{"id":305,"date":"2023-02-23T11:00:28","date_gmt":"2023-02-23T10:00:28","guid":{"rendered":"https:\/\/web.umons.ac.be\/smos\/?p=305"},"modified":"2023-09-01T11:41:44","modified_gmt":"2023-09-01T09:41:44","slug":"horse-chestnut-saponins-escins-isoescins-transescins-and-desacylescins","status":"publish","type":"post","link":"https:\/\/web.umons.ac.be\/smos\/2023\/02\/23\/horse-chestnut-saponins-escins-isoescins-transescins-and-desacylescins\/","title":{"rendered":"Horse Chestnut Saponins\u2013Escins, Isoescins, Transescins, and Desacylescins"},"content":{"rendered":"<figure id=\"attachment_306\" aria-describedby=\"caption-attachment-306\" style=\"width: 1974px\" class=\"wp-caption alignnone\"><img loading=\"lazy\" decoding=\"async\" class=\"size-full wp-image-306\" src=\"https:\/\/web.umons.ac.be\/app\/uploads\/sites\/80\/2023\/02\/2023-02-23.png\" alt=\"MALDI mass spectra (positive ionization mode) of three different saponin extracts: (a) Natural extract (NE); (b) Escins I, II and III enriched-extract (EE) obtained by flash chromatography separation (non-polar column\u2013acetonitrile gradient); (c) Microwave-assisted alkaline hydrolysis (pH 14\u2013150 \u00b0C\u20135 min) reaction extract (HE). The molecular structures are schematized by highlighting the targeted functions: in EE saponins, the esters are located on C21 (Tig or Ang) and C22 or C28 (Ac); in the HE saponins, the hydrolysis products possess alcohol groups on C21, C22, and C28. \" width=\"1974\" height=\"854\" srcset=\"https:\/\/web.umons.ac.be\/app\/uploads\/sites\/80\/2023\/02\/2023-02-23.png 1974w, https:\/\/web.umons.ac.be\/app\/uploads\/sites\/80\/2023\/02\/2023-02-23-300x130.png 300w, https:\/\/web.umons.ac.be\/app\/uploads\/sites\/80\/2023\/02\/2023-02-23-1024x443.png 1024w, https:\/\/web.umons.ac.be\/app\/uploads\/sites\/80\/2023\/02\/2023-02-23-768x332.png 768w, https:\/\/web.umons.ac.be\/app\/uploads\/sites\/80\/2023\/02\/2023-02-23-1536x665.png 1536w, https:\/\/web.umons.ac.be\/app\/uploads\/sites\/80\/2023\/02\/2023-02-23-1526x660.png 1526w, https:\/\/web.umons.ac.be\/app\/uploads\/sites\/80\/2023\/02\/2023-02-23-30x13.png 30w, https:\/\/web.umons.ac.be\/app\/uploads\/sites\/80\/2023\/02\/2023-02-23-60x26.png 60w, https:\/\/web.umons.ac.be\/app\/uploads\/sites\/80\/2023\/02\/2023-02-23-360x156.png 360w\" sizes=\"auto, (max-width: 1974px) 100vw, 1974px\" \/><figcaption id=\"caption-attachment-306\" class=\"wp-caption-text\">MALDI mass spectra (positive ionization mode) of three different saponin extracts: (a) Natural extract (NE); (b) Escins I, II and III enriched-extract (EE) obtained by flash chromatography separation (non-polar column\u2013acetonitrile gradient); (c) Microwave-assisted alkaline hydrolysis (pH 14\u2013150 \u00b0C\u20135 min) reaction extract (HE). The molecular structures are schematized by highlighting the targeted functions: in EE saponins, the esters are located on C21 (Tig or Ang) and C22 or C28 (Ac); in the HE saponins, the hydrolysis products possess alcohol groups on C21, C22, and C28.