Isolation, structural elucidation and biosynthetic pathway of bioactive prenyl quinone compounds from Panus lecomtei based on untargeted metabolomics combined with molecular networking.

Panus lecomtei is a relatively unfamiliar and undeveloped mushroom. This study generated ethyl acetate extracts of P. lecomtei intracellular (I), extracellular (E) and total fermentation broth (T).

Antidiabetic action of the Chinese formula Shouhuitongbian and the underlying mechanism associated with alteration of gut microbiota.

Background: The prevalence and incidence of type 2 diabetes mellitus (T2DM) have dramatically increased. The intestinal flora and its derived metabolites are demonstrated to play vital roles in the etiology and onset of T2DM. Shouhuitongbian (SHTB) is a traditional Chinese formula to treat constipation.

Gut commensal Christensenella minuta modulates host metabolism via acylated secondary bile acids.

A strong correlation between gut microbes and host health has been observed in numerous gut metagenomic cohort studies. However, the underlying mechanisms governing host-microbe interactions in the gut remain largely unknown. Here we report that the gut commensal Christensenella minuta modulates host metabolism by generating a previously undescribed class of secondary bile acids with 3-O-acylation substitution that inhibit the intestinal farnesoid X receptor.

Discovery of antifungal secondary metabolites from an intestinal fungus Fusarium sp.

Intestinal fungi, which are important parts of the gut microbiota, have the ability to produce specialized metabolites that significantly contribute to maintaining the balance of the gut microbiota and promoting the health of the host organism. In the present study, two new glycosides, including fusintespyrone A (1) and cerevisterolside A (4), as well as ten known compounds were isolated from the intestinal fungus Fusarium sp. LE06.

Identification of siderophores blocking infection of Pseudomonas aeruginosa from Kitasatospora sp. LS1784.

Siderophores are low-molecular-mass, high-affinity chelators of Fe ions that are critical for the survival of bacteria in ferric deficient environment. Exogenous siderophores are potential bacteriostat by disrupting the iron-uptake process of pathogens. In our previous work to discover siderophores, strain LS1784 was previously predicted to produce new catecholate-type siderophores by genome analysis but no compounds were obtained.

Identification and Characterization of Peptaibols as the Causing Agents of Infecting the Edible Mushroom .

(previously known as ) is a pathogenic fungus of mushrooms. The molecular mechanism underlying the infection of in fruiting bodies remains unknown. In this study, three known peptaibols, alamethicin F-50, polysporin B, and septocylindrin B (-), and a new analogue, longisporin A (), were detected and identified in the culture of and the fruiting bodies of infected by .

Japonamides A and B, Two New Cyclohexadepsipeptides from the Marine-Sponge-Derived Fungus Aspergillus japonicus and Their Synergistic Antifungal Activities.

Two new cyclohexadepsipeptides japonamides A (1) and B (2) were isolated from the ethyl acetate extract of a marine-sponge-derived fungus based on molecular networking. Their structures were elucidated by comprehensive spectral analysis and their absolute configurations were confirmed by Marfey's method. Compounds 1 and 2 showed no antifungal activities against SC5314 measured by the broth microdilution method but exhibited prominent synergistic antifungal activities in combination with fluconazole, ketoconazole, or rapamycin.

Molecular networking assisted discovery and combinatorial biosynthesis of new antimicrobial pleuromutilins.

Pleuromutilins, the unique fungal metabolites possessing 5/6/8 tricyclic skeleton, are potent antibacterial leading compounds for the development of new antibiotics. We applied the MS/MS molecular networking technique and the combinatorial biosynthesis approach to discover new pleuromutilin analogues. Ten pleuromutilin derivatives including seven new compounds (1-7) were obtained from the solid culture of Omphalina mutila.

Glyceroglycolipids from the solid culture of strain LY34 isolated from Tibet of China.

is a well-known entomogenous fungus with its fruiting bodies or cultural mycelium as food and herbal medicines in Asia. While metabolites which could responsible for its potent pharmaceutical effects has long remained to be elucidated. In this work, chemical investigation on the solid culture of strain LY34 led to the discovery of six digalactosyldiacylglycerols (DGDGS, ) including one new.

Discovery of Anti-MRSA Secondary Metabolites from a Marine-Derived Fungus .

