Structural characterization of a new steroidal saponin from Agave angustifolia var. Marginata and a preliminary investigation of its in vivo antiulcerogenic activity and in vitro membrane permeability property

Pereira, Gabriela Moysés; Ribeiro, Marcela Gonçalves; Silva, Bernadete Pereira da; Parente, José Paz

doi:10.1016/j.bmcl.2017.08.026

Cited by 8 publications

(9 citation statements)

References 26 publications

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“…The 1 H-NMR spectrum of 3 exhibited one olefinic methine proton at δ H 5.73 (1H, br s, H-7). Four angular methyl signals at δ H 0.84 (3H, s, H-18), 1.25 (3H, s, H-19), 0.90 (3H, d, J = 7.2 Hz, H-21) and 0.86 (3H, d, J = 6.3 Hz, H-27) implied that 3 also possessed a steroidal skeleton [ 10 , 11 ]. Correspondingly, one trisubstituted olefinic group at δ C 126.59 (C-7) and 169.05 (C-8) and four angular methyl signals at δ C 17.81 (C-18), 17.83 (C-19), 9.45 (C-21), 17.64 (C-27) were discovered in the 13 C-NMR.…”

Section: Resultsmentioning

confidence: 99%

“…By extensive phytochemical and pharmacological studies, steroidal saponins have proven to be the chief active ingredients. Their significant bioactivities, including antitumor, anti-inflammatory, anti-melanogenic, antifungal, antiulcerogenic and hemostatic, have been confirmed in recent years [ 3 , 4 , 5 , 6 , 7 , 8 , 9 , 10 , 11 ]. As perennial plants, the domestic production of Rhizoma Paridis is insufficient, thus demand exceeds supply [ 2 ].…”

Section: Introductionmentioning

confidence: 99%

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New Steroidal Saponins from the Rhizomes of Paris vietnamensis and Their Cytotoxicity

Liu

Wang²,

Liu³

et al. 2018

Molecules

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Four new spirostanol saponins, named pavitnosides A–D (1–4), with six known steroidal saponins 5–10 were isolated from the rhizomes of Paris vietnamensis. Their chemical structures were determined based on extensive spectroscopic studies and chemical methods. The aglycones of pavitnoside B and pavitnoside C were not reported in previous work. The cytotoxicity of all saponins was evaluated against human glioblastoma U87MG and U251 cell lines. The new spirostanol saponin 1 displayed weak anti-proliferative activity against U87MG cell line and the known saponins 8 and 9 exhibited significant cytotoxicity against the two tumor cell lines, with IC50 values of 2.16 to 3.14 μM, but did not affect the growth of primary cultures of human astrocytes.

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Section: Resultsmentioning

confidence: 99%

Section: Introductionmentioning

confidence: 99%

New Steroidal Saponins from the Rhizomes of Paris vietnamensis and Their Cytotoxicity

Liu

Wang²,

Liu³

et al. 2018

Molecules

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“…A recent study proved that isolated glycosylated steroidal saponin from A. angustifolia marginata did not produce hemolytic alterations in gastric tissue by the presence of different glycoside chain substitutions. This structural feature also reduced the affinity of cholesterol to the erythrocytes membrane and gave a cytoprotecting effect in these cells and non-cytotoxic damage [61]. Another study assessed the effect of a methanolic extract and a saponins-enriched fraction of A. seemanniana Jacobi leaves; both reduced ulcer severity in a similar way to ranitidine at 50 mg/kg.…”

Section: Non-polar Compounds: Saponinsmentioning

confidence: 99%

Hunting Bioactive Molecules from the Agave Genus: An Update on Extraction and Biological Potential

et al. 2021

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Agaves are plants used in the production of alcoholic beverages and fibers. Ever since ancient times, pre-Hispanic cultures in Mexico have used them in traditional medicine to cure different ailments. Over the years, studies of the active principles responsible for the therapeutic benefits of agaves have increased. Leaves and fibers are the main agro-wastes generated in tequila and mezcal production, while fibers are the main waste product in the textile sector. Different investigations have referred to the agro-waste from agave processing as a source of bioactive molecules called secondary metabolites (SM). Among them, phenols, flavonoids, phytosterols, and saponins have been extracted, identified, and isolated from these plants. The role of these molecules in pest control and the prospect of metabolites with the biological potential to develop novel drugs for chronic and acute diseases represent new opportunities to add value to these agro-wastes. This review aims to update the biological activities and recent applications of the secondary metabolites of the genus Agave.

