455:). It is a testing method that measures the change in color when the product is mixed with certain chemicals. The greater the color changes, the higher the PCOs content is. However, the Procyanidolic Index is a relative value that can measure well over 100. Unfortunately, a Procyanidolic Index of 95 was erroneously taken to mean 95% PCO by some and began appearing on the labels of finished products. All current methods of analysis suggest that the actual PCO content of these products is much lower than 95%.
911:. Although red wine may contain more proanthocyanidins by mass per unit of volume than does red grape juice, red grape juice contains more proanthocyanidins per average serving size. An eight US fluid ounces (240 ml) serving of grape juice averages 124 milligrams proanthocyanidins, whereas a five US fluid ounces (150 ml) serving of red wine averages 91 milligrams (
1979:
Taheri, Rod; Connolly, Bryan A.; Brand, Mark H.; Bolling, Bradley W. (2013). "Underutilized
Chokeberry (Aronia melanocarpa, Aronia arbutifolia, Aronia prunifolia) Accessions Are Rich Sources of Anthocyanins, Flavonoids, Hydroxycinnamic Acids, and Proanthocyanidins".
2287:
Vernhet, A.; Dubascoux, S. P.; Cabane, B.; Fulcrand, H. L. N.; Dubreucq, E.; Poncet-Legrand, C. L. (2011). "Characterization of oxidized tannins: Comparison of depolymerization methods, asymmetric flow field-flow fractionation and small-angle X-ray scattering".
2250:
Vernhet, A.; Dubascoux, S. P.; Cabane, B.; Fulcrand, H. L. N.; Dubreucq, E.; Poncet-Legrand, C. L. (2011). "Characterization of oxidized tannins: Comparison of depolymerization methods, asymmetric flow field-flow fractionation and small-angle X-ray scattering".
2690:
Sánchez-Moreno, Concepción; Cao, Guohua; Ou, Boxin; Prior, Ronald L. (2003). "Anthocyanin and
Proanthocyanidin Content in Selected White and Red Wines. Oxygen Radical Absorbance Capacity Comparison with Nontraditional Wines Obtained from Highbush Blueberry".
996:"Scientific Opinion on the substantiation of a health claim related to CranMax® and reduction of the risk of urinary tract infection by inhibiting the adhesion of certain bacteria in the urinary tract pursuant to Article 14 of Regulation (EC) No 1924/2006"
2126:
Matthews, S.; Mila, I.; Scalbert, A.; Pollet, B.; Lapierre, C.; Hervé Du
Penhoat, C. L. M.; Rolando, C.; Donnelly, D. M. X. (1997). "Method for Estimation of Proanthocyanidins Based on Their Acid Depolymerization in the Presence of Nucleophiles".
1749:
Stringano, E; Gea, A; Salminen, J. P.; Mueller-Harvey, I (2011). "Simple solution for a complex problem: Proanthocyanidins, galloyl glucoses and ellagitannins fit on a single calibration curve in high performance-gel permeation chromatography".
2380:
Douglas-Fir Bark: Characterization of a
Condensed Tannin Extract, by Hong-Keun Song, A thesis submitted to Oregon State University in partial fulfillment of the requirements for the degree of Master of Science, December 13,
2478:
Luís, Â; Domingues, F; Pereira, L (10 March 2017). "Can
Cranberries Contribute to Reduce the Incidence of Urinary Tract Infections? A Systematic Review with Meta-Analysis and Trial Sequential Analysis of Clinical Trials".
1018:
A cause and effect relationship has not been established between the consumption of CranMax® and reduction of the risk of urinary tract infection by inhibiting the adhesion of certain bacteria in the urinary
1785:
Engström, M. T.; Pälijärvi, M; Fryganas, C; Grabber, J. H.; Mueller-Harvey, I; Salminen, J. P. (2014). "Rapid
Qualitative and Quantitative Analyses of Proanthocyanidin Oligomers and Polymers by UPLC-MS/MS".
915:, 145.6 milligrams per 8 fl. oz. or 240 mL). Many other foods and beverages may also contain proanthocyanidins, but few attain the levels found in red grape seeds and skins, with a notable exception being
419:
is a dye that is particularly useful for localization of proanthocyanidin compounds in plant histology. The use of the reagent results in blue staining. It can also be used to titrate proanthocyanidins.
1239:
Pacheco-Palencia LA, Mertens-Talcott S, Talcott ST (Jun 2008). "Chemical composition, antioxidant properties, and thermal stability of a phytochemical enriched oil from Acai (Euterpe oleracea Mart.)".
882:"Current evidence is insufficient to support Pycnogenol(®) use for the treatment of any chronic disorder. Well-designed, adequately powered trials are needed to establish the value of this treatment."
821:
concluded that cranberry products significantly reduced the incidence of UTIs, indicating that cranberry products may be effective particularly for individuals with recurrent infections. In 2019, the
802:
have produced mixed results when asking the question to confirm that PACs, particularly from cranberries, were an alternative to antibiotic prophylaxis for UTIs: 1) a 2014 scientific opinion by the
1034:
Williams, Gabrielle; Stothart, Christopher I.; Hahn, Deirdre; Stephens, Jacqueline H.; Craig, Jonathan C.; Hodson, Elisabeth M. (2023-11-10). "Cranberries for preventing urinary tract infections".
1936:
Carpenter JL, Caruso FL, Tata A, Vorsa N, Neto CC (2014). "Variation in proanthocyanidin content and composition among commonly grown North
American cranberry cultivars (Vaccinium macrocarpon)".
1353:
Hatano, T; Miyatake, H; Natsume, M; Osakabe, N; Takizawa, T; Ito, H; Yoshida, T (2002). "Proanthocyanidin glycosides and related polyphenols from cacao liquor and their antioxidant effects".
722:
In general, reactions are made in methanol, especially thiolysis, as benzyl mercaptan has a low solubility in water. They involve a moderate (50 to 90 °C) heating for a few minutes.
1916:
2050:
Kandil, F. E.; Song, L.; Pezzuto, J. M.; Marley, K.; Seigler, D. S.; Smith, M. A. L. (2000). "Isolation of oligomeric proanthocyanidins from flavonoid-producing cell cultures".
2786:
Wu X, Gu L, Prior RL, McKay S (2004). "Characterization of anthocyanins and proanthocyanidins in some cultivars of Ribes, Aronia, and
Sambucus and their antioxidant capacity".
2157:
Liu, H; Zou, T; Gao, J. M.; Gu, L (2013). "Depolymerization of cranberry procyanidins using (+)-catechin, (-)-epicatechin, and (-)-epigallocatechin gallate as chain breakers".
529:
of purple or red pigmented plants contain large amounts of OPCs. They are dense in grape seeds and skin, and therefore in red wine and grape seed extract, cocoa, nuts and all
78:
Proanthocyanidins were discovered in 1947 by
Jacques Masquelier, who developed and patented techniques for the extraction of oligomeric proanthocyanidins from pine bark and
2015:
Rösch, Daniel R.; Mügge, Clemens; Fogliano, Vincenzo; Kroh, Lothar W. (2004). "Antioxidant
Oligomeric Proanthocyanidins from Sea Buckthorn (Hippophaë rhamnoides) Pomace".
2647:
Gonzalo-Diago, A; Dizy, M; Fernández-Zurbano, P (2013). "Taste and mouthfeel properties of red wines proanthocyanidins and their relation to the chemical composition".
2942:
1571:
825:
released guidelines stating that a moderate level of evidence supports the use of cranberry products containing PACs for possible prevention from recurrent UTIs.
