Displaying publications 1 - 20 of 22 in total

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  1. Fluorescence probing of the temperature-induced phase transition in a glycolipid self-assembly: hexagonal ↔ micellar and cubic ↔ lamellar
    Zahid NI, Abou-Zied OK, Hashim R, Heidelberg T
    Langmuir, 2012 Mar 20;28(11):4989-95.
    PMID: 22364590 DOI: 10.1021/la3001976
    Water-driven self-assembly of lipids displays a variety of liquid crystalline phases that are crucial for membrane functions. Herein, we characterize the temperature-induced phase transitions in two compositions of an aqueous self-assembly system of the octyl β-D-glucoside (βGlcOC(8)) system, using steady-state and time-resolved fluorescence measurements. The phase transitions hexagonal ↔ micellar and cubic ↔ lamellar were investigated using tryptophan (Trp) and two of its ester derivatives (Trp-C(4) and Trp-C(8)) to probe the polar headgroup region and pyrene to probe the hydrophobic tail region. The polarity of the headgroup region was estimated to be close to that of simple alcohols (methanol and ethanol) for all phases. The pyrene fluorescence indicates that the pyrene molecules are dispersed among the tails of the hydrophobic region, yet remain in close proximity to the polar head groups. Comparing the present results with our previously reported one for βMaltoOC(12), increasing the tail length of the hexagonal phase from C(8) to C(12) leads to less interaction with pyrene, which is attributed to the more random and wobbling motion of the longer alkyl tail. We measured a reduction (more hydrophobic) in the ratio of the vibronic peak intensities of pyrene (I(1)/I(3)) for the lamellar phase compared to that of the cubic phase. The higher polarity in the cubic phase can be correlated to the nature of its interface, which curves toward the bulk water. This geometry also explains the slight reduction in polarity of the headgroup region compared to the other phases. Upon the addition of Trp-C(8), the fluorescence lifetime of pyrene is reduced by 28% in the lamellar and cubic phases, whereas the I(1)/I(3) value is only slightly reduced. The results reflect the dominant role of dynamic interaction mechanism between the C(8) chain of Trp-C(8) and pyrene. This mechanism may be important for these two phases since they participate in the process of membrane fusion. Both lipid compositions show completely reversible temperature-induced phase transitions, reflecting the thermodynamic equilibrium structures of their mesophases. Probing both regions of the different lipid phases reveals a large degree of heterogeneity and flexibility of the lipid self-assembly. These properties are crucial for carrying out different biological functions such as the ability to accommodate various molecular sizes.
    Matched MeSH terms: Glycolipids/chemistry*
  2. Functionalized glycolipids for potential bioconjugation of vesicles
    Tabandeh M, Goh EW, Salman AA, Heidelberg T, Duali Hussen RS
    Carbohydr Res, 2018 Nov;469:14-22.
    PMID: 30196011 DOI: 10.1016/j.carres.2018.08.016
    Two azide-terminated oligoethylene oxide spacered glycolipids have been synthesized, and their assembly behavior has been studied in comparison to the corresponding base surfactants. The results suggest potential of the Guerbet lactoside-based compound for targeted drug delivery, while a coiling of the ethylene oxide linker disfavors the application of the glucoside.
    Matched MeSH terms: Glycolipids/chemistry*
  3. Phase sensitive molecular dynamics of self-assembly glycolipid thin films: a dielectric spectroscopy investigation
    Velayutham TS, Ng BK, Gan WC, Abd Majid WH, Hashim R, Zahid NI, et al.
    J Chem Phys, 2014 Aug 28;141(8):085101.
