Knowledge (XXG)

Polyphenol

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2276: 1158:. For water-soluble polyphenols, molecular weights between 500 and 3000 were reported to be required for protein precipitation. However, smaller molecules might still have astringent qualities likely due to the formation of unprecipitated complexes with proteins or cross-linking of proteins with simple phenols that have 1,2-dihydroxy or 1,2,3-trihydroxy groups. Flavonoid configurations can also cause significant differences in sensory properties, e.g. 399: 337: 516: 207: 33: 481: 143: 614: 3623:"Scientific opinion on the modification of the authorisation of a health claim related to cocoa flavanols and maintenance of normal endothelium-dependent vasodilation pursuant to Article 13(5) of Regulation (EC) No 1924/2006 following a request in accordance with Article 19 of Regulation (EC) No 1924/2006" 1099:
The most important food sources are commodities widely consumed in large quantities such as fruit and vegetables, green tea, black tea, red wine, coffee, chocolate, olives, and extra virgin olive oil. Herbs and spices, nuts and algae are also potentially significant for supplying certain polyphenols.
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from gastric, colorectal, breast and lung cancers. The study found that an increase in isoflavone consumption by 10 mg per day was associated with a 7% decrease in risk from all cancers, and an increase in consumption of soy protein by 5 grams per day produced a 12% reduction in breast cancer
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Numerous cross-sectional studies have examined the association between total dietary iron intake and dietary modulators of iron absorption on biochemical markers of iron status ... These studies suffer from a number of limitations... Findings from cross-sectional studies assessing the effects of
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Nachvak, Seyed Mostafa; Moradi, Shima; Anjom-Shoae, Javad; et al. (September 2019). "Soy, Soy Isoflavones, and Protein Intake in Relation to Mortality from All Causes, Cancers, and Cardiovascular Diseases: A Systematic Review and Dose-Response Meta-Analysis of Prospective Cohort Studies".
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or use of ethanol in an immersion extractor. The extraction conditions (temperature, extraction time, ratio of solvent to raw material, particle size of the sample, solvent type, and solvent concentrations) for different raw materials and extraction methods have to be optimized.
1292:, followed by various studies through the 21st century of a possible effect on cardiovascular diseases. For most polyphenols, there is no evidence for an effect on cardiovascular regulation, although there are some reviews showing a minor effect of consuming polyphenols, such as 1100:
Some polyphenols are specific to particular food (flavanones in citrus fruit, isoflavones in soya, phloridzin in apples); whereas others, such as quercetin, are found in all plant products such as fruit, vegetables, cereals, leguminous plants, tea, and wine.
3680:"Scientific opinion on the substantiation of health claims related to polyphenols in olive and protection of LDL particles from oxidative damage (ID 1333, 1638, 1639, 1696, 2865), maintenance of normal blood HDL cholesterol concentrations (ID 1639), mainte" 378:
moieties (most in ellagic acid-type components), and more than 40 phenolic hydroxyl groups, meets the criteria of both definitions of a polyphenol. Other examples of compounds that fall under both the WBSSH and Quideau definitions include the
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Aizpurua-Olaizola O, Ormazabal M, Vallejo A, Olivares M, Navarro P, Etxebarria N, Usobiaga A (January 2015). "Optimization of supercritical fluid consecutive extractions of fatty acids and polyphenols from Vitis vinifera grape wastes".
698:. Where fluorescence of the molecules themselves is insufficient for visualization by light microscopy, DPBA (diphenylboric acid 2-aminoethyl ester, also referred to as Naturstoff reagent A) has traditionally been used, at least in 484:
The C-glucoside substructure of polyphenols is exemplified by the phenol-saccharide conjugate puerarin, a midmolecular-weight plant natural product. The attachment of the phenol to the saccharide is by a carbon-carbon bond. The
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composed of 14 gallic acid units around a core of three units of glucose, with two gallic acids as simple esters, and the remaining 12 appearing in 6 ellagic acid-type units. Ester, ether, and biaryl linkages are present, see
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Roy MK, Koide M, Rao TP, Okubo T, Ogasawara Y, Juneja LR (March 2010). "ORAC and DPPH assay comparison to assess antioxidant capacity of tea infusions: relationship between total polyphenol and individual catechin content".
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from smaller polyphenols to non-hydrolyzable tannins and remain undiscovered in the plant matrix. Most polyphenols contain repeating phenolic moieties of pyrocatechol, resorcinol, pyrogallol, and phloroglucinol connected by
891:, found in virtually all families of plants. Larger polyphenols are often concentrated in leaf tissue, the epidermis, bark layers, flowers and fruits but also play important roles in the decomposition of forest litter, and 1499: 2491:
Meyer AS, Yi OS, Pearson DA, Waterhouse AL, Frankel EN (1997). "Inhibition of Human Low-Density Lipoprotein Oxidation in Relation to Composition of Phenolic Antioxidants in Grapes (Vitis vinifera)".
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in forest ecology. Absolute concentrations of total phenols in plant tissues differ widely depending on the literature source, type of polyphenols and assay; they are in the range of 1–25% total
756:. During this reaction, the blue ABTS radical cation is converted back to its colorless neutral form. The reaction may be monitored spectrophotometrically. This assay is often referred to as the 2171:
Arranz S, Saura-Calixto F, Shaha S, Kroon PA (August 2009). "High contents of nonextractable polyphenols in fruits suggest that polyphenol contents of plant foods have been underestimated".
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Owen RW, Haubner R, Hull WE, Erben G, Spiegelhalder B, Bartsch H, Haber B (December 2003). "Isolation and structure elucidation of the major individual polyphenols in carob fibre".
1817: 1258: 370:, a molecule at the core of naturally occurring phenolic compounds of varying sizes, is itself not a polyphenol by the WBSSH definition, but is by the Quideau definition. The 2088: 1216:
evidence exists to verify such a qualification and a Dietary Reference Intake value has been established – characteristics which have not been determined for polyphenols.
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polyphenol (EPP) content of a fruit which may also contain non-extractable polyphenols. Black tea contains high amounts of polyphenol and makes up for 20% of its weight.
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Alonso-Salces RM, Korta E, Barranco A, Berrueta LA, Gallo B, Vicente F (November 2001). "Pressurized liquid extraction for the determination of polyphenols in apple".
4186:"Effect of resveratrol supplementation on cognitive performance and mood in adults: a systematic literature review and meta-analysis of randomized controlled trials" 2446:
Pulido R, Bravo L, Saura-Calixto F (August 2000). "Antioxidant activity of dietary polyphenols as determined by a modified ferric reducing/antioxidant power assay".
