title: Biosynthesis of tetrapetalones.
abstract: The biosynthesis of tetrapetalones (tetrapetalones A, B, C, and D) in Streptomyces sp. USF-4727 was studied by feeding experiments with [1-13C] sodium propanoate, [1-13C] sodium butanoate, [carbonyl-13C] 3-amino-5-hydroxybenzoic acid (AHBA) hydrochloride, and [1-13C] glucose, followed by analysis of the 13C-NMR spectra. These feeding experiments revealed that the four tetrapetalones were polyketide compounds constructed from propanoate, butanoate, AHBA, and glucose. The tetrapetalone biosynthetic pathway was also suggested in this study. In this pathway, tetrapetalone A (1) is synthesized by polyketide synthase (PKS) using AHBA as a starter unit, then the side chain of 1 is subjected to acetoxylation to produce tetrapetalone B (2). Additionally, 1 is oxidized and transformed into tetrapetalone C (3). In a similar way, 2 is converted to tetrapetalone D (4). Therefore, the biosynthetic relationship of the four tetrapetalones was indicated.
authors.affiliation: Laboratory of Applied Microbiology, School of Food and Nutritional Sciences, University of Shizuoka, Shizuoka, Japan 422-8526. komoda@myu.ac.jp
authors.forename: Toshikazu
authors.initials: T
authors.lastname: Komoda
authors.forename: Yasumasa
authors.initials: Y
authors.lastname: Sugiyama
authors.forename: Akira
authors.initials: A
authors.lastname: Hirota
mesh_terms: D062365:Aminobenzoates / Q000737:chemistry*; D002247:Carbon Isotopes; D002626:Chemistry, Pharmaceutical / Q000379:methods; D005947:Glucose / Q000737:chemistry / Q000378:metabolism; D006027:Glycosides / Q000096:biosynthesis* / Q000737:chemistry; D006576:Heterocyclic Compounds, 4 or More Rings / Q000737:chemistry; D006861:Hydrogen Peroxide / Q000494:pharmacology; D062385:Hydroxybenzoates; D006885:Hydroxybutyrates / Q000737:chemistry; D009682:Magnetic Resonance Spectroscopy; D008956:Models, Chemical; D019346:Sodium Acetate / Q000737:chemistry; D013053:Spectrophotometry; D013302:Streptomyces / Q000378:metabolism
chemical_list: D062365:Aminobenzoates; D002247:Carbon Isotopes; D006027:Glycosides; D006576:Heterocyclic Compounds, 4 or More Rings; D062385:Hydroxybenzoates; D006885:Hydroxybutyrates; C492598:tetrapetalone A; C494870:tetrapetalone B; C494871:tetrapetalone C; C494872:tetrapetalone D; D019346:Sodium Acetate; C031509:3-amino-5-hydroxybenzoic acid; D006861:Hydrogen Peroxide; D005947:Glucose