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1.
Molecules ; 26(4)2021 Feb 18.
Artigo em Inglês | MEDLINE | ID: mdl-33670764

RESUMO

Phytochemical investigation of leaves and stembark of Artocarpus lacucha collected in Thailand resulted in three yet undescribed isomeric flavan-3-ol derivatives (1-3), the four known compounds gambircatechol (4), (+)-catechin (5), (+)-afzelechin (6) and the stilbene oxyresveratrol (7). Compounds 1 to 3 feature 6/6/5/6/5/6 core structures. All structures were deduced by NMR and MS, while density functional theory (DFT) calculations on B3LYP theory level were performed of compounds 1 to 3 to support the stereochemistry in positions 2 and 3 in the C-ring. Possible biosynthetic pathways leading to 4 are discussed. The DPPH assay revealed high radical scavenging activities for 1 (EC50 = 9.4 ± 1.0 µmol mL-1), 2 (12.2 ± 1.1), 3 (10.0 ± 1.5) and 4 (19.0 ± 2.6), remarkably lower than ascorbic acid (EC50 = 34.9) and α-tocopherol (EC50 = 48.6). A cytotoxicity assay revealed moderate but consistent antiproliferative properties of 1 in CH1/PA-1 (ovarian teratocarcinoma) and SW480 (colon carcinoma) cells, with IC50 values of 25 ± 6 and 34 ± 4 µM, respectively, whereas effects in A549 (non-small cell lung cancer) cells were rather negligible. The performed DCFH-DA assay of 1 in the former cell lines confirmed potent antioxidative effects even in the cellular environment.


Assuntos
Artocarpus/química , Flavonoides/farmacologia , Depuradores de Radicais Livres/farmacologia , Antioxidantes/farmacologia , Morte Celular/efeitos dos fármacos , Linhagem Celular Tumoral , Proliferação de Células/efeitos dos fármacos , Simulação por Computador , Flavonoides/química , Humanos , Espectroscopia de Ressonância Magnética , Conformação Molecular , Oxirredução , Estereoisomerismo
2.
Food Chem ; 339: 127896, 2021 Mar 01.
Artigo em Inglês | MEDLINE | ID: mdl-32866696

RESUMO

Jackfruits are nutritionally rich fruit crop indigenous to the humid tropics, known by their place of origin. In the present study, using multielemental profiling of fruit samples, we demonstrated the discrimination of different jack fruit germplasm based on their geographical origin in India. The concentration of 24 elements in soil and fruit were determined by inductively coupled plasma mass spectrometry (ICP-MS). ANOVA revealed the significant difference of these 24 elements amongst the geographical locations both in soils and fruits. The correlation between soil and fruit ionome indicated the major influence of germplasm and other locational factors on the acquisition and accumulation of fruit multi elemental characteristics with minimal contribution of soil elements. Among the multivariate analysis tools, linear discriminant analysis (LDA) of fruit multi elemental fingerprint was found to be an efficient tool for discrimination of geographical origin of Indian jackfruits.


Assuntos
Artocarpus/química , Solo/química , Artocarpus/metabolismo , Análise Discriminante , Frutas/química , Frutas/metabolismo , Índia , Íons/análise , Espectrometria de Massas/métodos , Metais/química , Análise de Componente Principal
3.
Food Chem ; 340: 127876, 2021 Mar 15.
Artigo em Inglês | MEDLINE | ID: mdl-32871354

RESUMO

Jackfruit is a sweet tropical fruit with very pleasant aroma, and the ripe seeds are edible. In this study, jackfruit seed proteins were isolated and subjected to trypsin digestion. The resultant protein hydrolysate was then subjected to antioxidant assay-guided purification, using centrifugal filtration, C18 reverse-phase and strong cation exchange (SCX) fractionations. The purified SCX fraction was further analyzed by de novo peptide sequencing, and two peptide sequences were identified and synthesized. Peptide JFS-2 (VGPWQK) was detected with antioxidant potential, with EC50 value comparable to that of commercial GSH antioxidant peptide. Additionally, the identified peptides were tested with protein protection potential, in an albumin protein denaturation inhibitory assay. Concurrently, we also investigated the pH, temperature, and gastrointestinal-digestion stability profiles for the identified peptide. With further research efforts, the identified peptides could potentially be developed into preservative agent for protein-rich food systems or as health-promoting diet supplements.


