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Paris polyphylla is an important traditional medicinal plant of the Himalayan region. It is extensively used for the production of natural steroidal saponins and flavonoids. Although seed dormancy of wild plants can be broken to be artificially maintained and regenerated through micropropagation in the laboratory, the success of secondary metabolite production in higher quantities and the synthesis of superior plant metabolites have been very limited. In this study, we present differential metabolic profiling of P. polyphylla plants maintained for 8 years in natural and greenhouse conditions. Untargeted profiling of the metabolites through ultra-performance liquid chromatography-mass spectrometry/mass spectrometry (UPLC-MS/MS), followed by statistical analysis, identified secondary metabolites that were enriched in the naturally occurring plant roots compared with the greenhouse plant roots. A multivariate statistical analysis revealed the differential distribution of the compounds between the two groups. Overall, we identified 1,182 secondary metabolites, with 116 metabolites being differentially upregulated and 256 metabolites being downregulated. Moreover, 810 metabolites showed no significant variation under both growing conditions. The Kyoto Encyclopedia of Genes and Genomes (KEGG) analysis revealed that the naturally forest-grown P. polyphylla plants were significantly enriched in steroidal saponins, lipids, vitamins, flavonoids, and flavonols. An analysis of the top 10 differentially upregulated secondary metabolites indicated a significantly enriched quantity of spirost-5-en-3,12-diol and kaempferol synthesis pathways, which are known to reduce the effect of free radicals scavengers inside the cell. In addition, veratramine alkaloids were also enriched under natural conditions. Our findings indicated that naturally maintained P. polyphylla plants are suitable for the extraction of medicinally important compounds. Our study established a causal relationship between the metabolic composition of the roots and their natural growth condition. This study highlighted the importance of environmental conditions in the biosynthesis of secondary metabolites of plants. [ABSTRACT FROM AUTHOR]

Gnetum formosum Markgr., a member of the Gnetaceae family, is distributed in Vietnam. This plant remains a botanical enigma with an unexplored diversity of chemical constituents and pharmacological effects. In this study, two new steroidal saponins, namely gnetumosides A (1) and B (2), were isolated from the aerial parts of G. formosum. Their chemical structures were elucidated using spectroscopic techniques, including high-resolution electrospray ionization mass spectrometry (HR-ESI-MS) and NMR, along with chemical hydrolysis and comparison with the reported literature. The potential anti-inflammatory effects of the isolated compounds were evaluated by measuring lipopolysaccharide-stimulated nitric oxide (NO) production in murine macrophage cells. Notably, compound 1 exhibited the most potent inhibitory activity (IC50 = 14.10 ± 0.75 µM), comparable to dexamethasone. Additionally, the mechanisms underlying the observed anti-inflammatory effects were investigated through molecular docking and molecular dynamics simulations on inducible nitric oxide synthase (iNOS) and cyclooxygenase-2 (COX-2) proteins. This study is the first to investigate the chemical constituents and pharmacological effects of G. formosum. [ABSTRACT FROM AUTHOR]

Solanum surattense Burm. f. is a significant member of the Solanaceae family, and the Solanum genus is renowned for its traditional medicinal uses and bioactive potential. This systematic review adheres to PRISMA methodology, analyzing scientific publications between 1753 and 2023 from B-on, Google Scholar, PubMed, Science Direct, and Web of Science, aiming to provide comprehensive and updated information on the distribution, ethnomedicinal uses, chemical constituents, and pharmacological activities of S. surattense, highlighting its potential as a source of herbal drugs. Ethnomedicinally, this species is important to treat skin diseases, piles complications, and toothache. The fruit was found to be the most used part of this plant (25%), together with the whole plant (22%) used to treat different ailments, and its decoction was found to be the most preferable mode of herbal drug preparation. A total of 338 metabolites of various chemical classes were isolated from S. surattense, including 137 (40.53%) terpenoids, 56 (16.56%) phenol derivatives, and 52 (15.38%) lipids. Mixtures of different parts of this plant in water–ethanol have shown in vitro and/or in vivo antioxidant, anti-inflammatory, antimicrobial, anti-tumoral, hepatoprotective, and larvicidal activities. Among the metabolites, 51 were identified and biologically tested, presenting antioxidant, anti-inflammatory, and antitumoral as the most reported activities. Clinical trials in humans made with the whole plant extract showed its efficacy as an anti-asthmatic agent. Mostly steroidal alkaloids and triterpenoids, such as solamargine, solanidine, solasodine, solasonine, tomatidine, xanthosaponin A–B, dioscin, lupeol, and stigmasterol are biologically the most active metabolites with high potency that reflects the new and high potential of this species as a novel source of herbal medicines. More experimental studies and a deeper understanding of this plant must be conducted to ensure its use as a source of raw materials for pharmaceutical use. [ABSTRACT FROM AUTHOR]

Two new spirostanol glycosides, (25S)-5α-spirosta-1β,3β-diol 1-O-α-L-rhamnopyranosyl-(1→2)-β-Dfucopyranoside (1) and 5α-spirost-(25)27-ene-1β,3β-diol 1-O-α-L-rhamnopyranosyl-(1→2)-(4-Osulfo)-β-D-fucopyranosyl 3-O-α-L-rhamnopyranoside (2), were isolated from the aerial part of Cordyline fruticosa (L.) A. Chev. Their structures were determined by spectroscopic analysis 1D and 2D NMR, and mass spectrometry (HR-ESI-MS in positive mode). [ABSTRACT FROM AUTHOR]

Two new steroidal saponins, 26-O-β-D-glucopyranosyl-22α-methoxy-5α-furost-25(27)-ene-1β,3β,26-triol 1-O-β-D-glucopyranoside (1), and 26-O-β-D-glucopyranosyl-22α-methoxy-furosta-5,25(27)-diene-1β,3β,26-triol 1-O-α-L-rhamnopyranosyl-(1→2)-β-D-fucopyranoside (2) were isolated and elucidated from the roots of Cordyline fruticosa (L.) A. Chev. Their structures were established by interpretation of spectroscopic data (1 D and 2 D NMR) and mass spectrometry (HR-ESI-MS). [ABSTRACT FROM AUTHOR]

The fruits of Solanum torvum Swartz, a wild relative of eggplant, are consumed as a wild vegetable in tropical regions of Africa, Asia, and South America. In traditional Chinese medicine, it is believed to have anti-inflammatory and sedative effects. In the Philippines, water decoction is used to treat hyperactivity disorder. Twenty-two steroidal saponins were isolated and purified from the fruits grown in Yunnan, China, including six new compounds: torvosides U–Z (1–6). During drying and cooking, the saponins may undergo transformation, resulting in small amounts of sapogenins. These transformations can include dehydration of hydroxyl groups at position C22, formation of double bonds at position 20, 22 or 22, 23, and even formation of peroxide products. Saponin compounds torvoside X (4), torvoside Y (5), torvoside A (7), and (25S)-3-oxo-5α-spirostan-6α-yl-O-β-d-xylopyranoside (20), which are glycosylated at C-6, showed certain anti-epileptic activity in a pentylenetetrazole-induced zebrafish seizure model. No antiproliferative activity was detected when tested on the cancer cell line HepG2, and no hepatotoxic effect was noted on normal liver cell line LO2. [ABSTRACT FROM AUTHOR]

Saponins are naturally occurring compounds ubiquitously present in various organisms, predominantly in plants. They are noted for forming colloidal solutions in water, which foam on shaking and precipitate cholesterol. Several in vitro and in vivo tests on mixtures and individual saponins have revealed a broad spectrum of biological and pharmacological activities, including cancer-related activity, antiphlogistic and antiallergic, immunomodulating, antihepatotoxic, antiviral, hypoglycemic, antifungal and molluscicidal activities. The Dracaena genus is renowned for an abundance of steroidal saponins utilized in treating digestive and hematological disorders. Previous studies on this genus revealed the presence of steroidal saponins, some of which showed cytotoxic activities against cultured tumor cells and interesting biological activities. This study procured steroidal saponin from the foliage of D. draco L. using various chromatographic techniques and 1D and 2D nuclear magnetic resonance (NMR) spectroscopic analysis. The structure was deduced as 26-O-β-D-glucopyranosyl-22-O-methylfurosta-5,25(27)-diene-1β,3β,22α,26- tetrol 1-O-{O-α-L-rhamnopyranosyl-(1→2)-α-L-arabinopyranosyl}; a compound previously isolated from the underground parts of Ruscus aculeatus in Japan. Future evaluation of the saponin’s biological activity is imperative to enhance chemotaxonomic data concerning the chemical composition and biological functionality of D. draco L. and, by extension, the Dracaena genus.

