title: Structural analysis of a new cytotoxic demethylated analogue of neo-N-methylsansalvamide with a different peptide sequence produced by Fusarium solani isolated from potato.
abstract: A novel cytotoxic cyclic pentadepsipeptide, neosansalvamide, was produced by Fusarium solani KCCM90040 isolated from Fusarium -contaminated potato in Korea. The molecular formula of neosansalvamide was analyzed as C₃₂H₅₀N₄O₆ by electrospray ionization tandem mass spectrometry and combined structural analysis. The one- and two-dimensional nuclear magnetic resonance and absolute configuration of amino acid spectral data allowed for the resolution of cyclic five subunits linked in the following order: (S)-leucic acid, two L-leucine, L-valine, and L-phenylalanine, and this sequence shows a molecular structure as a new demethylated analogue of neo-N-methylsansalvamide but having a different peptide sequence. The cytotoxic effects of neosansalvamide were investigated by sulforhodamine B bioassay on four human cancer cell lines. The IC₅₀ value of neosansalvamide required to inhibit cell growth in vitro by 50% for A549 (lung cancer), SK-OV-3 (ovarian cancer), SK-MEL-2 (skin melanoma), and MES-SA (uterine sarcoma) cell lines were 11.70 ± 0.55, 10.38 ± 0.64, 13.99 ± 1.32, and 11.75 ± 0.13 μM, respectively (mean ± standard error).
authors.affiliation: Department of Food Science and Technology, Chung-Ang University, Anseong 456-756, Republic of Korea.
authors.forename: Hee-Seok
authors.initials: HS
authors.lastname: Lee
authors.forename: Chan
authors.initials: C
authors.lastname: Lee
mesh_terms: D000595:Amino Acid Sequence; D000970:Antineoplastic Agents / Q000737:chemistry* / Q000494:pharmacology; D002455:Cell Division / Q000187:drug effects; D045744:Cell Line, Tumor; D047630:Depsipeptides / Q000096:biosynthesis* / Q000737:chemistry* / Q000494:pharmacology; D005260:Female; D005670:Fusarium / Q000378:metabolism*; D006801:Humans; D008175:Lung Neoplasms; D009682:Magnetic Resonance Spectroscopy; D008545:Melanoma; D008745:Methylation; D015394:Molecular Structure; D010051:Ovarian Neoplasms; D010456:Peptides, Cyclic / Q000737:chemistry; D011198:Solanum tuberosum / Q000382:microbiology*; D021241:Spectrometry, Mass, Electrospray Ionization; D014594:Uterine Neoplasms
chemical_list: D000970:Antineoplastic Agents; D047630:Depsipeptides; C419331:N-Methylsansalvamide; D010456:Peptides, Cyclic; C574337:neosansalvamide