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1.
Phytochemistry ; 198: 113143, 2022 Jun.
Artigo em Inglês | MEDLINE | ID: mdl-35240135

RESUMO

Five undescribed bis(lauric acid-12-yl)lignanoates, liglaurates A-E, along with the known methyl and glyceryl 12-caffeoyloxylaurates were isolated from the rhizomes of Drynaria roosii Nakaike. Their structures including absolute configurations were determined by HRESIMS, NMR techniques, and ECD calculation. Liglaurates A-D were isolated as the racemates, among which (±)-liglaurate A and (±)-liglaurate B were synthesized by a metal-mediated oxidative coupling reaction and further resolved as the enantiomerically pure compounds. Liglaurates (+)-A, (-)-A, (+)-B, (-)-B, (±)-C and (±)-D exhibited remarkable cytotoxic activities against HeLa cell line, with the IC50 values of 0.11 ± 0.02, 0.24 ± 0.01, 0.02 ± 0.00, 0.13 ± 0.02, 0.34 ± 0.07 and 0.17 ± 0.01 µM, respectively.


Assuntos
Antineoplásicos , Polypodiaceae , Células HeLa , Humanos , Ácidos Láuricos/análise , Estrutura Molecular , Polypodiaceae/química , Rizoma/química
2.
Molecules ; 26(6)2021 Mar 17.
Artigo em Inglês | MEDLINE | ID: mdl-33802719

RESUMO

Plant diseases reduce crop yield and quality, hampering the development of agriculture. Fungicides, which restrict chemical synthesis in fungi, are the strongest controls for plant diseases. However, the harmful effects on the environment due to continued and uncontrolled utilization of fungicides have become a major challenge in recent years. Plant-sourced fungicides are a class of plant antibacterial substances or compounds that induce plant defenses. They can kill or inhibit the growth of target pathogens efficiently with no or low toxicity, they degrade readily, and do not prompt development of resistance, which has led to their widespread use. In this study, the growth inhibition effect of 24 plant-sourced ethanol extracts on rice sprigs was studied. Ethanol extract of gallnuts and cloves inhibited the growth of bacteria by up to 100%. Indoor toxicity measurement results showed that the gallnut and glove constituents inhibition reached 39.23 µg/mL and 18.82 µg/mL, respectively. Extract treated rice sprigs were dry and wrinkled. Gallnut caused intracellular swelling and breakage of mitochondria, disintegration of nuclei, aggregation of protoplasts, and complete degradation of organelles in hyphae and aggregation of cellular contents. Protection of Rhizoctonia solani viability reached 46.8% for gallnut and 37.88% for clove in water emulsions of 1000 µg/mL gallnut and clove in the presence of 0.1% Tween 80. The protection by gallnut was significantly stronger than that of clove. The data could inform the choice of plant-sourced fungicides for the comprehensive treatment of rice sprig disease. The studied extract effectively protected rice sprigs and could be a suitable alternative to commercially available chemical fungicides. Further optimized field trials are needed to effectively sterilize rice paddies.


Assuntos
Misturas Complexas/farmacologia , Oryza/efeitos dos fármacos , Extratos Vegetais/farmacologia , Rhizoctonia/efeitos dos fármacos , Rhus/química , Syzygium/química , Cromatografia por Troca Iônica , Misturas Complexas/toxicidade , Etanol/química , Eugenol/análise , Fungicidas Industriais/farmacologia , Ácidos Láuricos/análise , Espectrometria de Massas , Microscopia Eletrônica de Varredura , Microscopia Eletrônica de Transmissão , Mitocôndrias/efeitos dos fármacos , Mitocôndrias/ultraestrutura , Micélio/efeitos dos fármacos , Micélio/ultraestrutura , Oryza/microbiologia , Doenças das Plantas/microbiologia , Extratos Vegetais/toxicidade
3.
Lipids ; 56(4): 423-435, 2021 07.
Artigo em Inglês | MEDLINE | ID: mdl-33886120

RESUMO

Implementing insects, such as the black soldier fly larvae (BSFL), as animal feed commonly includes the previous removal of substantial amounts of fat. This fat may represent an as yet underutilized energy source for livestock. However, transfer of lauric and myristic acid, prevalent in BSFL fat and undesired in human nutrition, into animal-source foods like eggs may limit its implementation. To quantify this, a laying hen experiment was performed comprising five different diets (10 hens/diet). These were a control diet with soybean oil and meal and a second diet with soybean oil but with partially defatted BSFL meal as protein source. The other three diets were based on different combinations of partially defatted BSFL meal and fat obtained by two different production methods. Lauric acid made up half of the BSFL fat from both origins. Both BSFL fats also contained substantial amounts of myristic and palmitic acid. However, in the insect-based diets, the net transfer from diet to egg yolk was less than 1% for lauric acid, whereas the net transfer for myristic and palmitic acid was about 30% and 100%, respectively. The net transfer did not vary between BSFL originating from production on different larval feeding substrates. The results illustrate that hens are able to metabolize or elongate very large proportions of ingested lauric acid and myristic acid, which are predominant in the BSFL lipids (together accounting for as much as 37 mol%), such that they collectively account for less than 3.5 mol% of egg yolk fatty acids.


