Page last updated: 2024-11-10

flavan-3-ol

Description Research Excerpts Clinical Trials Roles Classes Pathways Study Profile Bioassays Related Drugs Related Conditions Protein Interactions Research Growth Market Indicators

Description

flavan-3-ol: structure in first source [Medical Subject Headings (MeSH), National Library of Medicine, extracted Dec-2023]

Cross-References

ID SourceID
PubMed CID3707243
CHEBI ID79987
SCHEMBL ID20116
MeSH IDM0358576

Synonyms (13)

Synonym
flavan-3-ol
2-phenyl-3,4-dihydro-2h-chromen-3-ol
2h-1-benzopyran-3-ol, 3,4-dihydro-2-phenyl-
1481-83-0
SCHEMBL20116
CHEBI:79987
3-flavanol
OEIJRRGCTVHYTH-UHFFFAOYSA-N
3,4-dihydro-2-phenyl-2h-1-benzopyran-3-ol
35HDD3NRIE ,
favan-3-ol
Q27149144
unii-35hdd3nrie

Research Excerpts

Toxicity

ExcerptReferenceRelevance
" Diffuse acinar cell hypertrophy, observed in the parotid salivary glands in all treatment groups, was not considered as adverse and presumably reflected a local, reversible and adaptive response to direct contact with EvesseEPC."( Safety evaluation of Evesse EPC, an apple polyphenol extract rich in flavan-3-ols.
Bui, Q; Hasselwander, O; Lina, BA; Reus, AA; Tenning, PP, 2012
)
0.61

Pharmacokinetics

ExcerptReferenceRelevance
" An 8-h pharmacokinetic study was performed."( Influence of diabetes on plasma pharmacokinetics and brain bioavailability of grape polyphenols and their phase II metabolites in the Zucker diabetic fatty rat.
Chen, TY; Cooper, B; Ferruzzi, MG; Ho, L; Janle, EM; Pasinetti, GM; Simon, JE; Talcott, ST; Todd, G; Wang, J; Wu, QL, 2017
)
0.46

Compound-Compound Interactions

ExcerptReferenceRelevance
" In this work, a new electrochemical approach based on molecularly imprinted polymer extraction and preconcentration, combined with a disposable carbon screen-printed sensor and adsorptive transfer differential pulse voltammetry detection has been proposed for quantifying of 4-hydroxyphenylacetic acid (4-HPA), which is a biomarker of flavan-3-ols intake, and other phenolic acids."( Disposable electrochemical sensor combined with molecularly imprinted solid-phase extraction for catabolites detection of flavan-3-ol in urine samples.
Crevillen, AG; Gallego-Picó, A; González-Gómez, D; Mora-Granados, M, 2021
)
1

Bioavailability

The objective was to determine the effect of milk on the bioavailability of cocoa flavan-3-ol metabolites. The results establish the value of the UHPLC-HRMS protocol in obtaining a detailed picture of proanthocyanidin metabolites and microbial-derived catabolites.

