<?xml version="1.0" encoding="ISO-8859-1"?><article xmlns:mml="http://www.w3.org/1998/Math/MathML" xmlns:xlink="http://www.w3.org/1999/xlink" xmlns:xsi="http://www.w3.org/2001/XMLSchema-instance">
<front>
<journal-meta>
<journal-id>1870-249X</journal-id>
<journal-title><![CDATA[Journal of the Mexican Chemical Society]]></journal-title>
<abbrev-journal-title><![CDATA[J. Mex. Chem. Soc]]></abbrev-journal-title>
<issn>1870-249X</issn>
<publisher>
<publisher-name><![CDATA[Sociedad Química de México A.C.]]></publisher-name>
</publisher>
</journal-meta>
<article-meta>
<article-id>S1870-249X2017000100067</article-id>
<title-group>
<article-title xml:lang="en"><![CDATA[Tonantzitlolone A and other cytotoxic constituents of Sapium macrocarpum (Euphorbiaceae)]]></article-title>
</title-group>
<contrib-group>
<contrib contrib-type="author">
<name>
<surname><![CDATA[Novillo]]></surname>
<given-names><![CDATA[Fernando]]></given-names>
</name>
<xref ref-type="aff" rid="Aff"/>
<xref ref-type="aff" rid="Aaf"/>
</contrib>
<contrib contrib-type="author">
<name>
<surname><![CDATA[Rosero]]></surname>
<given-names><![CDATA[Verónica]]></given-names>
</name>
<xref ref-type="aff" rid="Aff"/>
<xref ref-type="aff" rid="Aaf"/>
</contrib>
<contrib contrib-type="author">
<name>
<surname><![CDATA[Chávez]]></surname>
<given-names><![CDATA[María Isabel]]></given-names>
</name>
<xref ref-type="aff" rid="Aff"/>
</contrib>
<contrib contrib-type="author">
<name>
<surname><![CDATA[Hernández-Ortega]]></surname>
<given-names><![CDATA[Simón]]></given-names>
</name>
<xref ref-type="aff" rid="Aff"/>
</contrib>
<contrib contrib-type="author">
<name>
<surname><![CDATA[Martínez]]></surname>
<given-names><![CDATA[Esteban M.]]></given-names>
</name>
<xref ref-type="aff" rid="Aff"/>
</contrib>
<contrib contrib-type="author">
<name>
<surname><![CDATA[Delgado]]></surname>
<given-names><![CDATA[Guillermo]]></given-names>
</name>
<xref ref-type="aff" rid="Aff"/>
</contrib>
</contrib-group>
<aff id="Af1">
<institution><![CDATA[,Universidad Nacional Autónoma de México Instituto de Química ]]></institution>
<addr-line><![CDATA[Ciudad de México ]]></addr-line>
<country>Mexico</country>
</aff>
<aff id="Af2">
<institution><![CDATA[,Universidad Central del Ecuador Facultad de Ciencias Químicas ]]></institution>
<addr-line><![CDATA[Francisco Viteri Quito]]></addr-line>
<country>Ecuador</country>
</aff>
<aff id="Af3">
<institution><![CDATA[,Universidad Nacional Autónoma de México Instituto de Biología ]]></institution>
<addr-line><![CDATA[Ciudad de México ]]></addr-line>
<country>Mexico</country>
</aff>
<pub-date pub-type="pub">
<day>00</day>
<month>03</month>
<year>2017</year>
</pub-date>
<pub-date pub-type="epub">
<day>00</day>
<month>03</month>
<year>2017</year>
</pub-date>
<volume>61</volume>
<numero>1</numero>
<fpage>67</fpage>
<lpage>73</lpage>
<copyright-statement/>
<copyright-year/>
