Short-chain fatty acid

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Short-chain fatty acids (SCFAs), also referred to as volatile fatty acids (VFAs),[1] are fatty acids with an aliphatic tail of less than six carbon atoms.[2]

List of SCFAs[edit]

Lipid number Name Salt/Ester Name Formula Mass
(g/mol)
Diagram
Common Systematic Common Systematic Molecular Structural
Formic acid Methanoic acid Formate Methanoate CH2O2 HCOOH 46.03
Ameisensäure Skelett.svg
C2:0 Acetic acid Ethanoic acid Acetate Ethanoate C2H4O2 CH3COOH 60.05
Acetic-acid-2D-skeletal.svg
C3:0 Propionic acid Propanoic acid Propionate Propanoate C3H6O2 CH3CH2COOH 74.08
Propionic acid chemical structure.svg
C4:0 Butyric acid Butanoic acid Butyrate Butanoate C4H8O2 CH3(CH2)2COOH 88.11
Butyric acid acsv.svg
Isobutyric acid 2-Methylpropanoic acid Isobutyrate 2-Methylpropanoate C4H8O2 (CH3)2CHCOOH 88.11
Isoutyric-acid.svg
C5:0 Valeric acid Pentanoic acid Valerate Pentanoate C5H10O2 CH3(CH2)3COOH 102.13
Valeric acid acsv.svg
Isovaleric acid 3-Methylbutanoic acid Isovalerate 3-Methylbutanoate C5H10O2 (CH3)2CHCH2COOH 102.13
Isovaleric acid structure.png

Applications[edit]

Dietary relevance[edit]

Short-chain fatty acids are produced when dietary fiber is fermented in the colon.[3]

Short-chain fatty acids and medium-chain fatty acids are primarily absorbed through the portal vein during lipid digestion,[4] while long-chain fatty acids are packed into chylomicrons and enter lymphatic capillaries, and enter the blood first at the subclavian vein.

Medical relevance[edit]

The short-chain fatty acid butyrate is particularly important for colon health because it is the primary energy source for colonic cells and has anti-carcinogenic as well as anti-inflammatory properties[5] that are important for keeping colon cells healthy.[6][7] Butyrate inhibits the growth and proliferation of tumor cell lines in vitro, induces differentiation of tumor cells, producing a phenotype similar to that of the normal mature cell,[8] and induces apoptosis or programmed cell death of human colorectal cancer cells.[9][10] Butyrate inhibits angiogenesis by inactivating Sp1 transcription factor activity and downregulating VEGF gene expression.[11]

See also[edit]

References[edit]

  1. ^ "Role of Volatile Fatty Acids in Development of the Cecal Microflora in Broiler Chickens during Growth" at asm.org
  2. ^ Brody, Tom (1999). Nutritional Biochemistry (2nd ed.). Academic Press. p. 320. ISBN 0121348369. Retrieved December 21, 2012. 
  3. ^ Wong, Julia M.; de Souza, Russell; Kendall, Cyril W.; Emam, Azadeh; Jenkins, David J. (2006). "Colonic Health: Fermentation and Short Chain Fatty Acids". Journal of Clinical Gastroenterology 40 (3): 235–243. doi:10.1097/00004836-200603000-00015. PMID 16633129. 
  4. ^ Kuksis, Arnis (2000). "Biochemistry of Glycerolipids and Formation of Chylomicrons". In Christophe, Armand B.; DeVriese, Stephanie. Fat Digestion and Absorption. The American Oil Chemists Society. p. 163. ISBN 189399712X. Retrieved December 21, 2012. 
  5. ^ Greer JB, O'Keefe SJ (2011). "Microbial induction of immunity, inflammation, and cancer". Front Physiol 1: 168. doi:10.3389/fphys.2010.00168. PMC 3059938. PMID 21423403. 
  6. ^ Scheppach W (January 1994). "Effects of short chain fatty acids on gut morphology and function". Gut 35 (1 Suppl): S35–8. doi:10.1136/gut.35.1_Suppl.S35. PMC 1378144. PMID 8125387. 
  7. ^ Andoh A, Tsujikawa T, Fujiyama Y (2003). "Role of dietary fiber and short-chain fatty acids in the colon". Curr. Pharm. Des. 9 (4): 347–58. doi:10.2174/1381612033391973. PMID 12570825. 
  8. ^ Toscani A, Soprano DR, Soprano KJ (1988). "Molecular analysis of sodium butyrate-induced growth arrest". Oncogene Res. 3 (3): 223–38. PMID 3144695. 
  9. ^ Wong JM, de Souza R, Kendall CW, Emam A, Jenkins DJ (March 2006). "Colonic health: fermentation and short chain fatty acids". J. Clin. Gastroenterol. 40 (3): 235–43. doi:10.1097/00004836-200603000-00015. PMID 16633129. 
  10. ^ Scharlau D; Borowicki A; Habermann N et al. (2009). "Mechanisms of primary cancer prevention by butyrate and other products formed during gut flora-mediated fermentation of dietary fibre". Mutat. Res. 682 (1): 39–53. doi:10.1016/j.mrrev.2009.04.001. PMID 19383551. 
  11. ^ Prasanna Kumar S, Thippeswamy G, Sheela ML, Prabhakar BT, Salimath BP. Butyrate-induced phosphatase regulates VEGF and angiogenesis via Sp1. Arch Biochem Biophys. 2008 Oct 1;478(1):85-95.

Further reading[edit]