Withanolides with Phytotoxic Activity from Two Species of the Genus <i>Salpichroa</i>: <i>S. origanifolia</i> and <i>S. tristis</i> var. <i>lehmannii</i>

Seven new withanolides, salpichrolides O–U (<b>1</b>–<b>7</b>), the known 2,3-dihydrosalpichrolide B (<b>9</b>), a substance not previously isolated from a natural source, and three known compounds, salpichrolide D (<b>8</b>), salpichrolide A (<b>10</b>), and salpichrolide C (<b>11</b>), were isolated and characterized from the aerial parts of <i>Salpichroa origanifolia</i> and <i>S. tristis</i> var. <i>lehmannii</i>. Compounds <b>1</b>–<b>4</b> and <b>8</b> have an oxygenated D ring, while compounds <b>5</b>–<b>7</b> and <b>9</b>–<b>11</b> possess a six-membered aromatic D ring. The structures of the isolated compounds were identified by analysis of their spectroscopic data including NMR and MS. Withanolides <b>1</b>, <b>3</b>, <b>8</b>, <b>10</b>, and <b>11</b> exhibited selective radicle growth inhibition toward <i>Lactuca sativa</i> (lettuce) at 150 and 400 ppm

β-Lapachone analogs with enhanced antiproliferative activity

In this study, we describe the synthesis of a series of α- and β-lapachone containing hydroxyl or methoxyl groups on the benzene ring, by means of the selective acid promoted cyclization of the appropriate lapachol analog. The evaluation of the antiproliferative activity in human solid tumor cell lines provided 7-hydroxy-β-lapachone as lead with enhanced activity over the parent drug β-lapachone. Cell cycle studies, protein expression experiments, and reactive oxygen species analysis revealed that, similarly to β-lapachone, ROS formation and DNA damage are critical factors in the cellular toxicity of 7-hydroxy-β-lapachone.Co-financed by the European Social Fund (FEDER), the Spanish Instituto de Salud Carlos III (PI11/00840), the Spanish MSC (RTICC RD06/0020/1046 and RD06/0020/0041), the Canary Islands ACIISI (PI 2007/021), the Canary Islands FUNCIS (PI 43/ 09), and by the Consejo Nacional de Investigaciones Científicas y Técnicas (CONICET PIP 0447), and Universidad de Buenos Aires (UBACyT 20020090200697). E.L.B. thanks CONICET for a fellowship. L.G.L. thanks ACIISI for a postdoctoral contract (SE- 10/19).Peer Reviewe

Withanolides with Phytotoxic Activity from Two Species of the Genus Salpichroa: S. origanifolia and S. tristis var. lehmannii

Seven new withanolides, salpichrolides O−U (1−7), the known 2,3-dihydrosalpichrolide B (9), a substance not previously isolated from a natural source, and three known compounds, salpichrolide D (8), salpichrolide A (10), and salpichrolide C (11), were isolated and characterized from the aerial parts of Salpichroa origanifolia and S. tristis var. lehmannii. Compounds 1−4 and 8 have an oxygenated D ring, while compounds 5−7 and 9−11 possess a six-membered aromatic D ring. The structures of the isolated compounds were identified by analysis of their spectroscopic data including NMR and MS. Withanolides 1, 3, 8, 10, and 11 exhibited selective radicle growth inhibition toward Lactuca sativa (lettuce) at 150 and 400 ppm.Fil: Nicotra, Viviana Estela. Consejo Nacional de Investigaciones Científicas y Técnicas. Centro Científico Tecnológico Conicet - Córdoba. Instituto Multidisciplinario de Biología Vegetal. Universidad Nacional de Córdoba. Facultad de Ciencias Exactas Físicas y Naturales. Instituto Multidisciplinario de Biología Vegetal; ArgentinaFil: Basso, Ana Valentina. Consejo Nacional de Investigaciones Científicas y Técnicas. Centro Científico Tecnológico Conicet - Córdoba. Instituto Multidisciplinario de Biología Vegetal. Universidad Nacional de Córdoba. Facultad de Ciencias Exactas Físicas y Naturales. Instituto Multidisciplinario de Biología Vegetal; ArgentinaFil: Ramacciotti, Natalia S.. Consejo Nacional de Investigaciones Científicas y Técnicas. Centro Científico Tecnológico Conicet - Córdoba. Instituto Multidisciplinario de Biología Vegetal. Universidad Nacional de Córdoba. Facultad de Ciencias Exactas Físicas y Naturales. Instituto Multidisciplinario de Biología Vegetal; ArgentinaFil: Misico, Rosana Isabel. Consejo Nacional de Investigaciones Científicas y Técnicas. Oficina de Coordinación Administrativa Ciudad Universitaria. Unidad de Microanálisis y Métodos Físicos en Química Orgánica. Universidad de Buenos Aires. Facultad de Ciencias Exactas y Naturales. Unidad de Microanálisis y Métodos Físicos en Química Orgánica; Argentin