ExcerptReferenceRelevance
"There is considerable interest in the bioavailability of flavan-3-ols such as tea catechins and cocoa-derived procyanidin components of the diet and their bioactivity in vivo."( Bioavailability of flavan-3-ols and procyanidins: gastrointestinal tract influences and their relevance to bioactive forms in vivo.
Rechner, AR; Rice-Evans, C; Schroeter, H; Spencer, JP, 2001
)
0.88
" This article gives an overview of the role of chemical characteristics and endogenous metabolism of tea PP and their bioavailability in humans and describes attempts to increase their bioavailability."( Nongallated compared with gallated flavan-3-ols in green and black tea are more bioavailable.
Choo, JJ; Heber, D; Henning, SM, 2008
)
0.62
" However, the importance of these health beneficial effects of these botanicals remains elusive due to incomplete understanding of uptake, metabolism and bioavailability of proanthocyanidins in vivo."( Liquid chromatography tandem mass spectrometry identification of proanthocyanidins in rat plasma after oral administration of grape seed extract.
Arabshahi, A; Barnes, S; Dai, Y; Kim, H; Michael Wyss, J; Moore, R; Peng, N; Prasain, JK; Watts, RL; Wilson, L, 2009
)
0.35
"Cocoa drinks containing flavan-3-ols are associated with many health benefits, and conflicting evidence exists as to whether milk adversely affects the bioavailability of flavan-3-ols."( Milk decreases urinary excretion but not plasma pharmacokinetics of cocoa flavan-3-ol metabolites in humans.
Borges, G; Crozier, A; Donovan, JL; Edwards, CA; Lean, ME; Mullen, W; Serafini, M, 2009
)
0.89
"The objective was to determine the effect of milk on the bioavailability of cocoa flavan-3-ol metabolites."( Milk decreases urinary excretion but not plasma pharmacokinetics of cocoa flavan-3-ol metabolites in humans.
Borges, G; Crozier, A; Donovan, JL; Edwards, CA; Lean, ME; Mullen, W; Serafini, M, 2009
)
0.81
" Studies that showed protective effects of cocoa and those that showed no effect of milk on bioavailability used products that have a much higher flavan-3-ol content than does the commercial cocoa used in the present study."( Milk decreases urinary excretion but not plasma pharmacokinetics of cocoa flavan-3-ol metabolites in humans.
Borges, G; Crozier, A; Donovan, JL; Edwards, CA; Lean, ME; Mullen, W; Serafini, M, 2009
)
0.78
"The bioavailability values observed are in agreement with previous reports, although the dosage of polyphenols ingested in this study is remarkably lower."( Bioavailability of catechins from ready-to-drink tea.
Brighenti, F; Calani, L; Cordero, C; Del Rio, D; Jechiu, L; Scazzina, F, 2010
)
0.36
"Conflicting data exist regarding the influence of chocolate matrices on the bioavailability of epicatechin (EC) from cocoa."( Influence of chocolate matrix composition on cocoa flavan-3-ol bioaccessibility in vitro and bioavailability in humans.
Ferruzzi, MG; George, JC; Janle, EM; Mattes, RD; Matusheski, NV; Neilson, AP; Rudolph, R, 2009
)
0.6
" The data obtained point to the importance of the colonic microflora in the overall bioavailability and potential bioactivity of dietary flavonoids."( Green tea flavan-3-ols: colonic degradation and urinary excretion of catabolites by humans.
Crozier, A; Edwards, CA; Lean, ME; Mullen, W; Roowi, S; Stalmach, A, 2010
)
0.76
"The impact of carbohydrates and milk on the bioavailability of catechin (C) and epicatechin (EC) from chocolate has been previously studied."( Chocolate matrix factors modulate the pharmacokinetic behavior of cocoa flavan-3-ol phase II metabolites following oral consumption by Sprague-Dawley rats.
Ferruzzi, MG; Janle, EM; Matusheski, NV; Neilson, AP; Rudolph, R; Sapper, TN, 2010
)
0.59
" The findings presented in this work provide evidence concerning the bioavailability of almond skin polyphenols considering the effects of both phase II and microbial metabolism."( Targeted analysis of conjugated and microbial-derived phenolic metabolites in human urine after consumption of an almond skin phenolic extract.
