Orientador: Cesar Costapinto Santana / Dissertação (mestrado) - Universidade Estadual de Campinas, Faculdade de Engenharia Química / Made available in DSpace on 2018-08-20T14:12:19Z (GMT). No. of bitstreams: 1 Nascimento_AnaCarolina_M.pdf: 2361694 bytes, checksum: bcd5c25d65fe1d7ac8a8666d6f13c023 (MD5) Previous issue date: 2012 / Resumo: O secnidazol corresponde à formulação 1-(hidroxipropil)-2-metil-5-nitroimidazol e possui espectro de atividade contra microorganismos anaeróbicos e eficácia no tratamento de amebíase, giardíase, tricomoníase e vaginose bacteriana. Ele é comercializado na forma racêmica, isto é, na proporção 1:1 dos seus enantiômeros R e S. Não é oficial em nenhuma farmacopeia. Estudos relatam que para alguns imidazóis o enantiômero R apresenta maior atividade biológica frente ao enantiômero S. Portanto a separação do secnidazol é importante para testes biológicos comparativos de efeitos colaterais. Inserindo-se neste contexto, foi desenvolvido este trabalho de pesquisa com o intuito de estudar a resolução enantiomérica do fármaco secnidazol pela técnica de cromatografia líquida de alta eficiência utilizando coluna recheada com fase estacionária tris(3,5-dimetilfenilcarbamato) de amilose. Experimentos de pulsos com soluções diluídas foram realizados variando a vazão de fase móvel de 1,0 a 2,5 mL/min e as temperaturas de 20 a 35°C. Os resultados mostraram alta eficiência, com número de pratos superando 1000 e fatores de separação na ordem de 7,0. Os valores negativos de 'delta'H e 'delta'S* indicam que a adsorção dos enantiômeros da fase móvel na fase estacionária é entalpicamente favorável. Experimentos a altas concentrações (condições de sobrecarga) foram realizados com a finalidade de determinar as isotermas não-lineares pelo método da análise frontal e também os perfis de eluição sob estas condições. As isotermas de adsorção apresentaram comportamento não-linear e o modelo de Langmuir foi bem correlacionado aos dados experimentais de equilíbrio no intervalo de concentração analisado. A partir da metodologia shortcut foram obtidos os parâmetros operacionais da unidade leito móvel simulado. As purezas alcançadas para as correntes de extrato e refinado foram 85,50% e 72,50%, respectivamente / Abstract: The chemical formula of secnidazole is 1-(hydroxypropyl)-2-methyl-5-nitroimidazole. It acts activity against anaerobic microorganisms and is effective in the treatment of amebiasis, giardiasis, trichomoniasis, and bacterial vaginosis. It is marketed in the racemic form, that is, proportion 1:1 of their R and S-enantiomers. It's not officially recognized by any pharmacopoeia. Studies have reported that for some imidazoles the R-enantiomer has a higher biological activity than the S-enantiomer. For this reason the separation of secnidazole is important for comparative biological tests of side effects. It is in this context that this research was developed in order to study the enantiomeric resolution of drug secnidazole by the technique of high performance liquid chromatography using stationary phase column packed with amylose tris (3, 5- dimethylphenylcarbamate). Pulse experiments with dilute solutions were conducted by varying the mobile phase flow (1.0 to 2.5 mL/min) and temperature (20 to 35 °C). The results revealed high efficiency, with number of plates overcoming 1000 and selectivities in the order of 7.0. The negative values of 'delta'H and 'delta'S* indicates that the enantiomer adsorption from the mobile phase to stationary phase is enthalpically favorable. Experiments in overloaded conditions were realized to obtain the equilibrium adsorption isotherms by frontal analysis, as well overload elution profiles. The adsorption isotherms shown a nonlinear behavior and the Langmuir model was well correlated to equilibrium experimental data in the range of investigated concentration. From the shortcut method operating parameters were obtained to the simulated moving bed unit. The purities reached for the extract and raffinate lines were 85.50% and 72.50% , respectively / Mestrado / Desenvolvimento de Processos Biotecnologicos / Mestra em Engenharia Química

Introduction: Despite the tremendous advances made with regard to synthetic organic medicinals within the last two decades, heavy reliance is still placed on plant products. This is especially true of the anthracene derivatives used medicinally as purgatives, and which are derived principally from senna, cascara, rhubarb, frangula and aloes. While particular attention has been paid to the chemistry of the former group in recent years, aloes has been largely neglected, possibly due to the fact that the Aloe species are confined largely to areas where extensive research facilities are lacking, such as Africa , India and the West Indies. Thus research in Europe has been confined largely to the lump aloes of commerce, derived from relatively few species. In 