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1.
Phytochemistry ; 195: 113073, 2022 Mar.
Artigo em Inglês | MEDLINE | ID: mdl-34974412

RESUMO

Six flavonoids, namely, three undescribed biflavonoids, one undescribed 8-aryl flavonoid, and two known compounds, were isolated from Selaginella tamariscina (P.Beauv.) Spring. The structures and absolute configurations of those undescribed compounds were established by NMR spectroscopy data, HRESIMS analyses and electronic circular dichroism (ECD) analyses. In addition, all the isolates were evaluated for their hypoglycemic activity in HepG2 cells. Involvenflavone H, I, and J significantly increased glucose consumption in both normal and insulin-resistant HepG2 cells. Interestingly, these three compounds can effectively upregulate the protein expression of glucokinase (GCK) and adenylate cyclases (ADCYs). These results suggested that involvenflavone H, I, and J (especially involvenflavone J) may have potent hypoglycemic activity, which also provided promising molecular targets for the treatment of diabetes.


Assuntos
Selaginellaceae , Flavonoides/farmacologia , Hipoglicemiantes/farmacologia , Insulina , Estrutura Molecular
2.
J Agric Food Chem ; 70(2): 615-625, 2022 Jan 19.
Artigo em Inglês | MEDLINE | ID: mdl-35005957

RESUMO

A total of 11 new (1-11) and 2 known (12 and 13) ent-kaurane diterpene derivatives were identified from the roasted beans of Coffea cultivar S288. Their structures were established by extensive spectroscopic analysis, including one- and two-dimensional nuclear magnetic resonance (heteronuclear single-quantum correlation, heteronuclear multiple-bond correlation, correlation spectroscopy, and rotating-frame Overhauser enhancement spectroscopy), high-resolution electrospray ionization mass spectrometry, and X-ray analyses. Cafespirone acid A (1) represents the first example of diterpene featuring a spirocyclic skeleton constructed from a 6/6/5 tricyclic system. Cafeane acid A (2) possesses a 6/6/6/5 tetracyclic system as a result of the C/D ring rearrangement. Furthermore, compounds 1-12 were evaluated for their α-glucosidase inhibitory activity. The results showed that compounds 2, 4, 5, 6, 7, 10, and 11 had a moderate inhibitory effect on α-glucosidase, and half-maximal inhibitory concentration values of compounds 4, 6, 7, and 10 were 18.76 ± 1.46, 4.88 ± 0.03, 12.35 ± 0.91, and 12.64 ± 0.59 µM, respectively, compared to the positive control acarbose (60.71 ± 16.45 µM). Additionally, the molecular docking experiments showed that the carbonyl group at C-19 of compounds 4, 6, and 7 formed strong hydrogen bonds with ARG315, which may make them have moderate inhibitory activity.


Assuntos
Coffea , Diterpenos do Tipo Caurano , Diterpenos , Coffea/metabolismo , Café , Espectroscopia de Ressonância Magnética , Simulação de Acoplamento Molecular , Estrutura Molecular , alfa-Glucosidases/metabolismo
3.
Chem Pharm Bull (Tokyo) ; 70(1): 25-31, 2022.
Artigo em Inglês | MEDLINE | ID: mdl-34980729

RESUMO

We report on the recommendation of the simple and versatility of methylated reference (MR) to improve applications in the single reference (SR)-LC based on relative molar sensitivity (RMS). Three curcuminoids (Curs) such as curcumin, demethoxycurcumin and bisdemethoxycurcumin in turmeric products were determined using authentic standards and methylated curcumin. In addition, high-speed countercurrent chromatography (HSCCC) purification is necessary to separate Curs for indicating the RMS. For HSCCC separation, a biphasic solvent system was used to obtain these fractions, which were then subjected to 1H quantitative NMR to determine their contents in each test solution. Using these solutions, the RMS of Curs are calculated from slopes ratios of calibration curves (three ranges from 0-100 µmol/L, r2 > 0.998). The averaged RMS of Curs were 8.92 (relative standard deviation (RSD), 1.17%), 8.97 (2.18%), and 9.61 (0.77%), respectively. Cur concentrations in turmeric products can be determined using RMS, peak area, and MR content added in these samples. This proposed method, which is based on chemical methylation and the SR-LC assay has been successfully applied for the simple and reliable estimation of Curs in turmeric products.