Andrés-Lacueva, C; Bartolomé, B; Garrido, I; Gómez-Cordovés, C; Llorach, R; Martín-Alvarez, PJ; Monagas, M; Urpi-Sarda, M, 2010
)
0.36
" Bioavailability of flavan-3-ols is largely influenced by their degree of polymerization; while monomers are readily absorbed in the small intestine, oligomers and polymers need to be biotransformed by the colonic microbiota before absorption."( Insights into the metabolism and microbial biotransformation of dietary flavan-3-ols and the bioactivity of their metabolites.
Andres-Lacueva, C; Bartolomé, B; Garrido, I; Gómez-Cordovés, C; Llorach, R; Monagas, M; Sánchez-Patán, F; Urpi-Sarda, M, 2010
)
0.92
" Both epidemiological and biological evidence suggests a health-protective role for dietary flavan-3-ols, leading to increased interest in the bioavailability of these compounds from foods."( Influence of formulation and processing on absorption and metabolism of flavan-3-ols from tea and cocoa.
Ferruzzi, MG; Neilson, AP, 2011
)
0.82
" The average 48 h bioavailability was close to 62%, major contributors being microbial metabolites."( Updated bioavailability and 48 h excretion profile of flavan-3-ols from green tea in humans.
Brighenti, F; Calani, L; Del Rio, D; Luisa Callegari, M; Morelli, L, 2012
)
0.63
"This paper reviews recent human studies on the bioavailability of chlorogenic acids in coffee and green tea flavan-3-ols in which the identification of metabolites, catabolites and parent compounds in plasma, urine and ileal fluid was based on mass spectrometric methodology."( Bioavailability of coffee chlorogenic acids and green tea flavan-3-ols.
Calani, L; Crozier, A; Del Rio, D; Stalmach, A, 2010
)
0.82
" Together, these data suggest that the flavan-3-ol profile of a particular food source could affect the microbiota composition and its catabolic activity, inducing changes that could in turn affect the bioavailability and potential bioactivity of these compounds."( In vitro fermentation of grape seed flavan-3-ol fractions by human faecal microbiota: changes in microbial groups and phenolic metabolites.
Bartolomé, B; Cueva, C; Gibson, GR; Martín-Álvarez, PJ; Monagas, M; Moreno-Arribas, MV; Sánchez-Patán, F; Walton, GE, 2013
)
0.93
" Blood and urine samples were obtained just before and 2 and 6 h after consumption for measurements of platelet function, and bioavailability and excretion of flavan-3-ols."( Flavan-3-ol-enriched dark chocolate and white chocolate improve acute measures of platelet function in a gender-specific way--a randomized-controlled human intervention trial.
Cienfuegos-Jovellanos, E; de Roos, B; Duthie, GG; Horgan, GW; Kroon, PA; Ostertag, LM; Saha, S; Wood, S, 2013
)
2.03
"Recent research on the bioavailability of flavan-3-ols after ingestion of green tea by humans is reviewed."( Human studies on the absorption, distribution, metabolism, and excretion of tea polyphenols.
Clifford, MN; Crozier, A; van der Hooft, JJ, 2013
)
0.65
" Even within the same subclass, flavonoids may differ considerably in bioavailability and bioactivity."( Dietary intakes of individual flavanols and flavonols are inversely associated with incident type 2 diabetes in European populations.
Amiano, P; Boeing, H; Bredsdorff, L; Buijsse, B; Fagherazzi, G; Feskens, EJ; Forouhi, NG; Franks, PW; González, CA; Grioni, S; Guevara, M; Katzke, V; Key, TJ; Khaw, KT; Kühn, T; Langenberg, C; Masala, G; Mattiello, A; Molina-Montes, E; Nilsson, PM; Overvad, K; Perquier, F; Redondo, ML; Riboli, E; Ricceri, F; Rolandsson, O; Romieu, I; Roswall, N; Scalbert, A; Schulze, M; Sharp, SJ; Slimani, N; Spijkerman, AM; Tjonneland, A; Tormo, MJ; Touillaud, M; Tumino, R; van der A, DL; van der Schouw, YT; van Woudenbergh, GJ; Wareham, NJ; Zamora-Ros, R, 2014
)
0.4
"Interactions between polyphenols and macromolecules may impact polyphenol stability and bioavailability from foods."( Thermal degradation of green tea flavan-3-ols and formation of hetero- and homocatechin dimers in model dairy beverages.
