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Saponins are bioactive components of many medicinal plants, possessing complicated chemical structures and extensive pharmacological activities, but the production of high-value saponins remains challenging. In this study, a 6′- O -glucosyltransferase Pp UGT7 (Pp UGT91AH7) was functionally characterized from Paris polyphylla Smith var. y unnanensis (Franch.) Hand. -Mazz., which can transfer a glucosyl group to the C-6′ position of diosgenin-3- O -rhamnosyl-(1 → 2)-glucoside (1), pennogenin-3- O -rhamnosyl-(1 → 2)-glucoside (2), and diosgenin-3- O -glucoside (5). The K M and K cat values of Pp UGT7 towards the substrate 2 were 8.4 μM and 2 × 10−3 s−1, respectively. Through molecular docking and site-directed mutagenesis, eight residues were identified to interact with the sugar acceptor 2 and be crucial for enzyme activity. Moreover, four rare ophiopogonins and ginsenosides were obtained by combinatorial biosynthesis, including an undescribed compound ruscogenin-3- O -glucosyl-(1 → 6)-glucoside (10). Firstly, two monoglycosides 9 and 11 were generated using a known sterol 3- O - β -glucosyltransferase Pp UGT80A40 with ruscogenin (7) and 20(S)-protopanaxadiol (8) as substrates, which were further glycosylated to the corresponding diglycosides 10 and 12 under the catalysis of Pp UGT7. In addition, compounds 7 – 11 were found to show inhibitory effects on the secretion of TNF- α and IL-6 in macrophages RAW264.7. The findings provide valuable insights into the enzymatic glycosylation processes in the biosynthesis of bioactive saponins in P. polyphylla var. yunnanensis , and also serve as a reference for utilizing UDP-glycosyltransferases to construct high-value or rare saponins for development of new therapeutic agents. A 6′- O -glucosyltransferase Pp UGT7 was functionally characterized from Paris polyphylla var. yunnanensis , and four rare ophiopogonins and ginsenosides including an undescribed compound were obtained by combinatorial biosynthesis. [Display omitted] • A 6′- O -glucosyltransferase Pp UGT7 was functionally characterized from Paris polyphylla var. yunnanensis. • Two ophiopogonins and two ginsenosides, including an undescribed compound, were biosynthesized using Pp UGT7 and Pp UGT80A40. • The biosynthetic ophiopogonins and ginsenosides as well as their aglycones showed immunosuppressive activity. [ABSTRACT FROM AUTHOR]

Phytochemical investigation on aerial parts of Lysimachia atropurpurea L. (Myrsinaceae), guided by NMR methods, resulted in the isolation and characterization of three previously undescribed triterpenoid saponins named stralysaponins A-C along with five known compounds. Their structures were elucidated by 1D and 2D NMR spectroscopy and HR-ESI-MS. Stralysaponins A-C were categorized into 13 β -28-epoxyoleanane-type triterpenoid saponins, reaffirming their prevalent presence of this type in the Myrsinaceae family and the genus Lysimachia. The identified derivatives share a common four-unit branched sugar chain, with rhamnose as the terminal sugar linked at C-3 of the aglycone. The presence of triterpenoid saponins in L. atropurpurea is reported herein for the first time. This study enriched the chemical diversity of triterpenoid saponins of the genus Lysimachia. Additionally, it demonstrates the effectiveness of NMR-profiling in isolating previously undescribed triterpenoid saponins from Lysimachia spp. [Display omitted] • Three undescribed oleanane-type triterpenoid saponins from Lysimachia atropurpurea L. • First time that triterpenoid saponins were reported from Lysimachia atropurpurea L. • The structures of the undescribed compounds were determined by NMR and HRMS. [ABSTRACT FROM AUTHOR]

Panax notoginseng (Burk.) F.H. Chen is a traditional medicinal herb known as Sanqi or Tianqi in Asia and is commonly used worldwide. It is one of the main raw ingredients of Yunnan Baiyao, Fu fang dan shen di wan, and San qi shang yao pian. It is also a source of cardiotonic pill used to treat cardiovascular diseases in China, Korea, and Russia. Approximately 270 Panax notoginseng saponins have been isolated and identified as the major active components. Although the absorption and bioavailability of saponins are predominantly dependent on the gastrointestinal biotransformation capacity of an individual, minor saponins are better absorbed into the bloodstream and act as active substances than major saponins. Notably, minor saponins are absent or are present in minimal quantities under natural conditions. In this review, we focus on the strategies for the enrichment and production of minor saponins in P. notoginseng using physical, chemical, enzyme catalytic, and microbial methods. Moreover, pharmacological studies on minor saponins derived from P. notoginseng over the last decade are discussed. This review serves as a meaningful resource and guide, offering scholarly references for delving deeper into the exploration of the minor saponins in P. notoginseng. [Display omitted] • A Review on the pharmacology, transform mechanism, and structural modification of minor saponins. • The diverse structures and various biological activities of minor saponins are summarized. • The strategies for the enrichment and production of minor saponins of P. notoginseng are discussed. • Provide an experimental and theoretical basis for the research of minor saponins. [ABSTRACT FROM AUTHOR]

Phytochemical investigations of the leaves of Astragalus membranaceus (Fisch.) Bge. have led to the isolation of 12 undescribed triterpenoid saponins named huangqiyenins M–X. The structures of the undescribed compounds were determined using NMR and HRESIMS data. The cytotoxicity of these compounds against the RKO and HT-29 colon cancer cell lines was evaluated. Among these compounds, huangqiyenin W exhibited the highest cytotoxic activity against RKO colon cancer cells, whereas huangqiyenin Q and W showed moderate cytotoxic activity against HT-29 colon cancer cells. The network pharmacology results indicated that STAT3, IL-2 and CXCR1 are the correlated targets of huangqiyenin W against colon cancer, with AGE–RAGE and Th17 cell differentiation as the key signaling pathways. [Display omitted] • Twelve undescribed triterpenoid saponins were found. • Compound 11 showed preferable cytotoxic activity against RKO cells. • Compounds 1, 5 and 11 showed intermediate cytotoxic activity against HT-29 cells. • Network pharmacology predicted targets and pathways of 11 against colon cancer. [ABSTRACT FROM AUTHOR]

A total of 14 previously undescribed steroidal saponins named capsicsaponins A–N were isolated from the leaves of Solanum capsicoides , encompassing various types, including cholesterol derivatives and pseudospirostanol saponins. The structures of all compounds were determined through comprehensive analysis of spectroscopic data (1D NMR and 2D NMR), along with physicochemical analysis methods (acid hydrolysis, OR, and UV). Moreover, in the H 2 O 2 -induced pheochromocytoma cell line model, compounds 1 – 14 were screened for their neuroprotective effects on cells. The bioassay results demonstrated compounds 8 – 14 were able to revive cell viability compared to the positive control edaravone. The damage neuroprotection of the most active compound was further explored. [Display omitted] • 14 unreported steroidal saponins were isolated from Solanum capsicoides leaves. • The biological activity of 1 – 14 was screened in H 2 O 2 -induced PC-12 cells model. • Compounds 8 – 14 exhibited some degree of neuroprotective bioactivities. [ABSTRACT FROM AUTHOR]