<\/figcaption><\/figure>\n<p>&nbsp;<\/p>\n<p>Escins constitute an abundant family of saponins (saponosides) and are the most active components in <em>Aesculum hippocastanum<\/em> (horse chestnut\u2014HC) seeds. They are of great pharmaceutical interest as a short-term treatment for venous insufficiency. Numerous escin congeners (slightly different compositions), as well as numerous regio-and stereo-isomers, are extractable from HC seeds, making quality control trials mandatory, especially since the structure\u2013activity relationship (SAR) of the escin molecules remains poorly described. In the present study, mass spectrometry, microwave activation, and hemolytic activity assays were used to characterize escin extracts (including a complete quantitative description of the escin congeners and isomers), modify the natural saponins (hydrolysis and transesterification) and measure their cytotoxicity (natural vs. modified escins). The aglycone ester groups characterizing the escin isomers were targeted. A complete quantitative analysis, isomer per isomer, of the weight content in the saponin extracts as well as in the seed dry powder is reported for the first time. An impressive 13% in weight of escins in the dry seeds was measured, confirming that the HC escins must be absolutely considered for high-added value applications, provided that their SAR is established. One of the objectives of this study was to contribute to this development by demonstrating that the aglycone ester functions are mandatory for the toxicity of the escin derivative, and that the cytotoxicity also depends on the relative position of the ester functions on the aglycone.<\/p>\n<p>&nbsp;<\/p>\n<p><a href=\"https:\/\/www.mdpi.com\/1420-3049\/28\/5\/2087\" target=\"_blank\" rel=\"noopener\">10.3390\/molecules28052087<\/a><\/p>\n","protected":false},"excerpt":{"rendered":"<p>Escins constitute an abundant family of saponins (saponosides) and are the most active components in Aesculum hippocastanum (horse chestnut\u2014HC) seeds. They are of great pharmaceutical interest as a short-term treatment for venous insufficiency. &#8230;<\/p>\n","protected":false},"author":157,"featured_media":306,"comment_status":"open","ping_status":"open","sticky":false,"template":"","format":"standard","meta":{"footnotes":""},"categories":[1],"tags":[],"class_list":["post-305","post","type-post","status-publish","format-standard","has-post-thumbnail","hentry","category-non-classe"],"yoast_head":"<!-- This site is optimized with the Yoast SEO plugin v25.1 - https:\/\/yoast.com\/wordpress\/plugins\/seo\/ -->\n<title>Horse Chestnut Saponins\u2013Escins, Isoescins, Transescins, and Desacylescins - Service \/ FS - Synth\u00e8se et Spectrom\u00e9trie de Masse Organiques<\/title>\n<meta name=\"robots\" content=\"index, follow, max-snippet:-1, max-image-preview:large, max-video-preview:-1\" \/>\n<link rel=\"canonical\" href=\"https:\/\/web.umons.ac.be\/smos\/2023\/02\/23\/horse-chestnut-saponins-escins-isoescins-transescins-and-desacylescins\/\" \/>\n<meta property=\"og:locale\" content=\"fr_FR\" \/>\n<meta property=\"og:type\" content=\"article\" \/>\n<meta property=\"og:title\" content=\"Horse Chestnut Saponins\u2013Escins, Isoescins, Transescins, and Desacylescins - Service \/ FS - Synth\u00e8se et Spectrom\u00e9trie de Masse Organiques\" \/>\n<meta property=\"og:description\" content=\"Escins constitute an abundant family of saponins (saponosides) and are the most active components in Aesculum hippocastanum (horse chestnut\u2014HC) seeds. They are of great pharmaceutical interest as a short-term treatment for venous insufficiency. ...