Arylphthalide Delays Diabetic Retinopathy via Immunomodulating the Early Inflammatory Response in an Animal Model of Type 1 Diabetes Mellitus.

Diabetic retinopathy (DR) is one of the most prevalent secondary complications associated with diabetes. Specifically, Type 1 Diabetes Mellitus (T1D) has an immune component that may determine the evolution of DR by compromising the immune response of the retina, which is mediated by microglia. In the early stages of DR, the permeabilization of the blood-retinal barrier allows immune cells from the peripheral system to interact with the retinal immune system.

Rosmarinic Acid and Flavonoids of the Seagrass : New Aspects on Their Quantification and Their Correlation with Sunlight Exposure.

Seagrasses are plants adapted to the marine environment that inhabit shallow coastal waters, where they may be exposed to direct sunlight during low tides. These plants have photoprotection mechanisms, which could include the use of phenolic secondary metabolites. In this study, rosmarinic acid (RA) and the flavonoids of from the Bay of Cadiz (Spain) have been analyzed, first to define suitable conditions of leaves (i.

-Derived Spatane, Secospatane, Prenylcubebane and Prenylkelsoane Diterpenoids as Inhibitors of Nitric Oxide Production.

This study aimed to evaluate the anti-inflammatory potential of the different classes of diterpenoids produced by algae of the genus . First, sixteen diterpenoids (-), including spatane, secospatane, prenylcubebane, and prenylkelsoane metabolites, were isolated from the extract of the alga collected at the southwestern Spanish coasts. Eight of the isolated diterpenoids are new compounds whose structures were determined by spectroscopic means: the spatanes okaspatols A-D (-); the secospatane rugukamural D (); the prenylcubebanes okacubols A () and B (); and okamurol A (), which exhibits an unusual diterpenoid skeleton featuring a kelsoane-type tricyclic nucleus.

Synthesis and Antioxidant/Anti-Inflammatory Activity of 3-Arylphthalides.

Phthalides are a group of compounds with relevant biological activities in different areas such as cytotoxicity, anti-stroke activity, neuroprotection, and inflammation, among others. In this study we designed and synthesized a series of 3-arylphthalide derivatives in order to identify their antioxidant and anti-inflammatory activities. The synthetic methodology was established in terms of atom and step economy through a dehydrative coupling reaction between 3-hydroxyphthalide and different properly functionalized arene rings.

Diterpenoids from the Brown Alga and Their Anti-Inflammatory Activity.

Brown algae of the Family Dictyotaceae produce an array of structurally diverse terpenoids, whose biomedical potential in the anti-inflammatory area has been scarcely explored. Herein, the chemical study of the alga has led to the isolation of ten new diterpenoids: rugukadiol A (), rugukamurals A-C (-), and ruguloptones A-F (-). The structures of the new compounds were established by spectroscopic means.

Amentadione from the Alga as a Novel Osteoarthritis Protective Agent in an Ex Vivo Co-Culture OA Model.

Osteoarthritis (OA) remains a prevalent chronic disease without effective prevention and treatment. Amentadione (YP), a meroditerpenoid purified from the alga , has demonstrated anti-inflammatory activity. Here, we investigated the YP anti-osteoarthritic potential, by using a novel OA preclinical drug development pipeline designed to evaluate the anti-inflammatory and anti-mineralizing activities of potential OA-protective compounds.

Meroterpenoids from the Brown Alga as Potential Anti-Inflammatory and Lung Anticancer Agents.

The anti-inflammatory and anticancer properties of eight meroterpenoids isolated from the brown seaweed have been evaluated. The algal meroterpenoids (AMTs) were tested for their inhibitory effects on the production of the pro-inflammatory cytokines tumor necrosis factor (TNF-α), interleukin-6 (IL-6), and interleukin-1β (IL-1β), and the expression of cyclooxygenase-2 (COX-2), and inducible nitric oxide synthase (iNOS) in LPS-stimulated THP-1 human macrophages. The anticancer effects were assessed by cytotoxicity assays against human lung adenocarcinoma A549 cells and normal lung fibroblastic MRC-5 cells, together with flow cytometry analysis of the effects of these AMTs on different phases of the cell cycle.

Anticancer Activities of Meroterpenoids Isolated from the Brown Alga against the Human Colon Cancer Cells HT-29.

Colorectal cancer (CRC) is one of the most common types of cancers and a leading cause of cancer death worldwide. The current treatment for CRC mainly involves surgery, radiotherapy, and chemotherapy. However, due to the side effects and the emergence of drug resistance, the search for new anticancer agents, pharmacologically safe and effective, is needed.

