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1.
Food Chem ; 304: 125425, 2020 Jan 30.
Artigo em Inglês | MEDLINE | ID: mdl-31476549

RESUMO

Ceramide 2-aminoethylphosphonate (CAEP) is a type of phosphonosphingolipids with potential trophic activity. In this work, complicated CAEP species from different aquatic products were comprehensively identified and semi-quantified by utilizing normal phase liquid chromatography/Q-Exactive mass spectrometry (NPLC/Q-Exactive-MS). We elucidated the fragment schemes of CAEP molecules and found the presence of methylated CAEP (Me-CAEP) species. Remarkably, quantitative results revealed that Loligo chinensis had the highest CAEP content of 4.9 ±â€¯0.4 mg/g dry weight and the most complex molecular species composition, whereas Asterias amurenis had the lowest CAEP content of 1.9 ±â€¯0.6 mg/g dry weight. The most common molecule was CAEP (d19:3-16:0). Additionally, statistical analysis revealed that five aquatic products can be effectively distinguished from their CAEP species; thus, CAEP molecules can play an important role in identifying processed products from aquatic products.

2.
J Agric Food Chem ; 2019 Nov 06.
Artigo em Inglês | MEDLINE | ID: mdl-31657926

RESUMO

EPA-enriched phosphoethanolamine plasmalogens (EPA-pPE), widely present in marine creatures, is a unique glycerophospholipid with EPA at the sn-2 position of the glycerol backbone. EPA-pPE has been reported to exhibit numerous distinctive bioactivities. However, the digestion, absorption, and metabolism characteristics of EPA-pPE in vivo are not clear, which restrict the molecular mechanism analysis related to its distinctive activities. The aim of the present study was to illustrate the digestion, absorption, and metabolism characteristics of EPA-pPE by lipid analysis in serum, intestinal wall, and content after oral administration of EPA-pPE emulsion. Results showed the EPA percentage of total fatty acids in serum was increasing over time, with two peaks at 5 and 10 h by 1.89 ± 0.2 and 2.58 ± 0.27, respectively, and then fell from 1.89 ± 0.17 at 10 h to 1.35 ± 0.16 at 16 h. In small intestinal content, EPA-pPE was hydrolyzed to lyso-phospholipids and EPA by phospholipases A2 and the vinyl ether bond was retained at the sn-1 position. The released EPA could be quickly taken up into the enterocytes and enter circulation. The comparison of simulated digestion in vitro showed that the distinct digestion and absorption process of EPA-pPE was a unique phenomenon. EPA could be retained in serum at a high level for a substantial period of time, which suggested that EPA-pPE was not just a short-lived circulating molecule.

3.
Biosci Biotechnol Biochem ; : 1-13, 2019 Oct 12.
Artigo em Inglês | MEDLINE | ID: mdl-31608790

RESUMO

Plasmenylethonoamine (pPE) and plasmanylcholine (aPC) are important phospholipid subclasses. Herein we explored optimum conditions for enzymatic purification and preparation of pPE and aPC from the mussel Mytilus edulis and bovine brain. Among them, pPE in Mytilus edulis PE was mainly p18:0-20:5 and p18:0-22:6, and its purity was 92.7%; aPC in PC was primarily a16:0-22:6 and a16:0-20:5, and aPC accounted for 90.2% of PC. We thereafter evaluated neurotrophic effects of Mytilus edulis pPE, aPC, and bovine brain pPE in a NGF-induced PC12 cell model. Morphologically, pPE and aPC could both promote differentiation, manifested in a significant increase in neurite length and number, due to increased expression of synaptophysin and growth protein GAP-43 in a dose-independent and structure-selective manner. Importantly, the effect on neuronal nutrition of pPE was better than aPC, and marine pPE was better than terrestrial pPE, which might be ascribed to vinyl-ether bond and differences in fatty acid composition. Abbreviations: AA: arachidonic acid; DHA: docosahexaenoic acid; EIC: extracted ion chromatogram; EPA: eicosapentanoic acid; GAP: growth-associated protein; HPLC: high-performance liquid chromatography; LC-MS/MS: liquid chromatography-tandem mass spectrometry; LPC: lyso-PC; LPE: lyso-PE; MS: mass spectrometry; NGF: nerve growth factor; PC: phosphatidylcholine; aPC: plasmanylcholine; PE: phosphatidylethanolamine; pPE: plasmenylethonoamine; PG: phosphoglycerols; PLs: phospholipids; PS: phosphoserines; TIC: total ion chromatogram.