Methicillin-resistant (MRSA), a WHO high-priority pathogen that can cause great harm to living beings, is a primary cause of death from antibiotic-resistant infections. In the present study, six new compounds, including fumindoline A-C (-), 12, 13-hydroxy-asperfumigatin (), 2--tryptoquivaline F () and penibenzophenone E (), and thirty-nine known ones were isolated from the marine-derived fungus H22. The structures and the absolute configurations of the new compounds were unambiguously assigned by spectroscopic data, mass spectrometry (MS), electronic circular dichroism (ECD) spectroscopic analyses, quantum NMR and ECD calculations, and chemical derivatizations.

Exploring Verrucosidin Derivatives with Glucose-Uptake-Stimulatory Activity from Using MS/MS-Based Molecular Networking.

Under the guidance of LC-MS/MS-based molecular networking, seven new verrucosidin derivatives, penicicellarusins A-G (-), were isolated together with three known analogues from the fungus . The structures of the new compounds were determined by a combination of NMR, mass and electronic circular dichroism spectral data analysis. The absolute configuration of penicyrone A () was corrected based on X-ray diffraction analyses.

Cyclic Tetrapeptides with Synergistic Antifungal Activity from the Fungus Using LC-MS/MS-Based Molecular Networking.

Fungal natural products play a prominent role in the development of pharmaceuticalagents. Two new cyclic tetrapeptides (CTPs), westertide A () and B (), with eight known compounds (-) were isolated from the fungus guided by OSMAC (one strain-many compounds) and molecular networking strategies. The structures of new compounds were unambiguously determined by a combination of NMR and mass data analysis, and chemical methods.

Sesquiterpenes and polyphenols with glucose-uptake stimulatory and antioxidant activities from the medicinal mushroom Sanghuangporus sanghuang.

A chemical investigation on the fermentation products of Sanghuangporus sanghuang led to the isolation and identification of fourteen secondary metabolites (1-14) including eight sesquiterpenoids (1-8) and six polyphenols (9-14). Compounds 1-3 were sesquiterpenes with new structures which were elucidated based on NMR spectroscopy, high resolution mass spectrometry (HRMS) and electronic circular dichroism (ECD) data. All the isolates were tested for their stimulation effects on glucose uptake in insulin-resistant HepG2 cells, and cellular antioxidant activity.

Lanostane Triterpenoids with PTP1B Inhibitory and Glucose-Uptake Stimulatory Activities from Mushroom Collected in North America.

A chemical investigation on the fruiting bodies of led to the isolation and identification of 28 lanostane triterpenoids including 11 new compounds () and 17 known analogues (). Their structures were elucidated by extensive one-dimensional NMR, two-dimensional NMR, and MS spectra. All isolates were tested for their anti-inflammatory activity, protein tyrosine phosphatase 1B (PTP1B) inhibitory activity , and effect on glucose uptake in insulin-resistant HepG2 cells.

Siderophore and indolic acid production by BJ-18 and their plant growth-promoting and antimicrobe abilities.

BJ-18, a N-fixing bacterium, is able to promote plant growth, but the secondary metabolites that may play a role in promoting plant growth have never been characterized. In this study, untargeted metabolomics profiling of . BJ-18 indicated the existence of 101 known compounds, including N-acetyl ornithine, which is the precursor of siderophores, plant growth regulators such as trehalose 6-phosphate, betaine and trigonelline, and other bioactive molecules such as oxymatrine, diosmetin, luotonin A, (-)-caryophyllene oxide and tetrahydrocurcumin.

New meroterpenoid compounds from the culture of mushroom Panus lecomtei.

Two new meroterpenoid compounds (1 and 2) together with five known meroterpenoid derivatives (3-7) were isolated from solid culture of mushroom Panus lecomtei. The structures of new compounds were confirmed by the analysis of NMR and HR-ESI-MS spectroscopic data. The biosynthetic pathway of 1-7 was postulated.

Identification and α-Glucosidase Inhibitory Activity of Meroterpenoids from Hericium erinaceus.

is a very popular edible and medicinal mushroom used for the treatment of enervation and gastrointestinal diseases in Eastern Asia. Chemical investigation on the fruiting body of led to the isolation of 4 new (1:  - 4: ) and 10 known meroterpenoids (5:  - 14: ). The structures of new compounds were determined via analysis of NMR and MS data in combination with chemical derivatization.

A concise total synthesis and PPAR activation activity of hericerin from Hericium erinaceum.

Hericerin is an isoindolinone meroterpenoid alkaloid isolated from medicinal mushroom Hericium erinaceum with some bioactivities. Herein, a concise total synthesis of hericerin was described, with four steps and 30% overall yield starting from commercially available methyl 3-hydroxy-5-methoxybenzoate and geranyl bromide. A comprehensive effect of hericerin on HepG2 cell line was observed and confirmed by transcriptomic analysis.

