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1.
J Agric Food Chem ; 67(37): 10361-10372, 2019 Sep 18.
Artigo em Inglês | MEDLINE | ID: mdl-31487173

RESUMO

Alkyl di-/tri-/tetraoxyethyl ß-d-xylopyranosides as derivatives of alkyl xylosides are a class of non-ionic sugar-based surfactants. They were stereoselectively synthesized by the Helferich method. Their properties including hydrophilic-lipophilic balance number, water solubility, surface property, foam property, emulsifying property, and thermotropic liquid crystal property were mainly investigated. The results showed that their water solubility decreased with increasing the alkyl chain length and increasing the number of the oligooxyethyl fragment. The critical micelle concentration had a monotonous decreasing trend with increasing the alkyl chain length. Nonyl di-/tri-/tetraoxyethyl ß-d-xylopyranosides [-(OCH2CH2)m-, where m = 2, 3, and 4] exhibited the most excellent foaming ability and foam stability. In the n-octane/water system, dodecyl tetraoxyethyl ß-d-xylopyranosides and tetradecyl tetraoxyethyl ß-d-xylopyranosides had the strongest emulsion ability. In addition, some alkyl di-/tri-/tetraoxyethyl ß-d-xylopyranosides had thermotropic liquid crystal properties. Such sugar-based surfactants, alkyl di-/tri-/tetraoxyethyl ß-d-xylopyranosides, will be expected to develop for a variety of practical application.


Assuntos
Glicosídeos/química , Tensoativos/química , Glicosídeos/síntese química , Interações Hidrofóbicas e Hidrofílicas , Solubilidade , Propriedades de Superfície , Tensoativos/síntese química
2.
Chem Pharm Bull (Tokyo) ; 67(9): 935-939, 2019.
Artigo em Inglês | MEDLINE | ID: mdl-31474732

RESUMO

Chafuroside A and chafuroside B are flavone C-glycosides isolated from oolong tea leaves. They have a number of beneficial pharmacological activities related to antiinflammation at various concentrations. However, no crystallographic study of chafurosides has yet been reported. In the present study, the crystal structures of chafuroside A and chafuroside B were investigated using single-crystal X-ray diffraction. The asymmetric unit of the chafuroside A crystal consists of one chafuroside A and two water molecules, and that of chafuroside B contains one chafuroside B and one water molecule. The flavone moiety of chafuroside A is curved, i.e., the angle between the best-fit planes of the chromene and phenyl rings is 18.9°, whereas the chafuroside B flavone moiety is relatively flat. A comparison of the curvatures of the flavone moieties of various C-glycosides showed that the curvature of chafuroside A is significantly larger than those of the others. This structural feature might contribute to the differences between the strengths of the pharmacological activities of chafurosides A and B.


Assuntos
Flavonas/química , Glicosídeos/química , Compostos Heterocíclicos de 4 ou mais Anéis/química , Chá/química , Camellia sinensis/química , Camellia sinensis/metabolismo , Cristalografia por Raios X , Conformação Molecular , Folhas de Planta/química , Folhas de Planta/metabolismo
3.
J Agric Food Chem ; 67(40): 11089-11098, 2019 Oct 09.
Artigo em Inglês | MEDLINE | ID: mdl-31509411

RESUMO

Reactive oxygen species and subsequent oxidative stress are reported to play important roles in chronic metabolic diseases. Plant-derived polyphenols, especially food-derived phenolics, have attracted a lot of attention due to their potential usage against oxidative stress-related diseases. The leaf of Psidium guajava (known as guava) is regarded as a good resource of polyphenols and its products are commercially available in Japan as functional foods against multiple chronic metabolism disorders. In the course of finding novel polyphenols with antioxidative activities from guava leaf, 11 acylated phenolic glycosides (1-11), including 5 new oleuropeic acid-conjugated phenolic glycosides, named guajanosides A-E (1, 2, and 5-7), along with 17 known meroterpenoides (12-28), were isolated and identified. Their structures were determined by spectroscopic data analysis, chemical degradation, and acid hydrolysis. Compounds 1, 2, and 5-11 displayed potent reactive oxygen species-scavenging activity in lipopolysaccharide-stimulated RAW 264.7 macrophage cells. Western blot revealed that compound 6 markedly increased the expression levels of nuclear factor-erythroid 2-related factor 2 (Nrf2), NAD(P)H quinone dehydrogenase 1 (NQO1), and the glutamate-cysteine ligase catalytic subunit. The current study revealed the presence of oleuropeic acid-derived phenolic glycosides in guava leaf and highlighted the potential usage of this type of phenolics against oxidative stress-related metabolic diseases via activation of the Nrf2 signaling pathway.


