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Friday 29 April 2016

Steroidal saponins from Chlorophytum deistelianum

Volume 126, June 2016, Pages 34–40


  • a Laboratoire de Pharmacognosie, EA 4267/UFC, UFR des Sciences de Santé, Université de Bourgogne Franche-Comté, 7, Bd. Jeanne d’Arc, BP 87900, 21079 Dijon Cedex, France
  • b Département de Chimie Organique, Université de Yaoundé 1, BP 812 Yaoundé, Cameroon
  • c Universität Siegen, FB8, OC-II (AK Ihmels), Adolf-Reichwein-Strasse 2, D-57068 Siegen, Germany
  • d Cohiro, UFR des Sciences de Santé, 7, Bd. Jeanne d’Arc, BP 87900, 21079 Dijon Cedex, France


Highlights

Five spirostane- and four furostane-type saponins were isolated from Chlorophytum deistelianum.
Their structures were elucidated by extensive spectroscopic analyses.
Four previously undescribed steroidal saponins are characterized.
Three saponins among the seven tested showed cytotoxicity against two cell lines.

Abstract

Phytochemical investigation of the aerial parts of Chlorophytum deistelianum led to the isolation of four previously undescribed steroidal saponins called chlorodeistelianosides A–D with five known ones. Their structures were established mainly by extensive 1D and 2D NMR spectroscopic techniques and mass spectrometry as (25R)-3β-[(β-d-glucopyranosyl-(1 → 3)-[α-l-rhamnopyranosyl-(1 → 4)]-β-d-xylopyranosyl-(1 → 3)-[β-d-glucopyranosyl-(1 → 2)]-β-d-glucopyranosyl-(1 → 4)-β-d-galactopyranosyl)oxy]-5α-spirostan-12-one, (24S,25S)-24-[(β-d-glucopyranosyl)oxy]-3β-[(β-d-glucopyranosyl-(1 → 2)-[β-d-xylopyranosyl-(1 → 3)]-β-d-glucopyranosyl-(1 → 4)-β-d-galactopyranosyl)oxy]-5α-spirostan-12-one, (25R)-26-[(β-d-glucopyranosyl)oxy]-2α-hydroxy-22α-methoxy-5α-furostan-3β-yl β-d-glucopyranosyl-(1 → 2)-[β-d-xylopyranosyl-(1 → 3)]-β-d-glucopyranosyl-(1 → 4)-β-d-galactopyranoside, and (25R)-26-[(β-d-glucopyranosyl)oxy]-3β-[(β-d-glucopyranosyl-(1 → 2)-[β-d-xylopyranosyl-(1 → 3)]-β-d-glucopyranosyl-(1 → 4)-β-d-galactopyranosyl)oxy]-5α-furost-20(22)-en-12-one. Cytotoxicity of most compounds was evaluated against one human cancer cell line (SW480) and one rat cardiomyoblast cell line (H9c2). Among them, three known spirostane-type glycosides exhibited cytotoxicity on both cell lines with IC50 ranging from 8 to 10 μM.

Graphical abstract

Four previously undescribed and five known steroidal saponins were isolated from the aerial parts of Chlorophytum deistelianum. Their structures were elucidated by extensive spectroscopic analyses. Seven compounds were evaluated for their cytotoxicity against two cell lines (SW480 and H9c2), three of them exhibiting activity on both cell lines.
Image for unlabelled figure

Keywords

  • Chlorophytum deistelianum;
  • Asparagaceae;
  • Steroidal saponins;
  • Cytotoxicity
Corresponding author.