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1.
Int J Biol Macromol ; 267(Pt 2): 131588, 2024 May.
Artículo en Inglés | MEDLINE | ID: mdl-38615860

RESUMEN

Dietary selenium (Se) supplementation has recently received increasing attention; however, Selenium nanoparticles (SeNPs) exhibit poor stability and tend to aggregate in aqueous solution. Therefore, enhancing the stability of SeNPs and their effective delivery to plants remain challenging. In this study, sodium alginate (SA) and lysozyme (LZ) were reacted via the wet-heat Maillard reaction (MR) to obtain amphiphilic alginate-based polymers (SA-LZ). Alkyl glycosides (APG) were introduced into SA-LZ to enhance the deposition of SeNPs in leaves. Thus, a renewable and degradable polysaccharide-based material (SA-LZ/APG) loaded with Se formed an amphiphilic alginate-based-based shell with a Se core. Notably, the encapsulation of SeNPs into a polysaccharide base (SA-LZ/APG) increased the stabilization of SeNPs and resulted in orange-red, zero-valent, monoclinic and spherical SeNPs with a mean diameter of approximately 43.0 nm. In addition, SA-LZ/APG-SeNPs reduced the interfacial tension of plant leaves and increased the Se content of plants compared to the blank group. In vitro studies have reported that SA-LZ/APG-SeNPs and SA-LZ-SeNPs have significantly better clearance of DDPH and ABTS than that of APG-SeNPs. Thus, we believe that SA-LZ/APG is a promising smart delivery system that can synergistically enhance the stability of SeNPs in aqueous solutions and improve the bioavailability of Se nutrient solutions.


Asunto(s)
Alginatos , Glicósidos , Nanopartículas , Selenio , Alginatos/química , Selenio/química , Nanopartículas/química , Glicósidos/química , Hojas de la Planta/química , Muramidasa/química , Tensoactivos/química , Estabilidad de Medicamentos
2.
J Nat Med ; 78(3): 741-752, 2024 Jun.
Artículo en Inglés | MEDLINE | ID: mdl-38573418

RESUMEN

In this study, nine triterpene glycosides including seven previously undescribed compounds (1-7), were isolated from leaves of Cryptolepis buchananii R.Br. ex Roem. and Schult. using various chromatographic methods. The chemical structures of the compounds were elucidated to be 3-O-ß-D-glucopyranosyl-(1 → 6)-ß-D-glucopyranosyluncargenin C 28-O-α-L-rhamnopyranosyl-(1 → 2)-ß-D-glucopyranosyl ester (1), 3-O-ß-D-glucopyranosyl-(1 → 2)-ß-D-glucopyranosyluncargenin C 28-O-α-L-rhamnopyranosyl-(1 → 2)-ß-D-glucopyranosyl ester (2), 3-O-ß-D-glucopyranosyl-(1 → 2)-ß-D-glucopyranosyluncargenin C 28-O-ß-D-glucopyranosyl-(1 → 4)-α-L-rhamnopyranosyl-(1 → 2)-ß-D-glucopyranosyl ester (3), 3-O-ß-D-glucopyranosyl-(1 → 2)-ß-D-glucopyranosylhederagenin 28-O-α-L-rhamnopyranosyl-(1 → 2)-ß-D-glucopyranosyl ester (4), 3-O-ß-D-glucopyranosylarjunolic acid 28-O-α-L-rhamnopyranosyl-(1 → 2)-ß-D-glucopyranosyl ester (5), 3-O-ß-D-glucopyranosyl-(1 → 2)-ß- D-glucopyranosyl-6ß,23-dihydroxyursolic acid 28-O-α-L-rhamnopyranosyl-(1 → 2)-ß-D-glucopyranosyl ester (6), 3-O-ß-D-glucopyranosyl-6ß,23-dihydroxyursolic acid 28-O-α-L-rhamnopyranosyl-(1 → 2)-ß-D-glucopyranosyl ester (7), asiatic acid 28-O-α-L-rhamnopyranosyl-(1 → 2)-ß-D-glucopyranosyl ester (8), and 3-O-ß-D-glucopyranosylasiatic acid 28-O-α-L-rhamnopyranosyl-(1 → 2)-ß-D-glucopyranosyl ester (9), through infrared, high-resolution electrospray ionization mass spectrometry, one- and two-dimensional nuclear magnetic resonance spectral analyses. The isolates inhibited nitric oxide production in lipopolysaccharide-activated RAW 264.7 cells, with half-maximal inhibitory concentration (IC50) values of 18.8-58.5 µM, compared to the positive control compound, dexamethasone, which exhibited an IC50 of 14.1 µM.