Assuntos
Depuradores de Radicais Livres/farmacologia , Glicosídeos/farmacologia , Fenóis/farmacologia , Extratos Vegetais/farmacologia , Psidium/química , Espécies Reativas de Oxigênio/metabolismo , Animais , Depuradores de Radicais Livres/química , Glicosídeos/química , Macrófagos/efeitos dos fármacos , Macrófagos/metabolismo , Camundongos , Fator 2 Relacionado a NF-E2/genética , Fator 2 Relacionado a NF-E2/metabolismo , Estresse Oxidativo/efeitos dos fármacos , Fenóis/química , Extratos Vegetais/química , Folhas de Planta/química , Células RAW 264.7
4.
J Agric Food Chem ; 67(41): 11288-11306, 2019 Oct 16.
Artigo em Inglês | MEDLINE | ID: mdl-31557009

RESUMO

Delphinidin (Del) and its glycosides are water-soluble pigments, belonging to a subgroup of flavonoids. They are health-promoting candidates for pharmaceutical and nutraceutical uses, as indicated by exhibiting antioxidation, anti-inflammation, antimicroorganism, antidiabetes, antiobesity, cardiovascular protection, neuroprotection, and anticancer properties. Glycosylation modification of Del is associated with increased stability and reduced biological activity. Del and its glycosides can be the alternative inhibitors of CBRs, ERα/ß, EGFR, BCRP, and SGLT-1, and virtual docking indicates that the sugar moiety may not effectively interact with the active sites of the targets. Structure-based characteristics confer the multifunctional properties of Del and its glycosides. Because of their health-promoting effects, Del and its glycosides are promising and have been developed as potential pharmaceuticals. However, more investigation on the underlying mechanisms of Del and its glycosides in mediating cellular processes with high specificity are still needed. The research progression of Del and its glycosides over the last 10 years is comprehensively reviewed in this article.


Assuntos
Antocianinas/farmacologia , Glicosídeos/farmacologia , Animais , Antocianinas/química , Anti-Infecciosos/química , Anti-Infecciosos/farmacologia , Anti-Inflamatórios/química , Anti-Inflamatórios/farmacologia , Antioxidantes/química , Antioxidantes/farmacologia , Glicosídeos/química , Humanos , Estrutura Molecular
5.
J Agric Food Chem ; 67(37): 10330-10341, 2019 Sep 18.
Artigo em Inglês | MEDLINE | ID: mdl-31469960

RESUMO

Fomitopsis pinicola (Sw. Ex Fr.) Krast has been commonly used as a health food source and antitumor agent. To uncover bioactive key composition of F. pinicola, in our study, we investigated the chemical constituents of a methanol extract of F. pinicola and thirty-five lanostane-type tritetpenoids; 13 new compounds (1-13) and twenty-two known analogues (14-35) were isolated. Among them, compounds 1-9 were C30 lanostane triterpenoids and triterpene sugar esters, while compounds 10-13 were C31 triterpenoids and triterpene sugar esters. Their structures and absolute configurations were elucidated by extensive 1D, 2D NMR, MS, and IR spectra. Furthermore, cytotoxic activities of all isolates against five human tumor cell lines (HL-60, A549, SMMC-7721, MCF-7, and SW480) were evaluated. The results showed that compounds 12, 14, 17, 18, 22, and 23 displayed cytotoxic effects against five human tumor cell lines with IC50 values ranging from 3.92-28.51 µM. Meanwhile, compounds 9 and 35 exhibited selected inhibitory activities against HL-60, SMMC-7721, and MCF-7 with IC50 values in the range of 13.57-36.01 µM. Furthermore, the flow cytometry analysis revealed that compounds 17, 22, and 35 induced apoptosis in HL-60 cell lines. Their structure-activity relationships were preliminarily reported. These findings indicate the vital role of triterpenoids and their glycosides in explaining antitumor effects of F. pinicola and provide important evidence for further development and utilization of this fungus.


Assuntos
Coriolaceae/química , Extratos Vegetais/química , Extratos Vegetais/farmacologia , Triterpenos/química , Triterpenos/farmacologia , Verduras/química , Apoptose/efeitos dos fármacos , Linhagem Celular Tumoral , Sobrevivência Celular/efeitos dos fármacos , Glicosídeos/química , Glicosídeos/farmacologia , Humanos , Estrutura Molecular , Relação Estrutura-Atividade
6.
Life Sci ; 233: 116749, 2019 Sep 15.
Artigo em Inglês | MEDLINE | ID: mdl-31412264

