Parazoanthus axinellae Extract Incorporated Hybrid Nanostructure and Its Potential Antimicrobial Activity.

This study, it was aimed to examine the change in the antimicrobial effect of sea anemone Parazoanthus axinellae extract by forming its nanoflowers. A scanning electron microscope (SEM) and energy dispersive X-ray spectroscopy (EDX) were expended to observe the morphologies of the Cu NFs that had been produced. Fourier transform infrared spectroscopy (FT-IR) and X-ray diffraction (XRD) techniques were expended to analyze the managing assemblies in P. axinellae extract, which perform an effective part in the synthesis routine, as well as the crystal assembly of NFs. P. axinellae extract mediated the HNFs (Hybrid nanoflowers) are at high, pure crystalline nature, flower shape with a crystallographic system at the nanoscale with mean crystallite size 21.9 nm using XRD, and average particle size ~10 nm by SEM. The broad absorption band at 2981-2915 cm-1 in the FT-IR spectra of anemone extract and Cu-anemone NFs represents the unique peak of hydroxy groups. In addition, Cu NFs were tested for their antibacterial properties. Cu NFs have been discovered to exhibit antibacterial properties. It is suggested that P. axinellae extract and various inorganic components be used to synthesize a variety of NFs and assess their suitability for usage in biomedical fields.

Synthesis of Axinyssa digitata Extract Directed Hybrid Nanoflower and Investigation of Its Antimicrobial Activity.

First time in this study, the antibacterial effects of Axinyssa digitata sponge extracts and Axinyssa digitata-based cupper hybrid nanoflowers (Cu hNFs) were evaluated. Herein, hybrid nanoflowers (Cu hNFs) were produced by combining Axinyssa digitata sponge extract with Cu2+ ions in Phosphate-buffered saline (PBS) (at pH 7.4) at room temperature for three days using green synthesis method. The shape and size of hNFs were evaluated using scanning electron microscope (SEM) images. Energy dispersive X-ray spectroscopy (EDX) mapping was used to determine the presence of Cu metals and other components. X-ray diffraction (XRD) is a non-destructive analysis method that was used to determine of the crystallographic properties of materials and the phases they contain. Fourier-transform infrared spectroscopy (FT-IR) peaks were used to discuss the presence of functional groups that played a key role in the synthesis. The Cu-hNFs had antimicrobial activity against selected microorganisms. This research is expected to provide knowledge on hNFs synthesis and antimicrobial activity application investigations using Axinyssa digitata rather than biomolecules obtained through costly and time-consuming methods.

Anti-Inflammatory, Antiallergic and COVID-19 Main Protease (Mpro) Inhibitory Activities of Butenolides from a Marine-Derived Fungus Aspergillus costaricaensis.

Amid the current COVID-19 pandemic, the emergence of several variants in a relatively high mutation rate (twice per month) strengthened the importance of finding out a chemical entity that can be potential for developing an effective medicine. In this study, we explored ethyl acetate (EtOAc) extract of a marine-derived fungus Aspergillus cosatricaensis afforded three butenolide derivatives, butyrolactones I, VI and V (1-3), two naphtho-γ-pyrones, TMC-256 A1 (4) and rubrofusarin B (5) and methyl p-hydroxyphenyl acetate (6). Structure identification was unambiguously determined based on exhaustive spectral analyses including 1D/2D NMR and mass spectrometry. The isolated compounds (1-6) were assessed for their in vitro anti-inflammatory, antiallergic, elastase inhibitory activities and in silico SARS-CoV-2 main protease (Mpro). Results exhibited that only butenolides (1 and 2) revealed potent activities similar to or more than reference drugs unlike butyrolactone V (3) suggesting them as plausible chemical entities for developing lead molecules.

Multiway resolution of spectrochromatographic measurements for the quantification of echinuline in marine-derived fungi Aspergillus chevalieri using parallel factor analysis.

A multiway resolution of incomplete chromatographic separation was presented for spectrochromatographic quantification of echinuline in marine-derived fungi Aspergillus chevalieri. Two-dimensional spectrochromatographic maps of calibration, validation and real samples were recorded as a function of time and wavelength using UPLC-PDA instrument under non-optimized chromatographic conditions, which gave rise to co-elution of echinuline and the constituents of sample matrix. A three-way array was obtained by concatenating the data matrices of the spectrochromatographic maps. Then, parallel factor analysis was applied to the multiway array to extract the individual contribution of echinuline in three modes (time, wavelength and sample). While time and wavelength profiles were used for the characterization of echinuline, the sample profile was used for its quantitative determination of the analyte in validation set and in real samples. Validity of the analytical method was evaluated by analyzing the validation set, which consist of test samples, standard addition samples, intra-day and inter-day samples. The proposed multiway analysis method was then applied to marine-derived fungi extracts and echinuline content was found to be 31.9 µg/g based on the average of ten assay results. The assay results provided by PARAFAC model were statistically compared with those obtained by a newly developed classical UPLC method, which ensured the complete separation of echinuline in a run time of nine minutes. The assay results were found to be comparable due to the fact that there was no significant difference between the analysis results (F = 1.63, Fcrit = 3.17; t = 0.69, tcrit = 2.11) at the significance level of 95%). Consequently, the PARAFAC method permitted the accurate determination of echinuline in fungal extracts despite the partial chromatographic separation with a run time of only three minutes.

