New Antiproliferative Compounds against Glioma Cells from the Marine-Sourced Fungus Penicillium sp. ZZ1750

Seven novel compounds, namely peniresorcinosides A–E (1–5), penidifarnesylin A (6), and penipyridinone A (7), together with the 11 known ones 8–17, were isolated from a culture of the marine-associated fungus Penicillium sp. ZZ1750 in rice medium. The structures of the new compounds were established based on their high-resolution electrospray ionization mass spectroscopy (HRESIMS) data, extensive nuclear magnetic resonance (NMR) spectroscopic analyses, chemical degradation, Mosher’s method, 13C-NMR calculations, electronic circular dichroism (ECD) calculations, and single crystal X-ray diffraction. Peniresorcinosides A (1) and B (2) are rare glycosylated alkylresorcinols and exhibited potent antiglioma activity, with IC50 values of 4.0 and 5.6 µM for U87MG cells and 14.1 and 9.8 µM for U251 cells, respectively.

Trypan blue removal from water with zein sorbents and laccase

Zein-based materials were used to remove Trypan blue from water under flow conditions and in batch tests. In flow tests, zein dissolved at pH = 13 was injected in sand columns and subsequently coagulated with CaCl2, to create an adsorbent filter which removed over 99% of Trypan blue. Batch tests were conducted using zein powder, zein dissolved at pH = 13 and coagulated with CaCl2, Fe2Cl3 or citric acid, and zein dissolved in ethanol and then coagulated with water. The highest Trypan blue removal was achieved with zein powder (4000 mg Trypan blue/kg sorbent, as determined through spectrophotometry), followed by zein coagulated with Fe2Cl3 (500 mg Trypan blue/kg sorbent) and with other salts (140 mg Trypan blue/kg sorbent). Differences in the sorption efficiency are attributed to differences in the surface area. The sorption isotherm of Trypan blue onto zein-based sorbents was a Type II isotherm, suggesting physisorption. Desorption of Trypan blue was limited when zein-based coagulated sorbents were immersed in pure water. Trypan blue could be degraded by free laccase in water, as determined through spectrophotometry and electrospray ionization mass spectroscopy (ESI-MS). Trypan blue could also be degraded by laccase when zein-based laccase-containing sorbents were prepared at pH = 10, using Fe2Cl3 as coagulant. Graphic abstract

Discovery of New Secondary Metabolites by Epigenetic Regulation and NMR Comparison from the Plant Endophytic Fungus Monosporascus eutypoides

Overexpression of the histone acetyltransferase and the 1H NMR spectroscopic experiments of the endophytic fungus Monosporascus eutypoides resulted in the isolation of two new compounds, monosporasols A (1) and B (2), and two known compounds, pestaloficin C (3) and arthrinone (4). Their planar structures and absolute configurations were determined by spectroscopic analysis including high resolution electrospray ionization mass spectroscopy (HRESIMS), one-dimensional (1D) and two-dimensional (2D) NMR, and calculated electronic circular dichroism data. Compounds 1–2 were screened in cytotoxic bioassays against HeLa, HCT-8, A549 and MCF-7 cells. Our work highlights the enormous potential of epigenetic manipulation along with the NMR comparison as an effective strategy for unlocking the chemical diversity encoded by fungal genomes.

Discovery of Dihydrophaseic Acid Glucosides from the Florets of Carthamus tinctorius

Carthamus tinctorius L. (Compositae; safflower or Hong Hua) has been used in Korean traditional medicine for maintaining the homeostasis of body circulation. Phytochemical investigation was performed on the florets of C. tinctorius by liquid chromatography–mass spectrometry (LC/MS), which afforded two dihydrophaseic acid glucosides (1 and 2). Isolated compounds were structurally confirmed using a combination of spectroscopic methods including 1D and 2D nuclear magnetic resonance and high-resolution electrospray ionization mass spectroscopy. Their absolute configurations were established by quantum chemical electronic circular dichroism calculations and enzymatic hydrolysis. The anti-adipogenesis activity of the isolated compounds was evaluated using 3T3-L1 preadipocytes. Treatment with the dihydrophaseic acid glucoside (1) during adipocyte differentiation prevented the accumulation of lipid droplets and reduced the expression of adipogenic genes, Fabp4 and Adipsin. However, compound 2 did not affect adipogenesis. Our study yielded a dihydrophaseic acid glucoside derived from C. tinctorius, which has potential advantages for treating obesity.

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 μg/mL.

