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Food Research International (Ottawa,... May 2023Hydrophilic phytosterol glycosyl derivatives are synthetic phytosterol analogues by coupling with the glycosyl moiety to improve the water solubility and...
Hydrophilic phytosterol glycosyl derivatives are synthetic phytosterol analogues by coupling with the glycosyl moiety to improve the water solubility and bioaccessibility of free phytosterols. The aim of this study is to clarify the molecular interaction of phytosterol glycosyl derivatives with bile salts and the consequent impact on cholesterol solubilization. Sharp nonlinear decrease in the micellar solubility of cholesterol and accompanying changes in particle size, zeta potential and microtopography of mixed micelles were observed when phytosterol glycosyl derivatives were introduced in cholesterol-loaded bile salt micelles. These results suggested that β-sitosterol glycosyl derivatives molecules indeed participated in the formation of mixed micelles. Further, nuclear magnetic resonance showed that the structural change of mixed micelles was caused by the insertion of β-sitosterol glycosyl derivatives via hydrogen bonds with sodium taurocholate, which resulted in the low cholesterol solubilization. Moreover, the hydrogen-bond interactions were apparently influenced by the glycosyl moiety of β-sitosterol glycosyl derivatives. These molecular mechanisms may contribute to the development of cholesterol-absorption inhibitors.
Topics: Phytosterols; Micelles; Bile Acids and Salts; Solubility; Cholesterol
PubMed: 37087234
DOI: 10.1016/j.foodres.2023.112642 -
Biotechnology Letters Apr 2018To enhance the yield of 9α-hydroxy-4-androstene-3,17-dione (9-OHAD) from phytosterols, a phytosterol transport system was constructed in Mycobacterium sp. strain MS136.
OBJECTIVES
To enhance the yield of 9α-hydroxy-4-androstene-3,17-dione (9-OHAD) from phytosterols, a phytosterol transport system was constructed in Mycobacterium sp. strain MS136.
RESULTS
9-OHAD can be produced via the controlled degradation of phytosterols by mycobacteria. This involves an active transport process that requires trans-membrane proteins and ATP. A phytosterol transport system from Mycobacterium tuberculosis H37Rv was constructed in Mycobacterium sp. strain MS136 by co-expression of an energy-related gene, mceG, and two integrated membrane protein genes, yrbE4A and yrbE4B. The resultant of the Mycobacterium sp. strain MS136-GAB gave 5.7 g 9-OHAD l, which was a 20% increase over 4.7 g l by the wild-type strain. The yield of 9-OHAD was increased to 6.0 g l by optimization of fermentation conditions, when 13 g phytosterols l were fermented for 84 h in 30 ml biotransformation medium in shake flasks.
CONCLUSIONS
Phytosterol transport system plays an active role in the uptake and transport of sterols, cloning of the system improved the mass transfer of phytosterols and increased the production of 9-OHAD.
Topics: Androstenedione; Biological Transport; Fermentation; Metabolic Engineering; Mycobacterium tuberculosis; Phytosterols
PubMed: 29392454
DOI: 10.1007/s10529-018-2520-9 -
Trends in Plant Science May 2024Plant-microbe interactions (PMIs) are regulated through a wide range of mechanisms in which sterols from plants and microbes are involved in numerous ways, including... (Review)
Review
Plant-microbe interactions (PMIs) are regulated through a wide range of mechanisms in which sterols from plants and microbes are involved in numerous ways, including recognition, transduction, communication, and/or exchanges between partners. Phytosterol equilibrium is regulated by PMIs through expression of genes involved in phytosterol biosynthesis, together with their accumulation. As such, PMI outcomes also include plasma membrane (PM) functionalization events, in which phytosterols have a central role, and activation of sterol-interacting proteins involved in cell signaling. In spite (or perhaps because) of such multifaceted abilities, an overall mechanism of sterol contribution is difficult to determine. However, promising approaches exploring sterol diversity, their contribution to PMI outcomes, and their localization would help us to decipher their crucial role in PMIs.
Topics: Plants; Phytosterols; Sterols; Host-Pathogen Interactions; Host Microbial Interactions; Signal Transduction
PubMed: 38565452
DOI: 10.1016/j.tplants.2024.03.002 -
Journal of Food Science Mar 2022Phytosterols have received an extensive attention owing to their excellent cholesterol-lowering activity and the role in cardiovascular diseases prevention. Phytosterol...