    PMID: 25173043 DOI: 10.1063/1.4893873
    Glycolipid, found commonly in membranes, is also a liquid crystal material which can self-assemble without the presence of a solvent. Here, the dielectric and conductivity properties of three synthetic glycolipid thin films in different thermotropic liquid crystal phases were investigated over a frequency and temperature range of (10(-2)-10(6) Hz) and (303-463 K), respectively. The observed relaxation processes distinguish between the different phases (smectic A, columnar/hexagonal, and bicontinuous cubic Q) and the glycolipid molecular structures. Large dielectric responses were observed in the columnar and bicontinuous cubic phases of the longer branched alkyl chain glycolipids. Glycolipids with the shortest branched alkyl chain experience the most restricted self-assembly dynamic process over the broad temperature range studied compared to the longer ones. A high frequency dielectric absorption (Process I) was observed in all samples. This is related to the dynamics of the hydrogen bond network from the sugar group. An additional low-frequency mechanism (Process II) with a large dielectric strength was observed due to the internal dynamics of the self-assembly organization. Phase sensitive domain heterogeneity in the bicontinuous cubic phase was related to the diffusion of charge carriers. The microscopic features of charge hopping were modelled using the random walk scheme, and two charge carrier hopping lengths were estimated for two glycolipid systems. For Process I, the hopping length is comparable to the hydrogen bond and is related to the dynamics of the hydrogen bond network. Additionally, that for Process II is comparable to the bilayer spacing, hence confirming that this low-frequency mechanism is associated with the internal dynamics within the phase.
    Matched MeSH terms: Glycolipids/chemistry*
  4. Investigation of the effect of sugar stereochemistry on biologically relevant lyotropic phases from branched-chain synthetic glycolipids by small-angle X-ray scattering
    Zahid NI, Conn CE, Brooks NJ, Ahmad N, Seddon JM, Hashim R
    Langmuir, 2013 Dec 23;29(51):15794-804.
    PMID: 24274824 DOI: 10.1021/la4040134
    Synthetic branched-chain glycolipids are suitable as model systems in understanding biological cell membranes, particularly because certain natural lipids possess chain branching. Herein, four branched-chain glycopyranosides, namely, 2-hexyl-decyl-α-D-glucopyranoside (α-Glc-OC10C6), 2-hexyl-decyl-β-D-glucopyranoside (β-Glc-OC10C6), 2-hexyl-decyl-α-D-galactopyranoside (α-Gal-OC10C6), and 2-hexyl-decyl-β-D-galactopyranoside (β-Gal-OC10C6), with a total alkyl chain length of 16 carbon atoms have been synthesized, and their phase behavior has been studied. The partial binary phase diagrams of these nonionic surfactants in water were investigated by optical polarizing microscopy (OPM) and small-angle X-ray scattering (SAXS). The introduction of chain branching in the hydrocarbon chain region is shown to result in the formation of inverse structures such as inverse hexagonal and inverse bicontinuous cubic phases. A comparison of the four compounds showed that they exhibited different polymorphism, especially in the thermotropic state, as a result of contributions from anomeric and epimeric effects according to their stereochemistry. The neat α-Glc-OC10C6 compound exhibited a lamellar (Lα) phase whereas dry α-Gal-OC10C6 formed an inverse bicontinuous cubic Ia3d (QII(G)) phase. Both β-anomers of glucoside and galactoside adopted the inverse hexagonal phase (HII) in the dry state. Generally, in the presence of water, all four glycolipids formed inverse bicontinuous cubic Ia3d (QII(G)) and Pn3m (QII(D)) phases over wide temperature and concentration ranges. The formation of inverse nonlamellar phases by these Guerbet branched-chain glycosides confirms their potential as materials for novel biotechnological applications such as drug delivery and crystallization of membrane proteins.
    Matched MeSH terms: Glycolipids/chemistry*
  5. N-linked glycolipids by Staudinger coupling of glycosylated alkyl diazides with fatty acids
    Salman SM, Heidelberg T, Bin Tajuddin HA
    Carbohydr Res, 2013 Jun 28;375:55-62.
    PMID: 23685811 DOI: 10.1016/j.carres.2013.03.028
    Aiming for new glycolipids with enhanced chemical stability and close structural similarity to natural cell membrane lipids for the development of a drug delivery system, we have synthesized double amide analogs of glyco-glycerolipids. The synthesis applied a Staudinger reaction based coupling of a 1,3-diazide with fatty acid chlorides. While the concept furnished the desired glucosides in reasonable yields, the corresponding lactosides formed a tetrahydropyrimidine based 1:1 coupling product instead. This unexpected coupling result likely originates from steric hindrance at the iminophosphorane intermediate and provides an interesting core structure for potentially bioactive surfactants. The assembly behavior of both glycolipid types was investigated by optical polarizing microscopy, DSC and surface tension studies.