448:, which allows for the possibility to rapidly diffuse across cell membranes so that they can reach intracellular sites of action or remain as pigments once the cell 7803: 2122: 1792:
MartĂ­n Santos MA, Bonilla Venceslada JL, MartĂ­n MartĂ­n A, GarcĂ­a GarcĂ­a I (2005). "Estimating the selectivity of ozone in the removal of polyphenols from vinasse".
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measurements. Some tests are relatively specific to polyphenols (for instance the Porter's assay). Total phenols (or antioxidant effect) can be measured using the
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Papoutsis, Konstantinos; Vuong, Quan; Golding, John; Hasperué, Joaquín; Pristijono, Penta; Bowyer, Michael; Scarlett, Christopher; Stathopoulos, Costas (2018).
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Flavonoids include flavones, flavonols, flavanols, flavanones, isoflavones, proanthocyanidins, and anthocyanins. Particularly abundant flavanoids in foods are
4381:"Interaction of dietary polyphenols and gut microbiota: Microbial metabolism of polyphenols, influence on the gut microbiota, and implications on host health" 8010: 5818: 2340:
Gani M, Mcguinness BJ, Da Vies AP (1998). "Monoclonal antibodies against tea polyphenols: A novel immunoassay to detect polyphenols in biological fluids".
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at doses exceeding 200 mg per day may contribute to maintenance of vascular elasticity and normal blood flow; 2) olive oil polyphenols (5 mg of
1477:, a class of polyphenol. The European Food Safety Authority established upper limits for some polyphenol-containing supplements and additives, such as 2652:
Pizzi A, Valenezuela J, Westermeyer C (1994). "Low formaldehyde emission, fast pressing, pine and pecan tannin adhesives for exterior particleboard".
4032:"Dietary intakes of flavan-3-ols and cardiometabolic health: systematic review and meta-analysis of randomized trials and prospective cohort studies" 3557: 9186: 6994: 4721: 1254:
are limited, with results difficult to interpret due to the wide variation of intake values for both individual polyphenols and total polyphenols.
2089:"Screening the effect of four ultrasound-assisted extraction parameters on hesperidin and phenolic acid content of aqueous citrus pomace extracts" 1082: 3395:
Hufnagel JC, Hofmann T (February 2008). "Orosensory-directed identification of astringent mouthfeel and bitter-tasting compounds in red wine".
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can also be made on C18 sorbent cartridges. Other techniques are ultrasonic extraction, heat reflux extraction, microwave-assisted extraction,
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Papoutsis, Konstantinos; Pristijono, Penta; Golding, John; Stathopoulos, Costas; Bowyer, Michael; Scarlett, Christopher; Vuong, Quan (2018).
1888: 3879:"Options for basing Dietary Reference Intakes (DRIs) on chronic disease endpoints: report from a joint US-/Canadian-sponsored working group" 1308:
Higher intakes of soy isoflavones may be associated with reduced risks of breast cancer in postmenopausal women and prostate cancer in men.
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Sineiro J, DomĂ­nguez H, NĂșñez MJ, Lema JM (1996). "Ethanol extraction of polyphenols in an immersion extractor. Effect of pulsing flow".
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Nakai S (2000). "Myriophyllum spicatum-released allelopathic polyphenols inhibiting growth of blue-green algae Microcystis aeruginosa".
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Wigglesworth VB (1988). "The source of lipids and polyphenols for the insect cuticle: The role of fat body, oenocytes and oenocytoids".
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Polyphenols are a large, diverse group of compounds, making it difficult to determine their biological effects. They are not considered
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Mello LD, Sotomayor MD, Kubota LT (2003). "HRP-based amperometric biosensor for the polyphenols determination in vegetables extract".
776: 1347:. A risk assessment by the European Food Safety Authority found no cause for concern when isoflavones are consumed in a normal diet. 4591: 4498: 2899: 1766: 780: 4332:"Dietary (poly)phenolics in human health: structures, bioavailability, and evidence of protective effects against chronic diseases" 3126:
Malek SR (1961). "Polyphenols and their quinone derivatives in the cuticle of the desert locust, Schistocerca gregaria (ForskÄl)".
1462: 1446:-containing drug. Polyphenols, particularly in beverages that contain them in high concentrations (tea, coffee, etc), inhibit the 1030:
or dimerization processes resulting in hydrolyzable tannins. For anthocyanidins, precursors of the condensed tannin biosynthesis,
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The White–Bate-Smith–Swain–Haslam (WBSSH) definition characterized structural characteristics common to plant phenolics used in
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Nawaz H, Shi J, Mittal GS, Kakuda Y (2006). "Extraction of polyphenols from grape seeds and concentration by ultrafiltration".
4136:"The effect of blueberry interventions on cognitive performance and mood: A systematic review of randomized controlled trials" 1038:(LAR) are crucial enzymes with subsequent addition of catechin and epicatechin moieties for larger, non-hydrolyzable tannins. 9369: 8580: 7789: 7772: 7177: 6388: 3583: 1494: 1076: 1027: 524: 3654: 3597: 2961:
Hart JH, Hillis WE (1974). "Inhibition of wood-rotting fungi by stilbenes and other polyphenols in Eucalyptus sideroxylon".
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Palma M, Taylor LT (July 1999). "Extraction of polyphenolic compounds from grape seeds with near critical carbon dioxide".
1823: 1778: 722:. The tannin content of the unknown is then expressed as equivalents of the appropriate hydrolyzable or condensed tannin. 571: 2243:"A method for visualizing fluorescence of flavonoid therapeutics in vivo in the model eukaryote Dictyostelium discoideum" 730: 567: 9179: 7922: 6987: 5223: 4714: 1377: 1262: 1205: 1035: 3928:"The effect of chlorogenic acid on blood pressure: a systematic review and meta-analysis of randomized clinical trials" 2367:
Walker RB, Everette JD (February 2009). "Comparative reaction rates of various antioxidants with ABTS radical cation".
182:, meaning "many, much") and the word ‘phenol’ which refers to a chemical structure formed by attachment of an aromatic 7996: 7868: 5804: 5773: 3091:
Krasnow MN, Murphy TM (June 2004). "Polyphenol glucosylating activity in cell suspensions of grape (Vitis vinifera)".