4.
J Agric Food Chem ; 67(33): 9423-9431, 2019 Aug 21.
Artigo em Inglês | MEDLINE | ID: mdl-31329442

RESUMO

A high-throughput lipid analysis method was established to comprehensively investigate the lipid profiles of three marine (Scomberomorus niphonius, Scophthalmus maximus, and Oncorhynchus keta) and one freshwater (Ctenopharyngodon idellus) fish species using ultraperformance liquid chromatography coupled with quadrupole time-of-flight mass spectrometry. Over 700 molecular species from 12 major lipid subclasses were identified. Glycerolipids (73.7-85.6%) and phospholipids (PLs, 13.7-25.6%) were dominant components in total lipids. Polyunsaturated fatty acid PLs, such as phosphatidylethanolamine (PE, 16:0-22:6), PE (18:1-22:6), and phosphatidylcholine (16:0-22:6), were the major molecular species in PLs. The lipid composition of three marine fish (mainly C22:5) was significantly different from that in C. idellus (mainly C20:4 and C20:5). A unique long-chain base of sphingolipids was found in fish (mainly d19:3). These bioactive lipids were proposed to be potential biomarkers for distinguishing different fish species and evaluating nutritional values.


Assuntos
Lipídeos/química , Alimentos Marinhos/análise , Animais , Cromatografia Líquida de Alta Pressão , Cyprinidae , Ácidos Graxos Insaturados/química , Linguados , Espectrometria de Massas , Oncorhynchus keta , Fosfatidiletanolaminas/química , Fosfolipídeos/química , Atum
5.
Lipids ; 53(5): 517-526, 2018 May.
Artigo em Inglês | MEDLINE | ID: mdl-30071133

RESUMO

Phospholipase D (PLD) can react with phospholipids as substrates, generally phosphatidylcholine (PtdCho), and the PLD-substrate intermediate can be cleaved by another alcohol, resulting in transphosphatidylation of the substrate, which can be used in the production of special lipids. In this study, the reaction conditions affecting the transphosphatidylation of PtdCho with serine were optimized and the reaction specificity of a novel PLD prepared from Acinetobacter radioresistens a2 was evaluated for transphosphatidylation with a variety of phospholipid substrates and head group donors. Based on the yield of phosphatidylserine, experimental kinetic data, maximum transphosphatidylation rate, and kinetic constant, the specificity of PLD in transphosphatidylation was found to be affected by unsaturated fatty-acid phospholipid substrates. The catalytic efficiency of PLD prepared from A. radioresistens a2 on the synthesis of natural phospholipids is on the order of l-serine > ethanolamine and glycerol ≫ inositol. Moreover, it was found that the transphosphatidylation of PtdCho with saccharides was related to the length of the carbon chain and the number of saccharide units.

6.
J Sci Food Agric ; 98(14): 5257-5268, 2018 Nov.
Artigo em Inglês | MEDLINE | ID: mdl-29652437

RESUMO

BACKGROUND: Antarctic krill is a huge source of biomass and prospective high-quality lipid source. Eicosapentaenoic acid (EPA) and docosahexaenoic acid (DHA), nutritionally important lipid components with poor oxidative stability, were used as markers of oxidation during thermal processing of Antarctic krill (Euphausia superba) meal by evaluating the lipolysis, lipid oxidation, and non-enzymatic browning reactions. RESULT: Liquid chromatography-mass spectrometry of the phospholipids and the main oxidation products of free fatty acids and phosphatidylcholine (PC) was effective for evaluating the oxidation of EPA and DHA. During boiling, oxidation of EPA and DHA in the free fatty acid and PC fractions and hydrolysis of the fatty acids at the sn-2 position of the phospholipids were predominant. The changes in PC during drying were mainly attributed to the oxidation of EPA and DHA. Heat treatment increased the oxidation products and concentration of hydrophobic pyrrole owing to pyrrolization between phosphatidylethanolamine and the lipid oxidation products. CONCLUSION: The lipid oxidation level of Antarctic krill increased after drying, owing to prolonged heating under the severe conditions. © 2018 Society of Chemical Industry.


