Triterpene Glycosides from the Underground Parts of Caulophyllum thalictroides

Abstract

A total of 22 triterpene glycosides, including 10 new compounds (1-10), were isolated from the underground parts of Caulophyllum thalictroides. The structures of the new glycosides were determined on the basis of extensive spectroscopic analyses, including two-dimensional (2D) NMR data, and of hydrolytic cleavage followed by chromatographic or spectroscopic analyses. All 22 compounds were evaluated for cytotoxicity against HL-60 human leukemia cells. The triterpene monodesmosides based on oleanolic acid (1 and 11-16) showed cytotoxic activity against HL-60 cells with IC(50) values that ranged from 3.4 to 15.9 microg/mL.

Genus Caulophyllum: An Overview of Chemistry and Bioactivity

“… Scheme 1 summarizes the procedures for crude isolation of alkaloids and triterpene saponins from genus Caulophyllum . The roots and rhizomes of Caulophyllum plants are extracted with methanol or 70% ethanol by maceration [13, 20] or reflux [21], and the combined extracts are concentrated in vacuo to dryness. Then two schemes are available for acquiring the alkaloid and saponin fractions, namely, liquid-liquid partition and liquid-solid column chromatography methods [21].…”

“…The combined organic layers were evaporated to obtain total saponin fraction [20]. Column chromatography is also a popular method to enrich total alkaloids and saponins from Caulophyllum plants by choosing optimal macroporous or (and) ion exchange resins [13, 21, 22]. …”

“…Twelve kinds of aglycones have been discovered from the genus Caulophyllum (Figure 2(a)) [20, 21, 30]. Before 2009, only four kinds of sapogenins were discovered from genus Caulophyllum , namely, oleanolic acid (AG 1 ), hederagenin (AG 2 ), echinocystic acid (AG 3 ), and caulophyllogenin (AG 4 ).…”

Triterpenoid saponins from Anemone raddeana

“…as the ester glycosyl unit at C-28 of the aglycone were isolated not only from Anemone (Mazutani et al, 1984;Li et al, 2004), but also from other genera of the Ranunculaceae such as Pulsatilla (Shimizu et al, 1978) and Clematis (Chandel and Rastogi, 1980), as well as related families such as Lardizabalaceae (Chandel and Rastogi, 1980), Podophyllaceae (Agarwal and Rastogi, 1974) and Berberidaceae (Matsuo et al, 2009). However, saponins with the above trisaccharide in repeated chains as the ester glycosyl unit at C-28 of the aglycone were isolated only from Ranunculaceae (Wang et al, 1997;Li et al, 2008;Watanabe et al, 2003).…”

Triterpene Glycosides from the Stems and Leaves of <i>Lonicera japonica</i>

“…The stems and leaves of L. japonica have been chemically investigated, and iridoid glycosides and a number of triterpene glycosides have been isolated; some of these compounds may contribute to the medicinal effects of this crude drug. [2][3][4][5][6] As part of our continuing investigation of triterpene glycosides from medicinal plants, [7][8][9][10][11][12][13][14][15][16][17][18][19][20][21] we conducted phytochemical screening of the stems and leaves of L. japonica and isolated five new triterpene glycosides, together with five known ones. Here we report the structures of these compounds, based on extensive spectroscopic analysis, including two-dimensional (2D)-NMR experiments, and the results of hydrolysis.…”