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Flavonoid pharmacokinetics: methods of analysis, pre-clinical and clinical pharmacokinetics, safety, and toxicology
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The term polyphenol is not well-defined, but it is generally agreed that they are natural products with "several
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HĂ€ttenschwiler S, Vitousek PM (June 2000). "The role of polyphenols in terrestrial ecosystem nutrient cycling".
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Polyphenols comprise up to 0.2–0.3% fresh weight for many fruits. Consuming common servings of wine, chocolate,
1063:. It is the rapid polymerisation of o-quinones to produce black, brown or red polyphenolic pigments that causes 8868: 8136: 7554: 7476: 6676: 5944: 4760: 1442:). In 1988, hemolytic anemia following polyphenol consumption was documented, resulting in the withdrawal of a 548: 7529: 3356:"Polyphenols: factors influencing their sensory properties and their effects on food and beverage preferences" 1151:
is not fully understood, but it is measured chemically as the ability of a substance to precipitate proteins.
523:, derived biosynthetically and sometimes synthetically by oxidative joining of two of the galloyl moieties of 4254:"Risk assessment for peri- and post-menopausal women taking food supplements containing isolated isoflavones" 9629: 9212: 9172: 8468: 7020: 6980: 6276: 4707: 1595: 1404: 788: 579: 3832:"Health and nutrition beyond essential nutrients: The evolution of the bioactives concept for human health" 2806:
Locke M, Krishnan N (1971). "The distribution of phenoloxidases and polyphenols during cuticle formation".
2275: 1485:. For most polyphenols found in the diet, an adverse effect beyond nutrient-drug interactions is unlikely. 1095:
or tea may also contribute to about one gram of intake per day. According to a 2005 review on polyphenols:
840:, high in tannins and other polyphenols, or its juice, is employed in the dyeing of non-synthetic fabrics. 9326: 9032: 8630: 8590: 8585: 7134: 6840: 6438: 6398: 6393: 5178: 2887: 1431: 1189: 844: 843:
Of some interest in the era of silver-based photography, pyrogallol and pyrocatechin are among the oldest
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Williams RJ, Spencer JP, Rice-Evans C (April 2004). "Flavonoids: antioxidants or signalling molecules?".
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Williams RJ, Spencer JP, Rice-Evans C (April 2004). "Flavonoids: antioxidants or signalling molecules?".
2759:"The occurrence and significance of phenolic hardening in the newly formed cuticle of Crustacea Decapoda" 1904:
Pan X (2003). "Microwave-assisted extraction of tea polyphenols and tea caffeine from green tea leaves".
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A 2019 systematic review found that intake of soy and soy isoflavones is associated with a lower risk of
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Cocoa flavanols help maintain the elasticity of blood vessels, which contributes to normal blood flow
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for particleboards. The aims are generally to make use of plant residues from grape, olive (called
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Haslam E, Cai Y (January 1994). "Plant polyphenols (vegetable tannins): gallic acid metabolism".
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when consumed together in a single meal. Research is limited on the effect of this inhibition on
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Polyphenols are thought to play diverse roles in the ecology of plants. These functions include:
919: 659: 3598:"Article 13 (5): Cocoa flavanols; Search filters: Claim status – authorised; search – flavanols" 4423:
Davies NM, Yåñez JA (2013). "Flavonoids and drug interactions". In Davies NM, Yanez JA (eds.).
2888:"Role of phenolics in the resistance mechanisms of plants against fungal pathogens and insects" 1618: 1243:) may "contribute to the protection of blood lipids from oxidative damage", if consumed daily. 314:
In terms of structures, the WBSSH recognizes two structural family that have these properties:
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Mainly found in the fruit skins and seeds, high levels of polyphenols may reflect only the
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Committee on Toxicity of Chemicals in Food, Consumer Products and the Environment (2003).
3560:. Center for Food Safety and Applied Nutrition, US Food and Drug Administration. July 2008 3342: 2988:
Popa VI, Dumitru M, Volf I, Anghel N (2008). "Lignin and polyphenols as allelochemicals".
1447: 1135:. Polyphenols in wine, beer and various nonalcoholic juice beverages can be removed using 1003: 856: 826: 598: 509: 357: 352:
According to Stéphane Quideau, the term "polyphenol" refers to compounds derived from the
225:" including four principal classes: "phenolic acids, flavonoids, stilbenes, and lignans". 218: 41: 8938: 6746: 4546: 364:
pathway, featuring more than one phenolic unit and deprived of nitrogen-based functions.
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Representative chemical structure of one of many plant-derived polyphenols that comprise
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Del Rio D, Rodriguez-Mateos A, Spencer JP, Tognolini M, Borges G, Crozier A (May 2013).
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Olive oil polyphenols contribute to the protection of blood lipids from oxidative stress
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and are investigated as a potential metabolic factor in function of the gut microbiota.
760:(TEAC) assay. The reactivity of the various antioxidants tested are compared to that of 9542: 9529: 9467: 9237: 9109: 9093: 9037: 8610: 8480: 8436: 7714: 7697: 7659: 7461: 7436: 7350: 7337: 7275: 7045: 6917: 6901: 6845: 6418: 6288: 6244: 5750: 5704: 5617: 5612: 5602: 5579: 5541: 5531: 5112: 4637: 4612: 4356: 4331: 4056: 4031: 4007: 3982: 3903: 3878: 3513: 3458: 3431: 3230: 3203: 3179: 3154: 1504: 1474: 1439: 1427: 1416: 1312: 1266: 1247: 1232: 1220: 1172:. In contrast, hydroxycinnamic acids do not have astringent qualities, but are bitter. 1155: 1064: 999: 915: 896: 892: 860: 806: 719: 618: 536: 498: 336: 4458:
Jaeger A, WĂ€lti M, Neftel K (1988). "Side effects of flavonoids in medical practice".
3036: 2819: 2700: 2614:(2nd ed.). Oxford University Press. pp. 38, 79, 81, 89, 90–91, 176–177, etc. 2030: 1995: 1925: 1850: 9618: 9485: 9452: 9437: 9432: 9374: 9349: 9344: 9339: 9301: 9203: 9195: 9160: 9060: 9016: 8988: 8705: 8642: 8365: 8317: 7679: 7674: 7669: 7654: 7616: 7591: 7495: 7451: 7427: 7293: 7260: 7245: 7240: 7182: 7157: 7152: 7147: 7109: 7011: 7003: 6968: 6868: 6824: 6796: 6513: 6450: 6173: 6125: 5695: 5661: 5656: 5607: 4837: 4731: 4406: 4253: 4170: 4120: 3981:
Ried K, Fakler P, Stocks NP, et al. (Cochrane Hypertension Group) (April 2017).
