Breviane Spiroditerpenoids with Anti-inflammatory and Antiviral Activities from Deep-Sea-Derived Fungus sp. F59.

Twelve new breviane spiroditerpenoids, namely, chrysobreviones A-L (-), together with seven structurally related analogues (-) were isolated from the EtOAc extract of the fermented cultures of deep-sea-derived fungus sp. F59. These structures including absolute configurations were resolved on the basis of extensive analysis of NMR spectroscopic data and HRESIMS, in association with experimental and calculated ECD data as well as the modified Mosher's method.

DMOA-derived polycyclic meroterpenoids with antiviral activities from the deep-sea-derived fungus Penicillium pancosmium A6A.

Two undescribed 3,5-dimethylorsellinic acid (DMOA) derived meroterpenoids, namely pancosterpenoids A (1) and B (2), were discovered from the EtOAc extract of the deep-sea sediment-derived fungus Penicillium pancosmium A6A. The gross structures were established by detailed analysis of the spectroscopic data (NMR and HRESIMS spectra), while their absolute configurations were resolved by comparing the experimental and calculated ECD data as well as X-ray single crystal diffraction analysis. Pancosterpenoid A (1) was the first representative of DMOA-derived meroterpenoids possessing a 6/6/6/5/5 pentacyclic system, while pancosterpenoid B (2) belongs to a class of rare 13-nor-citreohybridone meroterpenoids.

New Phthalides and Isochromanone Derivatives from the Deep-Sea-Derived Fungus Penicillium bialowiezense A3.

Two new phthalide derivatives, namely bialowalides A (1) and B (8), and one new isochromanone analogue biourgalide C (11), together with 8 known phthalides (2-7, 9, and 10) as well as two known isochromanones (12 and 13) were discovered from the EtOAc extract of the deep-sea-derived fungus Penicillium bialowiezense A3. The structures were resolved on the basis of extensive spectroscopic analyses (NMR and HRESIMS data), in association with the modified Mosher's method and ECD data for the determination of the absolute configurations. All isolated secondary metabolites (1-13) were tested their antiviral activities against the SARS-CoV-2 trVLP pseudovirus at a concentration of 25 μM.

Retrobisabolane A, a Novel Bisabolane-Derived Sesquiterpenoid Isolated from Deep-Sea-Derived Fungus Retroconis fusiformis MCCC 3A00792.

One novel bisabolane-derived sesquiterpenoid retrobisabolane A (1), featuring a methyl group location at the C-4 position instead of C-3 in the bisabolanes, and a known ester-substituted eremophilane-type sesquiterpenoid cryptosphaerolide (2), along with three known indole alkaloids (3-5) were discovered from the fermented cultures of a deep-sea-derived fungus Retroconis fusiformis MCCC 3A00792. The planar structure of new compound 1 was determined by extensive analysis of the NMR and HRESIMS spectra. The relative and absolute configurations of 1 were resolved by the coupling constant (J), calculation of ECD and NMR spectra, and the DP4+ probability analysis of the H and C NMR data.

Malfilanol C, a new sesquiterpenoid isolated from the deep-sea-derived A2 fungus.

The chemical examination of the rice solid fermentation products of the deep-sea-derived fungus A2 resulted in the isolation of one new sesquiterpenoid malfilanol C (), together with a rare analogue malfilanol B (). The planar structure of was resolved on the basis of the extensive analyses of the spectroscopic data (HRESIMS and NMR spectra), and its absolute configuration was assigned by quantum chemical calculation of the ECD data. Compound , featuring a bicyclo[5.

Phaeosphamides A and B, Cytotoxic Cyclodecadepsipeptides from the Mangrove-Derived Fungus sp. S296.

Chemical examination of the fermented broth of the mangrove-derived fungus sp. S296 resulted in the isolation of two new cyclodecadepsipeptides, namely phaeosphamides A () and B (), as well as one known congener Sch 217048 (). The structures of new metabolites, including absolute configurations, were established on the basis of extensive spectroscopic data analyses, chemical conversion, and Marfey's method.

Phenolic Metabolites from a Deep-Sea-Derived Fungus A2 and Their Nrf2-Dependent Anti-Inflammatory Effects.

Four undescribed phenolic compounds, namely asperpropanols A-D (-), along with two known congeners and , were isolated from A2, a deep-sea-derived fungus. The gross structures of the compounds were established by detailed analyses of the HRESIMS and NMR data, and their absolute configurations were resolved by modified Mosher's method and calculations of ECD data. Compounds - were found to have excellent anti-inflammatory effect on lipopolysaccharide (LPS)-induced RAW264.

Effect of piperine on the mitigation of obesity associated with gut microbiota alteration.

An obese mouse model induced by high-fat diet (HFD) feeding was used to reveal the role of piperine in modulating gut microbiota (GM). Piperine was administrated at 20 and 40 mg/kg body weight every day. As a result, piperine at 40 mg/kg significantly decreased body weight, liver weight, perirenal fat weight, and lowered serum triglycerides, total cholesterol, low-density lipoprotein cholesterol, and glucose levels in HFD-fed mice.

