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BioMed Research International 2019L. (Rubiaceae) is a climber which is widely distributed in Asian countries including Malaysia. The plant is traditionally used to treat various diseases including...
L. (Rubiaceae) is a climber which is widely distributed in Asian countries including Malaysia. The plant is traditionally used to treat various diseases including diabetes. This study is to evaluate the enzymatic inhibition activity of twigs extracts and to identify the metabolites responsible for the bioactivity by gas chromatography-mass spectrometry (GC-MS) metabolomics profiling. Three different twig extracts, namely, hexane (PFH), chloroform (PFC), and methanol (PFM), were submerged for their -amylase and -glucosidase inhibition potential in 5 replicates for each. Results obtained from the loading column scatter plot of orthogonal partial least square (OPLS) model revealed the presence of 12 bioactive compounds, namely, dl--tocopherol, n-hexadecanoic acid, 2-hexyl-1-decanol, stigmastanol, 2-nonadecanone, cholest-8(14)-en-3-ol, 4,4-dimethyl-, (3,5)-, stigmast-4-en-3-one, stigmasterol, 1-ethyl-1-tetradecyloxy-1-silacyclohexane, ɣ-sitosterol, stigmast-7-en-3-ol, (3,5,24S)-, and -monostearin. molecular docking was carried out using the crystal structure -amylase (PDB ID: 4W93) and -glucosidase (PDB ID: 3WY1). -Amylase-n-hexadecanoic acid exhibited the lowest binding energy of -2.28 kcal/mol with two hydrogen bonds residue, namely, LYS178 and TYR174, along with hydrophobic interactions involving PRO140, TRP134, SER132, ASP135, and LYS172. The binding interactions of -glucosidase-n-hexadecanoic acid complex ligand also showed the lowest binding energy among 5 major compounds with the energy value of -4.04 kcal/mol. The complex consists of one hydrogen bond interacting residue, ARG437, and hydrophobic interactions with ALA444, ASP141, GLN438, GLU432, GLY374, LEU373, LEU433, LYS352, PRO347, THR445, HIS348, and PRO351. The study provides informative data on the potential antidiabetic inhibitors identified in twigs, indicating the plant has the therapeutic effect properties to manage diabetes.
Topics: Data Analysis; Gas Chromatography-Mass Spectrometry; Hypoglycemic Agents; Inhibitory Concentration 50; Least-Squares Analysis; Metabolome; Metabolomics; Molecular Docking Simulation; Multivariate Analysis; Plant Extracts; Principal Component Analysis; Rubiaceae; alpha-Amylases; alpha-Glucosidases
PubMed: 31275982
DOI: 10.1155/2019/7603125 -
Clinical Nutrition (Edinburgh, Scotland) Dec 2015Consumption of plant stanols and plant sterols decreases LDL cholesterol level and increases serum concentrations of plant stanols/sterols, but it is practically... (Randomized Controlled Trial)
Randomized Controlled Trial
BACKGROUND & AIMS
Consumption of plant stanols and plant sterols decreases LDL cholesterol level and increases serum concentrations of plant stanols/sterols, but it is practically unexplored whether also their tissue concentrations increase. Thus, the aim of this study was to assess whether consuming plant stanols/sterols increases their concentrations in stenotic aortic valves and affect the valvular structure (collagen and elastin) or inflammation (macrophages and mast cells).
METHODS
In a randomized, double-blind controlled intervention patients with severe aortic stenosis consumed margarine without (n = 11) or with 2 g of plant stanols (n = 12) or sterols (n = 13) until valve replacement surgery (2.6 months, on average). The effects of sitostanol and sitosterol on the expression and secretion of proinflammatory cytokines by cultured aortic valve myofibroblasts were also assessed.