\" \/>\n<meta property=\"og:url\" content=\"https:\/\/web.umons.ac.be\/smos\/2023\/02\/23\/horse-chestnut-saponins-escins-isoescins-transescins-and-desacylescins\/\" \/>\n<meta property=\"og:site_name\" content=\"Service \/ FS - Synth\u00e8se et Spectrom\u00e9trie de Masse Organiques\" \/>\n<meta property=\"article:published_time\" content=\"2023-02-23T10:00:28+00:00\" \/>\n<meta property=\"article:modified_time\" content=\"2023-09-01T09:41:44+00:00\" \/>\n<meta property=\"og:image\" content=\"https:\/\/web.umons.ac.be\/app\/uploads\/sites\/80\/2023\/02\/2023-02-23.png\" \/>\n\t<meta property=\"og:image:width\" content=\"1974\" \/>\n\t<meta property=\"og:image:height\" content=\"854\" \/>\n\t<meta property=\"og:image:type\" content=\"image\/png\" \/>\n<meta name=\"author\" content=\"Eric Weverbergh\" \/>\n<meta name=\"twitter:card\" content=\"summary_large_image\" \/>\n<meta name=\"twitter:label1\" content=\"\u00c9crit par\" \/>\n\t<meta name=\"twitter:data1\" content=\"Eric Weverbergh\" \/>\n\t<meta name=\"twitter:label2\" content=\"Dur\u00e9e de lecture estim\u00e9e\" \/>\n\t<meta name=\"twitter:data2\" content=\"2 minutes\" \/>\n<script type=\"application\/ld+json\" class=\"yoast-schema-graph\">{\"@context\":\"https:\/\/schema.org\",\"@graph\":[{\"@type\":\"WebPage\",\"@id\":\"https:\/\/web.umons.ac.be\/smos\/2023\/02\/23\/horse-chestnut-saponins-escins-isoescins-transescins-and-desacylescins\/\",\"url\":\"https:\/\/web.umons.ac.be\/smos\/2023\/02\/23\/horse-chestnut-saponins-escins-isoescins-transescins-and-desacylescins\/\",\"name\":\"Horse Chestnut Saponins\u2013Escins, Isoescins, Transescins, and Desacylescins - Service \/ FS - Synth\u00e8se et Spectrom\u00e9trie de Masse Organiques\",\"isPartOf\":{\"@id\":\"https:\/\/web.umons.ac.be\/smos\/#website\"},\"primaryImageOfPage\":{\"@id\":\"https:\/\/web.umons.ac.be\/smos\/2023\/02\/23\/horse-chestnut-saponins-escins-isoescins-transescins-and-desacylescins\/#primaryimage\"},\"image\":{\"@id\":\"https:\/\/web.umons.ac.be\/smos\/2023\/02\/23\/horse-chestnut-saponins-escins-isoescins-transescins-and-desacylescins\/#primaryimage\"},\"thumbnailUrl\":\"https:\/\/web.umons.ac.be\/app\/uploads\/sites\/80\/2023\/02\/2023-02-23.png\",\"datePublished\":\"2023-02-23T10:00:28+00:00\",\"dateModified\":\"2023-09-01T09:41:44+00:00\",\"author\":{\"@id\":\"https:\/\/web.umons.ac.be\/smos\/#\/schema\/person\/799f9fff96a5393a6f974013d89f3782\"},\"breadcrumb\":{\"@id\":\"https:\/\/web.umons.ac.be\/smos\/2023\/02\/23\/horse-chestnut-saponins-escins-isoescins-transescins-and-desacylescins\/#breadcrumb\"},\"inLanguage\":\"fr-FR\",\"potentialAction\":[{\"@type\":\"ReadAction\",\"target\":[\"https:\/\/web.umons.ac.be\/smos\/2023\/02\/23\/horse-chestnut-saponins-escins-isoescins-transescins-and-desacylescins\/\"]}]},{\"@type\":\"ImageObject\",\"inLanguage\":\"fr-FR\",\"@id\":\"https:\/\/web.umons.ac.be\/smos\/2023\/02\/23\/horse-chestnut-saponins-escins-isoescins-transescins-and-desacylescins\/#primaryimage\",\"url\":\"https:\/\/web.umons.ac.be\/app\/uploads\/sites\/80\/2023\/02\/2023-02-23.png\",\"contentUrl\":\"https:\/\/web.umons.ac.be\/app\/uploads\/sites\/80\/2023\/02\/2023-02-23.png\",\"width\":1974,\"height\":854,\"caption\":\"MALDI