title: Novel lipoxygenase inhibitors, tetrapetalone B, C, and D from Streptomyces sp.
abstract: Three novel lipoxygenase inhibitors, tetrapetalone B (2, C(28)H(35)NO(9)), C (3, C(26)H(34)NO(8)), and D (4, C(28)H(36)NO(10)), were isolated from a culture broth of Streptomyces sp. USF-4727 that produced a lipoxygenase inhibitor tetrapetalone A (1) simultaneously. Each chemical structure was revealed by spectroscopic evidence, this suggests that these three compounds are structurally related to 1. They had a tetracyclic skeleton and a beta-D-rhodinosyl moiety. Tetrapetalone B, C, and D inhibited soybean lipoxygenase with IC(50): 320, 360, and 340 microM respectively.
authors.affiliation: Laboratory of Applied Microbiology, School of Food and Nutritional Sciences, University of Shizuoka, Yada, Japan.
authors.forename: Toshikazu
authors.initials: T
authors.lastname: Komoda
authors.forename: Madoka
authors.initials: M
authors.lastname: Kishi
authors.forename: Naoki
authors.initials: N
authors.lastname: Abe
authors.forename: Yasumasa
authors.initials: Y
authors.lastname: Sugiyama
authors.forename: Akira
authors.initials: A
authors.lastname: Hirota
mesh_terms: D003978:Diazomethane / Q000494:pharmacology; D006027:Glycosides / Q000737:chemistry* / Q000302:isolation & purification / Q000494:pharmacology; D006576:Heterocyclic Compounds, 4 or More Rings / Q000737:chemistry* / Q000302:isolation & purification / Q000494:pharmacology; D020128:Inhibitory Concentration 50; D007536:Isomerism; D008084:Lipoxygenase / Q000378:metabolism; D016859:Lipoxygenase Inhibitors / Q000737:chemistry* / Q000302:isolation & purification / Q000494:pharmacology; D009682:Magnetic Resonance Spectroscopy; D008745:Methylation / Q000187:drug effects; D015394:Molecular Structure; D013025:Glycine max / Q000201:enzymology; D013302:Streptomyces / Q000737:chemistry*
chemical_list: D006027:Glycosides; D006576:Heterocyclic Compounds, 4 or More Rings; D016859:Lipoxygenase Inhibitors; C494870:tetrapetalone B; C494871:tetrapetalone C; C494872:tetrapetalone D; D003978:Diazomethane; D008084:Lipoxygenase