{"status":"ok","message-type":"work","message-version":"1.0.0","message":{"indexed":{"date-parts":[[2026,10,3]],"date-time":"2026-10-03T05:21:52Z","timestamp":1791004912991,"version":"4.1.0"},"reference-count":47,"publisher":"MDPI AG","issue":"9","license":[{"start":{"date-parts":[[2012,9,19]],"date-time":"2012-09-19T00:00:00Z","timestamp":1348012800000},"content-version":"vor","delay-in-days":0,"URL":"https:\/\/creativecommons.org\/licenses\/by\/3.0\/"}],"content-domain":{"domain":[],"crossmark-restriction":false},"short-container-title":["Molecules"],"abstract":"<jats:p>The main aim of this study was to isolate and characterize the active compounds from the hexane extract of the fruit peels of Citrus aurantiifolia, which showed activity against one sensitive and three monoresistant (isoniazid, streptomycin or ethambutol) strains of Mycobacterium tuberculosis H37Rv. The active extract was fractionated by column chromatography, yielding the following major compounds: 5-geranyloxypsoralen (1); 5-geranyloxy-7-methoxycoumarin (2); 5,7-dimethoxycoumarin (3); 5-methoxypsoralen (4); and 5,8-dimethoxypsoralen (5). The structures of these compounds were elucidated by 1D and 2D NMR spectroscopy. In addition, GC-MS analysis of the hexane extract allowed the identification of 44 volatile compounds, being 5,7-dimethoxycoumarin (15.79%), 3-methyl-1,2-cyclopentanedione (8.27%), 1-methoxy-ciclohexene (8.0%), corylone (6.93%), palmitic acid (6.89%), 5,8-dimethoxypsoralen (6.08%), a-terpineol (5.97%), and umbelliferone (4.36%), the major constituents. Four isolated coumarins and 16 commercial compounds identified by GC-MS were tested against M. tuberculosis H37Rv and three multidrug-resistant M. tuberculosis strains using the Microplate Alamar Blue Assay. The constituents that showed activity against all strains were 5 (MICs = 25\u201350 mg\/mL), 1 (MICs = 50\u2013100 mg\/mL), palmitic acid (MICs = 25\u201350 mg\/mL), linoleic acid (MICs = 50\u2013100 mg\/mL), oleic acid (MICs = 100 mg\/mL), 4-hexen-3-one (MICs = 50\u2013100 mg\/mL), and citral (MICs = 50\u2013100 mg\/mL). Compound 5 and palmitic acid were the most active ones. The antimycobacterial activity of the hexane extract of C. aurantifolia could be attributed to these compounds.<\/jats:p>","DOI":"10.3390\/molecules170911173","type":"journal-article","created":{"date-parts":[[2012,9,19]],"date-time":"2012-09-19T11:58:11Z","timestamp":1348055891000},"page":"11173-11184","update-policy":"https:\/\/doi.org\/10.3390\/mdpi_crossmark_policy","source":"Crossref","is-referenced-by-count":82,"title":["Chemical Composition of Hexane Extract of Citrus aurantifolia and Anti-Mycobacterium tuberculosis Activity of Some of Its Constituents"],"prefix":"10.3390","volume":"17","author":[{"given":"Nallely E.","family":"Sandoval-Montemayor","sequence":"first","affiliation":[{"name":"Facultad de Ciencias Qu\u00edmicas, Universidad Aut\u00f3noma de Nuevo Le\u00f3n, Av. Universidad S\/N, Ciudad Universitaria, San Nicol\u00e1s de los Garza CP 66451, Nuevo Le\u00f3n,Mexico"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Abraham","family":"Garc\u00eda","sequence":"additional","affiliation":[{"name":"Facultad de Ciencias Qu\u00edmicas, Universidad Aut\u00f3noma de Nuevo Le\u00f3n, Av. Universidad S\/N, Ciudad Universitaria, San Nicol\u00e1s de los Garza CP 66451, Nuevo Le\u00f3n,Mexico"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Elizabeth","family":"Elizondo-Trevi\u00f1o","sequence":"additional","affiliation":[{"name":"Facultad de Ciencias Qu\u00edmicas, Universidad Aut\u00f3noma de Nuevo Le\u00f3n, Av. Universidad S\/N, Ciudad Universitaria, San Nicol\u00e1s de los Garza CP 66451, Nuevo Le\u00f3n,Mexico"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Elvira","family":"Garza-Gonz\u00e1lez","sequence":"additional","affiliation":[{"name":"Facultad de Medicina, Universidad Aut\u00f3noma de Nuevo Le\u00f3n, Madero y Aguirre Peque\u00f1o, Mitras Centro, Monterrey CP 64460, Nuevo Le\u00f3n, Mexico"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Laura","family":"Alvarez","sequence":"additional","affiliation":[{"name":"Centro de Investigaciones Qu\u00edmicas, Universidad Aut\u00f3noma del Estado de Morelos, Av. Universidad 1001, Chamilpa, Cuernavaca CP 62209, Morelos, Mexico"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Mar\u00eda","family":"Del Rayo Camacho-Corona","sequence":"additional","affiliation":[{"name":"Facultad de Ciencias Qu\u00edmicas, Universidad Aut\u00f3noma de Nuevo Le\u00f3n, Av. Universidad S\/N, Ciudad Universitaria, San Nicol\u00e1s de los Garza CP 66451, Nuevo Le\u00f3n,Mexico"}],"role":[{"vocabulary":"crossref","role":"author"}]}],"member":"1968","published-online":{"date-parts":[[2012,9,19]]},"reference":[{"key":"ref_1","unstructured":"Available online:http:\/\/www.who.int\/tb\/publications\/2011\/factsheet_tb_2011.pdf."},{"key":"ref_2","doi-asserted-by":"crossref","first-page":"93","DOI":"10.1002\/med.20017","article-title":"Fighting tuberculosis: An old disease with new challenges","volume":"25","author":"Tripathi","year":"2005","journal-title":"Med. Res. Rev."},{"key":"ref_3","doi-asserted-by":"crossref","first-page":"535","DOI":"10.1039\/b212154a","article-title":"Antimycobacterial natural products","volume":"20","author":"Copp","year":"2003","journal-title":"Nat. Prod. 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