Two New Compounds from Rhizomes of Musa basjoo

Two new compounds, rel-(3 S,4a R,10b R)-3-(4′-methoxyphenyl)-8-hydroxy-9-methoxy-4a,5,6,10b-tetrahydro-3 H-naphtho[2,1-b]pyran (1), 7-hydroxy- 2-phenylnaphthalene-1-carboxylic acid ethyl ester (2), were isolated from the 70% ethanol extract of the rhizomes of Musa basjoo. Their structures were determined on the basis of spectroscopic analysis including 1-dimensional (1D), 2D nuclear magnetic resonance and high-resolution electrospray ionization mass spectroscopy.

Two New Neo-debromoaplysiatoxins—A Pair of Stereoisomers Exhibiting Potent Kv1.5 Ion Channel Inhibition Activities

A pair of stereoisomers possessing novel structures with 6/6/5 fused-ring systems, neo-debromoaplysiatoxin E (1) and neo-debromoaplysiatoxin F (2), were isolated from the marine cyanobacterium Lyngbya sp. Their structures were elucidated using various spectroscopic techniques including high resolution electrospray ionization mass spectroscopy (HRESIMS) and nuclear magnetic resonance (NMR). The absolute stereochemistry was determined by calculated electronic circular dichroism (ECD) and gauge-independent atomic orbital (GIAO) NMR shift calculation followed by DP4+ analysis. Significantly, this is the first report on aplysiatoxin derivatives with different absolute configurations at C9–C12 (1: 9S, 10R, 11S, 12S; 2: 9R, 10S, 11R, 12R). Compounds 1 and 2 exhibited potent blocking activities against Kv1.5 with IC50 values of 1.22 ± 0.22 μM and 2.85 ± 0.29 μM, respectively.

Chemical Constituents and Their Activities From the Seeds of Ormosia hosiei

A new cytisine-like alkaloid, hosimonoal (1), with a fused monoterpene group, and 6 known compounds (2-6) were isolated from the seeds of Ormosia hosiei Hemsl. et Wils. The structure of the new compound was confirmed by high resolution electrospray ionization mass spectroscopy (HRESIMS), 1D and 2D nuclear magnetic resonance (NMR) spectroscopy, and electronic circular dichroism, and the others by 1H and 13C NMR spectroscopy and comparison with the literature data. In addition, compounds 1, 2, 3, and 6 showed moderate cytotoxic effects against A2780, A-549, HepG2, and MCF-7 cell lines with IC50 values ranging from 5.7 to 36.5 μM.

Fe(III)-doxycycline complexes with diimine ligands: Syntheses, characterization and biological properties

Three new iron(III) complexes of doxycycline viz: [Fe(dox)2Cl]Cl2 (1), [Febpy(dox)Cl]Cl2 (2) and [Fephen(dox)Cl]Cl2 (3), where dox is doxycycline, bpy is 2,2ʹ-bipyridine and phen is 1,10-phenanthroline, were synthesized and characterized by elemental analysis, electronic absorption, FT-IR, and electrospray ionization mass spectroscopy. Doxycycline and the polypyridyl ligands behave as bidendate ligands; the polypyridyl ligands coordinate through the two diimine nitrogen atoms and doxycycline through enolate and diketoamide oxygen atoms of ring A in a five-coordinate system with chloride atom in the axial position. Their antibacterial and antiplasmodial activities against chloroquine-sensitive Plasmodium falciparum NF54 and their interaction with calf thymus (CT) DNA using electronic titration were investigated. The three complexes showed good activity against strains of Staphylococcus aureus and Klebsiella pneumonia. The complexes bind moderately to CT DNA with binding constants of 5.6 × 104 and 4.8 × 104 for complexes 2 and 3, respectively.

Novel Bioactive Penicipyrroether A and Pyrrospirone J from the Marine-Derived Penicillium sp. ZZ380

The marine-sourced fungus Penicillium sp. ZZ380 was previously reported to have the ability to produce a series of new pyrrospirone alkaloids. Further investigation on this strain resulted in the isolation and identification of novel penicipyrroether A and pyrrospirone J. Each of them represents the first example of its structural type, with a unique 6/5/6/5 polycyclic fusion that is different from the 6/5/6/6 fused ring system for the reported pyrrospirones. Their structures were elucidated by extensive nuclear magnetic resonance (NMR) and high resolution electrospray ionization mass spectroscopy (HRESIMS) spectroscopic analyses, electronic circular dichroism (ECD) and 13C NMR calculations and X-ray single crystal diffraction. Penicipyrroether A showed potent antiproliferative activity against human glioma U87MG and U251 cells with half maximal inhibitory concentration (IC50) values of 1.64–5.50 μM and antibacterial inhibitory activity with minimum inhibitory concentration (MIC) values of 1.7 μg/mL against methicillin-resistant Staphylococcus aureus and 3.0 μg/mL against Escherichia coli.