ChemInform Abstract: Total Synthesis of the Squalene Synthase Inhibitor Zaragozic Acid C.
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Abstract ChemInform is a weekly Abstracting Service, delivering concise information at a glance that was extracted from about 100 leading journals. To access a ChemInform Abstract of an article which was published elsewhere, please select a “Full Text” option. The original article is trackable via the “References” option.Keywords:
Squalene
In triparanol-inhibited cultures of T. pyriformis (strains W, H and S), squalene is greatly increased in amount and tetra-hymanol is decreased. In contrast, squalene appears in low concentration in uninhibited cultures. It appears that squalene might be converted directly to the pentacyclic compound, tetrahymanol, and that the cyclization of squalene is blocked by triparanol. Cholesterol was not identified in control or inhibited cultures and appears neither to be a sterol of major importance in this organism, nor an intermediate in the synthesis of tetrahymanol. Methods of purification and identification of tetrahymanol are given.
Squalene
Tetrahymena pyriformis
Squalene monooxygenase
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Five subjects consumed a meal containing ca. 1.5 mg squalene. Postprandial serum samples showed that in three of the subjects squalene and lipid levels reached maxima at 3 hr. Squalene levels in the low density lipoproteins of these subjects also increased. The results indicate that alimentation is a major factor in the variation in serum squalene levels.
Squalene
Lipidology
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Squalene
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Evonik Industries has launched amaranth oil–derived squalene as an alternative to squalene extracted from shark-liver oil . Squalene is used as an adjuvant to boost vaccine efficiency. Evonik calls its product the first adjuvant-grade squalene to be derived from amaranth, an herbaceous plant cultivated in many parts of the world. Squalene is also extracted from olive oil by the French company Sophim and produced via fermentation by the US firm Amyris.
Squalene
Herbaceous plant
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The sources and applications of the bioactive substance squalen that widely exists in animals and plants are reviewed.According to the citations,the most abundant sources of squalene in animals are deep-sea fishes,especially sharks,in which the highest content of squalene is approached to 69% based on liver oil.Amaranth seed oil,olive oil and palm oil are the major plant sources of squalene.The content of squalene is 5 %-8% in amaranth seed oil,and the highest content is 1.16% in olive oil.Because of the strong bioactivity,squalene is widely used in medical care fields and in cosmetics.Squalene is easy to oxidize,so it must be kept with suitable antioxidant during storage.
Squalene
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Abstract Squalene is a terpenoid found in human skin surface lipids (SSLs) and foods that possesses beneficial properties. However, since oxidation of squalene causes various complications, it is necessary to identify the mechanisms by which squalene is oxidized. In this study, we aimed to determine the oxidation mechanisms of squalene in SSLs and shark liver oil (SLO) supplements by the analysis of squalene monohydroperoxide (SQOOH) isomers, on the basis of our previous finding that different oxidation mechanisms yield different SQOOH isomers. Liquid chromatography–tandem mass spectrometry analysis of SQOOH isomers revealed that squalene in human SSLs was oxidized by singlet oxygen oxidation, whereas squalene in SLO was oxidized mainly by free radicals. As a result, we have presented the first evidence suggesting that the analysis of SQOOH isomers enables estimation of oxidation mechanisms. Estimating oxidation mechanisms by analyzing SQOOH isomers may provide a foundation for the prevention of skin diseases and food deterioration via regulation of squalene oxidation.
Squalene
Terpene
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Squalene
Basal (medicine)
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Squalene is a triterpene that is an intermediate of the cholesterol biosynthesis pathway and it can be obtained from the diet. Olive oil contains 0.2 - 0.7% squalene. The average intake of squalene is 30 mg/day in the United States, however, when consumption of olive oil is high, the intake of squalene can reach 200 - 400 mg/day as observed in Mediterranean countries. The decreased risk for various cancers associated with high olive oil consumption may be due to the presence of squalene. Experimental studies have shown that squalene can effectively inhibit chemically-induced colon, lung and skin tumourigenesis in rodents. The protective effect is observed when squalene is given before and/or during carcinogen treatment. The mechanisms involved for the chemopreventive activity of squalene may include inhibition of Ras farnesylation, modulation of carcinogen activation and anti-oxidative activities. However, several factors must be taken into consideration when the evidence for the inhibition of carcinogenesis by squalene is examined, these include the effective dose used and the time of exposure. The information obtained is from animal bioassays and the long-term effects from consuming increased levels of squalene are not known. Although animal studies have enhanced our understanding of the possible action of squalene in decreasing carcinogenesis, one must apply caution in extrapolating the information obtained in animal studies to humans, because of possible species differences. In order to evaluate the overall implications of squalene to human cancer prevention, further studies are needed to fully identify its protective effects, as well as possible detrimental effects.
Squalene
Squalene monooxygenase
Farnesyl-diphosphate farnesyltransferase
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Squalene
Isopropyl myristate
Squalene monooxygenase
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Squalene
Refining (metallurgy)
Vegetable oil
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