mass spectra (positive ionization mode) of three different saponin extracts: (a) Natural extract (NE); (b) Escins I, II and III enriched-extract (EE) obtained by flash chromatography separation (non-polar column\u2013acetonitrile gradient); (c) Microwave-assisted alkaline hydrolysis (pH 14\u2013150 \u00b0C\u20135 min) reaction extract (HE). The molecular structures are schematized by highlighting the targeted functions: in EE saponins, the esters are located on C21 (Tig or Ang) and C22 or C28 (Ac); in the HE saponins, the hydrolysis products possess alcohol groups on C21, C22, and C28.\"},{\"@type\":\"BreadcrumbList\",\"@id\":\"https:\/\/web.umons.ac.be\/smos\/2023\/02\/23\/horse-chestnut-saponins-escins-isoescins-transescins-and-desacylescins\/#breadcrumb\",\"itemListElement\":[{\"@type\":\"ListItem\",\"position\":1,\"name\":\"Home\",\"item\":\"https:\/\/web.umons.ac.be\/smos\/\"},{\"@type\":\"ListItem\",\"position\":2,\"name\":\"Horse Chestnut Saponins\u2013Escins, Isoescins, Transescins, and Desacylescins\"}]},{\"@type\":\"WebSite\",\"@id\":\"https:\/\/web.umons.ac.be\/smos\/#website\",\"url\":\"https:\/\/web.umons.ac.be\/smos\/\",\"name\":\"Service \/ FS - Synth\u00e8se et Spectrom\u00e9trie de Masse Organiques\",\"description\":\"\",\"potentialAction\":[{\"@type\":\"SearchAction\",\"target\":{\"@type\":\"EntryPoint\",\"urlTemplate\":\"https:\/\/web.umons.ac.be\/smos\/?s={search_term_string}\"},\"query-input\":{\"@type\":\"PropertyValueSpecification\",\"valueRequired\":true,\"valueName\":\"search_term_string\"}}],\"inLanguage\":\"fr-FR\"},{\"@type\":\"Person\",\"@id\":\"https:\/\/web.umons.ac.be\/smos\/#\/schema\/person\/799f9fff96a5393a6f974013d89f3782\",\"name\":\"Eric Weverbergh\",\"image\":{\"@type\":\"ImageObject\",\"inLanguage\":\"fr-FR\",\"@id\":\"https:\/\/web.umons.ac.be\/smos\/#\/schema\/person\/image\/\",\"url\":\"https:\/\/secure.gravatar.com\/avatar\/277eef236b3d46fa37342f3ff7201123ffcff78c8376e87dfb037d245a79e832?s=96&d=mm&r=g\",\"contentUrl\":\"https:\/\/secure.gravatar.com\/avatar\/277eef236b3d46fa37342f3ff7201123ffcff78c8376e87dfb037d245a79e832?s=96&d=mm&r=g\",\"caption\":\"Eric Weverbergh\"},\"url\":\"https:\/\/web.umons.ac.be\/smos\/author\/eweverbergh\/\"}]}<\/script>\n<!-- \/ Yoast SEO plugin. -->","yoast_head_json":{"title":"Horse Chestnut Saponins\u2013Escins, Isoescins, Transescins, and Desacylescins - Service \/ FS - Synth\u00e8se et Spectrom\u00e9trie de Masse Organiques","robots":{"index":"index","follow":"follow","max-snippet":"max-snippet:-1","max-image-preview":"max-image-preview:large","max-video-preview":"max-video-preview:-1"},"canonical":"https:\/\/web.umons.ac.be\/smos\/2023\/02\/23\/horse-chestnut-saponins-escins-isoescins-transescins-and-desacylescins\/","og_locale":"fr_FR","og_type":"article","og_title":"Horse Chestnut