Ferruzzi, MG; Manganais, C; Song, BJ, 2015
)
0.7
" The effects depend on their concentrations in target tissues and hence the bioavailability pathways followed by each particular compound."( Flavan-3-ols, anthocyanins, and inflammation.
Baenas, N; Domínguez-Perles, R; García-Viguera, C; Gironés-Vilaplana, A; Mena, P; Villaño, D, 2014
)
1.85
"Despite differences in epicatechin dose, improvements in vascular function after pure epicatechin and chocolate were similar and the bioavailability did not differ, suggesting a role for epicatechin."( Does epicatechin contribute to the acute vascular function effects of dark chocolate? A randomized, crossover study.
Dower, JI; Geleijnse, JM; Hollman, PC; Kromhout, D; Kroon, PA; Mensink, M; Philo, M, 2016
)
0.43
"The relatively low oral bioavailability of flavan-3-ols from acute doses is commonly highlighted as a limitation when considering the biological significance of these compounds."( Differentiated Caco-2 cell monolayers exhibit adaptation in the transport and metabolism of flavan-3-ols with chronic exposure to both isolated flavan-3-ols and enriched extracts.
Chegeni, M; Ferruzzi, MG; Redan, BW, 2017
)
0.94
"This work opens the door to better studying the bioavailability of flavan-3-ols and the real exposition to flavan-3-ol sources, as well as to define the bioactivity of these colonic metabolites in cell assays."( Synthetic and analytical strategies for the quantification of phenyl-γ-valerolactone conjugated metabolites in human urine.
Benzie, I; Brighenti, F; Brindani, N; Calani, L; Choi, SW; Curti, C; Del Rio, D; Mena, P; Zanardi, F, 2017
)
0.69
"The effect of diabetes on the pharmacokinetics, bioavailability and brain distribution of grape polyphenols and select metabolites was studied in the Zucker diabetic fatty (ZDF) rat model."( Influence of diabetes on plasma pharmacokinetics and brain bioavailability of grape polyphenols and their phase II metabolites in the Zucker diabetic fatty rat.
Chen, TY; Cooper, B; Ferruzzi, MG; Ho, L; Janle, EM; Pasinetti, GM; Simon, JE; Talcott, ST; Todd, G; Wang, J; Wu, QL, 2017
)
0.46
"Diabetes may alter the overall bioavailability of some polyphenols in plasma and brain in part due to higher urinary clearance."( Influence of diabetes on plasma pharmacokinetics and brain bioavailability of grape polyphenols and their phase II metabolites in the Zucker diabetic fatty rat.
Chen, TY; Cooper, B; Ferruzzi, MG; Ho, L; Janle, EM; Pasinetti, GM; Simon, JE; Talcott, ST; Todd, G; Wang, J; Wu, QL, 2017
)
0.46
" However, the mechanisms involved in this reduction are unclear, particularly because of the poor bioavailability of flavan 3-ols."( Possible mechanisms of postprandial physiological alterations following flavan 3-ol ingestion.
Osakabe, N; Terao, J, 2018
)
0.48
" These results establish the value of the UHPLC-HRMS protocol in obtaining a detailed picture of proanthocyanidin metabolites and their microbial-derived catabolites, along with their phase II metabolites, in biological fluids of rat, and potentially in human clinical studies designed to evaluate the bioavailability of dietary flavan-3-ols."( Development and validation of an UHPLC-HRMS protocol for the analysis of flavan-3-ol metabolites and catabolites in urine, plasma and feces of rats fed a red wine proanthocyanidin extract.
Bindon, KA; Crozier, A; Del Rio, D; Gaillet, S; Ludwig, I; Mena, P; Moreno-Rojas, JM; Ordóñez, JL; Pereira-Caro, G; Rouanet, JM, 2018
)
0.88
"There is much information on the bioavailability of (poly)phenolic compounds following acute intake of various foods."( Inter-individual variability in the production of flavan-3-ol colonic metabolites: preliminary elucidation of urinary metabotypes.
Acharjee, A; Bluck, LJ; Brighenti, F; Calani, L; Del Rio, D; Griffin, JL; Ludwig, IA; Mena, P; Ray, S; Rosi, A; Tomatis, VB, 2019
)
0.77