3097:
98:
Proanthocyanidins, including the lesser bioactive and bioavailable polymers (four or more catechins), represent a group of condensed flavan-3-ols, such as
2824:
Grape seed extract, US National Institutes of Health, Office of Dietary Supplements, The National Center for Complementary and Alternative Medicine, 2014
2192:
Kennedy, J. A.; Jones, G. P. (2001). "Analysis of Proanthocyanidin Cleavage Products Following Acid-Catalysis in the Presence of Excess Phloroglucinol".
202:
bears 65–75 percent proanthocyanidins (procyanidins). Thus a 100 mg serving would contain 65 to 75 mg of proanthocyanidins (procyanidins).
2850:
1856:
Jorgensen, Emily M.; Marin, Anna B.; Kennedy, James A. (2004). "Analysis of the Oxidative Degradation of Proanthocyanidins under Basic Conditions".
406:
183:
Apples contain on average per serving about eight times the amount of proanthocyanidin found in wine, with some of the highest amounts found in the
1318:
Rohdewald, P (2002). "A review of the French maritime pine bark extract (Pycnogenol), a herbal medication with a diverse clinical pharmacology".
2604:
Absalon, C; Fabre, S; Tarascou, I; Fouquet, E; Pianet, I (2011). "New strategies to study the chemical nature of wine oligomeric procyanidins".
1396:
Merghem, R.; Jay, M.; Brun, N.; Voirin, B. (2004). "Qualitative analysis and HPLC isolation and identification of procyanidins fromvicia faba".
156:, and other plants also contain these flavonoids. Cocoa beans contain the highest concentrations. Proanthocyanidins also may be isolated from
3215:
711:
like methanol. The reaction leads to the formation of free and derived monomers that can be further analyzed or used to enhance procyanidin
3410:
465:
2394:"HPLC, NMR and MALDI-TOF MS Analysis of Condensed Tannins from Lithocarpus glaber Leaves with Potent Free Radical Scavenging Activity"
2379:
976:
1733:
692:
1523:
Qa’Dan, F.; Petereit, F.; Mansoor, K.; Nahrstedt, A. (2006). "Antioxidant oligomeric proanthocyanidins fromCistus salvifolius".
3921:
3090:
1663:
Cabrera, A.; Martin, A. (2009). "Genetics of tannin content and its relationship with flower and testa colours in Vicia faba".
822:
3847:
1139:
Souquet, J; Cheynier, Véronique; Brossaud, Franck; Moutounet, Michel (1996). "Polymeric proanthocyanidins from grape skins".
803:
1441:"The digestibility in piglets of faba bean (Vicia faba L.) as affected by breeding towards the absence of condensed tannins"
1821:
Torres, J. L.; Lozano, C. (2001). "Chromatographic characterization of proanthocyanidins after thiolysis with cysteamine".
1922:
1209:
712:
458:
2843:
729:
Phloroglucinolysis can be used for instance for proanthocyanidins characterisation in wine or in grape seeds and skin.
597:
410:
919:, which has the highest recorded level of proanthocyanidins among fruits assessed to date (664 milligrams per 100 g).
783:
have A2-type proanthocyanidins (PACs) which may be important for the ability of PACs to bind to proteins, such as the
3926:
3083:
948:
2443:
Howell, AB (2007). "Bioactive compounds in cranberries and their role in prevention or urinary tract infections".
3208:
732:
Thioglycolysis can be used to study proanthocyanidins or the oxidation of condensed tannins. It is also used for
628:
Proanthocyanidin has low bioavailability, with 90% remaining unabsorbed from the intestines until metabolized by
810:
evidence that cranberry PACs have a role in inhibiting bacterial pathogens involved in UTIs; 2) an updated 2023
3403:
1084:
Mateos-Martín ML, Fuguet E, Quero C, et al. (2012). "New identification of proanthocyanidins in cinnamon (
795:
499:
450:
1731:
Grape Seed Extract, White paper, The Grape Seed Method Evaluation Committee, Under the Auspices of NNFA ComPli
1569:
Luca SV, Macovei I, Bujor A, Trifan A (2020). "Bioactivity of dietary polyphenols: The role of metabolites".
3916:
3735:
3269:
3233:
2836:
933:
928:
83:
1616:"The Grapevine Transcription Factor VvMYBPA1 Regulates Proanthocyanidin Synthesis during Fruit Development"
3897:
3857:
3852:
834:
811:
791:
1480:
Griffiths, D. W. (1981). "The polyphenolic content and enzyme inhibitory activity of testas from bean (
1183:
833:
Proanthocyanidins are the principal polyphenols in red wine that are under research to assess risk of
3712:
3339:
3201:
2947:
2560:
1945:
1497:
1405:
1362:
1148:
3375:
3370:
3365:
3360:
3259:
2547:
Corder, R.; Mullen, W.; Khan, N. Q.; Marks, S. C.; Wood, E. G.; Carrier, M. J.; Crozier, A. (2006).
3556:
3396:
3313:
434:
236:
1891:
Li, Hui-Jing; Deinzer, Max L (2007). "Tandem mass spectrometry for sequencing proanthocyanidins".
521:
of catechins. OPCs are found in most plants and thus are common in the human diet. Especially the
3624:
3054:
2952:
2860:
2629:
2586:
2504:
2313:
2276:
2067:
1838:
1680:
1596:
1548:
1121:
759:
677:
515:
2227:
Sears, K. D.; Casebier, R. L. (1968). "Cleavage of proanthocyanidins with thioglycollic acid".
608:
In nature, proanthocyanidins serve among other chemical and induced defense mechanisms against
3806:
3135:
2803:
2765:
2747:
2708:
2672:
2621:
2578:
2496:
2460:
2425:
2362:
2333:"Elicitor-Induced Spruce Stress Lignin (Structural Similarity to Early Developmental Lignins)"
2305:
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1997:
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1873:
1803:
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1540:
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1421:
1378:
1335:
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1210:"Proanthocyanidins from Quercus petraea and Q. robur heartwood: quantification and structures"
1113:
1063:
1051:
972:
818:
814:
review supported the use of cranberry products for the prevention of UTIs for certain groups.
784:
700:
673:
657:
588:
511:
481:
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398:
640:
Condensed tannins can undergo acid-catalyzed cleavage in the presence of (or an excess of) a
3636:
3527:
3155:
3140:
3106:
2995:
2795:
2755:
2739:
2700:
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2613:
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2488:
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2415:
2405:
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2136:
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1989:
1953:
1900:
1865:
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1672:
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1505:
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1221:
1156:
1105:
1097:
1059:
1043:
1007:
688:
649:
485:
402:
372:
72:
82:. Proanthocyanidins are under preliminary research for the potential to reduce the risk of
3872:
3867:
3862:
3817:
3253:
3145:
3039:
2523:"Recurrent Uncomplicated Urinary Tract Infections in Women: AUA/CUA/SUFU Guideline (2019)"
1737:
716:
609:
231:
158:
2726:
Robertson, Nina U.; Schoonees, Anel; Brand, Amanda; Visser, Janicke (29 September 2020).
2564:
1949:
1730:
1501:
1439:
Van Der Poel, A. F. B.; Dellaert, L. M. W.; Van Norel, A.; Helsper, J. P. F. G. (2007).