Assuntos
Antioxidantes/análise , Artocarpus/química , Peptídeos/análise , Peptídeos/química , Hidrolisados de Proteína/química , Sementes/química , Antioxidantes/química , Cromatografia por Troca Iônica , Digestão , Conservantes de Alimentos , Concentração de Íons de Hidrogênio , Peptídeos/metabolismo , Temperatura , Tripsina
4.
Food Chem ; 336: 127716, 2021 Jan 30.
Artigo em Inglês | MEDLINE | ID: mdl-32768910

RESUMO

Jackfruit seed starch (JFSS) was modified by an improved extrusion cooking technology (IECT), and the supramolecular structure, molecular weight, debranched chain length distributions, relative crystallinity (Rc), and amylose content, were studied. During IECT, the α-1.4-glycosidic bond in amylopectin was broken, which led to decreased radius of gyration (Rg), number-average molar mass (Mn), weight-average molar mass (Mw), long chains and Rc. The medium and short chains and PI (Mw/Mn) increased, while the amylose content hardly changed. The crystalline structure of JFSS was converted from A-type to V-type. Increasing the temperature and screw speed during the treatment significantly increased the medium and short chains and Rg, while it decreased the long chains, amylose, Mn, Mw, PI, and Rc. However, the opposite effect was observed when increasing the moisture content. The in vitro digestibility of JFSS was significantly improved after IECT, due to destruction of starch supramolecular structure according to principal component analysis.


Assuntos
Artocarpus/química , Sementes/química , Amido/química , Amilopectina/química , Amilose/análise , Amilose/química , Culinária/métodos , Digestão , Peso Molecular , Análise de Componente Principal , Temperatura
5.
PLoS One ; 15(7): e0236300, 2020.
Artigo em Inglês | MEDLINE | ID: mdl-32702056

RESUMO

Breadfruit is a traditional staple crop from Pacific islands with the potential to improve worldwide food security and mitigate diabetes. Flour produced from breadfruit is a gluten-free, low glycemic index, nutrient dense and complete protein option for modern foods but basic scientific knowledge of health impacts of a breadfruit-based diet in animals and humans was lacking. We designed a series of studies to provide basic and fundamental data on impacts of a breadfruit-based diet through an in vitro and in vivo model. Cooked breadfruit flour was digested through a multi-stage enzyme digestion model to estimate protein digestibility in comparison to wheat flour. Breadfruit protein was found to be easier to digest than wheat protein in the enzyme digestion model. The flour digestions were applied to Caco-2 cells to test the cytotoxicity and to measure the immunogenicity through cytokine expression. No significant differences were observed for immune factors and cytokines (IL-4, IL-10, IL-8, TNF-α, IFN-γ) on Caco-2 cells between the breadfruit and wheat groups. A breadfruit-based rodent chow was formulated by substitution of all of the wheat in the standard formulation with breadfruit. The diets were isocaloric, nutrient equivalent and used to feed male and female C57BL/6 mice for 21 days. No sign of malnutrition, discomfort, illness or death was observed among the mice because of the diet. The histology and the cytokine expression of the mice ileum from both groups were analyzed and showed similar results. The expression of major bacteria was measured in the colon and showed similar results. Mice fed the breadfruit diet had a significantly higher growth rate and body weight than standard diet fed mice. No negative health outcomes were observed in studies with in vitro or in vivo models and breadfruit flour is a healthy alternative to other starches for modern foods.


Assuntos
Artocarpus/química , Farinha , Abastecimento de Alimentos , Alimentos , Animais , Composição Corporal/efeitos dos fármacos , Células CACO-2 , Morte Celular/efeitos dos fármacos , Sobrevivência Celular/efeitos dos fármacos , Citocinas/metabolismo , Dieta , Fezes/química , Humanos , Íleo/efeitos dos fármacos , Íleo/patologia , Interleucina-1beta/farmacologia , Lipopolissacarídeos/farmacologia , Camundongos Endogâmicos C57BL , Minerais/análise , Óxido Nítrico Sintase Tipo II/metabolismo
6.
Food Chem ; 330: 127211, 2020 Nov 15.
Artigo em Inglês | MEDLINE | ID: mdl-32540527