Assuntos
Ração Animal , Dípteros/química , Gema de Ovo/química , Ácidos Láuricos/metabolismo , Ácido Mirístico/metabolismo , Animais , Galinhas , Ácidos Graxos/análise , Ácidos Graxos/química , Feminino , Larva/química , Ácidos Láuricos/análise , Ácido Mirístico/análise , Óleo de Soja
4.
Biotechnol Bioeng ; 117(8): 2377-2388, 2020 08.
Artigo em Inglês | MEDLINE | ID: mdl-32369187

RESUMO

Selective oxy-functionalization of nonactivated C-H bonds is a long-standing "dream reaction" of organic synthesis for which chemical methodology is not well developed. Mono-oxygenase enzymes are promising catalysts for such oxy-functionalization to establish. Limitation on their applicability arises from low reaction output. Here, we showed an integrated approach of process engineering to the intensification of the cytochrome P450 BM3-catalyzed hydroxylation of dodecanoic acid (C12:0). Using P450 BM3 together with glucose dehydrogenase for regeneration of nicotinamide adenine dinucleotide phosphate (NADPH), we compared soluble and co-immobilized enzymes in O2 -gassed and pH-controlled conversions at high final substrate concentrations (≥40mM). We identified the main engineering parameters of process output (i.e., O2 supply; mixing correlated with immobilized enzyme stability; foam control correlated with product isolation; substrate solubilization) and succeeded in disentangling their complex interrelationship for systematic process optimization. Running the reaction at O2 -limited conditions at up to 500-ml scale (10% dimethyl sulfoxide; silicone antifoam), we developed a substrate feeding strategy based on O2 feedback control. Thus, we achieved high reaction rates of 1.86g·L-1 ·hr-1 and near complete conversion (≥90%) of 80mM (16g/L) C12:0 with good selectivity (≤5% overoxidation). We showed that "uncoupled reaction" of the P450 BM3 (~95% utilization of NADPH and O2 not leading to hydroxylation) with the C12:0 hydroxylated product limited the process efficiency at high product concentration. Hydroxylated product (~7g; ≥92% purity) was recovered from 500ml reaction in 82% yield using ethyl-acetate extraction. Collectively, these results demonstrate key engineering parameters for the biocatalytic oxy-functionalization and show their integration into a coherent strategy for process intensification.


Assuntos
Proteínas de Bactérias/metabolismo , Sistema Enzimático do Citocromo P-450/metabolismo , Enzimas Imobilizadas/metabolismo , Ácidos Láuricos , NADPH-Ferri-Hemoproteína Redutase/metabolismo , Proteínas de Bactérias/química , Proteínas de Bactérias/genética , Biotecnologia , Sistema Enzimático do Citocromo P-450/química , Sistema Enzimático do Citocromo P-450/genética , Enzimas Imobilizadas/química , Enzimas Imobilizadas/genética , Ácidos Láuricos/análise , Ácidos Láuricos/química , Ácidos Láuricos/metabolismo , NADP/metabolismo , NADPH-Ferri-Hemoproteína Redutase/química , NADPH-Ferri-Hemoproteína Redutase/genética , Oxigênio/metabolismo , Proteínas Recombinantes de Fusão/química , Proteínas Recombinantes de Fusão/genética , Proteínas Recombinantes de Fusão/metabolismo
5.
Nat Prod Res ; 34(4): 545-548, 2020 Feb.
Artigo em Inglês | MEDLINE | ID: mdl-30257572

RESUMO

The chemical composition of Tussilago farfara L. essential oil from the Saguenay-Lac-St-Jean region of Quebec, Canada was analyzed by gas chromatography-flame ionisation detector (GC-FID) and gas chromatography-mass spectrometry (GC-MS), and the antibacterial activity of the oil was tested against Escherichia coli and Staphylococcus aureus. Forty-five (45) compounds were identified from the GC profile. The main components were 1-nonene (40.1%), α-phellandrene (26.0%) and ρ-cymene (6.6%). The essential oil demonstrated antibacterial activity against E. coli (MIC50 = 468 µg·mL-1; MIC90 = 6869 µg·mL-1) and S. aureus (MIC50 = 368 µg·mL-1; MIC90 = 773 µg·mL-1). Dodecanoic acid was found to be active against both bacteria having a MIC50 and MIC90 of 16.4 µg·mL-1 and 95 µg·mL-1, respectively for E. coli and a MIC50 and MIC90 of 9.8 µg·mL-1 and 27.3 µg·mL-1, respectively for S. aureus. In addition, 1-decene and (E)-cyclodecene were also found to be active against E. coli.


