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词条 Short-chain fatty acid
释义

  1. List of SCFAs

  2. Functions

  3. See also

  4. References

  5. Further reading

Short-chain fatty acids (SCFAs), also referred to as volatile fatty acids (VFAs),[1] are fatty acids with less than six carbon atoms.[2] Free SCFAs can cross the blood-brain barrier via monocarboxylate transporters.[3][4]

List of SCFAs

Lipid numberNameSalt/Ester NameFormulaMass
(g/mol)		Diagram
Common Systematic Common Systematic Molecular Structural
C1:0 Formic acid Methanoic acid Formate MethanoateC2|O|2} HCOOH 46.03
C2:0 Acetic acid Ethanoic acid Acetate EthanoateC|2|H|4|O|2}} CH3COOH 60.05
C3:0 Propionic acid Propanoic acid Propionate PropanoateC|3|H|6|O|2}} CH3CH2COOH 74.08
C4:0 Butyric acid Butanoic acid Butyrate ButanoateC|4|H|8|O|2}} CH3(CH2)2COOH 88.11
C4:0 Isobutyric acid 2-Methylpropanoic acid Isobutyrate 2-MethylpropanoateC|4|H|8|O|2}} (CH3)2CHCOOH 88.11
C5:0 Valeric acid Pentanoic acid Valerate PentanoateC|5|H|10|O|2}} CH3(CH2)3COOH 102.13
C5:0 Isovaleric acid 3-Methylbutanoic acid Isovalerate 3-MethylbutanoateC|5|H|10|O|2}} (CH3)2CHCH2COOH 102.13

Functions

SCFAs are produced when dietary fiber is fermented in the colon.[5] Acetate, propionate, and butyrate are the three most common SCFAs.

SCFAs and medium-chain fatty acids are primarily absorbed through the portal vein during lipid digestion,[6] while long-chain fatty acids are packed into chylomicrons and enter lymphatic capillaries, and enter the blood first at the subclavian vein.

SCFAs have diverse physiological roles in body functions. They can affect the production of lipids, energy and vitamins.[7] Up to 10% of the body's energy can come from SCFAs. Butyrate is particularly important for colon health because it is the primary energy source for colonic epithelial cells. The liver can use acetate for energy.[8][9]

See also

  • List of carboxylic acids
  • Medium-chain fatty acid (MCFA), fatty acid with aliphatic tails of 6 to 12 carbons, which can form medium-chain triglycerides
  • Long-chain fatty acid (LCFA, fatty acid with aliphatic tails of 13 to 21 carbons
  • Very long chain fatty acid (VLCFA), fatty acid with aliphatic tails of 22 or more carbons

