title: Minutissamides E-L, antiproliferative cyclic lipodecapeptides from the cultured freshwater cyanobacterium cf. Anabaena sp.
abstract: The extract of UIC 10035, a strain obtained from a sample collected near the town of Homestead, South Florida, showed antiproliferative activity against MDA-MB-435 cells. Bioassay-guided fractionation led to the isolation of a series of cyclic lipodecapeptides, named minutissamides E-L (1-8). The planar structures were determined by analysis of HRESIMS, tandem MS, and 1D and 2D NMR data, and the stereoconfigurations were assigned by LC-MS analysis of the Marfey's derivatives after acid hydrolysis. Minutissamides E-L (1-8) exhibited antiproliferative activity against MDA-MB-435 cells with IC(50) values ranging between 1 and 10 μM. The structures of minutissamides E-L (1-8) were closely related with those of the previously reported lipopeptides, puwainaphycins A-E and minutissamides A-D, characterized by the presence of a lipophilic β-amino acid and three non-standard amino acids NMeAsn, OMeThr and Dhb (α,β-dehydro-α-aminobutyric acid). The strain UIC 10035 was designated as cf. Anabaena sp. on the basis of morphological and 16S rRNA gene sequence analyses.
authors.affiliation: Department of Medicinal Chemistry and Pharmacognosy, University of Illinois at Chicago, Chicago, IL 60612, USA.
authors.forename: Hahk-Soo
authors.initials: HS
authors.lastname: Kang
authors.forename: Megan
authors.initials: M
authors.lastname: Sturdy
authors.forename: Aleksej
authors.initials: A
authors.lastname: Krunic
authors.forename: Hyunjung
authors.initials: H
authors.lastname: Kim
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* / Q000145:classification; D000900:Anti-Bacterial Agents / Q000737:chemistry / Q000302:isolation & purification / Q000494:pharmacology; D045744:Cell Line, Tumor; D049109:Cell Proliferation / Q000187:drug effects; D005618:Fresh Water / Q000382:microbiology; D006090:Gram-Negative Bacteria / Q000187:drug effects; D006094:Gram-Positive Bacteria / Q000187:drug effects; D006801:Humans; D055666:Lipopeptides / Q000737:chemistry* / Q000302:isolation & purification / Q000633:toxicity; D009682:Magnetic Resonance Spectroscopy; D008968:Molecular Conformation; D010802:Phylogeny; D012336:RNA, Ribosomal, 16S / Q000235:genetics; D053719:Tandem Mass Spectrometry
chemical_list: D000900:Anti-Bacterial Agents; D055666:Lipopeptides; D012336:RNA, Ribosomal, 16S