"The selective production of microbiota-derived metabolites from flavan-3-ols and the putative existence of characteristic metabotypes in their production represent an important development in the study of the bioavailability of plant bioactives."( Inter-individual variability in the production of flavan-3-ol colonic metabolites: preliminary elucidation of urinary metabotypes.
Acharjee, A; Bluck, LJ; Brighenti, F; Calani, L; Del Rio, D; Griffin, JL; Ludwig, IA; Mena, P; Ray, S; Rosi, A; Tomatis, VB, 2019
)
1.01
" The formation, bioavailability and pharmacokinetics of PVLs and PVAs from different types of flavan-3-ols are discussed, taking into account in vitro and animal studies, as well as inter-individual differences and the existence of putative flavan-3-ol metabotypes."( Phenyl-γ-valerolactones and phenylvaleric acids, the main colonic metabolites of flavan-3-ols: synthesis, analysis, bioavailability, and bioactivity.
Angelino, D; Bresciani, L; Brighenti, F; Brindani, N; Calani, L; Clifford, MN; Crozier, A; Curti, C; Del Rio, D; Gill, CIR; Llorach, R; Ludwig, IA; Mena, P; Pereira-Caro, G, 2019
)
0.96
" However, these phenolic compounds have a very low bioavailability and extensively undergo phase I and II metabolism, with the appearing into the bloodstream of (epi)catechin conjugates and phenyl-γ-valerolactones and their conjugates, at different times."( Dark chocolate modulates platelet function with a mechanism mediated by flavan-3-ol metabolites.
Angelino, D; Benati, M; Danese, E; Del Rio, D; Favaloro, EJ; Gelati, M; Lippi, G; Mena, P; Montagnana, M; Rosi, A; Salvagno, GL, 2018
)
0.71
" However, differences in (poly)phenol profiles and bioavailability likely exist between whole fruit and 100% fruit juice due to processing and the presence/absence of fiber."( Potential health benefits of (poly)phenols derived from fruit and 100% fruit juice.
Ferruzzi, MG; Ho, KKHY; Wightman, JD, 2020
)
0.56
" This review is focused on the bioavailability of polyphenols and the use of polyphenols for the prevention of prostate diseases."( The Polyphenols as Potential Agents in Prevention and Therapy of Prostate Diseases.
Dolićanin, Z; Džamić, Z; Gašić, U; Pejčić, T; Tešić, Ž; Tosti, T; Vuksanović, A, 2019
)
0.51
" However, phenolics like flavan-3-ols (F3O) are poorly absorbed along the gastrointestinal tract and structurally rearranged by gut microbiota, yielding smaller and more polar metabolites like phenyl-γ-valerolactones, phenylvaleric acids and their conjugates."( 5-(Hydroxyphenyl)-γ-Valerolactone-Sulfate, a Key Microbial Metabolite of Flavan-3-ols, Is Able to Reach the Brain: Evidence from Different in
Angelino, D; Bladé, C; Brighenti, F; Brindani, N; Brito, MA; Carregosa, D; Curti, C; Davis, CD; Del Bas, JM; Del Rio, D; Domenech-Coca, C; Figueira, I; Jang, S; Kim, KS; Lakshman, S; Mena, P; Molokin, A; Santos, CND; Savi, M; Solano-Aguilar, GI; Stilli, D; Urban, JF, 2019
)
1.05
"Food matrix interactions with polyphenols can affect their bioavailability and as a consequence may modulate their biological effects."( Effects of the apple matrix on the postprandial bioavailability of flavan-3-ols and nutrigenomic response of apple polyphenols in minipigs challenged with a high fat meal.
Bayle, D; Boby, C; Borel, P; Buffière, C; Dufour, C; Istas, G; Le Bourvellec, C; Mercier, S; Milenkovic, D; Monfoulet, LE; Morand, C; Remond, D; Rodriguez-Mateos, A, 2020
)
0.79
" Recent studies showed that flavan-3-ols could interact with methylxanthines, evidenced by an increase in flavan-3-ol bioavailability with a concomitant increase in flavan-3-ol intake-mediated vascular effects."( Flavan-3-ol-methylxanthine interactions: Modulation of flavan-3-ol bioavailability in volunteers with a functional colon and an ileostomy.
Borges, G; Crozier, A; Dobani, S; Durkan, R; Ensunsa, JL; Fong, RY; Gill, CIR; Kane, E; Kimball, J; Lawther, R; Medici, V; O'Connor, G; Ottaviani, JI; Pourshahidi, LK; Schroeter, H; Ward, K, 2023
)
2.65