Assuntos
Antibacterianos/isolamento & purificação , Óleos Voláteis/química , Tussilago/química , Alcanos/análise , Alcanos/farmacologia , Antibacterianos/química , Antibacterianos/farmacologia , Bactérias/efeitos dos fármacos , Ciclodecanos/análise , Ciclodecanos/farmacologia , Monoterpenos Cicloexânicos/análise , Cimenos/análise , Escherichia coli/efeitos dos fármacos , Cromatografia Gasosa-Espectrometria de Massas , Ácidos Láuricos/análise , Ácidos Láuricos/farmacologia , Testes de Sensibilidade Microbiana , Quebeque , Staphylococcus aureus/efeitos dos fármacos
6.
J Chem Ecol ; 45(11-12): 901-913, 2019 Dec.
Artigo em Inglês | MEDLINE | ID: mdl-31773376

RESUMO

Trail pheromones deposited by ants lead nestmates to food sources. Based on previous evidence that the trail pheromone of the carpenter ant Camponotus modoc originates from the hindgut, our objective in this study was to identify the key component(s) of the pheromone. We collected C. modoc colonies from conifer forests and maintained them in an outdoor enclosure near our laboratory for chemical analyses and behavioral experiments. In gas chromatographic-electroantennographic detection and gas chromatography-mass spectrometric analyses of worker ant hindgut extracts, we identified five candidate components: 2,4-dimethylhexanoic acid, 2,4-dimethyl-5-hexanolide, pentadecane, dodecanoic acid and 3,4-dihydro-8-hydroxy-3,5,7-trimethylisocoumarin. In a series of trail-following experiments, ants followed trails of synthetic 2,4-dimethyl-5-hexanolide, a blend of the five compounds, and hindgut extract over similar distances, indicating that the hexanolide accounted for the entire behavioral activity of the hindgut extract. The hexanolide not only mediated orientation of C. modoc foragers on trails, it also attracted them over distance, indicating a dual function. Further analyses and bioassays with racemic and stereoselectively synthesized hexanolides revealed that the ants produce, and respond to, the (2S,4R,5S)-stereoisomer. The same stereoisomer is a trail pheromone component in several Camponotus congeners, indicating significant overlap in their respective trail pheromone communication systems.


Assuntos
Misturas Complexas/análise , Feromônios/análise , Alcanos/análise , Animais , Formigas , Comportamento Animal , Técnicas Biossensoriais/métodos , Caproatos/análise , Cumarínicos/análise , Glândulas Exócrinas/metabolismo , Cromatografia Gasosa-Espectrometria de Massas/métodos , Intestinos/química , Ácidos Láuricos/análise , Estereoisomerismo
7.
Ecotoxicol Environ Saf ; 183: 109559, 2019 Nov 15.
Artigo em Inglês | MEDLINE | ID: mdl-31408822

RESUMO

The occurrence of perfluoroalkyl substances (PFASs) was for the first time investigated in various working microenvironments (internet cafes, electronics shops, coffee shops, restaurants, etc.) in Thessaloniki, Greece, using the dust trapped by central air conditioner (A/C) filters. Perfluorooctane sulfonic acid (PFOS) was found in the range from 16 to 227 ng g-1, however it was detectable in only 30% of samples. On the contrary, perfluorohexanoic acid (PFHxA) was found in 85% of samples in the range from 3.6 to 72.5 ng g-1, while 90-95% of samples exhibited perfluorooctanoic acid (PFOA), perfluorodecanoic acid (PFDcA) and perfluorododecanoic acid (PFDoDA) in the range from 10-653 ng g-1, 3.2-7.4 ng g-1 and 3.8-13.1 ng g-1, respectively. The PFAS profile varied largely among the different microenvironment categories suggesting different sources. Estimated daily intakes through dust ingestion were calculated.


Assuntos
Poluição do Ar em Ambientes Fechados/análise , Poeira/análise , Monitoramento Ambiental/métodos , Fluorocarbonos/análise , Exposição por Inalação/análise , Ar Condicionado , Filtros de Ar , Ácidos Alcanossulfônicos/análise , Caproatos/análise , Caprilatos/análise , Ácidos Decanoicos/análise , Grécia , Ácidos Láuricos/análise
8.
Chemosphere ; 228: 640-648, 2019 Aug.
Artigo em Inglês | MEDLINE | ID: mdl-31063911

RESUMO

Perfluoroalkyl substances (PFASs) were investigated in filter-feeding shellfish collected from 2013 to 2017 along the English Channel, Atlantic and Mediterranean coasts of France. PFOS (perfluorooctane sulfonate), PFTrDA (perfluorotridecanoic acid), PFTeDA (perfluorotetradecanoic acid), PFDoDA (perfluorododecanoic acid) and PFUnDA (perfluoroundecanoic acid) were detected in more than 80% of samples, thus indicating widespread contamination of the French coastal environment by these chemicals. The distribution of PFAS concentrations showed differences according to sampling locations and years. PFOS was the predominant PFAS in most samples collected from English Channel and Atlantic coasts until 2014, but the opposite was observed in 2015, 2016 and 2017, while perfluoroalkyl carboxylic acids (PFCAs) prevailed in Mediterranean samples in all study years. Among PFCAs, PFTrDA showed the highest maximum (1.36 ng g-1 ww) and median (0.077 ng g-1 ww) concentrations in 2016-2017. Other PFAS median concentrations were within the 0.014 (PFNA) - 0.055 (PFTeDA) ng g-1 ww range. The profiles determined each year in most Mediterranean samples suggest distinctive sources. PFOS median concentrations showed a significant decrease over the study years, from 0.118 to 0.126 ng g-1 ww in 2013-2015 to 0.066 ng g-1 ww in 2016 and 2017. ∑PFCAs showed no trends in concentration ranges over the same years. The shift in PFAS profiles from PFOS to long-chain PFCAs over the study period reflects PFOS production phase-out, combined with continuous inputs of PFCAs into the marine environment. These results provide reference data for future studies of the occurrence of contaminants of emerging concern on European coasts.


