Two New Monodesmosidic Triterpene Saponins from Gypsophila oldhamiana

Abstract

Gypsophila oldhamiana MIQ. (Caryophyllaceae) is widely distributed in Shanxi and Shandong province in China. The roots of this plant have been used as an alternative remedy to the most common traditional Chinese medicine Yin-Chai-Hu (roots of Stellria dichotoma var. Lanceolata Bge) and utilized to treat heat due to yin deficiency, hectic and tidal fever, and infantile malnutrition syndrome in China.1) Previous chemical investigation on the roots of this species led to the isolation of saponins, sterols, and fatty acid.2-5) As a part of our search for bioactive saponins from traditional Chinese medicine, we present in this report the isolation and structural elucidation of two new saponins (1, 2) from the roots of G. oldhamiana. In addition, their immunologic properties were investigated. Results and DiscussionThe 70% EtOH extract of the roots of G. oldhamiana was partitioned with water and CHCl 3 . The water layer was chromatographed successively over marcoporous resin D101, silica gel, and ODS-C 18 to yield compounds 1 and 2, which were identified as quillaic acid, a-L-arabinopyranosyl- (2) (Fig. 1).Compound 1 was obtained as a white amorphous powder. Its molecular formula was assigned as C 57 H 90 O 25 determined from its pseudomolecular ion peak at m/z 1175.5833 [MϩH] ϩ (Calcd 1175.5849) in the HR-FAB-MS. The IR spectrum showed absorption at 3600-3300 cm Ϫ1 (-OH) and 1724 cm Ϫ1 (ester carbonyl). The alkaline hydrolysis of 1 yielded quillaic acid identified by TLC in comparison with an authentic sample 6) and an oligosaccharide. Acid hydrolysis of 1 afforded quillaic acid and monosaccharides, D-fucose, L-rhamnose, D-xylose, and L-arabinose identified by gas chromatography in comparison with standard monosaccharides.6) The proton and carbon signals (Tables 1, 2) were assigned by a combination analysis of 1D and 2D NMR (HSQC and HMBC). The aglycone moiety was further identified by comparison with literature data.2) The chemical shifts of C-3 (d 71.7) and C-28 (d 176.3) indicated that 1 was a monodesmosidic glycoside in which the sugar moiety was connected at C-28. units were determined from their 3 J H1,H2 coupling constants (7-8 Hz) and 13 C-NMR data.8) The a-anomeric configuration of rhamnose was judged by its C 5 (d 68.3).9) The sequence of the oligosaccharide chains in 1 was determined from the HMBC spectrum. Two new monodesmosidic triterpene saponins were isolated from the roots of Gypsophila oldhamiana (Caryophyllaceae). Their structures were elucidated on the basis of spectral data to be quillaic acid, a a-L-arabinopyranosyl- (

Different Apoptotic Effects of Triterpenoid Saponin-Rich <i>Gypsophila oldhamiana</i> Root Extract on Human Hepatoma SMMC-7721 and Normal Human Hepatic L02 Cells

“…Its roots have been usually used as a folk medicine to treat fever, consumptive disease, and infantile malnutrition syndrome in China. 11) Previous chemical researches on its roots have revealed the occurrence of saponins, sterols, and fatty acid, [11][12][13][14][15] and triterpenoid saponins and saponin-rich extract of its roots showed obvious anticancer activity in vitro and in vivo. [16][17][18] However, there is no report on the mechanisms responsible for the anti-proliferative effects.…”

“…The supernatant was concentrated to 50 mL with a rotary evaporator under reduced pressure. As previously described, 11,[13][14][15] the extract was partitioned with ethyl acetate and n-butanol, respectively. The n-butanol extract was subjected to MCI column (MeOH-H 2 O 50%, 90%), and the 90% fraction was evaporated under vacuum and then lyophilized to give the TGOE.…”

Triterpenoid Saponins from Gypsophila altissima L.

“…3,4) G. altissima, a perennial herbaceous plant, about 50-80 cm tall, grows at the mountain slopes, valley grasslands, floodlands and ditches at 1350-2450 m above the sea level. Up to now, there is no report of the chemical study about this plant.…”

Naturally Occurring Triterpenoid Saponins

“…In the concentration range of 10 -100 mg/ml, it showed a significant enhancement of granulocyte phagocytosis (40 -75%), whereas, in the concentration range of 100 ng/ml -1 pg/ml, it exerted an immunosuppressive effect (65 -22%) in vitro in the T-cell activation assay [148] [524].…”