Epicatechin
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-Epicatechin.svg)
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| (-) - Epicatechin (2 R , 3 R ) | ||||||||||||||||||||||
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| Surname | Epicatechin | |||||||||||||||||||||
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| Molecular formula | C 15 H 14 O 6 | |||||||||||||||||||||
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| Molar mass | 290.27 g mol −1 | |||||||||||||||||||||
| Physical state |
firmly |
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| Melting point |
240 ° C (decomposition) |
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| As far as possible and customary, SI units are used. Unless otherwise noted, the data given apply to standard conditions . | ||||||||||||||||||||||
Epicatechin is a polyphenol and catechin that was discovered in cocoa . Epicatechin refers to two diastereomers of catechin, the substituents of which are in the cis position. The more common epicatechin is (-) - epicatechin (2 R , 3 R ), the rarer epicatechin is (+) - epicatechin (2 S , 3 S ).
properties
-Epicatechin.svg)
Based on a comparison of the causes of death given in the death certificates between Guna Yala (an autonomous area on the east coast of Panama , formerly called San Blas ), and the adjacent mainland of Panama over four years (2000-2004) it was assumed that epicatechin from cocoa could have a positive effect on humans. The residents of Guna Yala have a very high consumption of cocoa. It was hypothesized that epicatechin could reduce the incidence of four of the five most common diseases in the western world ( stroke , heart attack , cancer and diabetes ) to less than ten percent. Although a statistical connection between illness or health and cocoa containing flavanol has to be established, the conclusion of a causal connection from this discovery must be viewed critically: other different life factors between the compared population groups and also between the quality of the statement of the cause of death in the death certificates were not examined. Corresponding negative controls have so far been missing . Epicatechin has a positive effect on long-term memory in snails. There is no statement about the transferability to humans, since a causal relationship has not been proven.
Metabolism in humans
In humans, epicatechin ingested through food is partially absorbed through the small intestine and still metabolized in the intestinal wall and later in the liver . The main metabolites that are formed are glucuronidated and sulfated derivatives of epicatechin. The portion of epicatechin that reaches the large intestine is broken down by the intestinal flora into γ- valerolactones and derivatives of hippuric acid , which can be absorbed in the human body and further metabolized there. If epicatechin is absorbed into the human body as a component of food, only metabolites of epicatechin are found in the blood and urine , but no free epicatechin. This must be taken into account when evaluating and interpreting scientific experiments which investigate epicatechin in cell cultures and isolated organs in vitro .
literature
- NK Hollenberg, ND Fisher, ML McCullough: Flavanols, the Kuna, cocoa consumption, and nitric oxide. In: Journal of the American Society of Hypertension: JASH. Volume 3, number 2, 2009 Mar-Apr, pp. 105-112, doi : 10.1016 / j.jash.2008.11.001 , PMID 20409950 , PMC 3835452 (free full text).
- DL Pucciarelli: Cocoa and heart health: a historical review of the science. In: Nutrients. Volume 5, number 10, September 2013, pp. 3854-3870, doi : 10.3390 / nu5103854 , PMID 24077240 , PMC 3820048 (free full text).
- CF Haskell-Ramsay, J. Schmitt, L. Actis-Goretta: The Impact of Epicatechin on Human Cognition: The Role of Cerebral Blood Flow. In: Nutrients. Volume 10, number 8, July 2018, p., Doi : 10.3390 / nu10080986 , PMID 30060538 , PMC 6115745 (free full text).
Individual evidence
- ↑ a b c d data sheet (-) - Epicatechin, ≥90% (HPLC) from Sigma-Aldrich , accessed on October 15, 2018 ( PDF ).
- ↑ a b c V. Bayard, F. Chamorro, J. Motta, NK Hollenberg: Does flavanol intake influence mortality from nitric oxide-dependent processes? Ischemic heart disease, stroke, diabetes mellitus, and cancer in Panama. In: International journal of medical sciences. Volume 4, Number 1, January 2007, pp. 53-58, PMID 17299579 , PMC 1796954 (free full text).
- ↑ dradio - Research News - News - Neuroscience: Learning is easier with chocolate from September 27, 2012 .
- ↑ a b c d Javier I. Ottaviani, Gina Borges, Tony Y. Momma, Jeremy PE Spencer, Carl L. Keen: The metabolome of [2-14C] ( -) - epicatechin in humans: implications for the assessment of efficacy, safety, and mechanisms of action of polyphenolic bioactives . In: Scientific Reports . tape 6 , July 1, 2016, ISSN 2045-2322 , doi : 10.1038 / srep29034 , PMID 27363516 , PMC 4929566 (free full text).
- ^ Alan Crozier: Absorption, metabolism, and excretion of ( -) - epicatechin in humans: an evaluation of recent findings . In: The American Journal of Clinical Nutrition . tape 98 , no. 4 , October 1, 2013, ISSN 0002-9165 , p. 861-862 , doi : 10.3945 / ajcn.113.072009 , PMID 23985809 .
- ↑ Javier I. Ottaviani, Tony Y. Momma, Gunter K. Kuhnle, Carl L. Keen, Hagen Schroeter: Structurally related ( -) - epicatechin metabolites in humans: Assessment using de novo chemically synthesized authentic standards . In: Free Radical Biology and Medicine . tape 52 , no. 8 , April 15, 2012, p. 1403-1412 , doi : 10.1016 / j.freeradbiomed.2011.12.010 .
- ↑ Lucas Actis-Goretta, Antoine Lévèques, Maarit Rein, Alexander Teml, Christian Schäfer: Intestinal absorption, metabolism, and excretion of (-) - epicatechin in healthy humans assessed by using an intestinal perfusion technique . In: The American Journal of Clinical Nutrition . tape 98 , no. 4 , October 1, 2013, ISSN 0002-9165 , p. 924-933 , doi : 10.3945 / ajcn.113.065789 , PMID 23864538 .