1953 a comprehensive report by Hodge (103) appeared on "The Drug Aloes of Commerce, with Special Reference to the Cape Species". Hodge observed that South Africa abounds in species just as abundant as A.ferox, (which is the prime source of Cape aloes), and advised that a systematic chemical survey might show certain of these to be not only higher yielders of bitter aloetic juice but also sources of a superior drug product. Consequently an investigation along these lines is presented here, and it is observed that several species apart from A.ferox not only contain aloin, but also yield a large volume of aloetic juice. Only pharmacologic studies can reveal if the juice of these species is as safe as that of A.ferox, but without doubt they could be used for the extraction of crystalline aloin. Concurrently, the distribution of the Aloe resins, said by some to be purgative themselves, has been studied. The investigation has revealed that the structurally similar compound homonataloin enjoys an equally wide distribution as aloin. However, almost invariably it is confined to small species yielding little aloetic juice, apart from which nothing is known regarding its pharmacologic properties. It is interesting to note that the resin distribution in the homonataloin-containing species is very similar to that of the aloin-containing species, but differs widely from. that of the species containing neither of these principles. Apart from aloin and homonataloin, aloinoside and chrysophanol also occur in Aloe species, and together with the resins, these indicate that when all the South African Aloe species have been investigated, they may well be of chemotaxonomic value. Within the comparatively short space of the last decade some work has been performed on aspects of the metabolism of such anthracene-containing species as Rheum, Rhamnus and Rumex. These investigations have shown that the anthracene derivatives are not merely waste products, but perform definite metabolic functions. The latter portion of this work has been devoted to this relatively neglected aspect of the Aloe species.

“Lab on a Chip” technologies have revolutionized the field of bio-chemical analytics. The crucial role of optical techniques in this revolution resulted in the emergence of a field by itself, which is popularly termed as “optofluidics”. The miniaturization and integration of the optical parts in the majority of optofluidic devices however still remains a technical challenge. The works described in this thesis focuses on developing integration methods to combine various optical techniques with microfluidics in an alignment-free geometry, which could lead to the development of portable analytical devices, suitable for field applications. The integration approach was applied to implement an alignment-free optofluidic chip for optical chromatography; a passive optical fractionation technique fractionation for cells or colloids. This system was realized by embedding large mode area photonic crystal fiber into a microfluidic chip to achieve on-chip laser beam delivery. Another study on passive sorting envisages an optofluidic device for passive sorting of cells using an optical potential energy landscape, generated using an acousto-optic deflector based optical trapping system. On the analytical side, an optofluidic chip with fiber based microfluidic Raman spectroscopy was realized for bio-chemical analysis. A completely alignment-free optofluidic device was realized for rapid bio-chemical analysis in the first generation by embedding a novel split Raman probe into a microfluidic chip. The second generation development of this approach enabled further miniaturization into true microfluidic dimensions through a technique, termed Waveguide Confined Raman Spectroscopy (WCRS). The abilities of WCRS for online process monitoring in a microreactor and for probing microdroplets were explored. Further enhanced detection sensitivity of WCRS with the implementation of wavelength modulation based fluorescent suppression technique was demonstrated. WCRS based microfluidic devices can be an optofluidic analogue to fiber Raman probes when it comes to bio-chemical analysis. This allows faster chemical analysis with reduced required sample volume, without any special sample preparation stage which was demonstrated by analyzing and classifying various brands of Scotch whiskies using this device. The results from this study also show that, along with Raman spectroscopic information, WCRS picks up the fluorescence information as well, which might enhance the classification efficiency. A novel microfabrication method for fabricating polymer microlensed fibers is also discussed. The microlensed fiber, fabricated with this technique, was combined with a microfluidic gene delivery system to achieve an integrated system for optical transfection with localized gene delivery.