Background: In the research of the pharmacological activity of modern Chinese medicine, a large number of traditional Chinese medicines show anti-inflammatory activity. Asparagi radix is one of the anti-inflammatory drugs. With the deepening of people's research on Asparagi radix, its anti-inflammatory pharmacological effects have been gradually explored, but its specific anti-inflammatory active ingredients are still unclear. Therefore, it is necessary to screen and identify its specific anti-inflammatory active ingredients from Asparagi radix. At present, COX-2 is an important target for the treatment of chronic inflammation, and many drugs targeting this target have been marketed. However, some drugs have serious side effects, so it is very meaningful to study new COX-2 inhibitors. Methods: In this experiment, the fractions of different time periods are separated by high performance liquid chromatography-separation-trapping system (HPLC-CAD-FC). Then, ultra-high performance liquid chromatography-quadrupole time-offlight/mass spectrometry (UPLC-Q-TOF/MS) and biological activity analysis techniques are used to identify the chemical composition and in vitro anti-inflammatory activity of each fraction. Finally, the data is integrated to screen out the substances with potential anti-inflammatory activity in Asparagi radix. Results: The results showed that the method established in this experiment can successfully isolate the active components of Asparagi radix, and four saponins with potential anti-inflammatory activity are identified. Conclusion: In summary, the analysis method established in this study can quickly and effectively screen out its anti-inflammatory active substances, and its potential anti-inflammatory active ingredients are mainly steroidal saponins. [ABSTRACT FROM AUTHOR]

Allii Macrostemonis Bulbus (AMB), a traditional Chinese edible and medicinal plant, is considered beneficial to health. In this study, we isolated and purified nine steroidal saponins (compounds 1–9) from AMB. Their structures were characterized using physicochemical properties, HR-ESI-MS, 1D and 2D NMR spectroscopy. Among these compounds, compounds 1–5 were newly discovered named macrostemonoside U-Y, respectively. We assessed the in vitro antioxidant properties of the nine steroidal saponins through free radical scavenging and reducing power assays. This provides options for developing natural antioxidants. Additionally, an HPLC-ELSD quantitative analysis method was developed for the nine saponins in 12 batches of AMB from different origins and processing methods. The results showed that the contents of the nine steroidal saponins in AMB varied greatly among different growing environments and processing methods.

Gnetum formosum Markgr., a member of the Gnetaceae family, is distributed in Vietnam. This plant remains a botanical enigma with an unexplored diversity of chemical constituents and pharmacological effects. In this study, two new steroidal saponins, namely gnetumosides A (1) and B (2), were isolated from the aerial parts of G. formosum. Their chemical structures were elucidated using spectroscopic techniques, including high-resolution electrospray ionization mass spectrometry (HR-ESI-MS) and NMR, along with chemical hydrolysis and comparison with the reported literature. The potential anti-inflammatory effects of the isolated compounds were evaluated by measuring lipopolysaccharide-stimulated nitric oxide (NO) production in murine macrophage cells. Notably, compound 1 exhibited the most potent inhibitory activity (IC50 = 14.10 ± 0.75 µM), comparable to dexamethasone. Additionally, the mechanisms underlying the observed anti-inflammatory effects were investigated through molecular docking and molecular dynamics simulations on inducible nitric oxide synthase (iNOS) and cyclooxygenase-2 (COX-2) proteins. This study is the first to investigate the chemical constituents and pharmacological effects of G. formosum.

Two new compounds named 4,4′-bis(β-D-glucopyranosyloxy)biphenyl (1) and spirostane-25(27)-en-2α,3β-diol-3-O-β-D-xylopyranosyl(1→3)-β-D-glucopyranosyl(1→4)-β-D-galactopyranoside (2) were isolated from n-butanol extraction part of 80% ethanol extract of Allii Macrostemonis Bulbus. Alongside these, ten known compounds (3–12) were also identified, including a flavonoid glycoside (3), seven steroids (4–10), a nucleoside (11), and a phenylpropanoid glycoside (12) were found. Notably, compounds 3–6 were isolated from this plant for the first time. The structures of all compounds were confirmed using high-resolution electrospray ionization mass spectrometry (HR-ESI-MS), 1D, and 2D NMR spectroscopy. Some of these compounds showed strong antioxidant activity, and compound 1 demonstrated the most potent reduction of ferric ions (Fe3+) with an IC50 value of 0.59 ± 0.18 mg/mL. Compounds 2 and 3 exhibited the highest scavenging activity against superoxide anion radicals (O2−·) with an IC50 value of 0.02 ± 0.01 mg/mL. Additionally, compound 3 displayed substantial scavenging activity against 2,2-diphenyl-1-picrylhydrazyl (DPPH) and 2,2′-azino-bis(3-ethylbenzothiazoline-6-sulfonic acid) (ABTS) with IC50 values of 0.21 ± 0.17 mg/mL and 0.02 ± 0.01 mg/mL, respectively. The discovery of these two new compounds is a reference for identifying Allii Macrostemonis Bulbus quality markers. Moreover, their exceptional antioxidant activity offers a promising avenue for uncovering novel natural antioxidants. [ABSTRACT FROM AUTHOR]

The fruits of Solanum torvum Swartz, a wild relative of eggplant, are consumed as a wild vegetable in tropical regions of Africa, Asia, and South America. In traditional Chinese medicine, it is believed to have anti-inflammatory and sedative effects. In the Philippines, water decoction is used to treat hyperactivity disorder. Twenty-two steroidal saponins were isolated and purified from the fruits grown in Yunnan, China, including six new compounds: torvosides U–Z (1–6). During drying and cooking, the saponins may undergo transformation, resulting in small amounts of sapogenins. These transformations can include dehydration of hydroxyl groups at position C22, formation of double bonds at position 20, 22 or 22, 23, and even formation of peroxide products. Saponin compounds torvoside X (4), torvoside Y (5), torvoside A (7), and (25S)-3-oxo-5α-spirostan-6α-yl-O-β-d-xylopyranoside (20), which are glycosylated at C-6, showed certain anti-epileptic activity in a pentylenetetrazole-induced zebrafish seizure model. No antiproliferative activity was detected when tested on the cancer cell line HepG2, and no hepatotoxic effect was noted on normal liver cell line LO2.

