Dihydro-β-agarofuran sesquiterpenes isolated from Celastrus vulcanicola as potential anti-Mycobacterium tuberculosis multidrug-resistant agents

David Torres-Romero, Ignacio A. Jiménez, Rosario Rojas, Robert H. Gilman, Matías López, Isabel L. Bazzocchi

Research output: Contribution to journalArticlepeer-review

Abstract

In the present study, we report four new dihydro-β-agarofuran sesquiterpenes (1-4), which were isolated from the leaves of Celastrus vulcanicola, in addition to five derivatives (5-9). Their stereostructures were elucidated on the basis of spectroscopic analysis, including 1D and 2D NMR techniques, X-ray studies, chemical correlations and biogenetic means. Compounds 1-9 and the previously reported sesquiterpenes 10-25 have been tested as potential antimycobacterial agents against sensitive and resistant Mycobacterium tuberculosis strains. 1α-Acetoxy-6β,9β-dibenzoyloxy-dihydro- β-agarofuran (20) exhibited antituberculosis activity against the MDR TB strain with a MIC value of 6.2 μg/mL, comparable to or better than isoniazid or rifampin, two of the best first-line drugs commonly used in the treatment of TB. The structure-activity relationship is discussed.

Original languageEnglish (US)
Pages (from-to)2182-2189
Number of pages8
JournalBioorganic and Medicinal Chemistry
Volume19
Issue number7
DOIs
StatePublished - Apr 1 2011

Keywords

  • Celastrus vulcanicola
  • Multidrug-resistant
  • Mycobacterium tuberculosis
  • Sesquiterpenes

ASJC Scopus subject areas

  • Biochemistry
  • Molecular Medicine
  • Molecular Biology
  • Pharmaceutical Science
  • Drug Discovery
  • Clinical Biochemistry
  • Organic Chemistry

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