En esta Tesis Doctoral se aplica la cromatografía de gases con detector olfatométrico (la nariz humana) en el análisis de los compuestos volátiles aromáticos de distintos alimentos: el vinagre de vino con Denominación de Origen Protegida “Vinagre de Jerez”, los pistachos tostados y el aceite de oliva. Los distintos métodos de preparación de muestra (la microextracción en fase sólida sobre el espacio de cabeza, o HS-SPME, y la extracción directa con disolvente, o DSE) han proporcionado extractos representativos del aroma de estos productos, y gracias a la técnica olfatométrica empleada (Aroma Extract Dilution Analysis o AEDA) se han identificado los odorantes más potentes. Así se ha logrado caracterizar el aroma de dichos alimentos, recogiéndose los resultados de las investigaciones realizadas en distintos artículos publicados en varias revistas internacionales. / In this Doctoral Thesis, the gas chromatography with olfactometry detector (the human nose) has been applied to analyse the volatile aromatic compounds from different foodstuffs: the wine vinegar produced under Protective Denomination of Origen “Vinagre de Jerez”, the roasted pistachios and the olive oil. The different sample pre-treatment methods employed (the headspace solid-phase microextraction, or HS-SPME, and the direct solvent extraction, or DSE) have provided representative aroma extracts from these products. Furthermore, and thanks to the olfactometric technique used (the Aroma Extract Dilution Analysis or AEDA), the most potent odorants have been identified. Thus, the aroma of all these foodstuffs has been characterized. All the results obtained from the research developed have been published in different international journals.

Among the numerous beneficial effects of phospholipides can highlight their role in protecting the cardiovascular system and improving memory and learning. These effects can be partially explained by the fact that phospholipids are rich in polyunsaturated (eicosapentaenoic and docosahexaenoic acids) or essential fatty acids. Thus, it is very significant to explore potential food sources containing polyunsaturated rich phospholipids for the development new food products supplemented with phospholipids.This work allowed a series method for the extraction, purification, separation and quantification of phospholipids in order to characterize the polyunsaturated phospholipid sources. Food supplementation with polyunsaturated phospholipids rises however the question of their stability during food processing at high temperature. Then we have developed methods to identify phospholipids degradation products and determine their kinetics of the oxidation during thermal treatment which is a widespread food processing.Phospholipids (PE and PC) are more stable than triacylglyceride, this is due to the presence of an amino group in the molecule.

Coordenação de Aperfeiçoamento de Pessoal de Nível Superior (CAPES) / Uma grande variedade de produtos que estão presentes no cotidiano da população é continuamente lançada nos ecossistemas aquáticos. Esses produtos contêm compostos de diferentes classes, como fármacos, hormônios, produtos de cuidados pessoais, entre outros. O crescente interesse por essas substâncias ocorre principalmente porque elas podem exibir atividade biológica em concentrações muito baixas, da ordem de µg L-1 e ng L-1 . Portanto, neste trabalho, foi avaliada a presença e determinada a concentração de 20 microcontaminantes, pertencentes a diferentes classes (antiinflamatórios, reguladores lipídicos, antimicrobianos, antissépticos, hormônios sexuais e cafeína), no rio Palmital, localizado na Região Metropolitana de Curitiba. Para investigar a presença desses poluentes, foi realizado o monitoramento ao longo de quatro coletas, em sete pontos de amostragem no rio Palmital. As amostras coletadas foram submetidas ao processo de extração em fase sólida e posteriormente os compostos foram determinados utilizando cromatografia em fase líquida com detector de arranjo de diodos e cromatografia em fase gasosa hifenada a espectrometria de massas. A validação da metodologia utilizada baseou-se nos padrões estabelecidos pela Agência Nacional de Vigilância Sanitária e pelo Instituto Nacional de Metrologia. O método de extração e quantificação foi eficiente para a determinação desses analitos em amostras de água. Dentre os contaminantes analisados, a Cafeína foi detectada em quase 100% das amostras e teve a concentração mais elevada (3,58 µg L-1 ). Entre os produtos farmacêuticos investigados, o cetoprofeno esteve presente em 27 das 28 amostras analisadas, porém em concentrações mais baixas (concentração máxima de 0,18 µg L-1 ) que os demais fármacos; o ácido acetilsalicílico teve a maior concentração (2,31 µg L-1 ) seguida do paracetamol (1,28 µg L-1 ). Concentrações significativas de hormônios também foram quantificadas no rio Palmital, assim como os parabenos e triclosan indicando uma possível influência