RESUMO

With the current agro-food industry demands for more environmentally-friendly production, the use of natural antifungal compounds extracted by emerging technologies led to a sustainable alternative to control microorganisms. Therefore, the present work aimed to: (i) determine antifungal activity against Colletotrichum gloeosporioides and Penicillium italicum of jackfruit leaf extracts obtained by different methods, and (ii) identify compounds by HPLC-DAD-ESI-MS. Microwave (MAE), high-hydrostatic pressure (HHP) and ultrasound (UAE) assisted extractions were tested, followed by fractionation with different polarity solvents. The concentration of total soluble phenols (TSP), tannins (TT) and flavonoids (TF) were determined. Differences not only in the amounts of extracted phytochemicals were found but in the antifungal properties (MAE against P. italicum and HHP against C. gloeosporioides at 5 mg/ml) as well as in the chemical composition determined by HPLC-MS. These results suggest the possible application of jackfruit leaf extracts as a suitable postharvest antifungal treatment.


Assuntos
Antifúngicos/química , Artocarpus/química , Compostos Fitoquímicos/química , Extratos Vegetais/química , Antifúngicos/farmacologia , Colletotrichum/efeitos dos fármacos , Flavonoides/química , Penicillium/efeitos dos fármacos , Fenóis/química , Compostos Fitoquímicos/farmacologia , Extratos Vegetais/farmacologia , Folhas de Planta/química , Taninos/química
7.
Sci Rep ; 10(1): 10198, 2020 06 23.
Artigo em Inglês | MEDLINE | ID: mdl-32576906

RESUMO

A trend of present encapsulation research indicates an increased interest in the search for natural encapsulants for bioactive phytochemicals. The present study in pursuit of the same studies the use of jackfruit seed starch (JSS), an underutilized natural polysaccharide in conjugation with soy protein isolate (SPI) as an encapsulating material and NBRE-15 as an emulsifier. Three independent variables viz., total soluble solids (TSS, 20, 25 and 30° Brix), SPI: JSS (1:1, 1:3 and 1:5) and NBRE-15 (0.1, 0.2 and 0.3%) were optimized for achieving the most efficient encapsulation of anthocyanin using a three level, three parameter, Box-Behnken design (BBD) of the Design of Experiments (DOE). The responses considered for the optimization were monomeric anthocyanin content, antioxidant activity and encapsulation efficiency. A combination of 27.0% TSS, 1:5 SPI: JSS ratio and 0.3% NBRE-15 was found to be optimum for the encapsulation of anthocyanin with the desirability of 92.6%. Microcapsules obtained using the optimized combination of independent variables was found to contain 3215.59 mg/100 g monomeric anthocyanin. The antioxidant activity and encapsulation efficiency of the encapsulated material obtained using optimized combinations of independent variable were found to be 365.26 µmol Trolox/g and 89.71%, respectively. The microcapsules were also additionally analyzed for the particle size distribution and morphological characterization. Particle size analysis indicated that the microcapsules obtained had a mean particle size of 60.97 µm. Scanning electron microscopy for morphological characterization indicated that the microcapsules so obtained were oval to round in shape and had a smooth surface. Storage studies to estimate the half-life of anthocyanin in the microcapsule at room temperature (37 °C) clearly indicated greater stability i.e. 63 days when stored under amber-colored vial compared to only 35 days when stored under clear transparent vial.


Assuntos
Antocianinas/química , Artocarpus/química , Emulsificantes/química , Pós/química , Sementes/química , Proteínas de Soja/química , Amido/química , Antioxidantes/química , Cápsulas/química , Tamanho da Partícula , Polissacarídeos/química , Temperatura
8.
J Agric Food Chem ; 68(7): 2024-2030, 2020 Feb 19.
Artigo em Inglês | MEDLINE | ID: mdl-32037814

RESUMO

Artocarpus heterophyllus (jack tree) is an evergreen fruit tree belonging to the genus Artocarpus (Moraceae), which is widely distributed in subtropical and tropical regions of Asia. Its fruits (jackfruit), well-known as the world's largest tree-borne fruit, are being consumed in our daily diets as a very popular tropical fruit throughout the world and have been confirmed to hold various health benefits. In this study, five new prenylated chromones, artocarheterones A-E (1-5), as well as seven known prenylated chromones (6-12) were purified and isolated from the ripe fruits of A. heterophyllus (jackfruit). Their chemical structures were determined through comprehensive spectroscopic methods. This is the first report on prenylated chromones isolated from A. heterophyllus. The anti-HIV-1 effects of all isolated chromones were assessed in vitro. As a result, prenylated chromones (1-12) showed remarkable anti-HIV-1 effects with EC50 values ranging from 0.09 to 9.72 µM. These research results indicate that the isolation and characterization of these prenylated chromones with remarkable anti-HIV-1 activities from the ripe fruits of A. heterophyllus could be significant to the discovery and development of new anti-HIV-1 drugs.