Paris polyphylla Smith (Melanthiaceae) family, which is native to the Himalayan region, has received a lot of attention recently due to its extensive history of usage in traditional medicine. The production of steroidal saponin from callus suspension cultures of P. polyphylla was observed in the current study. The current study attempted to develop a P. polyphylla plant callus suspension culture through optimization of cultivation technique for callus suspension, quantification of total phenolic components and estimation of the extract's antioxidant activity. A light-yellow callus was formed within six weeks of cultivating rhizomes on Murashige and Skoog (MS) media supplemented with Thidiazuron (TDZ). Furthermore, the effect of TDZ, Methyl Jasmonate (MeJA), and Yeast Extract (YE) on callus growth, steroidal saponin (dioscin and diosgenin), total phenolic content, total flavonoids, total tannin, and total antioxidant activity was also measured. The medium containing 0.5 mM TDZ depicted the maximum callus biomass (2.98 g fresh weight). Significantly high phenolic and tannin content was observed in the MS medium containing 50 mM MeJA, whereas, no significant increase was observed in total tannin production in any treatment. Three in vitro assays, DPPH (2,2-diphenyl-1-picrylhydrazyl), ABTS (2,2'-azino-bis (3-ethylbenzothiazoline-6-sulfonic acid)) and FRAP (ferric ion reducing antioxidant potential) and FC (Folin-Ciocalteu), were used to assess antioxidant potential of callus. Maximum antioxidant analysis reported in 1.0 mM TDZ (6.89 mM AAE/100 g) containing medium followed by 50 mM MeJA (6.44 mM AAE/100 g). The HPLC analysis showed a high presence of dioscin and diosgenin (5.43% and 21.09%, respectively) compared to the wild sample (2.56% and 15.05%, respectively). According to the results, callus produced on media supplemented with 50 mM MeJA have significant phenolic contents and elevated antioxidant activity; nevertheless, callus growth was greater in the presence of 0.5 mM TDZ. The findings of the current study have commercial implications since greater biomass production will result in active phytochemicals that the pharmaceutical and nutraceutical sectors are in need desperately. [ABSTRACT FROM AUTHOR]

Prosapogenin A is a secondary saponin in Dioscorea zingiberensis, and it showed remarkable pharmacological effects. Due to very low content and lack of well-developed biotransformation, its preparation was not efficient and clean. This study aims to establish an eco-friendly strategy for preparation of Prosapogenin A from plant material. Physical separation was employed to recycle starch and cellulose, and then D101 resin and polyamide packed-bed column was incorporated for purification of total steroidal saponins (TSS). After these pretreatments, purity of TSS was largely increased to 83.2% with recovery at 87.6%, which was subjected to enzymatic hydrolysis. Optimized reaction system was constructed in 0.20 M HAc-NaAc buffer (pH4.2) containing cellulase/TSS (3:1, w/w), and the hydrolysis was performed at 53 °C for 6 h. Consequently, TSS was almost completely hydrolyzed to Prosapogenin A, while the highest yield reached 5.62%. The newly proposed approach is promising for efficient preparation of Prosapogenin A in industrial applications. [ABSTRACT FROM AUTHOR]

Cholesterol serves as a key precursor for many high-value chemicals such as plant-derived steroidal saponins and steroidal alkaloids, but a plant chassis for effective biosynthesis of high levels of cholesterol has not been established. Plant chassis have significant advantages over microbial chassis in terms of membrane protein expression, precursor supply, product tolerance, and regionalization synthesis. Here, using Agrobacterium tumefaciens -mediated transient expression technology, Nicotiana benthamiana , and a step-by-step screening approach, we identified nine enzymes (SSR1-3, SMO1-3, CPI-5, CYP51G, SMO2-2, C14-R-2, 8,7SI-4, C5-SD1, and 7-DR1-1) from the medicinal plant Paris polyphylla and established detailed biosynthetic routes from cycloartenol to cholesterol. Specfically, we optimized HMGR , a key gene of the mevalonate pathway, and co-expressed it with the PpOSC1 gene to achieve a high level of cycloartenol (28.79 mg/g dry weight, which is a sufficient amount of precursor for cholesterol biosynthesis) synthesis in the leaves of N. benthamiana. Subsequently, using a one-by-one elimination method we found that six of these enzymes (SSR1-3, SMO1-3, CPI-5, CYP51G, SMO2-2, and C5-SD1) were crucial for cholesterol production in N. benthamiana , and we establihed a high-efficiency cholesterol synthesis system with a yield of 5.63 mg/g dry weight. Using this strategy, we also discovered the biosynthetic metabolic network responsible for the synthesis of a common aglycon of steroidal saponin, diosgenin, using cholesterol as a substrate, obtaining a yield of 2.12 mg/g dry weight in N. benthamiana. Our study provides an effective strategy to characterize the metabolic pathways of medicinal plants that lack a system for in vivo functional verification, and also lays a foundation for the synthesis of active steroid saponins in plant chassis. • Cholesterol biosynthetic pathway is a complicated network. • A trucked HMGR is helpful to improve cycloartenol production. • Six of cholesterol biosynthetic genes were crucial for cholesterol production. • A high-efficiency cholesterol synthesis system in plant chassis is established for the first time. • An effective strategy was proposed to characterize the metabolic pathways. [ABSTRACT FROM AUTHOR]

Paris polyphylla Smith (Melanthiaceae) family, which is native to the Himalayan region, has received a lot of attention recently due to its extensive history of usage in traditional medicine. The production of steroidal saponin from callus suspension cultures of P. polyphylla was observed in the current study. The current study attempted to develop a P. polyphylla plant callus suspension culture through optimization of cultivation technique for callus suspension, quantification of total phenolic components and estimation of the extract’s antioxidant activity. A light-yellow callus was formed within six weeks of cultivating rhizomes on Murashige and Skoog (MS) media supplemented with Thidiazuron (TDZ). Furthermore, the effect of TDZ, Methyl Jasmonate (MeJA), and Yeast Extract (YE) on callus growth, steroidal saponin (dioscin and diosgenin), total phenolic content, total flavonoids, total tannin, and total antioxidant activity was also measured. The medium containing 0.5 μM TDZ depicted the maximum callus biomass (2.98 g fresh weight). Significantly high phenolic and tannin content was observed in the MS medium containing 50 μM MeJA, whereas, no significant increase was observed in total tannin production in any treatment. Three in vitro assays, DPPH (2,2-diphenyl-1-picrylhydrazyl), ABTS (2,2′-azino-bis (3-ethylbenzothiazoline- 6-sulfonic acid)) and FRAP (ferric ion reducing antioxidant potential) and FC (Folin-Ciocalteu), were used to assess antioxidant potential of callus. Maximum antioxidant analysis reported in 1.0 μM TDZ (6.89 mM AAE/100 g) containing medium followed by 50 μM MeJA (6.44 mM AAE/100 g). The HPLC analysis showed a high presence of dioscin and diosgenin (5.43% and 21.09%, respectively) compared to the wild sample (2.56% and 15.05%, respectively). According to the results, callus produced on media supplemented with 50 μM MeJA have significant phenolic contents and elevated antioxidant activity; nevertheless, callus growth was greater in the presence of 0.5 μM TDZ. The findings of the current study have commercial implications since greater biomass production will result in active phytochemicals that the pharmaceutical and nutraceutical sectors are in need desperately.