Antiviral Cyclopropane Acids from Deep-Sea-Derived Fungus .

Four novel monocyclic cyclopropane acids, namely, sydocyclopropanes A-D (-), along with one known congener hamavellone B (), were isolated from the MCCC 3A00324 fungus, which was isolated from the deep-sea sediment. The gross structures of novel compounds were established by detailed analyses of the spectroscopic data (HRESIMS and NMR spectra), and their absolute configurations were resolved on the basis of the quantum chemical calculations of ECD and NMR data, in association with DP4+ probability analyses. Sydocyclopropanes A-D, featuring the 1,1,2,3-tetrasubstituted cyclopropane nucleus with different lengthy alkyl side chains, were discovered in nature for the first time.

Bisabolane Sesquiterpenes with Anti-Inflammatory Activities from the Endophytic Fungus Penicillium citrinum DF47.

Seven new bisabolane-type sesquiterpenes (1-7), namely penicibisabolanes A-G, together with eight known analogs (8-15) were obtained from the AcOEt extract of the millet fermentation broth of the endophytic fungus Penicillium citrinum DF47, which was isolated from the fresh root of Codonopsis pilosula (Franch.) Nannf. The gross structures of new metabolites were determined on the basis of the spectroscopic data (HR-ESI-MS, 1D and 2D NMR spectra), while their absolute configurations were resolved by comparison of the experimental and calculated ECD spectra, in association with specific rotation data.

Acremolin D, a new acremolin alkaloid from the deep-sea sediment derived fungus.

Chemical investigation of the deep-sea-derived fungus MCCC 3A00324 led to the isolation of one new acremolin type alkaloid (acremolin D, ) and five known alkaloids (). The planar structure of was established by the extensive analyses of the NMR and HRESIMS data, while its absolute configuration was assigned by the comparison of the experimental and calculated ECD data. Acremolin D () represented the second analogue of acremolin found in nature.

- and -Palmitoleic Acid Isomers Regulate Cholesterol Metabolism in Different Ways.

Hypercholesterolemia is a preventable risk factor for atherosclerosis and cardiovascular disease. However, the mechanisms whereby -palmitoleic acid (POA) and -palmitoleic acid (POA) promote cholesterol homeostasis and ameliorate hypercholesterolemia remain elusive. To investigate the effects of POA and POA on cholesterol metabolism and its mechanisms, we induced hypercholesterolemia in mice using a high-fat diet and then intragastrically administered POA or POA once daily for 4 weeks.

New Monoterpenoids and Polyketides from the Deep-Sea Sediment-Derived Fungus MCCC 3A00324.

Chemical study of the secondary metabolites of a deep-sea-derived fungus MCCC 3A00324 led to the isolation of eleven compounds (-), including one novel () and one new () osmane-related monoterpenoids and two undescribed polyketides ( and ). The structures of the metabolites were determined by comprehensive analyses of the NMR and HRESIMS spectra, in association with quantum chemical calculations of the C NMR, ECD, and specific rotation data for the configurational assignment. Compound possessed a novel monoterpenoid skeleton, biogenetically probably derived from the osmane-type monoperpenoid after the cyclopentane ring cleavage and oxidation reactions.

Phenolic bisabolane and cuparene sesquiterpenoids with anti-inflammatory activities from the deep-sea-derived Aspergillus sydowii MCCC 3A00324 fungus.

Seventeen undescribed sesquiterpenoids including 14 phenolic bisabolanes, namely asperbisabolanes A-N (1-14), and 3 cuparenes (aspercuparenes A-C, 15-17), together with 10 known bisabolane analogues (18-27) were isolated from the EtOAc extract of fermented cultures of the deep sea sediment-derived fungus Aspergillus sydowii MCCC 3A00324. The new structures were established on the basis of extensive NMR and HRESIMS spectroscopic data analyses, while their absolute configurations were assigned by comparison of the experimental ECD spectra with those of the TDDFT-ECD calculated spectra or reported data in literature. Asperbisabolanes A (1) and B (2) are the first examples of bisabolane sesquiterpenoids featuring a 6/6/6 tricyclic nucleus.

Synthesis and Biological Evaluation of Analogues of Butyrolactone I as PTP1B Inhibitors.

In recent years, a large number of pharmacologically active compounds containing a butenolide functional group have been isolated from secondary metabolites of marine microorganisms. Butyrolactone I was found to be produced by isolated from several marine-derived samples. The hypoglycemic activity of butyrolactone I has aroused our great interest.

Separation of saturated fatty acids from docosahexaenoic acid-rich algal oil by enzymatic ethanolysis in tandem with molecular distillation.