Seven undescribed polyoxygenated ursane-type triterpenoids (vitnegundins A−G), three undescribed triterpenoid saponins (vitnegundins H−J), and 17 known ones were isolated from an EtOH extract of the aerial parts of Vitex negundo L. The structures of the undescribed compounds were established by extensive spectroscopic analysis. The absolute configurations of vitnegundins A, B, and E were determined by single-crystal X-ray diffraction data. Vitnegundins B−D are pentacyclic triterpenoids possessing rare cis -fused C/D rings and vitnegundins C–H represent undescribed ursane-type triterpenoids with 12,19-epoxy moiety. In the biological activity assay, vitnegundin A, vitnegundin E, and swinhoeic acid displayed inhibitory effects against LPS-induced NO release in BV-2 microglial cells, with IC 50 values of 11.8, 44.2, and 19.6 μM, respectively. [Display omitted] • Ten undescribed triterpenoids or triterpenoid saponins were isolated from Vitex negundo. • The absolute configurations of some undescribed triterpenoids were determined by X-ray data. • Three compounds inhibited NO release in LPS-induced BV-2 microglial cells. [ABSTRACT FROM AUTHOR]

Six undescribed triterpenoid saponins, namely aescuchinosides A-F, along with seven known triterpenoid saponins, were isolated from the seeds of Aesculus chinensis. Barrigenol-like triterpenoids (BATs) constitute these saponins. Protoaescigenin serves as their aglycone, with various oxygen-containing groups, including acetyl, isobutyryl, tigloyl, and angeloyl groups situated at C-21, C-22, and C-28. Various techniques, including 1D and 2D-NMR spectroscopy, high-resolution mass spectrometry, and acid hydrolysis, were employed to determine the structures of these compounds. The antihyperglycemic effects of the isolated compounds were examined in insulin -resistant HepG2 cells induced by palmitic acid treatment. At a concentration of 6 μM, aesculinoside F exhibited a significant increase in glucose consumption. In addition, aesculinoside F demonstrated the potential to improve insulin resistant by upregulating the PI3K/AKT pathway. These results indicate that the seeds of A.chinensis hold promising potential for preventing insulin resistant related disease. Six undescribed triterpenoid saponins, namely aescuchinosides A-F, along with seven known triterpenoid saponins were isolated from the seeds of Aesculus chinensis. [Display omitted] • Six undescribed triterpenoid saponins were isolated from the seeds of Aesculus chinensis. • Barrigenol-like triterpenoids (BATs) constitute these saponins. • Aesculinoside F demonstrated the potential to improve insulin resistant by upregulating the PI3K/AKT pathway. [ABSTRACT FROM AUTHOR]

Thirteen previously undescribed steroidal saponins, named parisverticilloside A-M (1 – 13) and twenty known steroidal saponins (14 – 33) were isolated from ethanol extract of the roots of Paris verticillata. Their structures were identified by a series of spectroscopic methods, including 1D and 2D NMR, HR-ESI-MS, optical rotatory dispersion and chemical processes. The anti-proliferative activities of all compounds against LN229, HepG2, MDA-MB-231 and 4T1 cell lines were evaluated using the CCK8 assay with cisplatin or capecitabine as the positive control. The anti-inflammatory activities of all compounds were measured by inhibition of LPS-induced NO release from BV2 cell lines, with dexamethasone as the positive control. [Display omitted] • Thirteen previously undescribed steroidal saponins were isolated from the roots of Paris verticillata. • The structures were identified by 1D and 2D NMR, HRESIMS, IR, and physical properties. • Steroidal saponins have anti-proliferative and the anti-inflammatory activities. [ABSTRACT FROM AUTHOR]

Terpenoids are the largest class of all known natural products, possessing structural diversity and numerous biological activities. Ten previously undescribed terpenoid glycosides, glechlongsides A-J (1 – 10), were isolated from the ethanol extract of the whole plant of Glechoma longituba , including diterpenoid glycoside and pentacyclic triterpenoid saponin. The structures of these compounds were characterized by extensive analysis of 1D and 2D NMR as well as HRESIMS spectra. In addition, glechlongsides F–I (6 – 9) exhibited weak cytotoxicity against human cancer cell lines BGC-823, Be1, HCT-8, A2780, and A549 with IC 50 values ranging from 3.77 to 30.95 μM, respectively. [Display omitted] • Ten undescribed terpenoid glycosides were obtained from the whole plant of Glechoma longituba. • The isolates contained seven diterpenoid glycosides and three pentacyclic triterpenoid saponins. • Their structures were determined by 1D, 2D NMR and HRESIMS spectra. • Some of compounds showed in vitro cytotoxicity against five human cancer cell lines. [ABSTRACT FROM AUTHOR]

Bioactivity-guided phytochemical fractionation of the methanol extract of Olax subscorpioidea root has led to the isolation of six triterpenes. Three of these compounds are previously undescribed triterpenoid saponins: oleanolic acid 3- O -[ α -L-rhamnopyranosyl-(1→3) -β -D-glucopyranosyl-(1 → 2)-6- O -methyl- β -D-glucuronopyranoside]-28- O - β -D-glucopyranosyl ester (2), oleanolic acid 3- O -[ β -D-glucopyranosyl-(1 → 4) -β -D-glucopyranosyl-(1 → 3)- β -D-glucopyranoside] (3), and oleanolic acid 3- O -[ β -D-glucopyranosyl-(1 → 4)-6- O -methyl- β -D-glucuronopyranoside] ester (5). Other reported known compounds include two triterpene glycosides: oleanolic acid 3- O -[ β -D-glucopyranosyl-(1 → 4)-6- O -methyl- β -D-glucuronopyranoside]-28- O - β -D-glucopyranosyl ester (1) and oleanolic acid 3- O -[ β -D-glucopyranosyl-(1 → 4)- β -D-glucuronopyranoside] (4) ; and a triterpene acid, oleanolic acid (6). The structures of these compounds were elucidated by spectroscopic means. The isolated compounds were tested against human cervical cancer (HeLa), colorectal cancer (Caco-2) and breast cancer (MCF-7) cell lines using the in vitro 3-[4,5-dimethylthiazole-2-yl] 3,5-diphenyltetrazolium bromide (MTT) assay, with vincristine as positive control. The cytotoxicity assay showed that compounds 3 and 5 exhibited significant inhibitory effects on the HeLa cell line, with IC 50 values of 7.42 ± 0.34 μM and 10.27 ± 1.26 μM; and moderate effects on MCF-7 (IC 50 values, 36.67 ± 1.23 μM and 43.83 ± 0.65 μM) and Caco-2 (IC 50 values, 35.83 ± 0.55 μM and 39.03 ± 4.38 μM, respectively) cell lines. They were also more selectively cytotoxic than vincristine against the cancer cell lines, when compared with cytotoxicity against the normal lung cell line MRC5. [Display omitted] • Methanol extract of Olax subscorpioidea root gave significant cytotoxic effects. • Six triterpenoid compounds were isolated and characterised from the active solid-phase extraction (SPE) fraction using series of preparative HPLC. • Three of the isolated triterpene glycosides have not been previously described. • All the compounds were found in this specie for the first time. • Two of the new compounds gave lower IC 50 values than the fraction. [ABSTRACT FROM AUTHOR]