Four new steroidal saponins, (20 S ,22 Z ,25 S)-26-[(β- D -glucopyranosyl)oxy]-20-hydroxyfurosta-5,22-dien-3β-yl O -β- D -apiofuranosyl-(1→3)- O -β- D -glucopyranosyl-(1→4)- O -α- L -rhamnopyranosyl-(1→3)- O -[α- L -rhamnopyranosyl-(1→2)]-β- D -glucopyranoside (taccaintegrifoside A, 1), (20 S ,22 Z ,25 R)-26-[(β- D -glucopyranosyl)oxy]-20-hydroxyfurosta-5,22-dien-3β-yl O -α- L -rhamnopyranosyl-(1→2)- O -[α- L -rhamnopyranosyl-(1→3)]-β- D -glucopyranoside (taccaintegrifoside B, 2) and (20 S ,22 Z ,25 R)-26-[(β- D -glucopyranosyl)oxy]-20-hydroxyfurosta-5,22-dien-3β-yl O -β- D -glucopyranosyl-(1→4)- O -α- L -rhamnopyranosyl-(1→3)- O -[α- L -rhamnopyranosyl-(1→2)]-β- D -glucopyranoside (taccaintegrifoside C, 3), and (20 S ,22 Z ,25 R)-26-[(β- D -glucopyranosyl)oxy]-20-methoxyfurosta-5,22-dien-3β-yl O -α- L -rhamnopyranosyl-(1→2)- O -[α- L -rhamnopyranosyl-(1→3)]-β- D -glucopyranoside (taccaintegrifoside D, 4) were isolated from the rhizomes of Tacca integrifolia Ker Gawl.; in addition to nine known compounds. Taccaintegrifosides B (2) and C (3) were found to be 25 R -analogues of 5 and 6 , respectively. The structure determinations were considered based on the physical data and spectroscopic evidence, including 1D and 2D NMR experiments. [Display omitted] • Four new steroidal saponins were isolated from Tacca integrifolia rhizomes. • Steroidal saponins with 25 S and 25 R -diastereomers were reported from the genus Tacca. • This study added the information data of the secondary metabolites to the genus Tacca. [ABSTRACT FROM AUTHOR]

Steroidal saponin compound in Dioscorea species is one of the crucial substances because it has some biological functions, such as immunomodulatory and anti-allergic agent. This study aims to analyze the effect of steroidal saponin of Dioscorea alata L. on CD4 T cells activation, cytokines IL-4, IL-5 and TGF-β. This study used primary lymphocyte cell which isolated from BALB/c mice spleen. Mice lymphocytes were cultured in the complete medium with presence of various concentrations (50, 25 and 12.5 μg/mL) of three isolate of steroidal saponin of D. alata for 24 h. Diosgenin was used as positive control. After 24 h of treatment, the activation of lymphocyte, IL-4 and IL-5 production was determined by Flowcytometry analysis. Data were analyzed using student t-test with p < 0.05 and p < 0.01. The results showed that the low concentration of Isolate 1 (12.5 μg/mL) was found to be effective to stimulate the activation of CD4 T cells, reduce the production of IL4 and IL-5 by CD4 T cells and increase TGF-β production. These results showed that a low concentration of steroidal saponin of D. alata could be considered as immunomodulatory and anti-allergic agent. Purification and identification of each isolate isolated from DAE is in progress. [ABSTRACT FROM AUTHOR]

Polygonatum punctatum Royle ex Kunth is a high-value medicinal plant found in old natural forests. A phytochemical study on the roots of this plant led to the isolation of seven new steroidal saponins including four furostans (1–4) and three furospirostans (5–7). Their structures were elucidated as (25R)-26-O-(β-d-glucopyranosyl)-furost-5-ene-3β,17α,22α,26-tetraol 3-O-α-l-arabinopyranosyl-(1 → 2)-β-d-glucopyranosyl-(1 → 4)-β-d-galactopyranoside (1), (25R)-26-O-(β-d-glucopyranosyl)-furost-5-ene-3β,14α,17α,22α,26-pentaol 3-O-α-l-arabinopyranosyl-(1 → 2)-β-d-glucopyranosyl-(1 → 4)-β-d-galactopyranoside (2), (25R)-26-O-(β-d-glucopyranosyl)-furost-5-ene-22α-methoxy-3β,17α,26-triol 3-O-α-l-arabinopyranosyl-(1 → 2)-β-d-glucopyranosyl-(1 → 4)-β-d-galactopyranoside (3), (25R)-26-O-(β-d-glucopyranosyl)-furost-5-ene-22α-methoxy-3β,17α,26-triol 3-O-[α-l-arabinopyranosyl-(1 → 2)-β-d-glucopyranosyl-(1 → 4)]-[acetoxy-(→ 6)]-β-d-galactopyranoside (4), 26-O-(β-d-glucopyranosyl)-14α,17α-dihydroxynuatigenin 3-O-α-l-arabinopyranosyl-(1 → 2)-β-d-glucopyranosyl-(1 → 4)-β-d-galactopyranoside (5), 26-O-(β-d-glucopyranosyl)-17α-hydroxynuatigenin 3-O-α-l-arabinopyranosyl-(1 → 2)-β-d-glucopyranosyl-(1 → 4)-β-d-galactopyranoside (6), and 26-O-(β-d-glucopyranosyl)-14α-hydroxynuatigenin 3-O-α-l-arabinopyranosyl-(1 → 2)-β-d-glucopyranosyl-(1 → 4)-β-d-galactopyranoside (7) by extensive spectroscopic analyses, including infrared, high-resolution electrospray ionization mass spectrometry, and one- and two-dimensional nuclear magnetic resonance spectroscopy. Compounds 1–7 inhibited nitric oxide production in lipopolysaccharide activated RAW264.7 cells with IC50 values ranging from 41.5 ± 3.2 to 62.2 ± 3.7 µM, compared to 33.8 ± 2.6 µM for the positive control compound l-NMMA. [ABSTRACT FROM AUTHOR]

Background and purpose: Phytochemically, Allium species are a rich source of important secondary metabolites especially steroidal saponin and sapogenins, flavonoids, and sulfur compounds. As a member of this genus, Allium affine, which is locally known as "tareh kouhi", is an endemic plant of middle Asian countries. Experimental approach: Bulbs of A. affine were collected and air-dried in the shade. The chloroform-methanol (9:1) extract of the sample was subjected to purification by MPLC and HPLC. Structure elucidation of isolated compounds was done using comprehensive spectroscopic methods including 1D-NMR, 2D-NMR, and MS. Findings/Results: A steroidal saponin structurally related to parillin and a phenylpropanoid glycoside (coniferin) were isolated and identified from the plant chloroform-methanol extract. Conclusion and implication: To the best of our knowledge isolation of these potentially medicinal compounds from A. affine was reported for the first time in this study. [ABSTRACT FROM AUTHOR]

Plant growth-stimulation bioactivity of triterpenoid saponins is well known, especially for oleanane-type compounds. Nevertheless, a few phytotoxicity bioassays performed on some steroidal saponins have shown hormesis profiles and growth stimulation on Lactuca sativa roots. The focus of the work described here was on the use of the wheat coleoptile bioassay to evaluate plant growth stimulation, and on the search for a commercially available source of active saponins by bio-guided fractionation strategy. Selected saponins were tested and a cluster analysis showed that those saponins with a sugar chain of more than five units had a hormesis profile, while saponins with growth enhancement had fewer sugar residues. Two saponins showed similar activity to the positive control, namely the phytohormone indole-3-butyric acid (IBA). As a potential source of these metabolites, a commercial extract of Yucca schidigera used as a fertilizer was selected. Bio-guided fractionation led to the identification of two fractions of defined composition and these showed stimulation values similar to the positive control. It was observed that the presence of a carbonyl group at C-12 on the aglycone skeleton led to improved activity. A saponin-rich fraction from Y. schidigera could be proposed to enhance crop quality and production. [ABSTRACT FROM AUTHOR]

Background and purpose: Phytochemically, Allium species are a rich source of important secondary metabolites especially steroidal saponin and sapogenins, flavonoids, and sulfur compounds. As a member of this genus, Allium affine, which is locally known as “tareh kouhi”, is an endemic plant of middle Asian countries. Experimental approach: Bulbs of A. affine were collected and air-dried in the shade. The chloroform-methanol (9:1) extract of the sample was subjected to purification by MPLC and HPLC. Structure elucidation of isolated compounds was done using comprehensive spectroscopic methods including 1D-NMR, 2D-NMR, and MS. Findings/Results: A steroidal saponin structurally related to parillin and a phenylpropanoid glycoside (coniferin) were isolated and identified from the plant chloroform-methanol extract. Conclusion and implication: To the best of our knowledge isolation of these potentially medicinal compounds from A. affine was reported for the first time in this study.