1409:
1366:
1152:
71:. More complex polyphenols, having the same polymeric building block, form the group of
3877:
3747:
3703:
3332:
3326:
3320:
3308:
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3298:
3293:
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3283:
3278:
3247:
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3150:
3130:
3125:
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1640:
1615:
799:
708:
645:
564:
547:
518:
477:
217:
173:
132:
123:
102:, prodelphinidins and propelargonidins. They can be found in many plants, most notably
2823:
2357:
2332:
1374:
860:), was substantially higher (177 mg/L) than that in white wines (9 mg/L).
719:. The free monomers correspond to the terminal units of the condensed tannins chains.
3910:
3632:
3584:
3177:
3049:
2980:
2919:
2914:
2909:
2904:
2899:
2508:
1160:
869:
807:
751:
723:
580:
461:(GPC) analysis allows separation of monomers from larger proanthocyanidin molecules.
416:
227:
195:
184:
164:
145:
107:
2071:
1842:
1684:
1600:
1125:
3743:
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2170:
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522:
210:
188:
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17:
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3355:
3225:
3171:
3120:
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3023:
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2934:
2891:
853:
846:
763:
leaves have been analysed through acid-catalyzed degradation in the presence of
744:
740:
704:
665:
641:
556:
473:
99:
65:
61:
2492:
2085:
Amil-Ruiz, F.; Blanco-Portales, R.; Munoz-Blanco, J.; Caballero, J. L. (2011).
1225:
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3775:
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3613:
3481:
3064:
3005:
2617:
2410:
2301:
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2063:
1676:
1536:
1101:
943:
904:
874:
842:
764:
661:
537:
489:
472:. Condensed tannins can undergo acid-catalyzed cleavage in the presence of a
425:
222:
199:
169:
119:
79:
46:
34:
2751:
1700:"A non-destructive screening method for proanthocyanidin-free barley mutants"
1614:
Bogs, J.; Jaffe, F. W.; Takos, A. M.; Walker, A. R.; Robinson, S. P. (2007).
1292:
1275:
1055:
1012:
995:
3825:
3785:
3683:
3647:
3504:
3477:
3469:
3428:
3420:
3182:
2967:
1509:
1274:
Hammerstone, John F.; Lazarus, Sheryl A.; Schmitz, Harold H. (August 2000).
896:
780:
681:
653:
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493:
438:
282:
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153:
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53:
42:
38:
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2500:
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2213:
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2112:
2036:
2001:
1965:
1912:
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1544:
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1382:
1339:
1301:
1260:
1117:
1067:
2828:
2348:
1631:
1466:
3794:
3720:
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3600:
3580:
3571:
3500:
3454:
3018:
3013:
2957:
2876:
2868:
2236:
2103:
2086:
1184:"USDA Database for the Proanthocyanidin Content of Selected Foods – 2004"
892:
878:
were not found (in 2012) to be effective as a treatment for any disease:
748:
669:
600:
maintains a database of botanical and food sources of proanthocyanidins.
542:
382:
352:
327:
137:
127:
111:
87:
57:
50:
3193:
2668:
1457:
1440:
3762:
3458:
3446:
3059:
2924:
1834:
1716:
1699:
1208:
Vivas, N; Nonier, M; Pianet, I; Vivasdegaulejac, N; Fouquet, E (2006).
1109:
838:
576:
362:
3388:
2799:
2704:
2660:
2205:
2140:
2028:
1993:
1957:
1904:
1869:
1799:
1252:
496:) leading to the formation of oligomers that can be further analyzed.
3802:
3541:
3508:
2990:
1331:
938:
916:
908:
733:
568:
531:
430:
115:
3075:
2573:
2548:
1417:
464:
Monomers of proanthocyanidins can be characterized by analysis with
1276:"Procyanidin content and variation in some commonly consumed foods"
292:
272:
103:
68:
555:), along with many other pine species. OPCs also can be found in
302:
3392:
3197:
3079:
2832:
2728:"Pine bark (Pinus spp.) extract for treating chronic disorders"
1320:
International Journal of Clinical Pharmacology and Therapeutics
2087:"The Strawberry Plant Defense Mechanism: A Molecular Review"
1079:
1077:
535:
fruits (most concentrated in the skin), and in the bark of
794:
and were thought to inhibit bacterial infections, such as
437:, resulting in a red color of the test in the presence of
401:
may be characterised by a number of techniques including
707:
intermediate under strongly acidic conditions in polar
2331:
Lange, B. M.; Lapierre, C.; Sandermann Jr, H. (1995).
891:
Proanthocyanidins are present in fresh grapes, juice,
868:
Proanthocyanidins found in the proprietary extract of
2549:"Oenology: Red wine procyanidins and vascular health"
2052:
In Vitro Cellular & Developmental Biology - Plant
510:
Oligomeric proanthocyanidins (OPC) strictly refer to
3838:
3816:
3793:
3784:
3761:
3734:
3711:
3702:
3674:
3646:
3623:
3594:
3565:
3549:
3540:
3518:
3491:
3468:
3445:
3436:
3427:
3348:
3329:(epicatechin-(4β→8)-epicatechin-(4β→8)-epicatechin)
3268:
3232:
3164:
3113:
3032:
3004:
2966:
2933:
2890:
2867:
971:. Publishing rights search incomplete. p. 15.
586:Oligomeric proanthocyanidins can be extracted via
234:and could have an inhibitory activity on enzymes.
3323:(epicatechin-(4β→8)-epicatechin-(4β→6)-catechin)
86:(UTIs) by consuming cranberries, grape seeds or
2943:1,7-Bis(4-hydroxyphenyl)-1,4,6-heptatrien-3-one
1564:
1562:
1572:Critical Reviews in Food Science and Nutrition
1490:Journal of the Science of Food and Agriculture
180:), is rich in numerous procyanidin oligomers.
3404:
3209:
3091:
2844:
8:
1088:L.) using MALDI-TOF/TOF mass spectrometry".
895:, and other darkly pigmented fruits such as
444:Proanthocyanidins can be titrated using the
240:also contains oligomeric proanthocyanidins.
226:) contain proanthocyanidins that affect the
176:, obtained from the fruit of the açaí palm (
2732:The Cochrane Database of Systematic Reviews
1036:The Cochrane Database of Systematic Reviews
852:In red wines, total OPC content, including
502:can be used to sequence proanthocyanidins.
122:, grape seed, grape skin (procyanidins and
3790:
3708:
3546:
3442:
3433:
3411:
3397:
3389:
3335:(catechin-(4α→8)-catechin-(4α→8)-catechin)
3216:
3202:
3194:
3098:
3084:
3076:
2851:
2837:
2829:
2788:Journal of Agricultural and Food Chemistry
2693:Journal of Agricultural and Food Chemistry
2649:Journal of Agricultural and Food Chemistry
2194:Journal of Agricultural and Food Chemistry
2129:Journal of Agricultural and Food Chemistry
2017:Journal of Agricultural and Food Chemistry
1982:Journal of Agricultural and Food Chemistry
1858:Journal of Agricultural and Food Chemistry
1788:Journal of Agricultural and Food Chemistry
110:bark and that of most other pine species,
2759:
2572:
2419:
2409:
2356:
2102:
1715:
1639:
1456:
1291:
1011:
841:, they also influence the aroma, flavor,
695:or percentage of galloylation. These are
27:Class of polyphenols found in many plants
1178:
1176:
1174:
1172:
1170:
407:asymmetric flow field flow fractionation
242:
2529:. American Urological Association. 2019
959:
636:Non-oxidative chemical depolymerisation
2606:Analytical and Bioanalytical Chemistry
2290:Analytical and Bioanalytical Chemistry
2253:Analytical and Bioanalytical Chemistry
2152:
2150:
1090:Analytical and Bioanalytical Chemistry
990:
988:
687:These techniques are generally called
648:(reaction called phloroglucinolysis),
632:to the more bioavailable metabolites.