For more than four centuries, the intake of Narthecium ossifragum has been associated with poisoning in domesticated animals. Saponins occurring in flowering tops of the plant are considered to cause kidney damage in calves. At present, there are more than 30 papers on the saponins of N. ossifragum in the literature, although the structures of these compounds have hitherto not been determined. Here, we identify the saponins of N. ossifragum as sarsasapogenin, sarsasapogenin-3- O - β -galactopyranoside, sarsasapogenin-3- O -(2′- O - β -glucopyranosyl- β -galactopyranoside) and sarsasapogenin-3- O -(2′- O - β -glucopyranosyl-3′- O - α -arabinopyranosyl- β -galactopyranoside). Moreover, six aromatic natural products were isolated and characterized from the methanolic extract from flowers of N. ossifragum. Five of these aromatic compounds, chrysoeriol 6- C - β -arabinofuranoside-8- C - β -glucopyranoside, chrysoeriol 6- C - β -arabinopyranosyl-8- C - β -glucopyranoside, chrysoeriol 6- C - β -xylopyranosyl-8- C - β -galactopyranoside, chrysoeriol 6- C - β -galactopyranosyl-8- C - β -glucopyranoside and chrysoeriol 6- C - β -glucopyranosyl-8- C - β -galactopyranoside are undescribed. All compounds were tested for cytotoxicity in mammalian cell lines derived from the heart, kidney, and haematological tissues. The saponins exhibited cytotoxicity in the micromolar range, with proportionally increasing cytotoxicity with increasing number of glycosyl substituents. The most potent compound was the main saponin sarsasapogenin-3- O -(2′- O - β -glucopyranosyl-3′- O - α -arabinopyranosyl- β -galactopyranoside), which produced cell death at concentrations below 3–4 μM in all three cell lines tested. This indicates that the saponins are the toxicants mainly responsible for kidney damage observed in cattle after ingestion of N. ossifragum. Our findings also pave the way for analysis of individual compounds isolated during the biopsies of intoxicated animals. Cytotoxic saponins from flowering tops of Narthecium ossifragum L. Andrea Estefanía Carpinteyro Díaz, Lars Herfindal, Bendik Auran Rathe, Kristine Yttersian Sletta, Svein Haavik and Torgils FossenCytotoxic saponins toxic to kidney cells were characterized from the hepatotoxic plant Narthecium ossifragum. Image 1 • Cytotoxic saponins of Narthecium ossifragum were for the first time identified. • Increasing cytotoxicity with increasing number of glycosyl substituents. • The main saponin was most toxic to all cell lines including kidney cells. • Five undescribed di-C-glycosylflavones were characterized. • Structures were established by 2D NMR and HRMS. [ABSTRACT FROM AUTHOR]

Phytochemical investigation of the ethyl acetate soluble part, generated from the ethanol extract of the roots of Dipsacus asper , led to the separation and identification of three undescribed triterpenoids including one arborinane type, one ursane type and one oleanane type, two unreported oleanane type triterpenoid arabinoglycosides, and 18 known analogues. Structures of these compounds were determined by comprehensive spectroscopic analyses, with the absolute configurations of 25-acetoxy-28-dehydroxyrubiarbonone E and 2 α ,3 β -dihydroxy-23-norurs-4(24),11,13(18)-trien-28-oic acid being established by evaluation of their experimental and calculated ECD spectra. 25-Acetoxy-28-dehydroxyrubiarbonone E features an oxygenated C-25 that is the first case among arborinane type triterpenoids, while 2 α ,3 β ,24-trihydroxy-23-norurs-12-en-28-oic acid incorporates a sp3 C-24 that is a rare structural feature of 23-norursane type triterpenoids. Of these isolates, 2′,4′- O -diacetyl-3- O - α - l -arabinopyranosyl-23-hydroxyolea-12-en-28-oic acid and hederagonic acid exhibited moderate antibacterial activity against Staphylococcus aureus with IC 50 values of 12.3 and 10.3 μ M, respectively, while those with either a feruloyloxy group or an arabinosyl moiety at C-3 displayed potent cytotoxic activities against four tumor cell lines A549, H157, HepG2 and MCF-7. Twenty-three compounds including five undescribed ones were isolated from the roots of Dipsacus asper and their cytotoxic evaluation with SAR discussion was presented. Image 1 • Five undescribed compounds were isolated from the roots of Dipsacus asper. • TDDFT calculations of ECD spectra were used to determine the absolute configurations. • Some compounds exhibited moderate antibacterial activities. • Some isolates displayed potent cytotoxic activities with IC 50 values below 10 μ M. • The structure-activity relationship (SAR) for cytotoxic evaluation was well discussed. [ABSTRACT FROM AUTHOR]

Abstract Polyphyllins are the major steroidal saponin components of Paris polyphylla , the main source plant of the common Chinese herbal medicine Paridis Rhizoma with strong pharmacological activity and extremely high economic value and great market prospects. However, the production of polyphyllins in plants is limited, and their biosynthesis pathway has not been reported. The downstream hydroxylation step was particularly unclear. To clarify the enzymes and intermediates involved in the downstream steps of polyphyllin biosynthesis, we performed a comparative transcriptome analysis and discovered a cytochrome P450 gene that encodes a protein with monooxygenase activity. Heterologous expression in Saccharomyces cerevisiae demonstrated that it encodes an enzyme that catalyzes the formation of 22(R)-hydroxycholesterol from cholesterol. The relative gene expression measured by RT-PCR and polyphyllin contents measured by HPLC in P. polyphylla roots at different ages confirmed that this gene is involved in polyphyllin biosynthesis. To our best knowledge, this is the first report on the cloning of a CYP450 enzyme gene from the steroidal saponin pathway of higher plants. Graphical abstract Paris polyphylla Smith var. yunnanensis (Franch.) Hara is the main source of Paridis Rhizoma, a common Chinese herbal medicine. Its major active components are steroidal saponins such as polyphyllin I, which have antitumor and immuno-stimulating properties as well as other pharmacological activities. In this study, we cloned the CYP450 gene PpCYP90B27 , which encodes an enzyme that catalyzes the formation of 22(R)-hydroxycholesterol from cholesterol. This CYP450 enzyme from P. polyphylla is responsible for the hydroxylation in the first step downstream from cholesterol in the steroidal saponin pathway, and is involved in a hitherto unknown biosynthesis pathway of bioactive ingredients polyphyllins. To our best knowledge, this is the first cloned CYP450 enzyme gene from plants in the steroidal saponin pathway. Image 1 Highlights • Gene responsible for polyphyllin biosynthesis was investigated. • PpCYP90B27 was successfully expressed in Saccharomyces cerevisiae and its catalytic products analyzed. • PpCYP90B27 was found to catalyze the conversion of cholesterol to 22(R)-hydroxycholesterol. [ABSTRACT FROM AUTHOR]

