Short chain fatty acids

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Short chain fatty acids , and volatile fatty acids (engl. Short chain fatty acids , SCFA, synonym volatile fatty acids , VFA) are a subset of the fatty acids with two to six carbon atoms .

properties

Short-chain fatty acids are saturated and unbranched fatty acids (synonymous with alkyl monocarboxylates ) with a short chain length. A narrower alternative definition for short-chain fatty acids limits them to a maximum of four carbon atoms. Due to their low molecular weight , they are liquid and volatile at room temperature .

Short-chain fatty acids are formed in the intestine from indigestible carbohydrates ( fiber and digestive-resistant starch ) from the intestinal flora . In the epithelial cells of the intestine, they bind to the receptors FFAR2 and FFAR3 . Short-chain fatty acids are taken up by the transport proteins of the MCT family in almost all tissues , including the brain . They are involved in the regulation of appetite and in the energy metabolism . Short chain fatty acids are the preferred source of energy for cells in the rectum . Some short-chain fatty acids belong to the copulins . Various animal studies and a small number of human studies show that increased microbial production of short-chain fatty acids can be used in the prevention and treatment of metabolic diseases such as: B. Diabetes mellitus type 2 and obesity can help.

The analysis is mostly carried out using gas chromatography , high-performance liquid chromatography , nuclear magnetic resonance spectroscopy or capillary electrophoresis . Examples of short-chain fatty acids are acetic acid , propionic acid and butyric acid .

Examples

Fatty acid shorthand Surname Salt and ester names formula Molar mass
(g / mol) 		Structural formula
Common name Systematic name Common name Systematic name
C1: 0 (no SCFA) Formic acid Methanoic acid Formates Methanoates HCOOH 46.03
Formic acid skeleton
C2: 0 acetic acid Ethanoic acid Acetates Ethanoates CH 3 COOH 60.05
Acetic-acid-2D-skeletal.svg
C3: 0 Propionic acid Propanoic acid Propionate Propanoates CH 3 CH 2 COOH 74.08
Propionic acid chemical structure.svg
C4: 0 Butyric acid Butanoic acid Butyrate Butanoates CH 3 (CH 2 ) 2 COOH 88.11
Butyric acid acsv.svg
C4: 0 Isobutyric acid 2-methylpropanoic acid Isobutyrate 2-methylpropanoate (CH 3 ) 2 CHCOOH 88.11
Isoutyric-acid.svg
C5: 0 Valeric acid Pentanoic acid Valerates Pentanoates CH 3 (CH 2 ) 3 COOH 102.13
Valeric acid acsv.svg
C5: 0 Isovaleric acid 3-methylbutanoic acid Isovalate 3-methylbutanoate (CH 3 ) 2 CHCH 2 COOH 102.13
Isovaleric acid structure.png
C6: 0 Caproic acid Hexanoic acid Capronate Hexanoates CH 3 (CH 2 ) 4 COOH 116.16
Caproic acid skeleton

Individual evidence

  1. ^ A b c d John H. Cummings: Physiological and Clinical Aspects of Short-Chain Fatty Acids. Cambridge University Press, 2004, ISBN 978-0-521-61613-3 . S. XX.
  2. ^ Richard D. O'Brien: Fats and Oils. CRC Press, 2008, ISBN 978-1-420-06167-3 , p. 267.
  3. ↑ J. Tan, C. McKenzie, M. Potamitis, AN Thorburn, CR Mackay, L. Macia: The role of short-chain fatty acids in health and disease. In: Advances in immunology. Volume 121, 2014, pp. 91-119, doi : 10.1016 / B978-0-12-800100-4.00003-9 , PMID 24388214 .
  4. ↑ BT Layden, AR Angueira, M. Brodsky, V. Durai, WL Lowe: Short chain fatty acids and their receptors: new metabolic targets. In: Translational research: the journal of laboratory and clinical medicine. Volume 161, number 3, March 2013, pp. 131–140, doi : 10.1016 / j.trsl.2012.10.007 , PMID 23146568 .
  5. ↑ N. Vijay, ME Morris: Role of monocarboxylate transporters in drug delivery to the brain. In: Current pharmaceutical design. Volume 20, number 10, 2014, pp. 1487-1498, PMID 23789956 , PMC 4084603 (free full text).
  6. ↑ CS Byrne, ES Chambers, DJ Morrison, G. Frost: The role of short chain fatty acids in appetite regulation and energy homeostasis. In: International journal of obesity. Volume 39, number 9, September 2015, pp. 1331-1338, doi : 10.1038 / ijo.2015.84 , PMID 25971927 , PMC 4564526 (free full text).
  7. ↑ A. Andoh, T. Tsujikawa, Y. Fujiyama: Role of dietary fiber and short-chain fatty acids in the colon. In: Current pharmaceutical design. Volume 9, Number 4, 2003, pp. 347-358, PMID 12570825 .
  8. ↑ Emanuel E. Canfora, Ruth CR Meex, Koen Venema, Ellen E. Blaak: Gut microbial metabolites in obesity, NAFLD and T2DM . In: Nature Reviews Endocrinology . tape 15 , no. 5 , 2019, ISSN  1759-5029 , p. 261–273 , doi : 10.1038 / s41574-019-0156-z ( nature.com [accessed October 11, 2019]).
  9. ↑ M. Primec, D. Mičetić-Turk, T. Langerholc: Analysis of short-chain fatty acids in human feces: A scoping review. In: Analytical biochemistry. Volume 526, 06 2017, pp. 9-21, doi : 10.1016 / j.ab.2017.03.007 , PMID 28300535 .