RESUMO

AIMS: Functional dyspepsia (FD) is very common worldwide with a high prevalence of 10%-30%, and it becomes a heavy burden to patients because of its hard to be cured. In our previous study, phenylethanoid glycosides were found to exist in Houpo, a traditional Chinese medicine commonly used for the treatment of abdominal distention, pain and dyspepsia. In the present study, the effect of magnoloside A (MA), a main phenylethanoid glycoside in Houpo, on FD was firstly evaluated and its potential mechanism was concluded. MATERIALS AND METHODS: MA was orally administered consequently for 3 weeks, and its effect on a FD rat model established through transient neonatal gastric irritation and mature alternate-day fasting was tested. Levels of brain-gut peptides and inflammatory factors in blood or tissues were determined by ELISA methods. Meanwhile, the gut microbiota was analyzed by 16S rRNA gene sequencing and short chain fat acids were determined by GC/MS. KEY FINDINGS: MA exhibited anti-FD activities by fastening the delayed gut emptying rate of FD rat and increasing the levels of gastrin, motilin, and calcitonin gene related protein; and decreasing the levels of 5-hydroxytryptamine, nitric oxide synthase, and vasoactive intestinal peptide. On the other hand, MA can modulate the composition of gut microbiota, resulting in the variation of the short chain fat acids. SIGNIFICANCE: MA ameliorated FD rats by modulating of the secretion of related brain-gut peptides and altering the composition of intestinal microbiota.


Assuntos
Encéfalo/metabolismo , Dispepsia/tratamento farmacológico , Microbioma Gastrointestinal , Trato Gastrointestinal/metabolismo , Glicosídeos/administração & dosagem , Fragmentos de Peptídeos/metabolismo , Administração Oral , Animais , Animais Recém-Nascidos , Dispepsia/metabolismo , Dispepsia/microbiologia , Esvaziamento Gástrico/efeitos dos fármacos , Glicosídeos/química , Magnolia/química , Masculino , Álcool Feniletílico/química , Ratos , Ratos Sprague-Dawley
7.
Zhongguo Zhong Yao Za Zhi ; 44(13): 2806-2812, 2019 Jul.
Artigo em Chinês | MEDLINE | ID: mdl-31359694

RESUMO

A total of twelve compounds were isolated from the ethyl acetate of the water extract of honey-fried Eriobotrya japonica through column chromatography over silica gel,Sephadex LH-20,RP-18,and preparative HPLC. Their structures were established by MS,1 D NMR and 2 D NMR data as japonicanoside A( 1),nerolidol-3-O-α-L-rhamnopyranosyl-( 1→2)-ß-D-glucopyranoside( 2),nerolidol-3-O-α-L-rhamnopyranosyl-( l→4)-α-L-rhamnopyranosyl-( 1 → 2)-[α-L-( 4-trans-feruloyl)-rhamnopyranosyl-( 1 → 6) ]-ß-D-glucopyranoside( 3),( +)-catechin( 4),(-)-epicatechin( 5),kaempferol 3-O-α-L-rhamnopyranoside( 6),quercitrin( 7),quercetin-3-O-ß-D-galactopyranoside( 8),quercetin-3-O-ß-glucopyranoside( 9),vanillin( 10),protocatechuic aldehyde( 11),and maltol( 12). Among them,1 is a new phenolic glycoside.


Assuntos
Eriobotrya/química , Glicosídeos/isolamento & purificação , Mel , Cromatografia Líquida de Alta Pressão , Glicosídeos/química , Espectroscopia de Ressonância Magnética , Compostos Fitoquímicos/química , Compostos Fitoquímicos/isolamento & purificação
8.
J Agric Food Chem ; 67(28): 8020-8028, 2019 Jul 17.
Artigo em Inglês | MEDLINE | ID: mdl-31259548

RESUMO

In this study, a monoglucosyl rebaudioside A product was isolated from the mixture of glucosylated rebaudioside A obtained from the most reported and industrial used cyclodextrin glycosyl transferase, Toruzyme 3.0 L (CGTase, Toruzyme 3.0 L). The molecular structure of the monoglucosyl rebaudioside A was characterized using LC-MS/MS and methylation analysis combined with 1D and 2D NMR, indicating that it is 13-[(2-O-(3-α-O-D-glucopyranosyl)-ß-D-glucopyranosyl-3-O-ß-D-glucopyranosyl-ß-D-glucopyranosyl)oxy] ent-kaur-16-en-19-oic acid ß-D-glucopyranosyl ester (also known as RQ3, which naturally exists in Stevia extract as an isomer of rebaudioside D). This study may help to further understand the reaction mechanism of glucosylation of steviol glycoside assisted by Toruzyme 3.0 L in the aspect of molecule linkage pattern, and also benefit the application of the glucosylated rebaudiosides.