Assuntos
Diarileptanoides/química , Cromatografia Líquida de Alta Pressão/normas , Metilação , Estrutura Molecular , Padrões de Referência
4.
Chem Pharm Bull (Tokyo) ; 70(1): 32-36, 2022.
Artigo em Inglês | MEDLINE | ID: mdl-34980730

RESUMO

We have developed an HPLC-UV method for the determination of pyrroloquinoline quinone (PQQ), which utilizes a redox-based colorimetric reaction. In the proposed colorimetric reaction, the redox reaction between PQQ and dithiothreitol generates superoxide anion radicals that can convert 2-(4-iodophenyl)-3-(4-nitrophenyl)-5-phenyl-2H-tetrazolium chloride (INT) to formazan dye. After PQQ separation on an octadecyl silica column, it was mixed online with dithiothreitol and INT, and the formed formazan dye was monitored by absorbance at 490 nm. The detection limit (S/N = 3) of the proposed method was 7.6 nM (152 fmol/injection). The proposed method could selectively detect PQQ in food products without any clean-up procedures.


Assuntos
Colorimetria , Análise de Alimentos , Sucos de Frutas e Vegetais/análise , Cofator PQQ/análise , Cromatografia Líquida de Alta Pressão , Estrutura Molecular , Oxirredução , Raios Ultravioleta
5.
Chem Pharm Bull (Tokyo) ; 70(1): 37-42, 2022.
Artigo em Inglês | MEDLINE | ID: mdl-34980731

RESUMO

Eugenols (Eugs) such as eugenol (Eug), methyleugenol (MeEug), and linalool (Lin) in basil product are the main bioactive components of basil products and have a terminal double-bond. A sensitive HPLC-fluorescence method for Eugs derivatized with 4-(4,5-diphenyl-1H-imidazol-2-yl)iodobenzene (DIBI) was developed. Good separation of DIB-Eugs was achieved within 20 min on an Atlantis T3 column (50 × 2.1 mm i.d., 3 µm) with a mobile phase of methanol-water. The calibration curves obtained with Eug standards showed good linearities in the range of 0.1-50 µM (r ≥ 0.999). The limits of detection at a signal-to-noise ratio (S/N) = 3 for Eug, MeEug, and Lin were 1.0, 6.0, and 4.8 nM, respectively. The limits of quantitation (S/N = 10) of the Eugs were lower than 19.9 nM. The accuracies for the Eugs were within 96.8-104.6%. The intra- and inter-day precisions as relative standard deviations for the Eugs were less than 1.2 and 9.6% (n = 3). The recoveries of Eug, MeEug, and Lin were 99.0 ± 0.1, 98.0 ± 0.2, and 96.0 ± 0.4% (n = 3), respectively. The DIB-Eugs were confirmed to be stable for 2 h (>90%) at room temperature and 24 h (>95%) at 4 °C. These parameters of the proposed method were useful for the simultaneous determination of Eugs in basil products. Therefore, the developed method may be a powerful tool for the quality evaluation of dried commercially available basil products.


Assuntos
Eugenol/análise , Fluorescência , Ocimum basilicum/química , Cromatografia Líquida de Alta Pressão , Estrutura Molecular
6.
Chem Pharm Bull (Tokyo) ; 70(1): 66-73, 2022.
Artigo em Inglês | MEDLINE | ID: mdl-34980736

