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A phytochemical investigation of the steroidal saponins from the rhizomes of Paris polyohylla var. latifolia led to the discovery and characterization of three new spirostanol saponins, papolatiosides A-C ( 1 - 3 ), and nine known compounds ( 4 - 12 ). Their structures were established via extensive spectroscopic data analysis and chemical methods. Interestingly, compounds 1 and 2 possessed a fructosyl in their oligosaccharide moiety, which is rare in natural product and was firstly reported in family Melanthiaceae. The cytotoxicity of these saponins against several human cancer cell lines was evaluated by a CCK-8 experiment. As a result, compound 1 exhibited a significant cytotoxic effect on LN229, U251, Capan-2, HeLa, and HepG2 cancer cells with IC 50 values of 4.18 ± 0.31, 3.85 ± 0.44, 3.26 ± 0.34, 3.30 ± 0.38 and 4.32 ± 0.51 μM, respectively. In addition, the result of flow cytometry analysis indicated that compound 1 could induce apoptosis of glioma cells LN229. The underlying mechanism was explored by network pharmacology and western bolt experiments, which indicated that compound 1 could induce glioma cells LN229 apoptosis by regulating the EGFR/PI3K/Akt/mTOR pathway.

Phytochemical reinvestigation on the whole plants of Ypsilandra thibetica obtained four new spirostanol glycosides, named ypsilandrosides U-X (1-4), and one new cholestanol glycoside, named ypsilandroside Y (5). Their structures have been established by extensive spectroscopic data and chemical methods. Among them, compound 4 is a rare spirostanol glycoside which possesses a novel 5(6 → 7) abeo-steroidal aglycone, while compound 1 is a first spirostanol bisdesmoside attached to C-3 and C-12, respectively, isolated from the genus Ypsilandra. The induced platelet aggregation activity of the isolates was tested., (© 2022. The Author(s).)

The species of Paris genus is a prolific source of structurally diverse steroidal saponins responsible for multivarious biological properties. The first phytochemical investigation on the steroidal saponin constituents from the rhizomes of Paris vaniotii Lévl. led to the discovery and structural characterization of four new spirostanol saponins, named parisvaniosides A-D (1-4), and one new furostanol glycoside, named parisvanioside E (5), along with eleven known analogues (6-16). Their structures were unambiguously established on the basis of extensive spectroscopic analysis and comparison with the reported spectroscopic data. Compound 1 is a rare spirostanol saponin sharing with a C-9/C-11 double bond and a peroxy group located between C-5 and C-8 of the aglycone, whereas 3 and 4 are unusual C-27 steroidal sapoins with hydroxyl/methoxyl at both C-5 and C-6. Furthermore, 5 is the first furostanol saponin with a unique aglycone featuring two trisubstituted double bonds in ring B. All isolated saponins were evaluated for their anti-inflammatory effects on a lipopolysaccharide (LPS)-stimulated nitric oxide (NO) production model in RAW 264.7 macrophages., (Copyright © 2021 Elsevier Inc. All rights reserved.)

T-17, a bioactive spirostanol saponin extracted from Tupistra chinensis Baker, was previously reported with anti-inflammatory and cytotoxic activities. However, the mechanism underlying of its anti-proliferation activity remains to be elucidated. In this study, we investigated the anti-gastric cancer cell growth activity of T-17 in terms of cell viability, colony formation, cell cycle, induction of apoptosis/autophagy, and JNK pathway. T-17 showed dose-dependent cytotoxicity in SGC-7901 and AGS cell lines, it induced caspase-mediated apoptosis as well as G0/G1 phase arrest and modulation of cyclinE2 and p21 expression. In addition, T-17 promoted the cancer cell autophagy as evidenced with increased expression of Beclin-1 and decreased p62 in western blot and formation of GFP-LC3 puncta. Furthermore, T-17-induced autophagy decreased gastric cancer cell apoptosis as assessed by pharmacological autophagy inhibitors and ATG5 siRNA usage. Importantly, the activation of JNK pathway was simultaneously involved in T-17-induced apoptosis and autophagy. Taken together, the results suggest that T-17 is a promising cytotoxic agent for therapeutic treatment of human gastric adenocarcinoma, which provides a good foundation for further research and development of Tupistra chinensis Baker., (Copyright © 2020 Elsevier Inc. All rights reserved.)