Assuntos
Diterpenos de Caurano/química , Glucosiltransferases/química , Glicosídeos/química , Biocatálise , Glicosilação , Isomerismo , Estrutura Molecular , Espectrometria de Massas em Tandem
9.
Chem Pharm Bull (Tokyo) ; 67(7): 675-689, 2019.
Artigo em Inglês | MEDLINE | ID: mdl-31257323

RESUMO

An Orobanchaceae plant Cistanche tubulosa (SCHENK) WIGHT (Kanka-nikujuyou in Japanese), which is one of the authorized plant resources as Cistanches Herba in both Japanese and Chinese Pharmacopoeias, is a perennial parasitic plant growing on roots of sand-fixing plants. The stems of C. tubulosa have traditionally been used for treatment of impotence, sterility, lumbago, and body weakness as well as a promoting agent of blood circulation. In recent years, Cistanches Herba has also been widely used as a health food supplement in Japan, China, and Southeast Asian countries. Here we review our recent studies on chemical constituents from the stems of C. tubulosa as well as their bioactivities such as vasorelaxtant, hepatoprotective, and glucose tolerance improving effects.


Assuntos
Produtos Biológicos/química , Cistanche/química , Animais , Aorta Torácica/efeitos dos fármacos , Aorta Torácica/metabolismo , Produtos Biológicos/isolamento & purificação , Produtos Biológicos/farmacologia , Cistanche/metabolismo , Glicosídeos/química , Glicosídeos/isolamento & purificação , Glicosídeos/farmacologia , Macrófagos/citologia , Macrófagos/efeitos dos fármacos , Macrófagos/metabolismo , Monoterpenos/química , Monoterpenos/isolamento & purificação , Monoterpenos/farmacologia , Caules de Planta/química , Caules de Planta/metabolismo , Substâncias Protetoras/química , Substâncias Protetoras/isolamento & purificação , Substâncias Protetoras/farmacologia , Vasodilatadores/química , Vasodilatadores/isolamento & purificação , Vasodilatadores/farmacologia
10.
Chem Biol Interact ; 309: 108707, 2019 Aug 25.
Artigo em Inglês | MEDLINE | ID: mdl-31194956

RESUMO

Alzheimer's disease (AD) is a slow but progressive neurodegenerative disease. One of the pathological hallmarks of AD is the progressive accumulation of ß-amyloid (Aß) in the form of senile plaques, and Aß insult to neuronal cells has been identified as one of the major causes of AD onset. In the present study, we investigated the anti-AD potential of four flavonoids, naringenin, didymin, prunin, and poncirin, by evaluating their ability to inhibit acetylcholinesterase (AChE), butyrylcholinesterase (BChE), and ß-site amyloid precursor protein cleaving enzyme 1 (BACE1). All four flavonoids displayed promising inhibitory activity against AChE, BChE, and BACE1. Structure-activity relationships suggested that glycosylation of naringenin at sugar moieties, and at different positions of the glycosidic linkage, might be closely associated with anti-AD potential. Kinetic and docking studies showed the lowest binding energy and highest affinity for the mixed, competitive, and non-competitive type inhibitors didymin, prunin, and poncirin. Hydrophobic interactions and the number of hydrogen bonds determined the strength of the protein-inhibitor interaction. We also examined the neuroprotective mechanisms by which flavonoids act against Aß25-35-induced toxicity in PC12 cells. Exposure of PC12 cells to 10 µM Aß25-35 for 24 h resulted in a significant decrease in cell viability. In addition, pretreatment of PC12 cells with different concentrations of flavonoids for 1 h significantly reversed the effects of Aß. Furthermore, treatment with the most active flavonoid, didymin, significantly reduced BACE1, APPsß, and C99 expression levels in a dose-dependent manner, without affecting amyloid precursor protein (APP) levels in the amyloidogenic pathway. Together, our results indicate that flavonoids, and in particular didymin, exhibit inhibitory activity in vitro, and may be useful in the development of therapeutic modalities for the treatment of AD.


Assuntos
Acetilcolinesterase/metabolismo , Secretases da Proteína Precursora do Amiloide/metabolismo , Peptídeos beta-Amiloides/metabolismo , Ácido Aspártico Endopeptidases/metabolismo , Butirilcolinesterase/metabolismo , Flavanonas/química , Glicosídeos/farmacologia , Agregados Proteicos/efeitos dos fármacos , Acetilcolinesterase/química , Doença de Alzheimer/metabolismo , Doença de Alzheimer/patologia , Secretases da Proteína Precursora do Amiloide/antagonistas & inibidores , Peptídeos beta-Amiloides/química , Peptídeos beta-Amiloides/farmacologia , Animais , Ácido Aspártico Endopeptidases/antagonistas & inibidores , Sítios de Ligação , Butirilcolinesterase/química , Domínio Catalítico , Sobrevivência Celular/efeitos dos fármacos , Glicosídeos/química , Cinética , Simulação de Acoplamento Molecular , Células PC12 , Fragmentos de Peptídeos/farmacologia , Substâncias Protetoras/química , Substâncias Protetoras/farmacologia , Ratos , Relação Estrutura-Atividade
11.
Phytochemistry ; 164: 206-214, 2019 Aug.
Artigo em Inglês | MEDLINE | ID: mdl-31177053

RESUMO

Eight undescribed cholestane glycosides named osaundersioside A-H, along with three previously known compounds named osaundersioside I-K were isolated from Ornithogalum saundersiae Baker bulbs (Asparagaceae). Their structures were elucidated by extensive spectroscopic analysis and chemical methods. All isolates were evaluated for their cytotoxic activity and inhibitory effects on lipopolysaccharide (LPS)-induced nitric oxide (NO) production. Osaundersioside C was thus determined to exhibit specific cytotoxicity towards MCF-7 cell line with an IC50 value of 0.20 µM, Osaundersioside H exhibited inhibitory effect on NO production in macrophages at the concentration of 10-5 M, with inhibition rate of 56.81%.


