Phenylethanoid glycosides from Michelia champaca leaves.

Chemical investigation on the leaves of Michelia champaca L. (Magnoliaceae) led to the isolation of five previously undescribed phenylethanoid glycosides (PhGs), 4-O-ß-d-glucopyranosyl-acteoside (1), 4‴-O-(6-O-E-caffeoyl)-ß-d-glucopyranosyl-acteoside (2), 4‴-O-(6-O-E-caffeoyl)-ß-d-glucopyranosyl-isoacteoside (3), 6""-O-E-feruloyl-echinacoside (4), and 6""-O-p-E-coumaroyl-echinacoside (5), together with eighteen known PhGs. Their structures were determined by spectroscopic and chemical methods. All the known PhGs except acteoside (8) were not previously reported in the genus. Twenty-one PhGs exhibited more potent DPPH radical scavenging activity and FRAP than l-ascorbic acid (l-AA), and twenty-two PhGs showed better ABTS radical cation scavenging activity than l-AA. In addition, twelve PhGs displayed more potent cellular reactive oxygen species scavenging activity than curcumin. The results revealed that the leaves of M. champaca are a rich source of phenylethanoid glycosides and antioxidants.

Tumor or Demyelination? Three Tumefactive Multiple Sclerosis Case Reports and Literature Review.

OBJECTIVE: To investigate the clinical diagnosis and treatment of tumefactive multiple sclerosis (TMS). METHODS: Clinical data, laboratory and imaging examinations, and treatment of 3 patients with TMS were retrospectively analyzed. Data were further analyzed in relation to the literature. RESULTS: All 3 patients had acute or subacute onset with large lesions on imaging, which were difficult to differentiate from tumors. Two cases had relapses on follow-up and one case had a stereotactic biopsy. CONCLUSIONS: TMS is difficult to differentiate from brain tumors. It is necessary to improve the understanding of these diseases, to apply the correct diagnosis and treatment and to avoid unnecessary invasive surgery and inappropriate treatment.

Pararorine A, isoindolinone alkaloid from the endophytic fungus Paramyrothecium roridum and its anti-tumor activity.

Pararorine A, a new isoindolinone alkaloid was isolated from Paramyrothecium roridum, an endophytic fungus from the medicinal plant Gynochthodes officinalis (F.C. How) Razafim. & B. Bremer. The structure of this compound was elucidated by extensive spectroscopic (UV, IR, MS, and NMR) analyses. In addition, the antitumor activity of pararorine A was evaluated against SF-268, MCF-7, HepG2, and A549 tumor cell lines. The results revealed that pararorine A exhibited potent antitumor activities with the IC50 values ranging from 1.69 to 8.95 µM. Moreover, the tumor cell inhibitory activity of pararorine A was evidenced by promoting cytochrome C release and cell cycle arrest as well as the induction of apoptosis by the up-regulation of the protein expressions of JNK and Bax through PARP-cleavage and caspase 3-cleavage.

Irpexols A-C, xanthone derivatives from the endophyte fungus Irpex laceratus A878.

Three new xanthone derivatives irpexols A-C (1-3) and five known xanthones including three dimeric ones were successfully isolated from Irpex laceratus A878, an endophytic fungus of the family Irpicaceae from the medicinal plant Pogostemon cablin (Blanco) Bentham (Lamiaceae). The structures of these compounds were elucidated by extensive spectroscopic analyses including ultraviolet-visible spectroscopy (UV), infrared spectroscopy (IR), mass spectrometry (MS), and nuclear magnetic resonance (NMR). All of the three new compounds (1-3) share a de-aromatic and highly­oxygenated xanthone skeleton. In addition, the cytotoxic activity of compounds 1-8 were evaluated against SF-268, MCF-7, HepG2, and A549 tumor cell lines. The results revealed that compound 6 showed moderate cytotoxic activity with the IC50 values ranging from 24.83 to 45.46 µM, while the IC50 values of the positive control adriamycin was ranging from 1.11 to 1.44 µM.

Sesquiterpenes and α-pyrones from an endophytic fungus Xylaria curta YSJ-5.