    Matched MeSH terms: Glycolipids/chemistry*
  6. DFT study of glucose based glycolipid crown ethers and their complexes with alkali metal cations Na(+) and K(+)
    Nguan H, Ahmadi S, Hashim R
    J Mol Model, 2012 Dec;18(12):5041-50.
    PMID: 22752540 DOI: 10.1007/s00894-012-1497-x
    A theoretical study of a series of five glucose based glycolipid crown ethers and their complexes with Na(+) and K(+) was performed using the density functional theory with B3LYP/6-31 G* to obtain the optimized geometrical structures and electronic properties. The local nucleophilicity of the five molecules was investigated using Fukui function, while the global nucleophilicity was calculated from the ionization potential and electron affinity. The structures and coordination of the complexes were studied to identify the best match of the glycolipid crown ethers with cations. In general, it was found that the oxygen atoms pairs O2 and O3 (or O4 and O6) on the sugar ring are constrained from moving toward the cation, which results in a weaker O-cation coordination strength for the oxygen pair compared to the other oxygen atoms in the crown ether ring. The thermodynamic properties of the binding of the complexes and the exchange reaction in gas phase were evaluated. The cation selectivity pattern among the five molecules was in good agreement with the experiment.
    Matched MeSH terms: Glycolipids/chemistry*
  7. Molecular dynamics study of anhydrous lamellar structures of synthetic glycolipids: effects of chain branching and disaccharide headgroup
    Achari VM, Nguan HS, Heidelberg T, Bryce RA, Hashim R
    J Phys Chem B, 2012 Sep 27;116(38):11626-34.
    PMID: 22967067
    Glycolipids form materials of considerable potential for a wide range of surfactant and thin film applications. Understanding the effect of glycolipid covalent structure on the properties of their thermotropic and lyotropic assemblies is a key step toward rational design of new glycolipid-based materials. Here, we perform molecular dynamics simulations of anhydrous bilayers of dodecyl β-maltoside, dodecyl β-cellobioside, dodecyl β-isomaltoside, and a C(12)C(10) branched β-maltoside. Specifically, we examine the consequences of chain branching and headgroup identity on the structure and dynamics of the lamellar assemblies. Chain branching of the glycolipid leads to measurable differences in the dimensions and interactions of the lamellar assembly, as well as a more fluid-like hydrophobic chain region. Substitution of the maltosyl headgroup of βMal-C(12) by an isomaltosyl moiety leads to a significant decrease in bilayer spacing as well as a markedly altered pattern of inter-headgroup hydrogen bonding. The distinctive simulated structures of the two regioisomers provide insight into the difference of ~90 °C in their observed clearing temperatures. For all four simulated glycolipid systems, with the exception of the sn-2 chain of the branched maltoside, the alkyl chains are ordered and exhibit a distinct tilt, consistent with recent crystallographic analysis of a branched chain Guerbet glycoside. These insights into structure-property relationships from simulation provide an important molecular basis for future design of synthetic glycolipid materials.
    Matched MeSH terms: Glycolipids/chemistry*
  8. Molecular dynamics of anhydrous glycolipid self-assembly in lamellar and hexagonal phases
    Velayutham TS, Nguan HS, Ng BK, Gan WC, Manickam Achari V, Zahid NI, et al.
    Phys Chem Chem Phys, 2016 06 01;18(22):15182-90.
    PMID: 27199168 DOI: 10.1039/c6cp00583g
    The molecular dynamics of a synthetic branched chain glycolipid, 2-decyl-tetradecyl-β-d-maltoside (C14-10G2), in the dry assemblage of smectic and columnar liquid crystal phases has been studied by dielectric spectroscopy as a function of frequency and temperature during the cooling process. Strong relaxation modes were observed corresponding to the tilted smectic and columnar phases, respectively. At low frequency (∼900 Hz to 1 kHz) in the smectic phase, Process I* was observed due to the tilted sugar bilayer structure. The process continued in the columnar phase (Process I) with an abrupt dynamic change due to phase transition in the frequency range of ∼1.3 kHz to 22 kHz. An additional process (Process II) was observed in the columnar phase with a broader relaxation in the frequency range of ∼10 Hz to 1 kHz. A bias field dependence study was performed in the columnar phase and we found that the relaxation strength rapidly decreased with increased applied dc bias field. This relaxation originates from a collective motion of polar groups within the columns. The results of dielectric spectroscopy were supported by a molecular dynamics simulation study to identify the origin of the relaxation processes, which could be related to the chirality and hydrogen bonds of the sugar lipid.
