Cyanotoxins obtained from a freshwater cyanobacterial collection at Green Lake, Seattle during harmful algal bloom in the summer of 2014 were studied using new approach based on molecular networking analysis liquid chromatography tandem mass spectrometry (LC-MS/MS) data. This MS is particularly well-suited for detection cyanotoxin variants and resulted discovery three cyclic peptides, namely microcystin-MhtyR (6), which comprised about half total microcystin content bloom, ferintoic acids C...

Owing to the extensive development of drug resistance in pathogens against available antibiotic arsenal, antimicrobial is now an emerging major threat public healthcare. Anti-virulence drugs are a new type therapeutic agent aiming at virulence factors rather than killing pathogen, thus providing less selective pressure for evolution resistance. One promising example this concept targets bacterial quorum sensing (QS), because QS controls many responsible infections. Marine sponges and their...

An in-depth study of the secondary metabolites contained in Caribbean sponge Smenospongia aurea led to isolation smenamide A (1) and B (2), hybrid peptide/polyketide compounds containing a dolapyrrolidinone unit. Their structures were elucidated using high-resolution ESI-MS/MS homo- heteronuclear 2D NMR experiments. Structures smenamides suggested that they are products cyanobacterial metabolism, 16S rRNA metagenomic analysis detected Synechococcus spongiarum as only cyanobacterium present...

The study of the secondary metabolites contained in organic extract Caribbean sponge Smenospongia aurea led to isolation smenothiazole A (3) and B (4), hybrid peptide/polyketide compounds. Assays performed using four solid tumor cell lines showed that smenothiazoles exert a potent cytotoxic activity at nanomolar levels, with selectivity over ovarian cancer cells pro-apoptotic mechanism.

Plakoside A (1a) and B (2a), two unique glycosphingolipids belonging to a new class of prenylated glycolipid, have been isolated from the marine sponge Plakortis simplex, their structures determined by spectroscopic chemical means. Plakosides are strongly immunosuppressive on activated T cells proved be useful natural models for an improved comprehension structural requirements immunomodulating activity glycosphingolipids.

Cyanobacterial blooms (CBs) are generally triggered by eutrophic conditions due to anthropogenic nutrient inputs local waters (wastewater or contaminated waters). During the bloom, some species produce toxic secondary metabolites (cyanotoxins) that dangerous for humans and animals. Here, a multidisciplinary strategy an early detection constant monitoring is proposed. This combines remote/proximal sensing technology with analytical/biotechnological analyses. To demonstrate applicability of...

Ring strain causes planar chirality in tedarenes A and B, two cyclic diarylheptanoids isolated from the marine sponge Tedania ignis. In both molecules, chiral plane is an olefinic system, which very rare among natural products. tedarene (1), interconversion too fast to allow isolation of enantiomeric atropisomers but still slow enough cause coalescence some (1)H (13)C NMR signals at room temperature. B (2), also shows stable central axial chirality, diastereomers are equilibrium. Tedarene...

Sponge-associated microorganisms are able to assemble the complex machinery for production of secondary metabolites such as polyketides, most important class marine natural products from a drug discovery perspective. A comprehensive overview polyketide biosynthetic genes sponge Plakortis halichondrioides and its symbionts was obtained in present study by massively parallel 454 pyrosequencing heterogeneous PCR (Polymerase Chain Reaction) amplified metagenomic DNA specimen P. collected...

Studies of non‐ribosomal peptide/polyketide (NRP/PK) hybrid compounds in the holobiome Caribbean marine sponge Smenospongia conulosa led to isolation two new chlorinated thiazole‐containing metabolites, conulothiazoles A ( 5 ) and B 6 ), along with four NRP/PK hybrids previously isolated from a different species. Structural elucidation was accomplished on few micrograms pure using extensive NMR MS studies, whereas determination absolute configuration amino acid moiety achieved by degradation...

There is an urgent need for novel strategies to fight drug resistance and multi-drug resistance. As alternative the classic antibiotic therapy, attenuation of bacteria virulence affecting their Quorum sensing (QS) system a promising approach. genetic regulation that allows communicate with each other coordinate group behaviors. A new γ-lactone capable inhibiting LasI/R QS system, plakofuranolactone (1), was discovered in extract marine sponge Plakortis cf. lita, its structure, including...