480:(reaction called phloroglucinolysis),
2781:
2779:
739:. Reaction on condensed tannins from
699:, a type of substitution reaction in
7:
1698:Kristensen, H.; Aastrup, S. (1986).
1029:
1027:
660:(reaction called thioglycolysis) or
423:Proanthocyanidins from field beans (
136:(the European wine grape). However,
1665:The Journal of Agricultural Science
837:and lower overall mortality. With
25:
2392:Zhang, L. L.; Lin, Y. M. (2008).
1704:Carlsberg Research Communications
693:average degree of polymerisation
672:produce short-chain procyanidin
3316:(ent-Epicatechin(4α→8)catechin)
823:American Urological Association
3848:List of phytochemicals in food
2744:10.1002/14651858.CD008294.pub5
2171:10.1016/j.foodchem.2013.03.003
1048:10.1002/14651858.CD001321.pub7
804:European Food Safety Authority
551:(pine bark; formerly known as
433:have been estimated using the
37:found in many plants, such as
1:
1585:10.1080/10408398.2018.1546669
1375:10.1016/S0031-9422(02)00051-1
691:and give information such as
459:Gel permeation chromatography
1764:10.1016/j.chroma.2011.08.082
1445:British Journal of Nutrition
1161:10.1016/0031-9422(96)00301-9
598:US Department of Agriculture
506:Oligomeric proanthocyanidins
411:small-angle X-ray scattering
1752:Journal of Chromatography A
684:which are more absorbable.
3943:
2493:10.1016/j.juro.2017.03.078
1226:10.1016/j.crci.2005.09.001
1006:(5): 3657 (11 pgs). 2014.
949:Phenolic compounds in wine
3895:
2618:10.1007/s00216-011-4988-1
2411:10.3390/molecules13122986
2302:10.1007/s00216-011-5076-2
2265:10.1007/s00216-011-5076-2
2091:Plant and Cell Physiology
2064:10.1007/s11627-000-0088-1
1677:10.1017/S0021859600084665
1537:10.1080/14786410600899225
1286:(8S Suppl): 2086S–2092S.
1102:10.1007/s00216-011-5557-3
967:Schwitters, Bert (1995).
3270:B type proanthocyanidins
3234:A-type proanthocyanidins
1525:Natural Product Research
1280:The Journal of Nutrition
1013:10.2903/j.efsa.2014.3657
796:urinary tract infections
776:Urinary tract infections
500:Tandem mass spectrometry
84:urinary tract infections
56:. Many are oligomers of
49:. Chemically, they are
3858:O-methylated flavonoids
3853:C-methylated flavonoids
2229:Chemical Communications
1510:10.1002/jsfa.2740320808
934:B type proanthocyanidin
929:A type proanthocyanidin
757:Condensed tannins from
168:heartwood (wine barrel
3922:Flavonoid antioxidants
3898:Flavonoid biosynthesis
3736:3-hydroxyanthocyanidin
2457:10.1002/mnfr.200700038
1398:Phytochemical Analysis
1293:10.1093/jn/130.8.2086S
835:coronary heart disease
812:Cochrane Collaboration
441:or proanthocyanidins.
94:Distribution in plants
3713:3-deoxyanthocyanidins
2349:10.1104/pp.108.3.1277
1632:10.1104/pp.106.093203
1214:Comptes Rendus Chimie
1086:Cinnamomum zeylanicum
209:can be isolated from
2948:Bisdemethoxycurcumin
2237:10.1039/C19680001437
1893:Analytical Chemistry
668:compounds used with
616:, such as occurs in
2565:2006Natur.444..566C
1950:2014JSFA...94.2738C
1502:1981JSFA...32..797G
1458:10.1079/BJN19920134
1410:2004PChAn..15...95M
1367:2002PChem..59..749H
1153:1996PChem..43..509S
446:Procyanidolic Index
435:vanillin-HCl method
237:Cistus salviifolius
3136:Proguibourtinidins
3055:Phycoerythrocyanin
2953:Desmethoxycurcumin
2481:Journal of Urology
2104:10.1093/pcp/pcr136
1835:10.1007/BF02491211
1736:2002-12-24 at the
1717:10.1007/BF02906893
1488:spp.) varieties".
760:Lithocarpus glaber
596:cell culture. The
492:(processes called
484:(thioglycolysis),
3927:Condensed tannins
3904:
3903:
3891:
3890:
3834:
3833:
3807:Isoliquiritigenin
3757:
3756:
3698:
3697:
3536:
3535:
3386:
3385:
3338:Tetramers :
3191:
3190:
3156:Proteracacinidins
3141:Promelacacinidins
3107:Condensed tannins
3073:
3072:
2996:Condensed tannins
2800:10.1021/jf0486850
2794:(26): 7846–7856.
2705:10.1021/jf030081t
2699:(17): 4889–4896.
2661:10.1021/jf401041q
2655:(37): 8861–8870.
2445:Mol Nutr Food Res
2404:(12): 2986–2997.
2206:10.1021/jf001030o
2141:10.1021/jf9607573
2097:(11): 1873–1903.
2029:10.1021/jf040241g
2023:(22): 6712–6718.
1994:10.1021/jf402449q
1988:(36): 8581–8588.
1958:10.1002/jsfa.6618
1944:(13): 2738–2745.
1905:10.1021/ac061823v
1870:10.1021/jf035311i
1800:10.1021/jf500745y
1794:(15): 3390–3399.
1758:(43): 7804–7812.
1531:(13): 1216–1224.
1253:10.1021/jf800161u
1247:(12): 4631–4636.
1241:J Agric Food Chem
819:systematic review
701:organic chemistry
658:thioglycolic acid
652:(reaction called
589:Vaccinium pahalae
482:thioglycolic acid
470:mass spectrometry
448:(also called the
399:Condensed tannins
391:
390:
249:Proanthocyanidin
205:Proanthocyanidin
73:condensed tannins
31:Proanthocyanidins
18:Proanthocyanidins
16:(Redirected from
3934:
3873:Prenylflavonoids
3868:Pyranoflavonoids
3863:Furanoflavonoids
3791:
3709:
3637:Leucodelphinidin
3625:Flavan-3,4-diols
3547:
3528:Dalbergichromene
3443:
3434:
3413:
3406:
3399:
3390:
3218:
3211:
3204:
3195:
3146:Propelargonidins
3100:
3093:
3086:
3077:
2853:
2846:
2839:
2830:
2812:
2811:
2783:
2774:
2773:
2763:
2723:
2717:
2716:
2687:
2681:
2680:
2644:
2638:
2637:
2612:(5): 1485–1495.
2601:
2595:
2594:
2576:
2544:
2538:
2537:
2535:
2534:
2519:
2513:
2512:
2475:
2469:
2468:
2440:
2434:
2433:
2423:
2413:
2389:
2383:
2377:
2371:
2370:
2360:
2343:(3): 1277–1287.
2337:Plant Physiology
2328:
2322:
2321:
2296:(5): 1559–1569.
2284:
2259:(5): 1559–1569.
2247:
2241:
2240:
2224:
2218:
2217:
2200:(4): 1740–1746.
2189:
2183:
2182:
2154:
2145:
2144:
2135:(4): 1195–1201.
