Two New Sulfated Saponins from the Roots of Gypsophila bermejoi

Abstract

Two new sulfated saponins (1 and 2) were isolated from a butanol-soluble extract of the roots of Gypsophila bermejoi and were identified by a combination of chemical degradation and spectral methods as the 3beta-sulfate ester of gypsogenin 28-O-beta-D-glucopyranosyl(1-->2)-[beta-D-glucopyranosyl(1-->6)]-beta -D-glucopyranoside (1), and the 23-sulfate ester of hederagenin 28-O-beta-D-glucopyranosyl(1-->2)-[beta-D-glucopyranosyl(1-->6)]-beta -D-glucopyranoside (2), respectively. Plants of the genus Gypsophila (Caryophyllaceae) are important industrially because of the capacity of their saponin constituents to behave like natural detergents.1 Saponins from this genus are based on oleanolic acid (3-hydroxyolean-12-en-28-oic acid), with gypsogenin being the main pentacyclic triterpenoidal aglycon found. In general, this aglycon is substituted at the C-3 hydroxyl and/or C-28 carboxylic acid groups by saccharide units.2

Triterpenoid saponins of the Caryophyllaceae and Illecebraceae family

“…Bieb., Gypsophila bermejoi G. Ló pez and G. trichotoma Wend. are reported within the Caryophyllaceae family (Acebes et al, 1998a;Gaidi et al, 2005;Krasteva et al, 2009). G. repens L. and Polycarpon succulentum J.…”

New Pentacyclic Triterpenes from Gypsophila oldhamiana and Their Biological Evaluation as Glycogen Phosphorylase Inhibitors

“…553.3199), which suggested the presence of a sulfate group in the molecule. The IR spectrum showed absorption bands for OH (3447 cm À 1 ), CO ) groups [12]. Acid hydrolysis of 3 with 10% HCl was followed by extraction with AcOEt.…”

Characterization of in vivo anti-rotavirus activities of saponin extracts from Quillaja saponaria Molina

“…Saponins have been exploited as natural detergents due to their ability to produce stable foams when dissolved in water (Acebes et al, 1998; Lamri et al, 1988; Tarade, 2005). Having both fat-soluble and water-soluble properties, saponins make excellent surfactants and have been used as soaps for hundreds of years.…”