    Matched MeSH terms: Glycolipids/chemistry*
  9. Renewable resources-based approach to biantennary glycolipids
    Tabandeh M, Salman AA, Goh EW, Heidelberg T, Hussen RSD
    Chem Phys Lipids, 2018 05;212:111-119.
    PMID: 29409839 DOI: 10.1016/j.chemphyslip.2018.01.011
    A new synthesis approach towards biantennary lipids of Guerbet glycoside type was developed based on oleic acid as sustainable resource. Functionalization of the double bond provided access to primary alcohols with α-branched C19-skeleton. Formulation studies with corresponding lactosides indicated formation of vesicles with high assembly stability. A relatively narrow bimodal size distribution of the latter, which turns into a narrow unimodal distribution of small vesicles upon addition of an ionic cosurfactant, suggests potential for a vesicular drug delivery system.
    Matched MeSH terms: Glycolipids/chemistry*
  10. Fulltext Conformational dynamics of dry lamellar crystals of sugar based lipids: an atomistic simulation study
    ManickamAchari V, Bryce RA, Hashim R
    PLoS One, 2014;9(6):e101110.
    PMID: 24978205 DOI: 10.1371/journal.pone.0101110
    The rational design of a glycolipid application (e.g. drug delivery) with a tailored property depends on the detailed understanding of its structure and dynamics. Because of the complexity of sugar stereochemistry, we have undertaken a simulation study on the conformational dynamics of a set of synthetic glycosides with different sugar groups and chain design, namely dodecyl β-maltoside, dodecyl β-cellobioside, dodecyl β-isomaltoside and a C12C10 branched β-maltoside under anhydrous conditions. We examined the chain structure in detail, including the chain packing, gauche/trans conformations and chain tilting. In addition, we also investigated the rotational dynamics of the headgroup and alkyl chains. Monoalkylated glycosides possess a small amount of gauche conformers (∼20%) in the hydrophobic region of the lamellar crystal (LC) phase. In contrast, the branched chain glycolipid in the fluid Lα phase has a high gauche population of up to ∼40%. Rotational diffusion analysis reveals that the carbons closest to the headgroup have the highest correlation times. Furthermore, its value depends on sugar type, where the rotational dynamics of an isomaltose was found to be 11-15% and more restrained near the sugar, possibly due to the chain disorder and partial inter-digitation compared to the other monoalkylated lipids. Intriguingly, the present simulation demonstrates the chain from the branched glycolipid bilayer has the ability to enter into the hydrophilic region. This interesting feature of the anhydrous glycolipid bilayer simulation appears to arise from a combination of lipid crowding and the amphoteric nature of the sugar headgroups.
    Matched MeSH terms: Glycolipids/chemistry
  11. Atomistic simulation studies of the α/β-glucoside and galactoside in anhydrous bilayers: effect of the anomeric and epimeric configurations
    Ahmadi S, Manickam Achari V, Nguan H, Hashim R
    J Mol Model, 2014 Mar;20(3):2165.