RESUMO

Despite the precise mechanisms for renal ischemia/reperfusion (I/R)-induced acute kidney injury (AKI) are poorly understood, nuclear factor erythroid 2 related factor 2 (Nrf2) and Toll-like receptor 4 (TLR4) pathways were considered as the important targets. Leonurine (LEO) is a special alkaloid extracted from Chinese motherwort (Leonurus japonicus Houtt), which has an anti-inflammatory effect and reduces oxidative stress. We conducted the study to explore the efficacy of LEO against I/R-induced AKI in rats and further investigated the underlying mechanisms. Ischemic renal injury was induced by temporary vascular clamping for 45 min. We have measured the levels of inflammation-related biomarkers and antioxidative stress markers. Next, Western blot analysis and Real-time PCR were performed to analyze whether the Nrf2 and TLR4/nuclear factor-kappaB (NF-κB) pathways were involved in this process. We found that LEO pretreatment remarkably decreased serum creatinine and blood urea nitrogen (BUN) in I/R rats and attenuated acute tubular damage. In addition, LEO markedly increased the expression of antioxidant proteins and decreased the levels of inflammatory factors. Further study revealed that LEO promoted Nrf2 into the nucleus, promoted the expression of heme oxygenase-1 (HO-1) and quinone oxidoreductase 1 (NQO-1), and suppressed the TLR4/NF-κB signal pathway in kidney tissues of ischemic AKI rats. The study reveals that LEO has a protective effect to prevent ischemic AKI through activation of Nrf2 nuclear translocation resisting oxidative stress injury and inhibition of the TLR4/NF-κB pathway mediated inflammatory gene expression.


Assuntos
Injúria Renal Aguda/tratamento farmacológico , Anti-Inflamatórios não Esteroides/farmacologia , Ácido Gálico/análogos & derivados , Leonurus/química , Fator 2 Relacionado a NF-E2/metabolismo , NF-kappa B/antagonistas & inibidores , Receptor 4 Toll-Like/antagonistas & inibidores , Injúria Renal Aguda/induzido quimicamente , Injúria Renal Aguda/patologia , Animais , Anti-Inflamatórios não Esteroides/química , Anti-Inflamatórios não Esteroides/isolamento & purificação , Núcleo Celular/efeitos dos fármacos , Núcleo Celular/metabolismo , Ácido Gálico/química , Ácido Gálico/isolamento & purificação , Ácido Gálico/farmacologia , Injeções Intraperitoneais , Masculino , Estrutura Molecular , NF-kappa B/metabolismo , Pentobarbital/administração & dosagem , Ratos , Ratos Sprague-Dawley , Receptor 4 Toll-Like/metabolismo
7.
Chem Pharm Bull (Tokyo) ; 70(1): 82-84, 2022.
Artigo em Inglês | MEDLINE | ID: mdl-34980738

RESUMO

Knoevenagel condensation, an olefin-forming reaction from active methyl/methylene-containing compounds and aldehydes, is a fundamental and useful synthetic method. Benzothiazoles are, however, out of the scope of Knoevenagel condensation. Here, we report that Knoevenagel condensation between aldehydes and 2-methyl-thiazolo[4,5-b]pyrazines (MeTPy), a fused ring structure comprising pyrazine and thiazole, proceeded smoothly, despite minor structural differences from benzothiazoles. This finding will be useful for short synthesis of MeTPy-containing functional molecules, such as a tau probe analog 1.


Assuntos
Aldeídos/química , Alcenos/síntese química , Pirazinas/química , Alcenos/química , Estrutura Molecular
8.
Chem Pharm Bull (Tokyo) ; 70(1): 85-88, 2022.
Artigo em Inglês | MEDLINE | ID: mdl-34980739

RESUMO

The electrophilic amination of nitrogen-based nucleophiles, including strong organic bases, was conducted in an Et2O solvent using O-(mesitylenesulfonyl)hydroxylamine. Aliphatic tert-amines and N,N,N'-(trialkyl)amidines rapidly formed precipitates of the corresponding aminated salts in high yields. The amination of the highly basic and sterically hindered N,N,N',N',N″-(pentaalkyl)guanidines was achieved under modified conditions, although the yields were moderate because of a competing side reaction caused by the acid-base equilibrium.


