SFRBM Annual Meeting, Pre-meeting Workshop II Flavanols in Health and Disease
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1 FLAVILA Targeted delivery of dietary flavanols for optimal human cell function: Effects on cardiovascular health SFRBM Annual Meeting, Pre-meeting Workshop II Flavanols in Health and Disease Flavanols and Procyanidins: Absorption, Distribution, Metabolism, and Excretion Jeremy P E Spencer, University of Reading San Diego, 14 November 2012
2 !! Flavanols and procyanidins present in cocoa LU$$$$$ Epicatechin (DP1) Dimer B2 (DP2) $$ 400$ $$ DP1$ DP2$ H H H 200$ $$ DP3$ DP4$ DP5$ DP6$ DP7$ DP8$ DP9$ DP10$ Hammerstone et al., J. Agr. Food Chem., 47, FLAVILA session at the annual SFRBM meeting 14 November 2012
3 Are procyanidins absorbed and do they contribute to the pool of circulating flavanols in humans? FLAVILA session at the annual SFRBM meeting 14 November 2012
4 Procyanidins higher than DP2 are not absorbed following cocoa flavanol intake Flavanols and procyanidins ingested with each test drink (mg/kg BW) Flavanols(+(Procyanidins( ( DP(1210( DP22DP10( DP1( Flavanols((1(unit)( 2.10( 0.16( 1.8( ((((((4)4epicatechin( 1.80( 0.14( 1.8( ((((((+)4catechin( 0.28( 0.02( 0( There was no evidence for the absorption of procyanidins higher than DP 2 Procyanidins(( 9.91( 9.91( 0( (((((Dimers( 1.8( 1.8( 0( (((((Trimers( 1.6( 1.6( 0( (((((Tetramers(to(decamers( 6.5( 6.5( 0( "aviani et al. AJCN(2012) 95(4):851-8 FLAVILA session at the annual SFRBM meeting 14 November 2012
5 Procyanidin intake does not contribute to the pool of circulating flavanols in humans "aviani et al. AJCN(2012) 95(4):851-8 FLAVILA session at the annual SFRBM meeting 14 November 2012
6 Consumption of flavanol monomer (DP1) and procyanidins (DP 2-10) give rise to γ-valerolactone metabolites "aviani et al. AJCN(2012) 95(4):851-8 FLAVILA session at the annual SFRBM meeting 14 November 2012
7 What about the monomeric flavanols? FLAVILA session at the annual SFRBM meeting 14 November 2012
8 Chemical structure of flavanol stereoisomers ( )epicatechin, (+)epicatechin, ( )catechin, and (+)catechin H H (-)-Epicatechin (-)-Catechin H H (+)-Epicatechin (+)-Catechin FLAVILA session at the annual SFRBM meeting 14 November 2012
9 Plasma levels of flavanols after consumption of ( )epicatechin, (+)epicatechin, ( )catechin, or (+)catechin (1.5 mg/kg BW) Profile of flavanol metabolites in plasma 2 h post-consumption 800 ( )-epicatechin (+)-epicatechin ( )-catechin (+)-catechin Plasma flavanol metabolites 2 h post-consumption (nm) p<0.05 non-methylated metabolites 3'--methylated metabolites 4'--methylated metabolites ( )-epicatechin (+)-epicatechin ( )-catechin (+)-catechin n.d. n.d. "aviani et al. FRBM (2011) 50, FLAVILA session at the annual SFRBM meeting 14 November 2012
10 Standard food manufacture processes decrease flavanol contents Heat xidation ph Isomerisation (change in chemical structure) ( )$epicatechin- ( )$epicatechin- ( )$catechin- Based-on-these-findings,-we-created-technologies-that-preserve-the-flavanols-naturally-presentin-cocoa-during-food-manufacture,-making-flavanols-available-in-the-final-food-product.- FLAVILA session at the annual SFRBM meeting 14 November 2012