Yucca schidigera Roezl (Mojave), a kind of ornamental plant belonging to the Yucca genus (Agavaceae), whose extract exhibits important roles in food, beverage, cosmetic and feed additives owing to its rich spirostanol saponins. To provide a comprehensive chemical profiling of the spirostanol saponins in it, this study was performed by using a multi-phase liquid chromatography method combining a reversed phase chromatography T 3 column with a normal phase chromatography silica column for the separation and an ESI-Q-Exactive-Orbitrap MS in positive ion mode as the detector. By comparing the retention time and ion fragments with standards, thirty-one spirostanol saponins were identified. In addition, according to the summary of the chromatographic retention behaviors and the MS/MS cleavage patterns and biosynthetic pathway, another seventy-nine spirostanol saponins were speculatively identified, forty ones of which were potentially new ones. Moreover, ten novel spirostanol saponins (three pairs of (25 R/S )-spirostanol saponin isomer mixtures) were targeted for isolation to verify the speculation. Then, the comprehensive chemical profiling of spirostanol saponins from Y. schidigera was reported here firstly.

The first phytochemical investigation on the steroidal saponins from the stems and leaves of Paris polyohylla var. chinensis led to the discovery and characterization of six new spirostanol saponins, named polyphyllosides A-F (1-6), along with four known analogues (7-10). Their structures were unambiguously established via extensive spectroscopic data and chemical methods. Both polyphyllosides A and B had a rare aglycone with a C-4/C-5 double bond and a C-6 hydroxy group moiety, whereas polyphylloside C represents the first saponin with a unique aglycone sharing a C-6/C-7 double bond and a C-5 hydroxy group unit. All these saponins were evaluated for their cytotoxic activities against five selected human cancer cell lines. Among these, the known saponins 7 and 10 exhibited significant cytotoxic effects on HeLa cells with IC 50 values of 4.16 and 4.45 μM, respectively. The structure-activity relationships (SAR) of these isolates were also discussed. Flow cytometric analysis indicated that 7 could induce MDA-MB-231 cell death in a concentration-dependent manner. Saponin 7 was proved to affect the cell cycle distribution and induced G2/M phase arrest in MDA-MB-231 cells., Competing Interests: Declaration of Competing Interest The authors declare that they have no known competing financial interests or personal relationships that could have appeared to influence the work reported in this paper., (Copyright © 2020 Elsevier Inc. All rights reserved.)

Four new spirostanol saponins, named pavitnosides A-D ( 1 - 4 ), with six known steroidal saponins 5 - 10 were isolated from the rhizomes of Paris vietnamensis . Their chemical structures were determined based on extensive spectroscopic studies and chemical methods. The aglycones of pavitnoside B and pavitnoside C were not reported in previous work. The cytotoxicity of all saponins was evaluated against human glioblastoma U87MG and U251 cell lines. The new spirostanol saponin 1 displayed weak anti-proliferative activity against U87MG cell line and the known saponins 8 and 9 exhibited significant cytotoxicity against the two tumor cell lines, with IC 50 values of 2.16 to 3.14 μM, but did not affect the growth of primary cultures of human astrocytes., Competing Interests: The authors declare no conflict of interest.

Phytochemical investigation on the whole plants of Ypsilandra parviflora led to the isolation of seven new spirostanol saponins, named ypsiparosides A-G, together with 14 known saponins. Their structures were unambiguously established based on extensive spectroscopic evidence and chemical methods. The induced rabbit platelet aggregation activities of the isolates were tested. Compounds 4, 15, and 17 showed maximal platelet aggregation rates ranging from 43 to 55% at a concentration of 300μg/mL. Further experiments exhibited that compounds 4, 15, and 17 possessed EC 50 values of 642.9, 95.3, and 300.8μg/mL, respectively., (Copyright © 2017 Elsevier Inc. All rights reserved.)

Phytochemical investigation of the rhizomes of Paris polyphylla var. stenophylla led to the isolation of two new highly oxygenated spirostanol saponins, named paristenosides A (1) and B (2), together with seven known compounds. Their structures were established mainly on the base of NMR spectroscopic techniques and mass spectrometry, as well as chemical methods. In addition, the cytotoxicity of the two new saponins was tested. Two new highly oxygenated spirostanol saponins, paristenosides A (1) and B (2), were isolated from the rhizomes of Paris polyphylla var. stenophylla. Their structures were established mainly based on NMR spectroscopic techniques and mass spectrometry, as well as chemical methods.