Asunto(s)
Glicósidos , Óxido Nítrico , Hojas de la Planta , Triterpenos , Triterpenos/química , Triterpenos/farmacología , Triterpenos/aislamiento & purificación , Óxido Nítrico/metabolismo , Glicósidos/química , Glicósidos/farmacología , Glicósidos/aislamiento & purificación , Ratones , Animales , Estructura Molecular , Hojas de la Planta/química , Células RAW 264.7 , Extractos Vegetales/química , Extractos Vegetales/farmacología
3.
J Nat Med ; 78(3): 709-721, 2024 Jun.
Artículo en Inglés | MEDLINE | ID: mdl-38575838

RESUMEN

Methanol extract of the Cnidium officinale Makino rhizome, which is used as a crude drug Cnidium Rhizome (Cnidii Rhizoma; "Senkyu" in Japanese) and is listed in the Japanese Pharmacopoeia XVIII, showed intracellular triglyceride metabolism-promoting activity in high glucose-pretreated HepG2 cells. Thirty-five constituents, including two new alkylphthalide glycosides, senkyunosides A (1) and B (2), and a neolignan with a new stereoisomeric structure (3), were isolated in the extract. Their stereostructures were elucidated based on chemical and spectroscopic evidence. Among the isolates, several alkylphthalides, (Z)-3-butylidene-7-methoxyphthalide (9) and senkyunolides G (10), H (14), and I (15), and a polyacetylene falcarindiol (26), were found to show significant activity without any cytotoxicity at 10 µM.


Asunto(s)
Benzofuranos , Cnidium , Rizoma , Triglicéridos , Humanos , Rizoma/química , Células Hep G2 , Cnidium/química , Triglicéridos/metabolismo , Benzofuranos/farmacología , Benzofuranos/química , Benzofuranos/aislamiento & purificación , Estructura Molecular , Extractos Vegetales/farmacología , Extractos Vegetales/química , Glicósidos/farmacología , Glicósidos/química , Glicósidos/aislamiento & purificación
4.
J Ethnopharmacol ; 328: 118051, 2024 Jun 28.
Artículo en Inglés | MEDLINE | ID: mdl-38493905

RESUMEN

ETHNOPHARMACOLOGICAL RELEVANCE: Traditionally, the plant Morinda longissima Y.Z.Ruan (Rubiaceae) is used by ethnic people in Vietnam for the treatment of liver diseases and hepatitis. AIM OF THE STUDY: The study was designed to assess the efficacy of the 95% ethanolic extract of Morinda longissima roots (MLE) in experimental immune inflammation. The phytochemical variation of root extract and the chemical structures of natural compounds were also investigated using HPLC-DAD-HR-MS analysis. MATERIALS AND METHODS: Three different doses (100, 200, and 300 mg/kg b.w.) of MLE were chosen to determine anti-inflammatory activity. The mice were given orally extracts and monitored their behavior and mortality for 14 days to evaluate acute toxicity. The volume of the paw and the histopathological evaluation were carried out. The polyphenolic phytoconstituents of MLE extract were identified using LC/MS analysis. The anti-inflammatory efficacy in silico and molecular docking simulations of these natural products were evaluated based on their cyclooxygenase (COX)-1 and 2 inhibitory effects. RESULTS: This investigation showed the 95% ethanolic extract of Morinda longissima roots was found non-toxic up to 2000 mg/kg dose level in an acute study, neither showed mortality nor treatment-related signs of toxicity in mice. Eight anthraquinones and anthraquinone glycosides of Morinda longissima roots were identified by HPLC-DAD-HR-MS analysis. In the in vivo experiments, MLE was found to possess powerful anti-inflammatory activities in comparison with diclofenac sodium. The highest anti-inflammatory activity of MLE in mice was observed at a dose of 300 mg/kg body weight. The in silico analysis showed that seven out the eight anthraquinones and anthraquinone glycosides possess a selectivity index RCOX-2/COX-1 lower than 1, indicating that these compounds are selective against the COX-2 enzyme in the following the order: rubiadin-3-methyl ether < morindone morindone-6-methyl ether < morindone-5-methyl ether < damnacanthol < rubiadin < damnacanthol-3-O-ß-primeveroside. The natural compounds with the best selectivity against the COX-2 enzyme are quercetin (9), rubiadin-3-methyl ether (7), and morindone (4), with RCOX2/COX1 ratios of 0.02, 0.03, and 0.19, respectively. When combined with the COX-2 protein in the MD research, quercetin and rubiadin-3-methyl ether greatly stabilized the backbone proteins and ligands. CONCLUSION: In conclusion, the anthraquinones and ethanolic extract of Morinda longissima roots may help fight COX-2 inflammation. To develop novel treatments for inflammatory disorders linked to this one, these chemicals should be investigated more in the future.


