Structural characterization and antimicrobial evaluation of atractyloside, atractyligenin, and 15-didehydroatractyligenin methyl ester

Brucoli, Federico, Borrello, Maria T., Stapleton, Paul, Parkinson, Gary N. and Gibbons, Simon (2012) Structural characterization and antimicrobial evaluation of atractyloside, atractyligenin, and 15-didehydroatractyligenin methyl ester. Journal of Natural Products, 75 (6). pp. 1070-1075. ISSN 0163-3864

Full text not available from this repository. (Request a copy)

Abstract

We report the first complete structure elucidation of the ent-kaurane diterpenoid glycoside atractyloside (1) by means of NMR and X-ray diffractometry techniques. Extensive one- and two-dimensional NMR experiments were employed to assign the proton and carbon signals of 1, and crystallography experiments established the configurations of all stereogenic centers. Furthermore, we present a novel semisynthetic route for the preparation of the highly cytotoxic aglycone derivative of 1, 15-didehydroatractyligenin methyl ester (3). All compounds were tested for their antibiotic activity against Enterococcus faecalis, Escherichia coli, and several strains of Staphylococcus aureus, including fluoroquinoloneresistant (SA1199B) and two epidemic MRSA (EMRSA-15 and -16) strains. Compound 3 exhibited moderate activity against all of the Staph. aureus strains with an MIC value of 128 mg/L.

Item Type: Article
Uncontrolled Keywords: analytical chemistry,molecular medicine,pharmacology,pharmaceutical science,drug discovery,complementary and alternative medicine,organic chemistry ,/dk/atira/pure/subjectarea/asjc/1600/1602
Faculty \ School: Faculty of Science > School of Pharmacy
Related URLs:
Depositing User: LivePure Connector
Date Deposited: 15 Jul 2020 23:38
Last Modified: 15 Jul 2020 23:38
URI: https://ueaeprints.uea.ac.uk/id/eprint/76089
DOI: 10.1021/np300080w

Actions (login required)

View Item View Item