antrópica no ambiente aquático estudado. Observou-se que ocorreram mudanças associadas a variações sazonais, sendo que em período de estiagem (outubro/2016 e julho/2017), as concentrações foram mais elevadas para a maioria dos contaminantes analisados no rio Palmital. Com o tratamento estatístico dos dados foi possível verificar uma relação entre os contaminantes emergentes estudados em conjunto com as concentrações de Namoniacal e ortofosfato. Os resultados indicaram que o rio Palmital apresentou grande influência antrópica, possivelmente aporte de efluentes domésticos provenientes de áreas densamente povoadas, as quais possuem um serviço de coleta e tratamento de esgoto que não atende a todos os domicílios. / A wide variety of products present in the daily life of the population is released into aquatic ecosystems. These products contain compounds of different classes, such as pharmaceuticals, hormones, personal care products, among others. The growing interest in these substances occurs mainly because they may exhibit biological activity at very low concentrations of the order of μg L-1 and ng L-1 . Thus, it was evaluated in the presence and concentration of 20 microcontaminants belonging to different classes (anti-inflammatories, lipid regulators, antimicrobials, antiseptics, sex hormones and caffeine) in the Palmital River, located in the Metropolitan Region of Curitiba. In order to investigate the presence these pollutants, monitoring was carried out over four samplings at seven points on the Palmital River. The collected samples were submitted to extraction in solid phase and analyzed by liquid phase chromatography with diode array detector and gas chromatography tandem mass spectrometry. The validation of the methodology used was based on the standards established by the Agência Nacional de Vigilância Sanitária and the Instituto Nacional de Metrologia. The extraction and quantification method were efficient for the determination of these analytes in water samples. Among the contaminants analyzed, Caffeine was detected in almost 100% of the samples and had the highest concentration (3.58 μg L-1 ). Among the investigated pharmaceutical products, ketoprofen was present in 27 of the 28 analyzed samples, but in lower concentrations (maximum concentration of 0.18 μg L-1 ) than the other drugs; acetylsalicylic acid had the highest concentration (2.31 μg L-1 ) followed by paracetamol (1.28 μg L-1 ). Significant concentrations of hormones were also quantified in the Palmital river, as well as the parabens and triclosan indicating a possible anthropic influence in the aquatic environment studied. It was observed that changes were associated with seasonal variations, and in the drought period (October / 2016 and July / 2017) the concentrations were higher for most of the contaminants analyzed in the Palmital River. With the statistical treatment of the data it was possible to verify the relation between the emerging contaminants studied together with the concentrations of Nammonia and Orthophosphate. The results indicated that the Palmital River presents a great anthropic influence, possibly due to the contribution of domestic effluents from densely populated areas, which have a sewage collection and treatment service that does not serve all households.

An environmentally friendly, rapid and cost effective analytical procedure based on dispersive liquid-liquid microextraction was developed for the determination of six tetracyclines (TCs) in meat destined for human consumption. Meat extracts were analyzed for TCs using a sensitive and selective analytical technique, liquid chromatography tandem mass spectrometry. Various influencing factors on the extraction, separation and determination of TCs such as pH of mobile phases, type and volume of disperser solvent, type and volume of extraction solvent and sample pH were optimized. Validation parameters such as calibration function, limit of detection (LOD), limit of quantification (LOQ), detection capability (CCα), decision limit (CCβ), accuracy and precision were established according to EU commission decision 2002/657/EC. Linearity in the range of 25-200 μg kg-1 was obtained with regression coefficients ranging from 0.9991 to 0.9998. Recoveries of spiked blank muscle samples at three levels (i.e. 50, 100 and 150 μg kg-1) ranged from 80 to 101% and reproducibility was between 2 and 7%. The LODs and LOQs ranged from 2.22 to 3.59 μg kg-1 and from 7.38 to 11.49 μg kg-1 respectively. The CCα ranged from 105 to 111 μg kg-1 while CCβ ranged from 107 to 122 μg kg-1. The proposed method compared well with the dispersive solid phase extraction method and was successfully applied to the determination of TCs in meat samples. Some of the thirty bovine muscle samples obtained from local abattoirs and butcheries were found to contain two tetracycline antibiotics residues (chlortetracycline and oxytetracycline) with oxytetracycline being the most commonly detected. The concentration levels of the TC residues detected in the eleven bovine muscle samples were between 12.4 and 68.9 μg kg-1, levels that are lower than the European Union set maximum residue level (MRL) of 100 μg kg-1 hence the meat was fit for human consumption. / Chemistry / M. Sc. (Chemistry)