Anti-Inflammatory, Antiallergic, and COVID-19 Main Protease (Mpro) Inhibitory Activities of Butenolides from a Marine-Derived Fungus Aspergillus terreus.

In December 2020, the U.K. authorities reported to the World Health Organization (WHO) that a new COVID-19 variant, considered to be a variant under investigation from December 2020 (VUI-202012/01), was identified through viral genomic sequencing. Although several other mutants were previously reported, VUI-202012/01 proved to be about 70% more transmissible. Hence, the usefulness and effectiveness of the newly U.S. Food and Drug Administration (FDA)-approved COVID-19 vaccines against these new variants are doubtfully questioned. As a result of these unexpected mutants from COVID-19 and due to lack of time, much research interest is directed toward assessing secondary metabolites as potential candidates for developing lead pharmaceuticals. In this study, a marine-derived fungus Aspergillus terreus was investigated, affording two butenolide derivatives, butyrolactones I (1) and III (2), a meroterpenoid, terretonin (3), and 4-hydroxy-3-(3-methylbut-2-enyl)benzaldehyde (4). Chemical structures were unambiguously determined based on mass spectrometry and extensive 1D/2D NMR analyses experiments. Compounds (1-4) were assessed for their in vitro anti-inflammatory, antiallergic, and in silico COVID-19 main protease (Mpro) and elastase inhibitory activities. Among the tested compounds, only 1 revealed significant activities comparable to or even more potent than respective standard drugs, which makes butyrolactone I (1) a potential lead entity for developing a new remedy to treat and/or control the currently devastating and deadly effects of COVID-19 pandemic and elastase-related inflammatory complications.

Penicacids H-J, three new mycophenolic acid derivatives from the marine-derived fungus Rhizopus oryzae.

Chemical investigation of secondary metabolites in crude methanol extract of a solid rice medium of a marine-derived fungus, Rhizopus oryzae, has enriched the metabolic profile of this genus by affording three mycophenolic acid derivatives recognized as new fungal metabolites trivially named as penicacids H-J (1-3), along with two known naphtho-γ-pyrone dimers, asperpyrone A (4) and dianhydroaurasperone C (5). Structure elucidation of isolated compounds was unambiguously determined based on extensive 1D and 2D NMR spectroscopic analyses together with comparing coupling constant and optical rotation values with those reported for related congeners in literature. All isolated compounds were assessed for their antibacterial activity against four different bacterial microorganisms and they revealed moderate to weak activities with minimum inhibitory concentration (MIC) values ranging from 62.5 to 250 µg mL-1.

Ustusaustin A: a new neuraminidase inhibitory meroterpene from the ascidian-derived endophytic fungus Aspergillus ustus TK-5.

A new austin-type meroterpene, namely, ustusaustin A (1), together with seven related known analogues (2-8), were isolated and identified from the culture extract of Aspergillus ustus TK-5, an endophytic fungus obtained from the marine ascidian Pyura momus. The structures of these compounds were established on the basis of detailed interpretation of their NMR and MS data, and the relative and absolute configurations of 1 was confirmed by X-ray crystallographic analysis. Among them, ustusaustin A (1) represents the first example of 1'-nor-austin analogues with an unique 7-benzoylation. Compounds 1-4, 6, and 7 exhibited potent neuraminidase inhibitory activity and this is the first report of neuraminidase inhibitory activity for austin-type meroterpenes.

Isolation and characterization of three pairs of indolediketopiperazine enantiomers containing infrequent N-methoxy substitution from the marine algal-derived endophytic fungus Acrostalagmus luteoalbus TK-43.