Dosage Studied

ExcerptRelevanceReference
"The bioavailability values observed are in agreement with previous reports, although the dosage of polyphenols ingested in this study is remarkably lower."( Bioavailability of catechins from ready-to-drink tea.
Brighenti, F; Calani, L; Cordero, C; Del Rio, D; Jechiu, L; Scazzina, F, 2010
)
0.36
"The present analysis suggests that flavonoid bioactivity does not follow a classical linear dose-response association and this may have important biological implications."( Relative impact of flavonoid composition, dose and structure on vascular function: a systematic review of randomised controlled trials of flavonoid-rich food products.
Cassidy, A; Hooper, L; Kay, CD; Kroon, PA; Rimm, EB, 2012
)
0.38
" Longer term dose-response randomized controlled trials are required to determine the sustainability of the short-term effects and the optimal dose."( Flavan-3-ols, theobromine, and the effects of cocoa and chocolate on cardiometabolic risk factors.
Berends, LM; Cassidy, A; van der Velpen, V, 2015
)
1.86
"(ZDF) rats and their lean controls (LN) were dosed with a Standardized Grape Polyphenol (SGP) Mixture consisting of grape seed extract, Concord grape juice and resveratrol (RES) by oral gavage for 10 days."( Influence of diabetes on plasma pharmacokinetics and brain bioavailability of grape polyphenols and their phase II metabolites in the Zucker diabetic fatty rat.
Chen, TY; Cooper, B; Ferruzzi, MG; Ho, L; Janle, EM; Pasinetti, GM; Simon, JE; Talcott, ST; Todd, G; Wang, J; Wu, QL, 2017
)
0.46
" Mice in the vehicle treatment groups were administered distilled water and those in the FL treatment groups were dosed with FL (50mg/kg/day) for 2weeks."( Flavan 3-ol delays the progression of disuse atrophy induced by hindlimb suspension in mice.
Ashida, H; Hirota, Y; Imai, T; Ito, M; Kudo, N; Miyake, Y; Osakabe, N; Unno, T; Yamashita, Y, 2017
)
0.46
" Future research should focus on an integrated intake/biomarker approach in cohorts and high-quality dose-response RCTs."( Dietary intakes of flavan-3-ols and cardiometabolic health: systematic review and meta-analysis of randomized trials and prospective cohort studies.
Avendano, EE; Cassidy, A; Chen, S; Gayer, B; Matson, J; Novotny, JA; Raman, G; Wang, J, 2019
)
0.84
[information is derived through text-mining from research data collected from National Library of Medicine (NLM), extracted Dec-2023]

Drug Classes (1)

ClassDescription
hydroxyflavonoidAny flavonoid in which one or more ring hydrogens are replaced by hydroxy groups.
[compound class information is derived from Chemical Entities of Biological Interest (ChEBI), Hastings J, Owen G, Dekker A, Ennis M, Kale N, Muthukrishnan V, Turner S, Swainston N, Mendes P, Steinbeck C. (2016). ChEBI in 2016: Improved services and an expanding collection of metabolites. Nucleic Acids Res]

Research

Studies (404)

TimeframeStudies, This Drug (%)All Drugs %
pre-19900 (0.00)18.7374
1990's0 (0.00)18.2507
2000's101 (25.00)29.6817
2010's248 (61.39)24.3611
2020's55 (13.61)2.80
[information is prepared from research data collected from National Library of Medicine (NLM), extracted Dec-2023]

Market Indicators

Research Demand Index: 38.47

According to the monthly volume, diversity, and competition of internet searches for this compound, as well the volume and growth of publications, there is estimated to be strong demand-to-supply ratio for research on this compound.

MetricThis Compound (vs All)
Research Demand Index38.47 (24.57)
Research Supply Index6.06 (2.92)
Research Growth Index6.30 (4.65)
Search Engine Demand Index56.46 (26.88)
Search Engine Supply Index2.00 (0.95)

This Compound (38.47)

All Compounds (24.57)

Study Types

Publication TypeThis drug (%)All Drugs (%)
Trials17 (4.15%)5.53%
Reviews45 (10.98%)6.00%
Case Studies0 (0.00%)4.05%
Observational1 (0.24%)0.25%
Other347 (84.63%)84.16%
[information is prepared from research data collected from National Library of Medicine (NLM), extracted Dec-2023]