Rotavirus is responsible for the death of many children annually, and current vaccines have lower efficiency in developing countries. A reverse translated consensus gene sequence of the rotavirus VP6 cloned into a pET-28a(+) plasmid was used to transform BL21 and KRX Escherichia coli cells. Optimal expression of soluble protein was induced in KRX cells by adding 0.05% L-rhamnose and 0.0001 M IPTG, with an incubation temperature of 25ºC for 6 h. VP6 was purified by combining anion exchange chromatography followed by affinity chromatography. Far-UV circular dichroism and intrinsic fluorescence were used as probes to assess the native structure of VP6 and structural in the presence of a denaturant, high sodium chloride concentrations and varying temperatures. The 0.2 M sodium chloride had an impact on the VP6’s tertiary structure and also influenced the proteins conformational changes as detected during thermal unfolding to 90ºC. Although treatment with 3 M urea showed tertiary structural changes no secondary structural loss occurred due to the presence of a denaturant. / Life Sciences / M. Sc. (Life Sciences)

Cleome dendroides é uma espécie endêmica da Mata Atlântica dos estados do Rio de Janeiro e Espírito Santo, bioma alterado por intensa atividade antrópica, o que constitui uma ameaça à preservação de suas populações. Não existem estudos dos pontos de vista fisiológico, biotecnológico, fitoquímico ou farmacológico sobre a espécie. Considerando-se o perfil fitoquímico e o potencial medicinal do gênero, torna-se relevante definirem-se protocolos para a produção de plantas e metabólitos de C. dendroides utilizando diferentes sistemas de cultivo in vitro. No presente trabalho, foram realizados estudos sobre a germinação in vivo da espécie, avaliando-se a influência do substrato, temperatura e luz. Não se observou qualquer tipo de dormência, sendo as temperaturas de 20, 25 e 20-30C, em areia ou vermiculita, apropriadas para a germinação in vivo. Definiu-se também uma metodologia eficiente de germinação sob condições in vitro, e as plântulas obtidas foram utilizadas como fonte de explantes para os estudos de propagação in vitro. A resposta morfogênica foi avaliada considerando-se a origem e tipo do explante, tipos e concentrações de reguladores de crescimento e número de subculturas. A metodologia empregada mostrou-se eficiente para a produção de brotos e manutenção de estoques de plantas in vitro que serviram como fonte de explantes. A melhor condição para a propagação in vitro foi definida em meio solidificado contendo BA, independentemente do tipo de explante e da origem. Os brotos obtidos foram alongados, enraizados e aclimatizados. Também foi estabelecida a cultura de raízes e a regeneração de brotos a partir destas culturas. Avaliou-se o efeito da origem do explante, assim como dos tipos e concentrações de fitorreguladores sobre a proliferação de raízes e a regeneração de brotos. O fitorregulador AIB propiciou maior multiplicação das raízes, enquanto BA mostrou-se eficiente na regeneração de brotos a partir das raízes recém-formadas. Foi estabelecido ainda um protocolo de cultura de calos e de suspensões celulares. Avaliou-se o efeito da origem e do tipo de explante, dos tipos e das concentrações de fitorreguladores sobre a calogênese. A combinação de PIC com KIN foi a mais eficiente para a indução de calos em explantes de plântulas obtidas a partir de germinação in vitro, produzindo calos que foram mantidos por pelo menos dois anos. As suspensões celulares também foram estabelecidas em meio contendo PIC + KIN, mantendo uma produção de biomassa de cerca de cinco vezes o peso fresco inicial por três sucessivas subculturas. Análises histoquímicas e fitoquímicas revelaram a presença de alcaloides nos calos e nas suspensões celulares. Foram realizadas análises fitoquímicas de plantas de campo, plantas aclimatizadas, plantas mantidas em estoque in vitro e culturas de raízes, as quais indicaram a presença de derivados de glicosinolatos. Os resultados demonstraram a viabilidade de produção de material vegetal de C. dendroides por meio de métodos biotecnológicos e a produção in vitro de metabólitos de importância medicinal / Cleome dendroides is an endemic species of the Atlantic Forest of Rio de Janeiro and Espírito Santo states, biome changed by intense human activities that threaten its populations. There are no physiological, biotechnological, phytochemical or pharmacological studies of this specie. Considering the phytochemical profile and the medical potential of the genus, it becomes relevant to establish protocols for the production of plants and metabolites of C. dendroides using different