5-Alkylresorcinol Derivatives from the Bryozoan Schizomavella mamillata: Isolation, Synthesis, and Antioxidant Activity.

The chemical study of the bryozoan has led to the isolation of six new 5-alkylresorcinol derivatives, schizols A-F (-), whose structures were established by spectrocospic means. Schizol A () exhibits a ()-6-phenylnon-5-enyl moiety linked to the C-5 of a resorcinol ring, while in schizol B () the substituent at C-5 contains an unusual 1,2-dihydrocyclobutabenzene moiety. Schizols C () and D () have been characterized as the 1-sulfate derivatives of and , respectively, and schizols E () and F () are the corresponding 1,3-disulfates.

Profiling of Phenolic Natural Products in the Seagrass Zostera noltei by UPLC-MS.

Seagrasses are marine plants that play important ecological functions in coastal ecosystems. The species Zostera noltei is widely distributed along the European coasts thriving in a variety of environmental conditions. In this study, the phenolic natural products of Z.

Cytotoxic Activity of Microalgal-derived Oxylipins against Human Cancer Cell lines and their Impact on ATP Levels.

Oxylipins are metabolites derived from lipid peroxidation. The plant oxylipin methyl jasmonate (MJ) shows cytotoxic activity against cancer cell lines of various origins, with ATP-depletion being one of the mechanisms responsible for this effect. The cytotoxic activity of oxylipins (OXLs) isolated from the microalgae Chlamydomonas debaryana (13-HOTE) and Nannochloropsis gaditana (15-HEPE) was higher against UACC-62 (melanoma) than towards HT-29 (colon adenocarcinoma) cells.

Molecular Characterization and Anti-inflammatory Activity of Galactosylglycerides and Galactosylceramides from the Microalga Isochrysis galbana.

Isochrysis galbana is a marine microalga rich in PUFAs that is widely used as feed in aquaculture and more recently investigated for its potential in food applications and as source of bioactive compounds. In this study, the biomass obtained from cultures of I. galbana has been investigated to determine its content in glycosylglycerides and glycosylceramides.

The Algal Meroterpene 11-Hydroxy-1'-O-Methylamentadione Ameloriates Dextran Sulfate Sodium-Induced Colitis in Mice.

Inflammatory bowel disease (IBD) is a complex class of immune disorders. Unfortunately, a treatment for total remission has not yet been found, while the use of natural product-based therapies has emerged as a promising intervention. The present study was aimed to investigate the anti-inflammatory effects of the algal meroterpene 11-hydroxy-1'-O-methylamentadione (AMT-E) in a murine model of dextran sodium sulphate (DSS)-induced colitis.

Cystoseira usneoides: A Brown Alga Rich in Antioxidant and Anti-inflammatory Meroditerpenoids.

Twelve new meroditerpenoids, 1-12, along with eight known compounds, have been isolated from the brown alga Cystoseira usneoides collected off the coast of Tarifa (Spain). The structures of the new metabolites have been established by spectroscopic techniques. All of the new compounds consist of a toluhydroquinone-derived nucleus linked to a regular diterpenoid moiety, which can either be acyclic or contain an ether ring.

Preventive effect of the microalga Chlamydomonas debaryana on the acute phase of experimental colitis in rats.

Inflammatory bowel diseases (IBD) are characterised by chronic uncontrolled inflammation of intestinal mucosa. Diet and nutritional factors have emerged as possible interventions for IBD. Microalgae are rich sources of n-3 PUFA and derived oxylipins.

Oxylipins from the microalgae Chlamydomonas debaryana and Nannochloropsis gaditana and their activity as TNF-α inhibitors.

The chemical study of the microalgae Chlamydomonas debaryana and Nannochloropsis gaditana has led to the isolation of oxylipins. The samples of C. debaryana have yielded the compounds (4Z,7Z,9E,11S,13Z)-11-hydroxyhexadeca-4,7,9,13-tetraenoic acid (1), (4Z,7E,9E,13Z)-11-hydroxyhexadeca-4,7,9,13-tetraenoic acid (2), (4Z,6E,10Z,13Z)-8-hydroxyhexadeca-4,6,10,13-tetraenoic acid (3), (4Z,8E,10Z,13Z)-7-hydroxyhexadeca-4,8,10,13-tetraenoic acid (4), and (5E,7Z,10Z,13Z)-4-hydroxyhexadeca-5,7,10,13-tetraenoic acid (5), which are derived from the fatty acid 16:4Δ(4,7,10,13) together with the compound (5Z,9Z,11E,15Z)-13-hydroxyoctadeca-5,9,11,15-tetraenoic acid (7) derived from coniferonic acid (18:4Δ(5,9,12,15)).

