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The aim of this work was to study the\n in vitro<\/jats:italic>\n inhibition of hemozoin formation, inhibition of isoprenoid biosynthesis in\n Plasmodium falciparum<\/jats:named-content>\n cultures, and\n in vivo<\/jats:italic>\n antimalarial activity of several 4-nerolidylcatechol derivatives. 1,2-\n O<\/jats:italic>\n ,\n O<\/jats:italic>\n -Diacetyl-4-nerolidylcatechol (\n 2<\/jats:bold>\n ) inhibited\n in vitro<\/jats:italic>\n hemozoin formation by up to 50%. In metabolic labeling studies using [1-(\n n<\/jats:italic>\n )-\n 3<\/jats:sup>\n H]geranylgeranyl pyrophosphate, diester\n 2<\/jats:bold>\n significantly inhibited the biosynthesis of isoprenoid metabolites ubiquinone\n 8<\/jats:bold>\n , menaquinone\n 4<\/jats:bold>\n , and dolichol\n 12<\/jats:bold>\n in cultures of\n P. falciparum<\/jats:named-content>\n 3D7. Similarly, 2-\n O<\/jats:italic>\n -benzyl-4-nerolidylcatechol (\n 3<\/jats:bold>\n ) significantly inhibited the biosynthesis of dolichol\n 12<\/jats:bold>\n .\n P. falciparum<\/jats:named-content>\n in vitro<\/jats:italic>\n protein synthesis was not affected by compounds\n 2<\/jats:bold>\n or\n 3<\/jats:bold>\n . At oral doses of 50 mg per kg of body weight per day, compound\n 2<\/jats:bold>\n suppressed\n Plasmodium berghei<\/jats:named-content>\n NK65 in infected BALB\/c mice by 44%. This\n in vivo<\/jats:italic>\n result for derivative\n 2<\/jats:bold>\n represents marked improvement over that obtained previously for natural product\n 1<\/jats:bold>\n . Compound\n 2<\/jats:bold>\n was not detected in mouse blood 1 h after oral ingestion or in mixtures with mouse blood\/blood plasma\n in vitro<\/jats:italic>\n . However, it was detected after\n in vitro<\/jats:italic>\n contact with human blood or blood plasma. Derivatives of 4-nerolidylcatechol exhibit parasite-specific modes of action, such as inhibition of isoprenoid biosynthesis and inhibition of hemozoin formation, and they therefore merit further investigation for their antimalarial potential.\n <\/jats:p>","DOI":"10.1128\/aac.05012-14","type":"journal-article","created":{"date-parts":[[2015,3,24]],"date-time":"2015-03-24T02:32:47Z","timestamp":1427164367000},"page":"3271-3280","update-policy":"https:\/\/doi.org\/10.1128\/asmj-crossmark-policy-page","source":"Crossref","is-referenced-by-count":30,"title":["In Vivo<\/i>\n Antimalarial Activity and Mechanisms of Action of 4-Nerolidylcatechol Derivatives"],"prefix":"10.1128","volume":"59","author":[{"given":"Luiz Francisco","family":"Rocha e Silva","sequence":"first","affiliation":[{"name":"National Institute for Amazon Research, Manaus, Amazonas, Brazil"},{"name":"Federal University of Amazonas, Manaus, Amazonas, Brazil"},{"name":"Center North University, Manaus, Amazonas, Brazil"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Karla Lagos","family":"Nogueira","sequence":"additional","affiliation":[{"name":"National Institute for Amazon Research, Manaus, Amazonas, Brazil"},{"name":"Federal University of Amazonas, Manaus, Amazonas, Brazil"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Ana Cristina da Silva","family":"Pinto","sequence":"additional","affiliation":[{"name":"National Institute for Amazon Research, Manaus, Amazonas, Brazil"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Alejandro Miguel","family":"Katzin","sequence":"additional","affiliation":[{"name":"Department of Parasitology, Institute of Biomedical Science, University of S\u00e3o Paulo, S\u00e3o Paulo, S\u00e3o Paulo, Brazil"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Rodrigo A. 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