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1.
Nat Prod Rep ; 41(3): 347-369, 2024 Mar 20.
Article in English | MEDLINE | ID: mdl-38088806

ABSTRACT

Covering: 2000 to 2023Cyanobacteria produce a variety of bioactive natural products that can pose a threat to humans and animals as environmental toxins, but also have potential for or inspire pharmaceutical use. As oxygenic phototrophs, cyanobacteria furthermore hold great promise for sustainable biotechnology. Yet, the necessary tools for exploiting their biotechnological potential have so far been established only for a few model strains of cyanobacteria, while large untapped biosynthetic resources are hidden in slow-growing cyanobacterial genera that are difficult to access by genetic techniques. In recent years, several approaches have been developed to circumvent the bottlenecks in cyanobacterial natural product research. Here, we summarize current progress that has been made in unlocking or characterizing cryptic metabolic pathways using integrated omics techniques, orphan gene cluster activation, use of genetic approaches in original producers, heterologous expression and chemo-enzymatic techniques. We are mainly highlighting genomic mining concepts and strategies towards high-titer production of cyanobacterial natural products from the last 10 years and discuss the need for further research developments in this field.


Subject(s)
Biological Products , Cyanobacteria , Animals , Humans , Biological Products/pharmacology , Biological Products/metabolism , Cyanobacteria/genetics , Cyanobacteria/metabolism , Biotechnology , Genomics
2.
Org Biomol Chem ; 20(5): 1031-1040, 2022 02 02.
Article in English | MEDLINE | ID: mdl-35018938

ABSTRACT

An abundant sponge of the order Bubarida was selected for further chemical investigation following biological and chemical screening of sponges collected from Futuna Islands in the Indo-Pacific. Ten new nitrogenous bisabolene derivatives were isolated and identified: the monomeric theonellin formamide analogues named bubaridins A-F (1-6) with unusual oxidised linear chains, and the first isocyanide/formamide dimeric and cyclised bisabolenes 7-9. The structure elucidation of these nitrogenous bisabolenes involved HRESIMS, NMR, and ECD analyses, and the chiral compounds were found to be racemates. A biosynthetic hypothesis for the production of these metabolites is proposed and some chemotaxonomic considerations are discussed. Furthermore, the antimicrobial and antitumoral activity were evalutated and the trans-dimer theonellin isocyanide (7) was shown to exhibit potent and selective antifungal activity.


Subject(s)
Antifungal Agents/pharmacology , Cyclohexylamines/pharmacology , Monocyclic Sesquiterpenes/pharmacology , Porifera/chemistry , Animals , Antifungal Agents/chemistry , Antifungal Agents/isolation & purification , Candida/drug effects , Cell Line, Tumor , Cyclohexylamines/chemical synthesis , Cyclohexylamines/isolation & purification , Humans , Islands , Microbial Sensitivity Tests , Molecular Structure , Monocyclic Sesquiterpenes/chemistry , Monocyclic Sesquiterpenes/isolation & purification , Pacific Ocean
3.
J Nat Prod ; 83(7): 2299-2304, 2020 07 24.
Article in English | MEDLINE | ID: mdl-32628481

ABSTRACT

The chemical investigation of the sponge Stylissa aff. carteri collected around Futuna Islands in the Pacific Ocean led to the isolation of three new dimeric pyrrole 2-aminoimidazole alkaloids (PIAs). Futunamine (1) features an unprecedented pyrrolo[1,2-c]imidazole core, while two other new dimeric PIAs were identified as analogues of palau'amine. Together with other known PIAs isolated from this species, they were shown to exhibit anti-inflammatory and neuroprotective activities.


Subject(s)
Alkaloids/chemistry , Imidazoles/chemistry , Pyrroles/chemistry , Alkaloids/isolation & purification , Alkaloids/pharmacology , Anti-Inflammatory Agents/pharmacology , Cell Line, Tumor , Humans , Imidazoles/isolation & purification , Islands , Microglia/cytology , Microglia/drug effects , Molecular Structure , Neuroprotective Agents/pharmacology , Pacific Ocean , Pyrroles/isolation & purification , Spectrum Analysis/methods
4.
Mar Drugs ; 17(6)2019 May 30.
Article in English | MEDLINE | ID: mdl-31151240

ABSTRACT

So far, the Futuna Islands located in the Central Indo-Pacific Ocean have not been inventoried for their diversity in marine sponges and associated chemical diversity. As part of the Tara Pacific expedition, the first chemical investigation of the sponge Narrabeena nigra collected around the Futuna Islands yielded 18 brominated alkaloids: seven new bromotryptamine derivatives 1-7 and one new bromotyramine derivative 8 together with 10 known metabolites of both families 9-18. Their structures were deduced from extensive analyses of nuclear magnetic resonance (NMR) and high-resolution mass spectrometry (HRMS) data. In silico metabolite anticipation using the online tool MetWork revealed the presence of a key and minor biosynthetic intermediates. These 18 compounds showed almost no cytotoxic effect up to 10 µM on human neuroblastoma SH-SY5Y and microglia BV2 cells, and some of them exhibited an interesting neuroprotective activity by reducing oxidative damage.


Subject(s)
Alkaloids/chemistry , Alkaloids/pharmacology , Oxidative Stress/drug effects , Porifera/chemistry , Alkaloids/isolation & purification , Alkaloids/toxicity , Animals , Cell Line, Tumor , Cell Survival/drug effects , Computer Simulation , Humans , Internet , Magnetic Resonance Spectroscopy , Mass Spectrometry , Mice , Neuroprotective Agents/chemistry , Neuroprotective Agents/isolation & purification , Neuroprotective Agents/pharmacology , Pacific Ocean , Tropical Climate
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