title: Minutissamides A-D, antiproliferative cyclic decapeptides from the cultured cyanobacterium Anabaena minutissima.
abstract: Four cyclic decapeptides, minutissamides A-D (1-4), were isolated from the cultured cyanobacterium Anabaena minutissima (UTEX 1613). The planar structures were determined using various spectroscopic techniques including HRESIMS and 1D and 2D NMR experiments. The absolute configurations of the α-amino acid residues were assigned using Marfey's method after acid hydrolysis. The absolute configuration of a β-amino acid residue was assigned by a combination of the advanced Marfey's method, J-based configurational analysis, and ROE spectroscopic analysis. The structures of minutissamides A-D (1-4) were characterized by the presence of three nonstandard α-amino acid residues (two α,β-dehydro-α-aminobutyric acids and one N-methylated Asn) and one β-amino acid residue (2-hydroxy-3-amino-4-methyldodecanoic acid or 2-hydroxy-3-amino-4-methylhexadecanoic acid). Minutissamides A-D (1-4) exhibited antiproliferative activity against the HT-29 human colon cancer cell line with IC₅₀ values of 2.0, 20.0, 11.8, and 22.7 μM, respectively.
authors.affiliation: Department of Medicinal Chemistry and Pharmacognosy, University of Illinois at Chicago , 833 S. Wood Street, Chicago, Illinois 60612, USA.
authors.forename: Hahk-Soo
authors.initials: HS
authors.lastname: Kang
authors.forename: Aleksej
authors.initials: A
authors.lastname: Krunic
authors.forename: Qi
authors.initials: Q
authors.lastname: Shen
authors.forename: Steven M
authors.initials: SM
authors.lastname: Swanson
authors.forename: Jimmy
authors.initials: J
authors.lastname: Orjala
mesh_terms: D017033:Anabaena / Q000737:chemistry*; D000970:Antineoplastic Agents / Q000737:chemistry / Q000302:isolation & purification* / Q000494:pharmacology*; D004354:Drug Screening Assays, Antitumor; D019073:HT29 Cells; D006801:Humans; D020128:Inhibitory Concentration 50; D015394:Molecular Structure; D019906:Nuclear Magnetic Resonance, Biomolecular; D010456:Peptides, Cyclic / Q000737:chemistry / Q000302:isolation & purification* / Q000494:pharmacology*
chemical_list: D000970:Antineoplastic Agents; D010456:Peptides, Cyclic