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] Free SCFAs can cross the blood-brain barrier via monocarboxylate transporters.[3][4]

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.[5]

Short-chain fatty acids 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.

Medical relevance[edit]

For more details on this topic, see Butyric acid § Research.

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[7] that are important for keeping colon cells healthy.[8][9] 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,[10] and induces apoptosis or programmed cell death of human colorectal cancer cells.[11][12] Butyrate inhibits angiogenesis by inactivating Sp1 transcription factor activity and downregulating VEGF gene expression.[13]

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. ^ Tsuji A (2005). "Small molecular drug transfer across the blood-brain barrier via carrier-mediated transport systems". NeuroRx 2 (1): 54–62. doi:10.1602/neurorx.2.1.54. PMC 539320. PMID 15717057. 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. ^ Vijay N, Morris ME (2014). "Role of monocarboxylate transporters in drug delivery to the brain". Curr. Pharm. Des. 20 (10): 1487–98. PMC 4084603. PMID 23789956. 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. ^ Wong, J. M.; De Souza, R; Kendall, C. W.; Emam, A; Jenkins, D. J. (2006). "Colonic health: Fermentation and short chain fatty acids". Journal of clinical gastroenterology 40 (3): 235–43. doi:10.1097/00004836-200603000-00015. PMID 16633129. 
  6. ^ 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. 
  7. ^ 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. 
  8. ^ 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. 
  9. ^ 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. 
  10. ^ Toscani A, Soprano DR, Soprano KJ (1988). "Molecular analysis of sodium butyrate-induced growth arrest". Oncogene Res. 3 (3): 223–38. PMID 3144695. 
  11. ^ 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. 
  12. ^ 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. 
  13. ^ Prasanna Kumar, S; Thippeswamy, G; Sheela, M. L.; Prabhakar, B. T.; Salimath, B. P. (2008). "Butyrate-induced phosphatase regulates VEGF and angiogenesis via Sp1". Archives of Biochemistry and Biophysics 478 (1): 85–95. doi:10.1016/j.abb.2008.07.004. PMID 18655767. 

Further reading[edit]