3863: 3139: 2735: 1344: 1201: 1015: 1007: 950: 718:, is used to oxidize known concentrations of a standard tannin solution, producing a 687: 645: 445: 441: 298: 270: 222: 167: 116: 4660:
EFSA Panel on Food Additives and Nutrient Sources Added to Food (1 September 2010).
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total iron intake, ascorbic acid, calcium and polyphenols, have been inconsistent...
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intended for treating venous disorders. Their mechanism of action is undefined, and
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Tanner GJ, Francki KT, Abrahams S, Watson JM, Larkin PJ, Ashton AR (August 2003).
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for which development of dietary recommendations was under consideration in 2017.
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Some methods for quantification of total polyphenol content in vitro are based on
3335: 2554: 2227: 1184:, as they are not used for growth, survival or reproduction, nor do they provide 740:
Other tests measure the antioxidant capacity of a fraction. Some make use of the
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Metabolism of polyphenols can result in flavonoid-drug interactions, such as in
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is an histological dye specific to polyphenols used in microscopy analyses. The
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and analogs. Flavonoids and caffeic acid derivatives are biosynthesized from
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Other antioxidant capacity assays which use Trolox as a standard include the
9568: 9505: 9495: 8983: 8835: 8830: 8825: 8648: 8558: 8518: 8416: 8380: 8237: 8210: 8202: 8161: 8153: 8115: 8056: 7914: 7376: 7313: 7303: 6791: 6643: 6638: 6633: 6456: 6366: 6326: 6224: 6188: 6045: 6018: 6010: 5969: 5961: 5923: 5864: 5293: 5202: 5155: 5086: 4926: 4781: 4739: 4202: 4185: 3927: 3894: 3448: 2914:"Influence of polyphenols on bacterial biofilm formation and quorum-sensing" 2638: 1960: 1704: 1687: 1637: 1369: 1325: 1281: 1251: 1060: 949:
UV screens to protect against ionizing radiation and to provide coloration (
903: 795: 765: 753: 422: 380: 353: 254: 183: 120: 115:. They are abundant in plants and structurally diverse. Polyphenols include 4646: 4365: 4221: 4162: 4112: 4065: 4016: 3959: 3912: 3877:
Yetley EA, MacFarlane AJ, Greene-Finestone LS, et al. (January 2017).
3855: 3816: 3781: 3746: 3467: 3416: 3381: 3321: 3294:
Miglio C, Chiavaro E, Visconti A, Fogliano V, Pellegrini N (January 2008).
3280: 3239: 3188: 3112: 3077: 3068: 3051: 2939: 2827: 2792: 2783: 2758: 2743: 2708: 2477: 2424: 2388: 2318: 2268: 2200: 2038: 2003: 1968: 1858: 1748: 1713: 1564: 1555: 1538: 694:
of polyphenols can also be used, especially for localisation of lignin and
4699: 4471: 4424: 4347: 4047: 3170: 2259: 2242: 2123:"Pretreatment of citrus by-products affects polyphenol recovery: a review" 206: 9573: 9500: 9457: 9395: 9334: 9127: 8978: 8910: 8815: 8731: 8527: 8453: 8342: 8333: 8313: 8304: 8233: 8187: 8051: 7899: 7858: 7843: 7830: 7729: 7566: 7549: 7441: 7381: 7308: 7265: 7203: 7142: 6935: 6786: 6718: 6623: 6539: 6335: 6261: 6150: 6141: 6121: 6112: 6041: 5995: 5859: 5637: 5622: 5594: 5523: 5489: 5288: 5160: 5061: 5035: 5020: 4971: 4961: 4921: 4846: 4785: 4282: 3713:"Design of polyphenol-rich diets in clinical trials: A systematic review" 3432:"The Role of Polyphenols in Human Health and Food Systems: A Mini-Review" 3220: 2974: 2625:
Hillis WE, Urbach G (1959). "Reaction of polyphenols with formaldehyde".
2289:
Tempel AS (October 1982). "Tannin-measuring techniques : A review".
1779:"Cardiovascular disease and phytochemicals. Anonymous. C. Hamilton et al" 1740: 1482: 1443: 1208:
issued guidance to manufacturers that polyphenols cannot be mentioned on
1181: 1169: 1128: 1117: 927: 868: 734: 470: 429: 242: 238: 230: 191: 150: 146: 7781: 4212: 3943: 3737: 2468: 922:. In crustaceans, there is a second oxidase activity leading to cuticle 566:, methanol, methanol/formic acid, methanol/water/acetic or formic acid. 293:
In terms of properties, the WBSSH describes the polyphenols as follows:
32: 9537: 8958: 8943: 8495: 8191: 8179: 7848: 7838: 7736: 7707: 7579: 7534: 7500: 7483: 7345: 6766: 6751: 6303: 5999: 5987: 5515: 5505: 5426: 5247: 5242: 5170: 5165: 5107: 5102: 5056: 5030: 4966: 4905: 4900: 4826: 4817: 4777: 3202:
D'Archivio M, Filesi C, VarĂŹ R, Scazzocchio B, Masella R (March 2010).
3155:"Plant polyphenols as dietary antioxidants in human health and disease" 2665: 2310: 2192: 2149: 2065: 1407:
of benefit for using phlebotonics to treat venous diseases is limited.
1392: 1365: 1356: 1240: 1193: 1136: 998:
Polyphenols incorporate smaller parts and building blocks from simpler
899:
and polyphenols, calculated with reference to the dry green leaf mass.
695: 583: 449: 246: 112: 3430:
Cory H, Passarelli S, Szeto J, Tamez M, Mattei J (21 September 2018).
3408: 3312: 3295: 3253:
Mennen LI, Walker R, Bennetau-Pelissero C, Scalbert A (January 2005).
3104: 2504: 2459: 2380: 2184: 1813: 1154:
Astringency increases and bitterness decrease with the mean degree of
617:
Reversed-phase HPLC plot of separation of phenolic compounds. Smaller
9597: 9515: 8775: 8739: 8656: 8535: 8274: 8241: 8046: 7904: 7753: 7748: 7741: 7724: 7702: 7539: 7519: 7405: 7323: 6583: 6547: 6464: 6343: 6082: 6049: 5854: 5676: 5218: 5076: 5010: 4976: 4947: 4860: 2843:"Phenolic Tanning and Pigmentation of the Cuticle in Carcinus maenas" 1470: 1466: 1166: 1163: 1132: 1092: 986:(a submerged aquatic plant) secrete polyphenols that are involved in 872: 761: 745: 699: 622: 458: 344: 266: 187: 177: 4397: 4380: 1537:
Quideau S, Deffieux D, Douat-Casassus C, Pouységu L (January 2011).
