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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.

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 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.)

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.)

Phytochemical reinvestigation on the whole plants of Ypsilandrathibetica 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. [ABSTRACT FROM AUTHOR]

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. Graphical Abstract: 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.[Figure not available: see fulltext.] [ABSTRACT FROM AUTHOR]

A new acetylated spirostanol saponin ( 7 ), dioscin-6′- O -acetate, was isolated from the rhizomes of Dioscorea althaeoides R. Knuth (Dioscoreaceae), together with fourteen known compounds, including three spirostanol saponins ( 1 – 2 , 6 ), three furostanol saponins ( 10 – 12 ), one diarylheptanoid ( 3 ), three sterols ( 4–5 , 9 ), three aliphatic acids ( 8 , 13 – 14 ) and one aliphatic alkane ( 15 ). Their structures were established by extensive 1D- and 2D- NMR (DEPT, 1 H– 1 H COSY, HSQC, HMBC and NOESY) experiments in conjunction with IR and HRESI/TOF-MS data, as well as the results of acid hydrolysis. The compounds ( 3 – 8 , 10 – 15 ) were isolated from this species for the first time. The chemotaxonomic significance of these compounds was also discussed [ABSTRACT FROM AUTHOR]

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. [ABSTRACT FROM AUTHOR]

Abstract: Phytochemical reinvestigation on the whole plants of Ypsilandra thibetica obtained five new spirostane glycosides, ypsilandrosides H-L (1–5), and a known saponin polyphylloside III (6). Among them, 1 and 2 are the first spirostane glycosides which possess novel 5(6→7) abeo-steroidal aglycones. Compounds 3 and 4 are rare saponins whose aglycones contain a hydroxyl group at C-7. Their structures were elucidated on the basis of MS, 1D and 2D NMR spectroscopic analysis and chemical evidences. The isolated compounds were evaluated for their cytotoxic activity on five tumor cell lines. [ABSTRACT FROM AUTHOR]

Abstract: A further phytochemical investigation on the whole plants of Ypsilandra thibetica yielded one sapogenin and 12 spirostanol saponins. Five of these are new compounds, designated as ypsilandrosides C-G (2–6). Their structures were determined by detailed spectroscopic analysis, including extensive 1D and 2D NMR data, and by the result of a hydrolytic reaction. Compounds 2–5 were rare steroidal saponins that an apiofuranosyl unit was directly linked at C-3 of the aglycone. Selected spirostanol saponins (2–6, 9) were tested for their cytotoxic activities against K562, SPC-A-1, BGC-823, Eca-109, and AGS cell lines. Compounds 6 and 9 showed moderate inhibitory activity against all five cell lines. The antifungal properties of the new spirostanol saponins (2–6) against Candida albicans were also determined. [Copyright &y& Elsevier]

Abstract: The chromatographic behaviour of steroidal saponins found in Anemarrhena asphodeloides, Asparagus officinalis, Convallaria majalis, Digitalis purpurea and Ruscus aculeatus was studied by HPLC–MS using a C-18 reversed-phase column and aqueous acetonitrile or aqueous methanol mobile phase gradients, with or without the addition of 1% acetic acid. The behaviour was compared to that of triterpene saponins found in Aesculus hippocastanum, Centella asiatica, Panax notoginseng and Potentilla tormentilla. Inclusion of methanol in the mobile phase under acidic conditions was found to cause furostanol saponins hydroxylated at C-22 to chromatograph as broad peaks, whereas the peak shapes of the spirostanol saponins and triterpene saponins studied remained acceptable. In aqueous methanol mobile phases without the addition of acid, furostanol saponins chromatographed with good peak shape, but each C-22 hydroxylated furostanol saponin was accompanied by a second chromatographic peak identified as its C-22 methyl ether. Methanolic extracts analysed in non-acidified aqueous acetonitrile mobile phases also resolved pairs of C-22 hydroxy and C-22 methoxy furostanol saponins. The C-22 methyl ether of deglucoruscoside was found to convert to deglucoruscoside during chromatography in acidified aqueous acetonitrile, or by dissolving in water. Poor chromatography of furostanol saponins in acidified aqueous methanol is due to the interconversion of the C-22 hydroxy and C-22 methoxy forms. It is recommended that initial analysis of saponins by HPLC–MS using a C-18 stationary phase is performed using acidified aqueous acetonitrile mobile phase gradients. The existence of naturally-occurring furostanol saponins methoxylated at C-22 can be investigated with aqueous acetonitrile mobile phases and avoiding methanol in the extraction solvent. [Copyright &y& Elsevier]

Abstract: Four steroidal saponins were isolated from the leaves of Furcraea selloa var. marginata. These included one furostanol saponin, furcreafurostatin (1), and three known spirostanol saponins, furcreastatin (3), yuccaloeside C (4) and cantalasaponin-1 (5). The 22-O-methyl ether (2) of furcreafurostatin (1) was also characterized. The structures were determined by using a combination of spectroscopic techniques. [Copyright &y& Elsevier]

The phytochemical investigation of the aerial parts of Tribulus terrestris of Bulgarian origin has resulted in the isolation of the novel furostanol saponin 1, named tribol, together with the known spirostanol saponins 2 and 3 and sitosterol glucoside. The structure of tribol was determined as (25R)-furost-5(6)-ene-3β,16,26-triol-3-O-α-rhamnopyranosyl-(1→2)-[α-rhamnopyranosyl-(1→4)]-β-glucopyranoside (1) by spectral analysis, including extensive 1D and 2D-NMR experiments. [Copyright &y& Elsevier]

The rhizomes of Tacca chantrieri have been analysed for steroidal saponin constituents, resulting in the isolation of four new spirostanol saponins (1–4), along with one known saponin (5); their structures were elucidated on the basis of extensive spectroscopic analysis, including 2D NMR, and the results of hydrolytic cleavage. The isolated compounds were evaluated for their cytotoxic activity against HL-60 human promyelocytic leukemia cells. [Copyright &y& Elsevier]