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Sterol

Sterol is an organic compound with formulaC
17
H
28
O
, whose molecule is derived from that of gonane by replacement of a hydrogen atom in position 3 by a hydroxyl group. It is therefore an alcohol of gonane. More generally, any compounds that contain the gonane structure, additional functional groups, and/or modified ring systems derived from gonane are called steroids. Therefore, sterols are a subgroup of the steroids. They occur naturally in most eukaryotes, including plants, animals, and fungi, and can also be produced by some bacteria (however likely with different functions). The most familiar type of animal sterol is cholesterol, which is vital to cell membrane structure, and functions as a precursor to fat-soluble vitamins and steroid hormones.

Sterol
Names
IUPAC name
2,3,4,5,6,7,8,9,10,11,12,13,14,15,16,17-hexadecahydro-1H-cyclopenta[a]phenanthren-3-ol
Other names
Hexadecahydro-3H-cyclopenta[a]phenanthrene-3-ol
Identifiers
3D model (JSmol)
ChemSpider
KEGG
  • InChI=1S/C17H28O/c18-13-6-9-15-12(10-13)5-8-16-14-3-1-2-11(14)4-7-17(15)16/h11-18H,1-10H2
    Key: FPXSXMFOYWRHDX-UHFFFAOYSA-N
  • C1CC2CCC3C4CCC(CC4CCC3C2C1)O
Properties
C17H28O
Molar mass 248.410 g·mol−1
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
Infobox references

While technically alcohols, sterols are classified by biochemists as lipids (fats in the broader sense of the term).

The gonane skeleton, with the IUPAC recommended numbering of the carbon atoms

Contents

Sterols of plants are called phytosterols and sterols of animals are called zoosterols. The most important zoosterol is cholesterol; notable phytosterols include campesterol, sitosterol, and stigmasterol. Ergosterol is a sterol present in the cell membrane of fungi, where it serves a role similar to cholesterol in animal cells.

Sterols and related compounds play essential roles in the physiology of eukaryotic organisms. For example, cholesterol forms part of the cellular membrane in animals, where it affects the cell membrane's fluidity and serves as secondary messenger in developmental signaling. In humans and other animals, corticosteroids such as cortisol act as signaling compounds in cellular communication and general metabolism. Sterols are common components of human skin oils.

Phytosterols as a nutritional supplement

Main article: Phytosterol

Phytosterols, more commonly known as plant sterols, have been shown in clinical trials to block cholesterol absorption sites in the human intestine, thus helping to reduce cholesterol absorption in humans. They are currently approved by the U.S. Food and Drug Administration for use as a food supplement; however, there is some concern that they may block absorption not only of cholesterol, but of other important nutrients as well. At present, the American Heart Association has recommended that supplemental plant sterols be taken only by those diagnosed with elevated cholesterol, and has particularly recommended that they not be taken by pregnant women or nursing mothers. Preliminary research has shown that phytosterols may have anticancer effects.

Sterols are a subgroup of steroids with a hydroxyl group at the 3-position of the A-ring. They are amphipathic lipids synthesized from acetyl-coenzyme A via the HMG-CoA reductase pathway. The overall molecule is quite flat. The hydroxyl group on the A ring is polar. The rest of the aliphatic chain is non-polar.

  1. Wei JH, Yin X, Welander PV (24 June 2016). "Sterol Synthesis in Diverse Bacteria". Frontiers in Microbiology. 7: 990. doi:10.3389/fmicb.2016.00990. PMC4919349. PMID 27446030.
  2. Hoshino Y, Gaucher EA (June 2021). "Evolution of bacterial steroid biosynthesis and its impact on eukaryogenesis". Proceedings of the National Academy of Sciences of the United States of America. 118 (25): e2101276118. doi:10.1073/pnas.2101276118. PMC8237579. PMID 34131078.
  3. Lampe MA, Burlingame AL, Whitney J, Williams ML, Brown BE, Roitman E, Elias PM (February 1983). "Human stratum corneum lipids: characterization and regional variations". Journal of Lipid Research. 24 (2): 120–30. doi:10.1016/S0022-2275(20)38005-6. PMID 6833889.
  4. Ostlund RE, Racette SB, Stenson WF (June 2003). "Inhibition of cholesterol absorption by phytosterol-replete wheat germ compared with phytosterol-depleted wheat germ". The American Journal of Clinical Nutrition. 77 (6): 1385–9. doi:10.1093/ajcn/77.6.1385. PMID 12791614.
  5. "Do we need to be buying plant sterols?"(PDF). Food Magazine. 67: 14. October–December 2004. Archived from the original(PDF) on 15 September 2007. Retrieved8 August 2008.
  6. Bradford PG, Awad AB (February 2007). "Phytosterols as anticancer compounds". Molecular Nutrition & Food Research. 51 (2): 161–70. doi:10.1002/mnfr.200600164. PMID 17266177.
  7. Fahy E, Subramaniam S, Brown HA, Glass CK, Merrill AH, Murphy RC, et al. (May 2005). "A comprehensive classification system for lipids". Journal of Lipid Research. 46 (5): 839–61. doi:10.1194/jlr.E400004-JLR200. PMID 15722563.
  • Alberts B (2002). "10. Membrane Structure"(Online at NIH). Molecular biology of the cell. IV. Internal Organization of the Cell. New York: Garland Science. p. 1874. ISBN 978-0-8153-4072-0. The Fluidity of a Lipid Bilayer Depends on Its Composition