1261:, but this concept is obsolete. Most polyphenols are metabolized by 480: 198:
suffix). The term "polyphenol" has been in use at least since 1894.
142: 4695:
Phenol-Explorer, electronic database of polyphenol content in foods
3538:. National Agricultural Library, US Department of Agriculture. 2022 613: 8928: 6736: 3926:
Onakpoya, I J; Spencer, E A; Thompson, M J; Heneghan, C J (2014).
943: 876: 749: 612: 514: 505: 502: 479: 410: 397: 335: 205: 141: 4694: 748:
which is reactive towards most antioxidants including phenolics,
461:(hydrolyzable tannins) or more stable C-C bonds (nonhydrolyzable 4559:(RR-3). Centers for Disease Control and Prevention. 3 April 1998 1686:
Manach C, Scalbert A, Morand C, Rémésy C, Jiménez L (May 2004).
1500:
Dictionary of natural phenols and polyphenols molecular formulas
1451: 1361:
Phlebotonics of heterogeneous composition, consisting partly of
977: 741: 274: 9168: 8747: 8125: 8079: 7992: 7785: 6976: 6555: 5933: 5887: 5800: 4749: 4703: 409:
core. There are nine phenolic hydroxyl groups and two phenolic
4134:
Travica N, D'Cunha NM, Naumovski N, et al. (March 2020).
3204:"Bioavailability of the polyphenols: status and controversies" 822: 132: 82: 171: 7773:
List of phytochemicals and foods in which they are prominent
4493:. The Stationery Office. 2010. pp. 65, 68, 70, 73, 74. 918:). The hardening of the cuticle is due to the presence of a 562:
of polyphenols can be performed using a solvent like water,
405:, a plant-derived polyphenol, an ester of gallic acid and a 4030:
Raman G, Avendano EE, Chen S, et al. (November 2019).
966:
Signaling molecules in ripening and other growth processes.
519:
An example of a synthetically achieved small ellagitannin,
88: 73: 1112:– especially iron and other metal ions, which may bind to 805:–coupled HPLC are generally given as relative rather than 652:. They can also be analysed by chemical characterisation. 100: 67: 4613:"Scientific opinion on the safety of green tea catechins" 4611:
Younes M, Aggett P, Aguilar F, et al. (April 2018).
926:. There is apparently no polyphenol tanning occurring in 3492:(12). European Food Safety Authority. 4 September 2019. 3482:"Dietary Reference Values for nutrients: Summary report" 1324:
Polyphenols are under preliminary research for possible
4184:
Marx W, Kelly JT, Marshall S, et al. (June 2018).
1227:
were authorized between 2012 and 2015: 1) flavanols in
674:. Purified compounds can be identified by the means of 2866:"The Epicuticle of an Arachnid, Palamneus swammerdami" 4379:
Catalkaya G, Venema K, Lucini L, et al. (2020).
798:
can help monitor the content of polyphenols in food.
327:
and hexahydroxydiphenoyl esters and their derivatives
97: 85: 79: 61: 5745:
Terpene synthase enzymes (many), having in common a
2405:
International Journal of Food Sciences and Nutrition
1067:. In insects, PPO is involved in cuticle hardening. 452:. Hence, many larger polyphenols are biosynthesized 103: 91: 70: 64: 9587: 9561: 9528: 9476: 9413: 9388: 9325: 9266: 9246: 9220: 9211: 9202: 9159: 9140: 9080: 9025: 9000: 8919: 8881: 8854: 8791: 8782: 8738: 8724: 8689: 8655: 8641: 8571: 8549: 8526: 8517: 8494: 8467: 8444: 8435: 8407: 8379: 8356: 8327: 8298: 8282: 8273: 8251: 8224: 8201: 8178: 8169: 8160: 8114: 8070: 8027: 7974: 7946: 7913: 7885: 7867: 7829: 7819: 7764: 7688: 7625: 7607: 7565: 7426: 7395: 7369: 7336: 7284: 7221: 7196: 7133: 7074: 7054: 7028: 7019: 7010: 6967: 6948: 6888: 6833: 6808: 6727: 6689: 6662: 6599: 6590: 6546: 6532: 6497: 6463: 6449: 6379: 6357: 6334: 6325: 6302: 6275: 6252: 6243: 6215: 6187: 6164: 6135: 6106: 6090: 6081: 6059: 6032: 6009: 5986: 5977: 5968: 5922: 5878: 5835: 5789: 5760: 5738: 5721: 5694: 5646: 5593: 5578: 5561: 5498: 5425: 5415: 5398: 5337: 5311: 5281: 5256: 5235: 5211: 5201: 5140: 5095: 5044: 4998: 4989: 4940: 4914: 4893: 4874: 4836: 4793: 4738: 1055:(PPO) is an enzyme that catalyses the oxidation of 942:Release and suppression of growth hormones such as 710:Polyphenolic content in vitro can be quantified by 444:). Their upper molecular weight limit is about 800 440:
Polyphenols, such as lignin, are larger molecules (
76: 1250:that assessed the effect of polyphenols on health 1108:– compounds that interfere with the absorption of 4256:. European Food Safety Authority. 21 October 2015 4085:Journal of the Academy of Nutrition and Dietetics 3711:Condezo-Hoyos L, Gazi C, PĂ©rez-JimĂ©nez J (2021). 3600:. European Commission, EU Register. 31 March 2015 1147:With respect to food and beverages, the cause of 1123:In a comparison of cooking methods, phenolic and 1794:Journal of Chemical Technology and Biotechnology 1619:"Isolation and structure elucidation of tannins" 783:(FRAP) assays or inhibition of copper-catalyzed 497:Polyphenols often have functional groups beyond 40:. Such compound are formed by esterification of 3657:. European Commission, EU Register. 16 May 2012 1688:"Polyphenols: food sources and bioavailability" 1415:Polyphenols are extensively metabolized by the 855:Natural polyphenols have long been proposed as 636:is used as a reagent for staining phenolics in 131:, some of which have been used historically as 4823:Iridoid glycosides (iridoids bound to a sugar) 4311:. National Institutes of Health. 