    PMID: 24623320 DOI: 10.1007/s00894-014-2165-0
    Fully atomistic molecular dynamics simulation studies of thermotropic bilayers were performed using a set of glycosides namely n-octyl-β-D-glucopyranoside (β-C8Glc), n-octyl-α-D-glucopyranoside (α-C8Glc), n-octyl-β-D-galactopyranoside (β-C8Gal), and n-octyl-α-D-galactopyranoside (α-C8Gal) to investigate the stereochemical relationship of the epimeric/anomeric quartet liner glycolipids with the same octyl chain group. The results showed that, the anomeric stereochemistry or the axial/equatorial orientation of C1-O1 (α/β) is an important factor controlling the area and d-spacing of glycolipid bilayer systems in the thermotropic phase. The head group tilt angle and the chain ordering properties are affected by the anomeric effect. In addition, the L(C) phase of β-C8Gal, is tilting less compared to those in the fluid L(α). The stereochemistry of the C4-epimeric (axial/equatorial) and anomeric (α/β) centers simultaneously influence the inter-molecular hydrogen bond. Thus, the trend in the values of the hydrogen bond for these glycosides is β-C8Gal > α-C8Glc > β-C8Glc > α-C8Gal. The four bilayer systems showed anomalous diffusion behavior with an observed trend for the diffusion coefficients; and this trend is β-C8Gal > β-C8Glc > α-C8Gal > α-C8Glc. The "bent" configuration of the α-anomer results in an increase of the hydrophobic area, chain vibration and chain disorganization. Since thermal energy is dispensed more entropically for the chain region, the overall molecular diffusion decreases.
    Matched MeSH terms: Glycolipids/chemistry*
  12. Influence of nonionic branched-chain alkyl glycosides on a model nano-emulsion for drug delivery systems
    Ahmad N, Ramsch R, Llinàs M, Solans C, Hashim R, Tajuddin HA
    Colloids Surf B Biointerfaces, 2014 Mar 1;115:267-74.
    PMID: 24384142 DOI: 10.1016/j.colsurfb.2013.12.013
    The effect of incorporating new nonionic glycolipid surfactants on the properties of a model water/nonionic surfactant/oil nano-emulsion system was investigated using branched-chain alkyl glycosides: 2-hexyldecyl-β(/α)-D-glucoside (2-HDG) and 2-hexyldecyl-β(/α)-D-maltoside (2-HDM), whose structures are closely related to glycero-glycolipids. Both 2-HDG and 2-HDM have an identical hydrophobic chain (C16), but the former consists a monosaccharide glucose head group, in contrast to the latter which has a disaccharide maltose unit. Consequently, their hydrophilic-lipophilic balance (HLB) is different. The results obtained have shown that these branched-chain alkyl glycosides affect differently the stability of the nano-emulsions. Compared to the model nano-emulsion, the presence of 2-HDG reduces the oil droplet size, whereas 2-HDM modify the properties of the model nano-emulsion system in terms of its droplet size and storage time stability at high temperature. These nano-emulsions have been proven capable of encapsulating ketoprofen, showing a fast release of almost 100% in 24h. Thus, both synthetically prepared branched-chain alkyl glycosides with mono- and disaccharide sugar head groups are suitable as nano-emulsion stabilizing agents and as drug delivery systems in the future.
    Matched MeSH terms: Glycolipids/chemistry
  13. The effect of the head group on branched-alkyl chain surfactants in glycolipid/n-octane/water ternary system
    Nainggolan I, Radiman S, Hamzah AS, Hashim R
    Colloids Surf B Biointerfaces, 2009 Oct 1;73(1):84-91.
    PMID: 19540095 DOI: 10.1016/j.colsurfb.2009.05.021
    Two novel glycolipids have been synthesized and their phase behaviour studied. They have been characterized using FT-IR, FAB and 13C NMR and 1H NMR to ensure the purity of novel glycolipids. The two glycolipids are distinguished based on the head group of glycolipids (monosaccharide/glucose and disaccharide/maltose). These two novel glycolipids have been used as surfactant to perform two phase diagrams. Phase behaviours that have been investigated are 2-hexyldecyl-beta-D-glucopyranoside (2-HDG)/n-octane/water ternary system and 2-hexyldecyl-beta-D-maltoside (2-HDM)/n-octane/water ternary system. SAXS and polarizing optical microscope have been used to study the phase behaviours of these two surfactants in ternary phase diagram. Study of effect of the head group on branched-alkyl chain surfactants in ternary system is a strategy to derive the structure-property relationship. For comparison, 2-HDM and 2-HDG have been used as surfactant in the same ternary system. The phase diagram of 2-hexyldecyl-beta-D-maltoside/n-octane/water ternary system exhibited a Lalpha phase at a higher concentration regime, followed with two phases and a micellar solution region in a lower concentration regime. The phase diagram of 2-HDG/water/n-octane ternary system shows hexagonal phase, cubic phase, rectangular ribbon phase, lamellar phase, cubic phase as the surfactant concentration increase.