Phytochemical investigations of the rhizome of Tupistra chinensis led to the isolation of six new spirostanol saponins, one new spirostanol, along with eight known spirostanols. Their chemical structures were elucidated on the basis of spectroscopic and chemical methods, including IR, NMR, MS, and GC analyses. The antiproliferative effects against five human cancer cell lines were assayed for all the isolated compounds. Compounds 8, 12 and 15 showed potent cytotoxic activities against K562 cells. The isolated compounds were evaluated for their inhibitory activities on nitric oxide (NO) production induced by lipopolysaccharide in a macrophage cell line RAW 264.7. Compounds 2 and 12 showed significant inhibition on NO production with IC50 values of 16.1±1.8 and 13.5±1.2 μM, respectively., (Copyright © 2016 Elsevier Inc. All rights reserved.)

Spirostanol saponins are important active components of some herb medicines, and their isolation and purification are crucial for the research and development of traditional Chinese medicines. We aimed to compare the separation of spirostanol saponins by ultra-high performance supercritical fluid chromatography (UHPSFC) and ultra-high performance liquid chromatography (UHPLC). Four groups of spirostanol saponins were separated respectively by UHPSFC and UHPLC. After optimization, UHPSFC was performed with a HSS C18 SB column or a Diol column and with methanol as the co-solvent. A BEH C18 column and mobile phase containing water (with 0.1% formic acid) and acetonitrile were used in UHPLC. We found that UHPSFC could be performed automatically and quickly. It is effective in separating the spirostanol saponins which share the same aglycone and vary in sugar chains, and is very sensitive to the number and the position of hydroxyl groups in aglycones. However, the resolution of spirostanol saponins with different aglycones and the same sugar moiety by UHPSFC was not ideal and could be resolved by UHPLC instead. UHPLC is good at differentiating the variation in aglycones, and is influenced by double bonds in aglycones. Therefore, UHPLC and UHPSFC are complementary in separating spirostanol saponins. Considering the naturally produced spirostanol saponins in herb medicines are different both in aglycones and in sugar chains, a better separation can be achieved by combination of UHPLC and UHPSFC. UHPSFC is a powerful technique for improving the resolution when UHPLC cannot resolve a mixture of spirostanol saponins and vice versa., (Copyright © 2015 Elsevier B.V. All rights reserved.)

Three new spirostanol saponins named tuberosines A-C (1-3), together with three known ones tuberoside O (4), 25(S)-Schidigera-saponin D5 (5), and shatavarin IV (6) were isolated from the roots of Allium tuberosum. Their structures were established on the basis of extensive spectroscopic analyses. Whereas compounds 5 and 6 exhibited potent antibacterial activities against Bacillus subtilis (32 μg/mL) and Escherichia coli (16 μg/mL), the new saponin 2 showed only moderate antibacterial activities against these pathogens. The relationship between the antibacterial activities and the structures of these saponins are described., (Copyright © 2015 Elsevier Inc. All rights reserved.)

Four new compounds, including three new spirostanol saponins [tupistroside G-I (1-3)] and a new flavane-O-glucoside [tupichiside A (4)], together with ten known compounds, were isolated from the fresh rhizomes of Tupistra chinensis. The structures of the new compounds were elucidated by spectroscopic analysis and chemical evidence. All compounds were tested in vitro for their cytotoxic activities against the Human LoVo and BGC-823 cell lines, and six of them were found to possess potent cytotoxicity. Compounds 2, 8 and 9 showed significant cytotoxicity against the tested tumor cell lines with IC50 values ranging from 0.2 to 0.9μM., (Copyright © 2015 Elsevier B.V. All rights reserved.)

Cells of two different cell lines:ccvx (cotyledon derived) andccvz (hypocotyl derived) ofSolanum chrysotrichum were cultivated in 10-1 airlift bioreactors for the production of the human antimycotic compound SC-1. When using 3 g l -1 dry weight inoculum in a batch culture, higher levels of biomass were achieved with theccvx cell line (14.6 g l -1 ) than withccvz (7.7 g l -1 ), resulting in 23 and 12 mg g -1 of SC-1 after 17 days in culture forccvx andccvz, respectively. The maximum productivity of SC-1 in bioreactors was 0.025 g l -1 day -1 after 9 days in culture. When using a draw-fill mode, the productivity increased by 60% to a value of 0.041 g l -1 day, 4 days after 50% of the cell suspension was removed and replaced with fresh medium. This latter bioreactor system is a feasible alternative for the production of the antimycotic metabolite ofS. chrysotrichum on a large scale.