Assuntos
Fármacos Anti-HIV/química , Fármacos Anti-HIV/farmacologia , Artocarpus/química , Cromonas/química , Cromonas/farmacologia , Extratos Vegetais/química , Extratos Vegetais/farmacologia , Frutas/química , HIV-1/efeitos dos fármacos , HIV-1/fisiologia , Estrutura Molecular , Prenilação
9.
Meat Sci ; 163: 108082, 2020 May.
Artigo em Inglês | MEDLINE | ID: mdl-32050113

RESUMO

This study evaluated structural and technological properties of beef emulsion modeling systems prepared with tropical flours. Treatments consisted of a control (0% flour inclusion) and three inclusion levels (1%, 2% and 4%) of two breadfruit flours and a banana flour. Flour type affected starch content of cooked beef emulsions, with greater starch content for emulsions prepared with banana flour compared with breadfruit flour, yet flour type did not affect cooking loss. Hardness and chewiness of cooked beef emulsion prepared with breadfruit flour decreased as inclusion level increased from 0% to 4%, while hardness was not affected by inclusion level of banana flour. Redness values of cooked beef emulsions increased as flour inclusion level increased, but were not affected by flour type. Evaluation of the beef emulsion microstructure and storage modulus revealed that the starch granules of banana flour behaved remarkably different than breadfruit flour. Overall, there were positive structural and technological attributes when tropical flours were included in beef emulsions.


Assuntos
Artocarpus/química , Emulsões , Manipulação de Alimentos/métodos , Musa/química , Animais , Bovinos , Produtos da Carne/análise , Proteínas de Soja , Amido/química
10.
Curr Pharm Biotechnol ; 21(10): 980-989, 2020.
Artigo em Inglês | MEDLINE | ID: mdl-31914911

RESUMO

AIMS: To evaluate the antibacterial activity of Artocarpus hirsutus mediated seed extract for nanoparticle synthesis. BACKGROUND: Gastrointestinal bacteria are known for causing deadly infections in humans. They also possess multi-drug resistance and interfere with clinical treatments. Applied nanotechnology has been known to combat such infectious agents with little interference from their special attributes. Here we synthesize silver nanoparticles from Artocarpus hirsutus seed extract against two gastro-intestinal bacterial species: Enterobacter aerogenes and Listeria monocytogenes. OBJECTIVE: To collect, dry, and process seeds of Artocarpus hirsutus for nanoparticle synthesis. To evaluate the morphological interaction of silver nanoparticles with bacteria. METHODS: Artocarpus hirsutus seeds were collected and processed and further silver nanoparticles were synthesized by the co-precipitation method. The synthesized nanoparticles were characterized using XRD, UV, FTIR, and SEM. These nanoparticles were employed to study the antibacterial activity of nanoparticles against Enterobacter aerogenes and Listeria monocytogenes using well diffusion method. Further, morphological interaction of silver nanoparticles on bacteria was studied using SEM. RESULTS: Silver nanoparticles were synthesized using Artocarpus hirsutus seed extract and characterization studies confirmed that silver nanoparticles were spherical in shape with 25-40 nm size. Antibacterial study exhibited better activity against Enterobacter aerogenes with a maximum zone of inhibition than on Listeria monocytogenes. SEM micrographs indicated that Enterobacter aerogenes bacteria were more susceptible to silver nanoparticles due to the absence of cell wall. Also, the size and charge of silver nanoparticles enable easy penetration of the bacterial cell wall. CONCLUSION: In this study, silver nanoparticles were synthesized using the seed extract of Artocarpus hirsutus for the first time exploiting the fact that Moraceae species have high phytonutrient content which aided in nanoparticle synthesis. This nanoparticle can be employed for large scale synthesis which when coupled with the pharmaceutical industry can be used to overcome the problems associated with conventional antibiotics to treat gastrointestinal bacteria.