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“…Chemically, Agave plants are characterized by the production of fatty acids, alcohols, sterols, phenolic compounds, tannins, coumarins, flavones, flavonols, and homoisoflavonoids [14]. Additionally, several steroidal sapogenins and their saponins have been isolated as characteristic chemical compounds from these plants [15,16], many of which have demonstrated pharmacological effects, such as antidiabetic [17], antifungal, antibacterial, anti-inflammatory, anticarcinogenic, immunoregulatory [18], and protective, against induced gastric ulcers [19]. Agave applanata Lem.…”

Section: Introductionmentioning

confidence: 99%

Chemical Constituents from Agave applanata and Its Antihyperglycemic, Anti-inflammatory, and Antimicrobial Activities Associated with Its Tissue Repair Capability

Aguilar-Guadarrama,

Díaz-Román,

Osorio-García

et al. 2024

Planta Med

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Agave applanata is a Mexican agave whose fresh leaves are employed to prepare an ethanol tonic used to relieve diabetes. It is also applied to skin to relieve varicose and diabetic foot ulcers, including wounds, inflammation, and infections. In this study, the chemical composition of this ethanol tonic is established and its association with antihyperglycemic, anti-inflammatory, antimicrobial, and wound healing activities is discussed. The fresh leaves of A. applanata were extracted with ethanol : H2O (85 : 15). A fraction of this extract was lyophilized, and the remainder was partitioned into CH2Cl2, n-BuOH, and water. CH2Cl2 and n-BuOH fractions were subjected to a successive open column chromatography process. The structure of the isolated compounds was established using nuclear magnetic resonance and mass spectrometry spectra. The antihyperglycemic activity was evaluated through in vivo sucrose and glucose tolerance experiments, as well as ex vivo intestinal absorption and hepatic production of glucose. Wound healing and edema inhibition were assayed in mice. The minimum inhibitory concentrations (MICs) of the hydroalcoholic extract, its fractions, and pure compounds were determined through agar microdilution against the most isolated pathogens from diabetic foot ulcers. Fatty acids, β-sitosterol, stigmasterol, hecogenin (1), N-oleyl-D-glucosamine, β-daucosterol, sucrose, myo-inositol, and hecogenin-3-O-α-L-rhamnopyranosyl-(1 → 3)-β-D-xylopyranosyl-(1 → 2)-[β-D-xylopyranosyl-(1 → 3)-β-D-glucopyranosyl-(1 → 3)]-β-D-glucopyranosyl-(1 → 4)-β-D-galactopyranoside (2) were characterized. This research provides evidence for the pharmacological importance of A. applanata in maintaining normoglycemia, showing anti-inflammatory activity and antimicrobial effects against the microorganisms frequently found in diabetic foot ulcers. This plant plays an important role in wound healing and accelerated tissue reparation.

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Structural characterization of a new steroidal saponin from Agave angustifolia var. Marginata and a preliminary investigation of its in vivo antiulcerogenic activity and in vitro membrane permeability property

Cited by 8 publications

References 26 publications

New Steroidal Saponins from the Rhizomes of Paris vietnamensis and Their Cytotoxicity

New Steroidal Saponins from the Rhizomes of Paris vietnamensis and Their Cytotoxicity

Hunting Bioactive Molecules from the Agave Genus: An Update on Extraction and Biological Potential

Chemical Constituents from Agave applanata and Its Antihyperglycemic, Anti-inflammatory, and Antimicrobial Activities Associated with Its Tissue Repair Capability

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