Interaction of Liposomes Containing the Carrageenan/Echinochrome Complex with Human HaCaT Keratinocytes In Vitro.

Liposomal drug delivery systems are successfully used in various fields of medicine for external and systemic applications. Marine organisms contain biologically active substances that have a unique structure and exhibit a wide range of biological activities. Polysaccharide of red seaweed (carrageenan (CRG)), and water-insoluble sea urchin pigment (echinochrome (Ech)) interact with each other and form a stable complex.

Composition of Triterpene Glycosides of the Far Eastern Sea Cucumber Levin et Stepanov; Structure Elucidation of Five Minor Conicospermiumosides A-1, A-2, A-3, A-1, and A-2; Cytotoxicity of the Glycosides Against Human Breast Cancer Cell Lines; Structure-Activity Relationships.

Five new non-holostane di- and trisulfated triterpene pentaosides, conicospermiumosides A-1 (), A-2 (), A-3 (), A-1 (), and A-2 () were isolated from the Far Eastern sea cucumber Levin et Stepanov (Cucumariidae, Dendrochirotida). Twelve known glycosides found earlier in other species were also obtained and identified. The structures of new compounds were established on the basis of extensive analysis of the 1D and 2D NMR spectra, as well as by the HR-ESI-MS data.

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.

Exosome-like Nanoparticles, High in Trans-δ-Viniferin Derivatives, Produced from Grape Cell Cultures: Preparation, Characterization, and Anticancer Properties.

: Recent interest in plant-derived exosome-like nanoparticles (ENs) has surged due to their therapeutic potential, which includes antioxidant, anti-inflammatory, and anticancer activities. These properties are attributed to their cargo of bioactive metabolites and other endogenous molecules. However, the properties of ENs isolated from plant cell cultures remain less explored.

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.

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.

Polyphenols from Heartwood Protect Neuronal Cells from Oxidative Stress and Prevent Herpetic Infection.

Here, we continued the investigation of anti-HSV-1 activity and neuroprotective potential of 14 polyphenolic compounds isolated from heartwood. We determined the absolute configurations of asymmetric centers in scirpusin A () and maackiazin () as 7,8 and 1″,2″, respectively. We showed that dimeric stilbens maackin () and scirpusin A () possessed the highest anti-HSV-1 activity among polyphenols -.

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.

Protection Activity of 1,4-Naphthoquinones in Rotenone-Induced Models of Neurotoxicity.

The MTS cell viability test was used to screen a mini library of natural and synthetic 1,4-naphthoquinone derivatives (1,4-NQs) from marine sources. This screening identified two highly effective compounds, and , which showed potential in protecting Neuro-2a neuroblastoma cells from the toxic effects of rotenone in an in vitro model of neurotoxicity. The selected 1,4-NQs demonstrated the capability to reduce oxidative stress by decreasing the levels of reactive oxygen species (ROS) and nitric oxide (NO) in Neuro-2a neuroblastoma cells and RAW 264.

Anticancer Activity of the Marine Triterpene Glycoside Cucumarioside A-2 in Human Prostate Cancer Cells.

Despite recent advances in the treatment of metastatic castration-resistant prostate cancer (CRPC), treatment is inevitably hampered by the development of drug resistance. Thus, new drugs are urgently needed. We investigated the efficacy, toxicity, and mechanism of action of the marine triterpene glycoside cucumarioside A-2 (CA-2) using an in vitro CRPC model.

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.

Holothurian triterpene glycoside cucumarioside A-2 induces macrophages activation and polarization in cancer immunotherapy.

Background: Despite intensive developments of adoptive T cell and NK cell therapies, the efficacy against solid tumors remains elusive. Our study demonstrates that macrophage-based cell therapy could be a potent therapeutic option against solid tumors.

Methods: To this end, we determine the effect of a natural triterpene glycoside, cucumarioside A-2 (CA-2), on the polarization of mouse macrophages into the M1 phenotype, and explore the antitumor activity of the polarized macrophage.