A new steroidal saponin, torvoside R (1), was isolated along with torvoside Q (2) and macaoside (3) from dichloromethane soluble-portion of the aerial parts of Solanum torvum. Their chemical structures were elucidated using HRESIMS, 1 D- and 2 D-NMR as well as comparison with those reported in the literature. All isolated compounds (1 − 3) exhibited cytotoxicity against SK-LU-1, HepG2, MCF-7, and T24 cancer cell lines with IC50 values ranging from 14.18 to 89.31 µg/mL. [ABSTRACT FROM AUTHOR]

Dioscorea zingiberensis is a valuable medicinal herb rich in steroidal saponins. To reveal the role of jasmonic acid (JA) on physiology and steroidal saponins accumulation, D. zingiberensis were treated with different concentrations of JA. The antioxidant capacity, photosynthetic parameters, fatty acids and metabolites related to steroidal saponins biosynthesis (phytosterols, diosgenin and steroidal saponins) were examined under JA treatment. The results demonstrated that JA treatment caused a great reduction in MDA, stomatal width, photosynthetic rate and photosynthetic pigment, induced a considerable increase in proline, soluble sugar, soluble protein and antioxidant enzymes (CAT, POD and SOD), and leaded to a significant up-regulation in the expression of genes related to antioxidant system and chlorophyll degradation. Specialized metabolites displayed various changes under different concentrations of JA. The majority of fatty acids exhibited negative responses to JA treatment in leaf and rhizome. In leaf, JA treatment enhanced the accumulation of phytosterols and diosgenin, but decreased the accumulation of steroidal saponins. However, steroidal saponins were mainly accumulated in rhizome and were highly increased by JA treatment. Redundancy analysis illustrated that fatty acids were strongly associated with metabolites related to steroidal saponins. Among all fatty acids, C16:0, C18:1, C18:3, C22:0 and C24:0 contributed most to the variation in metabolites related to steroidal saponin biosynthesis. Overall, JA treatment leaded to an increase in steroidal saponins, but an inhibition of plant growth. Thus, the negative effects of JA application on plant physiology should be carefully assessed before being utilized to increase the production of steroidal saponins in D. zingiberensis. • JA treatment enhanced accumulation of steroidal saponin. • JA stunted the growth of plant and induced the chlorophyll degradation. • Fatty acids were profoundly correlated with accumulation of steroid saponins. [ABSTRACT FROM AUTHOR]

Paris polyphylla is an important traditional medicinal plant of the Himalayan region. It is extensively used for the production of natural steroidal saponins and flavonoids. Although seed dormancy of wild plants can be broken to be artificially maintained and regenerated through micropropagation in the laboratory, the success of secondary metabolite production in higher quantities and the synthesis of superior plant metabolites have been very limited. In this study, we present differential metabolic profiling of P. polyphylla plants maintained for 8 years in natural and greenhouse conditions. Untargeted profiling of the metabolites through ultra-performance liquid chromatography-mass spectrometry/mass spectrometry (UPLC-MS/MS), followed by statistical analysis, identified secondary metabolites that were enriched in the naturally occurring plant roots compared with the greenhouse plant roots. A multivariate statistical analysis revealed the differential distribution of the compounds between the two groups. Overall, we identified 1,182 secondary metabolites, with 116 metabolites being differentially upregulated and 256 metabolites being downregulated. Moreover, 810 metabolites showed no significant variation under both growing conditions. The Kyoto Encyclopedia of Genes and Genomes (KEGG) analysis revealed that the naturally forest-grown P. polyphylla plants were significantly enriched in steroidal saponins, lipids, vitamins, flavonoids, and flavonols. An analysis of the top 10 differentially upregulated secondary metabolites indicated a significantly enriched quantity of spirost-5-en-3,12-diol and kaempferol synthesis pathways, which are known to reduce the effect of free radicals scavengers inside the cell. In addition, veratramine alkaloids were also enriched under natural conditions. Our findings indicated that naturally maintained P. polyphylla plants are suitable for the extraction of medicinally important compounds. Our study established a causal relationship between the metabolic composition of the roots and their natural growth condition. This study highlighted the importance of environmental conditions in the biosynthesis of secondary metabolites of plants., Competing Interests: The authors declare that the research was conducted in the absence of any commercial or financial relationships that could be construed as a potential conflict of interest., (Copyright © 2024 Yan, Wang, Zhang, Xia, Jiao, Ghanim, Xiaokun, He and Shi.)

A new saponin namely diosgeninoside (25  R -spirost-5-en-3- O -[ β - D -glucopyranosyl (1→2) - β - D -glucuronic acid]) and a new fatty acid betacic acid: ( Z )-8( S *),9( S *),10( R *)-trihydroxy-11-octadecenoic acid together with six known compounds: N - trans -coumaroyl tyramine, ergosta-7,22-dien - 3 β, 5 α,6β- triol, β -sitosterol, and β -sitosterol-3- O - β - D -glucopyranoside, L -threitol and soya-cerebroside I were isolated from the methanolic extract of Solanum betaceum . The structures were elucidated by interpretation of their 1D and 2D NMR spectra and spectrometric data. The methanolic extract, the EtOAc and n -BuOH fractions, and several isolated compounds were tested for antibacterial activity against four bacteria ( Staphylococcus aureus ; Staphylococcus epidermidis ; Escherichia coli ; and Pseudomonas aeruginosa ). The methanolic extract and the EtOAc fraction showed moderate activity against Staphylococcus aureus and Pseudomonas aeruginosa with MIC value of 128 µg/mL. Compound 1 showed moderate activity against Staphylococcus aureus with MIC value of 64 µg/mL.

Two new compounds named 4,4′-bis(β-D-glucopyranosyloxy)biphenyl (1) and spirostane-25(27)-en-2α,3β-diol-3-O-β-D-xylopyranosyl(1→3)-β-D-glucopyranosyl(1→4)-β-D-galactopyranoside (2) were isolated from n-butanol extraction part of 80% ethanol extract of Allii Macrostemonis Bulbus. Alongside these, ten known compounds (3–12) were also identified, including a flavonoid glycoside (3), seven steroids (4–10), a nucleoside (11), and a phenylpropanoid glycoside (12) were found. Notably, compounds 3–6 were isolated from this plant for the first time. The structures of all compounds were confirmed using high-resolution electrospray ionization mass spectrometry (HR-ESI-MS), 1D, and 2D NMR spectroscopy. Some of these compounds showed strong antioxidant activity, and compound 1 demonstrated the most potent reduction of ferric ions (Fe3+) with an IC50 value of 0.59 ± 0.18 mg/mL. Compounds 2 and 3 exhibited the highest scavenging activity against superoxide anion radicals (O2−·) with an IC50 value of 0.02 ± 0.01 mg/mL. Additionally, compound 3 displayed substantial scavenging activity against 2,2-diphenyl-1-picrylhydrazyl (DPPH) and 2,2′-azino-bis(3-ethylbenzothiazoline-6-sulfonic acid) (ABTS) with IC50 values of 0.21 ± 0.17 mg/mL and 0.02 ± 0.01 mg/mL, respectively. The discovery of these two new compounds is a reference for identifying Allii Macrostemonis Bulbus quality markers. Moreover, their exceptional antioxidant activity offers a promising avenue for uncovering novel natural antioxidants.

