Aqabamycins A-G: novel nitro maleimides from a marine Vibrio species. I. Taxonomy, fermentation, isolation and biological activities

@article{AlZereini2010AqabamycinsAN,
  title={Aqabamycins A-G: novel nitro maleimides from a marine Vibrio species. I. Taxonomy, fermentation, isolation and biological activities},
  author={Wael A. Al-Zereini and C. B. Fondja Yao and Hartmut Laatsch and Heidrun Anke},
  journal={The Journal of Antibiotics},
  year={2010},
  volume={63},
  pages={297-301}
}
In a screening of marine bacteria, a Vibrio species isolated from the surface of the soft coral Sinularia polydactyla collected in the Red Sea was found to be a prolific producer of secondary metabolites with antibacterial and cytotoxic activities. Seven novel maleimide derivatives named aqabamycin A (1a), aqabamycin B (1b), aqabamycin C (1c), aqabamycin D (1d), aqabamycin E (1e and 1e′), aqabamycin F (1f) and aqabamycin G (2) were isolated together with several known metabolites such as 3… 
Aqabamycins A–G: novel nitro maleimides from a marine Vibrio species: II. Structure elucidation*
TLDR
The structures of secondary metabolites with antibacterial and cytotoxic activities produced by a marine Vibrio strain from the Red Sea were elucidated using NMR, MS spectra and by comparison with synthetic material.
Thalassospiramide G, a New γ-Amino-Acid-Bearing Peptide from the Marine Bacterium Thalassospira sp
TLDR
Thalassospiramides A and D inhibited nitric oxide (NO) production in lipopolysaccharide (LPS)-stimulated mouse macrophage RAW 264.7 cells, with IC50 values of 16.4 and 4.8 μM, respectively.
Isolation and Antibacterial Activity of Indole Alkaloids from Pseudomonas aeruginosa UWI-1
TLDR
This study demonstrated the extended metabolic capability of Pseudomonas aeruginosa in synthesizing new chemotypes of bioactive compounds and attempted to outline a possible route for bacterial synthesis.
Antimicrobial and antioxidant activities of a new benzamide from endophytic Streptomyces sp. YIM 67086
A new benzamide (1) and four known compounds (2–5) were isolated from endophytic Streptomyces YIM67086, and their structures were determined as 2-amino-3,4-dihydroxy-5-methoxybenzamide (1),
Synthesis and antifungal evaluation of a series of maleimides.
TLDR
Some maleimides can be used as potential lead compounds for developing novel antifungal agents against S. sclerotiorum, and results showed that compounds exhibiting log P values within the range 2.4-3.0 displayed the best results in terms of fungicidal activity.
Antibacterial Compounds from Marine Bacteria, 2010-2015.
TLDR
This review summarizes the reports on antibacterial compounds that have been obtained from marine-derived bacteria during the period 2010-2015, highlighting the fact that known natural products may be an important source of new antibacterial leads.
Aqabamycins A-G: Novel Nitro Maleimides from a Marine Vibrio Species. Part 1. Taxonomy, Fermentation, Isolation and Biological Activities.
Seven novel maleimide derivatives are isolated from the surface of the soft coral Sinularia polydactyla collected from the Red Sea.
Total Synthesis of Aqabamycin G, a Nitrophenyl Indolylmaleimide Marine Alkaloid from Vibrio sp. WMBA.
The first total synthesis of the marine alkaloid aqabamycin G is disclosed. The synthetic sequence involved the stepwise addition to maleimide of an indole motif and a substituted diazo-benzenoid
Antibacterial activity of marine bioluminescent bacteria
TLDR
Antibacterial compounds identified were indole, phenol, 2,4-bis(1,1-dimethylethyl),dibutyl phthalate, and 1,2-Benzenedicarboxylic acid, butyl octyl ester.
Production of Bioactive Secondary Metabolites by Marine Vibrionaceae
TLDR
This account underlines the pending potential for exploring new bacterial sources of bioactive compounds and the challenges related to their investigation, and highlights some of the most interesting structures from this group of bacteria.
...
...

References

SHOWING 1-10 OF 20 REFERENCES
Aqabamycins A–G: novel nitro maleimides from a marine Vibrio species: II. Structure elucidation*
TLDR
The structures of secondary metabolites with antibacterial and cytotoxic activities produced by a marine Vibrio strain from the Red Sea were elucidated using NMR, MS spectra and by comparison with synthetic material.
New indole alkaloids from the North Sea bacterium Vibrio parahaemolyticus Bio249.
TLDR
Several bis- and tris-indole derivatives were isolated from a North Sea bacterium that was closely related to Vibrio parahaemolyticus (98% homology) and all compounds were inactive against a range of bacteria and fungi.
Nitro derivatives from the Arctic ice bacterium Salegentibacter sp. isolate T436*
Twenty-five aromatic nitro, dinitro and trinitro compounds were isolated in low yields of less than 1 mg l−1 from a Salegentibacter sp. strain T436 derived from Arctic pack ice. Their structures were
New Aromatic Nitro Compounds from Salegentibacter sp. T436, an Arctic Sea Ice Bacterium: Taxonomy, Fermentation, Isolation and Biological Activities
TLDR
Nineteen aromatic nitro compounds were isolated from the culture broth of an Artic sea ice bacterium and 2-Nitro-4-(2′-nitroethenyl)-phenol was the most potent antimicrobial and cytotoxic substance.
Assays of the biological activities of guaiane sesquiterpenoids isolated from the fruit bodies of edible lactarius species.
  • H. Anke, O. Bergendorff, O. Sterner
  • Biology, Chemistry
    Food and chemical toxicology : an international journal published for the British Industrial Biological Research Association
  • 1989
A Tetrodotoxin-Producing Vibrio Strain, LM-1, from the Puffer Fish Fugu vermicularis radiatus
TLDR
It was demonstrated that the isolated bacterium produced TTX, 4-epi-TTX, and anhTTX during cultivation, suggesting that Vibrio strains are responsible for the toxification of the puffer fish.
Vibrindole A, a metabolite of the marine bacterium, Vibrio parahaemolyticus, isolated from the toxic mucus of the boxfish Ostracion cubicus.
The EtOAc extract of the whole culture medium of Vibrio parahaemolyticus, which inhabits the toxic mucus of the box fish Ostracion cubicus, afforded a new indole-derived natural product, vibrindole A
Occurrence of tetrodotoxin and anhydrotetrodotoxin in Vibrio sp. isolated from the intestines of a xanthid crab, Atergatis floridus.
TLDR
Results showed the production of TTX and anhydroTTX in the Vibrio sp.
Inhibitors of protein kinase C. 1. 2,3-Bisarylmaleimides.
TLDR
The design and synthesis of a series of novel inhibitors of protein kinase C (PKC) were derived from the structural lead provided by the indolocarbazoles, staurosporine and K252a, and 2,3-bisarylmaleimides were the most active.
The Himanimides, New Bioactive Compounds From Serpula Himantoides (Fr.)Karst.
TLDR
A screening of basidiomycete cultures from Chile for the production of antibiotics identified a Serpula himantoides strain as a producer of metabolites inhibiting the growth of bacteria and fungi, resulting in the isolation of four new antibiotics.
...
...