References

1. ^"Role of Volatile Fatty Acids in Development of the Cecal Microflora in Broiler Chickens during Growth" at asm.org
2. ^{{cite book|last=Brody|first=Tom|title=Nutritional Biochemistry|year=1999|publisher=Academic Press|isbn=978-0121348366|url=https://books.google.com/books?id=n2fgyhDUaTEC&pg=PA320|edition=2nd|accessdate=December 21, 2012|page=320}}
3. ^{{cite journal | vauthors = Tsuji A | title = Small molecular drug transfer across the blood-brain barrier via carrier-mediated transport systems | journal = NeuroRx | volume = 2 | issue = 1 | pages = 54–62 | year = 2005 | pmid = 15717057 | pmc = 539320 | doi = 10.1602/neurorx.2.1.54 | quote = Uptake of valproic acid was reduced in the presence of medium-chain fatty acids such as hexanoate, octanoate, and decanoate, but not propionate or butyrate, indicating that valproic acid is taken up into the brain via a transport system for medium-chain fatty acids, not short-chain fatty acids. ... Based on these reports, valproic acid is thought to be transported bidirectionally between blood and brain across the BBB via two distinct mechanisms, monocarboxylic acid-sensitive and medium-chain fatty acid-sensitive transporters, for efflux and uptake, respectively.}}
4. ^{{cite journal | vauthors = Vijay N, Morris ME | title = Role of monocarboxylate transporters in drug delivery to the brain | journal = Curr. Pharm. Des. | volume = 20 | issue = 10 | pages = 1487–98 | year = 2014 | pmid = 23789956 | pmc = 4084603 | doi = 10.2174/13816128113199990462| quote = Monocarboxylate transporters (MCTs) are known to mediate the transport of short chain monocarboxylates such as lactate, pyruvate and butyrate. ... MCT1 and MCT4 have also been associated with the transport of short chain fatty acids such as acetate and formate which are then metabolized in the astrocytes [78].}}
5. ^{{cite journal|doi=10.1097/00004836-200603000-00015|pmid=16633129|year=2006|author1=Wong|first1=J. M.|title=Colonic health: Fermentation and short chain fatty acids|journal=Journal of Clinical Gastroenterology|volume=40|issue=3|pages=235–43|last2=De Souza|first2=R|last3=Kendall|first3=C. W.|last4=Emam|first4=A|last5=Jenkins|first5=D. J.}}
6. ^{{cite book|last=Kuksis|first=Arnis|title=Fat Digestion and Absorption|year=2000|publisher=The American Oil Chemists Society|isbn=978-1893997127|chapter-url=https://books.google.com/books?id=t5FNYzGEUDsC&pg=PA163|editor=Christophe, Armand B. |editor2=DeVriese, Stephanie|accessdate=December 21, 2012|page=163|chapter=Biochemistry of Glycerolipids and Formation of Chylomicrons}}
7. ^{{cite journal|pmc=4564526|year=2015|author1=Byrne|first1=C. S|title=The role of short chain fatty acids in appetite regulation and energy homeostasis|journal=International Journal of Obesity|volume=39|issue=9|pages=1331–1338|last2=Chambers|first2=E. S|last3=Morrison|first3=D. J|last4=Frost|first4=G|doi=10.1038/ijo.2015.84|pmid=25971927}}
8. ^{{Cite journal|last=Roy|first=Claude C.|last2=Kien|first2=C. Lawrence|last3=Bouthillier|first3=Lise|last4=Levy|first4=Emile|year=2006|title=Short-Chain Fatty Acids: Ready for Prime Time?|journal=Nutrition in Clinical Practice|volume=21|issue=4|pages=351–366|doi=10.1177/0115426506021004351|pmid=16870803|issn=0884-5336}}
9. ^{{cite journal | last=Rivière | first=Audrey | last2=Selak | first2=Marija | last3=Lantin | first3=David | last4=Leroy | first4=Frédéric | last5=De Vuyst | first5=Luc | title=Bifidobacteria and Butyrate-Producing Colon Bacteria: Importance and Strategies for Their Stimulation in the Human Gut | journal=Frontiers in Microbiology| volume=7 | pages=979 | date=28 June 2016 | issn=1664-302X | pmid=27446020 | pmc=4923077 | doi=10.3389/fmicb.2016.00979 }}

Further reading

  • [https://web.archive.org/web/20040302154550/http://www.danone-institute.be/communication/pdf/mono03/mono3-part4.pdf A review of the biological properties of SCFA from the Danone Institute] via archive.org
  • {{cite journal | vauthors = Besten GD, Bleeker A, Gerding A, van Eunen K, Havinga R, van Dijk TH, Oosterveer MH, Jonker JW, Groen AK, Reijngoud DJ, Bakker BM | title = Short-Chain Fatty Acids protect against High-Fat Diet-Induced Obesity via a PPARγ-dependent switch from lipogenesis to fat oxidation | journal = Diabetes | volume = 64| issue = 7| pages = 2398–408| year = 2015 | pmid = 25695945 | doi = 10.2337/db14-1213 | url = http://diabetes.diabetesjournals.org/cgi/pmidlookup?view=long&pmid=25695945 | accessdate = 2015-02-22}}
  • {{cite journal | vauthors = Canfora EE, Jocken JW, Blaak EE | title = Short-Chain Fatty Acids in control of body weight and insulin sensitivity | journal = Nature Reviews Endocrinology | volume = 11| issue = 10| pages = 577–91| year = 2015 | doi = 10.1038/nrendo.2015.128 | pmid = 26260141 }}
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