26 April 2012 2912:Huber B, Eberl L, Feucht W, Polster J (2003). 2556:Recent trends in horticulture in the Himalayas 956:Deterrence of herbivores (sensory properties). 9180: 8759: 8137: 8091: 8004: 7797: 6988: 6567: 5945: 5899: 5812: 4761: 4715: 2054:Journal of the American Oil Chemists' Society 1883:. Royal Society of Chemistry. pp. 1–16. 1872:Escribano-Bailon MT, Santos-Buelga C (2003). 1761:Practical Polyphenolics, Edwin Haslam, 1998, 1376:) and synthetic compounds, are used to treat 1127:levels in vegetables were retained better by 809:as there is a lack of commercially available 801:Quantitation results produced by the mean of 8: 4460:Progress in Clinical and Biological Research 3255:"Risks and safety of polyphenol consumption" 2763:Proceedings of the Royal Society of Medicine 1430:of polyphenol intake range from mild (e.g., 859:precursors to produce plastics or resins by 111:) are a large family of naturally occurring 4586:. The Stationery Office. 2010. p. 74. 3987:The Cochrane Database of Systematic Reviews 3516:. UK National Health Service. 3 August 2020 3208:International Journal of Molecular Sciences 1879:. In Santos-Buelga C, Williamson G (eds.). 1022:. Complex gallotannins develop through the 821:Some polyphenols are traditionally used as 644:, especially in the ultraviolet domain, by 9217: 9208: 9187: 9173: 9165: 8788: 8766: 8752: 8744: 8523: 8441: 8279: 8175: 8166: 8144: 8130: 8122: 8098: 8084: 8076: 8011: 7997: 7989: 7804: 7790: 7782: 7025: 7016: 6995: 6981: 6973: 6596: 6574: 6560: 6552: 6331: 6249: 6087: 5983: 5974: 5952: 5938: 5930: 5906: 5892: 5884: 5819: 5805: 5797: 5590: 5422: 5208: 4995: 4890: 4768: 4754: 4746: 4722: 4708: 4700: 4036:The American Journal of Clinical Nutrition 3883:The American Journal of Clinical Nutrition 3397:Journal of Agricultural and Food Chemistry 3360:The American Journal of Clinical Nutrition 3300:Journal of Agricultural and Food Chemistry 3259:The American Journal of Clinical Nutrition 3093:Journal of Agricultural and Food Chemistry 2870:Quarterly Journal of Microscopical Science 2847:Quarterly Journal of Microscopical Science 2493:Journal of Agricultural and Food Chemistry 2448:Journal of Agricultural and Food Chemistry 2369:Journal of Agricultural and Food Chemistry 2173:Journal of Agricultural and Food Chemistry 1692:The American Journal of Clinical Nutrition 1188:. Therefore, they do not have recommended 902:Polyphenols are also found in animals. In 386:shown below, and the hydrolyzable tannin, 4636: 4418: 4416: 4396: 4355: 4211: 4201: 4055: 4006: 3902: 3736: 3695: 3638: 3497: 3457: 3447: 3371: 3311: 3270: 3229: 3219: 3178: 3159:Oxidative Medicine and Cellular Longevity 3067: 2929: 2782: 2467: 2258: 2241:Ferrara BT, Thompson EP (February 2019). 1703: 1554: 1532: 1530: 1465:, which involves inhibition of the liver 18:Health effects of phenols and polyphenols 4277: 4275: 4273: 4271: 3577: 3575: 1681: 1679: 1677: 1269:. Some polyphenols are considered to be 969:In some woods can explain their natural 31: 4077: 4075: 3354:Lesschaeve I, Noble AC (January 2005). 3128:Comparative Biochemistry and Physiology 1526: 1162:is more bitter and astringent than its 1083:Natural phenols and polyphenols in wine 2216:Separation and Purification Technology 1087:Natural phenols and polyphenols in tea 1006:pathway for the phenolic acids or the 887:The most abundant polyphenols are the 758:Trolox equivalent antioxidant capacity 702:, to enhance the fluorescence signal. 664:high performance liquid chromatography 1941: 1939: 1937: 1935: 1590: 1588: 1586: 1584: 1582: 1580: 1578: 1576: 1574: 535:The analysis techniques are those of 7: 1339:, which are structurally related to 1257:Polyphenols were once considered as 1116:and other proteins, particularly in 1041:The glycosylated form develops from 959:Prevention of microbial infections ( 668:reversed-phase liquid chromatography 307:with >12 phenolic hydroxyl groups 304:with molecular weight of 500–4000 Da 3983:"Effect of cocoa on blood pressure" 3809:10.1016/j.freeradbiomed.2004.01.001 3797:Free Radical Biology & Medicine 3774:10.1016/j.freeradbiomed.2004.01.001 3762:Free Radical Biology & Medicine 3056:The Journal of Biological Chemistry 1906:Chemical Engineering and Processing 851:Aspirational use as green chemicals 310:with 5–7 aromatic rings per 1000 Da 48:to a monosaccharide (glucose) core. 5747:terpene synthase N terminal domain 4336:Antioxidants & Redox Signaling 1874:"Polyphenol Extraction From Foods" 777:oxygen radical absorbance capacity 601:. Purification can be achieved by 25: 4527:. World Health Organization. 2001 2689:Trends in Ecology & Evolution 2608:Gernsheim H, Gernsheim A (1969). 2520:Sensors and Actuators B: Chemical 1288:) were considered as a factor in 794:New methods including the use of 781:ferric reducing ability of plasma 374:, on the other hand, with its 14 2918:Zeitschrift fĂŒr Naturforschung C 2342:Food and Agricultural Immunology 2274: 1212:as antioxidant nutrients unless 1104:Some polyphenols are considered 813:for all polyphenolic molecules. 640:. Polyphenols can be studied by 157:), is a well-studied polyphenol. 