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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

(A) Fluorescence spectra of compound (1) (2 μM) upon addition of DNA duplex; (B) The Job plot obtained from the fluorescence response upon DNA binding.
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marinedrugs-13-01290-f007: (A) Fluorescence spectra of compound (1) (2 μM) upon addition of DNA duplex; (B) The Job plot obtained from the fluorescence response upon DNA binding.

Mentions: In order to see the compound’s potentials as anticancer agents or gene expression modulators, we also explored the DNA-binding properties of lumazine peptides using fluorescence spectroscopy. Figure 7 demonstrates the fluorescence decrease upon adding double-stranded DNA oligomers containing sequences from the tetO promoter region. The terrelumamide A (1) exhibited strong emission peak at around 400 nm by exciting at 260 nm, which gradually decreased upon addition of DNA duplex. The Job plot analyzed from the fluorescence spectra of the titration suggests that the stoichiometry of the compound-DNA complex is 2:1, indicating two binding sites within the 48 bp DNA sequence. Based on the stoichiometry we observed, it appears to have a combined binding mode; intercalation by terrelumamide A along with groove binding by the peptide backbone. The results may suggest a new direction to explore biological activities of lumazine peptides.


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)

(A) Fluorescence spectra of compound (1) (2 μM) upon addition of DNA duplex; (B) The Job plot obtained from the fluorescence response upon DNA binding.
© Copyright Policy
Related In: Results  -  Collection

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

marinedrugs-13-01290-f007: (A) Fluorescence spectra of compound (1) (2 μM) upon addition of DNA duplex; (B) The Job plot obtained from the fluorescence response upon DNA binding.
Mentions: In order to see the compound’s potentials as anticancer agents or gene expression modulators, we also explored the DNA-binding properties of lumazine peptides using fluorescence spectroscopy. Figure 7 demonstrates the fluorescence decrease upon adding double-stranded DNA oligomers containing sequences from the tetO promoter region. The terrelumamide A (1) exhibited strong emission peak at around 400 nm by exciting at 260 nm, which gradually decreased upon addition of DNA duplex. The Job plot analyzed from the fluorescence spectra of the titration suggests that the stoichiometry of the compound-DNA complex is 2:1, indicating two binding sites within the 48 bp DNA sequence. Based on the stoichiometry we observed, it appears to have a combined binding mode; intercalation by terrelumamide A along with groove binding by the peptide backbone. The results may suggest a new direction to explore biological activities of lumazine peptides.

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