Chemistry and Biology of Bengamides and Bengazoles, Bioactive Natural Products from Jaspis Sponges

  title={Chemistry and Biology of Bengamides and Bengazoles, Bioactive Natural Products from Jaspis Sponges},
  author={Cristina Garc{\'i}a-Ruiz and Francisco Sarabia},
  journal={Marine Drugs},
  pages={1580 - 1622}
Sponges corresponding to the Jaspidae family have proved to be a prolific source of bioactive natural products. Among these, the bengamides and the bengazoles stand out by virtue of their unprecedented molecular architectures and impressive biological profiles, including antitumor, antibiotic and anthelmintic properties. As a consequence, intense research activity has been devoted to these compounds from both chemical and biological standpoints. This review describes in detail the research into… 
Marine sponges of the genus Stelletta as promising drug sources: chemical and biological aspects☆
The Development of the Bengamides as New Antibiotics against Drug-Resistant Bacteria.
The evolution of the bengamides from their initial exploration as antitumor agents up to their current status as antibiotics is described in detail, highlighting the manifold value of these marine natural products as valid hits in medicinal chemistry.
Production of the Bengamide Class of Marine Natural Products in Myxobacteria: Biosynthesis and Structure-Activity Relationships.
A combination of semisynthesis of microbially derived bengamides and total synthesis resulted in an optimized derivative that combined high cellular potency in the nanomolar range with high metabolic stability, which translated to an improved half-life in mice and antitumor efficacy in a melanoma mouse model.
The Bengamides: A Mini-Review of Natural Sources, Analogues, Biological Properties, Biosynthetic Origins, and Future Prospects
It is highlighted that the bengamides have driven inspirational studies and that they will remain relevant for future research, even 30 years after the discovery of the first structures, and could build on their nanomolar in vitro and positive in vivo antiproliferative and antiangiogenic properties.
Identification of Antimycobacterial Natural Products from a Library of Marine Invertebrate Extracts
This study establishes the bengamides as potent antitubercular compounds, with the first report of whole-cell antitubcular activity of bengAmides P 2 and Q 3, as well as several organic and aqueous marine invertebrate extracts screened for in vitro inhibitory activity against Mycobacterium tuberculosis.
Natural products from myxobacteria: novel metabolites and bioactivities.
New natural products that were isolated from myxobacteria in the period of 2011 to July 2016 are reported on.
Biological Activity of Recently Discovered Halogenated Marine Natural Products
This review presents the biological activity—antibacterial, antifungal, anti-parasitic, antiviral, antitumor, antiinflammatory, antioxidant, and enzymatic activity—of halogenated marine natural
Synthesis and Biological Evaluation of Modified Miuraenamides
Detailed SAR studies indicate, that bromination of the central tyrosine is essential for good biological activity, while the side chain of the C-terminal amino acid can be varied or can even be removed.
Synergistic Anti-Candida Activity of Bengazole A in the Presence of Bengamide A †
Results eliminate an azole-like MOA for the bengazoles, and suggest that another as-yet unidentified mechanism is operative, which is likely to be dose-dependent synergistic antifungal activity.
Computational investigation of marine bioactive compounds reveals frigocyclinone as a potent inhibitor of Kaposi’s Sarcoma Associated Herpesvirus (KSHV) targets
Molecular dynamic simulation studies revealed the stability of LANA1- Frigocyclinone complex and it could be a futuristic perspective chemical compound for Kaposi’s sarcoma.


Cytotoxic Metabolites from an Australian Collection of the Sponge Jaspis Species
Bengamides Y (1) and Z (3) showed a striking differential cytotoxicity pattern against a panel of 10 human tumor cell lines, with closely related cell lines displaying significant differences in sensitivity.
New structures and bioactivity patterns of bengazole alkaloids from a choristid marine sponge.
New bengazoles 3-9 as inseparable mixtures are reported from the sponge Jaspis cf. coricea collected in Papua New Guinea. These compounds contain a new variation of the unusual bisoxazole core
Antifungal metabolites from the marine sponge Pachastrissa sp.: new bengamide and bengazole derivatives.
The studies of components of an undescribed sponge in the genus Pachastrissa sp.
A new cytotoxic and tubulin-interactive milnamide derivative from a marine sponge Cymbastela sp.
The cytotoxic and antitubulin activities of milnamide D were evaluated and the structure was solved by interpretation of NMR and mass spectra data.
Design, Synthesis, and Biological Evaluation of Caprolactam‐Modified Bengamide Analogues
The sponge-derived bengamides, first isolated by Crews and co-workers in 1986, have a unique molecular structure and a broad array of biological activities that include antitumor, antibiotic, and
Bengazoles C-G from the Sponge Jaspis sp. Synthesis of the Side Chain and Determination of Absolute Configuration.
Five new antifungal bengazoles (C-G) were isolated and fully characterized from a marine sponge of the genus Jaspis sp, comprising a homologous series of n, iso, and anteiso fatty acid esters of the same heterocyclic bis(oxazolyl)methanol parent.
Total synthesis of potent antifungal marine bisoxazole natural products bengazoles A and B.
Total syntheses of bengazole A and B are described, which contain a sensitive stereogenic centre at this position between the two oxazoles, which provides rapid access to single stereoisomers of the complex natural products and allows the synthesis of analogues for biological evaluation.