{"status":"ok","message-type":"work","message-version":"1.0.0","message":{"indexed":{"date-parts":[[2026,7,30]],"date-time":"2026-07-30T16:52:29Z","timestamp":1785430349014,"version":"3.56.0"},"reference-count":44,"publisher":"MDPI AG","issue":"12","license":[{"start":{"date-parts":[[2026,6,16]],"date-time":"2026-06-16T00:00:00Z","timestamp":1781568000000},"content-version":"vor","delay-in-days":0,"URL":"https:\/\/creativecommons.org\/licenses\/by\/4.0\/"}],"funder":[{"DOI":"10.13039\/100008989","name":"Universidad Aut\u00f3noma de Quer\u00e9taro","doi-asserted-by":"publisher","award":["FQU202418"],"award-info":[{"award-number":["FQU202418"]}],"id":[{"id":"10.13039\/100008989","id-type":"DOI","asserted-by":"publisher"}]},{"award":["FQU202418"],"award-info":[{"award-number":["FQU202418"]}],"id":[{"id":"https:\/\/ror.org\/00v8fdc16","id-type":"ROR","asserted-by":"publisher"}]}],"content-domain":{"domain":[],"crossmark-restriction":false},"short-container-title":["Molecules"],"abstract":"<jats:p>Heliopsis longipes, commonly known as chilcuague, is a Mexican medicinal plant recognized for its diverse biological activities, largely attributed to its alkamide content, particularly affinin. However, metabolic variations associated with plant development remain poorly understood. This study evaluated the influence of phenological stage on the phytochemical profile and vasodilatory activity of H. longipes roots. Dichloromethane root extracts from plants at different developmental stages were analyzed using metabolomics based on 1H NMR spectroscopy, complemented by GC\u2013MS profiling. Major alkamides were isolated and structurally characterized as analytical standards. Notably, three alkamides, N-isobutylundeca-2(E)-en-8,10-diynamide, N-isobutylundeca-3(E)-en-8,10-diynamide, and N-isobutyl-2(E),4(Z)-undecadiene-8,10-diynamide, are reported for the first time in H. longipes roots. Multivariate analyses (PCA and OPLS-DA) revealed significant stage-dependent metabolic variation, particularly in affinin. The lack of correlation between valine decarboxylase activity and affinin levels suggests additional regulatory steps in its biosynthesis. Vasodilatory activity increased during development, reaching maximum effect during fructification and defoliation stages, with no significant differences between them. These findings highlight the impact of phenological stage on alkamide production and bioactivity, providing a basis for optimizing cultivation and harvest timing.<\/jats:p>","DOI":"10.3390\/molecules31122114","type":"journal-article","created":{"date-parts":[[2026,6,16]],"date-time":"2026-06-16T05:46:28Z","timestamp":1781588788000},"page":"2114","update-policy":"https:\/\/doi.org\/10.3390\/mdpi_crossmark_policy","source":"Crossref","is-referenced-by-count":0,"title":["Metabolomic Analysis of Heliopsis longipes Roots Across Phenological Stages"],"prefix":"10.3390","volume":"31","author":[{"ORCID":"https:\/\/orcid.org\/0000-0003-4967-2927","authenticated-orcid":false,"given":"Victoria","family":"Ruiz-Castillo","sequence":"first","affiliation":[{"name":"Posgrado en Ciencias Qu\u00edmico Biol\u00f3gicas, Facultad de Qu\u00edmica, Universidad Aut\u00f3noma de Quer\u00e9taro, Cerro de las Campanas S\/N, Santiago de Quer\u00e9taro C.P. 76010, Quer\u00e9taro, Mexico"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"ORCID":"https:\/\/orcid.org\/0000-0002-5748-7097","authenticated-orcid":false,"given":"Ram\u00f3n Gerardo","family":"Guevara-Gonz\u00e1lez","sequence":"additional","affiliation":[{"name":"Grupo de Ingenier\u00eda de Biosistemas, Facultad de Ingenier\u00eda, Universidad Aut\u00f3noma de Quer\u00e9taro, Campus Amazcala. Carr. Chichimequillas-Amazcala