Assuntos
Euphausiacea/química , Manipulação de Alimentos/métodos , Lipídeos/química , Animais , Ácidos Graxos/química , Temperatura Alta , Reação de Maillard , Oxirredução , Fosfolipídeos/química
7.
Carbohydr Polym ; 190: 87-94, 2018 Jun 15.
Artigo em Inglês | MEDLINE | ID: mdl-29628263

RESUMO

A neutral water soluble polysaccharide (HPA) was isolated from the marine fungus Hansfordia sinuosae. Monosaccharide composition analysis indicated that HPA was mainly composed of mannose with minor amounts of galactose and glucose. The molecular weight of HPA was approximately 22.5 kDa as analyzed by HPGPC. Structure analysis of HPA with methylation and 1D, 2D NMR indicated that HPA was composed of [α-d-Manp(1→], [→2)-α-d-Manp(1→], [→3)-α-d-Manp(1→] and [→2,6)-α-d-Manp(1→] with [α-d-Manp(1→] linked to C-6 position of [→2,6)-α-d-Manp(1→]. The antitumor effect of HPA was evaluated in vitro. HPA showed remarkable inhibitory effect on human cervical carcinoma HeLa cells and human breast carcinoma MCF-7 cells. When cells were incubated with HPA at 400 µg/mL for 48 h, the inhibition rate on HeLa and MCF-7 cells was 79.5% and 73.8%, respectively. Furthermore, for HeLa cells, HPA could increase intracellular ROS levels, induce cells apoptosis, decrease mitochondrial membrane potential, and elevate the expression of caspase-3. The results suggested that HPA could be explored as a potential antitumor agent.


Assuntos
Antineoplásicos/química , Antineoplásicos/farmacologia , Ascomicetos/citologia , Espaço Extracelular/química , Polissacarídeos Fúngicos/química , Polissacarídeos Fúngicos/farmacologia , Apoptose/efeitos dos fármacos , Caspase 3/metabolismo , Proliferação de Células/efeitos dos fármacos , Regulação Neoplásica da Expressão Gênica/efeitos dos fármacos , Células HeLa , Humanos , Espaço Intracelular/efeitos dos fármacos , Espaço Intracelular/metabolismo , Células MCF-7 , Potencial da Membrana Mitocondrial/efeitos dos fármacos , Metilação/efeitos dos fármacos , Monossacarídeos/análise , Espécies Reativas de Oxigênio/metabolismo
8.
Food Funct ; 9(4): 2184-2192, 2018 Apr 25.
Artigo em Inglês | MEDLINE | ID: mdl-29541708

RESUMO

Abundant studies have highlighted the protective effects of docosahexaenoic acid (DHA), in the form of glycerolipids (glycerophosphatides and triglycerides) and DHA-ethyl esters (DHA-EE) in Alzheimer's disease (AD); however, eicosapentaenoic acid (EPA) has rarely been implicated. In the present study, we compared the effects of dietary EPA in the form of phosphatidylcholine (EPA-PC) and EE with DHA-EE (DHA/EPA = 60 mg kg-1 d-1, i.g., 20 days) on cognitive deficits in AD rats. EPA-PC, rather than EPA-EE, significantly improved Aß-induced cognitive impairment and has a comparable effect with DHA-EE. Further research indicated that EPA-PC and DHA-EE could significantly decrease lipid peroxidation levels, alleviate mitochondria-dependent apoptosis, and inhibit the hyperphosphorylation of tau mediated by GSK3ß. These findings suggest that EPA in the form of phosphatidylcholine rather than an ethyl ester has a comparable effect with DHA in improving cognitive impairment in Aß1-42-induced AD rats.