Asunto(s)
Éteres Metílicos , Morinda , Rubiaceae , Humanos , Ratones , Animales , Morinda/química , Rubiaceae/química , Simulación del Acoplamiento Molecular , Ciclooxigenasa 2 , Quercetina/análisis , Raíces de Plantas/química , Antraquinonas/farmacología , Antraquinonas/uso terapéutico , Extractos Vegetales/uso terapéutico , Extractos Vegetales/toxicidad , Antiinflamatorios/farmacología , Antiinflamatorios/uso terapéutico , Antiinflamatorios/análisis , Glicósidos/química , Inflamación/tratamiento farmacológico , Éteres Metílicos/análisis , Fitoquímicos/uso terapéutico , Fitoquímicos/toxicidad
5.
J Nat Med ; 78(3): 525-536, 2024 Jun.
Artículo en Inglés | MEDLINE | ID: mdl-38457082

RESUMEN

Ipomoea muricata (L.) Jacq. seeds (Convolvulaceae) are used as a traditional laxative and carminative medicine. Muricatins XIV (1), XV (2), XVI (3), and XVII (4), were isolated from I. muricata seeds as four new resin glycosides, along with seven known compounds, three of which were isolated for the first time as natural products; their structures were determined using MS and NMR spectroscopy. Compounds 1-4 are macrolactones (jalapins); the sugar moieties of 1, 2, and 4 are partially acylated with 2S-methylbutyric acid, while that of 3 is esterified with 2S-methylbutyric and 2S-methyl-3S-hydroxybutyric acids. In addition, the antiviral activities of the seven compounds obtained in this study, together with five known compounds obtained in our previous study into resin glycosides from I. muricata seeds, were evaluated against herpes simplex virus type 1 (HSV-1); their cytotoxicities against HL-60 human promyelocytic leukemia cells were also investigated. All examined jalapins exhibited similar or slightly weaker anti-HSV-1 activities than acyclovir, the positive control; however, the glycosidic acid of 4 was inactive, while its methyl ester was weakly active. On the other hand, cytotoxicity testing against HL-60 cells showed similar results to those observed during anti-HSV-1 activity testing, with the exception that one jalapin was less active.


Asunto(s)
Antivirales , Glicósidos , Ipomoea , Resinas de Plantas , Semillas , Ipomoea/química , Semillas/química , Glicósidos/farmacología , Glicósidos/química , Glicósidos/aislamiento & purificación , Humanos , Resinas de Plantas/química , Antivirales/farmacología , Antivirales/química , Antivirales/aislamiento & purificación , Estructura Molecular , Herpesvirus Humano 1/efectos de los fármacos , Células HL-60 , Extractos Vegetales/química , Extractos Vegetales/farmacología , Espectroscopía de Resonancia Magnética
6.
J Ethnopharmacol ; 327: 117982, 2024 Jun 12.
Artículo en Inglés | MEDLINE | ID: mdl-38423411

RESUMEN

ETHNOPHARMACOLOGICAL RELEVANCE: Cynanchum otophyllum C.K.Schneid.PI.Wilson, commonly referred as ''Qingyangshen'' (QYS), is a traditional folk medicine from Yunnan, renowned for its efficacy in neurological and psychiatric disorders. Glycosides isolated from QYS have shown promise in alleviating epilepsy, however, mechanisms of action and specific molecular targets remain to be elucidated. AIM OF THE STUDY: The study aimed to evaluate the anticonvulsant effects of Qingyangshen glycosides M1 (M1), a C21 steroidal glycoside from QYS, on pentylenetetrazol (PTZ)-induced convulsions in zebrafish (Danio rerio), and its neuroprotective effect on Glutamate (Glu)-induced damage to PC12 cells, and importantly to identify its potential molecular targets. MATERIALS AND METHODS: To evaluate anticonvulsant activity of M1, 7 days-post-fertilization (7-dpf) animals were pretreated (by immersion) and then exposed to PTZ (10 mM) solution. Furthermore, Glu-induced PC12 cell damage was employed to investigate the neuroprotective and anti-apoptotic capacity. Cells were pretreated with various concentrations of M1 (0-10 µM) for 12 h and then co-treated with Glu (15 mM) for an additional 24 h. The cell viability, apoptosis rate and apoptosis-related proteins (p-PI3K, PI3K, Akt, p-Akt, CREB, p-CREB, BDNF, Bax and Bcl-2) were measured using CCK-8, annexin V/PI and Western blot assays. To model the expected interaction between M1 and candidate cannabinoid receptor type 1 (CB1R), ERK phosphorylation, molecular docking, and drug affinity responsive target stability (DARTS) techniques were employed. Finally, CB1R antagonist Rimonabant (Rim) was validated by co-administration in both zebrafish and cells to confirm the requirement of CB1R for M1 efficacy. RESULTS: At a concentration of 400 µM, M1 dramatically reversed PTZ-induced convulsive-like behaviors in zebrafish, as evidenced by a significant reduction in locomotor activity. In the context of Glu-induced cytotoxicity, M1 (10 µM) demonstrated a notable increase in cell viability and suppressed apoptosis through modulation of the Bax/Bcl-2 ratio and activation of the PI3K/Akt/CREB/BDNF signaling axis. These effects were facilitated through CB1R activation. In contrast, Rim dampened the beneficial activities of M1 as a cannabinoid agonist. CONCLUSIONS: These results demonstrated that M1 as a potential CB1R activator, exhibiting anticonvulsive effects in a PTZ-induced zebrafish model and neuroprotective properties via the PI3K/Akt/CREB/BDNF signaling axis in a Glu-induced PC12 cell injury model. Notably, the observed seizure relief attenuated by CB1R chemical antagonism.