    Matched MeSH terms: Glycolipids/chemistry*
  14. Rhamnolipid produced by Pseudomonas aeruginosa USM-AR2 facilitates crude oil distillation
    Asshifa Md Noh N, Al-Ashraf Abdullah A, Nasir Mohamad Ibrahim M, Ramli Mohd Yahya A
    J Gen Appl Microbiol, 2012;58(2):153-61.
    PMID: 22688247
    A biosurfactant-producing and hydrocarbon-utilizing bacterium, Pseudomonas aeruginosa USM-AR2, was used to assist conventional distillation. Batch cultivation in a bioreactor gave a biomass of 9.4 g L(-1) and rhamnolipid concentration of 2.4 g L(-1) achieved after 72 h. Biosurfactant activity (rhamnolipid) was detected by the orcinol assay, emulsification index and drop collapse test. Pretreatment of crude oil TK-1 and AG-2 with a culture of P. aeruginosa USM-AR2 that contains rhamnolipid was proven to facilitate the distillation process by reducing the duration without reducing the quality of petroleum distillate. It showed a potential in reducing the duration of the distillation process, with at least 2- to 3-fold decreases in distillation time. This is supported by GC-MS analysis of the distillate where there was no difference between compounds detected in distillate obtained from treated or untreated crude oil. Calorimetric tests showed the calorie value of the distillate remained the same with or without treatment. These two factors confirmed that the quality of the distillate was not compromised and the incubation process by the microbial culture did not over-degrade the oil. The rhamnolipid produced by this culture was the main factor that enhanced the distillation performance, which is related to the emulsification of hydrocarbon chains in the crude oil. This biotreatment may play an important role to improve the existing conventional refinery and distillation process. Reducing the distillation times by pretreating the crude oil with a natural biosynthetic product translates to energy and cost savings in producing petroleum products.
    Matched MeSH terms: Glycolipids/chemistry
  15. Human Milk Fat Globule Membrane Contains Hundreds of Abundantly Expressed and Nutritionally Beneficial Proteins That Are Generally Lacking in Caprine Milk
    Juvarajah T, Wan-Ibrahim WI, Ashrafzadeh A, Othman S, Hashim OH, Fung SY, et al.
    Breastfeed Med, 2018 11;13(9):631-637.
    PMID: 30362820 DOI: 10.1089/bfm.2018.0057
    BACKGROUND: Bioactive proteins from milk fat globule membrane (MFGM) play extensive roles in cellular processes and defense mechanisms in infants. The aims of this study were to identify differences in protein compositions in human and caprine MFGM using proteomics and evaluate possible nutritional benefits of caprine milk toward an infant's growth, as an alternative when breastfeeding or human milk administration is not possible or inadequate.

    MATERIALS AND METHODS: Human and caprine MFGM proteins were isolated and analyzed, initially by polyacrylamide gel electrophoresis, and subsequently by quadrupole time-of-flight liquid chromatography-mass spectrometry. This was then followed by database search and gene ontology analysis. In general, this method selectively analyzed the abundantly expressed proteins in milk MFGM.

    RESULTS: Human MFGM contains relatively more abundant bioactive proteins compared with caprine. While a total of 128 abundant proteins were detected in the human MFGM, only 42 were found in that of the caprine. Seven of the bioactive proteins were apparently found to coexist in both human and caprine MFGM.

    RESULTS/DISCUSSION: Among the commonly detected MFGM proteins, lactotransferrin, beta-casein, lipoprotein lipase, fatty acid synthase, and butyrophilin subfamily 1 member A1 were highly expressed in human MFGM. On the other hand, alpha-S1-casein and EGF factor 8 protein, which are also nutritionally beneficial, were found in abundance in caprine MFGM. The large number of human MFGM abundant proteins that were generally lacking in caprine appeared to mainly support human metabolic and developmental processes.

