

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 PenicilliumlividumKMM 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.

A new alkaloid, fumiquinazoline K (1), and a new nordammarane triterpenoid (2), together with three known diketopiperazines (3-5) and tryptoquivaline F (6) have been isolated from a marine strain of Aspergillus fumigatus KMM 4 631 associated with the soft coral Sinularia sp. Their structures were determined by HR-MS and 1D and 2D NMR. Compounds 3-5 exhibit weak cytotoxicity against cytoplasm non-specific esterase in Ehrlich carcinoma cells. Compound 3 also induces early apoptosis of the same cells in a non-toxic range of concentrations.