11 What are the major circulating flavanol metabolites in humans? FLAVILA session at the annual SFRBM meeting 14 November 2012
12 HPLC chromatogram trace of de novo synthesized (-)-epicatechin metabolites epicatechin 3'- sulphate 3'- - methyl epicatechin- 5- sulfate 3'- - methyl epicatechin- 7- sulfate epicatechin 3'- β- D - glucuronide E5G E7G
13 Circulating levels of (-)-epicatechin glucuronides following intake of the Flaviola test drink Level of ( )-epictechin glucuronides in plasma (nm) A ( )-epicatechin-3'-β-d-glucuronide 4'--methyl( )-epicatechin-7-β-d-glucuronide FLD intensity (LU) B A B C D Authentic standards Plasma 0 h Plasma 2 h F G Time after consumption (h) Elution time (min)! "aviani et al. FRBM (2012) 52(8): FLAVILA session at the annual SFRBM meeting 14 November 2012
14 Circulating levels of (-)-epicatechin sulfates following intake of the Flaviola test drink Level of individual ( )-epictechin sulfates in plasma (nm) A ( )-epicatechin-5-sulfate B I Authentic standards ( )-epicatechin-7-sulfate Plasma 0 h ( )-epicatechin-3'-sulfate Plasma 2 h 150 E H J Time after consumption (h) ECD intensity (na) ECD 550 mv ECD 550 mv ECD 225 mv Elution time (min) i ii iii iv! "aviani et al. FRBM (2012) 52(8): FLAVILA session at the annual SFRBM meeting 14 November 2012
15 (-)-epicatechin metabolism in humans H UGT ( )-epicatechin CMT + SULT H H SULT - C ( )-epicatechin-3 -β-dglucuronide ( )-epicatechin-3 - sulfate S - H - 3 S 3 --methyl( )-epicatechin- 5/7-sulfate CH 3 FLAVILA session at the annual SFRBM meeting 14 November 2012
16 Relative amounts of individual ( )-epicatechin metabolites in the circulation ( )-epicatechin-3 - β-d-glucuronide ( )-epicatechin- 3 -sulfate ( )-epicatechin- 5-sulfate "aviani et al. FRBM (2012) 52(8): ( )-epicatechin- 7-sulfate 4 --methyl( )- epicatechin-5/7-sulfates* 3 --methyl( )- epicatechin-5/7-sulfates* FLAVILA session at the annual SFRBM meeting 14 November 2012
17 Factors affecting flavanol absorption, distribution, metabolism and excretion FLAVILA session at the annual SFRBM meeting 14 November 2012
18 Intra-individual absorption and metabolism (n=9; 2 visits; 1 week washout) 2500 IntraAindividual,variability,(n=7) CV#%# C max %% T max %% AUC (0+6h)% Sum,of,flavanols,metabolites,,(,nM) CV 36% CV 19% CV 19% CV 22% CV 15% CV 21% CV 42% CV 49% E3'G% 30.1% 21.7% 26.0% E3'S% 25.3% 33.4% 32.8% 3ME5S% 18.9% 11.5% 24.4% 3ME7S% 25.7% 24.2% 32.0% Total% flavanols% 16.6# 13.9# 15.8# Time,after,flavanol,consumption,(h) According to FDA, drugs exhibi@ng intra- subject variability greater than 30% in AUC or Cmax are considered highly variable drugs FLAVILA session at the annual SFRBM meeting 14 November 2012
19 Inter-individual absorption and metabolism 2500 InterAindividual,variability,(n=20) CV#%# C max %% T max %% AUC (0+6h) % Sum,of,flavanols,metabolites,(nM) CV 49% CV 47% CV 42% CV 43% CV 44% CV 40% CV 50% CV 58% E3'G% 54.2% 23.7% 50.0% E3'S% 36.4% 34.4% 43.5% 3ME5S% 34.9% 46.2% 39.0% 3ME7S% 50.6% 38.2% 46.4% Total%flavanols% 38.6% 26.0% 38.1% Time,after,flavanol,consumption,(h) CV#%# C max %% T max %% %AUC (0+6h)% % Acetaminophen% glucuronide% Acetaminophen% sulfate% 48.8% 33.0% 55.4% 54.4% 34.4% 56.1% Acetaminophen% 27.1% 47.1% 25.2% Total% acetaminophen% 40.9% 41.4% 39.0% FLAVILA session at the annual SFRBM meeting 14 November 2012