57: 9254:p-Hydroxybenzoic acid glucoside 7062:p-Hydroxybenzoic acid glucoside 4305:"Vasculera – diosmiplex tablet" 2894:: Advances in Research, 23–67. 1395:, while one other – Vasculera ( 149:, a bright yellow component of 9423:α-Cyano-4-hydroxycinnamic acid 9370:Phloroglucinol carboxylic acid 8581:List of phytochemicals in food 7231:α-Cyano-4-hydroxycinnamic acid 7178:Phloroglucinol carboxylic acid 6389:List of phytochemicals in food 4429:. Hoboken, New Jersey: Wiley. 3999:10.1002/14651858.CD008893.pub3 1881:Methods in Polyphenol Analysis 1495:List of phytochemicals in food 1077:List of phytochemicals in food 879:shells left after processing. 621:formed individual peaks while 525:1,2,3,4,6-pentagalloyl-glucose 469:are mostly polymeric units of 1: 4143:Brain, Behavior, and Immunity 3932:Journal of Human Hypertension 3836:Molecular Aspects of Medicine 3729:10.1016/j.foodres.2021.110655 3037:10.1016/S0043-1354(00)00039-7 3002:10.1016/j.indcrop.2007.07.019 2990:Industrial Crops and Products 2864:Krishnan G (September 1954). 2841:Krishnan G (September 1951). 2820:10.1016/S0040-8166(71)80034-4 2701:10.1016/S0169-5347(00)01861-9 2553:Jindal KK, Sharma RC (2004). 2142:10.1080/87559129.2018.1438471 2031:10.1016/S0021-9673(01)01212-2 1996:10.1016/S0021-9673(99)00569-5 1926:10.1016/S0255-2701(02)00037-5 1851:10.1016/S0278-6915(03)00200-X 1028:1,2,3,4,6-pentagalloylglucose 597:Concentration can be made by 572:countercurrent chromatography 425:, hence their description as 269:are polyphenols derived from 5224:Geranylgeranyl pyrophosphate 3582:Gross, Paul (1 March 2009). 3486:EFSA Supporting Publications 3153:Pandey KB, Rizvi SI (2009). 3140:10.1016/0010-406X(61)90071-8 2886:V. Lattanzio et al. (2006). 2757:Dennell R (September 1947). 2736:10.1016/0040-8166(88)90033-X 2627:Journal of Applied Chemistry 2585:The Film Developing Cookbook 2583:Anchell SG, Troop B (1998). 2228:10.1016/j.seppur.2005.07.006 1839:Food and Chemical Toxicology 1662:. Merriam-Webster, Inc. 2019 1463:grapefruit–drug interactions 1423:Toxicity and adverse effects 1378:chronic venous insufficiency 1263:catechol-O-methyltransferase 1206:Food and Drug Administration 1204:. In the United States, the 1036:leucoanthocyanidin reductase 508:linkages are common, as are 178: 8906:Pyrocatecollic type tannins 6714:Pyrocatecollic type tannins 5774:Dimethylallyl pyrophosphate 4580:SACN Iron and Health Report 4487:SACN Iron and Health Report 4285:. Drugs.com. 1 January 2019 4237:"Phytoestrogens and Health" 3717:Food Research International 3499:10.2903/sp.efsa.2017.e15121 2654:Holz Als Roh- und Werkstoff 2291:Journal of Chemical Ecology 2019:Journal of Chromatography A 1984:Journal of Chromatography A 1434:symptoms) to severe (e.g., 1357:Diosmin § Phlebotonics 1284:, polyphenols (then called 1045:activity and increases the 1002:, which originate from the 994:Biosynthesis and metabolism 910:polyphenols play a role in 253:(apple, grape, cocoa), and 27:Class of chemical compounds 9646: 7923:Geranylgeranyl diphosphate 4097:10.1016/j.jand.2019.04.011 2890:(and references therein). 2611:The History of PHOTOGRAPHY 2130:Food Reviews International 2108:10.1016/j.fbio.2017.11.001 1354: 1235:and its derivatives (e.g. 1080: 1074: 676:nuclear magnetic resonance 670:(RPLC), can be coupled to 666:(HPLC), and especially by 603:preparative chromatography 241:(red fruits and berries), 172: 166:The name derives from the 9292:3,5-Dihydroxybenzoic acid 9287:2,6-Dihydroxybenzoic acid 9282:2,4-Dihydroxybenzoic acid 9276:2,3-Dihydroxybenzoic acid 8628: 7100:3,5-Dihydroxybenzoic acid 7095:2,6-Dihydroxybenzoic acid 7090:2,4-Dihydroxybenzoic acid 7084:2,3-Dihydroxybenzoic acid 6436: 5768:Isopentenyl pyrophosphate 5722:Norisoprenoids (modified) 4155:10.1016/j.bbi.2019.04.001 3848:10.1016/j.mam.2022.101116 3341:27 September 2013 at the 3336:Basic Tastes: Astringency 2540:10.1016/j.snb.2003.07.008 2417:10.3109/09637480903292601 2354:10.1080/09540109809354964 1032:dihydroflavonol reductase 638:thin layer chromatography 570:can be also performed or 9213:Monohydroxybenzoic acids 8869:1,3,6-Trigalloyl glucose 7555:Syn-propanethial-S-oxide 7477:Phenethyl Isothiocyanate 7021:Monohydroxybenzoic acids 6677:1,3,6-Trigalloyl glucose 5761:Activated isoprene forms 5562:Sesquarterpenes/oids (7) 4811:Monocyclic (single ring) 4678:10.2903/j.efsa.2010.1679 4629:10.2903/j.efsa.2018.5239 3830:Erdman, John W. (2022). 3697:10.2903/j.efsa.2011.2033 3640:10.2903/j.efsa.2014.3654 3334:Staff, Sensory Society. 2931:10.1515/znc-2003-11-1224 731:Folin–Ciocalteu reaction 568:Liquid–liquid extraction 9327:Trihydroxybenzoic acids 8591:O-methylated flavonoids 8586:C-methylated flavonoids 7634:Saturated cyclic acids 7135:Trihydroxybenzoic acids 6399:O-methylated flavonoids 6394:C-methylated flavonoids 5384:Secodehydroabietic acid 3895:10.3945/ajcn.116.139097 3690:(4): 2033. April 2011. 3586:. Nutraceuticals World. 3536:"Vitamins and minerals" 3514:"Vitamins and minerals" 3449:10.3389/fnut.2018.00087 2639:10.1002/jctb.5010091207 1961:10.1111/1750-3841.12715 1949:Journal of Food Science 1729:Natural Product Reports 1638:10.1351/pac198961030357 1473:, likely by grapefruit 1277:Cardiovascular diseases 906:, such as insects, and 845:photographic developers 829:. For instance, in the 789:low-density lipoprotein 580:critical carbon dioxide 277:seed and other cereals. 