Abstract
Extensive epidemiological and clinical evidence associates diets high in flavanol-containing foods with cardiovascular health benefits in humans. Catechin and epicatechin, the most common flavanols in foods, are present in the diet in different enantiomeric forms. This study investigated the influence of the stereochemical configuration of flavanols on their absorption, metabolism, and biological activity. Healthy adult males were asked to consume equal amounts of the stereochemically pure flavanols (-)-epicatechin, (-)-catechin, (+)-catechin, and (+)-epicatechin (1.5 mg/kg bw) in a well-defined cocoa-based, dairy-containing drink matrix, and flavanol levels were subsequently determined in plasma and 24-h urine. The results obtained show that the stereochemical configuration of flavanols has a profound influence on their uptake and metabolism in humans. In addition, we assessed the vasodilatory activity of each flavanol stereoisomer in vivo and found (-)-epicatechin to be the single stereoisomer capable of mediating a significant arterial dilation response. Importantly, this effect was independent of the classic antioxidant properties of flavanols. Overall, these results indicate that the proposed beneficial health effects associated with the consumption of flavanol-containing foods will significantly depend on the stereochemical configuration of the flavanols ingested.
| Original language | English (US) |
|---|---|
| Pages (from-to) | 237-244 |
| Number of pages | 8 |
| Journal | Free Radical Biology and Medicine |
| Volume | 50 |
| Issue number | 2 |
| DOIs | |
| State | Published - Jan 15 2011 |
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Keywords
- Antioxidant
- Epicatechin
- Flavanols
- Free radicals
- Polyphenols
ASJC Scopus subject areas
- Biochemistry
- Physiology (medical)
Cite this
The stereochemical configuration of flavanols influences the level and metabolism of flavanols in humans and their biological activity in vivo. / Ottaviani, Javier I.; Momma, Tony Y.; Heiss, Christian; Kwik-Uribe, Catherine; Schroeter, Hagen; Keen, Carl L.
In: Free Radical Biology and Medicine, Vol. 50, No. 2, 15.01.2011, p. 237-244.Research output: Contribution to journal › Article
}
TY - JOUR
T1 - The stereochemical configuration of flavanols influences the level and metabolism of flavanols in humans and their biological activity in vivo
AU - Ottaviani, Javier I.
AU - Momma, Tony Y.
AU - Heiss, Christian
AU - Kwik-Uribe, Catherine
AU - Schroeter, Hagen
AU - Keen, Carl L
PY - 2011/1/15
Y1 - 2011/1/15
N2 - Extensive epidemiological and clinical evidence associates diets high in flavanol-containing foods with cardiovascular health benefits in humans. Catechin and epicatechin, the most common flavanols in foods, are present in the diet in different enantiomeric forms. This study investigated the influence of the stereochemical configuration of flavanols on their absorption, metabolism, and biological activity. Healthy adult males were asked to consume equal amounts of the stereochemically pure flavanols (-)-epicatechin, (-)-catechin, (+)-catechin, and (+)-epicatechin (1.5 mg/kg bw) in a well-defined cocoa-based, dairy-containing drink matrix, and flavanol levels were subsequently determined in plasma and 24-h urine. The results obtained show that the stereochemical configuration of flavanols has a profound influence on their uptake and metabolism in humans. In addition, we assessed the vasodilatory activity of each flavanol stereoisomer in vivo and found (-)-epicatechin to be the single stereoisomer capable of mediating a significant arterial dilation response. Importantly, this effect was independent of the classic antioxidant properties of flavanols. Overall, these results indicate that the proposed beneficial health effects associated with the consumption of flavanol-containing foods will significantly depend on the stereochemical configuration of the flavanols ingested.
AB - Extensive epidemiological and clinical evidence associates diets high in flavanol-containing foods with cardiovascular health benefits in humans. Catechin and epicatechin, the most common flavanols in foods, are present in the diet in different enantiomeric forms. This study investigated the influence of the stereochemical configuration of flavanols on their absorption, metabolism, and biological activity. Healthy adult males were asked to consume equal amounts of the stereochemically pure flavanols (-)-epicatechin, (-)-catechin, (+)-catechin, and (+)-epicatechin (1.5 mg/kg bw) in a well-defined cocoa-based, dairy-containing drink matrix, and flavanol levels were subsequently determined in plasma and 24-h urine. The results obtained show that the stereochemical configuration of flavanols has a profound influence on their uptake and metabolism in humans. In addition, we assessed the vasodilatory activity of each flavanol stereoisomer in vivo and found (-)-epicatechin to be the single stereoisomer capable of mediating a significant arterial dilation response. Importantly, this effect was independent of the classic antioxidant properties of flavanols. Overall, these results indicate that the proposed beneficial health effects associated with the consumption of flavanol-containing foods will significantly depend on the stereochemical configuration of the flavanols ingested.
KW - Antioxidant
KW - Epicatechin
KW - Flavanols
KW - Free radicals
KW - Polyphenols
UR - http://www.scopus.com/inward/record.url?scp=78651249150&partnerID=8YFLogxK
UR - http://www.scopus.com/inward/citedby.url?scp=78651249150&partnerID=8YFLogxK
U2 - 10.1016/j.freeradbiomed.2010.11.005
DO - 10.1016/j.freeradbiomed.2010.11.005
M3 - Article
C2 - 21074608
AN - SCOPUS:78651249150
VL - 50
SP - 237
EP - 244
JO - Free Radical Biology and Medicine
JF - Free Radical Biology and Medicine
SN - 0891-5849
IS - 2
ER -