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1.
Nat Prod Res ; 35(19): 3332-3335, 2021 Oct.
Article in English | MEDLINE | ID: mdl-31726858

ABSTRACT

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.


Subject(s)
Aspergillus , Furans/pharmacology , Animals , Aspergillus/chemistry , Furans/isolation & purification , Male , Molecular Structure , Spermatozoa/drug effects , Strongylocentrotus
2.
Nat Prod Res ; 35(1): 131-134, 2021 Jan.
Article in English | MEDLINE | ID: mdl-31242774

ABSTRACT

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.


Subject(s)
Antineoplastic Agents/pharmacology , Aspergillus/chemistry , Pyrones/chemistry , Pyrones/pharmacology , Antineoplastic Agents/chemistry , Cell Line, Tumor , Drug Resistance, Neoplasm , Drug Screening Assays, Antitumor , Humans , Magnetic Resonance Spectroscopy , Male , Molecular Structure , Prostatic Neoplasms/drug therapy , Prostatic Neoplasms/pathology
3.
Nat Prod Res ; 34(18): 2589-2594, 2020 Sep.
Article in English | MEDLINE | ID: mdl-30623671

ABSTRACT

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).


Subject(s)
Aspergillus/chemistry , Geologic Sediments/chemistry , Neuroprotective Agents/isolation & purification , Animals , Antiparkinson Agents/isolation & purification , Cell Line , Fungi/chemistry , Geologic Sediments/microbiology , Humans , Magnetic Resonance Spectroscopy , Mass Spectrometry , Mice , Models, Biological , Molecular Structure , Neuroprotective Agents/chemistry , Neuroprotective Agents/pharmacology , Oxidopamine/adverse effects , Parkinsonian Disorders/chemically induced , Parkinsonian Disorders/drug therapy , Parkinsonian Disorders/pathology , Vietnam
4.
Nat Prod Res ; 34(8): 1118-1123, 2020 Apr.
Article in English | MEDLINE | ID: mdl-30663353

ABSTRACT

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.


Subject(s)
Diketopiperazines/isolation & purification , Penicillium/chemistry , Alkaloids/chemistry , Alkaloids/isolation & purification , Cell Line, Tumor , Cytotoxins/chemistry , Cytotoxins/isolation & purification , Cytotoxins/pharmacology , Diketopiperazines/chemistry , Humans , Molecular Conformation , Molecular Structure , Spectrum Analysis
5.
Mar Drugs ; 17(11)2019 Oct 29.
Article in English | MEDLINE | ID: mdl-31671910

ABSTRACT

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.


Subject(s)
Acremonium/chemistry , Diterpenes/chemistry , Glycosides/chemistry , Glycosides/pharmacology , Macrophages/drug effects , Animals , Diterpenes/isolation & purification , Fungi , Glycosides/isolation & purification , Holothuria/microbiology , Lipopolysaccharides , Mice , Molecular Structure , Nitric Oxide , Reactive Oxygen Species , Urease/drug effects
6.
Mar Drugs ; 17(11)2019 Nov 18.
Article in English | MEDLINE | ID: mdl-31752168

ABSTRACT

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.


Subject(s)
Antineoplastic Agents/pharmacology , Macrophages/drug effects , Penicillium/chemistry , Sesquiterpenes/pharmacology , Animals , Antineoplastic Agents/chemistry , Antineoplastic Agents/isolation & purification , Cell Line, Tumor , Cells, Cultured , Circular Dichroism , Drug Screening Assays, Antitumor , Humans , Macrophages/metabolism , Mice , Mice, Inbred BALB C , Nitric Oxide/metabolism , Reactive Oxygen Species/metabolism , Sesquiterpenes/chemistry , Sesquiterpenes/isolation & purification
7.
Mar Drugs ; 17(10)2019 Oct 11.
Article in English | MEDLINE | ID: mdl-31614563

ABSTRACT

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.


Subject(s)
Antineoplastic Agents/pharmacology , Aquatic Organisms/metabolism , Aspergillus/metabolism , Biological Products/pharmacology , Fungi/metabolism , Animals , Cell Line, Tumor , Drug Screening Assays, Antitumor/methods , Geologic Sediments/microbiology , Humans , MCF-7 Cells , Magnetic Resonance Spectroscopy/methods , Marine Biology/methods , Mice , Polycyclic Sesquiterpenes/pharmacology , Polyketides/pharmacology , Sesquiterpenes/pharmacology
8.
Mar Drugs ; 16(7)2018 Jul 09.
Article in English | MEDLINE | ID: mdl-29987238

ABSTRACT

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.


Subject(s)
Antineoplastic Agents/pharmacology , Aspergillus/chemistry , Diterpenes/pharmacology , Indole Alkaloids/pharmacology , Urochordata/microbiology , Animals , Antineoplastic Agents/chemistry , Antineoplastic Agents/isolation & purification , Apoptosis/drug effects , Aquatic Organisms/microbiology , Cell Line, Tumor , Diterpenes/chemistry , Diterpenes/isolation & purification , Docetaxel , Drug Screening Assays, Antitumor , Humans , Indole Alkaloids/chemistry , Indole Alkaloids/isolation & purification , Molecular Structure , Stereoisomerism , Taxoids/pharmacology
9.
J Antibiot (Tokyo) ; 71(10): 846-853, 2018 10.
Article in English | MEDLINE | ID: mdl-29884864

ABSTRACT

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.


Subject(s)
Ascomycota/metabolism , Aspergillus/metabolism , Coculture Techniques , Indole Alkaloids/metabolism , Antineoplastic Agents/chemistry , Antineoplastic Agents/metabolism , Antineoplastic Agents/pharmacology , Aquatic Organisms , Cell Line, Tumor , Cell Survival/drug effects , Humans , Indole Alkaloids/chemistry , Models, Molecular , Molecular Structure
11.
Mar Drugs ; 15(2)2017 Feb 17.
Article in English | MEDLINE | ID: mdl-28218691

ABSTRACT

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.