Terphenyl derivatives and terpenoids from a wheat-born mold Aspergillus candidus.

A new p-terphenyl derivative aspergicandidusin A (1), a new cleistanthane diterpenoid 6-deoxyaspergiloid C (13), and 12 known compounds (2-12, and 14) were isolated from the mold Aspergillus candidus. The structures of the new compounds were elucidated by spectral analysis of NMR and MS data. The absolute configuration of C-1 in 13 was determined via the circular dichroism data of the [Rh(OCOCF)] complex.

Cytotoxic Secondary Metabolites from the Endolichenic Fungus Hypoxylon fuscum.

As part of our search for new cytotoxic and antimicrobial natural products from endolichenic fungi, 19 compounds including 1 new 10-member lactone (2: ), 1 new polyacetylene glycoside (3: ), 1 new brasilane-type sesquiterpenoid glycoside (4: ), and 2 isobenzofuran-1(3H)-one derivatives (5: and 6: ) were isolated from the solid culture of the endolichenic fungus Their structures were unambiguously elucidated by NMR spectroscopic data, MS, ECD (electronic circular dichroism) calculation, and chemical methods. The cytotoxic effects on K562, SW480, and HEPG2 cell lines and the antimicrobial activity against , and were assessed. Compounds 1, 2: , and 5: exhibited moderate cytotoxicity against K562, SW480, and HEPG2 cell lines while compounds 1, 9: , and 11: displayed weak antibacterial activity against

Lanostane Triterpenoids with Glucose-Uptake-Stimulatory Activity from Peels of the Cultivated Edible Mushroom Wolfiporia cocos.

A chemical study on the peels of the cultivated edible mushroom Wolfiporia cocos led to the isolation and identification of 47 lanostane triterpenoids including 16 new compounds (1-16). The structures of the new compounds were determined by analysis of the NMR, MS, and electronic circular dichroism (ECD) data. Compounds 1 and 2 represent new members of the family of 4,5-secolanostane triterpenes.

Four New Cytotoxic Arborinane-Type Triterpenes from the Endolichenic Fungus Myrothecium inundatum.

Two new arborinane-type triterpenes, myrotheols A (1: ) and B (2: ), two new arborinane-type glycosides, myrothesides C (3: ) and D (4: ), together with four known diterpenes (5:  - 8: ) were isolated from the ethyl acetate extract of the endolichenic fungus . The structures of new compounds 1:  - 4: were elucidated by NMR and MS analyses. The absolute configuration of 1: was assigned by a single-crystal X-ray diffraction experiment.

Botryane Sesquiterpenoids, Cyclopentadepsipeptides, Xanthones, and Trichothecenes from Trichoderma oligosporum.

Five new botryane sesquiterpenes (1: -5: ), one new cyclopentadepsipeptide (9: ), and two new xanthones (11:  - 12: ), together with 11 known compounds, were isolated from . The structures of the new compounds were identified by comprehensive spectroscopic methods including nuclear magnetic resonance and mass spectrometry. The cytotoxicity of 1: -19: was evaluated against K562, A549, and ASPC cell lines.

Triterpenes and meroterpenes from Ganoderma lucidum with inhibitory activity against HMGs reductase, aldose reductase and α-glucosidase.

Seven new compounds including four lanostane triterpenoids, lucidenic acids Q-S (1-3) and methyl ganoderate P (4), and three triterpene-farnesyl hydroquinone conjugates, ganolucinins A-C (5-7), one new natural product ganomycin J (8), and 73 known compounds (9-81) were isolated from fruiting bodies of Ganoderma lucidum. The structures of the compounds 1-8 were determined by spectroscopic methods. Bioactivities of compounds isolated were assayed against HMG-CoA reductase, aldose reductase, α-glucosidase, and PTP1B.

A novel class of α-glucosidase and HMG-CoA reductase inhibitors from Ganoderma leucocontextum and the anti-diabetic properties of ganomycin I in KK-A mice.

Three new meroterpenoids, ganoleucin A-C (1-3), together with five known meroterpenoids (4-8), were isolated from the fruiting bodies of Ganoderma leucocontextum. The structures of the new compounds were elucidated by extensive spectroscopic analysis, circular dichroism (CD) spectroscopy, and chemical transformation. The inhibitory effects of 1-8 on HMG-CoA reductase and α-glucosidase were tested in vitro.