Km 1 2\/N, Amazcala, El M\u00e1rques C.P. 76265, Quer\u00e9taro, Mexico"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"ORCID":"https:\/\/orcid.org\/0000-0002-3711-6491","authenticated-orcid":false,"given":"C\u00e9sar","family":"Ibarra-Alvarado","sequence":"additional","affiliation":[{"name":"Laboratorio de Investigaci\u00f3n Qu\u00edmica y Farmacol\u00f3gica de Productos Naturales, Facultad de Qu\u00edmica, Universidad Aut\u00f3noma de Quer\u00e9taro, Cerro de las Campanas S\/N, Santiago de Quer\u00e9taro C.P. 76010, Quer\u00e9taro, Mexico"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Pedro Alberto","family":"V\u00e1zquez-Landaverde","sequence":"additional","affiliation":[{"name":"Centro de Investigaci\u00f3n en Ciencia Aplicada y Tecnol\u00f3gica Avanzada del Instituto Polit\u00e9cnico Nacional, Unidad Quer\u00e9taro, Cerro Blanco 141, Colinas del Cimatario, Santiago de Quer\u00e9taro C.P. 76090, Quer\u00e9taro, Mexico"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"ORCID":"https:\/\/orcid.org\/0000-0001-6465-9363","authenticated-orcid":false,"given":"Eduardo Rodr\u00edguez de San","family":"Miguel","sequence":"additional","affiliation":[{"name":"Departamento de Qu\u00edmica Anal\u00edtica, Facultad de Qu\u00edmica, Universidad Nacional Aut\u00f3noma de M\u00e9xico, Circuito Escolar S\/N, Ciudad Universitaria, Coyoac\u00e1n, Ciudad de M\u00e9xico C.P. 04510, Mexico"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"ORCID":"https:\/\/orcid.org\/0000-0003-2813-8776","authenticated-orcid":false,"given":"Pablo","family":"Aguilar-Rodr\u00edguez","sequence":"additional","affiliation":[{"name":"Laboratorio Universitario de Resonancia Magn\u00e9tica Nuclear, Instituto de Qu\u00edmica, Universidad Nacional Aut\u00f3noma de M\u00e9xico, Circuito Exterior S\/N, Ciudad Universitaria, Coyoac\u00e1n, Ciudad de M\u00e9xico C.P. 04510, Mexico"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"ORCID":"https:\/\/orcid.org\/0000-0002-9517-1763","authenticated-orcid":false,"given":"Martha Elena","family":"Garc\u00eda-Aguilera","sequence":"additional","affiliation":[{"name":"Laboratorio Universitario de Resonancia Magn\u00e9tica Nuclear, Instituto de Qu\u00edmica, Universidad Nacional Aut\u00f3noma de M\u00e9xico, Circuito Exterior S\/N, Ciudad Universitaria, Coyoac\u00e1n, Ciudad de M\u00e9xico C.P. 04510, Mexico"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"ORCID":"https:\/\/orcid.org\/0000-0002-0915-5346","authenticated-orcid":false,"given":"Nuria","family":"Esturau-Escofet","sequence":"additional","affiliation":[{"name":"Laboratorio Universitario de Resonancia Magn\u00e9tica Nuclear, Instituto de Qu\u00edmica, Universidad Nacional Aut\u00f3noma de M\u00e9xico, Circuito Exterior S\/N, Ciudad Universitaria, Coyoac\u00e1n, Ciudad de M\u00e9xico C.P. 04510, Mexico"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"ORCID":"https:\/\/orcid.org\/0000-0001-6131-9013","authenticated-orcid":false,"given":"Alejandra","family":"Rojas-Molina","sequence":"additional","affiliation":[{"name":"Laboratorio de Investigaci\u00f3n Qu\u00edmica y Farmacol\u00f3gica de Productos Naturales, Facultad de Qu\u00edmica, Universidad Aut\u00f3noma de Quer\u00e9taro, Cerro de las Campanas S\/N, Santiago de Quer\u00e9taro C.P. 76010, Quer\u00e9taro, Mexico"}],"role":[{"vocabulary":"crossref","role":"author"}]}],"member":"1968","published-online":{"date-parts":[[2026,6,16]]},"reference":[{"key":"ref_1","first-page":"115","article-title":"The genus Heliopsis (Heliantheaae; Asteraceae) in Mexico and the alkamides stored in its roots","volume":"65","year":"2004","journal-title":"Acta Bot. 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