Phytosterols have received an extensive attention owing to their excellent cholesterol-lowering activity and the role in cardiovascular diseases prevention. Phytosterol diacid monoesters, the important intermediates in the structural modification of free phytosterols, were usually obtained by chemical method with catalyst. The aim of this research was to provide an eco-friendly approach for the preparation of phytosterol diacid monoester and explore the possible mechanism of their hypocholesteremic effect using model bile mixed micelles. Catalyst-free synthesis of β-sitosterol with succinic anhydride, maleic anhydride, and glutaric anhydride was investigated and optimized. The yields of three β-sitosterol diacid monoesters all reached above 94% under optimum reaction conditions and their chemical structures were confirmed further by mass spectroscopy, Fourier transform infrared spectroscopy, and nuclear magnetic resonance spectroscopy. Compared with β-sitosterol, β-sitosterol diacid monoesters possessed the increased thermal stability (up to an above 355.28°C) and improved solubility in binary mixed micelle system (exceeding 1.7 mM) and similar cholesterol-lowering activity (7.78%-11.05%). Moreover, β-sitosterol diacid monoesters showed the competitive effect on solubilization of cholesterol due to their enhanced micellar incorporation capacity. Overall, the competition with cholesterol in vitro gives useful information about the cholesterol-lowering activity of phytosterol diacid monoesters, which will further expand their applications in the food industry and health. PRACTICAL APPLICATION: Modified phytosterols, phytosterol diacid monoesters, were successfully synthesized in petroleum ether without catalyst. These products enhanced the thermal stability of free phytosterols and reduced the dissolution capacity of cholesterol in model bile mixed micelles due to competitive solubilization. These results indicated that phytosterol diacid monoesters represented cholesterol-lowering potential, which might further expand the applications in the food industry and health.
Topics: Bile; Cholesterol; Micelles; Phytosterols; Solubility
PubMed: 35152409
DOI: 10.1111/1750-3841.16074 -
Applied Biochemistry and Biotechnology Sep 2012A method of synthesizing the phytosterol esters from oleic acid and sterols was studied, using immobilized lipase Candida sp. 99-125 as catalyst. Molar ratio (oleic...
A method of synthesizing the phytosterol esters from oleic acid and sterols was studied, using immobilized lipase Candida sp. 99-125 as catalyst. Molar ratio (oleic acid/phytosterols), temperature, reaction period, organic solvents, catalyst, and silica-gel drier were optimized, and the result showed that 93.4% of the sterols had been esterified under the optimal synthetic condition: the molar ratio of oleic acid/phytosterol is 1:1 in 10 mL iso-octane, immobilized lipase (w, 140% of the sterols), incubated in an orbital shaker (200 rpm) at a temperature of 45 °C for 24 h. The immobilized lipase could be reused for at least 13 times with limited loss of esterification activity. The conversion still maintained up to 86.6%. Hence, this developed process for synthesizing phytosterol esters could be considered as simple and low-energy consumption compared to existing chemical processes.
Topics: Candida; Enzyme Stability; Enzymes, Immobilized; Esterification; Esters; Lipase; Oleic Acids; Phytosterols; Silica Gel; Solvents; Substrate Specificity; Temperature; Time Factors
PubMed: 21822658
DOI: 10.1007/s12010-011-9324-x -
Journal of Agricultural and Food... Jun 2014Water-insoluble phytosterols were developed into a kind of colloidal particle as Pickering stabilizers for emulsions by a classic anti-solvent method using 100% ethanol...
Water-insoluble phytosterols were developed into a kind of colloidal particle as Pickering stabilizers for emulsions by a classic anti-solvent method using 100% ethanol as the organic phase to solubilize the phytosterols and whey protein concentrate (WPC) as the emulsifier. The colloidal particles in the dispersion, with morphology of stacked platelet-like sheets, had a mean diameter of 44.7 and 24.7 μm for the volume- and surface-averaged sizes, respectively. The properties and stability of the emulsions stabilized by these colloidal particles were highly dependent upon the applied total solid concentration (c; in the dispersion) and oil fraction (ø). The results indicated that (1) at a low c value (<1.0%, w/v) the emulsions were susceptible to phase separation, even at a low ø of 0.2, (2) at low ø values (e.g., 0.2 or 0.3) and a relatively high c value (1.0%, w/v, or above), a severe droplet flocculation occurred for the emulsions, and (3) when both c and ø were appropriately high, a kind of self-supporting gel-like emulsions could be formed. More interestingly, a phase inversion of the emulsions from the oil-in-water to water-in-oil type was observed, upon the ø increasing from 0.2 to 0.6 (especially at high c values, e.g., 3.0%, w/v). The elaborated Pickering emulsions stabilized by the phytosterol colloidal particles with a gel-like behavior would provide a candidate to act as a novel delivery system for active ingredients.
Topics: Colloids; Emulsions; Oils; Particle Size; Phytosterols
PubMed: 24848560
DOI: 10.1021/jf404930c -
Science China. Life Sciences Feb 2016Phytosterols play an important role in plant growth and development, including cell division, cell elongation, embryogenesis, cellulose biosynthesis, and cell wall...
