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Lanosterol

About: Lanosterol is a research topic. Over the lifetime, 1239 publications have been published within this topic receiving 36737 citations. The topic is also known as: (3β)-lanosta-8,24-dien-3-ol & (3β,20R)-lanosta-8,24-dien-3-ol.


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Journal ArticleDOI
TL;DR: P perturbation of the production and localization of these components by terconazole is likely to contribute to the selective toxicity of this compound for C. albicans and other fungi.

22 citations

Journal ArticleDOI
TL;DR: Some mechanisms in the formation of cholesterol and its sterol precursors from lanosterol are discussed and the relation between in vitro and in vivo pathways of cholesterol biosynthesis and the composition and metabolism of sterols in biological tissues is underlined.
Abstract: The conversion of lanosterol║to cholesterol requires a considerable number of intermediary steps involving loss or uptake of hydrogen atoms and formation and migration of nuclear double bonds. Detailed discussions on the intermediary steps in cholesterol biosynthesis are reported in several reviews (Olson 1965; Frantz & Schroepfer 1967; Goad 1970). In the present report some mechanisms in the formation of cholesterol and its sterol precursors from lanosterol are discussed. The relation between in vitro and in vivo pathways of cholesterol biosynthesis and the composition and metabolism of sterols in biological tissues is underlined.

22 citations

Journal ArticleDOI
TL;DR: The formation of lipid electrophile-protein adducts is associated with many disorders that involve perturbations of cellular redox status and an increased understanding of these factors may help to define the pathogenesis of various human disorders involving oxidative stress.
Abstract: The formation of lipid electrophile-protein adducts is associated with many disorders that involve perturbations of cellular redox status. The identities of adducted proteins and the effects of adduction on protein function are mostly unknown and an increased understanding of these factors may help to define the pathogenesis of various human disorders involving oxidative stress. 7-Dehydrocholesterol (7-DHC), the immediate biosynthetic precursor to cholesterol, is highly oxidizable and gives electrophilic oxysterols that adduct proteins readily, a sequence of events proposed to occur in Smith-Lemli-Opitz syndrome (SLOS), a human disorder resulting from an error in cholesterol biosynthesis. Alkynyl lanosterol (a-Lan) was synthesized and studied in Neuro2a cells, Dhcr7-deficient Neuro2a cells and human fibroblasts. When incubated in control Neuro2a cells and control human fibroblasts, a-Lan completed the sequence of steps involved in cholesterol biosynthesis and alkynyl-cholesterol (a-Chol) was the major product formed. In Dhcr7-deficient Neuro2a cells or fibroblasts from SLOS patients, the biosynthetic transformation was interrupted at the penultimate step and alkynyl-7-DHC (a-7-DHC) was the major product formed. When a-Lan was incubated in Dhcr7-deficient Neuro2a cells and the alkynyl tag was used to ligate a biotin group to alkyne-containing products, protein-sterol adducts were isolated and identified. In parallel experiments with a-Lan and a-7-DHC in Dhcr7-deficient Neuro2a cells, a-7-DHC was found to adduct to a larger set of proteins (799) than a-Lan (457) with most of the a-Lan protein adducts (423) being common to the larger a-7-DHC set. Of the 423 proteins found common to both experiments, those formed from a-7-DHC were more highly enriched compared to a DMSO control than were those derived from a-Lan. The 423 common proteins were ranked according to the enrichment determined for each protein in the a-Lan and a-7-DHC experiments and there was a very strong correlation of protein ranks for the adducts formed in the parallel experiments.

21 citations

Journal ArticleDOI
TL;DR: In this article, the electrochemical reduction of the heme protein sterol-14alpha-demethylase from Mycobacterium tuberculosis (CYP51b1), or further CYP51, was investigated.
Abstract: The electrochemical reduction of the heme protein sterol-14alpha-demethylase from Mycobacterium tuberculosis (CYP51b1, or further CYP51) was investigated. Direct electron transfer was demonstrated between CYP51 and graphite screen-printed electrodes modified with gold nanoparticles and with the membrane-like synthetic surfactant didodecyl dimethylammonium bromide. The formal potential of the Fe3+/Fe2+ pair, E(1/2), is equal to -273 mV (vs. Ag/AgCl). The cathodic current corresponding to the reduction of oxygen by immobilized heme protein was registered in the presence of oxygen. Addition of lanosterol, one of the substrates of the CYP51 family, to the oxygenated solution caused a concentration-dependent increase in the reduction current in voltammetric and amperometric experiments. Ketoconazole, an inhibitor of CYP51, inhibited the catalytic cathodic current in the presence of lanosterol. Electrochemical reduction of CYP51 may serve as an adequate alternative to the reconstituted system, which requires additional redox partners for the exhibition of catalytic activity of heme proteins of the cytochrome P450 superfamily.

21 citations

Book ChapterDOI
01 Jan 1990
TL;DR: The sterol biosynthesis pathway in plants has been extensively investigated and rewieved in detail recently and three enzymatic reactions are of interest both for their intricate mechanisms and as phylogenetic markers in higher plants.
Abstract: Cholesterol (1) is the major sterol in vertebrates and ergosterol (2) in fungi whereas plant cells contain a mixture of C-24-alkylated sterols, mainly campesterol (3), stigmasterol (4) and sitosterol (5). The sterol biosynthesis pathway in plants has been extensively investigated and rewieved in detail recently (Benveniste 1986). After a biosynthetic pathway from acetate to 2,3-oxidosqualene, common to animals, fungi and vascular plants, sterol biosynthesis differs in these three classes of organisms (Fig. 1): First: 2(3)-oxidosqualene (6) cyclases produce lanosterol (7) in non-photosynthetic eukaryotic organisms (animals, fungi), whereas they yield cycloartenol (8), the 9β,19-cyclopropyl isomer of (7) in photosynthetic eukaryotes (algae, higher plants) (Fig. 1); second, this 9β,19-cyclopropane ring is cleaved by an enzyme specific to photosynthetic eukaryotes, namely cycloeucalenol (9)-obtusifoliol (10)-isomerase (COI); third, most higher plants contain two C-methyl-transferases responsible for the introduction of the two extra carbon atoms at C-24 in the plants sterols side chain. These three enzymatic reactions are of interest both for their intricate mechanisms and as phylogenetic markers in higher plants.

21 citations


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Performance
Metrics
No. of papers in the topic in previous years
YearPapers
202331
202261
202120
202023
201914
201822