Abstract Triterpenoid saponins are specialized metabolites, which are abundant in soybean seeds. They have a wide variety of effects on human health and physiology. The composition of sugar chain attached to the aglycone moiety of saponins can be controlled by genetic loci, such as Sg-1 , 3 , and 4. Among these, the homozygous recessive sg-4 impairs the accumulation of saponins that have an arabinose moiety at the second position of the C-3 sugar chain (i.e., saponins Ad and βa) in the hypocotyls. In this study, we found that sg-4 cultivars are disabled in Glyma.01G046300 expression in hypocotyls. This gene encodes a putative glycosyltransferase (UGT73P10) and is a homolog of GmSGT2 (UGT73P2) whose recombinant protein has been previously shown, in vitro , to conjugate the second galactose moiety at the C-3 position of soyasapogenol B monoglucuronide (SBMG). The sg-4 phenotype (absence of saponins Ad and βa in hypocotyls) was restored by introducing the Glyma.01G046300 genomic DNA fragment that was obtained from the Sg-4 cultivar 'Ibarakimame 7'. Although Glyma.01G046300 is expressed in the cotyledons even in the sg-4 cultivars such as 'Enrei', the induced premature stop codon mutation (W244*) resulted in impaired accumulation of saponin βa in this tissue also in the 'Enrei' genetic background. Furthermore, the recombinant Glyma.01G046300 protein was shown to conjugate the second Ara moiety at the C-3 position of SBMG using UDP-Ara as a sugar donor. These results demonstrate that Sg-4 is responsible for conjugation of the second Ara moiety at the C-3 position of soybean saponins. Graphical abstract Image 1 Highlights • The sg-4 allele in soybean impairs the accumulation of specific saponins. • Evidence that Glyma.01G046300 is responsible for the sg-4 phenotype is provided. • Sg-4 (Glyma.01G046300) encodes a UDP-arabinose glycosyltransferase. [ABSTRACT FROM AUTHOR]

Abstract To search for bioactive gypenosides and their analogues, a saponin enriched fraction and its hydrolyzate from Gynostemma pentaphyllum were phytochemically investigated. Fractionation by diverse chromatographic methods, including HPLC, Sephadex LH-20, silica gel, and C18 reverse phase silica gel, led to the isolation and purification of twelve triterpenes, including five undescribed and seven known. The chemical structures of all compounds were determined as analyzed by nuclear magnetic resonance (NMR), high resolution mass spectrometry (HR-MS), infrared spectrum (IR), optical rotation, and chemical transformations. Among all isolates, nine compounds possessed a rare dammarane triterpenoid framework with A-ring modified. The relative configurations of three compounds were determined by 2D NMR for the first time. The absolute configurations of four compounds were determined by the modified Mosher's method. Two of all isolated compounds significantly enhanced 2-deoxy-2-[(7-nitro-2,1,3-benzoxadiazol-4-yl)amino]-D-glucose (2-NBDG) uptake and Glucose Transporter 4 (GLUT4) translocation via activating the AMP-activated protein kinase (AMPK) and acetyl-CoA carboxylase (ACC) signaling pathway. This study provided the potential candidates for the development of antidiabetic agents. Graphical abstract Five undescribed and nine known triterpenes were isolated from the hydrolyzate and extract of Gynostemma pentaphyllum. Their hypoglycemic activity was evaluated. Image 1 Highlights • Gynostemma pentaphyllum is a traditional medicinal and edible plant in China. • Five undescribed triterpenes were isolated. • The modified Mosher's method was used to determine the absolute configurations. • Their hypoglycemic activity was evaluated in differentiated 3T3-L1 adipocytes. • This study provided the potential candidates for antidiabetic agents. [ABSTRACT FROM AUTHOR]

Herein, five undescribed oleanane-type triterpenoid saponins, namely, psammosaponins A–E, along with nine known compounds, were isolated from the roots of Psammosilene tunicoides. Moreover, part of the ethanolic extract of P. tunicoides was acid-hydrolyzed and three aglycones were isolated from the resulting hydrolysate. The structures of all compounds were established through extensive analysis involving 1D and 2D NMR experiments, HRESIMS measurements, chemical derivatization, and comparison of spectroscopic data with the values reported in the literature. In all, 10 of the isolated saponins and the three aglycones were evaluated in the acetic acid-induced writhing model for their antinociceptive activity. At a dose of 40 mg/kg, these compounds exhibited significant inhibitory effects on the mouse writhing response, with inhibitions ranging from 31.9% to 79.3%. In addition, the structure–activity relationships of the isolates were discussed. Among the isolates, quillaic acid 3- O -glucuronide and 16α-hydroxygypsogenic acid showed better antinociceptive activity with inhibitions of 79.3% and 73.7%, respectively. Both isolates also exhibited antinociceptive activities in hot plate and formalin tests on mice. Their antinociceptive mechanism was explored in lipopolysaccharide–stimulated RAW 264.7 cells. These isolates could significantly inhibit the production of nitric oxide and interleukin-6 and downregulate the expression levels of inducible NO synthase, COX-1, and COX-2. Fourteen oleanane-type triterpenoid saponins including five undescribed triterpenoid saponins, psammosaponins A–E, were isolated from Psammosilene tunicoides , and three aglycones were obtained by hydrolysis of its ethanolic extract. Some of them showed significant antinociceptive activity. [Display omitted] • Five undescribed oleanane-triterpenoid saponins were isolated from Psammosilene tunicoides. • 13 isolated compounds exhibited antinociceptive activity with high inhibitions, up to 79.3%. • Two compounds could effectively inhibit the production of COX-1, iNOS, and IL-6. [ABSTRACT FROM AUTHOR]

The genus Polygonatum Mill. belongs to the Liliaceae family, which is widely distributed all over the world. Modern studies have found that Polygonatum plants are very rich in chemical compounds such as saponins, polysaccharides and flavonoids. Steroidal saponins are the most commonly studied saponins in the genus Polygonatum and a total of 156 compounds have been isolated from 10 species of the genus. These molecules possess antitumor, immunoregulatory, anti-inflammatory, antibacterial, antiviral, hypoglycemic, lipid-lowering and anti-osteoporotic activities. In this review, we summarize recent advances in studies of the chemical constituents of steroidal saponins from Polygonatum , including their structural characteristics, possible biosynthetic pathways and pharmacological effects. Then , the relationship between the structure and some physiological activities is considered. This review aims to provide reference for further exploitation and utilization of the genus Polygonatum. The structures, biosynthesis, and pharmacological effects of 156 steroidal saponins isolated from the genus Polygonatum are covered. [Display omitted] • Steroid saponins from Polygonatum have several potential pharmaceutical applications. • The structures and structural characteristics of these compounds are summarized. • The biosynthetic pathway of steroid saponins in Polygonatum is summarized. • The structure-activity relationship among Polygonatum steroid saponins is described. [ABSTRACT FROM AUTHOR]