Assuntos
Bivalves/química , Crassostrea/química , Fluorocarbonos/análise , Poluentes Químicos da Água/análise , Ácidos Alcanossulfônicos/análise , Animais , Monitoramento Ambiental , Ácidos Graxos/análise , França , Ácidos Láuricos/análise , Mar Mediterrâneo , Frutos do Mar/análise , Análise Espaço-Temporal
9.
Meat Sci ; 153: 26-34, 2019 Jul.
Artigo em Inglês | MEDLINE | ID: mdl-30861487

RESUMO

Pork quality characteristics related to the dietary substitution of soybean meal by the micro-alga Spirulina (Arthrospira platensis) or black soldier fly (Hermetia illucens) partly-defatted larval meal were observed. Through a duplicated study totalling 48 individually-fed barrows (Pietrain × (Large White × Landrace)) allocated into two experimental groups and a control, the effect of dietary protein source on physico-chemical and sensory pork quality was monitored under current industrial packaging conditions (highly­oxygenated modified atmosphere packaging). The results show that physico-chemical characteristics are not degraded by including alternative protein sources in pig diets. Hermetia illucens increased lauric acid levels in backfat indicating that this fatty acid may be suitable as a biomarker for Hermetia illucens-fed pork. This goes to show that protein alternatives do not compromise pork quality.


Assuntos
Ração Animal/análise , Carne Vermelha/análise , Simuliidae/química , Spirulina/química , Tecido Adiposo/química , Fenômenos Fisiológicos da Nutrição Animal , Animais , Dieta/veterinária , Proteínas Alimentares , Larva/química , Ácidos Láuricos/análise , Masculino , Simuliidae/crescimento & desenvolvimento , Sus scrofa/crescimento & desenvolvimento
10.
Food Chem ; 275: 739-745, 2019 Mar 01.
Artigo em Inglês | MEDLINE | ID: mdl-30724257

RESUMO

Palm mid-fraction (PMF), which has a high content of symmetric POP, was converted to asymmetric PPO (APMF) via acyl migration. After solvent fractionation, the liquid phase of acyl migrated PMF (APMF-L) was obtained and blended with hydrogenated coconut oil (HCO, 50:50, w/w) to produce a fat blend (namely, an alternative fat blend) which had reduced saturated fatty acid content while having similar melting behavior to HCO. In an alternative fat blend, the major fatty acids were lauric (27.94), palmitic (26.93) and oleic (15.75 mol%) acid. The solid fat index was quite similar to that of HCO, especially at 28-44 °C. Nevertheless, an alternative fat blend had lower saturated fatty acid content, by 18%, compared to HCO. The content of highly atherogenic myristic acid was reduced by approximately 40%. The alternative fat blend in this study could be used as a raw material for non-dairy cream with low saturated fat content.


Assuntos
Cromatografia Gasosa , Óleo de Coco/química , Ácidos Graxos/análise , Varredura Diferencial de Calorimetria , Óleo de Coco/metabolismo , Emulsões/química , Hidrogenação , Ácidos Láuricos/análise , Ácido Oleico/análise , Ácido Palmítico/análise , Óleos de Plantas/química , Óleos de Plantas/metabolismo
11.
Artigo em Inglês | MEDLINE | ID: mdl-30265940

RESUMO

Modified coconut oil (MCO) obtained from the glycerolysis of virgin coconut oil (VCO) and glycerol under various conditions should have different amounts of bioactive fatty acids (FAs) and acylglycerols (AGs). Methods were developed to analyze lauric acid (LA), monolaurin (ML), dilaurin (DL), and trilaurin (TL) in MCO samples using gas chromatography - flame ionization detector (GC-FID) and high performance liquid chromatography - evaporative light scattering detector (HPLC-ELSD). The purpose of this research is to optimize and compare GC-FID and HPLC-ELSD methods for determination of LA, ML, DL, and TL in MCO samples. All the standard curves exhibited good linearity (R2 ≥ 0.9995), except for that of LA analyzed by HPLC-ELSD (R2 = 0.9971). The limits of detection (LODs) and quantification (LOQs) were found to be in the range of 0.033-0.260 mg/ml and 0.099-0.789 mg/ml for the GC-FID method and 0.040-0.421 mg/ml and 0.122-1.277 mg/ml for the HPLC-ELSD method, respectively. The GC-FID method (LOD ≤ 0.033 mg/ml) was more sensitive than HPLC-ELSD method (LOD ≤ 0.421 mg/ml) and showed satisfactory recoveries for LA analysis while HPLC-ELSD method (LOD ≤ 0.040 mg/ml) was more sensitive than GC-FID method (LOD ≤ 0.260 mg/ml) and exhibited acceptable recoveries for TL analysis. Both methods were applied to determine the MCO samples produced under varied conditions for glycerolysis. The results revealed that the developed GC-FID method is suitable for the quantification of LA, ML, and DL while the developed HPLC-ELSD method is appropriate for the determination of ML, DL, and TL. Both developed GC-FID and HPLC-ELSD methods produced reproducible results for the determination of LA, ML, DL, and TL in MCO samples.