Assuntos
Antibacterianos/farmacologia , Artocarpus/química , Nanopartículas Metálicas/química , Extratos Vegetais/química , Prata/farmacologia , Antibacterianos/química , Enterobacter aerogenes/efeitos dos fármacos , Humanos , Listeria monocytogenes/efeitos dos fármacos , Nanotecnologia , Sementes/química , Prata/química , Prata/isolamento & purificação
11.
J Sci Food Agric ; 100(5): 1962-1970, 2020 Mar 30.
Artigo em Inglês | MEDLINE | ID: mdl-31846074

RESUMO

BACKGROUND: This study evaluated the impact of cooking on the profile of bioactive compounds in unripe breadfruit. To this end, the accessibility of bioactive compounds by various solvents was assessed through total phenolic content and antioxidant capacity analyses. The most efficient solvent was applied to extract the metabolites, which were evaluated by ultra-performance liquid chromatography coupled with high-resolution quadrupole time-of-flight mass spectrometry in MSE mode. RESULTS: Cooked and raw breadfruit presented total phenolic content and antioxidant capacities in almost all extracts, and pure water proved to be the best extractor. Globally, 146 bioactive compounds have been identified for both raw and cooked fruits' aqueous extracts. Most of these compounds were stable to the heat treatment applied (121 °C/10 min). However, results revealed that 22 metabolites contributed to significantly distinguishing the raw from the cooked samples. Among those, 15 compounds, such as pyrogallol, 1-acetoxypinoresinol, and scopolin, evidenced higher relative abundance in the cooked extracts. On the other hand, only seven metabolites, such as 4-hydroxyhippuric acid, epicatechin, and leptodactylone, decreased post-heating. CONCLUSIONS: Cooking promoted little alteration in the bioactive compounds profile of immature breadfruit and thus appears to be an exploitation alternative for this perishable fruit, which seems to be a source of a large range of bioactive compounds. © 2019 Society of Chemical Industry.


Assuntos
Artocarpus/química , Compostos Fitoquímicos/química , Cromatografia Líquida de Alta Pressão , Culinária , Frutas/química , Temperatura Alta , Fenóis/química , Extratos Vegetais/química , Espectrometria de Massas em Tandem
12.
J Agric Food Chem ; 68(1): 258-266, 2020 Jan 08.
Artigo em Inglês | MEDLINE | ID: mdl-31825219

RESUMO

Screening the volatiles of cempedak [Artocarpus integer (Thunb.) Merr.] pulp for odor-active compounds by aroma extract dilution analysis and gas chromatography (GC)-olfactometry of static headspace samples revealed a total of 55 odorants, among which 47 were identified. Using stable isotopically substituted odorants as internal standards, these compounds were quantitated by GC-mass spectrometry, and odor activity values (OAVs) were calculated as ratios of the natural concentrations in cempedak pulp to the orthonasal odor detection thresholds. An aroma reconstitution model based on the 41 compounds with OAVs >1 in their natural concentrations successfully mimicked the characteristic aroma of cempedak pulp including the pronounced sulfury, oniony note which is intense in cempedak pulp but absent in jackfruit pulp. Further sensory tests finally showed that 2-(methylsulfanyl)propane, 2-(methylsulfanyl)butane, and 2-(methylsulfanyl)pentane are the key compounds responsible for this unique aroma note in cempedak pulp and vitally contribute to the aroma difference between cempedak pulp and jackfruit pulp.


Assuntos
Artocarpus/química , Odorantes/análise , Compostos Orgânicos Voláteis/química , Aromatizantes/química , Cromatografia Gasosa-Espectrometria de Massas , Humanos , Estrutura Molecular , Olfatometria , Olfato
13.
Acta Parasitol ; 65(1): 11-18, 2020 Mar.
Artigo em Inglês | MEDLINE | ID: mdl-31552583

RESUMO

AIM: To evaluate the anthelmintic activity of Anacardium occidentale shell, Illicium verum fruit, and Artocarpus heterophyllus seed to substantiate their traditional use against helminths. MATERIALS AND METHODS: In vitro anthelmintic activity of hydroalcoholic extracts of three plants was evaluated against eggs, infective larvae (L3), adult, and lactate dehydrogenase (LDH) of Haemonchus contortus of naturally infected sheep. RESULTS: The three extracts exhibited significant (P < 0.001) dose-dependent anthelmintic responses by inhibiting egg hatching and causing paralysis of larvae and mortality of worms. The extracts were most effective on egg and adult stage of H. contortus than on L3 stage at a higher concentration of 6 mg/mL. Anacardium occidentale shell exhibited maximum activity with 100% paralysis of L3 larvae. Probit analysis revealed that the extracts of A. Occidentale shell induced 50% egg hatch inhibition (LD50 = 0.0255 mg/mL), larval paralysis (LD50 = 0.196 mg/mL), and adult worm mortality (LD50 = 1.0365 mg/mL) at a lower concentration (LD50) compared with those of I. verum fruit and A. heterophyllus seed extracts. Further, all extracts significantly (P < 0.01) inhibited the LDH activity catalyzing the oxidation of lactate in adult H. contortus, with maximum level of inhibition caused by A. occidentale shell extract. CONCLUSION: Phytochemical screening of the extracts revealed the presence of alkaloids, flavonoids, tannins, saponins, and amino acids that could be responsible for the anthelmintic effects noticed. The results warrant further in vivo evaluation of these plants for potential use as anthelmintic agents.


