Spirostanol Saponins from Flowers of <i>Allium Porrum</i> and Related Compounds Indicating Cytotoxic Activity and Affecting Nitric Oxide Production Inhibitory Effect in Peritoneal Macrophages

Saponins, a diverse group of natural compounds, offer an interesting pool of derivatives with biomedical application. In this study, three structurally related spirostanol saponins were isolated and identified from the leek flowers of <i>Allium porrum</i> L. (garden leek). Two of them we...

Descripción completa

Guardado en:

Detalles Bibliográficos
Autores principales:	Juraj Harmatha, Miloš Buděšínský, Zdeněk Zídek, Eva Kmoníčková
Formato:	article
Lenguaje:	EN
Publicado:	MDPI AG 2021
Materias:	<i>Allium porrum</i> leek flowers steroid saponins aginoside alliporin cytotoxicity Organic chemistry QD241-441
Acceso en línea:	https://doaj.org/article/2d9f670eda3840e58c74abb17dc88a20
Etiquetas:	Agregar Etiqueta Sin Etiquetas, Sea el primero en etiquetar este registro!

id	oai:doaj.org-article:2d9f670eda3840e58c74abb17dc88a20
record_format	dspace
spelling	oai:doaj.org-article:2d9f670eda3840e58c74abb17dc88a202021-11-11T18:31:22ZSpirostanol Saponins from Flowers of <i>Allium Porrum</i> and Related Compounds Indicating Cytotoxic Activity and Affecting Nitric Oxide Production Inhibitory Effect in Peritoneal Macrophages10.3390/molecules262165331420-3049https://doaj.org/article/2d9f670eda3840e58c74abb17dc88a202021-10-01T00:00:00Zhttps://www.mdpi.com/1420-3049/26/21/6533https://doaj.org/toc/1420-3049Saponins, a diverse group of natural compounds, offer an interesting pool of derivatives with biomedical application. In this study, three structurally related spirostanol saponins were isolated and identified from the leek flowers of <i>Allium porrum</i> L. (garden leek). Two of them were identical with the already known leek plant constituents: aginoside (1) and 6-deoxyaginoside (2). The third one was identified as new component of <i>A. porrum</i>; however, it was found identical with yayoisaponin A (3) obtained earlier from a mutant of elephant garlic <i>Allium ampeloprasun</i> L. It is a derivative of the aginoside (1) with additional glucose in its glycosidic chain, identified by MS and NMR analysis as (2α, 3β, 6β, 25<i>R</i>)-2,6-dihydroxyspirostan-3-yl β-D-glucopyranosyl-(1 → 3)-β-D-glucopranosyl-(1 → 2)-[β-D-xylopyranosyl-(1 → 3)]-β-D-glucopyranosyl]-(1 → 4)-β-D-galactopyranoside, previously reported also under the name alliporin. The leek native saponins were tested together with other known and structurally related saponins (tomatonin and digitonin) and with their related aglycones (agigenin and diosgenin) for in vitro cytotoxicity and for effects on NO production in mouse peritoneal cells. The highest inhibitory effects were exhibited by 6-deoxyaginoside. The obtained toxicity data, however, closely correlated with the suppression of NO production. Therefore, an unambiguous linking of obtained bioactivities of saponins with their expected immunobiological properties remained uncertain.Juraj HarmathaMiloš BuděšínskýZdeněk ZídekEva KmoníčkováMDPI AGarticle<i>Allium porrum</i>leek flowerssteroid saponinsaginosidealliporincytotoxicityOrganic chemistryQD241-441ENMolecules, Vol 26, Iss 6533, p 6533 (2021)
institution	DOAJ
collection	DOAJ
language	EN
topic	<i>Allium porrum</i> leek flowers steroid saponins aginoside alliporin cytotoxicity Organic chemistry QD241-441
spellingShingle	<i>Allium porrum</i> leek flowers steroid saponins aginoside alliporin cytotoxicity Organic chemistry QD241-441 Juraj Harmatha Miloš Buděšínský Zdeněk Zídek Eva Kmoníčková Spirostanol Saponins from Flowers of <i>Allium Porrum</i> and Related Compounds Indicating Cytotoxic Activity and Affecting Nitric Oxide Production Inhibitory Effect in Peritoneal Macrophages