Antioxidant and anti-inflammatory meroterpenoids from the brown alga Cystoseira usneoides.

A chemical study of the alga Cystoseira usneoides has led to the isolation of six new meroterpenoids, cystodiones A-F (1-6), together with six known related compounds (7-12). The structures of the new metabolites have been established by spectroscopic techniques. In antioxidant assays all of the tested meroterpenes, and in particular cystodiones A (1) and B (2), 6-cis-amentadione-1'-methyl ether (7), and amentadione-1'-methyl ether (8), exhibited strong radical-scavenging activity.

A total synthesis prompts the structure revision of haouamine B.

A concise asymmetric approach to the indeno-tetrahydropyridine core of the unusual alkaloid haouamine B allowed for an investigation of a biomimetic oxidative phenol coupling as a proposed biosynthetic step, and ultimately provided access to the published structure of the natural product. As a consequence of our synthetic studies, the structure of haouamine B has been revised.

Culture of explants from the sponge Mycale cecilia to obtain bioactive mycalazal-type metabolites.

Natural products with promising biomedical properties have been described from sponges, but the problem of supply is usually a limiting factor for their pharmacological evaluation. Mycale cecilia produces an array of metabolites containing a pyrrole-2-carbaldehyde moiety (e.g.

Sesquiterpenes from the sponge Axinyssa isabela.

Further research on the constituents of the sponge Axinyssa isabela collected in the Gulf of California has led to the isolation of nine new sesquiterpenes, the eudesmanes axinisothiocyanates M and N (1, 2), the bisabolane axinythiocyanate A (3), and the aristolane derivatives axinysones A-E (4-8) and axinynitrile A (9), together with four known sesquiterpenoids (10-13). The structures of the new metabolites have been established by spectroscopic techniques.The absolute configuration of axinysones A (4) and B (5) has been assigned after esterification with (R)- and (S)-MPA acids.

Cembrane diterpenes from the gorgonian Leptogorgia laxa.

The new cembrane diterpenes leptodienone A (2) and leptodienone B (3) and the known compounds lopholide, lophodiol B, lophodione, and lophotoxin (1) have been isolated from the gorgonian Leptogorgia laxa collected in the Gulf of California. The structures of the new metabolites have been established by spectroscopic techniques. The in vitro cytotoxicity of the new compounds has been tested against three human tumor cell lines.

Isothiocyanate sesquiterpenes from a sponge of the genus axinyssa.

The chemical study of a sponge of the genus Axinyssa collected in the Gulf of California has led to the isolation of the new bicyclic sesquiterpenes axinisothiocyanates A-L ( 1- 12) together with the known compounds (1 R,6 S,7 S,10 S)-10-isothiocyanato-4-amorphene ( 13), (4 R*,5 R*,7 S*,10 R*)-4-isocyanoeudesm-11-ene, (-)-epipolasin A, and (+)-aristolone. The structures of the new metabolites have been established by spectroscopic techniques, including the analysis of pyridine-induced 1H NMR chemical shifts. The cytotoxic activity has been tested against three human tumor cell lines.

Cytotoxic dibromotyrosine-derived metabolites from the sponge Aplysina gerardogreeni.

The chemical study of the sponge Aplysina gerardogreeni collected at the Gulf of California has led to the isolation of four new dibromotyrosine-derived metabolites, aplysinones A-D, whose structures were determined by spectroscopic analysis and chemical methods. The new compounds and four semisynthetic analogues prepared in this study have shown cytotoxic activity against human tumor cell lines.

Cembrane diterpenes from the gorgonian Lophogorgia peruana.

The chemical study of the gorgonian Lophogorgia peruana collected at the Gulf of California has led to the isolation of the new diterpenes lophodienone (2), lophodiol A (3), lophodiol B (4), 17-acetoxylophotoxin (5), 15,16-epoxylophotoxin (6), 17-acetoxy-15,16-epoxylophotoxin (7), and isoepoxylophodione (8), together with the known compounds lophotoxin (1), rubifolide (9), lopholide (10), deoxylophotoxin (11), and the lophotoxin analogues 12 and 13. The structures of the new metabolites have been established by spectroscopic techniques and chemical correlation. The in vitro cytotoxicity has been tested against three tumor cell lines.

Steroids from the Antarctic octocoral Anthomastus bathyproctus.

Seven new steroids, compounds 1-7, were isolated from the Antarctic octocoral Anthomastus bathyproctus. The structures of the new metabolites have been established by analysis of their spectroscopic data. The in vitro cytotoxicity has been tested against three human tumor cell lines.