Assuntos
Doença de Alzheimer/prevenção & controle , Suplementos Nutricionais , Modelos Animais de Doenças , Ácido Eicosapentaenoico/uso terapêutico , Nootrópicos/uso terapêutico , Estresse Oxidativo , Fosfatidilcolinas/uso terapêutico , Alquilação , Doença de Alzheimer/metabolismo , Animais , Apoptose , Comportamento Animal , Córtex Cerebral/metabolismo , Ácidos Docosa-Hexaenoicos/análogos & derivados , Ácidos Docosa-Hexaenoicos/uso terapêutico , Ácido Eicosapentaenoico/análogos & derivados , Glicogênio Sintase Quinase 3 beta/metabolismo , Masculino , Aprendizagem em Labirinto , Neurônios/metabolismo , Fosforilação , Processamento de Proteína Pós-Traducional , Distribuição Aleatória , Ratos Sprague-Dawley , Proteínas tau/metabolismo
9.
Lipids ; 52(12): 1059-1060, 2017 12.
Artigo em Inglês | MEDLINE | ID: mdl-29134469

RESUMO

Erratum to: Lipids https://doi.org/10.1007/s11745-017-4305-7.

10.
Lipids ; 52(12): 1045-1058, 2017 Dec.
Artigo em Inglês | MEDLINE | ID: mdl-28975480

RESUMO

A fast and efficient shotgun lipidomics strategy was applied to analyze phospholipids (PL) in the oyster Crassostrea plicatula, including 29 species of phosphatidylcholine (PtdCho), 23 species of phosphatidylethanolamine (PtdEtn), 11 species of phosphatidylserine (PtdSer), 6 species of phosphatidylinositol (PtdIns), and 17 species of lysophospholipids (Lyso-PL). During storage at 4 °C for 7 days, the PL content decreased by 68.08%, but a significant increase in the FFA content was observed (from 63.11 to 318.72 µg/g). PtdCho and PtdIns decreased relatively by 64.97 and 67.49%, and PtdSer decreased most markedly by 74.15%. However, the PtdEtn content increased slightly during the early stages of storage but subsequently began to decrease. Moreover, PL with eicosapentaenoic acid (EPA-PL) and docosahexaenoic acid (DHA-PL) decreased by 51.77 and 50.61%, whereas plasmalogens were relatively stable showing only a 25.46% decrease. In particular, through enzyme activity analysis of lipase, phospholipase A1 (PLA1), phospholipase A2 (PLA2), phospholipase C (PLC), and phospholipase D (PLD), it was observed that the activities of all these enzymes increased at the early stage at 4 °C, but their activities were at lower levels when the oysters were stored at -20 °C. During the storage period at 4 °C, correlation analysis suggests that the degradation of PtdCho was mostly correlated to PLA2 (p < 0.05), whereas PtdEtn and PtdSer were more markedly correlated to lipase and PLD, respectively. The above result indicates that the hydrolysis mechanism of PL during seafood storage was correlated to the lipid hydrolytic enzyme activities under different storage temperatures.


Assuntos
Crassostrea/fisiologia , Fosfolipídeos/análise , Animais , Crassostrea/metabolismo , Hidrólise , Lisofosfolipídeos/análise , Lisofosfolipídeos/química , Fosfatidiletanolaminas/análise , Fosfatidiletanolaminas/química , Fosfatidilinositóis/análise , Fosfatidilinositóis/química , Fosfatidilserinas/análise , Fosfatidilserinas/química , Fosfolipídeos/química
11.
J Food Sci ; 82(8): 1961-1967, 2017 Aug.
Artigo em Inglês | MEDLINE | ID: mdl-28732111

RESUMO

Sea cucumber saponins (SCSs) exhibit a wide spectrum of bioactivities, but their metabolic characteristics are not well elucidated. In this study, the metabolism of holothurin A (HA) and echinoside A (EA), 2 major saponins in sea cucumber, by gut microflora were investigated. First, we conducted an in vitro study, where in the SCSs were incubated with intestinal microflora and the metabolites were detected by high pressure liquid chromatography-high resolution mass spectrometry. We also conducted an in vivo study on rats, where in the intestinal contents, serum, urine, and feces were collected and evaluated after oral administration of SCSs. In the in vitro study, we identified 6 deglycosylated metabolites of HA and EA, assigned M1-M6. In the in vivo study, we found all the deglycosylated metabolites in the intestinal contents after oral administration, and both the metabolites and their prototype components could be absorbed. Four metabolites were identified in the serum, 6 in the urine, and 4 in the feces. The saponins with different structures showed different absorption characteristics in rats. According to our results, deglycosylation is the main intestinal microflora-mediated metabolic pathway for SCSs, and both the SCSs and deglycosylated metabolites can be absorbed by intestine. This study improves the understanding of the metabolism of HA and EA by gut flora, which will be useful for further analysis of the bioactivity mechanism of SCSs.


