Profiling of Alkaloids and Eremophilanes in Miracle Tea (<i>Packera candidissima</i> and <i>P. bellidifolia</i>) Products

Commercial preparations of the Mexican herbal drug known as “miracle tea” (<i>Packera candidissima</i> and <i>P. bellidifolia</i>) have been profiled qualitatively by HPLC and GC-MS. Eremophilanes (<b>3</b>–<b>7</b>) were the major components found in the hexane-soluble fraction, while pyrrolizidine alkaloids (PAs) were identified in the alkaloid extracts. The content of free PAs and their N-oxides was determined for a total of 22 samples, and the results showed that the amount of these hepatotoxic compounds (0.0005–0.94% free PAs; 0.0004–0.55% N-oxides), through the presence of retrorsine (<b>1</b>) and senesionine (<b>2</b>) as the main constituents, may reach toxic levels. Hexane-soluble extracts from commercial presentations (dried whole plants) of both species afforded neoadenostylone (<b>3</b>), 6-(2-methylbutanoyloxy)-9-oxo-1-(10)-furanoeremophilene (<b>4</b>), and epineoadenostylone (<b>5</b>), in addition to methyl-4-hydroxyphenylacetate (<b>8</b>) and methyl-2-(1-hydroxy-4-oxocyclohexyl)­acetate (<b>9</b>). Also, epicacalone (<b>6</b>) and the new compound 2β-hydroxyneoadenostylone (<b>7</b>) were isolated from <i>P. bellidifolia</i>.