Asunto(s)
Fármacos Neuroprotectores , Proteínas Proto-Oncogénicas c-akt , Humanos , Ratas , Animales , Proteínas Proto-Oncogénicas c-akt/metabolismo , Glicósidos/farmacología , Glicósidos/uso terapéutico , Glicósidos/química , Pez Cebra , Anticonvulsivantes/farmacología , Anticonvulsivantes/uso terapéutico , Fosfatidilinositol 3-Quinasas/metabolismo , Proteína X Asociada a bcl-2 , Factor Neurotrófico Derivado del Encéfalo/metabolismo , Simulación del Acoplamiento Molecular , China , Convulsiones/inducido químicamente , Convulsiones/tratamiento farmacológico , Convulsiones/metabolismo , Proteínas Reguladoras de la Apoptosis , Apoptosis , Proteínas Proto-Oncogénicas c-bcl-2 , Pentilenotetrazol/toxicidad , Fármacos Neuroprotectores/farmacología , Fármacos Neuroprotectores/uso terapéutico
7.
Biomed Chromatogr ; 38(5): e5838, 2024 May.
Artículo en Inglés | MEDLINE | ID: mdl-38342982

RESUMEN

Strobilanthes sarcorrhiza (CTS) is a medicinal plant with various pharmacological effects such as tonifying kidney and anti-inflammatory. However, the chemical composition and difference of its four parts (leaves, stems, rhizomes, and root tubers) have been rarely reported. In this study, ultrafast flow liquid chromatography coupled with quadrupole-time-of-flight MS was applied to analyze the chemical profile of CTS and identify 55 compounds, including terpenoids, phenylethanol glycosides, fatty acid derivatives, chain glycosides, flavonoid glycosides, and others. Among these compounds, 34 compounds were first identified in CTS. They were mainly terpenoids, phenylethanol glycosides, fatty acid derivatives, and so forth. Multivariate statistical analysis, such as principal component analysis and orthogonal partial least squares-discriminant analysis were also used to evaluate the difference in chemical compounds from the four parts of CTS. The results showed that phenylethanol glycosides were the main compounds of the underground parts, while terpenoids were the main compounds of the aboveground parts. This study revealed the chemical diversity and similarity of CTS and suggested that the rhizomes could be used as an alternative medicinal part to improve the resource utilization of CTS.


Asunto(s)
Espectrometría de Masas , Análisis Multivariante , Espectrometría de Masas/métodos , Cromatografía Liquida/métodos , Extractos Vegetales/química , Terpenos/análisis , Terpenos/química , Glicósidos/análisis , Glicósidos/química , Cromatografía Líquida de Alta Presión/métodos
8.
Chin J Nat Med ; 22(2): 161-170, 2024 Feb.
Artículo en Inglés | MEDLINE | ID: mdl-38342568

RESUMEN

Our continued works on the chemical constituents of Ginkgo biloba (G. biloba) leaves has led to the isolation of two novel phenylbutenoids (1, 2), along with five previously unidentified terpene glycosides (3-7). Among them, compounds 1 and 2 represent unique (Z)-phenylbutenoids, 3-6 are megastigmane glycosides, and 7 is identified as a rare bilobanone glycoside (Fig. 1). This study marks the first reported isolation of phenylbutenoid and bilobanone glycoside from G. biloba. The chemical structures of these compounds were elucidated through extensive spectroscopic analysis, including HR-ESI-MS and various 1D and 2D NMR experiments. Furthermore, the absolute configurations of these molecules were determined using Mosher's method, ECD experiments, and Cu-Kα X-ray crystallographic analyses.