Assuntos
Holoturina/análogos & derivados , Pepinos-do-Mar/metabolismo , Animais , Cromatografia Líquida de Alta Pressão/métodos , Fezes/química , Microbioma Gastrointestinal , Holoturina/química , Holoturina/metabolismo , Mucosa Intestinal/metabolismo , Intestinos/microbiologia , Masculino , Espectrometria de Massas/métodos , Redes e Vias Metabólicas , Ratos , Saponinas/análise , Pepinos-do-Mar/química
12.
J Med Food ; 20(4): 392-402, 2017 Apr.
Artigo em Inglês | MEDLINE | ID: mdl-28406733

RESUMO

Alzheimer's disease (AD) is a neurodegenerative disorder. Emerging evidence implicates ß-amyloid (Aß) plays a critical role in the progression of AD. In this study, we investigated the protective effect of cerebrosides obtained from sea cucumber against senescence-accelerated mouse prone 8 (SAMP8) mice in vivo. We also studied the effect of cerebrosides on Aß-induced cytotoxicity on the rat pheochromocytoma cell (PC12) and the underlying molecular mechanisms. Cerebrosides ameliorated learning and memory deficits and the Aß accumulation in demented mice, decreased the content of malondialdehyde (MDA), 8-oxo-7,8-dihydro-2'-deoxyguanosine (8-OHdG), 8-hydroxy-2'-deoxyguanosine (8-oxo-G), and nitric oxide (NO), and enhanced the superoxide dismutase (SOD) activity significantly. The neuroprotective effect of sea cucumber cerebrosides (SCC) was also verified in vitro: the cerebrosides increased the survival rate of PC12 cells, recovered the cellular morphology, downregulated the protein levels of Caspase-9, cleaved Caspase-3, total Caspase-3, and Bax, and upregulated the protein level of Bcl-2, revealing that cerebrosides could inhibit Aß-induced cell apoptosis. The results showed the protective effect of SCC was regulated by the mitochondria-dependent apoptotic pathway. Our results provide a new approach to developing the marine organisms as functional foods for neuroprotection.


Assuntos
Cerebrosídeos/farmacologia , Fármacos Neuroprotetores/farmacologia , Estresse Oxidativo/efeitos dos fármacos , Pepinos-do-Mar/química , Doença de Alzheimer , Peptídeos beta-Amiloides/química , Animais , Apoptose , Sobrevivência Celular , Guanosina/química , Hipocampo/química , Aprendizagem , Masculino , Malondialdeído/química , Transtornos da Memória , Camundongos , Camundongos Endogâmicos , Óxido Nítrico/química , Células PC12 , Ratos , Superóxido Dismutase/metabolismo
13.
Food Funct ; 8(3): 1271-1281, 2017 Mar 22.
Artigo em Inglês | MEDLINE | ID: mdl-28232989

RESUMO

Herein, we investigated the potential relationship between sphingolipids and Alzheimer's disease (AD) with special attention to the relationship between dietary sea cucumber glucocerebrosides (SCGs) and sphingolipid metabolism. We assessed animal behavior using the Morris water maze test, determined Aß1-42 concentration in the hippocampus using ELISA, and assessed the sphingolipid profile of the hippocampus and the cortex in normal mice (SAMR1), AD mice (SAMP8), and AD mice (SAMP8) fed with SCG using liquid chromatography-triple quadrupole mass spectrometry. We found that the SAMP8 mice had impaired memory and an SCG diet significantly rescued spatial memory deficits in these mice. As expected, we found that the profiles of sphingolipid species and the levels of total cerebrosides (CBS), ceramides (Cer), and sulfatides (ST) were significantly different in both the hippocampus and the cortex between the three groups; moreover, there were significantly lower ST levels and higher Cer and CBS levels in these regions in the SAMP8 mice. In the AD-SCG group, Cer and ST levels were altered only in the hippocampus, in contrast to the AD group. The major molecular species ST (d18:1-C24:1) and Cer (d18:1/18:0) were especially different between those of the two groups. Unexpectedly, sphingolipid profiles, including the nonhydroxylated fatty acid-ST/hydroxylated fatty acid-ST, very long fatty acid-galactocerebroside/long fatty acid-galactocerebroside, nonhydroxylated fatty acid-galactocerebroside/hydroxylated fatty acid-galactocerebroside and galactocerebroside/glucocerebroside ratios, were affected by AD. Thus, the ST and Cer levels and the profiles of sphingolipid species in the AD-SCG group were significantly different compared to those of the AD model group. Therefore, SCG has potential ameliorative effects in AD, and exogenous sphingolipid intake may potentially influence sphingolipid metabolism in vivo.