Saponins\u2013Escins, Isoescins, Transescins, and Desacylescins - Service \/ FS - Synth\u00e8se et Spectrom\u00e9trie de Masse Organiques","og_description":"Escins constitute an abundant family of saponins (saponosides) and are the most active components in Aesculum hippocastanum (horse chestnut\u2014HC) seeds. They are of great pharmaceutical interest as a short-term treatment for venous insufficiency. ...","og_url":"https:\/\/web.umons.ac.be\/smos\/2023\/02\/23\/horse-chestnut-saponins-escins-isoescins-transescins-and-desacylescins\/","og_site_name":"Service \/ FS - Synth\u00e8se et Spectrom\u00e9trie de Masse Organiques","article_published_time":"2023-02-23T10:00:28+00:00","article_modified_time":"2023-09-01T09:41:44+00:00","og_image":[{"width":1974,"height":854,"url":"https:\/\/web.umons.ac.be\/app\/uploads\/sites\/80\/2023\/02\/2023-02-23.png","type":"image\/png"}],"author":"Eric Weverbergh","twitter_card":"summary_large_image","twitter_misc":{"\u00c9crit par":"Eric Weverbergh","Dur\u00e9e de lecture estim\u00e9e":"2 minutes"},"schema":{"@context":"https:\/\/schema.org","@graph":[{"@type":"WebPage","@id":"https:\/\/web.umons.ac.be\/smos\/2023\/02\/23\/horse-chestnut-saponins-escins-isoescins-transescins-and-desacylescins\/","url":"https:\/\/web.umons.ac.be\/smos\/2023\/02\/23\/horse-chestnut-saponins-escins-isoescins-transescins-and-desacylescins\/","name":"Horse Chestnut Saponins\u2013Escins, Isoescins, Transescins, and Desacylescins - Service \/ FS - Synth\u00e8se et Spectrom\u00e9trie de Masse Organiques","isPartOf":{"@id":"https:\/\/web.umons.ac.be\/smos\/#website"},"primaryImageOfPage":{"@id":"https:\/\/web.umons.ac.be\/smos\/2023\/02\/23\/horse-chestnut-saponins-escins-isoescins-transescins-and-desacylescins\/#primaryimage"},"image":{"@id":"https:\/\/web.umons.ac.be\/smos\/2023\/02\/23\/horse-chestnut-saponins-escins-isoescins-transescins-and-desacylescins\/#primaryimage"},"thumbnailUrl":"https:\/\/web.umons.ac.be\/app\/uploads\/sites\/80\/2023\/02\/2023-02-23.png","datePublished":"2023-02-23T10:00:28+00:00","dateModified":"2023-09-01T09:41:44+00:00","author":{"@id":"https:\/\/web.umons.ac.be\/smos\/#\/schema\/person\/799f9fff96a5393a6f974013d89f3782"},"breadcrumb":{"@id":"https:\/\/web.umons.ac.be\/smos\/2023\/02\/23\/horse-chestnut-saponins-escins-isoescins-transescins-and-desacylescins\/#breadcrumb"},"inLanguage":"fr-FR","potentialAction":[{"@type":"ReadAction","target":["https:\/\/web.umons.ac.be\/smos\/2023\/02\/23\/horse-chestnut-saponins-escins-isoescins-transescins-and-desacylescins\/"]}]},{"@type":"ImageObject","inLanguage":"fr-FR","@id":"https:\/\/web.umons.ac.be\/smos\/2023\/02\/23\/horse-chestnut-saponins-escins-isoescins-transescins-and-desacylescins\/#primaryimage","url":"https:\/\/web.umons.ac.be\/app\/uploads\/sites\/80\/2023\/02\/2023-02-23.png","contentUrl":"https:\/\/web.umons.ac.be\/app\/uploads\/sites\/80\/2023\/02\/2023-02-23.png","width":1974,"height":854,"caption":"MALDI mass spectra (positive ionization mode) of three different saponin extracts: (a) Natural extract (NE); (b) Escins I, II and III enriched-extract (EE) obtained by flash chromatography separation (non-polar column\u2013acetonitrile gradient); (c) Microwave-assisted alkaline hydrolysis (pH 14\u2013150 \u00b0C\u20135 min) reaction extract (HE). The molecular structures are schematized by highlighting the targeted functions: in EE saponins, the esters are located on C21 (Tig or Ang) and C22 or C28 (Ac); in the HE saponins, the hydrolysis products possess alcohol groups on C21, C22, and C28."