Assuntos
Amidinas/síntese química , Aminas/síntese química , Éteres/química , Guanidinas/síntese química , Amidinas/química , Aminação , Aminas/química , Guanidinas/química , Estrutura Molecular , Sais/síntese química , Sais/química , Solventes/química
9.
Phytochemistry ; 193: 113010, 2022 Jan.
Artigo em Inglês | MEDLINE | ID: mdl-34768184

RESUMO

The seeds of Herpetospermum pedunculosum (Ser.) C.B. Clarke, a well-known Tibetan medicine in China, are rich in kinds of bioactive lignans. In this phytochemical investigation on H. pedunculosum, sixteen undescribed lignans, named as herpedulins A - P together with 24 known ones were isolated from the ethyl acetate extract of its seeds. Their structures including the absolute configurations were determined by HR MS, 1D and 2D NMR experiments, and comparison of their experimental ECD spectra with calculated ones or literature data. High content screening experiments revealed that 9 compounds could promote the expression of farnesoid X receptor in guggulsterone-induced human normal liver cells L02 cells significantly. Further molecular docking results demonstrated that herpedulin E, J and K exhibited best docking scores (9.70, 9.28 and 10.31, respectively). Hydrogen bonding and hydrophobic interactions might contribute to the main interaction of active compounds with FXR.


Assuntos
Cucurbitaceae , Lignanas , Lignanas/farmacologia , Fígado , Simulação de Acoplamento Molecular , Estrutura Molecular , Sementes
10.
Phytochemistry ; 193: 112999, 2022 Jan.
Artigo em Inglês | MEDLINE | ID: mdl-34768186

RESUMO

Eight undescribed sesquiterpenoids, including two eudesmane glycosides dobinosides A and B, five eudesmane aglycones dobinins Q-U, and one germacrane dobinin P, were isolated from the 80% ethanol extract of roots of Dobinea delavayi. Their structures were elucidated by extensive spectroscopic data (1D and 2D NMR, HR-ESI-MS) and single-crystal X-ray diffraction analysis. Dobinoside A, dobinins Q and R, as well as six reported eudesmane sesquiterpenoids, were evaluated for their in vivo antimalarial activities against Plasmodium yoelii BY265RFP in mice. A summary of preliminary structure-activity relationship of eudesmane sesquiterpenoids for in vivo antimalarial activity was described.


Assuntos
Anacardiaceae , Antimaláricos , Sesquiterpenos de Eudesmano , Sesquiterpenos , Animais , Glicosídeos/farmacologia , Camundongos , Estrutura Molecular , Sesquiterpenos/farmacologia , Sesquiterpenos de Eudesmano/farmacologia
11.
Phytochemistry ; 193: 112987, 2022 Jan.
Artigo em Inglês | MEDLINE | ID: mdl-34768188

RESUMO

Picrasma quassioides, a member of the Simaroubaceae family, is the subject of research in numerous pharmacological and chemical studies. This plant mainly contains alkaloids, quassinoids and terpenoids. These molecules exhibit various pharmacological benefits, such as anti-inflammatory, anticancer, and anti-viral effects, on the cardiovascular system. Alkaloids make up the majority of these molecules. This review describes 127 alkaloid substances from P. quassioides. These alkaloids can be divided into the following classes: ß-carbolines, canthinones and alkaloid dimers. A compilation of their nuclear magnetic resonance spectroscopy data and possible biosynthetic pathways of these compounds and the pharmacological effects of P. quassioides are also included.


Assuntos
Alcaloides , Picrasma , Alcaloides/farmacologia , Vias Biossintéticas , Espectroscopia de Ressonância Magnética , Estrutura Molecular
12.
Phytochemistry ; 193: 113012, 2022 Jan.
Artigo em Inglês | MEDLINE | ID: mdl-34773753

RESUMO

Under OSMAC strategy, seven unreported multioxidized aromatic polyketides, penicanesins A‒G, were discovered from a soil-derived fungus Penicillium canescens along with seven known compounds. Their structures were assigned by extensive 1D and 2D NMR spectra in combination with HRESIMS and single crystal X-ray diffraction. Absolute stereochemistry of penicanesins A and D were elucidated by theoretical ECD calculation. (±)-Penicanesins A and B are two pairs of racemic aromatic polyketides with an unusual 6/6/6/6 heterotetracyclic ring core. In bioassay, (-)-penicanesin A shows potential cytotoxicity against human cancer cell lines HL-60 and SW480 with IC50 values at 13.8 ± 0.6 and 12.5 ± 0.9 µM, respectively, whereas the enantiomer (+)-penicanesin A is less active.