Assuntos
Anti-Helmínticos/farmacologia , Haemonchus/efeitos dos fármacos , Extratos Vegetais/farmacologia , Anacardium/química , Animais , Artocarpus/química , Frutas/química , Haemonchus/enzimologia , Illicium/química , L-Lactato Desidrogenase , Larva/efeitos dos fármacos , Compostos Fitoquímicos/química , Compostos Fitoquímicos/farmacologia , Extratos Vegetais/química , Ovinos/parasitologia , Doenças dos Ovinos/parasitologia , Clima Tropical
14.
Int J Biol Macromol ; 142: 63-72, 2020 Jan 01.
Artigo em Inglês | MEDLINE | ID: mdl-31521655

RESUMO

In this study, a bionanocomposite based food packaging film was designed to reduce environmental hazards. Cellulose nanoparticles (CNP) were prepared from the non-edible part of jackfruit (Artocarpus heterophyllus) by alkaline treatment, bleaching, and acid hydrolysis. The newly designed bionanocomposite film consists of CNP, polyvinyl alcohol (PVA) and fennel seed essential oil (EO). The composition of the film was optimized using central composite design of response surface methodology. Quadratic models were developed for responses such as elongation at break, tensile strength, free radical scavenging (antioxidant) activity, and antimicrobial activity. The optimized film reported seven-fold increase in tensile strength and six-fold in elongation at break compared to PVA film due to incorporation of CNP. Quality of the optimized film was further confirmed by evaluating morphological features, surface characteristics, physical and thermal properties. The results suggest that the newly designed EO incorporated CNP-PVA bionanocomposite film as a better alternative for traditional food packaging materials.


Assuntos
Artocarpus/química , Celulose/química , Nanopartículas/química , Extratos Vegetais/química , Anti-Infecciosos , Antioxidantes , Bactérias/efeitos dos fármacos , Embalagem de Alimentos , Frutas/química , Nanocompostos/química , Óleos Voláteis , Álcool de Polivinil , Resistência à Tração , Difração de Raios X
15.
Nat Prod Res ; 34(15): 2229-2231, 2020 Aug.
Artigo em Inglês | MEDLINE | ID: mdl-30835534

RESUMO

A drimane-type sesquiterpene, (+)-dendocarbin L (1) together with two bisabolane-type sesquiterpenes, (+)-sydonic acid (2) and (+)-sydowic acid (3) were isolated from the mycelium of Pestalotiopsis microspora HF 12440, an endophytic fungus from the stem of Artocarpus heterophyllus. The structures of all compounds were elucidated using spectroscopic methods and by comparison with the literature. Compound 1 was isolated from the fungi for the first time, compounds 2 and 3 were firstly obtained from this endophytic fungus. Compound 3 showed cytotoxicity (IC50 2.56 µg/mL) against murine leukemia P-388 cells.


Assuntos
Artocarpus/microbiologia , Sesquiterpenos/isolamento & purificação , Xylariales/química , Animais , Antineoplásicos/isolamento & purificação , Antineoplásicos/farmacologia , Artocarpus/química , Linhagem Celular Tumoral , Leucemia/tratamento farmacológico , Leucemia/patologia , Camundongos , Estrutura Molecular , Sesquiterpenos Policíclicos , Sesquiterpenos/química , Análise Espectral
16.
Molecules ; 24(24)2019 Dec 15.
Artigo em Inglês | MEDLINE | ID: mdl-31847475