    CONCLUSION: Our data demonstrated superiority of human MFGM by having more than one hundred nutritionally beneficial and abundantly expressed proteins, which are clearly lacking in caprine MFGM. The minor similarity in the abundantly expressed bioactive proteins in caprine MFGM, which was detected further, suggests that it is still nutritionally beneficial, and therefore should be included when caprine milk-based formula is used as an alternative.

    Matched MeSH terms: Glycolipids/chemistry*
  16. Fulltext Performance of Green Surfactants in the Formulation of Heavy-Duty Laundry Liquid Detergents (HDLD) with Special Emphasis on Palm Based Alpha Methyl Ester Sulfonates (α-MES)
    Low SY, Tan JY, Ban ZH, Siwayanan P
    J Oleo Sci, 2021 Aug 05;70(8):1027-1037.
    PMID: 34248098 DOI: 10.5650/jos.ess21078
    Liquid detergent has an increasing demand in North America, Western Europe, and Southeast Asia countries owing to its convenience to use and efficiency to clean. Alpha methyl ester sulfonates (α-MES), an anionic surfactant derived from palm oil based methyl ester, was reported to have lower manufacturing cost, good detergency with less dosage, excellent biodegradability, higher tolerance to hard water, and lower eco-toxicity as compared to linear alkylbenzene sulfonates (LABS). LABS was known as the workhorse of the detergent industry in the 20th century. Although palm-based α-MES was successfully used as the sole surfactant in powder detergent, there are still some unsettled technical issues related to phase stability and viscosity when using this anionic surfactant in heavy-duty laundry liquid detergent formulations. This paper will review not only the market overview of detergents, the application and performance of green surfactants in laundry detergents but also will highlight the technical issues related to the application of palm-based α-MES in laundry liquid detergent and some of the possible methods to overcome the formulation adversities.
    Matched MeSH terms: Glycolipids/chemistry
  17. Phospholipid-Protein Structured Membrane for Microencapsulation of DHA Oil and Evaluation of Its In Vitro Digestibility: Inspired by Milk Fat Globule Membrane
    Chen Y, Ge H, Zheng Y, Zhang H, Li Y, Su X, et al.
    J Agric Food Chem, 2020 Jun 03;68(22):6190-6201.
    PMID: 32379465 DOI: 10.1021/acs.jafc.0c01250
    The present study aims to design a milk fat globule membrane (MFGM)-inspired structured membrane (phospholipid- and protein-rich) for microencapsulation of docosahexaenoic acid (DHA) oil. DHA-enriched oil emulsions were prepared using different ratios of sunflower phospholipid (SPL), proteins [whey protein concentrate (WPC), soy protein isolate (SPI), and sodium caseinate (SC)], and maltodextrin and spray-dried to obtain DHA microcapsules. The prepared DHA oil emulsions have nanosized particles. SPLs were found to affect the secondary structure of WPC, which resulted in increased exposure of the protein hydrophobic site and emulsion stability. SPL also reduced the surface tension and viscosity of the DHA oil emulsions. In vitro digestion of the spray-dried DHA microcapsules showed that they were able to effectively resist gastric proteolysis and protect their bioactivity en route to the intestine. The DHA microcapsules have a high lipid digestibility in the small intestine with a high DHA hydrolysis efficiency (74.3%), which is higher than that of commercial DHA microcapsules.
    Matched MeSH terms: Glycolipids/chemistry*
  18. Production and characterization of rhamnolipid using palm oil agricultural refinery waste
    Radzuan MN, Banat IM, Winterburn J
    Bioresour Technol, 2017 Feb;225:99-105.
    PMID: 27888734 DOI: 10.1016/j.biortech.2016.11.052
    In this research we assess the feasibility of using palm oil agricultural refinery waste as a carbon source for the production of rhamnolipid biosurfactant through fermentation. The production and characterization of rhamnolipid produced by Pseudomonas aeruginosa PAO1 grown on palm fatty acid distillate (PFAD) under batch fermentation were investigated. Results show that P. aeruginosa PAO1 can grow and produce 0.43gL(-1) of rhamnolipid using PFAD as the sole carbon source. Identification of the biosurfactant product using mass spectrometry confirmed the presence of monorhamnolipid and dirhamnolipid. The rhamnolipid produced from PFAD were able to reduce surface tension to 29mNm(-1) with a critical micelle concentration (CMC) 420mgL(-1) and emulsify kerosene and sunflower oil, with an emulsion index up to 30%. Results demonstrate that PFAD could be used as a low-cost substrate for rhamnolipid production, utilizing and transforming it into a value added biosurfactant product.