Assuntos
Anti-Inflamatórios não Esteroides/farmacologia , Antineoplásicos Fitogênicos/farmacologia , Asparagaceae/química , Colestanos/farmacologia , Glicosídeos/farmacologia , Animais , Anti-Inflamatórios não Esteroides/química , Anti-Inflamatórios não Esteroides/isolamento & purificação , Antineoplásicos Fitogênicos/química , Antineoplásicos Fitogênicos/isolamento & purificação , Proliferação de Células/efeitos dos fármacos , Colestanos/química , Colestanos/isolamento & purificação , Relação Dose-Resposta a Droga , Ensaios de Seleção de Medicamentos Antitumorais , Glicosídeos/química , Glicosídeos/isolamento & purificação , Humanos , Lipopolissacarídeos/antagonistas & inibidores , Lipopolissacarídeos/farmacologia , Células MCF-7 , Macrófagos/efeitos dos fármacos , Macrófagos/metabolismo , Camundongos , Estrutura Molecular , Óxido Nítrico/antagonistas & inibidores , Óxido Nítrico/biossíntese , Casca de Planta/química , Raízes de Plantas/química , Relação Estrutura-Atividade
12.
Food Chem ; 295: 214-223, 2019 Oct 15.
Artigo em Inglês | MEDLINE | ID: mdl-31174752

RESUMO

The profiles of phenolic compounds and antioxidant properties of dehulled foxtail millets were studied. Twenty-one phenolics were detected in the free fraction, including a series of nine hydroxycinnamic acid spermidines reported for the first time and three flavonoid C-glycosides of kaempferol and apigenin. Twenty-three phenolic acid derivatives were detected in the bound fraction with ferulic acid being the predominant phenolic acid, as well as four ferulic acid dimers (DFAs) reported for the first time in foxtail millet. Total phenolic contents (TPC) of free and bound fractions varied from 161.86 to 224.47 mg ferulic acid equivalent (FAE)/kg DW, 170.69 to 294.75 mg FAE/kg DW, respectively. Antioxidant activities, based on the DPPH, ABTS+ and ORAC assays, were determined for all extracts related to TPC. Dehulled foxtail millet contains a diverse profile of phenolic compounds potentially suitable for development of functional foods with unique antioxidant properties.


Assuntos
Antioxidantes/análise , Ácidos Cumáricos/análise , Flavonoides/análise , Fenóis/análise , Setaria (Planta)/química , Amidas/análise , Amidas/química , Antioxidantes/química , Ácidos Cumáricos/química , Análise de Alimentos , Glicosídeos/análise , Glicosídeos/química , Hidroxibenzoatos/análise , Quempferóis/química , Fenóis/química , Extratos Vegetais/análise , Extratos Vegetais/química
13.
Food Chem ; 297: 124970, 2019 Nov 01.
Artigo em Inglês | MEDLINE | ID: mdl-31253303

RESUMO

Choline chloride-based deep eutectic solvents (DESs) were used as green alternatives to conventional organic solvents for extracting valuable flavonoids from citrus peel waste. The effects of viscosity, pH, and polarity of DESs on the extraction efficiency were investigated. Results revealed linear dependence of extraction yield of citrus flavonoids on the polarity of the hydrogen bond donor (HBD). To simultaneously and effectively extract polymethoxylated flavonoids (PMFs) and glycosides of flavonoids (GoFs) with different polarities, five ternary DESs were designed and prepared by combining the effective HBD components. Among the tailor-made DESs studied, choline chloride-levulinic acid-N-methyl urea showed the highest extraction yield of total flavonoids. Under optimized extraction conditions, 18.75 mg/g PMFs and 47.07 mg/g GoFs were extracted from citrus peel with recoveries of 95.87% and 86.32%, respectively. This study presents a useful strategy based on tailor-made DESs to selectively extracted value-added flavonoids from waste peels in the citrus-processing industry.