Three pairs of new N-methoxy-containing indolediketopiperazine enantiomers, acrozines A-C (1-3), were isolated from the culture extract of Acrostalagmus luteoalbus TK-43, an endophytic fungus obtained from the marine green alga Codium fragile. The optical resolution of compounds 1-3 by chiral HPLC successfully afforded individual enantiomers (+)-1/(-)-1, (+)-2/(-)-2, and (+)-3/(-)-3, respectively. The structures of all these compounds were established on the basis of detailed interpretation of their NMR and mass spectroscopic data. X-ray crystallographic analysis confirmed the structures of compounds 1-3, while the absolute configurations were determined by TDDFT-ECD calculations. All these compounds containing a N-methoxy group which is uncommon in indolediketopiperazines. The enantiomers, (+)-2/(-)-2, showed different antimicrobial activities against several plant-pathogenic fungi, while (+)-1 displayed better inhibitory activity against acetylcholinesterase than that of (-)-1.

Sorbicillinoid-Based Metabolites from a Sponge-Derived Fungus Trichoderma saturnisporum.

Antibacterial activity assessment and high performance liquid chromatography associated with nuclear magnetic resonance (HPLC/NMR) data revealed that the EtOAc extract of the fermented endophytic fungus Trichoderma saturnisporum DI-IA, obtained from the marine sponge Dictyonella incisa, contained conjugated olefinic metabolites with antibacterial activity. Chemical examination of the fungal strain resulted in the isolation of eight new sorbicillinoid-based compounds, namely saturnispols A⁻H (1⁻8). Their structures were determined on the basis of extensive spectroscopic analysis, including the experimental and calculated electronic circular dichroism (ECD) data for the configurational assignments. Saturnispol F exerted significant inhibition against a panel of bacteria strains including vancomycin-resistant enterococci (VRE) with a minimum inhibitory concentrations (MIC) ranging from 1.63 to 12.9 μg/mL, while saturnispol H showed selective effects against VRE and B. subtilis.

New Chromone, Isocoumarin, and Indole Alkaloid Derivatives from three Sponge-derived Fungal Strains.

Two new chromone derivatives, 2-hydroxymethyl-3-methyl-7-methoxychromone (1) and 2-hydroxymethyl-3-tert-butyl-7-methoxychromone (2), together with a related known compound, 2,3-dimethyl-7-methoxychromone (3), were isolated from Rhinocladiella sp. (102), a fungus obtained from the sponge Ircinia oros. Furthermore, a new isocoumarin derivative, 3-(3-chloro-2-hydroxypropyl)-8-hydroxy-6-methoxy-isochromen-I-one (4) and a known analogue 3-[(R)- 3,3-dichloro-2-hydroxypropyl]-8-hydroxy-6-methoxy-IH-isochromen-I -one (dichlorodiaportin, 5), were identified from sponge-derived fungal strain Clonostachys sp. (AP4.1), while a new indole alkaloid 1-(4-hydroxybenzoyl)indole-3-carbaldehyde (6) was obtained from the sponge-derived fungus Engyodontium album (IVB lb). The structures of these compounds were established by NMR spectroscopic and mass spectrometric data analysis, as well as by comparison with literature reports. Compounds 4 and 6 were examined for cytotoxic and antimicrobial activities, respectively. None of them showed potent activity.

Lignans in flowering aerial parts of Linum species--chemodiversity in the light of systematics and phylogeny.

The aerial parts of 54 accessions representing 41 Linum species and four species of related genera were analysed for lignans by means of HPLC-ESI/MS-MS-UV/DAD. In total, 64 different lignans of the aryltetralin-, arylnaphthalene-, aryldihydronaphthalene-, dibenzylbutyrolactone-, and furofuran type were identified. According to their lignan profile, the Linum species can be divided in two groups accumulating as major lignan types either cyclolignans of the aryltetralin-series on one hand, or aryldihydronaphthalenes/arylnaphthalenes, on the other. Five of the investigated Linum species did not contain any detectable amounts of these lignans under the chosen analytical conditions. Furthermore, none of the lignans identified in Linum species was detectable in representatives of three related genera, namely, Reinwardtia (Linaceae, Linoideae), Hugonia and Indorouchera (Linaceae, Hugonioideae). The two species groups differing in the types of the dominating cyclolignans comprise representatives of the major taxonomic sections. Representatives of sections Syllinum, Cathartolinum and Linopsis accumulate mainly aryltetralins while those of sections Linum and Dasylinum were found to contain mainly aryldihydronaphthalenes/-naphthalenes. These phytochemical data correlate very well with a recent study on the molecular phylogeny of Linum/Linaceae, where a subdivision of Linum into two major clades comprising representatives of the two mentioned groups was found. Thus, the distribution of lignans apparently reflecting phylogenetic interrelations at the infrageneric level, a plausible scenario for the evolution of lignan biosynthesis in the genus Linum can now be presented.

Hexa-, hepta- and nonaprenylhydroquinones isolated from marine sponges Sarcotragus muscarum and Ircinia fasciculata inhibit NF-kappaB signalling in H4IIE cells.