Subject(s)
Antineoplastic Agents/pharmacology , Aquatic Organisms/chemistry , Autophagy/drug effects , Penicillium/chemistry , Polyketides/pharmacology , Animals , Antineoplastic Agents/chemistry , Antineoplastic Agents/isolation & purification , Cell Line, Tumor , Crystallography, X-Ray , Humans , Mice , Molecular Structure , Nitric Oxide/metabolism , Nuclear Magnetic Resonance, Biomolecular , Polyketides/chemistry , Polyketides/isolation & purification , RAW 264.7 Cells , Zosteraceae/microbiology
12.
J Nat Prod ; 79(12): 3031-3038, 2016 Dec 23.
Article in English | MEDLINE | ID: mdl-28006908

ABSTRACT

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.


Subject(s)
Antineoplastic Agents/isolation & purification , Penicillium/chemistry , Polyketides/isolation & purification , Antineoplastic Agents/chemistry , Antineoplastic Agents/pharmacology , Drug Screening Assays, Antitumor , HCT116 Cells , Humans , Molecular Structure , Nuclear Magnetic Resonance, Biomolecular , Polyketides/chemistry , Polyketides/pharmacology , Sargassum/microbiology
13.
Mar Drugs ; 14(7)2016 Jun 27.
Article in English | MEDLINE | ID: mdl-27355960

ABSTRACT

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.


Subject(s)
Biological Products/chemistry , Diterpenes/chemistry , Fungi/chemistry , Penicillium/chemistry , Piperazines/chemistry , Biological Products/pharmacology , Cell Line, Tumor , Diterpenes/pharmacology , Drug Screening Assays, Antitumor , Humans , Marine Biology/methods , Molecular Structure , Piperazines/pharmacology
14.
Nat Prod Commun ; 11(2): 207-10, 2016 Feb.
Article in English | MEDLINE | ID: mdl-27032203

ABSTRACT

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.


Subject(s)
Benzopyrans/chemistry , Benzopyrans/pharmacology , Penicillium/chemistry , Spiro Compounds/chemistry , Spiro Compounds/pharmacology , Antineoplastic Agents/chemistry , Antineoplastic Agents/pharmacology , Cell Line, Tumor , Cell Proliferation/drug effects , Humans , Molecular Structure
15.
Nat Prod Commun ; 10(7): 1247-50, 2015 Jul.
Article in English | MEDLINE | ID: mdl-26411022

ABSTRACT

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.


Subject(s)
Aspergillus/chemistry , Polyketides/isolation & purification , Animals , Aspergillus/metabolism , Cell Line, Tumor , Drug Screening Assays, Antitumor , Geologic Sediments/microbiology , Mice , Molecular Structure , Polyketides/chemistry
16.
Mar Drugs ; 12(12): 5930-43, 2014 Dec 09.
Article in English | MEDLINE | ID: mdl-25501795

ABSTRACT

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.


Subject(s)
Fungi/chemistry , Furans/chemistry , Furans/pharmacology , Penicillium/chemistry , Phaeophyceae/microbiology , Spiro Compounds/chemistry , Spiro Compounds/pharmacology , Animals , Magnetic Resonance Spectroscopy/methods , Mice , Transcription Factor AP-1/metabolism
17.
Nat Prod Commun ; 9(6): 835-6, 2014 Jun.
Article in English | MEDLINE | ID: mdl-25115093

ABSTRACT

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.


Subject(s)
Ascomycota/chemistry , Benzopyrans/chemistry , Germination/drug effects , Plants/drug effects , Seeds/drug effects , Benzopyrans/pharmacology , Molecular Structure
18.
J Nat Prod ; 77(6): 1321-8, 2014 Jun 27.
Article in English | MEDLINE | ID: mdl-24911656

ABSTRACT

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.


Subject(s)
Alkynes/isolation & purification , Antineoplastic Agents/isolation & purification , Benzopyrans/isolation & purification , Depsipeptides/isolation & purification , Geologic Sediments/chemistry , Hypocreales/chemistry , Alkynes/chemistry , Alkynes/pharmacology , Antineoplastic Agents/chemistry , Antineoplastic Agents/pharmacology , Benzopyrans/chemistry , Benzopyrans/pharmacology , Cell Survival/drug effects , Crystallography, X-Ray , Depsipeptides/chemistry , Drug Screening Assays, Antitumor , HL-60 Cells , Humans , Marine Biology , Microbial Sensitivity Tests , Molecular Conformation , Molecular Structure , Nuclear Magnetic Resonance, Biomolecular , Oceans and Seas
19.
J Nat Prod ; 77(6): 1390-5, 2014 Jun 27.
Article in English | MEDLINE | ID: mdl-24852445

ABSTRACT

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.


Subject(s)
Penicillium/chemistry , Terpenes/isolation & purification , Animals , Aspergillus/chemistry , Drug Screening Assays, Antitumor , Japan , Mice , Molecular Structure , Nuclear Magnetic Resonance, Biomolecular , Oceans and Seas , Sargassum/microbiology , Terpenes/chemistry , Terpenes/pharmacology , Transcription Factor AP-1/drug effects
20.
Nat Prod Commun ; 8(8): 1071-4, 2013 Aug.
Article in English | MEDLINE | ID: mdl-24079169

ABSTRACT

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.


Subject(s)
Alkaloids/isolation & purification , Aspergillus/metabolism , Laminaria/microbiology , Alkaloids/chemistry , Animals , Aspergillus/chemistry , Drug Screening Assays, Antitumor , Mice , Molecular Structure
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