    Matched MeSH terms: Glycolipids/chemistry
  19. Devosia elaeis sp. nov., isolated from oil palm rhizospheric soil
    Mohd Nor MN, Sabaratnam V, Tan GYA
    Int J Syst Evol Microbiol, 2017 Apr;67(4):851-855.
    PMID: 27902276 DOI: 10.1099/ijsem.0.001683
    A bacterial isolate, designated strain S37T, was isolated from the rhizosphere of oil palm (Elaeis guineensis). Strain S37T was found to be Gram-stain-negative, aerobic, motile and rod shaped. Based on 16S rRNA gene sequence analysis, strain S37T was most closely related to Devosia albogilva IPL15T (97.3 %), Devosia chinhatensis IPL18T (96.8 %) and Devosia subaequoris HST3-14T (96.5 %). The G+C content of the genomic DNA was 63.0 mol%, and dominant cellular fatty acids were summed feature 8 (C18 : 1ω7c and/or C18 : 1ω6c), 11-methyl C18 : 1ω7c and C16 : 0. The predominant isoprenoid quinone was ubiquinone-10 (Q-10), and the major polar lipids were phosphatidylglycerol, diphosphatidylglycerol, glycolipid and phospholipids. Based on the polyphasic taxonomic data, it is clear that strain S37T represents a novel species of the genus Devosia within the family Hyphomicrobiaceae, for which we propose the name Devosia elaeis sp. nov., with strain S37T (=TBRC 5145T=LMG 29420T) as the type strain.
    Matched MeSH terms: Glycolipids/chemistry
  20. Vitellibacter aquimaris sp. nov., a marine bacterium isolated from seawater
    Thevarajoo S, Selvaratnam C, Goh KM, Hong KW, Chan XY, Chan KG, et al.
    Int J Syst Evol Microbiol, 2016 Sep;66(9):3662-3668.
    PMID: 27334651 DOI: 10.1099/ijsem.0.001248
    A Gram-staining-negative, aerobic, yellow-orange-pigmented, rod-shaped bacterium designated D-24T was isolated from seawater from sandy shoreline in Johor, Malaysia. The 16S rRNA gene sequence analysis revealed that strain D-24T is affiliated with the genus Vitellibacter. It shared more than 96 % sequence similarity with the types of some of the validly published species of the genus: Vitellibactervladivostokensis KMM 3516T (99.5 %), Vitellibactersoesokkakensis RSSK-12T (97.3 %), VitellibacterechinoideorumCC-CZW007T (96.9 %), VitellibacternionensisVBW088T (96.7 %) and Vitellibacteraestuarii JCM 15496T (96.3 %). DNA-DNA hybridization and genome-based analysis of average nucleotide identity (ANI) of strain D-24T versus V.vladivostokensisKMM 3516T exhibited values of 35.9±0.14 % and 89.26 %, respectively. Strain D-24T showed an even lower ANI value of 80.88 % with V. soesokkakensis RSSK-12T. The major menaquinone of strain D-24T was MK-6, and the predominant fatty acids were iso-C15 : 0 and iso-C17 : 0 3-OH. Strain D-24T contained major amounts of phosphatidylethanolamine, two lipids and two aminolipids, and a phosphoglycolipid that was different to that of other species of the genus Vitellibacter. The genomic DNA G+C content was 40.6 mol%. On the basis of phenotypic properties, DNA-DNA relatedness, ANI value and chemotaxonomic analyses, strain D-24T represents a novel species of the genus Vitellibacter, for which the name Vitellibacter aquimaris sp. nov. is proposed. The type strain is D-24T (=KCTC 42708T=DSM 101732T).
    Matched MeSH terms: Glycolipids/chemistry
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