<self-uri xlink:href="http://www.scielo.org.mx/scielo.php?script=sci_arttext&amp;pid=S1870-249X2017000100067&amp;lng=en&amp;nrm=iso"></self-uri><self-uri xlink:href="http://www.scielo.org.mx/scielo.php?script=sci_abstract&amp;pid=S1870-249X2017000100067&amp;lng=en&amp;nrm=iso"></self-uri><self-uri xlink:href="http://www.scielo.org.mx/scielo.php?script=sci_pdf&amp;pid=S1870-249X2017000100067&amp;lng=en&amp;nrm=iso"></self-uri><abstract abstract-type="short" xml:lang="en"><p><![CDATA[Abstract:  Sapium macrocarpum (Euphorbiaceae) is a tropical tree located mainly in the southern part of Mexico and in Central America, and it is used in the Mayan traditional medicine for the treatment of several skin diseases. The dichloromethane-MeOH extract of the aerial parts displayed cytotoxic activity against certain cancer cell lines. Lupeol (1), lupenone (2), sitostenone (3), &#946;-sitosterol (4), stigmasterol (5), sitosteryl &#946;-D-glucopyranoside (6) and the rare diterpene tonantzi tlolone A (7) were characterized from this extract. The structural analysis allowed the 1H NMR reassignments for H-12&#945; and H-12&#946;, and for H-13&#945; and H-13&#946; of tonantzitlolone A (7). The cytotoxic activity of compounds 1-3, 6 and 7 was evaluated against selected cancer cell lines. Compounds 3, 6 and 7 displayed clear activity against K562 (leukemia). This is the first report on the chemical constituents of S. macrocarpum, and points out that this species is an additional source of tonantzitlolone A. Compound 7 has only been reported previously from species of the Stillingia, Sebastiania and Sapium genera, which belong to the Hippomaninae subtribe of the family Euphorbiaceae.]]></p></abstract>
<abstract abstract-type="short" xml:lang="es"><p><![CDATA[Resumen: Sapium macrocarpum (familia Euphorbiaceae) es un árbol localizado en la parte central de México y en Sudamérica, el cual es usado en la medicina tradicional Maya para el tratamiento de diversas enfermedades de la piel. El extracto de diclorometano-metanol de las partes aéreas de esta especie mostró actividad inhibitoria de la proliferación de ciertas células cancerosas humanas. Lupeol (1), lupenona (2), sitostenona (3), &#946;-sitosterol (4), estigmasterol (5), &#946;-D-glucopiranósido de sitosterilo (6) y el diterpeno relativamente raro tonantzitlolona A (7) fueron caracterizados de este extracto. El análisis estructural de la tonantzitlolona A (7) permitió la reasignación de las señales de RMN 1H de H-12&#945; y H-12&#946;, y de H-13&#945; y H-13&#946;. La actividad citotóxica de los compuestos 1-3, 6 y 7 fue evaluada frente a las líneas celulares cancerosas selectas. Los compuestos 3, 6 y 7 mostraron actividad clara contra K562 (leucemia). Este es el primer reporte sobre los constituyentes químicos de S. macrocarpum, encontrando que esta especie constituye una fuente adicional de tonantzitlolona A. El compuesto 7 ha sido aislado de los géneros Stillingia, Sebastiania y Sapium, los cuales pertenecen a la subtribu Hippomaninae de la familia Euphorbiaceae.]]></p></abstract>
<kwd-group>
<kwd lng="es"><![CDATA[sitostenona]]></kwd>
<kwd lng="es"><![CDATA[diterpenos]]></kwd>
<kwd lng="es"><![CDATA[flexibilano]]></kwd>
<kwd lng="es"><![CDATA[Euphorbiaceae]]></kwd>
<kwd lng="es"><![CDATA[reasignaciones de RMN, citotoxicidad]]></kwd>
<kwd lng="en"><![CDATA[sitostenone]]></kwd>
<kwd lng="en"><![CDATA[diterpenes]]></kwd>
<kwd lng="en"><![CDATA[flexibilane]]></kwd>
<kwd lng="en"><![CDATA[Euphorbiaceae]]></kwd>
<kwd lng="en"><![CDATA[NMR reassignments, cytotoxicity]]></kwd>
</kwd-group>
</article-meta>
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