Trillium govanianum, commonly known as Nag Chhatri and Teen Patra, is a popular herbal supplement traditionally used for curing different inflammatory and sexual disorders, infection and wound healing. Steroidal saponins are considered as active components of this species. The present study demonstrated the isolation of nine steroidal saponins, including one new compound named as govanoside B (9) and eight known, pregna-chacotrioside (1), pennogenin-triglycoside (2), borassoside E (3), pennogenin-tetraglycoside (4), protodioscin (5), clintonioside B (6), pennogenin-diglycoside (7) and borassoside D (8). This is the first report on the isolation of 1, 2, 4, 5, 6, 7 and 8 from rhizomes of T. govanianum. The extract, fractions and isolated compounds were further evaluated for their DPPH and ABTS radical scavenging activity. [ABSTRACT FROM AUTHOR]

Plant growth-stimulation bioactivity of triterpenoid saponins is well known, especially for oleanane-type compounds. Nevertheless, a few phytotoxicity bioassays performed on some steroidal saponins have shown hormesis profiles and growth stimulation on Lactuca sativa roots. The focus of the work described here was on the use of the wheat coleoptile bioassay to evaluate plant growth stimulation, and on the search for a commercially available source of active saponins by bio-guided fractionation strategy. Selected saponins were tested and a cluster analysis showed that those saponins with a sugar chain of more than five units had a hormesis profile, while saponins with growth enhancement had fewer sugar residues. Two saponins showed similar activity to the positive control, namely the phytohormone indole-3-butyric acid (IBA). As a potential source of these metabolites, a commercial extract of Yucca schidigera used as a fertilizer was selected. Bio-guided fractionation led to the identification of two fractions of defined composition and these showed stimulation values similar to the positive control. It was observed that the presence of a carbonyl group at C-12 on the aglycone skeleton led to improved activity. A saponin-rich fraction from Y. schidigera could be proposed to enhance crop quality and production.

The good phytotoxicity and selectivity against weeds versus tomato or cress make saponin-rich fractions from Agave macroacantha , A. colorata , A. parryi , and A. parrasana attractive candidates as bioherbicides. The saponin contents have only previously been reported for A. macroacantha , and as a consequence, simultaneous dereplication has been performed on saponin-rich fractions from the other plants by mass spectrometry (MS) and nuclear magnetic resonance (NMR) spectroscopy. This strategy enables the identification of a total of 26 saponins, 14 of which have been described previously and 12 of which are proposed as new saponins. They include isomers and a new sugar chain with a β-d-apiofuranose unit. The method is corroborated by the isolation of eight dereplicated saponins from A. colorata .

Tomato seeds contain steroidal saponins called lycoperosides. However, it currently remains unclear whether lycoperosides exert anti‐inflammatory or anti‐allergic effects. Therefore, we herein investigated the effects of tomato seed extract (TSE) and lycoperoside H (LH) in Interleukin (IL)‐33 transgenic mice. TSE (500 mg/kg) or LH (10 mg/kg) was orally administered once a day for 101 days and then evaluated mouse behavior, skin symptoms, and blood and skin inflammatory cytokines. TSE slightly suppressed scratching behavior, while TSE and LH both increased locomotive activity. LH also significantly suppressed inflammation scores in the limbs, and TSE and LH reduced transepidermal water loss. Epidermal hyperplasia and the accumulation of eosinophils and mast cells were decreased by TSE and LH. Skin Th2/Th1 cytokine ratio and serum IgE concentrations were significantly reduced by TSE and LH. The present results suggest that the oral administration of LH derived from tomato seeds effectively ameliorates the symptoms of atopic dermatitis. Practical applications: It has been reported that tomato seeds contain steroidal saponins, lycoperosides, though the effects of lycoperosides on anti‐inflammatory or anti‐allergic have not yet been revealed. In this study, we demonstrated that the oral administration of lycoperoside H derived from tomato seeds suppressed atopic dermatitis symptoms in IL‐33 transgenic mice. [ABSTRACT FROM AUTHOR]

Dioscorea zingiberensis accumulates abundant steroidal saponins, such as dioscin, which is the principal bioactive ingredient displaying a wide range of pharmacological activities. Diosgenin is the aglycone of dioscin, and recently, genes encoding cytochrome P450 enzymes in the late steps of diosgenin biosynthesis have been isolated. Diosgenin was successfully synthesized in the cholesterol-producing yeasts. From diosgenin to dioscin, one glucose and two rhamnose groups need to be added. Although genes encoding UDP-glucosyltransferases converting diosgenin to trillin were isolated, genes encoding UDP-rhamnosyltransferases involved in dioscin biosynthesis remain unknown. In this study, we isolated the cDNA encoding the trillin rhamnosyltransferase (designated DzGT1) from D. zingiberensis. Heterologous expression of DzGT1 in Escherichia coli cells showed that the gene product exhibits an enzyme activity that glycosylates the trillin to form prosapogenin A of dioscin (PSA). The transcript level of DzGT1 is in accord with PSA accumulation in different organs of D. zingiberensis. Integration of the biochemical, metabolic, and transcriptional data supported the function of DzGT1 in dioscin biosynthesis. The identification and characterization of DzGT1 will help understand the metabolism of steroidal saponins in D. zingiberensis and provide candidate UDP-rhamnosyltransferase for efficient production of PSA, dioscin, and relevant steroidal saponins in microbial hosts.

Dioscorea zingiberensis accumulates abundant steroidal saponins, such as dioscin, which is the principal bioactive ingredient displaying a wide range of pharmacological activities. Diosgenin is the aglycone of dioscin, and recently, genes encoding cytochrome P450 enzymes in the late steps of diosgenin biosynthesis have been isolated. Diosgenin was successfully synthesized in the cholesterol-producing yeasts. From diosgenin to dioscin, one glucose and two rhamnose groups need to be added. Although genes encoding UDP-glucosyltransferases converting diosgenin to trillin were isolated, genes encoding UDP-rhamnosyltransferases involved in dioscin biosynthesis remain unknown. In this study, we isolated the cDNA encoding the trillin rhamnosyltransferase (designated DzGT1) from D. zingiberensis. Heterologous expression of DzGT1 in Escherichia coli cells showed that the gene product exhibits an enzyme activity that glycosylates the trillin to form prosapogenin A of dioscin (PSA). The transcript level of DzGT1 is in accord with PSA accumulation in different organs of D. zingiberensis. Integration of the biochemical, metabolic, and transcriptional data supported the function of DzGT1 in dioscin biosynthesis. The identification and characterization of DzGT1 will help understand the metabolism of steroidal saponins in D. zingiberensis and provide candidate UDP-rhamnosyltransferase for efficient production of PSA, dioscin, and relevant steroidal saponins in microbial hosts. [ABSTRACT FROM AUTHOR]