RESULTS
Control-related LDL-cholesterol was diminished by 16% (p < 0.05) by plant stanol and by 11% (NS) by plant sterol consumption, respectively. In the resected valves, cholesterol, plant stanol and sterol levels were similar in all groups. Consumed plant stanols or sterols had no effect on valvular structure or mast cell or macrophage numbers in valves. Incubation of cultured myofibroblasts derived from stenotic valves with sitostanol or sitosterol decreased mRNA expression of the monocyte chemotactic protein-1 (p < 0.05) and interleukin-1 beta (p < 0.05).
CONCLUSIONS
In this study, plant stanol/sterol consumption did not affect cholesterol, plant stanol or sterol levels in stenotic aortic valves; neither did they influence the structure or the inflammatory status of the valves. However, these findings need to be confirmed in a larger-scale intervention. ClinicalTrials.govRegister #NCT00738933.
Topics: Aged; Aged, 80 and over; Aortic Valve; Chemokine CCL2; Cholesterol, LDL; Diet; Double-Blind Method; Female; Heart Valve Prosthesis Implantation; Humans; Interleukin-1beta; Male; Margarine; Middle Aged; Myofibroblasts; Phytosterols; RNA, Messenger; Sitosterols
PubMed: 25614126
DOI: 10.1016/j.clnu.2015.01.001 -
Langmuir : the ACS Journal of Surfaces... May 2016The solubility of cholesterol in bile salt (BS) micelles is important to understand the availability of cholesterol for absorption in the intestinal epithelium and to...
The solubility of cholesterol in bile salt (BS) micelles is important to understand the availability of cholesterol for absorption in the intestinal epithelium and to develop strategies to decrease cholesterol intake from the intestinal lumen. This has been the subject of intense investigation, due to the established relation between the development of diseases such as atherosclerosis and high levels of cholesterol in the blood. In this work we quantify the effect of BS variability on the amount of cholesterol solubilized. The effect of some known hypocholesterolemic agents usually found in the diet is also evaluated, as well as some insight regarding the mechanisms involved. The results show that, depending on the bile salt composition, the average value of sterol per micelle is equal to or lower than 1. The amount of cholesterol solubilized in the BS micelles is essentially equal to its total concentration until the solubility limit is reached. Altogether, this indicates that the maximum cholesterol solubility in the BS micellar solution is the result of saturation of the aqueous phase and depends on the partition coefficient of cholesterol between the aqueous phase and the micellar pseudophase. The effect on cholesterol maximum solubility for several food ingredients usually encountered in the diet was characterized using methodology developed recently by us. This method allows the simultaneous quantification of both cholesterol and food ingredient solubilized in the BS micelles even in the presence of larger aggregates, therefore avoiding their physical separation with possible impacts on the overall equilibrium. The phytosterols stigmasterol and stigmastanol significantly decreased cholesterol solubility with a concomitant reduction in the total amount of sterol solubilized, most pronounced for stigmasterol. Those results point toward coprecipitation being the major cause for the decrease in cholesterol solubilization by the BS micelles. The presence of tocopherol and oleic acid leads to a small decrease in the amount of cholesterol solubilized while palmitic acid slightly increases the solubility of cholesterol. Those dietary food ingredients are completely solubilized by the BS micelles, indicating that the effects on cholesterol solubility are due to changes in the properties of the mixed micelles.
Topics: Bile Acids and Salts; Cholesterol; Diet; Food Ingredients; Humans; Micelles; Phytosterols; Solubility
PubMed: 27079626
DOI: 10.1021/acs.langmuir.6b00723 -
Steroids Mar 2016Synthetic steryl ferulates [3-O-(trans-4-feruloyl)-sterols] are currently gaining considerable importance in recent years to be used as nutraceuticals and food additives... (Comparative Study)
Comparative Study
Microwave (MW) promoted high yield expedient synthesis of steryl ferulates--A class of novel biologically active compounds: A comparative study of their antioxidant activity with that of naturally occurring γ-oryzanol.
