Antimicrobial metabolites from the Indonesian mangrove sediment-derived fungus Penicillium chrysogenum sp. ZZ1151.

A total of 14 compounds including a novel tetrasubstituted benzene derivative peniprenylphenol A were isolated from a scaled-up culture of the Indonesian mangrove sediment-derived fungus Penicillium chrysogenum ZZ1151 in rice medium. Structures of the isolated compounds were determined based on their NMR spectroscopic analyses, HRESIMS data, optical rotation calculations and comparison with the reported data. New peniprenylphenol A (1) was found to have antimicrobial activities against human pathogenic methicillin-resistant Staphylococcus aureus (MRSA), Escherichia coli and Candida albicans with MIC values of 6, 13, and 13 µg/mL, respectively. The known compounds of penicimumide (2), preparaherquamide (5), uridine (6), thymine (7), 1,2-seco-trypacidin (8) communol G (9), clavatol (10), 4-hydroxybenzeneacetic acid methyl ester (11), 2,5-dihydroxyphenylacetic acid methyl ester (12), 2-hydroxyphenylacetic acid methyl ester (13) and 4-hydroxyphenylethanone (14) showed antimicrobial activity against at least one of the three tested pathogens with MIC values of 3-25 µg/mL.

New Hygrocins K-U and Streptophenylpropanamide A and Bioactive Compounds from the Marine-Associated Streptomyces sp. ZZ1956.

Marine-derived Streptomyces actinomycetes are one of the most important sources for the discovery of novel bioactive natural products. This study characterized the isolation, structural elucidation and biological activity evaluation of thirty compounds, including twelve previously undescribed compounds, namely hygrocins K-U (5-13, 17 and 18) and streptophenylpropanamide A (23), from the marine-associated actinomycete Streptomyces sp. ZZ1956. Structures of the isolated compounds were determined by a combination of extensive NMR spectroscopic analyses, HRESIMS data, the Mosher's method, ECD calculations, single crystal X-ray diffraction and comparison with reported data. Hygrocins C (1), D (2), F (4), N (8), Q (11) and R (12), 2-acetamide-6-hydroxy-7-methyl-1,4-naphthoquinone (22), echoside C (27), echoside A (28) and 11,11'-O-dimethylelaiophylin (30) had antiproliferative activity (IC50: 0.16-19.39 µM) against both human glioma U87MG and U251 cells with hygrocin C as the strongest active compound (IC50: 0.16 and 0.35 µM, respectively). The analysis of the structure-activity relationship indicated that a small change in the structures of the naphthalenic ansamycins had significant influence on their antiglioma activities. Hygrocins N (8), O (9), R (12), T (17) and U (18), 2-amino-6-hydroxy-7-methyl-1,4-naphthoquinone (21), 2-acetamide-6-hydroxy-7-methyl-1,4-naphthoquinone (22), 3'-methoxy(1,1',4',1″-terphenyl)-2',6'-diol (26), echoside C (27) and echoside A (28) showed antibacterial activity against methicillin-resistant Staphylococcus aureus and Escherichia coli with MIC values of 3-48 µg/mL.

Copper ferrite nanoparticles loaded on reduced graphene oxide nanozymes for the ultrasensitive colorimetric assay of chromium ions.

Nowadays, due to the increasing threat of heavy metal ion pollution faced by the environment and living systems, the development of rapid and highly selective methods for the detection of chromium ions (Cr3+) has aroused increasing interest. In this study, copper ferrite nanoparticles (CuFe2O4) immobilized on reduced graphene oxide (CuFe2O4/rGO) were successfully fabricated by a simple co-precipitation method. The catalyst exhibits high peroxidase-like activity with 3,3',5,5'-tetramethylbenzidine (TMB) as a chromogenic matrix due to its large specific surface area, adsorption performance and abundant catalytic active sites. Based on the excellent peroxidase-like activity of CuFe2O4/rGO and its Cr3+-mediated inhibition controllability, a novel colorimetric assay for the heavy metal Cr3+ was created for the first time. Under optimal experimental conditions, CuFe2O4/rGO can be used as a peroxidase-like nanozyme to achieve the excellent detection of Cr3+ in the range of 0.1-25 µM, and the detection limit is 35 nM. The peroxidase-like CuFe2O4/rGO can provide a general catalytic platform for the application of biomimetic enzymatic catalytic systems and colorimetry, and a new approach has been established for the specific determination of the heavy metal Cr3+.

Cytotoxic metabolites from the marine-associated Streptomyces sp. ZZ1944.