Assuntos
Doença de Alzheimer/metabolismo , Córtex Cerebral/metabolismo , Glucosilceramidas/farmacologia , Hipocampo/metabolismo , Pepinos-do-Mar/química , Esfingolipídeos/metabolismo , Doença de Alzheimer/tratamento farmacológico , Doença de Alzheimer/psicologia , Animais , Córtex Cerebral/química , Córtex Cerebral/efeitos dos fármacos , Suplementos Nutricionais/análise , Modelos Animais de Doenças , Hipocampo/química , Hipocampo/efeitos dos fármacos , Humanos , Masculino , Aprendizagem em Labirinto , Camundongos , Camundongos Transgênicos
14.
Lipids ; 51(3): 321-34, 2016 Mar.
Artigo em Inglês | MEDLINE | ID: mdl-26861868

RESUMO

To investigate the relationship between structure and activity, three glucocerebroside series (CFC-1, CFC-2 and CFC-3), ceramides (CF-Cer) and long-chain bases (CF-LCB) of sea cucumber Cucumaria frondosa (C. frondosa) were isolated and evaluated in HepG2 cells. The molecular species of CFC-1, CFC-2 and CFC-3 and CF-Cer were identified using reversed-phase liquid chromatography with heated electrospray ionization coupled to high-resolution mass spectrometry (RPLC-HESI-HRMS), and determined on the basis of chemical and spectroscopic evidence: For the three glucocerebroside series, fatty acids (FA) were mainly saturated (18:0 and 22:0), monounsaturated (22:1, 23:1 and 24:1) and 2-hydroxyl FA (2-HFA) (23:1 h and 24:1 h), the structure of long-chain bases (LCB) were dihydroxy (d17:1, d18:1 and d18:2) and trihydroxy (t16:0 and t17:0), and the glycosylation was glucose; For CF-Cer, FA were primarily saturated (17:0) and monounsaturated (16:1 and 19:1), the structure of LCB were dihydroxy (d17:1 and d18:1), and trihydroxy (t16:0). The results of cell experiment indicated that all of three glucocerebroside series, CF-Cer and CF-LCB exhibited an inhibitory effects on cell proliferation. Moreover, CFC-3 was most effective in three glucocerebrosides to HepG-2 cell viability. The inhibition effect of CF-LCB was the strongest, and the inhibition effect of CF-Cer was much stronger than glucocerebrosides.


Assuntos
Cucumaria/química , Neoplasias/patologia , Esfingolipídeos/química , Esfingolipídeos/farmacologia , Animais , Antineoplásicos/química , Antineoplásicos/isolamento & purificação , Antineoplásicos/farmacologia , Proliferação de Células/efeitos dos fármacos , Sobrevivência Celular/efeitos dos fármacos , Relação Dose-Resposta a Droga , Células Hep G2 , Humanos , Estrutura Molecular , Neoplasias/tratamento farmacológico , Esfingolipídeos/isolamento & purificação , Esfingolipídeos/toxicidade , Relação Estrutura-Atividade
15.
Lipids ; 50(7): 667-79, 2015 Jul.
Artigo em Inglês | MEDLINE | ID: mdl-26037520