},{"@type":"BreadcrumbList","@id":"https:\/\/web.umons.ac.be\/smos\/2023\/02\/23\/horse-chestnut-saponins-escins-isoescins-transescins-and-desacylescins\/#breadcrumb","itemListElement":[{"@type":"ListItem","position":1,"name":"Home","item":"https:\/\/web.umons.ac.be\/smos\/"},{"@type":"ListItem","position":2,"name":"Horse Chestnut Saponins\u2013Escins, Isoescins, Transescins, and Desacylescins"}]},{"@type":"WebSite","@id":"https:\/\/web.umons.ac.be\/smos\/#website","url":"https:\/\/web.umons.ac.be\/smos\/","name":"Service \/ FS - Synth\u00e8se et Spectrom\u00e9trie de Masse Organiques","description":"","potentialAction":[{"@type":"SearchAction","target":{"@type":"EntryPoint","urlTemplate":"https:\/\/web.umons.ac.be\/smos\/?s={search_term_string}"},"query-input":{"@type":"PropertyValueSpecification","valueRequired":true,"valueName":"search_term_string"}}],"inLanguage":"fr-FR"},{"@type":"Person","@id":"https:\/\/web.umons.ac.be\/smos\/#\/schema\/person\/799f9fff96a5393a6f974013d89f3782","name":"Eric Weverbergh","image":{"@type":"ImageObject","inLanguage":"fr-FR","@id":"https:\/\/web.umons.ac.be\/smos\/#\/schema\/person\/image\/","url":"https:\/\/secure.gravatar.com\/avatar\/277eef236b3d46fa37342f3ff7201123ffcff78c8376e87dfb037d245a79e832?s=96&d=mm&r=g","contentUrl":"https:\/\/secure.gravatar.com\/avatar\/277eef236b3d46fa37342f3ff7201123ffcff78c8376e87dfb037d245a79e832?s=96&d=mm&r=g","caption":"Eric Weverbergh"},"url":"https:\/\/web.umons.ac.be\/smos\/author\/eweverbergh\/"}]}},"lang":"fr","translations":{"fr":305},"pll_sync_post":[],"_links":{"self":[{"href":"https:\/\/web.umons.ac.be\/smos\/wp-json\/wp\/v2\/posts\/305","targetHints":{"allow":["GET"]}}],"collection":[{"href":"https:\/\/web.umons.ac.be\/smos\/wp-json\/wp\/v2\/posts"}],"about":[{"href":"https:\/\/web.umons.ac.be\/smos\/wp-json\/wp\/v2\/types\/post"}],"author":[{"embeddable":true,"href":"https:\/\/web.umons.ac.be\/smos\/wp-json\/wp\/v2\/users\/157"}],"replies":[{"embeddable":true,"href":"https:\/\/web.umons.ac.be\/smos\/wp-json\/wp\/v2\/comments?post=305"}],"version-history":[{"count":1,"href":"https:\/\/web.umons.ac.be\/smos\/wp-json\/wp\/v2\/posts\/305\/revisions"}],"predecessor-version":[{"id":307,"href":"https:\/\/web.umons.ac.be\/smos\/wp-json\/wp\/v2\/posts\/305\/revisions\/307"}],"wp:featuredmedia":[{"embeddable":true,"href":"https:\/\/web.umons.ac.be\/smos\/wp-json\/wp\/v2\/media\/306"}],"wp:attachment":[{"href":"https:\/\/web.umons.ac.be\/smos\/wp-json\/wp\/v2\/media?parent=305"}],"wp:term":[{"taxonomy":"category","embeddable":true,"href":"https:\/\/web.umons.ac.be\/smos\/wp-json\/wp\/v2\/categories?post=305"},{"taxonomy":"post_tag","embeddable":true,"href":"https:\/\/web.umons.ac.be\/smos\/wp-json\/wp\/v2\/tags?post=305"}],"curies":[{"name":"wp","href":"https:\/\/api.w.org\/{rel}","templated":true}]}}