Chemical investigation of the culture extract of an endophyte Xylaria curta YSJ-5 from Alpinia zerumbet (Pers.) Burtt. et Smith resulted in the isolation of eight previously undescribed compounds including five eremophilane sesquiterpenes xylarcurenes A-E, one norsesquiterpene xylarcurene F, and two α-pyrone derivatives xylarpyrones A-B together with eight known related derivatives. Their chemical structures were extensively established based on the 1D- and 2D-NMR spectroscopic analysis, modified Mosher's method, electronic circular dichroism calculations, single-crystal X-ray diffraction experiments, and the comparison with previous literature data. All these compounds were tested for in vitro cytotoxic, anti-inflammatory, α-glucosidase inhibitory, and antibacterial activities. As a result, 6-pentyl-4-methoxy-pyran-2-one was disclosed to display significant antibacterial activity against Staphylococcus aureus and methicillin-resistant S. aureus with minimal inhibitory concentration value of 6.3 µg/mL.

Chemical Constituents and Bioactivities of the Plant-Derived Fungus Aspergillus fumigatus.

A new bergamotane sesquiterpenoid, named xylariterpenoid H (1), along with fourteen known compounds (2-15), were isolated from the crude extract of Aspergillus fumigatus, an endophytic fungus isolated from Delphinium grandiflorum L. Their structures were elucidated mainly by extensive analyses of NMR and MS spectroscopic data. In addition, the screening results of antibacterial and cytotoxic activities of compounds 1-15 showed that compound 4 displayed antibacterial activities against Staphylococcus aureus and MRSA (methicillin-resistant S. aureus) with an MIC value of 3.12 µg/mL.

Regioselectivity Switch of α-Amino Acid-Derived Esters and MBH Carbonates for the Synthesis of Allyl-Substituted Azlactones.

Allylic azlactones are greatly significant in terms of potential bioactivities and synthetic applications. Owing to the burgeoning interest of the pharmaceutical industry in α-amino acid derivatives, discovering strategies for the synthesis of allylic azlactones is important. Herein, we establish a transition-metal-free regioselectivity switch of α-amino acid-derived esters and MBH carbonates, which exhibits broad reaction scope and good reaction yields. Control reactions indicate that both base and solvent are important for regioselectivity.

Analysis of Dopamine Receptor D2 Gene Polymorphism and Correlation with Dyslipidemia in the Chinese Population.

Objective: The study aimed to explore the genotype and allele distributions of dopamine D2-like receptor (DRD2) gene -141C and C957T polymorphisms in the Chinese Han population with dyslipidemia, as well as their association with serum lipid levels. Methods: One hundred fifty patients with dyslipidemia and 150 healthy people were recruited as the case and the control groups, respectively. Serum total cholesterol (TC), triglyceride (TG), high-density lipoprotein cholesterol (HDL-C), and low-density lipoprotein cholesterol levels were detected. The target sequence of DRD2 polymorphisms was amplified by polymerase chain reaction and genotyped via Sanger sequencing. Results: In DRD2 gene C957T (rs6277), three genotypes of CC, CT, and TT were detected with the frequencies of 92.67%, 6.67%, 0.67% in dyslipidemia cases, and 83.33%, 14.67%, 2.00% in the controls, respectively. The CT genotype and T allele frequencies were significantly low in the case group relative to the control group. After adjusting to other clinical indicators, the CT genotype of C957T polymorphism (hazard ratio = 0.401, 95% confidence interval = 0.181-0.890, p < 0.05) was still related to a significantly reduced risk of dyslipidemia. The C957T CT genotype carriers had the lowest values of serum TC, TG, LDL, and the highest values of serum HDL-C. Conclusion: DRD2 gene C957T polymorphism was an independent influencing factor associated with the susceptibility to dyslipidemia, and the CT genotype was associated with decreased odds of susceptibility to dyslipidemia.

Phomopamide A, a cyclic pentadepsipeptide with α-glucosidase inhibition activity from the endophytic fungus Diaporthe sp.