Tetracyclic 1,4-Naphthoquinone Thioglucoside Conjugate U-556 Blocks the Purinergic P2X7 Receptor in Macrophages and Exhibits Anti-Inflammatory Activity In Vivo.

P2X7 receptors (P2X7Rs) are ligand-gated ion channels that play a significant role in inflammation and are considered a potential therapeutic target for some inflammatory diseases. We have previously shown that a number of synthetic 1,4-naphthoquinones are capable of blocking P2X7Rs in neuronal and macrophage cells. In the present investigation, we have demonstrated the ability of the tetracyclic quinone-thioglucoside conjugate , derived from 1,4-naphthoquinone thioglucoside, to inhibit ATP-induced Ca influx and YO-PRO-1 dye uptake, which indicates blocking P2X7R in RAW 264.

Assimiloside A, a Glycolipid with Immunomodulatory Activity from the Northwestern Pacific Marine Sponge .

Assimiloside A (), an unprecedented marine glycolipid containing a γ-lactone of 4,16,26-trihydroxy C fatty acid as an aglycon and a trisaccharide carbohydrate moiety, was isolated from the marine sponge . Its structure was elucidated by NMR spectroscopy, mass spectrometry, chemical transformations, and ECD spectroscopy combined with time-dependent density functional theory calculations. Assimiloside A at nontoxic concentrations of 0.

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.

New Anti-Hypoxic Metabolites from Co-Culture of Marine-Derived Fungi KMM 4638 and sp. KMM 4639.

The KMM 4639 strain was identified as sp. based on two molecular genetic markers: ITS and β-tubulin regions. Chemical investigation of co-culture marine-derived fungi sp.

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.

Pectins from the sea grass Enhalus acoroides (L.f.) Royle: Structure, biological activity and ability to form nanoparticles.

Two pectins from the seagrass Enhalus acoroides (L.f.) Royle were isolated for the first time.

Carrageenans and Their Oligosaccharides from Red Seaweeds and (Phyllophoraceae) and Their Antiproliferative Activity.

Comparative structural analysis of gelling polysaccharides from and belonging to Phyllophoraceae and the effect of their structural features and molecular weight on human colon cancer cell lines (HT-29, DLD-1, HCT-116) was carried out. According to chemical analysis, IR and NMR spectroscopies, produces kappa/iota-carrageenan with a predominance of kappa units and minor amounts of mu and/or nu units, while the polysaccharide from is iota/kappa-carrageenan (predominance of iota units) and contains negligible amounts of beta- and nu-carrageenans. Iota/kappa- (Afg-OS) and kappa/iota-oligosaccharides (Mp-OS) were obtained from the original polysaccharides through mild acid hydrolysis.

Neuroprotective and Antiherpetic Properties of Polyphenolic Compounds from Heartwood.

In this study, we isolated a new isoflavanostilbene maackiapicevestitol () as a mixture of two stable conformers and as well as five previously known dimeric and monomeric stilbens: piceatannol (), maackin (), scirpusin A (), maackiasine (), and maackolin () from heartwood, using column chromatography on polyamide, silicagel, and C-18. The structures of these compounds were elucidated by NMR, HR-MS, and CD techniques. Maksar obtained from heartwood and polyphenolics - possessed moderate anti-HSV-1 activity in cytopathic effect (CPE) inhibition and RT-PCR assays.

Recombinant Analogs of Sea Anemone Kunitz-Type Peptides Influence P2X7 Receptor Activity in Neuro-2a Cells.

Purinergic P2X7 receptors (P2X7) have now been proven to play an important role and represent an important therapeutic target in many pathological conditions including neurodegeneration. Here, we investigated the impact of peptides on purinergic signaling in Neuro-2a cells through the P2X7 subtype in in vitro models. We have found that a number of recombinant peptides, analogs of sea anemone Kunitz-type peptides, are able to influence the action of high concentrations of ATP and thereby reduce the toxic effects of ATP.

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.