{"status":"ok","message-type":"work","message-version":"1.0.0","message":{"indexed":{"date-parts":[[2026,1,11]],"date-time":"2026-01-11T14:17:35Z","timestamp":1768141055995,"version":"3.49.0"},"reference-count":21,"publisher":"MDPI AG","issue":"1","license":[{"start":{"date-parts":[[2014,12,23]],"date-time":"2014-12-23T00:00:00Z","timestamp":1419292800000},"content-version":"vor","delay-in-days":0,"URL":"https:\/\/creativecommons.org\/licenses\/by\/4.0\/"}],"funder":[{"name":"FUNDECT-MS","award":["0082-07"],"award-info":[{"award-number":["0082-07"]}]}],"content-domain":{"domain":[],"crossmark-restriction":false},"short-container-title":["Molecules"],"abstract":"<jats:p>Chemical investigation of Guarea kunthiana fruits, guided by their  effect on the reproductive cycle of engorged females of the cattle tick  Rhipicephalus (Boophilus) microplus\u2014a major economic problem to the livestock industry worldwide\u2014led to isolation of 3\u03b2-O-tigloylmelianol, a new protolimonoid, from the bioactive hexane phase obtained by partitioning the crude ethanol extract. An adult immersion test was performed. The compound strongly inhibited egg-laying and hatchability (99.2% effectiveness at a 0.01% concentration). Melianone, isolated from the same phase, yielded unremarkable results in the adult immersion test. From the dichloromethane phase, melianol, melianodiol, meliantriol, and a new protolimonoid,  3\u03b2-O-tigloylmeliantriol, were isolated, all of which, in the same manner as melianone, exhibited unremarkable results in the test. The structures of new and known compounds were mostly established by 1D- and 2D-NMR analyses and mass spectrometry data. This is the first report on the bioactivity of protolimonoids on the reproductive cycle of engorged females of R. (B.) microplus. 3\u03b2-O-Tigloylmelianol proved a promising candidate for the development of a biocontrol agent against the cattle tick investigated, as an alternative to environmentally hazardous synthetic acaricides.<\/jats:p>","DOI":"10.3390\/molecules20010111","type":"journal-article","created":{"date-parts":[[2014,12,23]],"date-time":"2014-12-23T15:33:56Z","timestamp":1419348836000},"page":"111-126","update-policy":"https:\/\/doi.org\/10.3390\/mdpi_crossmark_policy","source":"Crossref","is-referenced-by-count":10,"title":["3\u03b2-O-Tigloylmelianol from Guarea kunthiana: A New Potential Agent to Control Rhipicephalus (Boophilus) microplus, a Cattle Tick of Veterinary Significance"],"prefix":"10.3390","volume":"20","author":[{"given":"Carlos","family":"Miguita","sequence":"first","affiliation":[{"name":"Laborat\u00f3rio de Pesquisa de Produtos Naturais Bioativos, Instituto de Qu\u00edmica,  Universidade Federal de Mato Grosso do Sul, 79074-460 Campo Grande, MS, Brazil"}],"role":[{"role":"author","vocabulary":"crossref"}]},{"given":"Carolina","family":"Barbosa","sequence":"additional","affiliation":[{"name":"Laborat\u00f3rio de Parasitologia Animal, Universidade Estadual de Mato Grosso do Sul,  79200-000 Aquidauana, MS, Brazil"}],"role":[{"role":"author","vocabulary":"crossref"}]},{"given":"Lidilhone","family":"Hamerski","sequence":"additional","affiliation":[{"name":"Laborat\u00f3rio de Pesquisa de Produtos Naturais Bioativos, Instituto de Qu\u00edmica,  Universidade Federal de Mato Grosso do Sul, 79074-460 Campo Grande, MS, Brazil"},{"name":"Instituto de Pesquisas de Produtos Naturais, Universidade Federal do Rio de Janeiro,  21941-902 Rio de Janeiro, RJ, Brazil"}],"role":[{"role":"author","vocabulary":"crossref"}]},{"given":"Ulana","family":"Sarmento","sequence":"additional","affiliation":[{"name":"Laborat\u00f3rio de Pesquisa de Produtos Naturais Bioativos, Instituto de Qu\u00edmica,  Universidade Federal de Mato Grosso do Sul, 79074-460 Campo Grande, MS, Brazil"}],"role":[{"role":"author","vocabulary":"crossref"}]},{"given":"Jos\u00e9","family":"Nascimento","sequence":"additional","affiliation":[{"name":"Laborat\u00f3rio de Insetos Frug\u00edforos, Faculdade de Ci\u00eancias Biol\u00f3gicas e Ambientais,  Universidade Federal da Grande Dourados, 79804-970 Dourados, MS, Brazil"}],"role":[{"role":"author","vocabulary":"crossref"}]},{"given":"Walmir","family":"Garcez","sequence":"additional","affiliation":[{"name":"Laborat\u00f3rio de Pesquisa de Produtos Naturais Bioativos, Instituto de Qu\u00edmica,  Universidade Federal de Mato Grosso do Sul, 79074-460 Campo Grande, MS, Brazil"}],"role":[{"role":"author","vocabulary":"crossref"}]},{"given":"Fernanda","family":"Garcez","sequence":"additional","affiliation":[{"name":"Laborat\u00f3rio de Pesquisa de Produtos Naturais Bioativos, Instituto de Qu\u00edmica,  Universidade Federal de Mato Grosso do Sul, 79074-460 Campo Grande, MS, Brazil"}],"role":[{"role":"author","vocabulary":"crossref"}]}],"member":"1968","published-online":{"date-parts":[[2014,12,23]]},"reference":[{"key":"ref_1","doi-asserted-by":"crossref","first-page":"109","DOI":"10.1016\/0304-4017(94)03115-D","article-title":"Epidemiology of babesiosis and anaplasmosis in South and Central America","volume":"57","author":"Guglielmone","year":"1995","journal-title":"Vet. 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