The Effects of Marine Fungal Asterripeptides A-C on In Vitro and In Vivo Skin Infection.

This study aimed to investigate the in vitro and in vivo antibacterial and cytoprotective activities of marine fungal tripeptide derivatives with cinnamic acid moiety asterripeptides A-C (-). The antimicrobial and antibiofilm activities of asterripeptides A-C were tested using the ATCC 21027 strain. Human HaCaT keratinocytes infected with were used for the in vitro investigation of the various aspects of the influence of asterripeptides A-C by lumino- and fluorospectrometry, ELISA, flow cytometry, Western blotting, and microscopy techniques.

Mechanisms of Action of Sea Cucumber Triterpene Glycosides Cucumarioside A-1 and Djakonovioside A Against Human Triple-Negative Breast Cancer.

Breast cancer is the most prevalent form of cancer in women worldwide. Triple-negative breast cancer is the most unfavorable for patients, but it is also the most sensitive to chemotherapy. Triterpene glycosides from sea cucumbers possess a high therapeutic potential as anticancer agents.

Stonikacidin A, an Antimicrobial 4-Bromopyrrole Alkaloid Containing L-Idonic Acid Core from the Northwestern Pacific Marine Sponge .

Stonikacidin A (), the first representative of a new class of 4-bromopyrrole alkaloids containing an aldonic acid core, was isolated from the marine sponge . The compound is named in honor of Prof. Valentin A.

The influence of marine fungal meroterpenoid meroantarctine A toward HaCaT keratinocytes infected with Staphylococcus aureus.

A new biological activity was discovered for marine fungal meroterpenoid meroantarctine A with unique 6/5/6/6 polycyclic system. It was found that meroantarctine A can significantly reduce biofilm formation by Staphylococcus aureus with an IC of 9.2 µM via inhibition of sortase A activity.

New Zosteropenillines and Pallidopenillines from the Seagrass-Derived Fungus KMM 4679.

Ten new decalin polyketides, zosteropenilline M (), 11--8-hydroxyzosteropenilline M (), zosteropenilline N (), 8-hydroxyzosteropenilline G (), zosteropenilline O (), zosteropenilline P (), zosteropenilline Q (), 13-dehydroxypallidopenilline A (), zosteropenilline R () and zosteropenilline S (), together with known zosteropenillines G () and J (), pallidopenilline A () and 1-acetylpallidopenilline A (), were isolated from the ethyl acetate extract of the fungus KMM 4679 associated with the seagrass . The structures of isolated compounds were established based on spectroscopic methods. The absolute configurations of zosteropenilline Q () and zosteropenilline S () were determined using a combination of the modified Mosher's method and ROESY data.

The Composition of Triterpene Glycosides in the Sea Cucumber : Anticancer Activity of the Glycosides against Three Human Breast Cancer Cell Lines and Quantitative Structure-Activity Relationships (QSAR).

Eight sulfated triterpene glycosides, peronioside A () and psolusosides A (), B (), G (), I (), L (), N () and P (), were isolated from the sea cucumber . Peronioside A () is a new glycoside, while compounds - were found previously in , indicating the phylogenetic and systematic closeness of these species of sea cucumbers. The activity of - against human erythrocytes and their cytotoxicity against the breast cancer cell lines MCF-7, T-47D and triple-negative MDA-MB-231 were tested.

Metabolite profiles of Paragliomastix luzulae (formerly named as Acremonium striatisporum) KMM 4401 and its co-cultures with Penicillium hispanicum KMM 4689.

The marine holothurian-derived fungal strain KMM 4401 has been identified as Paragliomastix luzulae using 28S rDNA, ITS regions and the partial TEF1 gene sequences. The metabolite profile of the fungal culture was studied by UPLC-MS technique. The strain KMM 4401 is a source of various virescenoside-type isopimarane glycosides suggested as chemotaxonomic feature for this fungal species.

New piperazine derivatives helvamides B-C from the marine-derived fungus Penicillium velutinum ZK-14 uncovered by OSMAC (One Strain Many Compounds) strategy.

Four extracts of the marine-derived fungus Penicillium velutinum J.F.H.

Phanogracilins A-C, New Bibenzochromenones of Crinoid (Hartlaub, 1890).

Three new bibenzochromenones named phanogracilins A-C (-) were isolated from the crinoid . The structure of was established using X-ray crystallography as 5,5',6,6',8,8'-hexahydroxy-2,2'-dipropyl-4H,4'H-[7,9'-bibenzo[g]chromene]-4,4'-dione. This allowed us to assign reliably 2D NMR signals for compound and subsequently for its isomer that differed in the connecting position of two benzochromenone moieties (7,10' instead of 7,9'), and compound for that differed in the length of the aliphatic chain of one of the fragments.