Assuntos
Cromatografia Gasosa/métodos , Cromatografia Líquida de Alta Pressão/métodos , Óleo de Coco/química , Ácidos Láuricos/análise , Triglicerídeos/análise , Limite de Detecção , Modelos Lineares , Reprodutibilidade dos Testes
12.
Toxicol Lett ; 294: 193-204, 2018 Sep 15.
Artigo em Inglês | MEDLINE | ID: mdl-29800716

RESUMO

The eosinophilia-myalgia syndrome (EMS) outbreak that occurred in the USA and elsewhere in 1989 was caused by the ingestion of Showa Denko K.K. (SD) L-tryptophan (L-Trp). "Six compounds" detected in the L-Trp were reported as case-associated contaminants. Recently the final and most statistically significant contaminant, "Peak AAA" was structurally characterized. The "compound" was actually shown to be two structural isomers resulting from condensation reactions of L-Trp with fatty acids derived from the bacterial cell membrane. They were identified as the indole C-2 anteiso (AAA1-343) and linear (AAA2-343) aliphatic chain isomers. Based on those findings, we utilized a combination of on-line HPLC-electrospray ionization mass spectrometry (LC-MS), as well as both precursor and product ion tandem mass spectrometry (MS/MS) to facilitate identification of a homologous family of condensation products related to AAA1-343 and AAA2-343. We structurally characterized eight new AAA1-XXX/AAA2-XXX contaminants, where XXX represents the integer molecular ions of all the related homologs, differing by aliphatic chain length and isomer configuration. The contaminants were derived from the following fatty acids of the bacterial cell membrane, 5-methylheptanoic acid (anteiso-C8:0) for AAA1-315; n-octanoic acid (n-C8:0) for AAA2-315; 6-methyloctanoic acid (anteiso-C9:0) for AAA1-329; n-nonanoic acid (n-C9:0) for AAA2-329; 10-methyldodecanoic acid (anteiso-C13:0) for AAA1-385; n-tridecanoic acid (n-C13:0) for AAA2-385; 11-methyltridecanoic acid (anteiso-C14:0) for AAA1-399; and n-tetradecanoic acid (n-C14:0) for AAA2-399. The concentration levels for these contaminants were estimated to be 0.1-7.9 µg / 500 mg of an individual SD L-Trp tablet or capsule The structural similarity of these homologs to case-related contaminants of Spanish Toxic Oil Syndrome (TOS) is discussed.


Assuntos
Suplementos Nutricionais/análise , Síndrome de Eosinofilia-Mialgia/induzido quimicamente , Ácidos Graxos/toxicidade , Contaminação de Alimentos , Indóis/toxicidade , Triptofano/análogos & derivados , Bacillus amyloliquefaciens/metabolismo , Caprilatos/análise , Caprilatos/química , Caprilatos/isolamento & purificação , Caprilatos/toxicidade , Centers for Disease Control and Prevention, U.S. , Cromatografia Líquida de Alta Pressão , Suplementos Nutricionais/efeitos adversos , Ácidos Graxos/análise , Ácidos Graxos/química , Ácidos Graxos/isolamento & purificação , Fermentação , Ácidos Heptanoicos/análise , Ácidos Heptanoicos/química , Ácidos Heptanoicos/isolamento & purificação , Ácidos Heptanoicos/toxicidade , Humanos , Indóis/análise , Indóis/química , Indóis/isolamento & purificação , Ácidos Láuricos/análise , Ácidos Láuricos/química , Ácidos Láuricos/isolamento & purificação , Ácidos Láuricos/toxicidade , Metilação , Estrutura Molecular , Miristatos/análise , Miristatos/química , Miristatos/isolamento & purificação , Miristatos/toxicidade , Espectrometria de Massas por Ionização por Electrospray , Estereoisomerismo , Triptofano/análise , Triptofano/química , Triptofano/isolamento & purificação , Estados Unidos
13.
Food Chem ; 250: 67-74, 2018 Jun 01.
Artigo em Inglês | MEDLINE | ID: mdl-29412929

RESUMO

Melissa officinalis (lemon balm) and its extracts have been frequently reported as possessing bioactive properties, offering the potential for use in development/enrichment of food products with additional functional capabilities, providing health benefits to consumers. The antioxidant, antibacterial and antifungal activity of lemon balm extract, as well as its potential hepatotoxicity were thoroughly evaluated. The extracts were then incorporated into cupcakes and their preserving effect, chemical composition, colour parameters and antioxidant activity were compared with those provided by potassium sorbate. In general, the variables with the largest differences among different storage times were energy level, sucrose, glucose, palmitic acid (C6:0) and oleic acid (C18:1n9). On the other hand, L∗ (top), a∗ (top), b∗ (top), pH, capric acid (C10:0) and lauric acid (C12:0) showed the greatest variation according to cupcake formulation. The results observed indicate that the lemon balm extract rich in rosmarinic acid can provide advantageous functional properties to bakery products.