Asunto(s)
Glicósidos Cardíacos , Glicósidos , Glicósidos/química , Ginkgo biloba/química , Terpenos/química , Hojas de la Planta/química , Extractos Vegetales/química
9.
J Vis Exp ; (204)2024 Feb 02.
Artículo en Inglés | MEDLINE | ID: mdl-38372350

RESUMEN

The separation and analysis of the desired chemical components are important subjects for the fundamental research of traditional Chinese medicine (TCM). Ultra-high-performance liquid chromatography quadrupole time-of-flight tandem mass spectrometry (UPLC-Q-TOF-MS/MS) has gradually become a leading technology for the identification of TCM ingredients. Gynura bicolor DC. (BFH), a perennial stemless herb used for medicine and food in China has medicinal effects such as clearing heat, moistening the lung, relieving cough, dispersing stasis, and relieving swelling. Polyphenols and flavonoids contain numerous isomers, which hinder the identification of the complex compounds in BFH. This paper presents a systematic protocol for studying chemical constituents of BFH based on solvent extraction and integrated data via UPLC-Q-TOF-MS. The method described here includes systematic protocols for sample pretreatment, MS calibration, MS acquisition, data processing, and analysis of results. Sample pretreatment includes collection, cleaning, drying, crushing, and extraction. MS calibration consists of multipoint and single-point correction. Data processing includes data importing, method establishment, analysis processing, and result presentation. Representative results of the typical fragmentation pattern of phenolic acids, esters, and glycosides in Gynura bicolor DC. (BFH) are presented in this paper. In addition, organic solvent selection, extraction, data integration, collision energy selection, and method improvement are discussed in detail. This universal protocol can be widely used to identify complex compounds in TCM.


Asunto(s)
Medicamentos Herbarios Chinos , Espectrometría de Masas en Tándem , Humanos , Espectrometría de Masas en Tándem/métodos , Medicina Tradicional China , Glicósidos/análisis , Glicósidos/química , Cromatografía Líquida de Alta Presión/métodos , Solventes
10.
Phytochemistry ; 219: 113985, 2024 Mar.
Artículo en Inglés | MEDLINE | ID: mdl-38237845

RESUMEN

Ornithogalum thyrsoides Jacq belongs to the Asparagaceae family and is cultivated for ornamental purposes. The authors have previously reported several cholestane- and spirostan-type steroidal glycosides from O. thyrsoides. Conventional TLC analysis of the methanolic bulb extract of O. thyrsoides suggested the presence of unprecedented compounds; therefore, a detailed phytochemical investigation of the extract was performed and 35 steroidal glycosides (1-35), including 21 previously undescribed ones (1-21) were collected. The structures of 1-21 were determined mainly by analyses of their 1H and 13C NMR spectra with the aid of two-dimensional NMR spectroscopy. The isolated compounds were classified into three distinct groups: furostan-type (1, 2, 8-12, and 22), spirostan-type (3-7 and 23-26), and cholestane-type (13-21 and 27-35). Although the C/D-ring junction of the steroidal skeleton is typically trans-oriented, except for some cardiotonic and pregnane-type steroidal derivatives, 7 possess a cis C/D-ring junction. This is the first reported instance of such a configuration in spirostan-type steroidal derivatives, marking it as a finding of significant interest. Compounds 1-35 were evaluated for cytotoxicity against HL-60 human promyelocytic leukemia cells and SBC-3 human small-cell lung cancer cells. Compounds 3-6, 9, 17-21, 23-25, and 30-35 demonstrated cytotoxicity in a dose-dependent manner with IC50 values ranging from 0.000086 to 18 µM and from 0.00014 to 37 µM toward HL-60 and SBC-3 cells, respectively. Compound 19, which is obtained in a good yield and shows relatively potent cytotoxicity among the undescribed compounds, induces apoptosis in HL-60 cells, accompanied by arresting the cell cycle of HL-60 cells at the G2/M phase. In contrast, 19 causes oxidative stress-associated necrosis in SBC-3 cells. The cytotoxic mechanism of 19 is different between HL-60 and SBC-3 cells.