Synthetic steryl ferulates [3-O-(trans-4-feruloyl)-sterols] are currently gaining considerable importance in recent years to be used as nutraceuticals and food additives as well as in pharmaceutical applications substituting γ-oryzanol - a class of naturally occurring steryl ferulates having potent antioxidant and other organoleptic properties. Considering the importance of this class of compounds coupled with green technology associated with microwave energy (MW) in organic synthesis, we report here an expedited and high yield synthesis of steryl ferulates from abundant steroids, viz., cholesterol, cholestanol, stigmasterol, stigmastanol, β-sitosterol, β-campesterol, β-campestanol and ergosterol applying MW energy in the crucial step of esterification process of sterols with trans-4-O-acetylferulic acid to furnish their esterified products, viz., 3-O-(trans-4-O-acetylferuloyl)-sterols for their eventual deprotection to their respective steryl ferulates. We further report an efficient and scalable process of producing acetylferulic acid. Testing of synthesized steryl ferulates against antioxidant assays has also been highlighted.
Topics: Antioxidants; Coumaric Acids; Microwaves; Phenylpropionates; Sterols
PubMed: 26730721
DOI: 10.1016/j.steroids.2015.12.017 -
Journal of Agricultural and Food... Dec 2016A mixture of phytosterols/-stanols, consisting of 75% β-sitosterol, 12% sitostanol, 10% campesterol, 2% campestanol, and 1% others, was esterified with linoleic acid....
A mixture of phytosterols/-stanols, consisting of 75% β-sitosterol, 12% sitostanol, 10% campesterol, 2% campestanol, and 1% others, was esterified with linoleic acid. The resulting mixture of phytosteryl/-stanyl linoleates was subjected to thermal oxidation at 180 °C for 40 min. A silica solid-phase extraction was applied to separate a fraction containing the nonoxidized linoleates and nonpolar degradation products (heptanoates, octanoates) from polar oxidation products (oxo- and hydroxyalkanoates). In total, 15 sitosteryl, sitostanyl, and campesteryl esters, resulting from oxidation of the acyl chain, could be identified by GC-FID/MS. Synthetic routes were described for authentic reference compounds of phytosteryl/-stanyl 7-hydroxyheptanoates, 8-hydroxyoctanoates, 7-oxoheptanoates, 8-oxooctanoates, and 9-oxononanoates, which were characterized by GC-MS and two-dimensional NMR spectroscopy. The study provides data on the formation and identities of previously unreported classes of acyl chain oxidation products upon thermal treatment of phytosteryl/-stanyl fatty acid esters.
Topics: Cholesterol; Esters; Hot Temperature; Linoleic Acids; Molecular Structure; Oxidation-Reduction; Phytosterols; Sitosterols
PubMed: 27933991
DOI: 10.1021/acs.jafc.6b04326 -
Marine Pollution Bulletin Dec 2014In this study, the capacity of oysters to bioaccumulate fecal stanols and to record a source-specific fingerprint was investigated by the short-term contamination of...
In this study, the capacity of oysters to bioaccumulate fecal stanols and to record a source-specific fingerprint was investigated by the short-term contamination of seawater microcosms containing oysters with a human effluent. Contaminated oysters bioaccumulated the typical fecal stanols coprostanol and 24-ethylcoprostanol and their bioaccumulation kinetics were similar to that of the Fecal Indicator Bacteria Escherichia coli used in European legislation. Although stanol fingerprints of contaminated water allowed the identification of the human specific fingerprint, this was not the case for oysters. This discrepancy is attributed to (i) high concentrations of endogenous cholestanol and sitostanol, responsible for "unbalanced" stanol fingerprints, (ii) different accumulation/depuration kinetics of fecal coprostanol and 24-ethylcoprostanol and (iii) the limits of the analytical pathway used. These results show that fecal stanols bioaccumulated by oysters are useful to record fecal contamination but the usefulness of stanol fingerprints to identify specific sources of contamination in shellfish currently seems limited.
Topics: Animals; Cholestanol; Environmental Monitoring; Escherichia coli; Feces; Food Contamination; Humans; Ostreidae; Seawater; Shellfish; Sitosterols; Water Pollution
PubMed: 25455370
DOI: 10.1016/j.marpolbul.2014.10.037