in vitro culture systems. In this work, studies were performed on the in vivo germination of the species evaluating the influence of the substrate, temperature and light. There was no dormancy, and germination was achieved at 20, 25 and 20-30C, on sand or vermiculite substrates. An efficient methodology of germination under in vitro conditions was defined by comparing the different stages of post-seminal development with seedlings from germination under in vivo conditions. The plantlets obtained from the in vitro germination were used as a source of explants for in vitro propagation system. The morphogenic response was evaluated considering the source and type of explant, types and concentrations of growth regulators and number of subcultures. The methodology was efficient for the production of shoots and maintenance of in vitro plants. The best condition for in vitro propagation was using solidified medium supplemented with BA, regardless of the tested explants. The shoots were efficiently elongated, rooted and acclimatized. It was also established an efficient protocol for root culture and shoots regeneration from these cultures. The effect of source of explant, the types and growth regulator concentrations on the proliferation of roots and shoot regeneration was evaluated. IBA provided higher multiplication rates of the roots, whereas BA was effective in the regeneration of shoots from the newly formed roots. A protocol of callus culture and cell suspension culture was established. The effect of the origin and type of explant, the types and concentrations of growth regulators on callus formation was evaluated. PIC + KIN was the most efficient combination for callus induction from explants derived from in vitro germinated seedlings. Callus cultures were maitained for at least two years. Cell suspension cultures were established with the same combination of growth regulators (PIC + KIN), maintaining a biomass of about five times the initial fresh weight of three successive subcultures. Histochemical and phytochemical analysis revealed the presence of alkaloids in callus and suspension cell cultures. Phytochemical analyses of field plants, acclimatization in vitro plant and culture roots were performed, which indicated the presence of glucosinolate derivatives. The results demonstrated the possibility of producing medicinal important metabolites from C. dendroides by biotechnological methods

Parmi les nombreux effets bénéfiques des phospholipides on retient essentiellement leur rôle dans la protection du système cardio-vasculaire, l'amélioration de la mémoire et de l'apprentissage. Ces effets peuvent s'expliquer en partie par le fait que les phospholipides sont riches en acide gras polyinsaturés (acides eicosapentaénoïque et docosahexaénoïque) ou les acides gras essentiels. C’est pourquoi il nous est apparu comme étant important d’explorer des sources naturelles potentielles contenant des phospholipides polyinsaturés destinées au développement de produits alimentaires nouveaux supplémentés en phospholipides.Ce travail a permis de mettre au point des méthodes d’extraction, de purification et de séparation des phospholipides afin de caractèriser les sources naturelles de phospholipides polyinsaturés. Une supplémentation des aliments avec des phospholipides polyinsaturés ne peut être envisagé sans avoir une bonne connaissance de leur stabilité au cours de la transformation et de la conservation des aliments. Nous avons donc développé des méthodes d’identification des produits de dégradation des phospholipides et de détermination de leur cinétique d’oxydation pendant les traitements thermiques. Ainsi, nous avons montré que les phospholipides sont plus stables que les triacylglycérides, ceci étant du probablement à la présence d’un groupe aminé dans la tête polaire. / Among the numerous beneficial effects of phospholipides can highlight their role in protecting the cardiovascular system and improving memory and learning. These effects can be partially explained by the fact that phospholipids are rich in polyunsaturated (eicosapentaenoic and docosahexaenoic acids) or essential fatty acids. Thus, it is very significant to explore potential food sources containing polyunsaturated rich phospholipids for the development new food products supplemented with phospholipids.This work allowed a series method for the extraction, purification, separation and quantification of phospholipids in order to characterize the polyunsaturated phospholipid sources. Food supplementation with polyunsaturated phospholipids rises however the question of their stability during food processing at high temperature. Then we have developed methods to identify phospholipids degradation products and determine their kinetics of the oxidation during thermal treatment which is a widespread food processing.Phospholipids (PE and PC) are more stable than triacylglyceride, this is due to the presence of an amino group in the molecule.