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

Federico Brucoli, Maria T. Borrello, Paul Stapleton, Gary N. Parkinson, Simon Gibbons

Research output: Contribution to journalArticlepeer-review

11 Citations (Scopus)

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.

Original languageEnglish
Pages (from-to)1070-1075
Number of pages6
JournalJournal of Natural Products
Volume75
Issue number6
Early online date17 May 2012
DOIs
Publication statusPublished - 22 Jun 2012

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