RESUMO

In this study, a combination of quadrupole time-of-flight mass spectrometry (Q-TOF-MS) and linear trap quadrupole orbitrap mass spectrometry (LTQ-Orbitrap-MS) was performed to investigate the fragmentation behaviors of prenylated flavonoids (PFs) from Artocarpus plants. Fifteen PFs were selected as the model molecules and divided into five types (groups A-E) according to their structural characteristics in terms of the position and existing form of prenyl substitution in the flavone skeleton. The LTQ-Orbitrap-MSn spectra of the [M - H]- ions for these compounds provided a wealth of structural information on the five different types of compounds. The main fragmentation pathways of group A were the ortho effect and retro Diels-Alder (RDA), and common losses of C4H10, CO, and CO2. The compounds in group B easily lose C6H12, forming a stable structure of a 1,4-dienyl group, unlike those in group A. The fragmentation pathway for group C is characterized by obvious 1,4A-, 1,4B- cracking of the C ring. The diagnostic fragmentation for group D is obvious RDA cracking of the C ring and the successive loss of CH3 and H2O in the LTQ-Orbitrap-MSn spectra. Fragmentation with successive loss of CO or CO2, ·CH3, and CH4 in the LTQ-Orbitrap-MSn spectra formed the characteristics of group E. The summarized fragmentation rules were successfully exploited to identify PFs from Artocarpus heterophyllus, a well-known Artocarpus plant, which led to the identification of a total of 47 PFs in this plant.


Assuntos
Artocarpus/química , Flavonoides/química , Extratos Vegetais/química , Raízes de Plantas/química , Espectrometria de Massas por Ionização e Dessorção a Laser Assistida por Matriz , Espectrometria de Massas em Tandem , Cromatografia Líquida de Alta Pressão/métodos , Modelos Moleculares , Estrutura Molecular
17.
Sci Rep ; 9(1): 16709, 2019 11 13.
Artigo em Inglês | MEDLINE | ID: mdl-31723189

RESUMO

In the present work, sustainable nanomaterials, cellulose, and spherical cellulose nanocrystals (SCNCs) were isolated from the non-edible parts of jackfruit (Artocarpus heterophyllus). Of the three different methods tested, sodium chlorite treatment produced the highest yield of cellulose, 20.08 ± 0.05% w/w (dry weight). Peaks observed in CP/MAS 13C NMR spectrum and FTIR frequencies revealed the presence of α-cellulose and absence of other biomass fractions like hemicellulose and lignin. XRD analysis showed a high crystallinity of 83.42%. An appearance of a sharp endothermal peak at 323 °C in DSC and decomposition patterns between 310-420 °C of TGA confirms the presence of cellulose. Further, Sulphuric acid hydrolysis was employed to produce SCNCs and examined by TEM for the morphology and by HPLC for the presence of glucose.


Assuntos
Artocarpus/química , Artocarpus/crescimento & desenvolvimento , Celulose/química , Celulose/isolamento & purificação , Nanopartículas/química , Ácidos Sulfúricos/metabolismo , Hidrólise
18.
J Chromatogr B Analyt Technol Biomed Life Sci ; 1130-1131: 121806, 2019 Nov 01.
Artigo em Inglês | MEDLINE | ID: mdl-31670106

RESUMO

Lectins are carbohydrate binding proteins with many physiological and biotechnological applications. Isolation of proteins is normally time-consuming and encompasses multiple and, sometimes, complicated steps that hinder reproducibility and yield. Affinity chromatography is an efficient way to simplify and improve protein purification, however often requiring an expensive and fragile stationary phase. In this regard, automated flow-based systems minimize the time for extraction of species from solid samples without hindering the features of batch procedures. In this work, a new inexpensive affinity-based stationary phase was developed for in-line separation of jacalin, a galactose-binding lectin from jackfruit seeds. In the flow manifold, in-line extraction of proteins was also carried out with continuous monitoring using the spectrophotometric Biuret assay. For protein determination, linear response was observed from 3.0 to 15 g L-1. The results of the analysis of protein extracts from jackfruit seeds obtained with the herein described procedure and batch procedure agreed with 95% confidence level. Quantitative extraction of proteins from jackfruit seed powder required recirculation of extraction buffer for 15 min through a lab-made polymethylmethacrylate (PMMA) column containing 200 mg of the crude seed powder. In the chromatographic step, jacalin was isolated after 300 s. Therefore, three essential steps for jacalin isolation were performed in one manifold in a fast way, minimizing sample consumption and solution handling. Additionally, the versatile and multi-task developed flow manifold can be useful for routine analysis and preparative procedures, being adaptable for the extraction and separation of other species from solid matrixes with continuous monitoring of the processes.


