Isolation and Identification of 12-Deoxyphorbol Esters from Berg Latex: Targeted and Biased Non-Targeted Identification of 12-Deoxyphorbol Esters by UHPLC-HRMS.

Diterpenes from the genus are known for their ability to regulate the protein kinase C (PKC) family, which mediates their ability to promote the proliferation of neural precursor cells (NPCs) or neuroblast differentiation into neurons. In this work, we describe the isolation from Berg latex of fifteen 12-deoxyphorbol esters (-). A triester of 12-deoxy-16-hydroxyphorbol () and a 12-deoxyphorbol 13,20-diester () are described here for the first time.

-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.

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.

Phorbol Diesters and 12-Deoxy-16-hydroxyphorbol 13,16-Diesters Induce TGFα Release and Adult Mouse Neurogenesis.

A small library of phorbol 12,13-diesters bearing low lipophilicity ester chains was prepared as potential neurogenic agents in the adult brain. They were also used in a targeted UHPLC-HRMS screening of the latex of . Two new 12-deoxy-16-hydroxyphorbol 13,16-diesters were isolated, and their structures were deduced using two-dimensional NMR spectroscopy and NOE experiments.

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.

Topical Application of Glycolipids from Isochrysis galbana Prevents Epidermal Hyperplasia in Mice.

Chronic inflammatory skin diseases such as psoriasis have a significant impact on society. Currently, the major topical treatments have many side effects, making their continued use in patients difficult. Microalgae have emerged as a source of bio-active molecules such as glycolipids with potent anti-inflammatory properties.

Microalgae-derived oxylipins decrease inflammatory mediators by regulating the subcellular location of NFκB and PPAR-γ.

Oxylipins (OXLs) are bioactive molecules generated by the oxidation of fatty acids that promote the resolution of acute inflammation and prevent chronic inflammatory processes through molecular mechanisms that are not well known. We have previously reported the anti-inflammatory activity of microalgae-derived OXLs and OXL-containing biomass in two inflammatory bowel disease (IBD) models: 2,4,6-trinitrobenzenesulfonic acid (TNBS)-induced acute colitis and TNBS-induced recurrent colitis. In this study, we examined the in vitro anti-inflammatory mechanism of action of the most abundant OXLs isolated from Chlamydomonas debaryana (13S-HOTE and 13S-HODE) and Nannochloropsis gaditana (15S-HEPE).

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.

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.