2123:
2117:
2116:
2106:
2082:
2076:
2075:
2047:
2041:
2040:
2012:
2006:
2005:
1976:
1970:
1969:
1938:J Sci Food Agric
1933:
1927:
1926:
1921:
1899:(4): 1739–1748.
1888:
1882:
1881:
1864:(8): 2292–2296.
1853:
1847:
1846:
1829:(7–8): 523–526.
1818:
1812:
1811:
1782:
1776:
1775:
1746:
1740:
1728:
1722:
1721:
1719:
1695:
1689:
1688:
1660:
1654:
1653:
1643:
1626:(3): 1347–1361.
1620:Plant Physiology
1611:
1605:
1604:
1566:
1557:
1556:
1520:
1514:
1513:
1477:
1471:
1470:
1460:
1436:
1430:
1429:
1393:
1387:
1386:
1350:
1344:
1343:
1332:10.5414/cpp40158
1315:
1309:
1308:
1295:
1271:
1265:
1264:
1236:
1230:
1229:
1205:
1199:
1198:
1196:
1194:
1188:
1180:
1165:
1164:
1136:
1130:
1129:
1096:(3): 1327–1336.
1081:
1072:
1071:
1062: 10636779.
1042:(11): CD001321.
1031:
1022:
1021:
1015:
992:
983:
982:
964:
829:Wine consumption
689:depolymerisation
650:benzyl mercaptan
486:benzyl mercaptan
403:depolymerisation
373:Baking chocolate
243:
220:of field beans (
178:Euterpe oleracea
21:
3942:
3941:
3937:
3936:
3935:
3933:
3932:
3931:
3907:
3906:
3905:
3900:
3887:
3830:
3818:Dihydrochalcone
3812:
3780:
3753:
3730:
3694:
3670:
3642:
3619:
3598:
3590:
3569:
3561:
3532:
3514:
3487:
3464:
3423:
3417:
3387:
3382:
3344:
3340:Cinnamtannin A2
3264:
3254:Cinnamtannin B1
3228:
3222:
3192:
3187:
3174:(phlobatannins)
3160:
3151:Prorobinetidins
3131:Profisetinidins
3126:Prodelphinidins
3109:
3104:
3074:
3069:
3040:Allophycocyanin
3028:
3000:
2962:
2929:
2886:
2863:
2857:
2820:
2815:
2785:
2784:
2777:
2738:(9): CD008294.
2725:
2724:
2720:
2689:
2688:
2684:
2646:
2645:
2641:
2603:
2602:
2598:
2574:10.1038/444566a
2546:
2545:
2541:
2532:
2530:
2521:
2520:
2516:
2477:
2476:
2472:
2442:
2441:
2437:
2391:
2390:
2386:
2378:
2374:
2330:
2329:
2325:
2286:
2249:
2248:
2244:
2226:
2225:
2221:
2191:
2190:
2186:
2156:
2155:
2148:
2125:
2124:
2120:
2084:
2083:
2079:
2049:
2048:
2044:
2014:
2013:
2009:
1978:
1977:
1973:
1935:
1934:
1930:
1919:
1890:
1889:
1885:
1855:
1854:
1850:
1823:Chromatographia
1820:
1819:
1815:
1784:
1783:
1779:
1748:
1747:
1743:
1738:Wayback Machine
1729:
1725:
1697:
1696:
1692:
1662:
1661:
1657:
1613:
1612:
1608:
1568:
1567:
1560:
1522:
1521:
1517:
1479:
1478:
1474:
1438:
1437:
1433:
1418:10.1002/pca.731
1395:
1394:
1390:
1352:
1351:
1347:
1317:
1316:
1312:
1273:
1272:
1268:
1238:
1237:
1233:
1207:
1206:
1202:
1192:
1190:
1186:
1182:
1181:
1168:
1138:
1137:
1133:
1083:
1082:
1075:
1033:
1032:
1025:
994:
993:
986:
979:
969:OPC in Practice
966:
965:
961:
957:
925:
889:
866:
831:
800:Clinical trials
778:
773:
717:bioavailability
709:protic solvents
638:
626:
624:Bioavailability
610:plant pathogens
606:
519:polymerizations
508:
396:
246:Dietary source
159:Quercus petraea
124:prodelphinidins
96:
33:are a class of
28:
23:
22:
15:
12:
11:
5:
3940:
3938:
3930:
3929:
3924:
3919:
3917:Food chemistry
3909:
3908:
3902:
3901:
3896:
3893:
3892:
3889:
3888:
3886:
3885:
3880:
3878:Methylenedioxy
3875:
3870:
3865:
3860:
3855:
3850:
3844:
3842:
3836:
3835:
3832:
3831:
3829:
3828:
3822:
3820:
3814:
3813:
3811:
3810:
3799:
3797:
3788:
3782:
3781:
3779:
3778:
3773:
3767:
3765:
3759:
3758:
3755:
3754:
3752:
3751:
3748:Guibourtinidin
3740:
3738:
3732:
3731:
3729:
3728:
3717:
3715:
3706:
3704:Anthocyanidins
3700:
3699:
3696:
3695:
3693:
3692:
3686:
3680:
3678:
3672:
3671:
3669:
3668:
3663:
3658:
3652:
3650:
3644:
3643:
3641:
3640:
3629:
3627:
3621:
3620:
3618:
3617:
3606:
3604:
3592:
3591:
3589:
3588:
3577:
3575:
3563:
3562:
3560:
3559:
3553:
3551:
3544:
3538:
3537:
3534:
3533:
3531:
3530:
3524:
3522:
3516:
3515:
3513:
3512:
3497:
3495:
3489:
3488:
3486:
3485:
3474:
3472:
3466:
3465:
3463:
3462:
3451:
3449:
3440:
3431:
3425:
3424:
3418:
3416:
3415:
3408:
3401:
3393:
3384:
3383:
3381:
3380:
3379:
3378:
3376:Arecatannin C1
3373:
3371:Arecatannin B2
3368:
3366:Arecatannin A3
3363:
3361:Arecatannin A1
3352:
3350:
3346:
3345:
3343:
3342:
3336:
3333:Procyanidin C2
3330:
3327:Procyanidin C1
3324:
3321:Arecatannin B1
3317:
3311:
3306:
3301:
3296:
3291:
3286:
3281:
3279:Procyanidin B1
3277:Dimers :
3274:
3272:
3266:
3265:
3263:
3262:
3260:Arecatannin A2
3256:
3250:
3245:
3243:Procyanidin A1
3241:Dimers :
3238:
3236:
3230:
3229:
3223:
3221:
3220:
3213:
3206:
3198:
3189:
3188:
3186:
3185:
3180:
3178:Tannin sources
3175:
3168:
3166:
3162:
3161:
3159:
3158:
3153:
3148:
3143:
3138:
3133:
3128:
3123:
3117:
3115:
3111:
3110:
3105:
3103:
3102:
3095:
3088:
3080:
3071:
3070:
3068:
3067:
3062:
3057:
3052:
3047:
3042:
3036:
3034:
3030:
3029:
3027:
3026:
3021:
3016:
3010:
3008:
3002:
3001:
2999:
2998:
2993:
2988:
2983:
2981:Anthocyanidins
2978:
2972:
2970:
2964:
2963:
2961:
2960:
2955:
2950:
2945:
2939:
2937:
2931:
2930:
2928:
2927:
2922:
2917:
2912:
2907:
2902:
2896:
2894:
2888:
2887:
2885:
2884:
2879:
2873:
2871:
2865:
2864:
2861:plant pigments
2858:
2856:
2855:
2848:
2841:
2833:
2827:
2826:
2819:
2818:External links
2816:
2814:
2813:
2775:
2718:
2682:
2639:
2596:
2539:
2527:www.auanet.org
2514:
2487:(3): 614–621.