Algal oil, rich in docosahexaenoic acid (DHA) and an environmentally sustainable source of ω-3 fatty acids, is receiving increasing attention. In the present study, a novel approach combining ethanolysis with a 1,3-specific immobilized lipase (Lipozyme TL IM) and molecular distillation was investigated to increase the DHA content of algal oil. Algal oil with a 45.

Antioxidant Capacity and Hepatoprotective Role of Chitosan-Stabilized Selenium Nanoparticles in Concanavalin A-Induced Liver Injury in Mice.

Selenium nanoparticles (SeNPs) have attracted wide attention for their use in nutritional supplements and nanomedicine applications. However, their potential to protect against autoimmune hepatitis has not been fully investigated, and the role of their antioxidant capacity in hepatoprotection is uncertain. In this study, chitosan-stabilized SeNPs (CS-SeNPs) were prepared by means of rapid ultra-filtration, and then their antioxidant ability and free-radical scavenging capacity were evaluated.

Selenium Nanoparticles-Embedded Chitosan Microspheres and Their Effects Upon Alcohol-Induced Gastric Mucosal Injury in Rats: Rapid Preparation, Oral Delivery, and Gastroprotective Potential of Selenium Nanoparticles.

Background: Selenium (Se) is an indispensable trace element required for animals and human beings, whereas Se-deficiency can accelerate the development of acute gastric injury induced by over-consumption of alcohol. Selenium nanoparticles (SeNPs), as a special Se-supplement with favorable properties and unique bioactivities, are expected to play a passive role in gastroprotection. To the best of our knowledge, the gastroprotective potential of SeNPs is unknown and also, a rapid preparation of orally stable SeNPs available for prospective commercial application in the clinic is needed.

Selenium-Nanoparticles-Loaded Chitosan/Chitooligosaccharide Microparticles and Their Antioxidant Potential: A Chemical and In Vivo Investigation.

Selenium nanoparticles (SeNPs) have attracted attention due to their favorable properties, unique bioactivities, and potential for use in nutritional supplements and nanomedicine applications. However, the application of SeNPs in the clinic has been greatly hindered by their poor stability, and their potential to protect against alcohol-induced oxidative stress has not been fully investigated. Herein, SeNPs were synthesized in the presence of chitosan (CS) or chitooligosaccharide (COS), and a mixture of SeNPs, CS, and COS was spray-dried to prepare selenium-nanoparticles-loaded chitosan/chitooligosaccharide microparticles (SeNPs-CS/COS-Ms).

Analgesia Effect of Enteric Sustained-Release Tetrodotoxin Pellets in the Rat.

Tetrodotoxin (TTX) was identified as a latent neurotoxin that has a significant analgesia effect. It was rapidly absorbed and excreted in rat after intramuscular (i.m.

Combination Formulation of Tetrodotoxin and Lidocaine as a Potential Therapy for Severe Arrhythmias.

Severe arrhythmias-such as ventricular arrhythmias-can be fatal, but treatment options are limited. The effects of a combined formulation of tetrodotoxin (TTX) and lidocaine (LID) on severe arrhythmias were studied. Patch clamp recording data showed that the combination of LID and TTX had a stronger inhibitory effect on voltage-gated sodium channel 1.

Docosahexaenoic acid inhibits hepatic stellate cell activation to attenuate liver fibrosis in a PPARγ-dependent manner.

Docosahexaenoic acid (DHA) has been found to have a hepatoprotective effect. In this study, we investigated the role of peroxisome proliferator-activated receptor γ (PPARγ) in DHA regulation of liver fibrosis. DHA was found to inhibit hepatic stellate cell (HSC)-LX2 cell viability and downregulate marker proteins of HSC activation.

Comparing the simultaneous determination of cis- and trans-palmitoleic acid in fish oil using HPLC and GC.

Background: Cis- and trans-palmitoleic acids (Cis-POA and trans-POA) are isomers of palmitoleic acid, a monounsaturated fatty acid which affects glucose and lipid metabolism, and reduces insulin resistance. Trans-POA is used as a biomarker for indicating the risk of type II diabetes and coronary heart disease, but no methods of analysis or distinguishing between cis-POA and trans-POA have yet been reported.

Method: An accurate and precise HPLC method was developed to determine cis- and trans-POA simultaneously, and compared with results from a GC method.

Determination of trehalose by ion chromatography and its application to a pharmacokinetic study in rats after intramuscular injection.

An ion chromatography method was established for detecting trehalose in rat plasma. The samples were analyzed using a CPMA1 column (250 × 4.0 mm, Thermo) with 120 mm NaOH as eluent at a flow rate of 0.

Processing Optimization and Characterization of Angiotensin-Ι-Converting Enzyme Inhibitory Peptides from Lizardfish () Scale Gelatin.

Hypertension can cause coronary heart disease. Synthetic angiotensin-converting enzyme (ACE) inhibitors are effective antihypertensive drugs but often cause side effects. The aim of this study was to prepare potential ACE inhibitors from scales.