Sulfated Triterpene Glycosides from the Far Eastern Sea Cucumber : Djakonoviosides C, D, E, and F; Cytotoxicity against Human Breast Cancer Cell Lines; Quantitative Structure-Activity Relationships.

Four new mono- and trisulfated triterpene penta- and tetraosides, djakonoviosides C (), D (), E (), and F () were isolated from the Far Eastern sea cucumber (Cucumariidae, Dendrochirotida), along with six known glycosides found earlier in other species. The structures of unreported compounds were established on the basis of extensive analysis of 1D and 2D NMR spectra as well as by HR-ESI-MS data. The set of compounds contains six different types of carbohydrate chains including two new ones.

Bioactive Polyketides from the Natural Complex of the Sea Urchin-Associated Fungi KMM 4718 and KMM 4747.

The marine-derived fungal strains KMM 4718 and KMM 4747 isolated from sea urchin as a natural fungal complex were identified as and based on Internal Transcribed Spacer (), partial β-tubulin (), and calmodulin () molecular markers as well as an ribosomal polymerase two, subunit two () region for KMM 4747. From the ethyl acetate extract of the co-culture, two new polyketides, sajaroketides A () and B (), together with (2'S)-7-hydroxy-2-(2'-hydroxypropyl)-5-methylchromone (), altechromone A (), norlichexanthone (), griseoxanthone C (), 1,3,5,6-tetrahydroxy-8-methylxanthone (), griseofulvin (), 6-O-desmethylgriseofulvin (), dechlorogriseofulvin (), and 5,6-dihydro-4-methyl-2H-pyran-2-one () were identified. The structures of the compounds were elucidated using spectroscopic analyses.

New Cyclopiane Diterpenes and Polyketide Derivatives from Marine Sediment-Derived Fungus KMM 4670 and Their Biological Activities.

Two new cyclopiane diterpenes and a new cladosporin precursor, together with four known related compounds, were isolated from the marine sediment-derived fungus KMM 4670, which was re-identified based on phylogenetic inference from ITS, , , and gene regions. The absolute stereostructures of the isolated cyclopianes were determined using modified Mosher's method and quantum chemical calculations of the ECD spectra. The isolation from the natural source of two biosynthetic precursors of cladosporin from a natural source has been reported for the first time.

The Metabolite Profiling of KMM4631 and Its Co-Cultures with Other Marine Fungi.

An KMM 4631 strain was previously isolated from a Pacific soft coral sp. sample and was found to be a source of a number of bioactive secondary metabolites. The aims of this work are the confirmation of this strain' identification based on ITS, , , and regions/gene sequences and the investigation of secondary metabolite profiles of KMM 4631 culture and its co-cultures with KMM 4689, sp.

Anthraquinone Derivatives and Other Aromatic Compounds from Marine Fungus KMM 4696 and Their Effects against .

New anthraquinone derivatives acruciquinones A-C (-), together with ten known metabolites, were isolated from the obligate marine fungus KMM 4696. Acruciquinone C is the first member of anthraquinone derivatives with a 6/6/5 backbone. The structures of isolated compounds were established based on NMR and MS data.

Djakonoviosides A, A, A, B-B - Triterpene Monosulfated Tetra- and Pentaosides from the Sea Cucumber : The First Finding of a Hemiketal Fragment in the Aglycones; Activity against Human Breast Cancer Cell Lines.

Seven new monosulfated triterpene glycosides, djakonoviosides A (), A (), A (), and B-B (-), along with three known glycosides found earlier in the other species, namely okhotoside A-1, cucumarioside A-1, and frondoside D, have been isolated from the far eastern sea cucumber (Cucumariidae, Dendrochirotida). The structures were established on the basis of extensive analysis of 1D and 2D NMR spectra and confirmed by HR-ESI-MS data. The compounds of groups A and B differ from each other in their carbohydrate chains, namely monosulfated tetrasaccharide chains are inherent to group A and pentasaccharide chains with one sulfate group, branched by C-2 Qui2, are characteristic of group B.

Phytoceramides from the Marine Sponge : Structural Analysis and Cytoprotective Effects.