Assuntos
Penicillium , Policetídeos , Células HL-60 , Humanos , Estrutura Molecular , Policetídeos/farmacologia , Solo
13.
Spectrochim Acta A Mol Biomol Spectrosc ; 265: 120396, 2022 Jan 15.
Artigo em Inglês | MEDLINE | ID: mdl-34592685

RESUMO

Water activity is an important phenomenon not yet explained in terms of water molecular structure. This paper aims to find the relationship between the water activity and water molecular structure of the rice germ, based on its spectral pattern which can be measured using non-destructive technology. Aquaphotomics near-infrared spectroscopy was used to study rice germ stored at different levels of water activity and atmosphere. The findings show that state of the rice germ is governed by the water activity upon storage, which is defined by the structure of water within germ matrix. The structure of water can be described solely by the absorbance spectral pattern at the following absorbance bands: proton hydrates, hydration shells and water vapor (1364, 1375 and 1382 nm), trapped water (1392 nm), free water (1410 nm), hydration water (1425 nm), adsorbed water (1455 nm), non-bonded hydroxyl (1436 nm) and bound water (1520 nm).


Assuntos
Oryza , Espectroscopia de Luz Próxima ao Infravermelho , Biomarcadores , Estrutura Molecular , Preservação Biológica
14.
J Colloid Interface Sci ; 607(Pt 2): 1754-1761, 2022 Feb.
Artigo em Inglês | MEDLINE | ID: mdl-34598032

RESUMO

Saponins like ß-escin exhibit an unusually high surface activity paired with a remarkable surface rheology which makes them as biosurfactants highly interesting for applications in soft matter colloids and at interfaces. We have applied vibrational sum-frequency generation (SFG) to study ß-escin adsorption layers at the air-water interface as a function of electrolyte pH and compare the results from SFG spectroscopy to complementary experiments that have addressed the surface tension and the surface dilational rheology. SFG spectra of ß-escin modified air-water interfaces demonstrate that the SFG intensity of OH stretching vibrations from interfacial water molecules is a function of pH and dramatically increases when the pH is increased from acidic to basic conditions and reaches a plateau at a solution pH of > 6. These changes are attributable to the interfacial charging state and to the deprotonation of the carboxylic acid group of ß-escin. Thus, the change in OH intensity provides qualitative information on the degree of protonation of this group at the air-water interface. At pH < 4 the air-water interface is dominated by the charge neutral form of ß-escin, while at pH > 6 its carboxylic acid group is fully deprotonated and, consequently, the interface is highly charged. These observations are corroborated by the change in equilibrium surface tension which is qualitatively similar to the change in OH intensity as seen in the SFG spectra. Further, once the surface layer is charge neutral, the surface elasticity drastically increases. This can be attributed to a change in prevailing intermolecular interactions that change from dominating repulsive electrostatic interactions at high pH, to dominating attractive interactions, such as hydrophobic and dispersive interactions, as well as, hydrogen bonding at low pH values. In addition to the clear changes in OH intensity from interfacial H2O, the SFG spectra exhibit drastic changes in the CH bands from interfacial ß-escin which we relate to differences in the net molecular orientation. This orientation change is driven by tighter packing of ß-escin adsorption layers when the ß-escin moiety is in its charge neutral form (pH < 4).