The importance of mitochondria in regulation of aging has been extensively recognized and confirmed. Gynostemma pentaphyllum (Thunb.) Makino, a homology of medicine and food, has been widely utilized as dietary supplement. In this study, the transcriptome of normal cells (wild type mouse embryo fibroblasts) regulated by the 30% aqueous EtOH extract of G. pentaphyllum was firstly evaluated by RNA sequencing and the results revealed that the G. pentaphyllum could up-regulate the genes involved in oxidative phosphorylation (OXPHOS) and sirtuin (SIRT) signaling pathways, indicating its effect in promoting cell viability might be attributed to the role of improving mitochondrial functions. To further discover the bioactive compounds, sixteen undescribed dammarane-type saponins along with twenty-eight known analogues were isolated from the active extract of G. pentaphyllum. Their structures were elucidated by means of comprehensive analysis of NMR and HRMS spectroscopic data. All isolates were evaluated for the regulatory effects on SIRT3 and translocase of the outer membrane 20 (TOM20), and thirteen of them exhibited satisfactory agonist activities on both SIRT3 and TOM20 at 5 μM. Furthermore, the preliminary structure-activity relationships analysis demonstrated the additional hydroxymethyl and carbonyl groups or less sugar residues in saponins could contribute positively to the up-regulatory effect on SIRT3 and TOM20. These findings encouraged the potential roles of G. pentaphyllum and its bioactive saponins in the development of natural drugs for the treatment of aging-related diseases. Forty-four dammarane-type saponins including 16 undescribed ones were isolated from Gynostemma pentaphyllum. Thirteen compounds could up-regulate the expressions of both SIRT3 and TOM20 proteins. [Display omitted] • pentaphyllum possessed anti-aging activity by regulating OXPHOS and SIRT pathways. • Sixteen undescribed dammarane-type saponins were isolated from G. pentaphyllum. • Thirteen compounds exhibited agonist activities on both SIRT3 and TOM20. • The structure-activity relationships were preliminarily concluded. [ABSTRACT FROM AUTHOR]

Three unique hydroxybutyrate-containing triterpenoid saponins, angustiside A–C (1 – 3), were isolated from the shoots of Brachyscome angustifolia (Asteraceae). The extensive spectroscopic study showed that their aglycone is a previously undescribed one, 16-hydroxy olean-18-en-28-oic acid, named as angustic acid (1a), and 2 and 3 contain hydroxybutyrate moiety in their side chains. The absolute configuration of 1a was determined to be (3R , 5R , 9R , 13S , 16S) by X-ray crystallography. The immunity assay revealed that 2 and 3 containing both acyl chains and branched saccharides significantly enhanced the proliferation of OT-I CD8+ T cells and secretion of interferon gamma (IFN-γ), presenting their immunogenic activity. [Display omitted] • Structurally novel C 30 -triterpenoid saponins from B. angustifolia were identified. • Absolute configuration was confirmed with X-ray crystallography, and cysteine and PGME reactions. • Angustiside B and C (2 and 3) showed immunogenic activity by inducing OT-I CD8+ T cells and IFN-γ response. [ABSTRACT FROM AUTHOR]

Camellia sinensis L. (Theaceae) leaves have been used as a beverage in both Eastern and Western cultures for a long time, while its root has not been intensively studied. In this study, seven undescribed triterpenoid saponins (1 – 7) and twelve known saponins (8 – 19) with different combinations of substituents, such as oxygenated isoprenyl substituents and sugar moieties, and lengths of sugar chains, were isolated from the C. sinensis roots. Their structures were unequivocally determined using one- and two-dimensional nuclear magnetic resonance data and acid hydrolysis analysis. Investigation of the biological activities of isolated compounds revealed that only those without functional acetyl groups exhibited cytotoxic activities against mouse and human cancer cells (B16F10) and human cervical cancer cell line (HeLa) at 50 μM. Compounds with an aldehyde group at C-23 of aglycone showed immunomodulatory activity against Th1 and Th17 cells at 10 μM. Ten compounds with biological activities from C. sinensis roots extracts, including three previously undescribed ones (3 , 6 , and 7), were identified. Seven undescribed triterpenoid saponins (1 – 7) and twelve known saponins (8 – 19) with different combinations of substituents were isolated from the C. sinensis roots. The presence of an aldehyde group at C-23 of aglycone may impact the differential immunomodulatory activity against Th1 and Th17 cells. [Display omitted] • Seven undescribed triterpenoid saponins were gained from Camellia sinensis roots. • Their structures were determined using 1D (1H and 13C), 2D (HSQC, COSY, and HMBC) NMR and HR-ESI-MS analyses. • The biological activity (cytotoxic activities and immunomodulatory activities) of saponins isolated from C. sinensis roots were investigated. [ABSTRACT FROM AUTHOR]

Phytochemical investigations of the aerial parts of the plant Cephalaria taurica Szabó. (Caprifoliaceae) have resulted in the isolation of nine oleanane-type triterpenoid saponins, of which two still remain undescribed. The structures of tauricosides A and B were characterized based on NMR analysis, HRESIMS spectrometry, and chemical evaluations. The saponins tauricosides A and B have been rarely reported in the literature due to the presence of eight sugar moieties, and this is also the first report of saponins containing eight sugar moieties in the Caprifoliaceae family. The cytotoxic activities of tauricosides A and B, their undescribed prosapogenins, aglycone hederagenin, and n -butanol extract of C. taurica against the cancerous cells A-549, HeLa, PANC-1, and SH-SY5Y and the noncancerous HEK-293 cells were evaluated by the MTT method. Although tauricosides A and B and the crude n -butanol extract did not exhibit any activity at the tested concentrations on all the tested cells, after alkaline hydrolysis, the cytotoxic activity potential of the compounds was obviously improved. The most active compound, obtained after the alkaline hydrolysis of tauricoside B, showed a significant inhibitory effect, which was higher than that of the standard, commercially available drug doxorubicin, on the cancerous A-549, HeLa, PANC-1, and SH-SY5Y cells with IC 50 values of 9.04, 8.75, 6.87, and 4.32 μM, respectively. In addition, prosapogenin, obtained after the alkaline hydrolysis of tauricoside A, exhibited considerable cytotoxic activity on the cancerous A-549, HeLa, PANC-1, and SH-SY5Y cells, with IC 50 values of 13.19, 10.32, 11.91, and 7.49 μM, respectively. In conclusion, the alkaline hydrolysis of the saponins (tauricosides A and B) obviously improved their cytotoxic activity potential. [ABSTRACT FROM AUTHOR]

Six undescribed pentacyclic triterpenoids including four triterpenoid aglycones, 1 β ,2 a ,3 β ,23-tetrahydroxyurs-12-en-28-ursolic acid, 2 a ,3 a ,6 β ,19 α ,23-pentahydroxyurs-12-en-28-ursolic acid, 2 α ,3 α ,20 β ,23-tetrahydroxyurs-12-en-28-ursolic acid and 1 β ,2 a ,3 β ,23-tetrahydroxyurs-12,20(30)-dien-28-ursolic acid, and two triterpenoid glucosides, 2 a ,3 a ,23-trihydroxy-12,20(30)-dien-28-ursolic acid 28- O - β - d -glucopyranoside and 1-oxo-3 β ,23-dihydroxyolean-12-en-28-oic acid 28- O - β - d -xylopyranoside, along with 5 known triterpenoids were isolated from a CH 3 Cl-soluble extract of the leaves of Cyclocarya paliurus . Their structures were established on the basis of chemical and spectroscopic approaches. These compounds were assessed for their antioxidant effects on FFA-induced hepatic steatosis in HepG2 cells. The results revealed that three saponins and two aglycones markedly increased SOD activity and reduced MDA level. [ABSTRACT FROM AUTHOR]