Plant derived saponins or other glycosides are widely used for their anti-inflammatory, antioxidant, and anti-viral properties in therapeutic medicine. In this study, we focus on understanding the function of the less known steroidal saponin from the roots of Liriope muscari L. H. Bailey – saponin C (also known as DT-13) in lipopolysaccharide (LPS)-stimulated RAW264.7 macrophages in comparison to the well-known saponin ginsenoside Rk1 and anti-inflammatory drug dexamethasone. We proved that DT-13 reduces LPS-induced inflammation by inhibiting nitric oxide (NO) production, interleukin-6 (IL-6) release, cycloxygenase-2 (COX-2), tumour necrosis factor-alpha (TNF-α) gene expression, and nuclear factor kappa-B (NFκB) translocation into the nucleus. It also inhibits the inflammasome component NOD-like receptor family pyrin domain containing protein 3 (NLRP3) regulating the inflammasome activation. This was supported by the significant inhibition of caspase-1 and interleukin-1 beta (IL-1β) expression and release. This study demonstrates the anti-inflammatory effect of saponins on LPS-stimulated macrophages. For the first time, an in vitro study shows the attenuating effect of DT-13 on NLRP3-inflammasome activation. In comparison to the existing anti-inflammatory drug, dexamethasone, and triterpenoid saponin Rk1, DT-13 more efficiently inhibits inflammation in the applied cell culture model. Therefore, DT-13 may serve as a lead compound for the development of new more effective anti-inflammatory drugs with minimised side effects. [Display omitted] • DT-13 inhibits LPS induced inflammation via NFκB pathway. • DT-13 mediated inhibition of NFκB translocation to nucleus alleviated inflammasome priming by LPS. • Attenuation of inflammasome related genes and caspase-1 implied the role of DT-13 in inflammasome activation. [ABSTRACT FROM AUTHOR]

Steroidal saponins were the main active constituents of the traditional medicinal herb Asparagus cochinchinensis. A phytochemical investigation of A. cochinchinensis roots led to the isolation of nine new steroidal glycosides (1–9) and seven known analogues (10–16). Their structures were established by spectroscopic analyses as well as necessary chemical evidence. [ABSTRACT FROM AUTHOR]

Sea cucumbers produce various bioactive compounds especially secondary metabolites including Saponin. The aim of this study was to investigate antibacterial activity of the Saponin extracted from the Persian Gulf sea cucumber (Stichopus hermanni) in some gram positive and negative bacteria. Extraction was first done by ethanol 70% and then Saponins were separated through column chromatography with silica gel. Extracted Saponins were identified through thin layer chromatography (TLC) and high performance thin layer chromatography (HPTLC). Minimum inhibitory concentration (MIC) and minimum bactericidal concentration (MBC) were investigated via tubular dilution. Two groups of steroidal and glycosides Saponins with Rf 0.9 and 0.05 were respectively identified in fractions extracted by TLC. HPTLC results for a sample of extracted Saponin confirmed the existence of Saponin in sea cucumber regarding the Rf. The gram negative bacterium Pseudomonas aeroginosa was the most resistant one to steroidal and glycosides- steroidal Saponins with MIC of 500 and 400 micg/ml, respectively. Steroidal and glycosides- steroidal Saponins showed no bactericidal effect in gram negative bacterium Pseudomonas aeroginosa. Among the gram positive bacteria, the highest MBC of 500 micg/ml belonged to glycosides- steroidal Saponin for Staphylococcus aureus. The higher MIC in gram negative bacteria approves the lower antibacterial property of the steroidal and glycosides Saponin extracted from sea cucumber Stichopus hermanni in these bacteria compared to the gram positive ones.

Two new steroidal saponins, β-sitosterol-3-O-α-l-glucopyranoside (3) and β-sitosterol-3-O-β-d-glucopyranosyl-(1→6)-β-d-glucopyranoside (4), were isolated and identified from the bark of Neolamarckia cadamba, along with 13 known compounds. Their structures were established on the basis of spectral data. [ABSTRACT FROM AUTHOR]

Introduction: Trillium govanianum (Nag Chhatri and Teen Patra) is traditionally used for curing joint pains, wounds, and sexual disorders. Steroidal saponins are the main active components of this species. However, only a small amount of information is available about steroidal saponins of this plant. Objective: To develop an ultra‐high‐performance liquid chromatography‐quadrupole time of flight tandem mass spectrometry (UHPLC‐QTOF‐MS/MS) and ultra‐high‐performance liquid chromatography‐evaporative light scattering detector (UHPLC‐ELSD) methods for the qualitative and quantitative determination of steroidal saponins in T. govanianum. Method: The dried rhizomes of T. govanianum (100 mg) were extracted with ethanol–water (80:20, 10 mL) by ultrasonic treatment for 30 min at 40°C. The prepared sample was analysed by UHPLC‐QTOF‐MS/MS and UHPLC‐ELSD for the qualitative and quantitative determination of steroidal saponins. Result: A total of 24 saponins were identified using UHPLC‐QTOF‐MS/MS; seven of them were characterised by comparing with standards. Furthermore, five saponins [govanoside B (2), protodioscin (6), pennogenin tetraglycosides (11), borassoside E (21) and borassoside D (24)] were quantified using UHPLC‐ELSD method in different extracts and fractions of T. govanianum. The method showed good linearity (R2 ≥ 0.993), limit of detection (0.92–4.09 μg/mL), limit of quantification (3.1–13.5 μg/mL), precision [intra‐day relative standard deviations (RSDs) < 4.3% and inter‐day RSDs < 5.5%], and accuracy (84.0–110.3%). This is the first report on the quantification of 2, 6, 11, 21 and 24 in T. govanianum. Conclusion: The present study provides an efficient analytical method for the identification and quantification of steroidal saponins and will be helpful for the quality evaluation of T. govanianum. The systematic analysis of steroidal saponins in Trillium govanianum was performed. A total of 24 saponins were tentatively identified, and their characteristic fragmentations were also summarised. Furthermore, five saponins were quantified, among them borassoside E (21), protodioscin (6) and govanoside B (2) were found most abundant and could be used as marker compounds for quality control of T. govanianum. [ABSTRACT FROM AUTHOR]

Background: Among the secondary metabolites isolated from Allium species, steroidal saponins are more important for their cytotoxic activities on a variety of cancer cell lines. Current study has investigated the cytotoxic activity of saponin-riched butanolic fraction of Allium affine, an important edible Allium species of Iran. Objective: This study was conducted to evaluate cytotoxic activity of saponin-riched fraction of Allium affine Ledeb on breast and ovarian cancer cell lines. Methods: Bulbs of the plant were extracted respectively by hexane, chloroform, chloroform-methanol (9-1) and methanol in a stepwise method with increasing solvent polarity. The methanol extract was then partitioned between water and butanol and the final dried butanolic fraction was used for further cytotoxicity assay. MCF-7, MDA-MB231 and OVCAR-3 cell lines were tested for cytotoxic activity, using different concentrations of butanolic fraction (0.1-200 µg/ml) by MTT assay. After the incubation time (48 h), the percentage of the viable cells was determined by ELISA reader instrument in 570 nm. Results: All of the cell lines tested in this investigation exhibited a dose-dependent decrease in succinate dehydrogenase activity against the control and significant dose-dependent inhibition of the growth in all concentrations and cell lines were observed (P

Tomatoes are widely consumed, however, studies on tomato seeds are limited. In this study, we isolated 11 compounds including saponins and flavonol glycosides from tomato seeds and evaluated their effects on epidermal hydration. Among the isolated compounds, tomato seed saponins (10 µM) significantly increased the mRNA expression of proteins related to epidermal hydration, including filaggrin, involucrin, and enzymes for ceramide synthesis, by 1.32- to 1.91-fold compared with the control in HaCaT cells. Tomato seed saponins (10 µM) also decreased transepidermal water loss by 7 to 13 g/m2·h in the reconstructed human epidermal keratinization (RHEK) models. Quantitative analysis of the ceramide content in the stratum corneum (SC) revealed that lycoperoside H (1–10 µM) is a promising candidate to stimulate ceramide synthesis via the upregulation of ceramide synthase-3, glucosylceramide synthase, and β-glucocerebrosidase, which led to an increase in the total SC ceramides (approximately 1.5-fold) in concert with ceramide (NP) (approximately 2-fold) in the RHEK models. Evaluation of the anti-inflammatory and anti-allergic effects of lycoperoside H demonstrated that lycoperoside H is suggested to act as a partial agonist of the glucocorticoid receptor and exhibits anti-inflammatory effects (10 mg/kg in animal test). These findings indicate that lycoperoside H can improve epidermal dehydration and suppress inflammation by increasing SC ceramide and steroidal anti-inflammatory activity.