Assuntos
Cinamatos/química , Depsídeos/química , Aditivos Alimentares/farmacologia , Melissa/química , Extratos Vegetais/química , Extratos Vegetais/farmacologia , Animais , Anti-Infecciosos/farmacologia , Antioxidantes/química , Antioxidantes/farmacologia , Pão , Ácidos Decanoicos/análise , Aditivos Alimentares/química , Armazenamento de Alimentos , Ácidos Láuricos/análise , Extratos Vegetais/toxicidade , Ácido Sórbico , Ácido Rosmarínico
14.
Plant Foods Hum Nutr ; 71(4): 410-415, 2016 Dec.
Artigo em Inglês | MEDLINE | ID: mdl-27679437

RESUMO

The coconut oil (CO) contains 91 % of saturated fatty acids in which 72 % are medium chain fatty acids (MCFAs) like lauric, capric and caprylic acids. In contrast to animal fat, coconut oil has no cholesterol. Despite this fact, CO is sidelined among other vegetable oils due to the health hazards attributed to the saturated fatty acids. Though various medicinal effects of CO have been reported including the hypolipidemic activity, people are still confused in the consumption of this natural oil. In silico analyses and wet lab experiments have been carried out to identify the hypolipidemic properties of MCFAs and phenolic acids in CO by using different protein targets involved in cholesterol synthesis. The molecular docking studies were carried out using CDOCKER protocol in Accelery's Discovery Studio, by taking different proteins like HMG- CoA reductase and cholesterol esterase as targets and the different phytocompounds in coconut as ligands. Molecular docking highlighted the potential of lauric acid in inhibiting the protein targets involved in hyperlipidemics. Further, validation of in silico results was carried out through in vivo studies. The activity of key enzymes HMG- CoA reductase and lipoprotein lipase were found reduced in animals fed with lauric acid and CO.


Assuntos
Hipolipemiantes/farmacocinética , Ácidos Láuricos/farmacologia , Óleos de Plantas/química , Animais , Aspirina/farmacologia , Atorvastatina/farmacologia , Colesterol/sangue , Óleo de Coco , Relação Dose-Resposta a Droga , Ácidos Graxos/análise , Hidroximetilglutaril-CoA Redutases/metabolismo , Hipolipemiantes/análise , Ácidos Láuricos/análise , Masculino , Modelos Animais , Simulação de Acoplamento Molecular , Ratos , Ratos Sprague-Dawley , Reprodutibilidade dos Testes , Esterol Esterase/metabolismo , Triglicerídeos/sangue
15.
J Hazard Mater ; 320: 591-601, 2016 Dec 15.
Artigo em Inglês | MEDLINE | ID: mdl-27501882

RESUMO

An innovative approach that couples electrokinetics with microbial degradation to breakdown cycloparaffinic hydrocarbons in soils is described. Soils were spiked with cyclododecane, used as a model pollutant, at approximately 1000mgkg-1. A mixture of petroleum-utilizing bacteria was added to achieve about 106-107 CFUg-1. Then, three treatments were applied for 25 days: (1) no electric field, control; (2) a constant voltage gradient of 1.3Vcm-1 in one direction; and (3) the same electric field, but with periodical switching of polarity. The degradation pathway of cyclododecane was not changed by the electric field, but the dynamic processes were remarkably enhanced, especially when the electric field was periodically switched. After 25 days, 79.9% and 87.0% of the cyclododecane was degraded in tests 2 and 3, respectively; both much higher than the 61.5% degraded in test 1. Analysis of the intermediate products strongly indicated that the competitive advantage of the electric field was the increase in ring-breaking of cyclododecane, resulting in greater concentrations of linear substances that were more susceptible to microbial attack, that is, ß-oxidation. The conditions near the cathode were more favorable for the growth and metabolism of microorganisms, which also enhanced ß-oxidation of the linear alkanoic acids. Therefore, when the electric field polarity was periodically switched, the functions of both the anode and cathode electrodes were applied across the whole soil cell, further increasing the degradation efficiency.