Seven dammarane-type saponins previously undescribed (notoginsenosides Fh1-Fh7) were isolated from the aqueous extract leaves of Panax notoginseng (Burk.) F.H.Chen (Araliaceae), together with eleven known saponins. Their structures of were elucidated by spectroscopic analysis (NMR, UV, IR, ect. ), HR-ESI-MS techniques and chemical methods. Screening results indicated that compounds 4 , 5 , 12 , 13 showed moderate neuroprotective effects on H 2 O 2 -induced cellular damage in human neuroblastoma SH-SY5Y cells (10 μM). [ABSTRACT FROM AUTHOR]

Phytochemical studies on the barks of Ilex rotunda Thunb. had resulted in the isolation of seven previously undescribed triterpenoids, rotundinosides E-K, along with sixteen known ones. The structures of previously undescribed compounds were elucidated on the basis of extensive spectroscopic analysis and the sugar moieties were further identified by HPLC and GC after acid hydrolysis. Among the isolates, rotundinoside F featured a rare triterpene-phenylpropanoid hybrid structure and rotundinoside H was an uncommon triterpene saponin with α-linked glucopyranosyl moiety at C-3. The antiplatelet aggregation of all compounds were evaluated against ADP induced rat platelet aggregation in vitro , and five compounds exhibited moderate inhibitory effects with IC 50 values ranging from 22.4 to 32.8 μM. [ABSTRACT FROM AUTHOR]

In a study of 62 plant species of the Cretan flora for their phytotoxic activity, plants were extracted successively with CH 2 Cl 2 , MeOH and H 2 O. Phytotoxicity evaluation of the 240 extracts was performed against Lactuca sativa L. and Agrostis stolonifera L.. The MeOH extract of Bellis longifolia was the most phytotoxic. Bioassay-guided fractionation revealed that a fraction consisting mainly of saponins was the most effective. Separation of the saponins was performed using initially a step-gradient Centrifugal Partition Chromatography (CPC). Investigation of the active fraction led to the isolation and structure elucidation of three previously undescribed triterpene saponins, 3-O-β-D-fucopyranosyl polygalacic acid , 28-O-α-L-rhamnopyranosyl-(1 → 2)-β-D-fucopyranosyl polygalacic acid and 3-O-β-D-fucopyranosyl-2α,3β,23-trihydroxyolean-12-en-28-oic acid , which were present as the main phytotoxic compounds of the methanol extract. Two triterpenes, polygalacic acid and bellisonic acid and four kaempferol glucosides, as well as chlorogenic acid were also isolated. 3-O-β-D-fucopyranosyl polygalacic acid and 3-O-β-D-fucopyranosyl-2α,3β,23-trihydroxyolean-12-en-28-oic acid had phytotoxic activity similar to some commercial herbicides (IC 50 values of ca. 25 μM) against duckweed ( Lemna paucicostata ). [ABSTRACT FROM AUTHOR]

Five previously undescribed bisdesmosidic triterpenoid saponins named calendustellatosides A-E, along with fifteen known compounds were isolated from the 70% ethanol whole plant extract of Calendula stellata Cav. (Asteraceae). Their structures were determined by 1D- and 2D-NMR spectroscopy as well as high resolution mass spectrometry and acid hydrolysis. The saponins comprised oleanolic acid, echinocystic acid, morolic acid or mesembryanthemoidigenic acid as the aglycones and saccharide moieties at C-3 and C-28. Like most Calendula saponins, the sugar moiety linked at C-3 was either β - d -glucose or β - d -glucuronic acid which could be substituted at C-3 by a β - d -galactose and/or C-2 by a supplementary β - d -galactose or a β - d -glucose. The sugar moiety linked to C-28 was determined as β - d -glucose. The antibacterial evaluation of compounds 1 – 20 by bioautography on Staphylococcus aureus followed by the determination of MIC values of active compounds by serial dilution technique against 5 bacteria revealed that; calendustellatoside D was the most active against Enterococcus faecalis with an antibacterial effect comparable to antibiotics. The cytotoxic activities of isolated compounds were evaluated against fibrosarcoma cell line (HT1080) and human lung cancer cell line (A549). Calendustellatosides B and D exhibited a low cytotoxic activity against HT1080 cell line with IC 50 values of 47 ± 0.6 and 39 ± 0.5 μM, respectively. [ABSTRACT FROM AUTHOR]

Gynostemma pentaphyllum is a popular functional food, and it is also used as a traditional medicine in Asia. In this study, five previously undescribed triterpenes, gypensapogenin M, gypensapogenin N, gypensapogenin O, gypensapogenin P, and gypensapogenin Q, together with five known compounds were isolated from the hydrolyzate of total G. pentaphyllum saponins. The bioassay data showed that all the triterpenes exhibited significant protective activity against H 2 O 2 -induced myocardial cell injury and anti-hepatic fibrosis activity. Taken together, the discovery of these triterpenes from the hydrolyzate of total G. pentaphyllum saponins expands its use as a functional food for preventing myocardial injury and liver fibrosis. [ABSTRACT FROM AUTHOR]

The genus Primula is the largest among the Primulaceae and is widespread mainly in the cold and temperate regions of the Northern Hemisphere. Since the beginning of the Twentieth century, several studies on the phytochemical composition of different species of Primula have been carried out. The main constituents examined were tissue and epicuticular flavonoids and saponins, which are of therapeutic significance. Only in recent years studies of the volatiles emitted by leaves and flowers have been carried out as well, but they are restricted to a small number of species. Only a few authors have documented the morphology and function of glandular trichomes in relation to the production of flavonoids and volatile organic compounds (VOCs). The use of Primula in folk medicine is described in the literature. Investigation of the biological and pharmacological activities of Primula are reported. This study aims at providing a collection of publications on the genus Primula along with a critical revision of literature data. It focuses on the possible taxonomic significance of the secondary metabolites and on their ecological role as attractors for pollinators and deterrents against herbivores and parasites, in order to build the base for further studies. [ABSTRACT FROM AUTHOR]

Phytochemical investigations of the roots of Spergularia marginata had led to the isolation of four previously undescribed triterpenoid saponins, a known one and one spinasterol glycoside. Their structures were established by extensive NMR and mass spectroscopic techniques as 3- O -β-D-glucuronopyranosyl echinocystic acid 28- O -α-L-arabinopyranosyl-(1 → 2)-α-L-rhamnopyranosyl-(1 → 3)-β-D-xylopyranosyl-(1 → 4)-α-L-rhamnopyranosyl-(1 → 2)-α-L- arabinopyranosyl ester, 3- O -β-D-glucopyranosyl-(1 → 3)-β-D-glucuronopyranosyl echinocystic acid 28- O -α-L-arabinopyranosyl-(1 → 2)-α-L-rhamnopyranosyl-(1 → 3)-β-D-xylopyranosyl-(1 → 4)-α-L-rhamnopyranosyl-(1 → 2)- α-L-arabinopyranosyl ester, 3- O -β-D-glucopyranosyl-(1 → 4)-3- O -sulfate-β-D-glucuronopyranosyl echinocystic acid 28- O -α-L-arabinopyranosyl-(1 → 2)-α-L-rhamnopyranosyl-(1 → 3)-β-D-xylopyranosyl-(1 → 4)-α-L-rhamnopyranosyl-(1 → 2)-α-L-arabinopyranosyl ester, and 3- O -β-D-glucopyranosyl-(1 → 4)-β-D-glucuronopyranosyl 21- O -acetyl acacic acid. Their cytotoxicity was evaluated against two human cancer cell lines SW480 and MCF-7. The most active compound showed a cytotoxicity with IC 50 14.2 ± 0.8 μ M (SW480), and 18.7 ± 0.8 μ M (MCF-7), respectively. [ABSTRACT FROM AUTHOR]

