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Drupes were handpicked from olive (Olea europaea L.) trees, cv chemlali, at 13 distinct stages of fruit development, referred to as weeks after flowering (WAF), and analyzed for their free and esterified sterols and triterpenoids content. These two classes of compounds are synthesized via the acetate/mevalonate pathway and share common precursors up to oxidosqualene (OS). Cyclization of OS in either...
The purpose of this review is to outline the emerging role of dietary phytosterols in human health. Dietary saturated fat, cholesterol and fiber are currently emphasized in the reduction of low-density lipoprotein cholesterol levels. However, other dietary components such as phytosterols may have equivalent or even larger effects on circulating cholesterol and need further study with respect to the...
Steroidal saponins are complex compounds that have a steroid attached to a carbohydrate moiety. They are natural surfactants and detergents and exhibit a number of biological effects. Steroidal saponins have shown membrane-permeabilizing, hypocholesterolemic, immunostimulant, and anticancer properties. They have also been found to affect the growth, food intake and reproductive capabilities of animals...
24S-hydroxycholesterol was identified more than half a century ago and was initially given the name “cerebrosterol” due to the fact that it was abundant in the brain. A decade ago, we showed that the most important mechanism by which cholesterol is eliminated from the mammalian brain involves a hydroxylation into cerebrosterol followed by diffusion of this steroid over the blood–brain barrier. Using...
Sterols, which are biosynthesized via the cytoplasmic mevalonate (MVA) pathway, are important structural components of the plasma membrane and precursors of steroid hormones in both vertebrates and plants. Ergosterol and cholesterol are the major sterols in yeast and vertebrates, respectively. In contrast, plants produce a wide variety of phytosterols, which have various functions in plant development...
In the Liebermann–Burchard (LB) colorimetric assay, treatment of cholesterol with sulfuric acid, acetic anhydride, and acetic acid elicits a blue color. We studied the reactivity of cholesterol under LB conditions and provide definitive NMR characterization for approximately 20 products, whose structure and distribution suggest the following mechanistic picture. The major reaction pathways do not...
Sterol biosynthesis inhibitors (SBIs), discovered in the late 1960s and subsequently used commercially to treat ergosterol-dependent fungal diseases, represent a unique drug class targeted at an enzyme in a biosynthetic pathway. To date, few drugs have been commercialized as enzyme inhibitors; yet, prescription of SBIs has emerged as the gold standard for some cases of non-life-threatening antifungal...
Oxygenated derivates of cholesterol and lanosterol, known as oxysterols, have consistently displayed significant activity as inhibitors of 3-hydroxy-3-methylglutaryl (HMG) CoA reductase, a key regulatory enzyme in sterol biosynthesis. We have developed the chemical syntheses of ring C oxysterols for evaluation as inhibitors of sterol biosynthesis. A key intermediate in the chemical synthesis was 3β-benzoyloxy-9α,...
ERG2 and ERG24 are yeast sterol biosynthetic genes which are targets of morpholine antifungal compounds. ERG2 and ERG24 encode the C-8 sterol isomerase and the C-14 reductase, respectively. ERG2 is regarded as a non-essential gene but the viability of ERG24 depends on genetic background, type of medium, and CaCl2 concentration. We demonstrate that erg2 and erg24 mutants are viable in the deletion...
Apolipoprotein (apoB) plays a fundamental role in the transport and metabolism of plasma triacylglycerols (TAGs) and cholesterol. Several apoB polymorphic sites have been studied for their potential use as markers for coronary heart disease in the population. In view of the importance of apoB in postprandial metabolism, our objective was to determine whether the presence of the -516C/T polymorphism...
Exogenous and endogenous cholesterol oxidation products (COPs) perturb various metabolic processes, and thereby they may induce various homeostasis-related disorders. Here, we observed that procyanidin-rich dietary apple polyphenol (APP) from unripe apples alleviates the perturbation of lipid metabolism by decreasing the exogenous COP levels in rats. Dietary COPs may be the greatest source of COPs...
In addition to being a very good antioxidant, γ-tocopherol is also an excellent electrophile trap. This is a study of the reactivity of γ-tocopherol with hypochlorous acid/hypochlorite, a potential biological foe that is both an oxidant and an electrophile. Aqueous sodium hypochlorite (1.72 mmol; pH 7.4) was stirred with γ-tocopherol (0.12 mmol) in hexane for 2 min at room temperature. The following...
Conjugated linoleic acids (CLAs) consist of a series of positional and geometrical isomers of linoleic acid. CLA have been reported to beneficially affect cardiovascular risk factors in animal models. In order to assess the role of individual CLA isomers on lipoprotein cholesterol concentration, 30 hamsters were fed for 12 weeks an hyperlipidic diet containing pure cis-9,trans-11 CLA (c9,t11) or pure...
The objective of the study was to evaluate potential benefits of docosahexaenoic acid (DHA) rich fish oil supplementation as an adjunct to statin therapy for hyperlipidaemia. A total of 45 hyperlipidaemic patients on stable statin therapy with persistent elevation of plasma triglycerides (averaging 2.2 mmol/L) were randomised to take 4 g/day (n = 15) or 8 g/day (n = 15) of tuna oil or olive oil (placebo,...
Within the visual system, docosahexaenoic acid (DHA, 22:6n−3) is an important structural component for retinal photoreceptors and cortical gray matter. There is a marked decrease in neural DHA accumulation in the face of DHA deficiency. DHA is accumulated at an accelerated rate during pregnancy, especially in the third trimester. However, pregnant women in the US and Canada have dietary DHA intakes...
Naturally occurring vitamin E, comprised of four forms each of tocopherols and tocotrienols, are synthesized solely by photosynthetic organisms and function primarily as antioxidants. These different forms vary in their biological availability and in their physiological and chemical activities. Tocopherols and tocotrienols play important roles in the oxidative stability of vegetable oils and in the...
The experiment was designed to study the effects of butters differing in conjugated linoleic acid (CLA) and trans 18:1 contents on lipoproteins associated with the risk of atherogenesis. New Zealand White male rabbits (9.6 weeks; 2.1 kg) were assigned for 6 or 12 weeks to three diets (n = 6 per diet) made of conventional pellets with 0.2% cholesterol and with 12% fat provided from a butter poor in...
To elucidate the transepithelial transport characteristics of lipophilic compounds, the cellular uptake of tocopherol and tocotrienol isomers were investigated in Caco2 cell monolayer models. These vitamin E isomers formed mixed micelles consisting of bile salts, lysophospholipids, free fatty acid, and 2-monoacylglycerols, then the micelles were supplied to Caco2 cells. The initial accumulation of...
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