Asunto(s)
Colestanos , Leucemia , Neoplasias Pulmonares , Ornithogalum , Espirostanos , Humanos , Células HL-60 , Ornithogalum/química , Glicósidos/química , Colestanos/química , Esteroides/farmacología , Esteroides/química , Extractos Vegetales/farmacología
11.
Fitoterapia ; 173: 105822, 2024 Mar.
Artículo en Inglés | MEDLINE | ID: mdl-38224899

RESUMEN

One new phenolic cyclobutantetraol ester united chromone glycoside (1), one new amide (2), and three new phenyl ethanol glycosides (3-5) were obtained from the water extract of Scindapsus officinalis (Roxb.) Schott, in which compound 1 was the first reported structure incorporating the phenolic cyclobutantetraol ester and chromone via the glucose phenolic metabolites in nature. Structures of the isolated compounds, including absolute configurations, were elucidated according to the analysis of HRESIMS, NMR, ECD and BLYP/6-31G* geometry optimization calculations of 13C NMR data. All isolates (1-5) were evaluated for the antidiabetic activity by the insulin resistance (IR) model and anti-inflammatory activity against NO production in vitro. Compounds 1-3 showed strong antidiabetic activities, greatly promoting the glucose consumption in the insulin resistance HepG2 cells compared with the model group, however, 1-5 showed weak anti-inflammatory activities.


Asunto(s)
Hipoglucemiantes , Resistencia a la Insulina , Humanos , Hipoglucemiantes/farmacología , Estructura Molecular , Glicósidos/química , Cromonas , Antiinflamatorios/farmacología , Antiinflamatorios/química , Fenoles , Ésteres , Glucosa
12.
Int J Mol Sci ; 25(2)2024 Jan 19.
Artículo en Inglés | MEDLINE | ID: mdl-38279268

RESUMEN

Nymphoides peltata has been used as a medicinal herb in traditional medicines to treat strangury, polyuria, and swelling. The phytochemical investigation of the MeOH extract of N. peltata roots led to the isolation of three iridoid glycosides and three coumarin glycoside derivatives, which were characterized as menthiafolin (1), threoninosecologanin (2), callicoside C (3), and scopolin (4), as well as two undescribed peltatamarins A (5) and B (6). The chemical structures of the undescribed compounds were determined by analyzing their 1 dimensional (D) and 2D nuclear magnetic resonance (NMR) spectra and using high-resolution (HR)-electrospray ionization mass spectroscopy (ESI-MS), along with the chemical reaction of acid hydrolysis. The wound healing activities of the isolated compounds 1-6 were evaluated using a HaCaT cell scratch test. Among the isolates, scopolin (4) and peltatamarin A (5) promoted HaCaT cell migration over scratch wounds, and compound 5 was the most effective. Furthermore, compound 5 significantly promoted cell migration without adversely affecting cell proliferation, even when treated at a high dose (100 µM). Our results demonstrate that peltatamarin A (5), isolated from N. peltata roots, has the potential for wound healing effects.


Asunto(s)
Glicósidos Cardíacos , Magnoliopsida , Plantas Medicinales , Glicósidos/farmacología , Glicósidos/química , Glicósidos Iridoides/química , Cicatrización de Heridas , Extractos Vegetales/farmacología , Extractos Vegetales/química , Cumarinas/farmacología
13.
Fitoterapia ; 173: 105808, 2024 Mar.
Artículo en Inglés | MEDLINE | ID: mdl-38168567

RESUMEN

Four new steroidal glycosides (1-4), including two steroidal saponins named lililancifoloside B and C (1-2), one pregnane glycoside named lililancifoloside D (3), and one C22-steroidal lactone glycoside named lililancifoloside E (4), together with five known ones (5-9), were isolated from the bulbs of Lilium lancifolium Thunb. By using spectroscopic analysis, including 1D, 2D NMR, and HR-ESI-MS, the structures of 1-4 were elucidated. All isolates were tested for their cytotoxic potential against the MCF-7, MDA-MB-231, HepG2, and A549 cell lines. Compound 6 distinguished out among them, IC50 values of 3.31, 5.23, 1.78, and 1.49 µM against the four cell lines, respectively. Other compounds such as compound 3, 5, and 9 have also shown specific cytotoxic activity. Next, studies showed that compound 6 might cause HepG2 cells to undergo a cell cycle arrest during the G2/M phase and apoptosis.


Asunto(s)
Lilium , Saponinas , Lilium/química , Estructura Molecular , Glicósidos/farmacología , Glicósidos/química , Saponinas/farmacología , Extractos Vegetales/química
14.
J Nat Med ; 78(2): 403-410, 2024 Mar.
Artículo en Inglés | MEDLINE | ID: mdl-38238611

RESUMEN

Morin is a flavonol having 2',4'-dihydroxy group on B-ring identified especially in Moraceae plants. While morin is widely known, its glycosides are relatively rare. To the best of our knowledge, morin-3-O-glucoside (1) was first reported in 2008. However, the reported chemical shift values of 1 were unsatisfactory with those of the aglycone, morin, which is rather similar to quercetin-3-O-glucoside (2). Therefore, we prepared morin-3-O-glucoside (1) by microbial transformation of morin with Cunninghamella sp., and the NMR assignment was reinvestigated. The microbial culture also produced another compound (3). The NMR and MS analyses of 3 revealed it as a novel compound, morin-2'-O-glucoside (3).In this study, the revision of the NMR assignment of morin-3-O-glucoside (1), and the preparation and structural elucidation of a novel compound, morin-2'-O-glucoside (3), were described.


