Jump to content
 







Main menu
   


Navigation  



Main page
Contents
Current events
Random article
About Wikipedia
Contact us
Donate
 




Contribute  



Help
Learn to edit
Community portal
Recent changes
Upload file
 








Search  



























Create account

Log in
 









Create account
 Log in
 




Pages for logged out editors learn more  



Contributions
Talk
 



















Contents

   



(Top)
 


1Types
 


1.1Phytosterols
 




1.2Zoosterols
 




1.3Mycosterols
 






2Role in biochemistry
 


2.1Phytosterols as a nutritional supplement
 






3Chemical classification and structure
 




4See also
 




5References
 




6Further reading
 




7External links
 













Sterol






Afrikaans
العربية

Беларуская
Bosanski
Català
Čeština
Dansk
Deutsch
Ελληνικά
Español
Esperanto
Euskara
فارسی
Français
Galego

Հայերեն
ि
Bahasa Indonesia
Italiano
עברית
Қазақша
Magyar
Македонски
Bahasa Melayu
Nederlands

Norsk bokmål
Norsk nynorsk
Polski
Português
Română
Русский
Slovenščina
Српски / srpski
Srpskohrvatski / српскохрватски
Suomi
Svenska

Türkçe
Українська
Tiếng Vit



 

Edit links
 









Article
Talk
 

















Read
Edit
View history
 








Tools
   


Actions  



Read
Edit
View history
 




General  



What links here
Related changes
Upload file
Special pages
Permanent link
Page information
Cite this page
Get shortened URL
Download QR code
Wikidata item
 




Print/export  



Download as PDF
Printable version
 




In other projects  



Wikimedia Commons
 


















From Wikipedia, the free encyclopedia
 


Sterol
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

PubChem CID

  • 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

Chemical formula

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

Sterol is an organic compound[1] with formula C
17
H
28
O
, whose molecule is derived from that of gonane by replacement of a hydrogen atom on C3 position 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).[2][3] 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.

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

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

Types[edit]

Phytosterols[edit]

Phytosterols are sterols naturally found in plants. Notable examples of phytosterols include campesterol, sitosterol, and stigmasterol.

Zoosterols[edit]

Zoosterols are sterols found in animals. The most significant zoosterol is cholesterol.

Mycosterols[edit]

Sterols found in fungi are called mycosterols. A common example is ergosterol, a mycosterol present in the cell membrane of fungi, where it serves a role similar to cholesterol in animal cells.

Role in biochemistry[edit]

Sterols and related compounds play essential roles in the physiology of eukaryotic organisms, and are essential for normal physiology of plants, animals, and fungi.[4] 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.[5]

Phytosterols as a nutritional supplement[edit]

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.[6] 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.[7] Preliminary research has shown that phytosterols may have anticancer effects.[8]

Chemical classification and structure[edit]

Sterols are a subgroup of steroids with a hydroxyl group at the 3-position of the A-ring.[9] 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[edit]

References[edit]

  1. ^ "sterol (CHEBI:15889)". www.ebi.ac.uk. Retrieved 2023-11-04.
  • ^ 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. Bibcode:2021PNAS..11801276H. doi:10.1073/pnas.2101276118. PMC 8237579. PMID 34131078.
  • ^ Luo, Jie; Yang, Hongyuan; Song, Bao-Liang (April 2020). "Mechanisms and regulation of cholesterol homeostasis". Nature Reviews Molecular Cell Biology. 21 (4): 225–245. doi:10.1038/s41580-019-0190-7. ISSN 1471-0080. PMID 31848472. S2CID 209392321.
  • ^ 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 & 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[edit]

    • Alberts B (2002). "10. Membrane Structure" (Online at NIH). Molecular biology of the cell. Vol. 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

    External links[edit]


    Retrieved from "https://en.wikipedia.org/w/index.php?title=Sterol&oldid=1212926843"

    Category: 
    Sterols
    Hidden categories: 
    Chemical articles without CAS registry number
    Articles without EBI source
    Articles without UNII source
    Articles containing unverified chemical infoboxes
    Articles with short description
    Short description is different from Wikidata
    Articles to be expanded from May 2023
    All articles to be expanded
    Articles using small message boxes
    CS1: long volume value
    Webarchive template wayback links
    Articles with BNF identifiers
    Articles with BNFdata identifiers
    Articles with GND identifiers
    Articles with J9U identifiers
    Articles with LCCN identifiers
    Articles with NDL identifiers
    Articles with NKC identifiers
     



    This page was last edited on 10 March 2024, at 06:47 (UTC).

    Text is available under the Creative Commons Attribution-ShareAlike License 4.0; additional terms may apply. By using this site, you agree to the Terms of Use and Privacy Policy. Wikipedia® is a registered trademark of the Wikimedia Foundation, Inc., a non-profit organization.



    Privacy policy

    About Wikipedia

    Disclaimers

    Contact Wikipedia

    Code of Conduct

    Developers

    Statistics

    Cookie statement

    Mobile view



    Wikimedia Foundation
    Powered by MediaWiki