description	Saponins, a diverse group of natural compounds, offer an interesting pool of derivatives with biomedical application. In this study, three structurally related spirostanol saponins were isolated and identified from the leek flowers of <i>Allium porrum</i> L. (garden leek). Two of them were identical with the already known leek plant constituents: aginoside (1) and 6-deoxyaginoside (2). The third one was identified as new component of <i>A. porrum</i>; however, it was found identical with yayoisaponin A (3) obtained earlier from a mutant of elephant garlic <i>Allium ampeloprasun</i> L. It is a derivative of the aginoside (1) with additional glucose in its glycosidic chain, identified by MS and NMR analysis as (2α, 3β, 6β, 25<i>R</i>)-2,6-dihydroxyspirostan-3-yl β-D-glucopyranosyl-(1 → 3)-β-D-glucopranosyl-(1 → 2)-[β-D-xylopyranosyl-(1 → 3)]-β-D-glucopyranosyl]-(1 → 4)-β-D-galactopyranoside, previously reported also under the name alliporin. The leek native saponins were tested together with other known and structurally related saponins (tomatonin and digitonin) and with their related aglycones (agigenin and diosgenin) for in vitro cytotoxicity and for effects on NO production in mouse peritoneal cells. The highest inhibitory effects were exhibited by 6-deoxyaginoside. The obtained toxicity data, however, closely correlated with the suppression of NO production. Therefore, an unambiguous linking of obtained bioactivities of saponins with their expected immunobiological properties remained uncertain.
format	article
author	Juraj Harmatha Miloš Buděšínský Zdeněk Zídek Eva Kmoníčková
author_facet	Juraj Harmatha Miloš Buděšínský Zdeněk Zídek Eva Kmoníčková
author_sort	Juraj Harmatha
title	Spirostanol Saponins from Flowers of <i>Allium Porrum</i> and Related Compounds Indicating Cytotoxic Activity and Affecting Nitric Oxide Production Inhibitory Effect in Peritoneal Macrophages
title_short	Spirostanol Saponins from Flowers of <i>Allium Porrum</i> and Related Compounds Indicating Cytotoxic Activity and Affecting Nitric Oxide Production Inhibitory Effect in Peritoneal Macrophages
title_full	Spirostanol Saponins from Flowers of <i>Allium Porrum</i> and Related Compounds Indicating Cytotoxic Activity and Affecting Nitric Oxide Production Inhibitory Effect in Peritoneal Macrophages
title_fullStr	Spirostanol Saponins from Flowers of <i>Allium Porrum</i> and Related Compounds Indicating Cytotoxic Activity and Affecting Nitric Oxide Production Inhibitory Effect in Peritoneal Macrophages
title_full_unstemmed	Spirostanol Saponins from Flowers of <i>Allium Porrum</i> and Related Compounds Indicating Cytotoxic Activity and Affecting Nitric Oxide Production Inhibitory Effect in Peritoneal Macrophages
title_sort	spirostanol saponins from flowers of <i>allium porrum</i> and related compounds indicating cytotoxic activity and affecting nitric oxide production inhibitory effect in peritoneal macrophages
publisher	MDPI AG
publishDate	2021
url	https://doaj.org/article/2d9f670eda3840e58c74abb17dc88a20
work_keys_str_mv	AT jurajharmatha spirostanolsaponinsfromflowersofialliumporrumiandrelatedcompoundsindicatingcytotoxicactivityandaffectingnitricoxideproductioninhibitoryeffectinperitonealmacrophages AT milosbudesinsky spirostanolsaponinsfromflowersofialliumporrumiandrelatedcompoundsindicatingcytotoxicactivityandaffectingnitricoxideproductioninhibitoryeffectinperitonealmacrophages AT zdenekzidek spirostanolsaponinsfromflowersofialliumporrumiandrelatedcompoundsindicatingcytotoxicactivityandaffectingnitricoxideproductioninhibitoryeffectinperitonealmacrophages AT evakmonickova spirostanolsaponinsfromflowersofialliumporrumiandrelatedcompoundsindicatingcytotoxicactivityandaffectingnitricoxideproductioninhibitoryeffectinperitonealmacrophages
_version_	1718431814652002304

Spirostanol Saponins from Flowers of <i>Allium Porrum</i> and Related Compounds Indicating Cytotoxic Activity and Affecting Nitric Oxide Production Inhibitory Effect in Peritoneal Macrophages

Ejemplares similares