Artefact compounds obtained during acid hydrolysis of saponins from Medicago spp. (Fabaceae), have been monitored and evaluated by GC-FID. Their identification has been performed by GC-MS and 1 H and 13 C NMR. Saponins with different substituents on the triterpenic pentacyclic aglycones were considered, and their hydrolysis products were detected and quantified during 10 h of time course reaction. From soyasapogenol B glycoside the well known soyasapogenols B, C, D and F were obtained together with a previously undescribed sapogenol artefact identified as 3 β ,22 β ,24-trihydroxyolean-18(19)-en and named soyasapogenol H. From a zanhic acid saponin two major artefact compounds identified as 2 β ,3 β ,16 α -trihydroxyolean-13(18)-en-23,28-dioic acid and 2 β ,3 β ,16 α -trihydroxyolean-28,13 β -olide-23-oic acid were obtained, together with some zanhic acid. Other compounds, detected in very small amount in the reaction mixture, were also tentatively identified based on their GC-MS and UV spectra. The other most characteristic saponins in Medicago spp., hederagenin, bayogenin and medicagenic acid glycosides, under acidic condition of hydrolysis, released instead the correspondent aglycones and generated a negligible amount of artefacts. Nature of artefacts and mechanism of their formation, involving a stable tertiary carbocation, is here proposed and discussed for the first time. [ABSTRACT FROM AUTHOR]

Phytochemical profiling of Ziziphus spina-christi leaves led to the characterization of 10 dammarane-type saponins and 12 phenolic compounds. Isolation was achieved by gel chromatography on Sephadex LH20, open column chromatography on silica gel, and semi-preparative HPLC with PDA and ELSD detectors. Structural characterization was performed by extensive 1D and 2D NMR, mass spectrometry, and by GC-MS of sugar derivatives. A biosynthetic pathway leading to three previously undescribed sapogenins is proposed. The saponin profiles in Z. spina-christi leaves of four different origins were compared by means of HPLC-ESIMS. [ABSTRACT FROM AUTHOR]

Phytochemical investigation of the tubers of Ophiopogon japonicus led to the isolation of five previously undescribed steroidal saponins, ophiojaponins A–E, together with twelve known ones. The structures of these isolated compounds were elucidated by detailed spectroscopic analyses and chemical methods. Ophiojaponins A–C are rare naturally occurring C 29 steroidal glycosides possessing a homo-cholestane skeleton with an aromatized ring E. Ruscogenin 1- O - α -L-rhamnopyranosyl-(1 → 2)-4- O -sulfo- β -D-fucopyranosido-3- O - β -D-glucopyranoside was isolated as single component and its full spectroscopic data was reported for the first time. The isolated steroidal saponins were evaluated for their cytotoxicities against two human tumor cell lines MG-63 and SNU387. Among them, five known spirostane-type glycosides showed cytotoxic activity against both MG-63 and SNU387 cell lines with IC 50 values ranging from 0.76 to 27.0 μM. [ABSTRACT FROM AUTHOR]

Seven previously undescribed bidesmosidic triterpenoid saponins named albidosides A – G, were isolated from a methanol extract of the roots of Acacia albida . Their structures were elucidated using 1D and 2D NMR spectroscopy and mass spectrometry and determined to be bidesmosides of oleanolic acid and of 16α-hydroxyoleanolic acid. Albidosides B – G were assayed for their cytotoxicity against HeLa and HL60 cells using MTT method and microscopic observation. [ABSTRACT FROM AUTHOR]

Siberian ginseng ( Eleutherococcus senticosus ) is a woody medical shrub belonging to the Araliaceae family. E. senticosus contains various types of saponins, including oleanane, noroleanane, lupane, and 3,4-secolupane types, depending on the aglycone structure. Oleanane-type triterpenes are the major saponin components in E. senticosus . Two enzymes (β-amyrin synthase and β - amyrin 28 - oxidase) are essential for oleanane-type saponin biosynthesis from 2,3-oxidosqualene. In the present study, two full-length cDNAs encoding EsBAS and CYP716A244 were isolated based on transcriptomics analysis of plant leaves. Both β-amyrin synthase (EsBAS) and β - amyrin 28 - oxidase (CYP716A244), isolated from E. senticosus, were functionally characterised. β-amyrin production was confirmed by heterologous expression of the EsBAS gene in yeast and tobacco. Oleanolic acid production was confirmed by co-expression of both EsBAS and CYP716A244 in engineered yeast and transgenic tobacco. [ABSTRACT FROM AUTHOR]

Chemical constituent investigation on the n -BuOH extract of the rhizomes of Tupistra chinensis Baker leads to the isolation of ten compounds including eight undescribed furostanol saponins, tupischinosides A − H, and two known ones. The structures of isolated compounds were determined by extensive spectral analysis and chemical evidences. Interestingly, tupischinosides A and B, C and D, E and F, G and H were identified as four pairs of epimers. The cytotoxicity of tupischinosides A − H against human cancer cell lines U87, SHG44, U251, LN229 and HepG-2 was evaluated by CCK-8 method. As a result, tupischinosides A and C exhibited significant proliferation inhibitory effect on the tested cancer cells. On the contrary, the corresponding epimers, tupischinosides B and D, which only differ in the configuration of C-23 didn't exhibit any cytotoxicity to cancer cells. These results indicated that the stereochemistry of C-23 was crucial to the activity of the compounds. Eight undescribed furostanol saponins along with two known ones were isolated from the rhizomes of Tupistra chinensis Baker. The cytotoxicity against human cancer cell lines U87, SHG44, U251, LN229 and HepG-2 was evaluated. [Display omitted] • Eight undescribed furostanol saponins were isolated from the rhizomes of Tupistra chinensis. • Tupischinosides A – H were identified as four pairs of epimers. • The configuration of the substituent at C-23 of the side chain was determined. • The cytotoxicity between the epimers tupischinosides A and B, C and D was totally different. [ABSTRACT FROM AUTHOR]

Paris polyphylla var. yunnanensis (Franch.) Hand.-Mazz. (Melanthiaceae), an important specie of the genus Paris, has long been in a traditional Chinese medicine (TCM) for a long time. This study aimed to isolate and identify the structures of bioactive saponins from the rhizomes of P. polyphylla var. yunnanensis and evaluate their cytotoxicity against BxPC-3, HepG2, U373 and SGC-7901 carcinoma cell lines. Seven previously undescribed and seven known saponins were identified, and Paris saponins VII (PSVII) showed significant cytotoxicity against the BxPC-3 cell line with IC 50 values of 3.59 μM. Furthermore, flow cytometry, transmission electron microscopy and western-bolt analysis revealed that PSVII inhibited the proliferation of BxPC-3 cells and might be involved in inducing apoptosis and pyroptosis by activating caspase-3, -7 and caspase-1, respectively. [Display omitted] • Seven undescribed saponins were isolated from the rhizomes of Paris polyphylla var. yunnnanensis. • The cytotoxicities of all isolated compounds against several cancer cell lines were evaluated. • Paris saponin VII inhibits the proliferation of BxPC-3 cells by inducing apoptosis and pyroptosis. [ABSTRACT FROM AUTHOR]