OBJECTIVES: Marine organisms have proven to be a rich source of potent pharmacologically active compounds. Three polyprenyl-1,4-hydroquinone derivates (hexaprenyl-1,4-hydroquinone, heptaprenyl-1,4-hydroquinone and nonaprenyl-1,4-hydroquinone) were isolated from the Zoobenthos-inhabiting sponges Sarcotragus muscarum and Ircinia fasciculata from the Eastern Mediterranean Sea (phylum: Porifera; class: Demospongiae). METHODS: Hexa-, hepta- and nonaprenylhydroquinone were identified by (1)H-NMR, H,H-COSY, heteronuclear multiple bond correlation, FAB-MS and UV spectroscopy. The effects of the compounds on cell viability was determined using the MTT assay; anti-oxidative potential was measured using the Trolox equivalent antioxidative capacity assay. Inhibition of nuclear factor-kappaB activity was detected by secreted alkaline phosphatase assay. Activity against an array of protein kinases was determined in 96-well FlashPlates. KEY FINDINGS: All compounds had prominent antioxidative activity, comparable to that of the synthetic vitamin E derivate Trolox. Hexaprenylhydroquinone showed the greatest cytotoxicity in H4IIE hepatoma cells (EC50 2.5 muM). All three compounds inhibited NF-kappaB signalling in this cell line, with heptaprenylhydroquinone being the most active. Screening of 23 kinases involved in signal transduction pathways (cell proliferation, survival, angiogenesis and metastasis) showed that hexaprenylhydroquinone and heptaprenylhydroquinone inhibited the activity of the epidermal growth factor receptor (IC50 1.6 and 1.4 mug/ml, respectively), and heptaprenylhydroquinone also inhibited the activity of other kinases (Src tyrosine kinase, vascular endothelial growth factor receptor 3 and insulin-like growth factor 1 receptor). CONCLUSIONS: The prenylated hydroquinones isolated from the marine sponges S. muscarum and I. fasciculata showed cytotoxic and antioxidative activities and inhibited NF-kappaB signalling in H4IIE hepatoma cells and protein kinases. These findings may result in the generation of new lead substances in cancer therapy.

Free Radical Scavenging Activity of Linum arboreum.

The methanol and water extracts of Linum arboreum.. aerial parts were screened for free radical scavenging activity. The free radical scavenging activity was determined spectrophotometrically on the basis of inhibition of cytochrome c reduction and the ability to bleach the stable radical 2,2-diphenyl-1-picrylhydrazyl (DPPH). The methanol extracts of Linum arboreum. were shown to have potent antioxidant activity.

Comparison of different extraction methods for the determination of podophyllotoxin and 6-methoxypodophyllotoxin in Linum species.

Three extraction methods for analysis of podophyllotoxin and its derivatives from Linum species were compared. No statistical difference on the percentage of recovery were found between the methods. The "glycosidase-method" showed the best result with respect to the accuracy studies; the "acetone-method" has an advantage compared to the other methods due to its capability to calculate the aglycone, lignan glycoside and total lignan. The content of podophyllotoxin and 6-methoxypodophyllotoxin in Linum mucronatum subsp. mucronatum Bertol, Linum arboreum L., and the endemic Turkey species of Linum flavum subsp. scabrinerve Davis were determined. This is the first report on the analysis of podophyllotoxin and 6-methoxy podophyllotoxin of natural collected Linum flavum subsp. scabrinerve and Linum arboreum.

Assessment of therapeutic effect of Inula heterolepsis Boiss in alcoholic rats.

An aqueous extract from the root of Inula heterolepsis Boiss was prepared and then tested for its ability to treat experimentally induced alcoholic hepatic injury in rats. Alcoholic rats were divided into two groups. The first group of rats were given 200 mg/kg/day plant extract. Repeated doses of extract preparations were given at 12 h intervals for 10 days. Differences between the recovery of tissue injury, with and without Inula plant extract, were evaluated. The second group of rats were given vehicle. Liver, testis and kidney injuries due to the chronic alcohol consumption were proven biochemically and histopathologically. Rats were killed, serum SGOT, SGPT, alkaline phosphatase, and albumin levels were measured. SGOT, SGPT and alkaline phosphatase levels were significantly higher in alcoholic rats due to the tissue damage compared with intact, vehicle and Inula treated groups of rats (p < 0.05). Liver, testis, kidneys, stomach, intestine, heart, lungs and bladder were examined histopathologically. According to our study, the root extract of Inula heterolepsis Boiss has a slight therapeutic effect on alcoholic liver, kidney and testis damage in rats. Comparing the therapeutic effects in these organs, the liver seemed to be affected meaningfully after treatment with the plant extract.