Assuntos
Escina , Água , Concentração de Íons de Hidrogênio , Estrutura Molecular , Tensão Superficial
15.
J Colloid Interface Sci ; 607(Pt 2): 1805-1812, 2022 Feb.
Artigo em Inglês | MEDLINE | ID: mdl-34600344

RESUMO

Shear thickening fluids (STFs) have been the research focus for decades because of the prospect as a damping ingredient. However, their inherent liquid character confines their practical applications. In this work, inspired by the assembly engineering, novel gelatinous shear thickening fluids (GSTFs) are fabricated by integrating low molecular weight gelators (LMWGs) into STFs and investigated by rheological experiments. The results show that the apparent performances of GSTFs are determined by the LMWGs content. LMWGs inside GSTFs can assemble into three-dimensional network that can constraint the flowability of liquid molecular and their content dominate the density and strength of assembly network. At a moderate content, GSTFs exhibit desired properties with restricted quasi-static flowability and almost undamaged dynamic shear thickening character. While a higher content will disappear shear thickening and a lower content cannot gelate STFs. Besides, three different LMWGs are employed to gelate STFs and all they can gelate STFs in spite of the distinct minimum gelation concentration, indicating the universality for GSTFs preparation and the superiority of a reasonable molecular structure of LMWGs. Further, the temperature sweep experiments suggest that GSTFs can endure higher temperature without flowing due to its higher gel-sol transition temperature. Basing on these advanced mechanical properties, we believe that the GSTFs with more expected characters have significance for the study of non-Newtonian fluids and will broaden the special application field of STFs.


Assuntos
Reologia , Estrutura Molecular , Peso Molecular , Temperatura
16.
Food Chem ; 371: 131194, 2022 Mar 01.
Artigo em Inglês | MEDLINE | ID: mdl-34600364

RESUMO

Styrian pumpkin seed oil is a conditioned green-colored oil renowned for nutty smell and taste. Due to α-linolenic acid (ALA) contents below 1% of total fatty acids and the prospect of nutritional health claims based on its potential oxidation products, we investigated the fate of ALA and product oxylipins in the course of down-stream processing of seeds and in oils. Lipidomic analyses with Lipid Data Analyzer 2.8.1 revealed: Processing did not change (1) main fatty acid composition in the oils, (2) amounts of triacylglycerol species, (3) structures of triacylglycerol molecular species containing ALA. (4) Minor precursor ALA in fresh Styrian and normal pumpkins produced 6 product phytoprostanes in either cultivar, quantitatively more in the latter. (5) In oil samples 7 phytoprostanes and 2 phytofurans were detected. The latter two are specific for their presence in pumpkin seed oils, of note, quantitatively more in conditioned oils than in cold-pressed native oils.


Assuntos
Cucurbita , Ácidos Graxos , Lipidômica , Estrutura Molecular , Oxilipinas , Óleos Vegetais , Sementes , Triglicerídeos , Ácido alfa-Linoleico
17.
Methods Mol Biol ; 2390: 103-112, 2022.
Artigo em Inglês | MEDLINE | ID: mdl-34731465

RESUMO

The development of vaccines for the treatment of COVID-19 is paving the way for new hope. Despite this, the risk of the virus mutating into a vaccine-resistant variant still persists. As a result, the demand of efficacious drugs to treat COVID-19 is still pertinent. To this end, scientists continue to identify and repurpose marketed drugs for this new disease. Many of these drugs are currently undergoing clinical trials and, so far, only one has been officially approved by FDA. Drug repurposing is a much faster route to the clinic than standard drug development of novel molecules, nevertheless in a pandemic this process is still not fast enough to halt the spread of the virus. Artificial intelligence has already played a large part in hastening the drug discovery process, not only by facilitating the selection of potential drug candidates but also in monitoring the pandemic and enabling faster diagnosis of patients. In this chapter, we focus on the impact and challenges that artificial intelligence has demonstrated thus far with respect to drug repurposing of therapeutics for the treatment of COVID-19.


