Alkamide Content and Localization in <i>Heliopsis longipes</i> Cypselae, Obtained via Fluorescence and Double-Multiphoton Microscopy

The alkamide content and specific tissue localization in the cypselae of <i>Heliopsis longipes</i> were investigated using gas chromatography–electron ionization mass spectrometry (GC-EIMS) and multiphoton fluorescence microscopy (MPFM). GC-EIMS analysis identified two olefinic alkamides...

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Main Authors: Juan Vázquez-Martínez, Jorge Molina-Torres
Format: Article
Language:English
Published: MDPI AG 2024-11-01
Series:Molecules
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Online Access:https://www.mdpi.com/1420-3049/29/23/5651
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author Juan Vázquez-Martínez
Jorge Molina-Torres
author_facet Juan Vázquez-Martínez
Jorge Molina-Torres
author_sort Juan Vázquez-Martínez
collection DOAJ
description The alkamide content and specific tissue localization in the cypselae of <i>Heliopsis longipes</i> were investigated using gas chromatography–electron ionization mass spectrometry (GC-EIMS) and multiphoton fluorescence microscopy (MPFM). GC-EIMS analysis identified two olefinic alkamides: affinin (spilanthol) and <i>N</i>-2-methylbutyl-2<i>E</i>,6<i>Z</i>,8<i>E</i>-decatrienamide. Microscopic analysis revealed that alkamides are localized within the cotyledons, and specifically compartmentalized in lipid bodies, highlighting their spatial organization. The linear unmixing of fluorescence emission fingerprints showed that affinin exhibits autofluorescence at 693 nm, corresponding to the red spectral region. This emission is attributed to the conjugated double bonds in its acyl chain. This study is the first to report on the presence and precise localization of alkamides in the cypselae of <i>H. longipes.</i>
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spelling doaj-art-8bca3683ec544d98a42eb7f84a3f9cc72024-12-13T16:28:35ZengMDPI AGMolecules1420-30492024-11-012923565110.3390/molecules29235651Alkamide Content and Localization in <i>Heliopsis longipes</i> Cypselae, Obtained via Fluorescence and Double-Multiphoton MicroscopyJuan Vázquez-Martínez0Jorge Molina-Torres1Departamento de Ingeniería Química, TecNM/ITS Irapuato, Silao-Irapuato Km 12.5 El Copal, Irapuato CP 36821, GTO, MexicoDepartamento de Biotecnología y Bioquímica, Cinvestav Irapuato, Km. 9.6 Libramiento Norte Carretera Irapuato-León, Irapuato CP 36821, GTO, MexicoThe alkamide content and specific tissue localization in the cypselae of <i>Heliopsis longipes</i> were investigated using gas chromatography–electron ionization mass spectrometry (GC-EIMS) and multiphoton fluorescence microscopy (MPFM). GC-EIMS analysis identified two olefinic alkamides: affinin (spilanthol) and <i>N</i>-2-methylbutyl-2<i>E</i>,6<i>Z</i>,8<i>E</i>-decatrienamide. Microscopic analysis revealed that alkamides are localized within the cotyledons, and specifically compartmentalized in lipid bodies, highlighting their spatial organization. The linear unmixing of fluorescence emission fingerprints showed that affinin exhibits autofluorescence at 693 nm, corresponding to the red spectral region. This emission is attributed to the conjugated double bonds in its acyl chain. This study is the first to report on the presence and precise localization of alkamides in the cypselae of <i>H. longipes.</i>https://www.mdpi.com/1420-3049/29/23/5651affininalkamidesGC-EIMS<i>Heliopsis longipes</i> seedsmultiphoton microscopyspilanthol
spellingShingle Juan Vázquez-Martínez
Jorge Molina-Torres
Alkamide Content and Localization in <i>Heliopsis longipes</i> Cypselae, Obtained via Fluorescence and Double-Multiphoton Microscopy
Molecules
affinin
alkamides
GC-EIMS
<i>Heliopsis longipes</i> seeds
multiphoton microscopy
spilanthol
title Alkamide Content and Localization in <i>Heliopsis longipes</i> Cypselae, Obtained via Fluorescence and Double-Multiphoton Microscopy
title_full Alkamide Content and Localization in <i>Heliopsis longipes</i> Cypselae, Obtained via Fluorescence and Double-Multiphoton Microscopy
title_fullStr Alkamide Content and Localization in <i>Heliopsis longipes</i> Cypselae, Obtained via Fluorescence and Double-Multiphoton Microscopy
title_full_unstemmed Alkamide Content and Localization in <i>Heliopsis longipes</i> Cypselae, Obtained via Fluorescence and Double-Multiphoton Microscopy
title_short Alkamide Content and Localization in <i>Heliopsis longipes</i> Cypselae, Obtained via Fluorescence and Double-Multiphoton Microscopy
title_sort alkamide content and localization in i heliopsis longipes i cypselae obtained via fluorescence and double multiphoton microscopy
topic affinin
alkamides
GC-EIMS
<i>Heliopsis longipes</i> seeds
multiphoton microscopy
spilanthol
url https://www.mdpi.com/1420-3049/29/23/5651
work_keys_str_mv AT juanvazquezmartinez alkamidecontentandlocalizationiniheliopsislongipesicypselaeobtainedviafluorescenceanddoublemultiphotonmicroscopy
AT jorgemolinatorres alkamidecontentandlocalizationiniheliopsislongipesicypselaeobtainedviafluorescenceanddoublemultiphotonmicroscopy