Assuntos
Cicloparafinas/isolamento & purificação , Recuperação e Remediação Ambiental/métodos , Poluentes do Solo/isolamento & purificação , Biodegradação Ambiental , Cicloparafinas/química , Eletricidade , Ácidos Láuricos/análise , Oxirredução , Poluição por Petróleo , Poluentes do Solo/química
16.
J Chromatogr A ; 1461: 78-83, 2016 Aug 26.
Artigo em Inglês | MEDLINE | ID: mdl-27473511

RESUMO

Cocamidopropyl betaine (CAPB) is a common surfactant widely used in personal care products. Dimethylaminopropylamine (DMAPA) and lauramidopropyldimethylamine (LAPDMA) are two chemicals present as impurities in CAPB and have been reported as skin sensitizers. A rapid and sensitive ultra-high performance liquid chromatography-tandem mass spectrometry (UHPLC-MS/MS) method, using a core shell hydrophilic interaction liquid chromatography (HILIC) column, has been developed to quantify DMAPA and LAPDMA in cosmetic products. Corresponding stable isotopically labeled analogues of the above native compounds were used as internal standards to compensate for matrix effect and for loss of recovery. Each sample was first screened to determine whether the sample needed to be diluted to minimize matrix effects as well as to fit the calibration range. The concept of matrix effect factor (MEF) was introduced to quantitatively evaluate each sample with a unique matrix using the internal standards. Recoveries at three spiking levels of low, medium, and high concentrations ranged from 98.4 to 112% with RSDs less than 5%. This method has been validated and is the first UHPLC-MS/MS method, which uses core shell HILIC column and stable isotopically labeled internal standards to simultaneously determine these two CAPB impurities in cosmetic products.


Assuntos
Betaína/análogos & derivados , Cosméticos/química , Ácidos Láuricos/análise , Propilaminas/análise , Tensoativos/análise , Betaína/análise , Cromatografia Líquida de Alta Pressão/métodos , Diaminas , Interações Hidrofóbicas e Hidrofílicas , Espectrometria de Massas em Tandem/métodos
17.
J Oleo Sci ; 65(4): 311-8, 2016.
Artigo em Inglês | MEDLINE | ID: mdl-26972464

RESUMO

The aim of this study was analyze the effect of jasmonic acid (JA) and abscisic acid (ABA) as elicitors on fatty acids profile (FAP), phenolic compounds (PC) and antioxidant capacity (AC) in callus of Thevetia peruviana. Schenk & Hildebrandt (SH) medium, supplemented with 2 mg/L 2, 4-dichlorophenoxyacetic (2, 4-D) and 0.5 mg/L kinetin (KIN) was used for callus induction. The effect of JA (50, 75 and 100 µM) and ABA (10, 55 and 100 µM) on FAP, PC and AC were analyzed using a response surface design. A maximum of 2.8 mg/g of TPC was obtained with 100 plus 10 µM JA and ABA, respectively, whereas AC maximum (2.17 µg/mL) was obtained with 75 plus 100 µM JA and ABA, respectively. The FAP was affected for JA but not for ABA. JA increased cis-9, cis-12-octadecadienoic acid and decreased dodecanoic acid. Eight fatty acids were identified by GC-MS analysis and cis-9-octadecenoic acid (18:1) was the principal fatty acid reaching 76 % in treatment with 50 µM JA plus 55 µM ABA. In conclusion, JA may be used in T. peruviana callus culture for obtain oil with different fatty acids profile.


Assuntos
Ácido Abscísico/farmacologia , Antioxidantes/análise , Ciclopentanos/farmacologia , Ácidos Graxos/análise , Oxilipinas/farmacologia , Fenóis/análise , Thevetia/química , Acetatos , Ácidos Graxos/isolamento & purificação , Cromatografia Gasosa-Espectrometria de Massas , Cinetina , Ácidos Láuricos/análise , Ácidos Esteáricos/análise
18.
Arch Toxicol ; 90(6): 1383-97, 2016 Jun.
Artigo em Inglês | MEDLINE | ID: mdl-26168851

RESUMO

Perfluorododecanoic acid (PFDoA) is a ubiquitous environmental pollutant known to cause hepatocellular hypertrophy; however, the mechanisms of hepatotoxicity remain poorly understood. In this study, male rats were exposed to 0, 0.05, 0.2 and 0.5 mg/kg/day of PFDoA for 110 days. After two-dimensional differential gel electrophoresis and MALDI-TOF/TOF analysis, 73 differentially expressed proteins involved in lipid metabolism, inflammation, stress response and other functions were successfully identified. Among them, six significantly changed proteins (CTE1, MTE1, HADHA, ECH1, ALDH2 and CPS1) were found to be regulated by peroxisome proliferator-activated receptor alpha (PPARα). The anti-oxidant enzyme activity assays of superoxide dismutase and glutathione peroxidase and the content of thiobarbituric acid-reactive substances in the liver implied that PFDoA caused oxidative stress. The mRNA levels of PPARα in rat primary hepatocytes were knocked down by lentivirus-mediated RNAi. Furthermore, targeted protein levels of CTE1 and MTE1 were down-regulated, while those of HADHA, ALDH2 and CPS1 were up-regulated. After PFDoA exposure, however, the targeted protein levels of CTE1 and ALDH2 increased compared with those of the knockdown untreated group. The reactive oxygen species (ROS) content in rat hepatocytes assayed by flow cytometry significantly increased in the PPARα knockdown groups, consistent with the PPARα antagonist GW6471- and agonist WY14643-treated groups. These results strongly suggested that PPARα played an important role in suppressing ROS content in hepatocytes following PFDoA exposure.