RESUMO

Usually, the chemical structures of cerebrosides in sea creatures are more complicated than those from terrestrial plants and animals. Very little is known about the method for high-throughput molecular profiling of cerebrosides in sea cucumbers. In this study, cerebrosides from four species of edible sea cucumbers, specifically, Apostichopus japonicas, Thelenota ananas, Acaudina molpadioides and Bohadschia marmorata, were rapidly identified using reversed-phase liquid chromatography-quadrupole-time-of-flight mass spectrometry (RPLC-QToF-MS). [M + H](+) in positive electrospray ionization (ESI) mode were used to obtain the product ion spectra. The cerebroside molecules were selected according to the neutral loss fragments of 180 Da and then identified according to pairs of specific products of long-chain bases (LCB) and their precursor ions. A typical predominant LCB was 2-amino-1,3-dihydroxy-4-heptadecene (d17:1), which was acylated to form saturated and monounsaturated non-hydroxy and monohydroxy fatty acids with 17-25 carbon atoms. Simultaneously, the occurrence of 2-hydroxy-tricosenoic acid (C23:1h) was characteristic of sea cucumber cerebrosides, whereas this molecule was rarely discovered in plants, mammals, or fungi. The profiles of LCB and fatty acids (FA) distribution might be related to the genera of sea cucumber. These data will be useful for identification of cerebrosides using RPLC-QToF-MS.


Assuntos
Cerebrosídeos/química , Cerebrosídeos/isolamento & purificação , Cromatografia Líquida/métodos , Espectrometria de Massas/métodos , Pepinos-do-Mar/química , Animais , Ensaios de Triagem em Larga Escala/métodos , Pepinos-do-Mar/classificação
16.
J Oleo Sci ; 64(1): 51-60, 2015.
Artigo em Inglês | MEDLINE | ID: mdl-25492230

RESUMO

Liquid chromatography-mass spectrometry was one of the most powerful methods for identification and detection of chemical structures of lipids. In this study, the cerebrosides molecular species from the sea cucumber Pearsonothria graeffei (P. graeffei) were high throughput identified by liquid chromatography-quadrupole-time-of-flight mass spectrometry (LC-Q-TOF-MS). Cerebrosides were separated and purified by solid-phase extraction with chloroform-methanol solution. Precursor ion scan spectra and product ion scan spectra were obtained through auto MS/MS analysis in the positive scan. Cerebroside molecules were selected according to the neutral loss fragments of 180 Da, and then the structures were identified according to pairs of specific products of sphingoid bases and their precursor ions. Eighty-nine cerebrosides molecular species were identified, large amounts of d17:1-C22:0 h, t17:0-C24:1h, d17:1-C24:1h, d17:1-C23:0 h, d17:1-C22:0 and d17:1-C23:0 were present which have hardly found in mammal. There were 13 classes of long-chain base (LCB), and the ratio of phytosphingosines and sphingosines was roughly 1:9, in which two of the most common LCBs were d17:1 and d18:1. The carbon numbers of fatty acids (FAs) were mainly 18~24, while 24 carbon fatty acids were predominant. The ratio of saturated fatty acid (SFA) and monounsaturated fatty acid (MUFA) was about 2:3, and the percentage of hydroxy fatty acid (HFA) was over 60%. The ratio of non-hydroxylated fatty acid (NFA)/HFA was also approximately 2:3. LC-Q-TOF-MS analysis should be useful for the structure determination of diverse cerebrosides molecular species. Meanwhile, this method provided a basis for structure-activity relationship studies and functional food development of the sea cucumber P. graeffei as well.


Assuntos
Cerebrosídeos/análise , Cerebrosídeos/química , Cromatografia Líquida/métodos , Ensaios de Triagem em Larga Escala/métodos , Espectrometria de Massas/métodos , Pepinos-do-Mar/química , Animais , Cerebrosídeos/isolamento & purificação , Extração em Fase Sólida/métodos , Espectrometria de Massas em Tandem
17.
Food Chem ; 166: 473-8, 2015 Jan 01.
Artigo em Inglês | MEDLINE | ID: mdl-25053082

