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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: In this article, the synthesis of lanosterol and desmosterol labeled with 14C in the 25 position by a Wittig reaction between triphenyl-2 14C isopropylidene-phosphorane [IVb] and corresponding aldehydes is described.
Abstract: The synthesis of lanosterol [Ia] and desmosterol [IIa] labeled with 14C in the 25 position by a Wittig reaction between triphenyl-2 14C isopropylidene-phosphorane [IVb] and the corresponding aldehydes are described. The specific activities obtained are, respectively, 0.539 mC/mM and 0.752 mC/mM and the purities of the compounds, respectively, 96 and 99%.

6 citations

Journal ArticleDOI
TL;DR: In this article, the second-order Beckmann cleavage of 3-hydroxyimino-5α-lanostane was used as an intermediate in the conversion of lanosterol into 14α-methylcholest-4-en-3-one.
Abstract: 3,4-Seco-5α-lanost-4(30)-en-3-onitrile, obtained by ‘second-order’ Beckmann cleavage of 3-hydroxyimino-5α-lanostane, has been used as an intermediate in the conversion of lanosterol into 14α-methylcholest-4-en-3-one.

6 citations

Journal ArticleDOI
TL;DR: It appears therefore, that the squalene which escapes incorporation into cholesterol is degraded to metabolite(s) suited for the synthesis of isoprene compounds.
Abstract: (1) Radioactivity of biosynthetically labeled squalene, injected in tracer amounts in rats is incorporated to about equal parts into cholesterol and component(s) of the fatty acid fraction of the liver. The ubiquinones isolated from the liver are radioactive and show about the same specific radioactivity as the cholesterol. It appears therefore, that the squalene which escapes incorporation into cholesterol is degraded to metabolite(s) suited for the synthesis of isoprene compounds. (2) Radioactivity of injected biosynthetically and chemically labeled cholesterol is traced in the ubiquinones and the squalene of rat liver indicating that a degradation of cholesterol and a recycling of the metabolite(s) occurs. (3) A recycling of metabolite(s) of squalene and of cholesterol can explain the observation that after labeled mevalonate or acetate as precursor, radioactivity can be traced in the squalene of the liver many hours after the injection and maintains a constant value during a period of several hours. (4) Radioactivity of biosynthetically labeled lanosterol is not only incorporated into cholesterol but a considerable part of it into component(s) of the bile acid fraction of the liver. Evidence is obtained that this transformation occurs by circumventing cholesterol as intermediate.

6 citations

Journal ArticleDOI
TL;DR: In this article, the structure of the major metabolites of 7,11-dioxodihydrolanosterol has been determined using 2D-NMR and showed that the tetracyclic skeleton can undergo regioselective oxidation-reduction modifications at the 3 and 7 positions.
Abstract: While mycobacteria are unable to degrade lanosterol and dihydrolanosterol, principal components of wool fat, we observed the transformation of some of their autoxidation products by Mycobacterium phlei. By analogy with the mechanism of degradation of cholesterol, this difference was assumed to be due to the requirement for the presence of an enone group before the side-chain can be degraded. This paper reports the spectroscopic determination of the structure of the major metabolites of 7,11-dioxodihydrolanosterol. The side-chain is degraded from eight carbon atoms to three, the terminal carbon atom being oxidized to a primary alcohol or a methyl ester. The tetracyclic skeleton can undergo regioselective oxidation–reduction modifications at the 3- and 7-position. Their conformational analysis, carried out by 2D-NMR methods, indicates a chair form for ring A of 3β-hydroxy derivatives, while it is highly deformed for 3-keto compounds as predicted formerly by Mislow for this lanostane series.

6 citations


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