Biosynthesis of tetrapetalones.
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.
Komoda
Toshikazu
T
Laboratory of Applied Microbiology, School of Food and Nutritional Sciences, University of Shizuoka, Shizuoka, Japan 422-8526. komoda@myu.ac.jp
Sugiyama
Yasumasa
Y
Hirota
Akira
A
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
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