Assuntos
Fracionamento Químico/métodos , Citrus/química , Flavonoides/isolamento & purificação , Solventes/química , Colina/química , Flavonoides/química , Glicosídeos/química , Glicosídeos/isolamento & purificação , Ligações de Hidrogênio , Concentração de Íons de Hidrogênio , Temperatura Ambiente , Viscosidade , Resíduos
14.
Microb Cell Fact ; 18(1): 97, 2019 May 31.
Artigo em Inglês | MEDLINE | ID: mdl-31151435

RESUMO

BACKGROUND: Transglycosylation represents one of the most promising approaches for obtaining novel glycosides, and plant phenols and polyphenols are emerging as one of the best targets for creating new molecules with enhanced capacities. These compounds can be found in diet and exhibit a wide range of bioactivities, such as antioxidant, antihypertensive, antitumor, neuroprotective and anti-inflammatory, and the eco-friendly synthesis of glycosides from these molecules can be a suitable alternative for increasing their health benefits. RESULTS: Transglycosylation experiments were carried out using different GH3 ß-glucosidases from the fungus Talaromyces amestolkiae. After a first screening with a wide variety of potential transglycosylation acceptors, mono-glucosylated derivatives of hydroxytyrosol, vanillin alcohol, 4-hydroxybenzyl alcohol, and hydroquinone were detected. The reaction products were analyzed by thin-layer chromatography, high-pressure liquid chromatography, and mass spectrometry. Hydroxytyrosol and vanillyl alcohol were selected as the best options for transglycosylation optimization, with a final conversion yield of 13.8 and 19% of hydroxytyrosol and vanillin glucosides, respectively. NMR analysis confirmed the structures of these compounds. The evaluation of the biological effect of these glucosides using models of breast cancer cells, showed an enhancement in the anti-proliferative capacity of the vanillin derivative, and an improved safety profile of both glucosides. CONCLUSIONS: GH3 ß-glucosidases from T. amestolkiae expressed in P. pastoris were able to transglycosylate a wide variety of acceptors. Between them, phenolic molecules like hydroxytyrosol, vanillin alcohol, 4-hydroxybenzyl alcohol, and hydroquinone were the most suitable for its interesting biological properties. The glycosides of hydroxytyrosol and vanillin were tested, and they improved the biological activities of the original aglycons on breast cancer cells.


Assuntos
Neoplasias da Mama , Celulases/metabolismo , Glicosídeos/farmacologia , Talaromyces/enzimologia , Benzaldeídos/metabolismo , Álcoois Benzílicos/metabolismo , Celulases/química , Celulases/isolamento & purificação , Glicosídeos/química , Glicosídeos/isolamento & purificação , Glicosilação , Humanos , Hidroquinonas/metabolismo , Células MCF-7 , Álcool Feniletílico/análogos & derivados , Álcool Feniletílico/metabolismo , Especificidade por Substrato
15.
Chem Pharm Bull (Tokyo) ; 67(6): 604-608, 2019.
Artigo em Inglês | MEDLINE | ID: mdl-31155567

RESUMO

Two new triterpene glycosides (1 and 2), together with nine known triterpene glycosides (3-11), were isolated from the seeds of Dolichos lablab (Leguminosae). The structures of the new compounds were determined by spectroscopic analysis, including two-dimensional NMR spectroscopy, and chromatographic analysis of the hydrolyzed products. The isolated compounds did not show cytotoxicity against HL-60 human leukemia cells and HepG2 human hepatoma cells at sample concentrations of 20 µM.


Assuntos
Dolichos/química , Glicosídeos/química , Triterpenos/química , Sobrevivência Celular/efeitos dos fármacos , Dolichos/metabolismo , Glicosídeos/isolamento & purificação , Glicosídeos/farmacologia , Células HL-60 , Células Hep G2 , Humanos , Espectroscopia de Ressonância Magnética , Conformação Molecular , Sementes/química , Sementes/metabolismo , Extração em Fase Sólida , Triterpenos/isolamento & purificação , Triterpenos/farmacologia
16.
Food Chem ; 297: 124921, 2019 Nov 01.
Artigo em Inglês | MEDLINE | ID: mdl-31253264

RESUMO

Plants conjugate monoterpenoids to sugars, rendering them non-volatile. Hydrolysis of these glycosidic precursors frees the volatile aroma compounds. Here, we profile intact monoterpenyl glycosides in six Vitis vinifera grape berry cultivars. Relative concentrations of twenty-six monoterpenyl glycosides, including nine new putatively identified compounds, were analyzed by UHPLC-QTOF MS/MS at three times during grape maturation (pre-véraison, véraison, and post-véraison). Total glycoside content reached a maximum in Muscat cultivars post-véraison but remained relatively constant in all other cultivars. Three types of monoterpenyl glycosides predominated in all samples: malonylated monoterpenol glucosides, monoterpenol hexose-pentoses, and monoterpendiol hexose-pentoses. The two Muscat cultivars were not differentiated at the earlier developmental stages but could be differentiated post-véraison. In contrast, similarities between Chardonnay and Pinot noir glycoside profiles developed post-véraison. Overall monoterpene glycoconjugation patterns may align with underlying genetic relationships among cultivars. By understanding monoterpene glycoconjugation in wine grapes, scientists and winemakers can better understand grape and wine aromas.


