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Lumazine peptides from the marine-derived fungus Aspergillus terreus.

You M, Liao L, Hong SH, Park W, Kwon DI, Lee J, Noh M, Oh DC, Oh KB, Shin J - Mar Drugs (2015)

Bottom Line: From the results of combined spectroscopic and chemical analyses, the structures of these compounds were determined to be linear assemblies of 1-methyllumazine-6-carboxylic acid, an amino acid residue and anthranilic acid methyl ester connected by peptide bonds.These new compounds exhibited pharmacological activity by improving insulin sensitivity, which was evaluated in an adipogenesis model using human bone marrow mesenchymal stem cells.In addition, the compounds exhibited fluorescence changes upon binding to DNA, demonstrating their potential applications to DNA sequence recognition.

View Article: PubMed Central - PubMed

Affiliation: Natural Products Research Institute, College of Pharmacy, Seoul National University, San 56-1, Sillim, Gwanak, Seoul 151-742, Korea. lovemin90@snu.ac.kr.

ABSTRACT
Terrelumamides A (1) and B (2), two new lumazine-containing peptides, were isolated from the culture broth of the marine-derived fungus Aspergillus terreus. From the results of combined spectroscopic and chemical analyses, the structures of these compounds were determined to be linear assemblies of 1-methyllumazine-6-carboxylic acid, an amino acid residue and anthranilic acid methyl ester connected by peptide bonds. These new compounds exhibited pharmacological activity by improving insulin sensitivity, which was evaluated in an adipogenesis model using human bone marrow mesenchymal stem cells. In addition, the compounds exhibited fluorescence changes upon binding to DNA, demonstrating their potential applications to DNA sequence recognition.

No MeSH data available.


Related in: MedlinePlus

The ESI-LC/MS profile of crude extract.
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marinedrugs-13-01290-f002: The ESI-LC/MS profile of crude extract.

Mentions: The crude extract from this fungal strain was analyzed using ESI-LC/MS which was shown in Figure 2. And the procedure from marine sediments collection to bioactive compounds was also shown in Figure 3. The molecular formula of terrelumamide A (1) was determined to be C20H20O7N6 based on HRFABMS analysis. The highly unsaturated nature of this compound was indicated by the fourteen degree of unsaturation present in the mass data, and by the presence of signals from fifteen carbons in the aromatic and carbonyl regions in the 13C NMR data. This interpretation was consistent with the strong absorption bands at 1708 and 1690 cm−1 in the IR spectrum. The presence of several absorption maxima at 220–340 nm (E band) in the UV spectrum also supported the presence of an aromatic moiety. The remaining carbons in the 13C NMR data were two methines and three methyl carbons in the upfield region (Table 1).


Lumazine peptides from the marine-derived fungus Aspergillus terreus.

You M, Liao L, Hong SH, Park W, Kwon DI, Lee J, Noh M, Oh DC, Oh KB, Shin J - Mar Drugs (2015)

The ESI-LC/MS profile of crude extract.
© Copyright Policy
Related In: Results  -  Collection

License
Show All Figures
getmorefigures.php?uid=PMC4377984&req=5

marinedrugs-13-01290-f002: The ESI-LC/MS profile of crude extract.
Mentions: The crude extract from this fungal strain was analyzed using ESI-LC/MS which was shown in Figure 2. And the procedure from marine sediments collection to bioactive compounds was also shown in Figure 3. The molecular formula of terrelumamide A (1) was determined to be C20H20O7N6 based on HRFABMS analysis. The highly unsaturated nature of this compound was indicated by the fourteen degree of unsaturation present in the mass data, and by the presence of signals from fifteen carbons in the aromatic and carbonyl regions in the 13C NMR data. This interpretation was consistent with the strong absorption bands at 1708 and 1690 cm−1 in the IR spectrum. The presence of several absorption maxima at 220–340 nm (E band) in the UV spectrum also supported the presence of an aromatic moiety. The remaining carbons in the 13C NMR data were two methines and three methyl carbons in the upfield region (Table 1).

Bottom Line: From the results of combined spectroscopic and chemical analyses, the structures of these compounds were determined to be linear assemblies of 1-methyllumazine-6-carboxylic acid, an amino acid residue and anthranilic acid methyl ester connected by peptide bonds.These new compounds exhibited pharmacological activity by improving insulin sensitivity, which was evaluated in an adipogenesis model using human bone marrow mesenchymal stem cells.In addition, the compounds exhibited fluorescence changes upon binding to DNA, demonstrating their potential applications to DNA sequence recognition.

View Article: PubMed Central - PubMed

Affiliation: Natural Products Research Institute, College of Pharmacy, Seoul National University, San 56-1, Sillim, Gwanak, Seoul 151-742, Korea. lovemin90@snu.ac.kr.

ABSTRACT
Terrelumamides A (1) and B (2), two new lumazine-containing peptides, were isolated from the culture broth of the marine-derived fungus Aspergillus terreus. From the results of combined spectroscopic and chemical analyses, the structures of these compounds were determined to be linear assemblies of 1-methyllumazine-6-carboxylic acid, an amino acid residue and anthranilic acid methyl ester connected by peptide bonds. These new compounds exhibited pharmacological activity by improving insulin sensitivity, which was evaluated in an adipogenesis model using human bone marrow mesenchymal stem cells. In addition, the compounds exhibited fluorescence changes upon binding to DNA, demonstrating their potential applications to DNA sequence recognition.

No MeSH data available.


Related in: MedlinePlus