TY - JOUR
T1 - Dihydro-β-agarofuran sesquiterpenes isolated from Celastrus vulcanicola as potential anti-Mycobacterium tuberculosis multidrug-resistant agents
AU - Torres-Romero, David
AU - Jiménez, Ignacio A.
AU - Rojas, Rosario
AU - Gilman, Robert H.
AU - López, Matías
AU - Bazzocchi, Isabel L.
N1 - Funding Information:
This work was supported by the Agencia Canaria de Investigación, Innovación y Sociedad de la Información (C200801000049), and PCI-Iberoamérica (A/023081/09, AECID) projects, and the antimycobacterial study was financed by project SIDISI50989. D.T.R. thanks the Gobierno Autónomo de Canarias for the “Antonio González” fellowship and the Servicio de Parques Nacionales y Vida Silvestre, Dirección de Recursos Renovables del Ministerio de Agricultura y Ganadería (MAG) and Fundación Ecológica de El Salvador (SALVANATURA) for supplying the plant material.
PY - 2011/4/1
Y1 - 2011/4/1
N2 - 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.
AB - 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.
KW - Celastrus vulcanicola
KW - Multidrug-resistant
KW - Mycobacterium tuberculosis
KW - Sesquiterpenes
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U2 - 10.1016/j.bmc.2011.02.034
DO - 10.1016/j.bmc.2011.02.034
M3 - Article
C2 - 21419633
AN - SCOPUS:79953197170
SN - 0968-0896
VL - 19
SP - 2182
EP - 2189
JO - Bioorganic and Medicinal Chemistry
JF - Bioorganic and Medicinal Chemistry
IS - 7
ER -