2470:
2451:(6): 732–737.
2435:
2384:
2372:
2323:
2242:
2219:
2184:
2165:(1): 488–494.
2159:Food Chemistry
2146:
2118:
2077:
2058:(6): 492–500.
2042:
2007:
1971:
1928:
1883:
1848:
1813:
1777:
1741:
1723:
1710:(7): 509–513.
1690:
1655:
1606:
1579:(4): 626–659.
1558:
1515:
1496:(8): 797–804.
1472:
1451:(3): 793–800.
1431:
1388:
1361:(7): 749–758.
1355:Phytochemistry
1345:
1326:(4): 158–168.
1310:
1266:
1231:
1200:
1166:
1147:(2): 509–512.
1141:Phytochemistry
1131:
1073:
1023:
984:
978:978-8886035132
977:
958:
956:
953:
952:
951:
946:
941:
936:
931:
924:
921:
888:
885:
884:
883:
865:
862:
849:of red wines.
830:
827:
777:
774:
772:
769:
752:thioglycolates
743:bark produces
703:, involving a
646:phloroglucinol
637:
634:
625:
622:
605:
602:
565:procyanidin A2
553:Pinus maritima
548:Pinus pinaster
507:
504:
478:phloroglucinol
395:
392:
389:
388:
385:
379:
378:
375:
369:
368:
365:
363:Sorghum grains
359:
358:
355:
349:
348:
346:
340:
339:
337:
334:
333:
330:
324:
323:
321:
315:
314:
312:
309:
308:
305:
299:
298:
295:
289:
288:
285:
279:
278:
275:
269:
268:
266:
260:
259:
257:
254:
253:
247:
194:An extract of
133:Vitis vinifera
95:
92:
26:
24:
14:
13:
10:
9:
6:
4:
3:
2:
3939:
3928:
3925:
3923:
3920:
3918:
3915:
3914:
3912:
3899:
3894:
3884:
3881:
3879:
3876:
3874:
3871:
3869:
3866:
3864:
3861:
3859:
3856:
3854:
3851:
3849:
3846:
3845:
3843:
3841:
3840:Miscellaneous
3837:
3827:
3824:
3823:
3821:
3819:
3815:
3808:
3804:
3801:
3800:
3798:
3796:
3792:
3789:
3787:
3783:
3777:
3774:
3772:
3769:
3768:
3766:
3764:
3760:
3749:
3745:
3742:
3741:
3739:
3737:
3733:
3726:
3722:
3719:
3718:
3716:
3714:
3710:
3707:
3705:
3701:
3690:
3687:
3685:
3682:
3681:
3679:
3677:
3673:
3667:
3664:
3662:
3659:
3657:
3654:
3653:
3651:
3649:
3645:
3638:
3634:
3633:Leucocyanidin
3631:
3630:
3628:
3626:
3622:
3615:
3611:
3608:
3607:
3605:
3602:
3597:
3593:
3586:
3585:Gallocatechol
3582:
3579:
3578:
3576:
3573:
3568:
3564:
3558:
3557:Luteoliflavan
3555:
3554:
3552:
3548:
3545:
3543:
3539:
3529:
3526:
3525:
3523:
3521:
3520:Neoflavonoids
3517:
3510:
3506:
3502:
3499:
3498:
3496:
3494:
3490:
3483:
3479:
3476:
3475:
3473:
3471:
3467:
3460:
3456:
3453:
3452:
3450:
3448:
3444:
3441:
3439:
3438:Anthoxanthins
3435:
3432:
3430:
3426:
3422:
3414:
3409:
3407:
3402:
3400:
3395:
3394:
3391:
3377:
3374:
3372:
3369:
3367:
3364:
3362:
3359:
3358:
3357:
3354:
3353:
3351:
3347:
3341:
3337:
3334:
3331:
3328:
3325:
3322:
3318:
3315:
3312:
3310:
3307:
3305:
3302:
3300:
3297:
3295:
3292:
3290:
3287:
3285:
3282:
3280:
3276:
3275:
3273:
3271:
3267:
3261:
3257:
3255:
3251:
3249:
3246:
3244:
3240:
3239:
3237:
3235:
3231:
3227:
3219:
3214:
3212:
3207:
3205:
3200:
3199:
3196:
3184:
3181:
3179:
3176:
3173:
3170:
3169:
3167:
3163:
3157:
3154:
3152:
3149:
3147:
3144:
3142:
3139:
3137:
3134:
3132:
3129:
3127:
3124:
3122:
3119:
3118:
3116:
3112:
3108:
3101:
3096:
3094:
3089:
3087:
3082:
3081:
3078:
3066:
3063:
3061:
3058:
3056:
3053:
3051:
3050:Phycoerythrin
3048:
3046:
3043:
3041:
3038:
3037:
3035:
3031:
3025:
3022:
3020:
3017:
3015:
3012:
3011:
3009:
3007:
3003:
2997:
2994:
2992:
2989:
2987:
2986:Anthoxanthins
2984:
2982:
2979:
2977:
2974:
2973:
2971:
2969:
2965:
2959:
2956:
2954:
2951:
2949:
2946:
2944:
2941:
2940:
2938:
2936:
2932:
2926:
2923:
2921:
2920:Chlorophyll f
2918:
2916:
2915:Chlorophyll d
2913:
2911:
2910:Chlorophyll c
2908:
2906:
2905:Chlorophyll b
2903:
2901:
2900:Chlorophyll a
2898:
2897:
2895:
2893:
2889:
2883:
2880:
2878:
2875:
2874:
2872:
2870:
2866:
2862:
2854:
2849:
2847:
2842:
2840:
2835:
2834:
2831:
2825:
2822:
2821:
2817:
2809:
2805:
2801:
2797:
2793:
2789:
2782:
2780:
2776:
2771:
2767:
2762:
2757:
2753:
2749:
2745:
2741:
2737:
2733:
2729:
2722:
2719:
2714:
2710:
2706:
2702:
2698:
2694:
2686:
2683:
2678:
2674:
2670:
2666:
2662:
2658:
2654:
2650:
2643:
2640:
2635:
2631:
2627:
2623:
2619:
2615:
2611:
2607:
2600:
2597:
2592:
2588:
2584:
2580:
2575:
2570:
2566:
2562:
2559:(7119): 566.
