Structure and cytotoxicity of steroidal glycosides from Allium schoenoprasum

Timité, Gaoussou; Mitaine-Offer, Anne Claire; Miyamoto, Tomofumi; Tanaka, Chiaki; Mirjolet, JF; Duchamp, Olivier; Lacaille-Dubois, MA

doi:10.1055/s-0032-1320936

Cited by 5 publications

(7 citation statements)

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“…De otra parte, la actividad citotóxica de las saponinas ha sido explorada y discutida en un sinnúmero de artículos científicos sobre distintas especies vegetales. Varios autores coinciden en que la estructura de la cadena del oligosacárido, los sitios de enlace interglucosídicos -más que el esqueleto de la sapogenina o la línea celular-, son los factores que definen las actividades citotóxicas de las saponinas [1, 13,69,73]; además, en que la presencia del ácido carboxílico libre en C-28 es esencial para la citotoxicidad [1,31]. Kuljanabhagavad y colaboradores [13] evaluaron la actividad citotóxica de cuatro saponinas (dos monodesmosidicas y dos bidesmosidicas) previamente identificadas, así como de sus respectivas sapogeninas en células HeLa por medio del ensayo MTT.…”

Section: Actividad Membranolítica Hipocolesterolémica Antiadipogéniunclassified

Saponinas de quinua (Chenopodium quinoa Willd.): un subproducto con alto potencial biológico

Ahumada

Ortega

Chito

et al. 2016

Rev. Colomb. Cienc. Quim. Farm.

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Las saponinas son un tipo de metabolito secundario ampliamente estudiado por susreconocidas propiedades biológicas. Gran parte de las investigaciones en fitoquímicaestán dirigidas a encontrar nuevas fuentes naturales de saponinas con aplicaciónmedicinal. La quinua (Chenopodium quinoa Willd.) es una planta que ha alcanzadoun valioso reconocimiento por ser una fuente de alimentos altamente nutritivos, asícomo una especie rica en saponinas triterpénicas contenidas, principalmente, en lacáscara de las semillas. A la fecha, se han identificado alrededor de 30 saponinas derivadasde la hederagenina y de los ácidos oleanólico, fitolacagénico y serjanico en laplanta. El consumo del grano de quinua implica la remoción de la cáscara a fin dereducir su sabor amargo, la ingesta de niveles residuales de saponinas y la obtenciónde un subproducto rico en las mismas. Esta revisión, inicialmente, ofrece una contextualizacióngeneral de las saponinas; posteriormente, recopila las característicasestructurales de las saponinas identificadas en la quinua, describe el efecto del procesamientodel grano en su contenido de saponinas y, finalmente, expone los efectosbiológicos explorados con extractos de saponinas de quinua, los cuales pueden serconsiderados como punto de partida en investigaciones futuras dirigidas al fortalecimientode su uso en el campo farmacéutico y/o nutracéutico.

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Section: Actividad Membranolítica Hipocolesterolémica Antiadipogéniunclassified

Saponinas de quinua (Chenopodium quinoa Willd.): un subproducto con alto potencial biológico

Ahumada

Ortega

Chito

et al. 2016

Rev. Colomb. Cienc. Quim. Farm.

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“…The attachment of D-rhamnose and the second D-glucose moieties to carbons C-2 Gal and C-3 Gal, respectively, was confirmed from the long range correlations of their anomeric carbons (δ C 102.3, H-1 Rh and 105.9, H-1 Glc ) to the respective protons (δ H 3.77, H-2 Gal and 3.74, H-3 Gal ), respectively. The full assignment of the protons and carbons of compound 3 was further confirmed by the analysis of 2D NMR spectra ( 1 H-1 H gDQCOSY, gHSQCAD, gHMBCAD, ROESY and zTOCSY) and by comparison to the published data of the related glycosides [17,18,22,23]. Thus, the structure of compound 3 was identified as (25R)-spirost-5-en-3-…”

Section: Structure Elucidationmentioning

confidence: 67%

Chemical constituents from Solanum glabratum Dunal var. sepicula

Abdel‐Sattar¹,

Farag²,

Mahrous³

2013

Planta Med

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In the course of screening program of Saudi plants for their potential biological activity, the methanolic extract of Solanum glabratum Dunal var. sepicula as well as its different fractions were tested for its possible cytoxicity in prostate cancer (PC3) and colon cancer (HT29) cell lines using the MTT assay. In the present study, three spirostan saponins and one flavonoid glycoside were isolated from the active n-butanol fraction through a bio-guided fractionation approach. Two new saponin glycosides were identified as 23 (2) and (25R)-spirost-5-en-3-ol 3-O-α-L-rhamnopyranosyl-(1→2)-O-[β-Dglucopyranosyl-(1→3)]-β-D-galactopyranoside (3). In addition, two known compounds were also isolated and identified as isorhamnetin-3-O-α-L-rhamnopyranosyl (1→6) β-D-glucopyranoside (1) and (23S, 25R)-spirost-5en-3, 23 diol 3-O-α-L-rhamnopyranosyl-(1→2)-O-[α-L-rhamnopyranosyl-(1→4)]-β-D-glucopyranoside (4). The structures of the isolated compounds were elucidated based on their MS, one dimensional and extensive two dimensional NMR spectral data. Among the isolated metabolites, compound 3 showed the highest cytotoxic activity in both PC3 and HT29 cell lines with an IC 50 values of 14.8 and 19.5 µg/mL, respectively.

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“…[3,4] Steroidal saponins exhibit various biological activities. [5][6][7][8][9] The Allium plants are traditionally eaten in northern China, Mongolia, and Vietnam. They are used in Vietnam for the treatment of spermatorrhoea, hemoptysis, epistaxis, cough, sore throat, asthma, dysentery, and dyspepsia.…”

Section: Introductionmentioning

confidence: 99%

“…The main constituents of the Allium species were proven to be organosulfurs, polyphenols, and steroid saponins [3,4] . Steroidal saponins exhibit various biological activities [5–9] . The Allium plants are traditionally eaten in northern China, Mongolia, and Vietnam.…”

Section: Introductionmentioning

confidence: 99%

Furostane Saponins from the Seeds of Allium ramosum and Their Lipid Accumulation Inhibitory Activity

Yến

Tài

Yến

et al. 2022

Chemistry & Biodiversity

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Three new furostane saponins, ramofurosides A -C (1 -3), and two known saponins, fistulosaponin B ( 4) and (25R)-26- O-β-D-glucopyranosyl-1β,3β,26-trihydroxyfurosta-5,20(22 5) were isolated from the methanol extract of Allium ramosum seeds. Their structures were identified based on spectroscopic evidence and comparison with those reported in the literature. All compounds were evaluated for reduction of lipid accumulation in HepG2 cell lines. As a result, compounds 1 and 3 showed a significant reduction in total lipid content by 27.93 � 3.05 and 27.54 � 1.68 %, respectively, at a concentration of 100 μM.

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Structure and cytotoxicity of steroidal glycosides from Allium schoenoprasum

Cited by 5 publications

References 0 publications

Saponinas de quinua (Chenopodium quinoa Willd.): un subproducto con alto potencial biológico

Saponinas de quinua (Chenopodium quinoa Willd.): un subproducto con alto potencial biológico

Chemical constituents from Solanum glabratum Dunal var. sepicula

Furostane Saponins from the Seeds of Allium ramosum and Their Lipid Accumulation Inhibitory Activity

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