An undescribed cytotoxic cyclopeptide named phomopamide A (1) was isolated from Diaporthe sp., which is an endophytic fungus from Artemisia argyi. Phomopamide A (1) featured an pentadepsipeptide skeleton and composed of two Phe, one Val, one Leu, and one 2-hydroxyoctanoic acid units. The structure of this new compound was fully characterised on the basis of extensive spectroscopic analysis. Moreover, phomopamide A was evaluated for in vitro cyctotoxic and α-glucosidase inhibitory activity. As a result, phomopaminde A exhibited no cytotoxic activity against four tumour cell lines, while it showed a potent α-glucosidase inhibition effect with IC50 value of 62.35 µM.

Rosemary: Unrevealing an old aromatic crop as a new source of promising functional food additive-A review.

Rosemary (Rosmarinus officinalis L.) is one of the most famous spice plants belonging to the Lamiaceae family as a remarkably beautiful horticultural plant and economically agricultural crop. The essential oil of rosemary has been enthusiastically welcome in the whole world for hundreds of years. Now, it is wildly prevailing as a promising functional food additive for human health. More importantly, due to its significant aroma, food, and nutritional value, rosemary also plays an essential role in the food/feed additive and food packaging industries. Modern industrial development and fundamental scientific research have extensively revealed its unique phytochemical constituents with biologically meaningful activities, which closely related to diverse human health functions. In this review, we provide a comprehensively systematic perspective on rosemary by summarizing the structures of various pharmacological and nutritional components, biologically functional activities and their molecular regulatory networks required in food developments, and the recent advances in their applications in the food industry. Finally, the temporary limitations and future research trends regarding the development of rosemary components are also discussed and prospected. Hence, the review covering the fundamental research advances and developing prospects of rosemary is a desirable demand to facilitate their better understanding, and it will also serve as a reference to provide many insights for the future promotion of the research and development of functional foods related to rosemary.

Koningipyridines A and B, two nitrogen-containing polyketides from the fungus Trichoderma koningiopsis SC-5.

Two novel koninginin derivatives, koningipyridines A and B (1 and 2), along with four known compounds (3-6) were isolated from the EtOAc extract of the endophytic fungus Trichoderma koningiopsis SC-5. Among them, koningipyridine A featured an unprecedented pentacyclic ketal skeleton with the formation of a fascinating 6/6/5/6/5 fused ring system and shared a characteristic pyridine core, which represents the first example of nitrogen-containing koninginin-type natural product. Moreover, koningipyridine B was the first member in the koninginin family sharing a unique 6/6/5 dihydropyridine skeleton, and it was suggested to be the critical biosynthetic precursor of koningipyridine A. The structures of 1 and 2 were elucidated by the interpretation of 1D and 2D NMR spectroscopy, HRESIMS data, as well as theoretical calculations of 13C NMR and electronic circular dichroism (ECD). Moreover, all isolates were screened for antimicrobial activities against Staphylococcus aureus, MRSA, and Escherichia coli as well as the cytotoxic effects against three cancer cell lines (A549, Hela, and HepG2).

Bioactive ambuic acid congeners from endophytic fungus Pestalotiopsis trachicarpicola SC-J551.

New ambuic acid derivatives, pestallic acids R-V (1-5), together with ambuic acid (6), were isolated from the endophytic fungus Pestalotiopsis trachicarpicola SC-J551 derived from the fern Blechnum orientale L., of which compound 2, being racemic, was separated to two optically pure enantiomers (+)-2 and (-)-2. The structures including absolute configurations of these new compounds were elucidated by extensive spectroscopic analysis and theoretical simulations of their ECD spectra and 13C NMR chemical shifts. Compounds 1 and 3 exhibited cytotoxicity against human carcinoma A549, HeLa, HepG2, and MCF-7 cells (IC50: 3.6-12.5 µM) and compound 3 was also active against Staphylococcus aureus and MRSA (MIC = 20 µg ml-1). Compound (±)-2 showed inhibitory activity against LPS-induced NO release (IC50 = 21.1 µM) and t-BHP-induced ROS production (IC50 = 8.5 µM) in RAW264.7 macrophages.