20 Influence of age on the absorption and metabolism of flavanols CharacterisMcs Elderly (n=20) Young (n=20) Age (years) 70 ± 4 a 26 ± 6 b Weight (kg) 81 ± ± 9 BMI (kg/m 2 ) 27 ± 3 24 ± 2 GFR (ml/min/1.73m 2 ) 72 ± ± 22 Cholesterol (mm) 4.6 ± ± 1.2 Triglycerids (mm) 1.0 ± ± 0.4 Glucose (mm) 5.1 ± ± 0.4 CreaMnine (µm) 96.2 ± ± 14.4 Bilirubin (µm) 17.0 ± ± 5.5 Uric acid (µm) ± ± 74.1 ALT (U/L) 21.7 ± ± 6.3 GGT- L (U/L) 25.0 ± ± 8.0 ALP (U/L) 61.7 ± ± 15.4 n medicamon 7 - FLAVILA session at the annual SFRBM meeting 14 November 2012
21 Age does not influence total levels (AUC: 0-6h) of circulating flavanol metabolites Total Plasma AUC 5000 * * Young Elderly AUC 0-6h (nm*h) mg CF 800 mg CF FLAVILA session at the annual SFRBM meeting 14 November 2012
22 Plasma levels (AUC: 0-6h) of (-)-epicatechin metabolites in young and old AUC (-)-epicatechin-3'-glucuronide AUC 3'methyl-(-)-epicatechin-5-sulfate AUC 0-6h (nm*h) * * * Young Elderly AUC 0-6h (nm*h) * * * Young Elderly mg CF 800 mg CF mg CF 800 mg CF FLAVILA session at the annual SFRBM meeting 14 November 2012
23 Influence of age on (-)-epicatechin metabolism AUC%(036h)%in%Young%individuals% AUC(036h)%in%Elderly%individuals% EC% 1%% E3'G% 45%% E7S% 1%% E3'S% 20%% 3ME7S% 16%% E5S% 2%% 3ME5S% 15%% E3'G% 56%% E3'S% 18%% EC% 1%% 3ME5S% 11%% 3ME7S% 10%% E7S% 1%% E5S% 3%% FLAVILA session at the annual SFRBM meeting 14 November 2012
24 Urinary excretion of γ-valerolactones in young and old individuals Urinary -(3,4 dihydroxyphenyl)- gamma-valerolactone (µmol) * * * 400 mg CF 800 mg CF Young Elderly FLAVILA session at the annual SFRBM meeting 14 November 2012
25 Summary of the metabolism of flavanols following consumption H H Flavanol- and procyanidin- containing foods enter into the H H Chemical breakdown by gut microbiome [microbes in the gut] Diges@ve Tract [gut] ( )- epicatechin No absorpmon Flavanol oligomers (Procyanidins) 5- (3,4- dihydroxyphenyl) - γ- valerolactone Further reading: Saviani et al. FRBM (2012) Gastro- intesmnal barrier [gut cells] Systemic circulamon [blood] H H AbsorpMon and chemical modificamons - C S 3 - H ( )- epicatechin- 3ʹ - sulfate ( )- epicatechin- 3ʹ - β- D- glucuronide AbsorpMon and chemical modificamons S 3 - CH 3 3ʹ - - methyl( )- epicatechin- 5- sulfate S 3-5- (3,4- dihydroxyphenyl)- γ- valerolactone metabolites
26 Relevance for mechanistic assessment of flavanol function Flavanols in plants and foods Flavanols in humans H H H Flavanol oligomers (Procyanidins) H Flavanol ( )- epicatechin H H - C S 3 - H Flavanol metabolites S 3 - CH 3 - S 3 These findings are important, as they inform us about the chemical structure of the flavanols present in the human body, which enables research aimed at understanding the mechanisms by which flavanol- rich diets mediate cardiovascular health benefits.
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