The chemical components and availability of Paris rugosa were investigated for the first time, using a UPLC–MS/MS-based molecular networking strategy and phytochemical research. Ultimately, eleven undescribed steroidal saponins, parisrugosides A–K, and ten known analogs were identified. Their structures were confirmed using comprehensive spectroscopic data and chemical methods. The aglycones of parisrugosides A–D are first spirostanes with an epoxy group at C-5/C-6, a hydroxy group at C-7, and a double bond at C-8/C-9 or C-8/C-14. Parisrugosides G and H possess an undescribed spirostane aglycone with two double bonds located at C-5/C-6 and C-8/C-9, which are conjugated with a carbonyl group at C-7. The isolates were evaluated for their cytotoxicity against five human cancer cell lines (human HL-60 leukemia, A549 lung, MCF-7 breast, SMMC-7721 liver, and SW480 colon solid cancer cell lines). Parisyunnanoside D, kingianoside K, and dichotomin displayed significant cytotoxicity against these cancer lines, with IC 50 values ranging from 0.50 to 19.58 μM. Eleven undescribed steroidal saponins, parisrugosides A–K, were obtained from Paris rugosa using UPLC-MS/MS-based molecular networking strategy and phytochemical research.▪ • The chemical components of Paris rugosa were investigated for the first time. • Eleven undescribed saponins were isolated under the guidance of MS/MS molecular networking technology. • The aglycones of parisrugosides A–D and parisrugosides G–H are firstly reported. • Parisyunnanoside D, kingianoside K, and dichotomin showed significant cytotoxicities against five human cancer cell lines. [ABSTRACT FROM AUTHOR]

The husks of Xanthoceras sorbifolia Bunge were explored resulting in the isolation of nine undescribed compounds and seven known compounds. Their structures were defined by NMR spectroscopic techniques, HRESIMS analyses and DP4+ possibility analysis. Three of them showed evident inhibition on NO productions in LPS-induced BV-2 cells by controlling the expression of the nuclear factor-kappa-B (NF- κ B) signaling pathway. Furthermore, they also markedly decreased the expression of the proteins COX-2 and iNOS. In addition, most compounds showed no cytotoxicity against Hep 3B, A549, HCT 116, AGS, MCF-7 cell lines. These findings showed that the husks of X. sorbifolia might have considerable potential for the prevention of inflammation-related neurodegenerative disorders. Three of nine undescribed barrigenol triterpenoid saponins showed evident inhibition on NO productions in LPS-induced BV-2 cells by controlling the expression of the nuclear factor-kappa-B (NF-κB) signaling pathway and decreasing the expression of the proteins COX-2 and iNOS. [Display omitted] • Nine undescribed triterpenoid saponins were gained from Xanthoceras sorbifolia. • Two saponins contain a rare C-15 mono-oxygenation moiety or an ester group at C-28. • Three showed evident inhibition effects of NO release by LPS-induced BV-2 cells. • Their anti-inflammatory mechanism may be related to NF- κ B signaling pathway. [ABSTRACT FROM AUTHOR]

Twelve oleanane saponins, zebiriosides A-L, were isolated from the roots of Dendrobangia boliviana Rusby, together with two known saponins, talunùmoside I and 3- O -β- d -glucuronopyranosyl serjanic acid. These saponins are glycosides of serjanic or phytolaccinic acid. Their structures were established on two basis: first, their spectral data, mainly HR-TOFESIMS, 1D-NMR ( 1 H, 13 C, DEPT) and 2D-NMR ( 1 H 1 H COSY, TOCSY, HSQC, HMBC, and ROESY), and second by comparison with literature data. These compounds were evaluated for their cytotoxic, antileishmanial and hemolytic activities. No antileishmanial or hemolytic activities were revealed, however zebirioside C and zebirioside I showed cytotoxicity against fibroblasts with IC 50 of 6.4 and 5.6 μM, respectively. [ABSTRACT FROM AUTHOR]

The genus Agave comprises more than 400 species with geographical presence in the tropical and sub-tropical regions of the world. These plants have a rich history of folkloric use and are known for a wide spectrum of applications. Secondary metabolites of diverse chemical classes have been reported from Agave species. Owing to their pharmacological significance, the steroidal saponins of Agave have caught the attention of phytochemists, biologists and drug discovery scientists. The present review describes 141 steroidal saponins and sapogenins and covers the literature published from 1970 to 2015. It is a comprehensive and coherent presentation of the structures, methods of chemical profiling, structure elucidation and biological activities of the saponins and sapogenins reported from Agave . The article provides a perspective of the research on steroidal compounds of Agave . [ABSTRACT FROM AUTHOR]

Ginsenosides produced by ginseng ( Panax quinquefolius L.) are mildly fungitoxic saponins; however, exposure of the ginseng root pathogen Pythium irregulare Buisman to ginsenosides enhances its growth in a dose dependent manner, leading to speculation that ginsenosides may function as chemoattractants and/or growth regulators in the context of the ginseng – P. irregulare pathosystem. In the present work, it was demonstrated that the treatment of ginseng plants with a relatively high dose of ginsenosides by dipping their roots into a solution of ginsenosides prior to planting results in delayed infection by P. irregulare in pot experiments, as monitored by non-invasive chlorophyll fluorescence imaging. In an attempt to determine whether this observation results from a protective effect of the ginsenosides, or from a modification of P. irregulare growth habit in response to ginsenosides present in the soil, standard in vitro disk diffusion assays were conducted. Here, exposure of P. irregulare to crude ginsenosides or pure ginsenoside Rb1, resulted in delayed hyphal progression, while enhancing aerial hyphae build-up around ginsenoside-treated disks. By contrast, assays with pure ginsenoside F2 resulted in clear zones of inhibition around treated disks. While it remains unclear whether ginsenosides act as chemoattractants for P. irregulare in vivo , the results here suggest that these saponins serve to alter the growth habit of this organism, both in vivo and in vitro . [ABSTRACT FROM AUTHOR]

Phytochemical investigation of the stems and leaves of Paris polyphylla var. yunnanensis led to isolation of 12 steroidal saponins, chonglouosides SL-9–SL-20, which had not been described previously, along with 13 known compounds. Their structures were established on the basis of extensive spectroscopic analysis and chemical methods. Four of the twelve steroidal saponins possessed three steroidal aglycones which have not been reported in nature. Steroidal saponins were also evaluated for their cytotoxicities against two human cancer cell lines (HepG2 and HEK293) and anti-HCV effects. One known steroidal saponin was the most cytotoxic compound overall with IC 50 values of 2.9 ± 0.5 μM and 5.0 ± 0.6 μM against HepG2 and HEK293 cell lines, respectively, while none showed anti-HCV activity at a concentration of 20 μM. [ABSTRACT FROM AUTHOR]