AUTHOR=Ferreira Queiroz Marcos Marçal , Huber Robin , Marcourt Laurence , Guénée Laure , Allard Pierre-Marie , Rutz Adriano , Nothias Louis-Félix , Carlotta De Ruvo Concetta , Kissling Jonathan , Gupta Mahabir Prashad , Ferreira Queiroz Emerson , Wolfender Jean-Luc 

TITLE=Phytochemical study of Alzatea verticillata, the sole species belonging to the Alzateaceae family

JOURNAL=Frontiers in Natural Products

VOLUME=2

YEAR=2023

URL=https://www.frontiersin.org/journals/natural-products/articles/10.3389/fntpr.2023.1147195

DOI=10.3389/fntpr.2023.1147195

ISSN=2813-2602

ABSTRACT=<p><italic>Alzatea verticillata</italic> Ruiz &amp; Pav. (Alzateaceae) is a tropical tree from Central and South America. It is the only living species of <italic>Alzatea</italic> genus and the Alzateaceae family, all others being extinct. With the aim to investigate the possibility to find unusual natural products, the chemical content of the dichloromethane and methanolic extracts (stems and leaves) of <italic>A. verticillata</italic> have been investigated. Apolar and polar extracts were purified by semi-preparative HPLC using appropriate stationary phase columns allowing the isolation of 12 compounds: walterolactone B (<bold>2</bold>) walterolactone A/B <italic>β</italic>-<italic>D</italic>-pyranoglucoside (<bold>3</bold>), gallic acid (<bold>4</bold>), caffeic acid 4-<italic>O</italic>-<italic>β</italic>-D-glucopyranoside (<bold>6</bold>), walterolactone A/B 6-<italic>O</italic>-gallate-<italic>β</italic>-D-glucopyranoside (<bold>8</bold>), caffeic acid (<bold>9</bold>), 8-desmethylsideroxylin (<bold>11</bold>), sideroxylin (<bold>12</bold>) and 7,7′-bis(3,4-dihydroxyphenyl)-8,8′-cyclobutanedicarboxylic acid (<bold>7</bold>). Three isolated compounds are natural products described here for the first time: dimethyl-anemonin (<bold>1</bold>) and two <italic>β</italic>-truxinic acid derivatives (<italic>rel</italic>-(7<italic>S</italic>, 8<italic>R</italic>, 7′<italic>R</italic>, 8′<italic>S</italic>)-7,7′-bis(4-glucosyloxy-3-hydroxyphenyl)-8,8′-cyclobutane dicarboxylic acid (<bold>5</bold>) and <italic>rel</italic>-(7<italic>S</italic>, 8<italic>R</italic>, 7′<italic>R</italic>, 8′<italic>S</italic>)-7,7′-bis(4-glucosyloxy-3-hydroxyphenyl)-8,8′-cyclobutane-9-methyl dicarboxylic acid (<bold>10</bold>). The structures of the isolated compounds were elucidated by NMR and HRMS. The structure of compound <bold>1</bold> was confirmed by X-ray crystallography. A MS-based metabolite analysis of the <italic>A. verticillata</italic> extracts revealed additional truxinic acid derivatives that were putatively annotated with the help of feature-based molecular network. The presence of phenolic compounds such as truxinic acid derivatives could explain the traditional use of this plant as these compounds are known to possess anti-inflammatory and anti-nociceptive properties.</p>