Assuntos
Poluentes Ambientais/toxicidade , Hepatócitos/efeitos dos fármacos , Ácidos Láuricos/toxicidade , Fígado/efeitos dos fármacos , PPAR alfa/metabolismo , Espécies Reativas de Oxigênio/metabolismo , Animais , Antioxidantes/metabolismo , Western Blotting , Células Cultivadas , Relação Dose-Resposta a Droga , Eletroforese em Gel Bidimensional , Poluentes Ambientais/análise , Citometria de Fluxo , Fluorocarbonos , Técnicas de Silenciamento de Genes , Hepatócitos/enzimologia , Hepatócitos/metabolismo , Ácidos Láuricos/análise , Fígado/enzimologia , Fígado/metabolismo , Masculino , PPAR alfa/genética , Cultura Primária de Células , Ratos Sprague-Dawley , Espectrometria de Massas por Ionização e Dessorção a Laser Assistida por Matriz
19.
Chem Biodivers ; 12(4): 615-26, 2015 Apr.
Artigo em Inglês | MEDLINE | ID: mdl-25879505

RESUMO

Acacia cyanophylla Lindl. (Fabaceae), synonym Acacia saligna (Labill.) H. L.Wendl., native to West Australia and naturalized in North Africa and South Europe, was introduced in Tunisia for rangeland rehabilitation, particularly in the semiarid zones. In addition, this evergreen tree represents a potential forage resource, particularly during periods of drought. A. cyanophylla is abundant in Tunisia and some other Mediterranean countries. The chemical composition of the essential oils obtained by hydrodistillation from different plant parts, viz., roots, stems, phyllodes, flowers, and pods (fully mature fruits without seeds), was characterized for the first time here. According to GC-FID and GC/MS analyses, the principal compound in the phyllode and flower oils was dodecanoic acid (4), representing 22.8 and 66.5% of the total oil, respectively. Phenylethyl salicylate (8; 34.9%), heptyl valerate (3; 17.3%), and nonadecane (36%) were the main compounds in the root, stem, and pod oils, respectively. The phyllode and flower oils were very similar, containing almost the same compounds. Nevertheless, the phyllode oil differed from the flower oil for its higher contents of hexahydrofarnesyl acetone (6), linalool (1), pentadecanal, α-terpineol, and benzyl benzoate (5) and its lower content of 4. Principal component and hierarchical cluster analyses separated the five essential oils into four groups, each characterized by its main constituents. Furthermore, the allelopathic activity of each oil was evaluated using lettuce (Lactuca sativa L.) as a plant model. The phyllode, flower, and pod oils exhibited a strong allelopathic activity against lettuce.


Assuntos
Acacia/química , Alelopatia , Óleos Voláteis/química , Flores/química , Cromatografia Gasosa-Espectrometria de Massas , Ácidos Láuricos/análise , Lactuca/efeitos dos fármacos , Lactuca/crescimento & desenvolvimento , Óleos Voláteis/análise , Óleos Voláteis/farmacologia , Óleos de Plantas/química , Raízes de Plantas/química , Caules de Planta/química , Análise de Componente Principal , Salicilatos/química , Salicilatos/isolamento & purificação , Tunísia
20.
J Oleo Sci ; 64(2): 153-9, 2015.
Artigo em Inglês | MEDLINE | ID: mdl-25748375

RESUMO

A comparative study was done on the production of different medium chain fatty acid (MCFA) rich mustard oil using a stirred tank batchreactor (STBR) and packed bed bio reactor (PBBR) using three commercially available immobilised lipases viz. Thermomyces lanuginosus, Candida antarctica and Rhizomucor meihe. Three different MCFAs capric, caprylic and lauric acids were incorporated in the mustard oil. Reaction parameters, such as substrate molar ratio, reaction temperature and enzyme concentration were standardized in the STBR and maintained in the PBBR. To provide equal time of residence between the substrate and enzyme in both the reactors for the same amount of substrates, the substrate flow rate in the PBBR was maintainedat 0.27 ml/min. Gas liquid chromatography was used to monitor the incorporation of MCFA in mustard oil. The study showed that the PBBR was more efficient than the STBR in the synthesis of structured lipids with less migration of acyl groups. The physico-chemical parameters of the product along with fatty acid composition in all positions and sn-2 positions were also determined.


Assuntos
Reatores Biológicos , Caprilatos/química , Enzimas Imobilizadas/química , Ácidos Láuricos/química , Lipase/química , Mostardeira/química , Óleos de Plantas/química , Óleos de Plantas/síntese química , Caprilatos/análise , Fenômenos Químicos , Fungos/enzimologia , Cromatografia Gasosa-Espectrometria de Massas , Ácidos Láuricos/análise , Temperatura , Fatores de Tempo
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