A new steroidal saponin, 26-O-β-d-glucopyranosyl-(25R)-furost-5-ene-3β,22α,26-triol 3-O-(1−4)-β-d-glucopyranosyl-α-l-rhamnopyranosyl-(1−2)-[α-l-rhamnopyranosyl-(1−4)]-β-d-glucopyranoside [asparacochioside A (1)] was isolated from a hot water extract of the roots of Asparagus cochinchinensis, together with the known steroidal saponins protodioscin (2), methyl protodioscin (3), aspacochioside A (4), aspacochioside C (5), 15−hydroxypseudoprotodioscin (6), and chamaedroside E (7). The structure of the new compound 1 was determined by interpretation of its spectroscopic data (1D- and 2D-NMR and HR−Q−TOF−MS) and sugar analysis. The isolated compounds 1−7 were tested for their in vitro cytotoxicity against human ovarian cancer cell lines (A2780 and SKOV3). Asparacochioside A (1) exhibited a significant cytotoxicity against both A2780 and SKOV3 cells with IC50 values of 5.25 ± 2.2 and 46.82 ± 9.43 μM, respectively. Furthermore, asparacochioside A (1) significantly increased the percentage of Annexin V-positive cells (apoptotic cells), suggesting that asparacochioside A induces ovarian cancer cell death via apoptosis.

Seven steroidal saponins including three new 16,23-cyclocholestanes (1-3) and one new pregane (4) were isolated from the roots of Dracaena cambodiana Pierre ex Gagnep. Their chemical structures were elucidated to be (23R,25R)-26-O-β-D-glucopyranosyl-16,23-cyclocholesta-5,17(20)-dien-22-one-3β,16α,26-triol-3-O-α-L-rhamnopyranosyl-(1→2)-[α-L-rhamnopyranosyl-(1→3)]-β-D-glucopyranoside (1), (23R,25R)-26-O-β-D-glucopyranosyl-16,23-cyclocholesta-5,17,20(22)-trien-3β,22,26-triol-3-O-α-L-rhamnopyranosyl-(1→3)-β-D-glucopyranoside (2), (23R,25R)-16,23-cyclocholesta-5,16,20(22)-trien-3β,22,26-triol-3-O-α-L-rhamnopyranosyl-(1→3)-β-D-glucopyranoside (3), 3β-[(O-α-L-rhamnopyranosyl-(1→3)-[α-L-rhamnopyranosyl-(1→2)]-β-D-gluco-pyranosyl)oxy]-pregna-5,17(20)-diene-16-one-20-carboxylic acid 4''''-O-β-D-glucopyranosylisopentyl ester (4), cambodianoside A (5), diosbulbiside C (6), and diosbulbiside D (7), by IR, HR-ESI-MS, 1D and 2D NMR spectra. Compounds 1 and 4-7 inhibited nitric oxide (NO) production in lipopolysaccharide activated RAW 264.7 cells with IC 50 values ranging from 19.03±1.84 to 67.92±3.81 μM, whereas compounds 2 and 3 were inactive with IC 50 values over 100 μM., (© 2023 Wiley-VHCA AG, Zurich, Switzerland.)

Dracaena cambodiana Pierre ex Gagnep. is well known as a medicinal plant and widely distributed in Vietnam. Phytochemical investigation on the trunks of D. cambodiana lead to the isolation of four undescribed compounds (1-4) together with seven known ones (5-11). Their structures were determined to be pennogenin-24-yl-O-β-D-glucopyranoside (1), 17α-hydroxycambodianoside C (2), (25R)-27-hydroxypenogenin 3-O-α-L-rhamnopyranosyl-(1→3)-[α-L-rhamnopyranosyl-(1→2)]-β-D-glucopyranoside (3), (3β,25R)-17α,22α-dihydroxy-furost-5-en-3-yl-O-α-L-rhamnopyranosyl-(1→3)-[α-L-rhamnopyranosyl-(1→2)]-β-D-glucopyranoside (4), dracagenin A (5), 1-O-β-D-glucopyranosyl-2-hydroxy-4-allylbenzene (6), 1-O-α-L-rhamnopyranosyl-(1→6)-β-D-glucopyranosyl-2-hydroxy-allylbenzene (7), 2-O-α-L-rhamnopyranosyl-(1→6)-β-D-glucopyranosyl-1-hydroxy-allylbenzene (8), cinnamrutinoside A (9), icariside D1 (10), and seco-isolariciresinol 9-O-β-glucopyranoside (11) by extensive spectroscopic investigation, HR-ESI-MS, 1D and 2D NMR spectra. The anti-inflammatory activity of the isolated compounds was evaluated on macrophages. Compounds 1-6 significantly inhibited nitric oxide production in lipopolysaccharide (LPS)-induced RAW 264.7 macrophages. Among them, compound 1 showed the best inhibitory activity with an IC 50 value of 8.90±0.56 μM., (© 2023 Wiley-VHCA AG, Zurich, Switzerland.)

Allii Macrostemonis Bulbus (AMB), a traditional Chinese edible and medicinal plant, is considered beneficial to health. In this study, we isolated and purified nine steroidal saponins (compounds 1 - 9 ) from AMB. Their structures were characterized using physicochemical properties, HR-ESI-MS, 1D and 2D NMR spectroscopy. Among these compounds, compounds 1 - 5 were newly discovered named macrostemonoside U-Y, respectively. We assessed the in vitro antioxidant properties of the nine steroidal saponins through free radical scavenging and reducing power assays. This provides options for developing natural antioxidants. Additionally, an HPLC-ELSD quantitative analysis method was developed for the nine saponins in 12 batches of AMB from different origins and processing methods. The results showed that the contents of the nine steroidal saponins in AMB varied greatly among different growing environments and processing methods., Competing Interests: 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., (© 2024 The Author(s).)

Four undescribed steroidal compounds along with twenty known compounds were isolated from n-butanol extracted fraction of the whole plants of Solanum lyratum Thunb (SLNF). Their structures were assigned based on analyses of the extensive spectroscopic data (including MS, 1D/2D NMR, and ECD) or comparisons of the NMR data with those reported. Among the knowns, three compounds were isolated from Solanum plants for the first time, while one compound was isolated from S. lyratum for the first time. In addition, the cytotoxicities of these isolates against human colon SW480 and hepatoma Hep3B cells were evaluated by a MTT assay. And, nine of them and SLNF exhibited significant activities against both SW480 and Hep3B cells, while twelve of them significantly inhibited the activities of SW480 cells. This study allows for the exploitation of chemical markers with potential significance in discrimination of Solanum plants, and uncovers the diverse steroidal constituents from S. lyratum dedicated for its future application in cancer treatment., (© 2023 Wiley-VHCA AG, Zurich, Switzerland.)