Assuntos
Fracionamento Químico/métodos , Cromatografia de Afinidade/métodos , Lectinas de Plantas , Proteínas de Plantas/isolamento & purificação , Artocarpus/química , Lectinas de Plantas/análise , Lectinas de Plantas/química , Lectinas de Plantas/isolamento & purificação , Proteínas de Plantas/análise , Proteínas de Plantas/química , Projetos de Pesquisa , Sementes/química
19.
Planta Med ; 85(16): 1263-1274, 2019 Nov.
Artigo em Inglês | MEDLINE | ID: mdl-31604352

RESUMO

In an effort to identify agents from natural products that inhibit protein tyrosine phosphatase 1B (PTP1B), 5 new prenylated stilbenes, (±)-styrastilbene A (1: ), styrastilbene B (2: ), and (±)-styrastilbenes C - E (3, 4: , and 7: ), along with 4 known structurally related compounds (5, 6, 8: , and 9: ), were isolated from the roots of Artocarpus styracifolius. Their structures were elucidated by spectroscopic methods, including 1D and 2D nuclear magnetic resonance (NMR), high-resolution electrospray ionization mass spectrometry (HRESIMS), ultraviolet (UV), and infrared (IR). Based on these isolates, a new plausible biosynthetic pathway for the unusual stilbene derivatives 3: -8: with a tetracyclic ring system is proposed. Among these compounds, 1: -3, 8: , and 9: displayed significant PTP1B inhibitory effects with IC50 values ranging from 2.40 (95% confidence interval [CI]: 2.21 - 2.59) to 8.80 (95% CI: 8.28 - 9.32) µM. Moreover, kinetic analysis and molecular docking simulations were performed to provide insight into the inhibition type as well as the interaction and binding mode of these active isolates with PTP1B. Our results revealed mixed-type PTP1B inhibition for all compounds tested. Docking simulations of these stilbene derivatives showed negative binding energies and close proximity to residues at the allosteric and catalytic sites of PTP1B. These findings suggest that these compounds may have a potential to be further developed as agents for the management of type 2 diabetes mellitus.


Assuntos
Artocarpus/química , Diabetes Mellitus Tipo 2/tratamento farmacológico , Inibidores Enzimáticos/farmacologia , Simulação de Acoplamento Molecular , Estrutura Molecular , Proteína Tirosina Fosfatase não Receptora Tipo 1/antagonistas & inibidores , Estilbenos/farmacologia , Raízes de Plantas/química , Prenilação , Estilbenos/química
20.
J Enzyme Inhib Med Chem ; 34(1): 1623-1632, 2019 Dec.
Artigo em Inglês | MEDLINE | ID: mdl-31480857

RESUMO

This study aimed to search the α-glucosidase inhibitors from the barks part of Artocarpus elasticus. The responsible compounds for α-glucosidase inhibition were found out as dihydrobenzoxanthones (1-4) and alkylated flavones (5-6). All compounds showed a significant enzyme inhibition toward α-glucosidase with IC50s of 7.6-25.4 µM. Dihydrobenzoxanthones (1-4) exhibited a competitive inhibition to α-glucosidase. This competitive behaviour was fully characterised by double reciprocal plots, Yang's method, and time-dependent experiments. The compound 1 manifested as the competitive and reversible simple slow-binding, with kinetic parameters k3 = 0.0437 µM-1 min-1, k4 = 0.0166 min-1, and Kiapp = 0.3795 µM. Alkylated flavones (5-6) were mixed type I (KI < KIS) inhibitors. The binding affinities (KSV) represented by all inhibitors were correlated to their concentrations and inhibitory potencies (IC50). Moreover, compounds 1 and 5 were identified as new ones named as artoindonesianin W and artoflavone B, respectively. Molecular modelling study proposed the putative binding conformation of competitive inhibitors (1-4) to α-glucosidase at the atomic level.


Assuntos
Artocarpus/química , Inibidores de Glicosídeo Hidrolases/farmacologia , Casca de Planta/química , Xantonas/farmacologia , alfa-Glucosidases/metabolismo , Relação Dose-Resposta a Droga , Fluorescência , Inibidores de Glicosídeo Hidrolases/química , Inibidores de Glicosídeo Hidrolases/isolamento & purificação , Estrutura Molecular , Relação Estrutura-Atividade , Xantonas/química , Xantonas/isolamento & purificação
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