Antiproliferative and anti-inflammatory polyhydroxylated spirostanol saponins from Tupistra chinensis

Abstract

Tupistra chinensis is widely distributed in southwestern China and its rhizome is a famous folk medicine for the treatment of carbuncles and pharyngitis. Its chemical identity of potent antiproliferative and anti-inflammatory constituents has been carried out in this study. Twenty-three polyhydroxylated spirostanol saponins, including nine novels, were isolated and identified. The new spirostanol saponins were elucidated as spirost-25(27)-en-1β,2β,3β,4β,5β-pentol-2-O-β-D-xylopyranoside (1), spirost-25(27)- en-1β,2β,3β,4β,5β-pentol-2-O-α-L-arabinopyranoside (2), spirost-25(27)-en- 1β,3α,5β-triol (12), spirost-25(27)-en-1β,3α,4β,5β,6β-pentol (13), spirost-25(27)-en- 1β,2β,3β,5β-tetraol-5-O-β-D-glucopyranoside (16), 5β-spirost-25(27)-en-1β,3β-diol- 3-O-β-D-glucopyranosyl-(1 → 4)-β-D-glucopyranoside (17), (25R)-5β-spirostan- 1β,3β-diol-3-O-β-D-glucopyranosyl-(1 → 6)-β-D-glucopyranoside (18), (25R)-5β- spirostan-1β,3β-diol-3-O-β-D-fructofuranosyl-(2 → 6)-β-D-glucopyranoside (19), 5β-spirost-25(27)-en-3β-ol-3-O-β-D-glucopyranosyl-(1 → 4)-β-D-glucopyranoside (20). The antiproliferative effects against seven human cancer cell lines and inhibitory activities on nitric oxide (NO) production induced by lipopolysaccharide (LPS) in a macrophage cell line RAW 264.7 were assayed for all the isolated compounds. Compounds 17, 19 and 21 exhibited potential antiproliferative activities against all of human cancer cell lines tested. Compounds 21 showed significant inhibition on NO production with IC50 values of 11.5 μM. These results showed that the spirostanol saponins isolated from the dried rhizomes of T. chinensis have potent antiproliferative and anti-inflammatory activities and T. chinensis might be used as anticancer and.anti-inflammatory supplement.

Chemical composition, antioxidant, anti-inflammatory, and cytotoxic activities of Opuntia stricta cladodes

“…There are two main types of saponin, triterpenoid saponins and steroidal saponins. Saponins have been reported to exert different pharmacological actions such as anti-inflammatory[71], immunoregulatory [72] and also antineoplastic [73]. They are also known to display antioxidant properties[74].…”

Separation and Bioactive Assay of 25R/S-Spirostanol Saponin Diastereomers from Yucca schidigera Roezl (Mojave) Stems

“…Until now, successful preparation examples for (25 R / S )-spiromeric epimers were accomplished by SFC isolation [ 11 , 12 ] usually. Meanwhile, it is very rare still for preparing this type of R / S mixture using HPLC methods [ 13 , 14 , 15 , 16 ]. On the other hand, among the rare isolation examples, all of them are only for the isolation of C 12 unsubstituted 25 R / S -spirostanol saponin diastereomers, but no reference was found to separate C 12 carbonylated 25 R / S -ones.…”

Saponins from Chinese Medicines as Anticancer Agents

“…Saponins exert various pharmacological effects, including cardiovascular protective activity [4], anti-inflammatory [5], antiviral [6], and immunoregulatory effects [7]. Moreover, recent studies have reported that saponins demonstrate significant anticancer activity, such as anti-proliferation [8], anti-metastasis [9], anti-angiogenesis [10] and reversal of multi-drug resistance (MDR) effects [11] through mechanisms that include induction of apoptosis and promotion of cell-differentiation.…”