Phytosterols play an important role in plant growth and development, including cell division, cell elongation, embryogenesis, cellulose biosynthesis, and cell wall formation. Cotton fiber, which undergoes synchronous cell elongation and a large amount of cellulose synthesis, is an ideal model for the study of plant cell elongation and cell wall biogenesis. The role of phytosterols in fiber growth was investigated by treating the fibers with tridemorph, a sterol biosynthetic inhibitor. The inhibition of phytosterol biosynthesis resulted in an apparent suppression of fiber elongation in vitro or in planta. The determination of phytosterol quantity indicated that sitosterol and campesterol were the major phytosterols in cotton fibers; moreover, higher concentrations of these phytosterols were observed during the period of rapid elongation of fibers. Furthermore, the decrease and increase in campesterol:sitosterol ratio was associated with the increase and decease in speed of elongation, respectively, during the elongation stage. The increase in the ratio was associated with the transition from cell elongation to secondary cell wall synthesis. In addition, a number of phytosterol biosynthetic genes were down-regulated in the short fibers of ligon lintless-1 mutant, compared to its near-isogenic wild-type TM-1. These results demonstrated that phytosterols play a crucial role in cotton fiber development, and particularly in fiber elongation.
Topics: Cholesterol; Cotton Fiber; Mass Spectrometry; Phytosterols; Sitosterols
PubMed: 26803301
DOI: 10.1007/s11427-015-4992-3 -
Nutrients Apr 2024The main objective of this study was to determine plasma levels of PS and to study SNVs rs41360247, rs4245791, rs4148217, and rs11887534 of and the r657152 SNV at the...
The main objective of this study was to determine plasma levels of PS and to study SNVs rs41360247, rs4245791, rs4148217, and rs11887534 of and the r657152 SNV at the ABO blood group locus in a sample of a population treated at our hospital, and to determine whether these SNVs are related to plasma PS concentrations. The secondary objective was to establish the variables associated with plasma PS concentrations in adults. Participants completed a dietary habit questionnaire and a blood sample was collected to obtain the following variables: campesterol, sitosterol, sitostanol, lanosterol, stigmasterol, biochemical parameters, and the SNVs. In addition, biometric and demographic variables were also recorded. In the generalized linear model, cholesterol and age were positively associated with total PS levels, while BMI was negatively related. For rs4245791, homozygous T allele individuals showed a significantly lower campesterol concentration compared with C homozygotes, and the GG alleles of rs657152 had the lowest levels of campesterol compared with the other alleles of the SNV. Conclusions: The screening of certain SNVs could help prevent the increase in plasma PS and maybe PNALD in some patients. However, further studies on the determinants of plasma phytosterol concentrations are needed.
Topics: Adult; Humans; Phytosterols; Lanosterol; Stigmasterol; ABO Blood-Group System; Alleles
PubMed: 38613098
DOI: 10.3390/nu16071067 -
International Journal of Food Sciences... Feb 2013Several studies have observed decreased levels of lipophilic antioxidants after supplementation with phytosterols and stanols. The aim of this study was to examine the... (Randomized Controlled Trial)
Randomized Controlled Trial
Several studies have observed decreased levels of lipophilic antioxidants after supplementation with phytosterols and stanols. The aim of this study was to examine the effect of phytosterol supplementation on plasma total antioxidant capacity in patients with metabolic syndrome. In a parallel arm, randomized placebo-controlled design, 108 patients with metabolic syndrome were assigned to consume yogurt beverage which provided 4 g of phytosterols per day or yogurt beverage without phytosterols. The duration of the study was 2 months and the patients in both groups followed their habitual westernized type diet. Blood samples were drawn at baseline and after 2 months, and the total antioxidant capacity of plasma was measured using the ferric reducing antioxidant power of plasma and oxygen radical absorbance capacity assays. After 2 months of intervention, plasma total antioxidant capacity did not differ between and within the intervention and the control groups. Phytosterol supplementation does not affect plasma antioxidant status.
Topics: Adult; Antioxidants; Beverages; Dietary Supplements; Female; Ferric Compounds; Humans; Male; Metabolic Syndrome; Middle Aged; Phytosterols; Reactive Oxygen Species; Yogurt
PubMed: 22816679
DOI: 10.3109/09637486.2012.706597 -
Bioprocess and Biosystems Engineering Dec 2015The transesterification of phytosterol and soybean oil was performed using Novozym 435 in supercritical carbon dioxide (SC-CO2). The transesterification reaction was...
The transesterification of phytosterol and soybean oil was performed using Novozym 435 in supercritical carbon dioxide (SC-CO2). The transesterification reaction was conducted in soybean oil containing 5-25% phytosterol at 55-95 °C and free-water solvent. The effects of temperature, reaction time, phytosterol concentration, lipase dosage and reaction pressure on the conversion rate of transesterification were investigated. The optimal reaction conditions were the reaction temperature (85 °C), reaction time (1 h), phytosterol concentration (5%), reaction pressure (8 Mpa) and lipase dosage (1%). The highest conversion rate of 92% could be achieved under the optimum conditions. Compared with the method of lipase-catalyzed transesterification of phytosterol and soybean oil at normal pressure, the transesterification in SC-CO2 reduced significantly the reaction temperature and reaction time.
Topics: Candida; Carbon Dioxide; Catalysis; Esterification; Lipase; Phytosterols; Pressure; Soybean Oil; Temperature
PubMed: 26386863
DOI: 10.1007/s00449-015-1469-5