Asunto(s)
Flavonas , Flavonoides , Glucósidos , Flavonoides/química , Glucósidos/química , Glicósidos/química , Flavonoles
15.
Nat Prod Res ; 38(6): 994-1001, 2024 Mar.
Artículo en Inglés | MEDLINE | ID: mdl-37157866

RESUMEN

Phytochemical study on the rhizomes of Kaempferia parviflora led to the isolation of twenty-three compounds including six phenolic glycosides (1-6), thirteen flavones (7-19), and five phenolic compounds (20-23). Of these, the new compounds were determined to be 2,4-dihydroxy-6-methoxyacetophenone-2-ß-D-apiofuranosyl-(1→6)-ß-D-glucopyranoside (1), 2-hydroxy-4-propionyl-phenyl O-ß-D-glucopyranoside (2), and 4-hydroxy-3,5-dimethoxyacetophenone 8-O-α-L-rhamnopyranosyl-(1→6)-ß-D-glucopyranoside (3) and named as kaempanosides A-C, respectively. Their chemical structures were established based on HR-ESI-MS, 1D and 2D NMR spectra. All compounds 1-23 exhibited acetylcholinesterase inhibitory activity with IC50 values ranging from 57.76 to 253.31 µM.


Asunto(s)
Flavonas , Zingiberaceae , Acetilcolinesterasa/análisis , Rizoma/química , Flavonas/farmacología , Extractos Vegetales/química , Glicósidos/química , Zingiberaceae/química
16.
Fitoterapia ; 172: 105740, 2024 Jan.
Artículo en Inglés | MEDLINE | ID: mdl-37939734

RESUMEN

Three new phenolic glycosides (1-3) and a new lignan glycoside (4), together with five known compounds (5-9) were isolated from the ethanol extract of the aerial part of Gaultheria leucocarpa var. yunnanensis (Franch.) T.Z.Hsu & R.C.Fang. Their structures were determined on the basis of spectroscopic techniques, experimental and calculated ECD spectra, acid hydrolysis, and enzymatic hydrolysis experiments. All the isolates were evaluated for their anti-inflammatory and antioxidant activities. Compounds 7 and 8 exhibited inhibitory effects against the LPS-induced production of NO with IC50 of 63.71 and 10.66 µM, respectively, compared to L-NMMA having an IC50 of 6.95 µM. Besides, compound 7 also represented significant DPPH radical scavenging activity with EC50 of 18.75 µM, comparable with vitamin C (EC50 = 15.77 µM).


Asunto(s)
Glicósidos Cardíacos , Gaultheria , Lignanos , Glicósidos/química , Lignanos/farmacología , Gaultheria/química , Estructura Molecular , Antiinflamatorios/farmacología , Antiinflamatorios/química
17.
Fitoterapia ; 172: 105736, 2024 Jan.
Artículo en Inglés | MEDLINE | ID: mdl-37939735

RESUMEN

Four rare compounds (1-4), including one 1,4-epoxy-benzoxepane derivative and one ringed prenylated naphthoquinoid skeleton, as well as one isopimarane-type diterpenoid and one megastigmane-type glycoside, along with three known megastigmane-type glycosides (5-7) were isolated from the ethanol extracts of C. chinense. Their structures were determined on the basis of 1D, 2D NMR, HR-ESI-MS and DP4+ analysis. Meanwhile, the in vitro evaluation indicated that compound 2 and 6 exhibited excellent procoagulant activities, which can significantly shorten prothrombin time (PT) and activated partial thromboplastin time (APTT), respectively.


