title: Dihydro-β-agarofuran sesquiterpenes isolated from Celastrus vulcanicola as potential anti-Mycobacterium tuberculosis multidrug-resistant agents.
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.
authors.affiliation: Instituto Universitario de Bio-Orgánica Antonio González y, Departamento de Química Orgánica, Universidad de La Laguna, Avenida Astrofísico Francisco Sánchez 2, 38206 La Laguna, Tenerife, Spain.
authors.forename: David
authors.initials: D
authors.lastname: Torres-Romero
authors.forename: Ignacio A
authors.initials: IA
authors.lastname: Jiménez
authors.forename: Rosario
authors.initials: R
authors.lastname: Rojas
authors.forename: Robert H
authors.initials: RH
authors.lastname: Gilman
authors.forename: Matías
authors.initials: M
authors.lastname: López
authors.forename: Isabel L
authors.initials: IL
authors.lastname: Bazzocchi
mesh_terms: D000995:Antitubercular Agents / Q000737:chemistry* / Q000302:isolation & purification / Q000494:pharmacology*; D031247:Celastrus / Q000737:chemistry*; D018360:Crystallography, X-Ray; D024901:Drug Resistance, Multiple, Bacterial; D005663:Furans / Q000737:chemistry / Q000302:isolation & purification / Q000494:pharmacology; D008958:Models, Molecular; D015394:Molecular Structure; D009169:Mycobacterium tuberculosis / Q000187:drug effects*; D012717:Sesquiterpenes / Q000737:chemistry* / Q000302:isolation & purification / Q000494:pharmacology*; D013329:Structure-Activity Relationship
chemical_list: D000995:Antitubercular Agents; D005663:Furans; D012717:Sesquiterpenes