Marine-derived actinomycetes from the genus Streptomycete have a huge potential for the production of metabolites with structural and bioactive uniqueness and diversity. This study described the isolation and structural elucidation of twenty metabolites, including seven previously unreported compounds galbonolide H, galbonolide I, streptophenylpropionic acid A, treptophenylpropyl ester A, streptophenvaleramide A, seco-geldanamycin A and streptorapamycin A, from the marine-associated Streptomycete sp. ZZ1944. Structures of the isolated compounds were elucidated by a combination of extensive NMR spectroscopic analyses, HRESIMS data, optical rotation and ECD calculations. The structure of galbonolide H was also confirmed by a single crystal X-ray diffraction. Both autolytimycin and seco-geldanamycin A showed potent activity against the proliferation of glioma, lung cancer, colorectal cancer and breast cancer cells. Autolytimycin blocked cell cycle of glioma cells and seco-geldanamycin A induced apoptosis of glioma cells.

Single-atom palladium anchored N-doped carbon towards oxygen electrocatalysis for rechargeable Zn-air batteries.

Herein, an atomically dispersed palladium catalyst on a hierarchical porous structure of N-doped carbon (Pd1/N-C) is prepared using a facile freeze-drying-assisted strategy. Freeze-drying methods not only suppress the aggregation of Pd atoms but also successfully produce abundant nanopores. HAADF-STEM confirms that Pd single atoms are uniformly anchored on the N-C surface. The Pd1/N-C electrocatalyst enhances the ORR and OER activity and durability compared to N-C and Pd-NPs/N-C. Rechargeable Zn-air batteries (ZABs) based on novel Pd1/N-C exhibit a peak power density of 113.7 mW cm-2 and maintain a voltage efficiency of 64.0% after 495 cycles at a discharge current density of 5 mA cm-2. Besides, two ZABs in series can supply an LED light for at least 170 h.

Talaromydien a and talaroisocoumarin A, new metabolites from the marine-sourced fungus Talaromyces sp. ZZ1616.

New talaromydien A (1) and talaroisocoumarin A (2), together with nine known compounds (3 - 11), were isolated from a culture of the marine-derived Talaromyces sp. ZZ1616 in potato dextrose broth medium. Structures of the new compounds were elucidated based on their HRESIMS data, NMR spectroscopic analyses, the modified Mosher's method, ECD, 13C NMR and optical rotation calculations. Talaroisocoumarin A showed antimicrobial activities with MIC values of 36.0 µg/mL against methicillin-resistant Staphylococcus aureus, 32.0 µg/mL against Escherichia coli, and 26.0 µg/mL against Candida albicans.

Isolation, structural elucidation, and antimicrobial evaluation of the metabolites from a marine-derived fungus Penicillium sp. ZZ1283.

A crude extract prepared from a culture of marine-sourced fungus Penicillum ZZ1283 in the medium of potato dextrose broth was found to have antimicrobial activities. Chemical investigation on this active extract resulted in the isolation of eighteen metabolites, including purpuride D, a new analogue of drimane-type sesquiterpene lactones conjugated with N-acetyl-L-valine. Structure of the new purpuride D was determined based on its HRESIMS data, NMR spectroscopic analyses, single-crystal X-ray diffraction and ECD calculation. Purpuride D showed activities in inhibiting the growth of methicillin-resistant Staphylococcus aureus, Escherichia coli and Candida albicans with MIC values of 4, 3 and 8 µg/mL, respectively.

A new antimicrobial indoloditerpene from a marine-sourced fungus aspergillus versicolor ZZ761.

A new indoloditerpene (1) and fifteen known compounds (2-16) were isolated from a marine-derived fungus Aspergillus versicolor ZZ761. Structure of the new compound was elucidated as (3 R,9S,12R,13S,17S,18S)-2-carbonyl-3-hydroxylemeniveol based on its HRESIMS data, NMR spectroscopic analyses, the Mosher's method, and ECD calculation. This new indoloditerpene (1) showed antimicrobial activities with MIC values of 20.6 µM against Escherichia coli and 22.8 µM against Candida albicans. Diorcinol (2) and versicolorin B (6) had activities in inhibiting the proliferation of human glioma U87MG and U251 cells with IC50 values of 4.4 and 6.2 µM and 11.3 and 30.5 µM, respectively.

Bioactive Alkaloids from the Actinomycete Actinoalloteichus sp. ZZ1866.