Asunto(s)
Lamiaceae , Norisoprenoides , Estructura Molecular , Lamiaceae/química , Glicósidos/química
18.
Nat Prod Res ; 38(6): 1016-1023, 2024 Mar.
Artículo en Inglés | MEDLINE | ID: mdl-37194669

RESUMEN

A novel bioactive flavan glycoside was isolated by solvent extraction method with the help of Soxhlet apparatus from the methanolic extract of Tradescantia spathacea Sw. Flavan glycoside having molecular formula C20H22O10, melting point 175-1780C, molecular weight by ESI-MS m/z (M + H]+ 423, optical rotation was[α]21D-45.1(c 0.20 methanol). Its structure was determined (-)-epicatechin 7-O-alpha-L-arabinopyranoside. Various color reactions, chemical degradation (like acid hydrolysis, permethylation, and enzymatic hydrolysis), UV-Visible spectrophotometry, Fourier transforms infrared spectroscopy, electrospray ionization mass spectrometry, and nuclear magnetic resonance spectroscopy were used to establish the structure of compound (-)-(-)-epicatechin 7-O-alpha-L-arabinopyranoside.. A flavan glycoside was also tested with a DPPH assay method for antioxidant activity by using Ascorbic acid as standard. DPPH radical scavenging test data demonstrate that a flavan glycoside possesses potent antioxidant activity so this flavan glycoside can be utilized as a potent antioxidant agent.


Asunto(s)
Glicósidos Cardíacos , Catequina , Commelinaceae , Tradescantia , Antioxidantes/farmacología , Glicósidos/química , Extractos Vegetales/química , Espectrometría de Masa por Ionización de Electrospray
19.
Biol Trace Elem Res ; 202(5): 2111-2123, 2024 May.
Artículo en Inglés | MEDLINE | ID: mdl-37612486

RESUMEN

Tripterygium glycosides (TG) can seriously damage male reproductive function, and the reproductive system is difficult to restore after stopping the administration of TG in male rats. Zinc (Zn) is one of the most important trace elements in the human body and plays an important role in maintaining male fertility. The aim of this study was to investigate whether zinc supplementation could improve the testicular reproductive damage induced by TG toxicity in rats and to investigate its mechanism of action. The results showed that zinc sulfate (ZnSO4) could improve testicular tissue structure and semen parameters, promote testosterone synthesis, increase zinc-containing enzyme activity, increase zinc concentration in serum and testicular tissues, and maintain zinc homeostasis in male rats induced by TG toxicity. Zinc supplementation activated relevant signalling molecules in the KEAP1-NRF2/ARE pathway and alleviated TG-induced oxidative stress. Therefore, this study concluded that zinc supplementation could improve reproductive damage by regulating zinc homeostasis and the expression of genes related to oxidative stress.


Asunto(s)
Glicósidos , Tripterygium , Humanos , Ratas , Masculino , Animales , Glicósidos/farmacología , Glicósidos/química , Tripterygium/química , Proteína 1 Asociada A ECH Tipo Kelch , Zinc/farmacología , Factor 2 Relacionado con NF-E2/genética , Testículo , Estrés Oxidativo , Homeostasis
20.
Arch Pharm (Weinheim) ; 357(2): e2300438, 2024 Feb.
Artículo en Inglés | MEDLINE | ID: mdl-37984852

RESUMEN

Ifosfamide (IFOS) is a broad-spectrum chemotherapeutic agent that has been extensively used for breast cancer and other solid tumors. Unfortunately, its use is associated with toxicities of several organs. Stenocarpus sinuatus is an Australian tree belonging to the Proteaceae family. In the current study, the phytochemical constituents of S. sinuatus methanol leaf extract (SSLE) were assessed. In addition, the protective effect of SSLE against IFOS-induced nephrotoxicity and hepatotoxicity was evaluated. Rats were randomly divided into six groups: control, IFOS (50 mg/kg), IFOS + SSLE (100 mg/kg), IFOS + SSLE (200 mg/kg), IFOS + SSLE (400 mg/kg), and SSLE (400 mg/kg). Hepatoprotective and nephroprotective potency of SSLE was assessed using different biochemical parameters. The phytochemical investigation resulted in the isolation of four flavonoid glycosides (kaempferol 3-O-ß- d-glucopyranosyl-(1→2)-α- l-rhamnopyranoside, kaempferol 3-O-α-rhamnopyranoside, isorhamnetin 3-O-ß- d-glucopyranosyl-(1→2)-α- l-rhamnopyranoside, and quercetin 3-O-ß- d-glucopyranosyl-(1→2)-α- l-rhamnopyranoside) and a coumarin (scopoletin). This is the first report on the isolated compounds from the genus Stenocarpus. SSLE showed enhancement of kidney and liver functions and reduction of oxidative stress and inflammation. The histopathology of the investigated organs confirmed the protective effect of SSLE. In conclusion, SSLE is considered as a promising candidate that can be used in defense against the toxic effects of IFOS after further clinical trials.


Asunto(s)
Ifosfamida , Quempferoles , Ratas , Animales , Quempferoles/farmacología , Ifosfamida/toxicidad , Relación Estructura-Actividad , Australia , Flavonoides/química , Glicósidos/química , Glicósidos/farmacología , Extractos Vegetales/farmacología , Metanol , Fitoquímicos
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