title: Janadolide, a Cyclic Polyketide-Peptide Hybrid Possessing a tert-Butyl Group from an Okeania sp. Marine Cyanobacterium.
abstract: Janadolide, a new cyclic polyketide-peptide hybrid possessing a tert-butyl group, was isolated from an Okeania sp. marine cyanobacterium. The gross structure was elucidated by spectroscopic analyses, and the absolute configurations of the amino acid moieties were determined by acid hydrolysis and chiral-phase HPLC analyses. The absolute configuration of the two stereogenic centers in the polyketide moiety was elucidated based on a combination of degradation reactions and spectroscopic analyses including the phenyl-glycine methyl ester method. Janadolide showed potent antitrypanosomal activity with an IC50 value of 47 nM without cytotoxicity against human cells at 10 μM.
authors.affiliation: Department of Chemistry, Keio University , 3-14-1 Hiyoshi, Kohoku-ku, Yokohama, Kanagawa 223-8522, Japan.
authors.forename: Hidetoshi
authors.initials: H
authors.lastname: Ogawa
authors.affiliation: Department of Chemistry, Keio University , 3-14-1 Hiyoshi, Kohoku-ku, Yokohama, Kanagawa 223-8522, Japan.
authors.forename: Arihiro
authors.initials: A
authors.lastname: Iwasaki
authors.affiliation: Department of Chemistry, Keio University , 3-14-1 Hiyoshi, Kohoku-ku, Yokohama, Kanagawa 223-8522, Japan.
authors.forename: Shinpei
authors.initials: S
authors.lastname: Sumimoto
authors.affiliation: Department of Chemistry, Keio University , 3-14-1 Hiyoshi, Kohoku-ku, Yokohama, Kanagawa 223-8522, Japan.
authors.forename: Yuki
authors.initials: Y
authors.lastname: Kanamori
authors.affiliation: Department of Chemistry and Life Science, Kogakuin University , 2665-1 Nakano, Hachioji, Tokyo 192-0015, Japan.
authors.forename: Osamu
authors.initials: O
authors.lastname: Ohno
authors.forename: Masato
authors.initials: M
authors.lastname: Iwatsuki
authors.forename: Aki
authors.initials: A
authors.lastname: Ishiyama
authors.forename: Rei
authors.initials: R
authors.lastname: Hokari
authors.forename: Kazuhiko
authors.initials: K
authors.lastname: Otoguro
authors.forename: Satoshi
authors.initials: S
authors.lastname: O̅mura
authors.affiliation: Department of Chemistry, Keio University , 3-14-1 Hiyoshi, Kohoku-ku, Yokohama, Kanagawa 223-8522, Japan.
authors.forename: Kiyotake
authors.initials: K
authors.lastname: Suenaga
mesh_terms: D002851:Chromatography, High Pressure Liquid; D000458:Cyanobacteria / Q000737:chemistry*; D004354:Drug Screening Assays, Antitumor; D006367:HeLa Cells; D006801:Humans; D008386:Marine Biology; D015394:Molecular Structure; D019906:Nuclear Magnetic Resonance, Biomolecular; D010456:Peptides, Cyclic / Q000737:chemistry / Q000302:isolation & purification* / Q000494:pharmacology; D061065:Polyketides / Q000737:chemistry / Q000302:isolation & purification* / Q000494:pharmacology; D014345:Trypanosoma / Q000187:drug effects*; D014346:Trypanosoma brucei brucei / Q000187:drug effects
chemical_list: D010456:Peptides, Cyclic; D061065:Polyketides; C000618453:janadolide