The thermophilic bacterium Thermoactinomyces vulgaris strain ISCAR 2354, isolated from a coastal hydrothermal vent in Iceland, was shown to contain thermoactinoamide A (1), new cyclic hexapeptide composed of mixed d and l amino acids, along with five minor analogues (2-6). structure 1 determined by one- two-dimensional NMR spectroscopy, high-resolution tandem mass spectrometry, advanced Marfey's analysis the products its partial hydrolysis. Thermoactinoamide inhibited growth Staphylococcus...

The halogenated alkaloid chloromethylhalicyclamine B (1), together with the known natural compound halicyclamine (2), was isolated from extract of sponge Acanthostrongylophora ingens. structure 1 determined by spectroscopic means, and it shown that is produced reaction 2 CH2Cl2 used for extraction. Compound a selective CK1δ/ε inhibitor an IC50 6 μM, while inactive. absolute configuration quantum mechanical calculation its ECD spectrum, this also previously unknown parent (2). Computational...

ADVERTISEMENT RETURN TO ISSUEPREVArticleNEXTChemistry of Verongida Sponges, II. Constituents the Caribbean Sponge Aplysina fistularis forma fulvaP. Ciminiello, V. Costantino, E. Fattorusso, S. Magno, A. Mangoni, and M. PansiniCite this: J. Nat. Prod. 1994, 57, 6, 705–712Publication Date (Print):June 1, 1994Publication History Published online1 July 2004Published inissue 1 June 1994https://pubs.acs.org/doi/10.1021/np50108a004https://doi.org/10.1021/np50108a004research-articleACS...

The bloom-forming cyanobacteria Trichodesmium sp. have been recently shown to produce some of the chlorinated peptides/polyketides previously isolated from marine sponge Smenospongia aurea. A comparative analysis extracts S. aurea and was performed using tandem mass spectrometry-based molecular networking. analysis, specifically targeted metabolites, showed that many them are common two organisms, but also general differences exist between metabolomes. Following this six new metabolites were...

Sponges harbor a remarkable diversity of microbial symbionts in which signal molecules can accumulate and enable cell-cell communication, such as quorum sensing (QS). Bacteria capable QS were isolated from marine sponges; however, an extremely small fraction the sponge microbiome is amenable to cultivation. We took advantage community genome assembly binning investigate uncultured majority symbionts. identified complete N-acyl-homoserine lactone (AHL)-QS system (designated TswIR) seven...

Chemotherapy represents the most applied approach to cancer treatment. Owing frequent onset of chemoresistance and tumor relapses, there is an urgent need discover novel more effective anticancer drugs. In search for therapeutic alternatives treat disease, a series hybrid pyrazolo[3,4-d]pyrimidin-4(5H)-ones tethered with hydrazide-hydrazones, 5a–h, was synthesized from condensation reaction pyrazolopyrimidinone-hydrazide 4 arylaldehydes in ethanol, acid catalysis. vitro assessment...

Unsaturated diacylglycerols are a class of antioxidant compounds with the potential to positively impact human health. Their ability combat oxidative stress through radical scavenger activity underscores their significance in context preventive and therapeutic strategies. In this paper we highlight role Anabaena flos-aquae as producer unsaturated mono diacylglycerols, then demonstrate its methanolic extract, which has main components variety acylglycerol analogues. This finding was revealed...

Chemical synthesis is commonly seen as the final proof of structure complex natural products, but even a seemingly easy and well-established synthetic procedure may lead to an unexpected result. This what happened with thermoactinoamide A (1a), antimicrobial antitumor nonribosomal cyclic hexapeptide produced by thermophilic bacterium Thermoactinomyces vulgaris. The outsourced company one described in paper showed spectroscopic data identical each other different from those product. After...

Abstract Siderophores are low-molecular-weight compounds excreted by microorganisms to facilitate iron uptake in times of its unavailability. Microbes may produce siderophores monopolize and achieve competitive exclusion other strains. Alternatively, be exchanged for substrates mutualistic relationships. that employ β -hydroxy-aspartate ( -OH-Asp) chelation were shown undergo UV-mediated photolytic cleavage with simultaneous reduction Fe 3+ 2+ . Photolytic can mediate algal-bacterial...