Assuntos
Monoterpenos/química , Vitis/química , Cromatografia Líquida de Alta Pressão , Análise por Conglomerados , Frutas/química , Frutas/metabolismo , Glicosídeos/química , Glicosídeos/metabolismo , Glicosilação , Monoterpenos/metabolismo , Análise de Componente Principal , Espectrometria de Massas em Tandem , Vitis/metabolismo
17.
Top Curr Chem (Cham) ; 377(4): 19, 2019 Jun 05.
Artigo em Inglês | MEDLINE | ID: mdl-31165274

RESUMO

This review is an effort to summarize recent developments in synthesis of O-glycosides and N-, C-glycosyl molecules with promising antidiabetic potential. Articles published after 2000 are included. First, the O-glycosides used in the treatment of diabetes are presented, followed by the N-glycosides and finally the C-glycosides constituting the largest group of antidiabetic drugs are described. Within each group of glycosides, we presented how the structure of compounds representing potential drugs changes and when discussing chemical compounds of a similar structure, achievements are presented in the chronological order. C-Glycosyl compounds mimicking O-glycosides structure, exhibit the best features in terms of pharmacodynamics and pharmacokinetics. Therefore, the largest part of the article is concerned with the description of the synthesis and biological studies of various C-glycosides. Also N-glycosides such as N-(ß-D-glucopyranosyl)-amides, N-(ß-D-glucopyranosyl)-ureas, and 1,2,3-triazolyl derivatives belong to the most potent classes of antidiabetic agents. In order to indicate which of the compounds presented in the given sections have the best inhibitory properties, a list of the best inhibitors is presented at the end of each section. In summary, the best inhibitors were selected from each of the summarizing figures and the results of the ranking were placed. In this way, the reader can learn about the structure of the compounds having the best antidiabetic activity. The compounds, whose synthesis was described in the article but did not appear on the figures presenting the structures of the most active inhibitors, did not show proper activity as inhibitors. Thus, the article also presents studies that have not yielded the desired results and show directions of research that should not be followed. In order to show the directions of the latest research, articles from 2018 to 2019 are described in a separate Sect. 5. In Sect. 6, biological mechanisms of action of the glycosides and patents of marketed drugs are described.


Assuntos
Diabetes Mellitus/tratamento farmacológico , Descoberta de Drogas/métodos , Glicosídeos/química , Glicosídeos/farmacologia , Hipoglicemiantes/química , Hipoglicemiantes/farmacologia , Animais , Diabetes Mellitus/enzimologia , Diabetes Mellitus/metabolismo , Inibidores Enzimáticos/química , Inibidores Enzimáticos/farmacocinética , Inibidores Enzimáticos/farmacologia , Inibidores Enzimáticos/uso terapêutico , Glicogênio Fosforilase/antagonistas & inibidores , Glicogênio Fosforilase/metabolismo , Glicosídeos/farmacocinética , Glicosídeos/uso terapêutico , Humanos , Hipoglicemiantes/farmacocinética , Hipoglicemiantes/uso terapêutico , Proteína Tirosina Fosfatase não Receptora Tipo 1/antagonistas & inibidores , Proteína Tirosina Fosfatase não Receptora Tipo 1/metabolismo , Inibidores do Transportador 2 de Sódio-Glicose/química , Inibidores do Transportador 2 de Sódio-Glicose/farmacocinética , Inibidores do Transportador 2 de Sódio-Glicose/farmacologia , Inibidores do Transportador 2 de Sódio-Glicose/uso terapêutico , Relação Estrutura-Atividade
18.
Phytochemistry ; 164: 172-183, 2019 Aug.
Artigo em Inglês | MEDLINE | ID: mdl-31158602

RESUMO

Screening assays showed that total glycoside-rich fraction (TG) of rhizomes of Polygonatum sibiricum unveiled remarkable anti-proliferative activities against three cancer cell lines (A549, HepG2, and Caco2). Activity-guided isolation of TG afforded seven undescribed steroidal glycosides (polygonosides 1-7), along with 24 known glycosides. Their structures were established by 1D and 2D NMR spectroscopic analyses, high-resolution mass spectrometry, and chemical evidence. The isolated steroidal glycosides were tested for their antiproliferative activities against A549, HepG2, and Caco2 cells. Compounds 8, 10, 11, and 16 possessed stronger anticancer activities against A549 cells than the positive control Bay (25.8 µM), with IC50 values ranging from 5.8 to 24.2 µM. Compound 10 reduced the expression of Blc-2 and pro-caspase3 and increased the production of Bax as determined by western blotting. Molecular docking experiment suggested that 10 bound stably to the BH3-binding groove of the Bcl-2 protein by hydrogen bond interactions. These compounds could be candidates for anticancer agents with cytotoxic activity.