Sterol
Sterol Article Talk Language Watch Edit 160 160 Redirected from Sterols Sterol is an organic compound with formula C17 H28 O whose molecule is derived from that of gonane by replacement of a hydrogen atom in position 3 by a hydroxyl group It is therefore an alcohol of gonane More generally any compounds that contain the gonane structure additional functional groups and or modified ring systems derived from gonane are called steroids Therefore sterols are a subgroup of the steroids They occur naturally in most eukaryotes including plants animals and fungi and can also be produced by some bacteria however likely with different functions 1 2 The most familiar type of animal sterol is cholesterol which is vital to cell membrane structure and functions as a precursor to fat soluble vitamins and steroid hormones Sterol NamesIUPAC name 2 3 4 5 6 7 8 9 10 11 12 13 14 15 16 17 hexadecahydro 1H cyclopenta a phenanthren 3 olOther names Hexadecahydro 3H cyclopenta a phenanthrene 3 olIdentifiers3D model JSmol Interactive imageChemSpider 1076KEGG C00370PubChem CID 1107InChI InChI 1S C17H28O c18 13 6 9 15 12 10 13 5 8 16 14 3 1 2 11 14 4 7 17 15 16 h11 18H 1 10H2Key FPXSXMFOYWRHDX UHFFFAOYSA NSMILES C1CC2CCC3C4CCC CC4CCC3C2C1 OPropertiesChemical formula C 17H 28OMolar mass 248 410 g mol 1Except where otherwise noted data are given for materials in their standard state at 25 C 77 F 100 kPa Infobox references While technically alcohols sterols are classified by biochemists as lipids fats in the broader sense of the term The gonane skeleton with the IUPAC recommended numbering of the carbon atoms Contents 1 Types 2 Role in biochemistry 2 1 Phytosterols as a nutritional supplement 3 Chemical classification and structure 4 See also 5 References 6 Further reading 7 External linksTypes EditSterols of plants are called phytosterols and sterols of animals are called zoosterols The most important zoosterol is cholesterol notable phytosterols include campesterol sitosterol and stigmasterol Ergosterol is a sterol present in the cell membrane of fungi where it serves a role similar to cholesterol in animal cells Role in biochemistry EditSterols and related compounds play essential roles in the physiology of eukaryotic organisms For example cholesterol forms part of the cellular membrane in animals where it affects the cell membrane s fluidity and serves as secondary messenger in developmental signaling In humans and other animals corticosteroids such as cortisol act as signaling compounds in cellular communication and general metabolism Sterols are common components of human skin oils 3 Phytosterols as a nutritional supplement Edit Main article Phytosterol Phytosterols more commonly known as plant sterols have been shown in clinical trials to block cholesterol absorption sites in the human intestine thus helping to reduce cholesterol absorption in humans 4 They are currently approved by the U S Food and Drug Administration for use as a food supplement however there is some concern that they may block absorption not only of cholesterol but of other important nutrients as well At present the American Heart Association has recommended that supplemental plant sterols be taken only by those diagnosed with elevated cholesterol and has particularly recommended that they not be taken by pregnant women or nursing mothers 5 Preliminary research has shown that phytosterols may have anticancer effects 6 Chemical classification and structure EditSterols are a subgroup of steroids with a hydroxyl group at the 3 position of the A ring 7 They are amphipathic lipids synthesized from acetyl coenzyme A via the HMG CoA reductase pathway The overall molecule is quite flat The hydroxyl group on the A ring is polar The rest of the aliphatic chain is non polar See also EditCholesterol Ergosterol Hopanoids Hydroxysteroid Phytosterol Steroids ZoosterolReferences Edit Wei JH Yin X Welander PV 24 June 2016 Sterol Synthesis in Diverse Bacteria Frontiers in Microbiology 7 990 doi 10 3389 fmicb 2016 00990 PMC 4919349 PMID 27446030 Hoshino Y Gaucher EA June 2021 Evolution of bacterial steroid biosynthesis and its impact on eukaryogenesis Proceedings of the National Academy of Sciences of the United States of America 118 25 e2101276118 doi 10 1073 pnas 2101276118 PMC 8237579 PMID 34131078 Lampe MA Burlingame AL Whitney J Williams ML Brown BE Roitman E Elias PM February 1983 Human stratum corneum lipids characterization and regional variations Journal of Lipid Research 24 2 120 30 doi 10 1016 S0022 2275 20 38005 6 PMID 6833889 Ostlund RE Racette SB Stenson WF June 2003 Inhibition of cholesterol absorption by phytosterol replete wheat germ compared with phytosterol depleted wheat germ The American Journal of Clinical Nutrition 77 6 1385 9 doi 10 1093 ajcn 77 6 1385 PMID 12791614 Do we need to be buying plant sterols PDF Food Magazine 67 14 October December 2004 Archived from the original PDF on 15 September 2007 Retrieved 8 August 2008 Bradford PG Awad AB February 2007 Phytosterols as anticancer compounds Molecular Nutrition amp Food Research 51 2 161 70 doi 10 1002 mnfr 200600164 PMID 17266177 Fahy E Subramaniam S Brown HA Glass CK Merrill AH Murphy RC et al May 2005 A comprehensive classification system for lipids Journal of Lipid Research 46 5 839 61 doi 10 1194 jlr E400004 JLR200 PMID 15722563 Further reading EditAlberts B 2002 10 Membrane Structure Online at NIH Molecular biology of the cell IV Internal Organization of the Cell New York Garland Science p 1874 ISBN 978 0 8153 4072 0 The Fluidity of a Lipid Bilayer Depends on Its CompositionExternal links EditSterols Cyberlipid org Retrieved from https en wikipedia org w index php title Sterol amp oldid 1045600475, wikipedia, wiki, book,

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