The new alkaloids marinacarbolines E-Q (1-10, 12-14), caerulomycin N (15), and actinoallonaphthyridine A (16), together with the known marinacarboline C (11) and cyanogramide (17), were isolated from the actinomycete Actinoalloteichus sp. ZZ1866. The structures of the isolated compounds were elucidated based on their HRESIMS data, extensive NMR spectroscopic analyses, Mosher's method, ECD calculations, single-crystal X-ray diffraction analysis, and chemical degradation studies. Marinacarbolines E-L (1-8) share an indole-pyridone-imidazole tetracyclic skeleton, which is the first example of this kind of skeleton. Caerulomycin N (15) and cyanogramide (17) exhibited cytotoxic activity against both human glioma U251 and U87MG cells with IC50 values of 2.0-7.2 µM. Marinacarbolines E (1), G (3), I (5), and M (9) showed cytotoxic activity against U87MG cells with IC50 values of 2.3-8.9 µM.

New Antifungal Metabolites from the Mariana Trench Sediment-Associated Actinomycete Streptomyces sp. SY1965.

New streptothiazolidine A (1), streptodiketopiperazines A (2) and B (3), and (S)-1-(3-ethylphenyl)-1,2-ethanediol (4), together with eight known compounds (5-12), were isolated from the Mariana Trench sediment-associated actinomycete Streptomyces sp. SY1965. The racemic mixtures of (±)-streptodiketopiperazine (2 and 3) and (±)-1-(3-ethylphenyl)-1,2-ethanediol (4 and 5) were separated on a chiral high-performance liquid chromatography (HPLC) column. Structures of the new compounds were elucidated by their high-resolution electrospray ionization mass spectroscopy (HRESIMS) data and extensive nuclear magnetic resonance (NMR) spectroscopic analyses. Streptothiazolidine A is a novel salicylamide analogue with a unique thiazolidine-contained side chain and its absolute configuration was established by a combination of nuclear Overhauser effect spectroscopy (NOESY) experiment, electronic circular dichroism (ECD) and 13C NMR calculations. New streptothiazolidine A (1) and streptodiketopiperazines A (2) and B (3) showed antifungal activity against Candida albicans with MIC values of 47, 42, and 42 g/mL, respectively.

Bioactive Metabolites from the Mariana Trench Sediment-Derived Fungus Penicillium sp. SY2107.

Mariana Trench sediments are enriched in microorganisms, however, the structures and bioactivities of their secondary metabolites are not very known. In this study, a fungus Penicillium sp. SY2107 was isolated from a sample of Mariana Trench sediment collected at a depth of 11000 m and an extract prepared from the culture of this fungus in rice medium showed antimicrobial activities. Chemical investigation on this active extract led to the isolation of 16 compounds, including one novel meroterpenoid, named andrastone C. Structure of the new compound was elucidated based on high-resolution electrospray ionization mass spectroscopy (HRESIMS) data, extensive nuclear magnetic resonance (NMR) spectroscopic analyses and a single crystal X-ray diffraction. The crystal structure of a known meroterpenoid andrastone B was also reported in this study. Both andrastones B and C exhibited antimicrobial activities against methicillin-resistant Staphylococcus aureus (MRSA), Escherichia coli, and Candida albicans with minimum inhibitory concentration (MIC) values in a range from 6 to 13 g/mL.

New metabolites from the marine-derived bacterium Pseudomonas sp. ZZ820R.

Six previously undescribed compounds, named monaxanthones A and B, monaphenol A, monathioamide A, monaprenylindole A, and monavalerolactone A, were isolated from the culture of a marine-sourced bacterium Pseudomonas sp. ZZ820R in rice medium. Their structures were elucidated based on the HRESIMS data, NMR and MS-MS spectroscopic analyses, optical rotation and ECD calculations. Monathioamide A is an unprecedented sulfur-contained compound and monavalerolactone A represents the first example of this type of natural products. Monaprenylindole A showed antibacterial activity against methicillin-resistant Staphylococcus aureus.

Bioactive Streptoglutarimides A-J from the Marine-Derived Streptomyces sp. ZZ741.

The new streptoglutarimides A-J (1-10) and the known streptovitacin A (11) were isolated from a marine-derived actinomycete, Streptomyces sp. ZZ741. Structures of the isolated compounds were elucidated based on their HRESIMS data, extensive NMR spectroscopic analyses, ECD calculations, Mosher's method, and a single-crystal X-ray diffraction experiment. Streptoglutarimide H (8) and streptovitacin A (11) showed potent antiproliferative activity against human glioma U87MG and U251 cells with IC50 values of 1.5-3.8 µM for 8 and 0.05-0.22 µM for 11. All isolated compounds exhibited antimicrobial activity with MIC values of 9-11 µg/mL against methicillin-resistant Staphylococcus aureus, 8-12 µg/mL against Escherichia coli, and 8-20 µg/mL against Candida albicans.