Assuntos
Antivirais/uso terapêutico , Inteligência Artificial , COVID-19/tratamento farmacológico , Descoberta de Drogas , Reposicionamento de Medicamentos , SARS-CoV-2/efeitos dos fármacos , Animais , Antivirais/efeitos adversos , COVID-19/diagnóstico , COVID-19/virologia , Interações Hospedeiro-Patógeno , Humanos , Aprendizado de Máquina , Estrutura Molecular , SARS-CoV-2/patogenicidade , Relação Estrutura-Atividade
18.
Methods Mol Biol ; 2390: 177-190, 2022.
Artigo em Inglês | MEDLINE | ID: mdl-34731469

RESUMO

We describe an approach to early stage drug discovery that explicitly engages with the complexities of human biology. The combined computational and experimental approach is formulated on a conceptual framework in which network biology is used to bridge between individual molecular entities and the cellular phenotype that emerges when those entities interact in a network. Multiple aspects of early stage discovery are addressed including the data-driven elucidation of biological processes implicated in disease, target identification and validation, phenotypic discovery of active molecules and their mechanism of action, and extraction of genetic target support from human population genetics data. Validation is described via summary of a number of discovery projects and details from a project aimed at COVID-19 disease.


Assuntos
Antivirais/uso terapêutico , COVID-19/tratamento farmacológico , Descoberta de Drogas , SARS-CoV-2/efeitos dos fármacos , Biologia de Sistemas , Animais , Antivirais/efeitos adversos , COVID-19/diagnóstico , COVID-19/virologia , Interações Hospedeiro-Patógeno , Humanos , Estrutura Molecular , Terapia de Alvo Molecular , SARS-CoV-2/patogenicidade , Relação Estrutura-Atividade
19.
Phytochemistry ; 195: 113049, 2022 Mar.
Artigo em Inglês | MEDLINE | ID: mdl-34902704

RESUMO

Agledulines A-K, eleven previously undescribed limonoids, including eight biogenic A/D-rings-seco limonoid analogs (agledulines A-H), one D-ring-seco limonoid (agleduline I) and two A-ring-seco limonoids with a rare Δ4,28 moiety (agledulines J-K), together with twelve reported limonoids, were isolated from the fruits of Aglaia edulis. Their structures were determined by NMR data, HRESIMS, X-ray diffraction, ECD spectra and the CD exciton chirality method. Observably, the absolute configurations of agleduline A, agleduline C and nymania 2 were unambiguously elucidated by single-crystal X-ray diffraction analyses. The biological evaluation showed that agleduline C exhibited significant cytotoxic activities with IC50 values of 10.05 µM, and 11α-acetoxygedunin showed notable anti-inflammatory activity (IC50: 4.70 µM). In addition, agleduline I and 11α-acetoxygedunin reversed the multidrug resistance with IC50 values of 5.05 and 1.49 µM (RI: 4.64 and 15.77) in the MCF-7/Dox cells.


Assuntos
Aglaia , Limoninas , Meliaceae , Frutas , Humanos , Limoninas/farmacologia , Estrutura Molecular
20.
Phytochemistry ; 195: 113057, 2022 Mar.
Artigo em Inglês | MEDLINE | ID: mdl-34942559

RESUMO

Three steroidal saponins detected by LC-MS were isolated from the leaves of Agave desmetiana hort. The three saponins were characterized as; Tigogenin 3 - [{O - ß - D - xylopyranosyl (1 â†’ 2) - α - L-rhamnopyranosyl (1 â†’ 3)}-ß-D- glucopyranoside), Tigogenin- 3 - ([O- α -L-rhamnopyranosyl (1 â†’ 3) - ß - D - glalactopyranosyl (1 â†’ 2)] - ß - D - glucopyranoside) and Tigogenin- 3 - ([{O - α - L - rhamnopyranosyl (1 â†’ 4)} - ß - D - galactopyranosyl (1 â†’ 3) - ß - D - xylopyranosyl (1 â†’ 2)] - ß - D - glucopyranoside). Identification and structure elucidation of the isolates were done via 1D and 2D NMR techniques, and chemical methods. Cytotoxic activity for the crude saponins and the three isolated compounds were evaluated against Hepg-2 and Mcf-7 cell lines. Compound 2 proved to be the most cytotoxic against tested cell lines with an IC50 2.97 and 2.49 µg/ml respectively.


Assuntos
Agave , Antineoplásicos , Saponinas , Cromatografia Líquida , Estrutura Molecular , Folhas de Planta , Saponinas/farmacologia
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