Trichormamides A and B with Antiproliferative Activity from the Cultured Freshwater Cyanobacterium Trichormus sp. UIC 10339.

Abstract

Two new cyclic lipopeptides, trichormamides A (1) and B (2), were isolated from the cultured freshwater cyanobacterium Trichormus sp. UIC 10339. The strain was obtained from a sample collected in Raven Lake in Northern Wisconsin. The planar structures of trichormamides A (1) and B (2) were determined using a combination of spectroscopic analyses including HRESIMS and 1D and 2D NMR experiments. The absolute configurations of the amino acid residues were assigned by the advanced Marfey's method after acid hydrolysis. Trichormamide A (1) is a cyclic undecapeptide containing two D-amino acid residues (D-Tyr and D-Leu) and one β-amino acid residue (β-aminodecanoic acid). Trichormamide B (2) is a cyclic dodecapeptide characterized by the presence of four nonstandard α-amino acid residues (homoserine, N-methylisoleucine, and two 3-hydroxyleucines) and one β-amino acid residue (β-aminodecanoic acid). Trichormamide B (2) was cytotoxic against MDA-MB-435 and HT-29 cancer cell lines with IC50 values of 0.8 and 1.5 μM, respectively.

• Authors: Shangwen Luo, Aleksej Krunic, Hahk-Soo Kang, Wei-Lun Chen, John L Woodard, James R Fuchs, Steven M Swanson, Jimmy Orjala
• Journal: Journal of natural products (J Nat Prod) Vol. 77 Issue 8 Pg. 1871-80 (Aug 22 2014) ISSN: 1520-6025 [Electronic] United States
• PMID: 25089652 (Publication Type: Journal Article, Research Support, N.I.H., Extramural)

Chemical References

• Amino Acids
• Antineoplastic Agents
• Lipopeptides
• Peptides, Cyclic
• trichormamide A
• trichormamide B

Topics

• Amino Acids (chemistry)
• Antineoplastic Agents (chemistry, isolation & purification, pharmacology)
• Cyanobacteria (chemistry)
• Drug Screening Assays, Antitumor
• Fresh Water (microbiology)
• HT29 Cells
• Humans
• Inhibitory Concentration 50
• Lipopeptides (chemistry, isolation & purification, pharmacology)
• Molecular Structure
• Nuclear Magnetic Resonance, Biomolecular
• Peptides, Cyclic (chemistry, isolation & purification, pharmacology)
• Wisconsin