Novel Antimicrobial Indolepyrazines A and B from the Marine-Associated Acinetobacter sp. ZZ1275.

Two new alkaloids indolepyrazines A (1) and B (2) were isolated from the marine-derived Acinetobacter sp. ZZ1275. Their structures were elucidated through extensive nuclear magnetic resonance (NMR) spectroscopic analyses, high resolution electrospray ionization mass spectroscopy (HRESIMS) data, and electronic circular dichroism (ECD) calculation. Indolepyrazine A represents the first example of alkaloids with an indole-pyrazine-oxindole skeleton. Both 1 and 2 showed antimicrobial activities against methicillin-resistant Staphylococcus aureus, Escherichia coli, and Candida albicans with minimum inhibitory concentration (MIC) values of 12 µg/mL, 8⁻10 µg/mL, and 12⁻14 µg/mL, respectively.

Peniciphenalenins A-F from the culture of a marine-associated fungus Penicillium sp. ZZ901.

Marine-derived fungi of the genus Penicillium represent a huge potential for synthesizing the secondary metabolites with structural and bioactive uniqueness and diversity. In this study, six previously undescribed compounds peniciphenalenins A-F and four known compounds (+)-sclerodin, (+)-scleroderolide, (+)-sclerodione, and physcion were isolated from the culture of a marine-derived fungus Penicillium sp. ZZ901. Structures of the isolated compounds were elucidated by a combination of extensive NMR spectroscopic analysis, HRESIMS data, optical rotation value, ECD calculation, and single crystal X-ray diffraction. Peniciphenalenins A-C are the second examples of the type of neoherqueinones. The possible biosynthetic route of nine phenalenone derivatives has been suggested. The known (+)-scleroderolide showed both antiproliferative activity against glioma cells with IC50 values of 23.24-37.26 µM and antibacterial activity in suppressing the growth of methicillin-resistant Staphylococcus aureus and Escherichia coli with MIC values of 7.0 and 9.0 µg/mL, respectively.

Flexible 3D carbon nanotubes cuff electrodes as a peripheral nerve interface.

The cuff electrode provides a stable interface with peripheral nerves, which has been widely used in basic research and clinical practice. Currently, the cuff electrodes are limited by the planar processing of microfabrication. This paper presents a novel cuff electrode using high-aspect ratio carbon nanotubes (CNTs) integrated on a flexible biocompatible parylene. The microfabrication process unites the high quality vertical CNTs grown at high temperature with the heat sensitive parylene substrate in a highly controllable manner. The fabricated cuff electrodes have been utilized for extracellular nerve stimulation in rats. The experimental results demonstrate the proposed CNT electrode has a better performance than Pt electrode in nerve stimulation. Moreover, the effect of electrode position and stimulation frequency is demonstrated in this paper. This preliminary data indicates that flexible 3D CNTs cuff electrode provides an excellent platform for functional electrical stimulation.

3D carbon nanofiber microelectrode arrays fabricated by plasma-assisted pyrolysis to enhance sensitivity and stability of real-time dopamine detection.

In this paper, we have fabricated 3D carbon nanofiber microelectrode arrays (MEAs) with highly reproducible and rich chemical surface areas for fast scan cyclic voltammetry (FSCV). Carbon nanofibers are created from negative photoresist by a new process called dual O2 plasma-assisted pyrolysis. The proposed approach significantly improves film adhesion and increases surface reactivity. We showcase our sensor's compatibility with FSCV analysis by demonstrating highly sensitive and stable FSCV dopamine measurements on a prototype 4-channel array. We envision with proper surface fuctionalization the 3D carbon nanofiber MEA enable sensitive and reliable detection of multiple neurotransmitters simultaneously.

A flexible and implantable microelectrode arrays using high-temperature grown vertical carbon nanotubes and a biocompatible polymer substrate.

This paper presents a novel microelectrode arrays using high-temperature grown vertically aligned carbon nanotubes (CNTs) integrated on a flexible and biocompatible parylene substrate. A simple microfabrication process is proposed to unite the high quality vertical CNTs grown at high temperature with the heat sensitive parylene substrate in a highly controllable manner. Briefly, the CNTs electrode is encapsulated by two layers of parylene and the device is released using xenon difluoride (XeF2). The process is compatible with wafer-scale post complementary metal oxide semiconductor integration. Lower impedance and larger interfacial capacitance have been demonstrated using CNTs compared to a Pt electrode. The flexible CNT electrodes have been utilized for extracellular neuronal recording and stimulation in rats. The signal-to-noise ratio of the device is about 12.5. The threshold voltage for initiating action potential is about 0.5 V.