Assuntos
Antineoplásicos Fitogênicos/farmacologia , Glicosídeos/farmacologia , Polygonatum/química , Rizoma/química , Esteroides/farmacologia , Antineoplásicos Fitogênicos/química , Antineoplásicos Fitogênicos/isolamento & purificação , Apoptose/efeitos dos fármacos , Linhagem Celular Tumoral , Proliferação de Células/efeitos dos fármacos , Sobrevivência Celular/efeitos dos fármacos , Relação Dose-Resposta a Droga , Ensaios de Seleção de Medicamentos Antitumorais , Glicosídeos/química , Glicosídeos/isolamento & purificação , Humanos , Conformação Molecular , Simulação de Acoplamento Molecular , Esteroides/química , Esteroides/isolamento & purificação , Relação Estrutura-Atividade
19.
J Food Sci ; 84(7): 1986-1991, 2019 Jul.
Artigo em Inglês | MEDLINE | ID: mdl-31192461

RESUMO

Cassava leaves are a valuable source of protein but the cyanogenic potential limits their use as food and feed. Four different treatments were investigated to detoxify cassava leaves. Thermal (55 °C for 6 hr), sodium bicarbonate (0.4% NaHCO3 , 55 °C for 6 hr), enzymatic (0.32% Multifect® GC Extra, 4 hr), and ultrasonic treatments (500 W, 35 kHz, 55 °C, 0.25 hr) reduced the total cyanide (µg HCN equivalents per g fresh leaf or ppm) content by 90%, 93%, 82%, and 84% while the cyanide content reduction in the respective controls was 85%, 90%, 79%, and 84%, respectively. The sodium bicarbonate treatment was found to be the most effective treatment. Therefore, it was further optimized by varying time and temperature. A significant effect on the cyanide content was observed by changing the incubation time while no significant effect of temperature was noticed. Nevertheless, extended incubation time during sodium bicarbonate treatment reduced ascorbic acid content by 7% and 39% when leaves were incubated with sodium bicarbonate for 0.5 hr and 48 hr, respectively. PRACTICAL APPLICATION: Cyanogenic glucosides are the major toxic compound in cassava leaves, which limits their use as food and feed. The methods proposed in this study can be used to detoxify cassava leaves, which are generally considered as an inferior by-product. Hence, detoxified cassava leaves may contribute to fulfil world protein demand in an eco-sustainable way.


Assuntos
Cianetos/química , Manipulação de Alimentos/métodos , Glicosídeos/química , Manihot/química , Folhas de Planta/química , Biocatálise , Cianetos/toxicidade , Enzimas/química , Glicosídeos/toxicidade , Temperatura Alta , Manihot/toxicidade , Folhas de Planta/toxicidade , Bicarbonato de Sódio/química , Ultrassom
20.
Chem Pharm Bull (Tokyo) ; 67(6): 534-539, 2019.
Artigo em Inglês | MEDLINE | ID: mdl-31155558

RESUMO

One triterpene and five triterpene glycosides, including four new compounds, have been identified in the underground parts of Glycyrrhiza bucharica, which was shown to be closely related to Glycyrrhizin-producing Glycyrrhiza species, G. uralensis, G. glabra and G. inflata, based on their chloroplast rbcL sequences. Two known compounds were identified squasapogenol and macedonoside C. The structures of four new compounds, bucharosides A, B, C, and D, were determined to be 3-O-α-L-rhamnopyranosyl-(1→2)-ß-D-glucuronopyranosyl-(1→2)-ß-D-glucuronopyranosyl-22-O-α-L-rhamnopyranosyl squasapogenol, 3-O-α-L-rhamnopyranosyl-(1→2)-ß-D-glucuronopyranosyl-(1→2)-ß-D-glucuronopyranosyl-macedonic acid, 3-O-α-L-rhamnopyranosyl-(1→2)-ß-D-glucuronopyranosyl-(1→2)-ß-D-glucuronopyranosyl-squasapogenol, and 22-O-α-L-rhamnopyranosyl squasapogenol, respectively. Contents of these triterpene glycosides were less than 0.5% of dry weight, and no main saponin, like glycyrrhizin or macedonoside C found in other Glycyrrhiza species, was found in the underground parts of G. bucharica.


Assuntos
Glycyrrhiza/química , Extratos Vegetais/química , Glicosídeos/química , Glicosídeos/isolamento & purificação , Glycyrrhiza/metabolismo , Espectroscopia de Ressonância Magnética , Conformação Molecular , Raízes de Plantas/química , Raízes de Plantas/metabolismo , Tadjiquistão , Terpenos/química , Terpenos/isolamento & purificação , Triterpenos/química , Triterpenos/isolamento & purificação
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