2558:
2554:
2550:
2543:
2540:
2528:
2524:
2518:
2515:
2510:
2506:
2502:
2498:
2494:
2490:
2486:
2482:
2474:
2471:
2466:
2462:
2458:
2454:
2450:
2446:
2439:
2436:
2431:
2427:
2422:
2417:
2412:
2407:
2403:
2399:
2395:
2388:
2385:
2382:
2376:
2373:
2368:
2364:
2359:
2354:
2350:
2346:
2342:
2338:
2334:
2327:
2324:
2319:
2315:
2311:
2307:
2303:
2299:
2295:
2291:
2282:
2278:
2274:
2270:
2266:
2262:
2258:
2254:
2246:
2243:
2238:
2234:
2230:
2223:
2220:
2215:
2211:
2207:
2203:
2199:
2195:
2188:
2185:
2180:
2176:
2172:
2168:
2164:
2160:
2153:
2151:
2147:
2142:
2138:
2134:
2130:
2122:
2119:
2114:
2110:
2105:
2100:
2096:
2092:
2088:
2081:
2078:
2073:
2069:
2065:
2061:
2057:
2053:
2046:
2043:
2038:
2034:
2030:
2026:
2022:
2018:
2011:
2008:
2003:
1999:
1995:
1991:
1987:
1983:
1975:
1972:
1967:
1963:
1959:
1955:
1951:
1947:
1943:
1939:
1932:
1929:
1924:
1918:
1914:
1910:
1906:
1902:
1898:
1894:
1887:
1884:
1879:
1875:
1871:
1867:
1863:
1859:
1852:
1849:
1844:
1840:
1836:
1832:
1828:
1824:
1817:
1814:
1809:
1805:
1801:
1797:
1793:
1789:
1781:
1778:
1773:
1769:
1765:
1761:
1757:
1753:
1745:
1742:
1739:
1735:
1732:
1727:
1724:
1718:
1713:
1709:
1705:
1701:
1694:
1691:
1686:
1682:
1678:
1674:
1670:
1666:
1659:
1656:
1651:
1647:
1642:
1637:
1633:
1629:
1625:
1621:
1617:
1610:
1607:
1602:
1598:
1594:
1590:
1586:
1582:
1578:
1574:
1573:
1565:
1563:
1559:
1554:
1550:
1546:
1542:
1538:
1534:
1530:
1526:
1519:
1516:
1511:
1507:
1503:
1499:
1495:
1491:
1487:
1483:
1476:
1473:
1468:
1464:
1459:
1454:
1450:
1446:
1442:
1435:
1432:
1427:
1423:
1419:
1415:
1411:
1407:
1403:
1399:
1392:
1389:
1384:
1380:
1376:
1372:
1368:
1364:
1360:
1356:
1349:
1346:
1341:
1337:
1333:
1329:
1325:
1321:
1314:
1311:
1307:
1303:
1299:
1294:
1289:
1285:
1281:
1277:
1270:
1267:
1262:
1258:
1254:
1250:
1246:
1242:
1235:
1232:
1227:
1223:
1219:
1215:
1211:
1204:
1201:
1185:
1179:
1177:
1175:
1173:
1171:
1167:
1162:
1158:
1154:
1150:
1146:
1142:
1135:
1132:
1127:
1123:
1119:
1115:
1111:
1107:
1103:
1099:
1095:
1091:
1087:
1080:
1078:
1074:
1069:
1065:
1061:
1057:
1053:
1049:
1045:
1041:
1037:
1030:
1028:
1024:
1020:
1014:
1009:
1005:
1001:
997:
991:
989:
985:
980:
974:
970:
963:
960:
954:
950:
947:
945:
942:
940:
937:
935:
932:
930:
927:
926:
922:
920:
918:
914:
910:
906:
902:
898:
894:
886:
881:
880:
879:
877:
876:
871:
870:maritime pine
863:
861:
859:
855:
850:
848:
844:
840:
836:
828:
826:
824:
820:
815:
813:
809:
808:physiological
805:
801:
797:
793:
790:
786:
782:
775:
770:
768:
766:
762:
761:
755:
753:
750:
746:
742:
738:
735:
730:
727:
725:
724:Epimerisation
720:
718:
714:
710:
706:
702:
698:
697:SN1 reactions
694:
690:
685:
683:
679:
675:
671:
667:
663:
659:
655:
651:
647:
643:
635:
633:
631:
623:
621:
619:
615:
611:
604:Plant defense
603:
601:
599:
595:
591:
590:
584:
582:
581:sea buckthorn
578:
574:
570:
566:
562:
558:
554:
550:
549:
544:
540:
539:
534:
533:
528:
525:, seeds, and
524:
520:
517:
513:
505:
503:
501:
497:
495:
491:
487:
483:
479:
475:
471:
467:
462:
460:
456:
454:
452:
447:
442:
440:
436:
432:
428:
427:
421:
418:
414:
412:
408:
404:
400:
393:
386:
384:
381:
380:
376:
374:
371:
370:
366:
364:
361:
360:
356:
354:
353:Cinnamon bark
351:
350:
347:
345:
342:
341:
338:
336:
335:
331:
329:
326:
325:
322:
320:
317:
316:
313:
311:
310:
306:
304:
301:
300:
296:
294:
291:
290:
286:
284:
281:
280:
276:
274:
271:
270:
267:
265:
262:
261:
258:
256:
255:
252:
248:
245:
244:
241:
239:
238:
233:
229:
228:digestibility
225:
224:
219:
214:
212:
208:
203:
201:
197:
196:maritime pine
192:
190:
186:
185:Red Delicious
181:
179:
175:
171:
167:
166:
161:
160:
155:
151:
147:
146:black currant
143:
139:
135:
134:
129:
125:
121:
117:
113:
109:
108:maritime pine
105:
101:
93:
91:
89:
85:
81:
76:
74:
70:
67:
63:
59:
55:
52:
48:
44:
40:
36:
32:
19:
3839:
3744:Apigeninidin
3689:Aromadendrin
3596:Flavan-4-ols
3567:Flavan-3-ols
3356:Arecatannins
3226:procyanidins
3172:Phlobaphenes
3121:Procyanidins
3024:Xanthophylls
2976:Anthocyanins
2935:Curcuminoids
2882:Betaxanthins
2791:
2787:
2735:
2731:
2721:
2696:
2692:
2685:
2669:10261/144130
2652:
2648:
2642:
2609:
2605:
2599:
2556:
2552:
2542:
2531:. Retrieved
2526:
2517:
2484:
2480:
2473:
2448:
2444:
2438:
2401:
2397:
2387:
2375:
2340:
2336:
2326:
2293:
2289:
2256:
2252:
2245:
2231:(22): 1437.
2228:
2222:
2197:
2193:
2187:
2162:
2158:
2132:
2128:
2121:
2094:
2090:
2080:
2055:
2051:
2045:
2020:
2016:
2010:
1985:
1981:
1974:
1941:
1937:
1931:
1896:
1892:
1886:
1861:
1857:
1851:
1826:
1822:
1816:
1791:
1787:
1780:
1755:
1751:
1744:
1726:
1707:
1703:
1693:
1668:
1664:
1658:
1623:
1619:
1609:
1576:
1570:
1528:
1524:
1518:
1493:
1489:
1485:
1481:
1475:
1448:
1444:
1434:
1404:(2): 95–99.
1401:
1397:
1391:
1358:
1354:
1348:
1323:
1319:
1313:
1305:
1283:
1279:
1269:
1244:
1240:
1234:
1217:
1213:
1203:
1191:. Retrieved
1189:. USDA. 2004
1144:
1140:
1134:
1093:
1089:
1085:
1039:
1035:
1017:
1003:
1000:EFSA Journal
999:
968:
962:
912:
901:blackcurrant
890:
873:
872:bark called
867:
857:
854:flavan-3-ols
851:
832:
816:
788:
779:
758:
756:
737:quantitation
731:
728:
726:may happen.
721:
686:
639:
627:
618:strawberries
607:
593:
587:
585:
552:
546:
536:
530:
509:
498:
463:
457:
449:
445:
443:
424:
422:
415:
397:
343:
318:
263:
250:
235:
221:
215:
211:cocoa liquor
204:
198:bark called
193:
189:Granny Smith
182:
177:
163:
157:
131:
100:procyanidins
97:
77:
30:
29:
3883:Castavinols
3725:Delphinidin
3676:Flavanonols
3666:Eriodictyol
3493:Isoflavones
3258:Tetramers:
3065:Xanthonoids
3045:Phycocyanin
3006:Carotenoids
2892:Chlorophyll
2877:Betacyanins
1484:) and pea (
1220:: 120–126.