RESUMO

Sea urchin gangliosides have been proved to contain neuritogenic activities, which related to their molecular compositions. This study reports a method utilizing reversed-phase chromatography coupled to mass spectrometry for structure investigation and molecular species determination of the monosialogangliosides from sea urchin Strongylocentrotus nudus. Two types of sulfated and nonsulfated monosialogangliosides were isolated from the sea urchin ovary. In MS(2) spectra of both nonsulfated monosialoganglioside and sulfated monosialoganglioside, 2-6 linked sialic acids were identified by the characteristic fragments of (0,4)A2-CO2 and (0,2)A1. Fragment ions at m/z 139.1 and m/z 169.1 of nonsulfated monosialoganglioside might be characteristic for 8-sulfated sialic acid residue. Retention time of the molecules was effectively used in the characterization of unknown molecules, and molecules that differ in mass by only 0.04 Da were easily differentiated.


Assuntos
Cromatografia de Fase Reversa/métodos , Gangliosídeos/análise , Ouriços-do-Mar/química , Animais , Feminino , Ácido N-Acetilneuramínico/análise , Espectrometria de Massas por Ionização por Electrospray , Espectrometria de Massas em Tandem
18.
Se Pu ; 32(1): 26-33, 2014 Jan.
Artigo em Chinês | MEDLINE | ID: mdl-24783865

RESUMO

Cerebrosides from sea cucumber Parastichopus californicus were identified by using liquid chromatography-quadrupole-time-of-flight mass spectrometry (LC-Q-TOF MS/ MS). The samples were extracted with chloroform-methanol (2: 1, v/v) solution and purified by a SPE cartridge. In positive ion mode electrospray ionization (ESI), the precursor ion scan mass spectra and product ion scan mass spectra were obtained through the automatic MS/MS mode. Cerebroside molecules were selected according to the neutral loss fragments of 180 Da, and then were identified according to long-chain base (LCB) fragments and fatty acid (FA) fragments. One hundred and twenty-three cerebroside molecular species were identified. There are 18 species of LCB, and the relative content ratio of phytosphingosines and sphingosines is 1: 2. The carbon numbers of fatty acids are mainly 18 - 25, of which 24 carbon fatty acids are predominant. The relative content ratio of saturated fatty acids and monounsaturated fatty acid is about 1: 3, and the presence of 2-hydroxy fatty acids is about 58.62%. LC-Q-TOF MS/MS method is sensitive, accurate and simple. At the same time, this study provided a theoretical basis for structure-activity relationship studies and functional food development of Parastichopus californicus as well.


Assuntos
Cerebrosídeos/análise , Pepinos-do-Mar/química , Espectrometria de Massas em Tandem , Animais , Cromatografia Líquida
19.
Se Pu ; 31(5): 399-403, 2013 May.
Artigo em Chinês | MEDLINE | ID: mdl-24010336

RESUMO

An approach based on liquid chromatography-tandem mass spectrometry was developed for the quantification of monosialogangliosides (MG) in sea cucumbers and sea urchins. The gangliosides of sea cucumbers and sea urchins were extracted according to the Svennerholm method and cleaned up by C8 solid phase extraction column. The extracts were separated on an APS-2 NH2 column (150 mm x 2.1 mm, 3 microm) with the mobile phases of acetonitrile and 50 mmol/L ammonium acetate (pH 5.6) under gradient elution. Multiple reaction monitoring (MRM) was performed for quantification of each analyte in the samples. The method was capable to distinguish gangliosides with different types of sialic acid in a single run. The limit of quantification was 0.22 ng for nonsulfated monosialoganglioside (NMG) and 0.29 ng for sulfated monosialoganglioside (SMG), and the linear range was 1-40 ng for both compounds. Only NMG was detected in sea cucumbers while both NMG and SMG were detected in sea urchins. Quantification results suggested that NMG was most abundant in Parastichopus californicus among all the sea cucumbers detected and SMG was most abundant in Anthocidaris crassispina among all the sea urchins. The contents of MGs in sea urchins (4.30 - 6.40 mg/g) were much higher than those in sea cucumbers (8 -131 microg/g). The method is suitable for the quantification of monosialogangliosides in sea urchins and sea cucumbers.


Assuntos
Gangliosídeos/análise , Pepinos-do-Mar/química , Ouriços-do-Mar/química , Animais , Cromatografia Líquida de Alta Pressão , Extração em Fase Sólida , Espectrometria de Massas em Tandem
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