In our research on sphingolipids from marine invertebrates, a mixture of phytoceramides was isolated from the sponge (Western Australia). Total ceramide, ceramide molecular species (obtained by RP-HPLC, high-performance liquid chromatography on reversed-phase column) and their sphingoid/fatty acid components were analyzed by NMR (nuclear magnetic resonance) spectroscopy and mass spectrometry. Sixteen new (, , , , , , , , , , -) and twelve known (, , , , , -, , , , ) compounds were shown to contain phytosphingosine-type backbones -t17:0 (), -t17:0 (), -t18:0 (), -t18:0 (), -t19:0 (), or -t19:0 (), -acylated with saturated (2)-2-hydroxy C (), C (), C (), C (), C (), C (), or C () acids.

Absolute Stereochemistry and Cytotoxic Effects of Vismione E from Marine Sponge-Derived Fungus sp. 1901NT-1.2.2.

The metabolic profile of the sp. 1901NT-1.2.

Chilensosides E, F, and G-New Tetrasulfated Triterpene Glycosides from the Sea Cucumber (Caudinidae, Molpadida): Structures, Activity, and Biogenesis.

Three new tetrasulfated triterpene glycosides, chilensosides E (), F (), and G (), have been isolated from the Far-Eastern sea cucumber (Caudinidae, Molpadida). The structures were established based on extensive analysis of 1D and 2D NMR spectra and confirmed by HR-ESI-MS data. The compounds differ in their carbohydrate chains, namely in the number of monosaccharide residues (five or six) and in the positions of sulfate groups.

Anti-Inflammatory Activity of 1,4-Naphthoquinones Blocking P2X7 Purinergic Receptors in RAW 264.7 Macrophage Cells.

P2X7 receptors are ligand-gated ion channels activated by ATP and play a significant role in cellular immunity. These receptors are considered as a potential therapeutic target for the treatment of multiple inflammatory diseases. In the present work, using spectrofluorimetry, spectrophotometry, Western blotting and ELISA approaches, the ability of 1,4-naphthoquinone thioglucoside derivatives, compounds and , to inhibit inflammation induced by ATP/LPS in RAW 264.

The Isolation, Structure Elucidation and Bioactivity Study of Chilensosides A, A, B, C, and D, Holostane Triterpene Di-, Tri- and Tetrasulfated Pentaosides from the Sea Cucumber (Caudinidae, Molpadida).

Five new triterpene (4,4,14-trimethylsterol) di-, tri- and tetrasulfated pentaosides, chilensosides A (), A (), B (), C (), and D () were isolated from the Far-Eastern sea cucumber . The structures were established on the basis of extensive analysis of 1D and 2D NMR spectra and confirmed by HR-ESI-MS data. The structural variability of the glycosides concerned the pentasaccharide chains.

Cytoprotective Polyketides from Sponge-Derived Fungus .

The new polyketides lopouzanones A and B, as well as the new 1--acetyl and 2--acetyl derivatives of dendrodochol B, were isolated from the sponge-derived marine fungus strain 168CLC-57.3. Moreover, six known polyketides, gliorosein, balticolid, dendrodolide G, dihydroisocoumarine, (-)-5-methylmellein, and dendrodochol B, were identified.

Structures and Biologic Activity of Chitonoidosides I, J, K, K and L-Triterpene Di-, Tri- and Tetrasulfated Hexaosides from the Sea Cucumber .

Five new triterpene di-, tri- and tetrasulfated hexaosides (chitonoidosides I (), J (), K (), K () and L ()) were isolated from the Far-Eastern sea cucumber , collected near Bering Island (Commander Islands) from a depth of 100-150 m. The structural variability of the glycosides concerned both the aglycones (with 7(8)- or 9(11)-double bonds) and carbohydrate chains differing from each other by the third sugar residue (Xyl or sulfated by C-6 Glc) and/or by the fourth-terminal in the bottom semi-chain-residue (Glc or sulfated by C-6 MeGlc) as well as by the positions of a sulfate group at C-4 or C-6 in the sixth-terminal in the upper semi-chain-residue (MeGlc). Hemolytic activities of these compounds - against human erythrocytes as well as cytotoxicity against human cancer cell lines, HeLa, DLD-1 and HL-60, were studied.

New Antibacterial Chloro-Containing Polyketides from the Alga-Derived Fungus KMM 4696.

Six new polyketides acrucipentyns A-F (-) were isolated from the alga-derived fungus KMM 4696. Their structures were established based on spectroscopic methods. The absolute configurations of acrucipentyn A was assigned by the modified Mosher's method and ROESY data analysis.

New Tripeptide Derivatives Asperripeptides A-C from Vietnamese Mangrove-Derived Fungus LM.5.2.

Three new tripeptide derivatives asterripeptides A-C (-) were isolated from Vietnamese mangrove-derived fungus LM.5.2.