1110:10261/88579
847:astringency
787:present on
781:Cranberries
745:epicatechin
741:Douglas fir
705:carbocation
666:Flavan-3-ol
642:nucleophile
561:cranberries
557:blueberries
474:nucleophile
451:Bates-Smith
283:Blueberries
273:Grape seeds
191:varieties.
120:cocoa beans
80:grape seeds
66:gallic acid
62:epicatechin
47:grape seeds
35:polyphenols
3911:Categories
3776:Leptosidin
3771:Aureusidin
3661:Naringenin
3656:Hesperidin
3648:Flavanones
3614:Luteoforol
3482:Kaempferol
3429:Flavonoids
3421:flavonoids
2968:Flavonoids
2533:2019-11-11
1482:Vicia faba
955:References
944:Polyphenol
905:elderberry
875:Pycnogenol
843:mouth-feel
765:cysteamine
713:absorption
662:cysteamine
538:Cinnamomum
527:seed coats
490:cysteamine
426:Vicia faba
251:(mg/100g)
223:Vicia faba
207:glycosides
200:Pycnogenol
64:and their
54:flavonoids
51:oligomeric
3826:Phloretin
3795:Chalcones
3786:Chalcones
3684:Taxifolin
3601:flavanols
3572:flavanols
3505:Genistein
3478:Quercetin
3470:Flavonols
3419:Types of
3319:Trimers:
3224:Types of
3183:Tannosome
3114:Oligomers
3019:Retinoids
3014:Carotenes
2869:Betalains
2859:Types of
2752:1469-493X
2509:206632675
2398:Molecules
1671:: 93–98.
1056:1469-493X
897:cranberry
858:catechins
806:rejected
682:tetramers
654:thiolysis
630:gut flora
614:predators
563:(notably
494:thiolysis
439:catechins
328:Hazelnuts
216:The seed
154:black tea
150:green tea
142:cranberry
128:red wines
43:blueberry
39:cranberry
3721:Cyanidin
3610:Apiforol
3581:Catechin
3501:Daidzein
3455:Apigenin
3447:Flavones
3252:Trimers:
3060:Quinones
2958:Curcumin
2808:15612766
2770:32990945
2713:12903941
2677:23889258
2626:21573848
2583:17136085
2501:28288837
2465:17487930
2430:19052523
2367:12228544
2310:21573842
2273:21573842
2214:11308320
2179:23768384
2113:21984602
2072:25781920
2037:15506806
2002:23941506
1966:24532348
1923:18534021
1913:17297981
1878:15080635
1843:95355684
1808:24665824
1772:21930278
1734:Archived
1685:84456901
1650:17208963
1601:58651581
1593:30614249
1545:17127512
1426:15116939
1383:11909632
1340:11996210
1306:Figure 5
1302:10917927
1261:18522407
1193:24 April
1126:23120410
1118:22101466
1068:37947276
923:See also
893:red wine
798:(UTIs).
792:fimbriae
785:adhesins
771:Research
749:catechin
670:methanol
594:in vitro
573:hawthorn
543:cinnamon
394:Analysis
383:Red wine
174:Açaí oil
165:Q. robur
138:bilberry
112:cinnamon
88:red wine
58:catechin
3809:, et.c.
3763:Aurones
3750:, et.c.
3727:, et.c.
3691:, et.c.
3639:, et.c.
3616:, et.c.
3587:, et.c.
3542:Flavans
3484:, et.c.
3461:, et.c.
3459:Chrysin
2991:Flavans
2925:Chlorin
2761:8094515
2634:8145537
2591:4303406
2561:Bibcode
2421:6245341
2318:4645218
2281:4645218
1946:Bibcode
1641:1820911
1498:Bibcode
1467:1493141
1406:Bibcode
1363:Bibcode
1149:Bibcode
887:Sources
839:tannins
817:A 2017
789:E. coli
678:trimers
577:rosehip
297:70–141
232:piglets
126:), and
118:fruit,
3803:Butein
3550:Flavan
3509:Orobol
2806:
2768:
2758:
2750:
2711:
2675:
2632:
2624:
2589:
2581:
2553:Nature
2507:
2499:
2463:
2428:
2418:
2365:
2358:157483
2355:
2316:
2308:
2279:
2271:
2212:
2177:
2111:
2070:
2035:
2000:
1964:
1920:
1911:
1876:
1841:
1806:
1770:
1683:
1648:
1638:
1599:
1591:
1553:254865
1551:
1543:
1465:
1424:
1381:
1338:
1300:
1259:
1124:
1116:
1066:
1054:
975:
939:Tannin
917:aronia
909:aronia
907:, and
734:lignin
674:dimers
579:, and
569:aronia
545:) and
532:Prunus
516:trimer
431:barley
307:32–42
293:Apples
264:Fruits
218:testas
116:aronia
104:apples
69:esters
45:, and
3511:et.c.
3349:Types
3165:Misc.
3033:Other
2630:S2CID
2587:S2CID
2505:S2CID
2314:S2CID
2277:S2CID
2068:S2CID
1917:INIST
1839:S2CID
1681:S2CID
1597:S2CID
1549:S2CID
1486:Pisum
1187:(PDF)
1122:S2CID
1019:tract
864:Other
680:, or
644:like
592:from
512:dimer
476:like
453:Assay
429:) or
417:DMACA
377:1636
367:3965
357:8108
344:Other
303:Pears
277:3532
2804:PMID
2766:PMID
2748:ISSN
2736:2020
2709:PMID
2673:PMID
2622:PMID
2579:PMID
2497:PMID
2461:PMID
2426:PMID
2381:1984
2363:PMID
2306:PMID
2269:PMID
2210:PMID
2175:PMID
2109:PMID
2033:PMID
1998:PMID
1962:PMID
1909:PMID
1874:PMID
1804:PMID
1768:PMID
1756:1218
1646:PMID
1589:PMID
1541:PMID
1463:PMID
1422:PMID
1379:PMID
1336:PMID
1298:PMID
1257:PMID
1195:2014
1114:PMID
1064:PMID
1052:ISSN
1040:2023
973:ISBN
913:i.e.
845:and
747:and
715:and
612:and
523:skin
514:and
468:and
466:HPLC
387:313
332:501
319:Nuts
287:332
187:and
170:oaks
162:and
60:and
2796:doi
2756:PMC
2740:doi
2701:doi
2665:hdl
2657:doi
2614:doi
2610:401
2569:doi
2557:444
2489:doi
2485:198
2453:doi
2416:PMC
2406:doi
2353:PMC
2345:doi
2341:108
2298:doi
2294:401
2261:doi
2257:401
2233:doi
2202:doi
2167:doi
2163:141
2137:doi
2099:doi
2060:doi
2025:doi
1990:doi
1954:doi
1901:doi
1866:doi
1831:doi
1796:doi
1760:doi
1712:doi
1673:doi
1669:113
1636:PMC
1628:doi
1624:143
1581:doi
1533:doi
1506:doi
1453:doi
1414:doi
1371:doi
1328:doi
1288:doi
1284:130
1249:doi
1222:doi
1157:doi
1106:hdl
1098:doi
1094:402
1060:PMC
1044:doi
1008:doi
656:),
567:),
488:or
409:or
230:in
172:).
130:of
3913::
3805:,
3746:,
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