Xylarcurcosides A-C, three novel isopimarane-type diterpene glycosides from Xylaria curta YSJ-5.

Three previously undescribed isopimarane-type diterpene glycosides named as xylarcurcosides A-C (1-3) along with two known ones 16-α-d-mannopyranosyloxyisopimar-7-en-19-oic acid (4) and hypoxylonoid A (5) were successfully isolated from an ethyl acetate extract of the endophytic fungus Xylaria curta YSJ-5 growing in leaves of Alpinia zerumbet. The spectroscopic methods, electronic circular dichroism (ECD) calculations, and X-ray diffraction experiments were conducted to identify their absolute chemical structures. All these compounds were tested for in vitro cytotoxic, anti-inflammatory, α-glucosidase inhibitory, and antibacterial activities. As a result, these novel compounds demonstrated no obvious cytotoxic and antibacterial activity.

Koninginins X-Z, Three New Polyketides from Trichoderma koningiopsis SC-5.

Koninginins X-Z (1-3), three novel polyketides, were isolated from the solid fermentation of the endophytic fungus Trichoderma koningiopsis SC-5. Their structures, including the absolute configurations, were comprehensively characterized by a combination of NMR spectroscopic methods, HRESIMS, 13C NMR, DFT GIAO 13C NMR, and electronic circular dichroism calculations as well as single crystal X-ray diffraction. In addition, all the compounds were evaluated for antifungal activity against Candida albicans.

Anti-MRSA Dimeric and Brominated Phenyltetracenoids Produced by Streptomyces morookaense SC1169.

Eleven new phenyltetracenoid polyketides, streptovertimycins U (1) and V (2), 14-bromo-streptovertidione (3), streptovertimycins W-Y (4-6), and streptovertimycins Z1-Z5 (7-11), together with the known congeners fasamycins R (12) and S (13) and accramycins A (14) and B (15), were isolated from the NaBr-supplemented rice-grown cultures of Streptomyces morookaense SC1169. Their structures were elucidated by extensive spectroscopic analysis, single-crystal X-ray diffraction analysis, and theoretical computations of ECD spectra. Compounds 1 and 2 are methylene-bridged dimers of accramycin A, and compounds 3 and 7-11 are brominated fasamycin congeners. Compounds 5 and 8-14 exhibited activity against the drug-resistant bacteria MRSA and VRE (MIC = 0.6-5.0 µg/mL), and the dimer 1 displayed activity against MRSA (MIC = 2.5 µg/mL). Compounds 6-15 showed cytotoxicity against the human carcinoma A549, HeLa, HepG2, and MCF-7 cells in the IC50 range between 1.7 and 9.2 µM.

Isolation, identification, and antibacterial evaluation of endophytic fungi from Gannan navel orange.

Gannan navel orange is a famous brand in China but the isolation of its endophytic fungi was rarely reported. In this study, a total of 54 strains of endophytic fungi were successfully isolated from the pulp, peel, twig, and leaf of Gannan navel orange; they were successfully identified to belong to 17 species of 12 genera. All these strains were fermented using potato-dextrose agar (PDA) medium, and their secondary metabolites were then extracted with ethyl acetate (EtOAc). The antibacterial assays of Escherichia coli (E. coli), methicillin-resistant Staphylococcus aureus (MRSA), and Xanthomonas citri subsp. citri (Xcc) were also performed for the EtOAc extracts of these strains. As a result, the extracts of both Geotrichum sp. (gc-1-127-30) and Diaporthe biconispora (gc-1-128-79) demonstrated significant antibacterial activities against Xcc, and the MIC value for the extract of Colletotrichum gloeosporioides against MRSA was low to 62.5 µg/mL. Moreover, the chemical components of the extracts of Colletotrichum sp., Diaporthe biconispora, and Annulohypoxylon atroroseum were primarily investigated, and they successfully led to the isolation of 24 compounds involving a new botryane sesquiterpene. Among the isolated products, compound 2 showed significant inhibitory activities toward SA, MRSA, E. coli, and Xcc with MIC values of 12.5, 3.1, 125, and 12.5 µg/mL, respectively. This study revealed that the endophytic fungi of Gannan navel orange showed high potency to produce secondary metabolites with significant antibacterial effects.

Peniciriols A and B, two new citrinin derivatives from an endophytic fungus Penicillum citrinum TJNZ-27.

Two undescribed citrinin derivatives, named peniciriols A-B (1-2), together with six known compounds were isolated from endophytic fungus Penicillum citrinum TJNZ-27. The structures of two new compounds were well established by the detail interpretation of NMR and HRESIMS data as well as ECD measurement powered by molecular calculation. Among them, compound 1 shared an unprecedented dimerized citrinin skeleton with the formation of an intriguing 9H-xanthene ring system, whereas compound 2 possess a highly substituted phenylacetic acid skeleton, which was rarely-occurring in natural secondary metabolites. Moreover, these novel compounds were tested for cytotoxic and antibacterial activities, whereas these novel compounds did not exhibit any noticeable cytotoxic or antibacterial activities.

Two new secondary metabolites isolated from the fungus Penicillium virgatum T49-A.

The extensively chemical investigation of the EtOAc extract of the soil fungus Penicillium virgatum T49-A has successfully led to the isolation of two undescribed secondary metabolites penivirtone A (1) and peniviramide B (2) together with six known compounds. Their chemical structures including the absolute configurations of the two new compounds were comprehensively established by extensive analyses of NMR and HRESIMS spectra as well as ECD powered by theoretical calculations. Moreover, the cytotoxic and antibacterial activities of compounds 1-2 were also evaluated, whereas the two novel compounds showed no notable cytotoxic and antibacterial activities.

Copper-catalyzed umpolung Sonogashira-type coupling of arene boronic acids under visible light.

We report herein that a copper catalyst catalyzed efficient cross-coupling of aryl and alkenyl boronic acids with alkynyl-1,2-benziodoxol-3(1H)-ones to afford diaryl alkynes and enynes under mild visible light irradiation conditions using a catalytic amount of base or even in the absence of base. The reaction applies copper as the catalyst and tolerates a variety of functional moieties including aryl bromide and iodide.

Reduced type 3 innate lymphoid cells related to worsening kidney function in renal dysfunction.

Intestinal mucosa barrier injury and immunity imbalance contribute to chronic kidney disease (CKD) progression. Type 3 innate lymphoid cells (ILC3s) are essential for normal intestinal homeostasis. Nevertheless, the relationship between ILC3s and CKD remains largely unknown. The aim of this study was to investigate the relationship linking ILC3s to clinical indicators among patients with renal dysfunction. The levels of circulating ILC3s and dendritic cells, as well as their subsets, in patients with renal dysfunction and healthy controls were determined through flow cytometry. The levels of human plasma granulocyte-macrophage colony-stimulating factor (GM-CSF) were measured using enzyme-linked immunosorbent assay. Renal function was evaluated by measuring the estimated glomerular filtration rate (eGFR), as well as the levels of serum creatinine, blood urea nitrogen (BUN), and uric acid. The results revealed that the proportion of peripheral ILC3s was significantly decreased in patients with renal dysfunction. This reduction was positively associated with the levels of eGFR, and inversely associated with the levels of BUN and uric acid. Similarly, the percentage of circulating C-C motif chemokine receptor 6-positive (CCR6 +) ILC3s was also obviously reduced, and demonstrated positive and negative associations with the levels of eGFR and BUN, respectively. Furthermore, the levels of CCR6 + ILC3s correlated positively with those of GM-CSF, as well as type 1 conventional dendritic cells (cDC1s), which also decreased in parallel with kidney function. Thus, the reduction of ILC3s, particularly CCR6 + ILC3s, was related to worsening kidney function in patients with renal dysfunction. This effect may delay renal function impairment by regulating cDC1s via the secretion of GM-CSF, indicating that CCR6 + ILC3s may serve as efficient biomarkers for evaluating kidney function.