260:Phenolic acids include 194:(-OH) group (hence the 9268:Dihydroxybenzoic acids 8631:Flavonoid biosynthesis 8469:3-hydroxyanthocyanidin 7076:Dihydroxybenzoic acids 6439:Flavonoid biosynthesis 6277:3-hydroxyanthocyanidin 5179:Farnesyl pyrophosphate 3436:Frontiers in Nutrition 3373:10.1093/ajcn/81.1.330S 3366:(1 Suppl): 330S–335S. 3272:10.1093/ajcn/81.1.326S 3265:(1 Suppl): 326S–329S. 3069:10.1074/jbc.M302783200 2784:10.1098/rspb.1947.0027 1556:10.1002/anie.201000044 1432:gastrointestinal tract 1399:) – is a prescription 1290:capillary permeability 1102: 773:diphenylpicrylhydrazyl 714:. An oxidizing agent, 656:Instrumental chemistry 630: 576:Solid phase extraction 545:structural elucidation 527: 494: 414: 372:raspberry ellagitannin 349: 341:Raspberry ellagitannin 214: 158: 49: 9415:Hydroxycinnamic acids 9297:Ethyl protocatechuate 9233:4-Hydroxybenzoic acid 9228:3-Hydroxybenzoic acid 9002:Flavono-ellagitannins 8993:Phlorofucofuroeckol B 8969:Phlorofucofuroeckol A 8901:Catechol-type tannins 8896:Polyflavonoid tannins 8446:3-deoxyanthocyanidins 7813:Secondary metabolites 7530:3,3'-Diindolylmethane 7458:Aglycone derivatives 7223:Hydroxycinnamic acids 7105:Ethyl protocatechuate 7041:4-Hydroxybenzoic acid 7036:3-Hydroxybenzoic acid 6810:Flavono-ellagitannins 6801:Phlorofucofuroeckol B 6777:Phlorofucofuroeckol A 6709:Catechol-type tannins 6704:Polyflavonoid tannins 6254:3-deoxyanthocyanidins 5381:Sandaracopimaric acid 5026:Geranyl pyrophosphate 4348:10.1089/ars.2012.4581 4203:10.1093/nutrit/nuy010 3171:10.4161/oxim.2.5.9498 2260:10.2144/btn-2018-0084 1705:10.1093/ajcn/79.5.727 1515:Secondary metabolites 1510:Polyphenolic proteins 1300:, on blood pressure. 1097: 983:Myriophyllum spicatum 616: 518: 483: 401: 339: 297:generally moderately 290:(i.e., the tannins). 257:(onion, tea, apples). 209: 145: 35: 9478:Aromatic amino acids 9389:Other phenolic acids 8784:Hydrolysable tannins 8676:Secoisolariciresinol 7545:Allyl isothiocyanate 7472:Allyl isothiocyanate 7286:Aromatic amino acids 7197:Other phenolic acids 6592:Hydrolysable tannins 6484:Secoisolariciresinol 5571:Tetraprenylcurcumene 5052:Grapefruit mercaptan 4309:dailymed.nlm.nih.gov 4091:(9): 1483–1500.e17. 3221:10.3390/ijms11041321 2975:10.1094/Phyto-64-939 2559:. Indus Publishing. 1741:10.1039/NP9941100041 1343:, are classified as 803:diode array detector 712:volumetric titration 650:paper chromatography 634:Phosphomolybdic acid 592:measured extractable 531:Analytical chemistry 436:Structural chemistry 403:Theaflavin-3-gallate 384:theaflavin-3-gallate 9511:5-hydroxytryptophan 9317:Protocatechuic acid 9026:Other Miscellaneous 8029:Natural monophenols 7895:Geranyl diphosphate 7319:5-hydroxytryptophan 7125:Protocatechuic acid 6834:Other Miscellaneous 5837:Natural monophenols 5354:Dehydroabietic acid 4820:(cyclopentane ring) 4048:10.1093/ajcn/nqz178 3944:10.1038/jhh.2014.46 3062:(34): 31647–31656. 3029:2000WatRe..34.3026N 2775:1947RSPSB.134..485D 2532:2003SeAcB..96..636M 2303:1982JCEco...8.1289T 1918:2003CEPPI..42..129P 1806:2005JCTB...80..433M 1389:dietary supplements 1328:in healthy adults. 1271:bioactive compounds 1267:signaling molecules 1190:daily intake levels 1110:essential nutrients 1043:glucosyltransferase 831:Indian subcontinent 682:Microscopy analysis 609:Analysis techniques 321:and its derivatives 9598:Phenolic compounds 8841:Tellimagrandin IIs 8021:phenolic compounds 7406:Phenolic compounds 6649:Tellimagrandin IIs 5829:phenolic compounds 5791:Phenolic compounds 4814:Bicyclic (2 rings) 2924:(11–12): 879–884. 2666:10.1007/BF02621421 2311:10.1007/BF00987762 2066:10.1007/BF02523372 1320:Cognitive function 1071:Occurrence in food 1053:Polyphenol oxidase 920:polyphenol oxidase 631: 528: 495: 415: 350: 332:Quideau definition 215: 159: 50: 9612: 9611: 9524: 9523: 9409: 9408: 9307:Homogentisic acid 9278:(Hypogallic acid) 9262: 9261: 9155: 9154: 9076: 9075: 9043:Synthetic tannins 9005:(complex tannins) 8891:Proanthocyanidins 8883:Condensed tannins 8877: 8876: 8864:Digalloyl glucose 8774:Types of natural 8637: 8636: 8624: 8623: 8567: 8566: 8540:Isoliquiritigenin 8490: 8489: 8431: 8430: 8269: 8268: 7986: 7985: 7976:←Enzyme cofactors 7779: 7778: 7525:Indole-3-carbinol 7511:Diallyl disulfide 7420: 7419: 7332: 7331: 7217: 7216: 7115:Homogentisic acid 7086:(Hypogallic acid) 7070: 7069: 6963: 6962: 6884: 6883: 6851:Synthetic tannins 6813:(complex tannins) 6699:Proanthocyanidins 6691:Condensed tannins 6685: 6684: 6672:Digalloyl glucose 6582:Types of natural 6445: 6444: 6432: 6431: 6375: 6374: 6348:Isoliquiritigenin 6298: 6297: 6239: 6238: 6077: 6076: 5783: 5782: 5731:7,8-dihydroionone 5690: 5689: 5557: 5556: 5394: 5393: 5362:Lambertianic acid 5136: 5135: 4985: 4984: 4800:Acyclic (linear, 4436:978-1-118-35440-7 4342:(14): 1818–1892. 4190:Nutrition Reviews 3409:10.1021/jf073031n 3313:10.1021/jf072304b 3105:10.1021/jf035234r 3099:(11): 3467–3472. 3023:(11): 3026–3032. 2808:Tissue & Cell 2724:Tissue & Cell 2566:978-81-7387-162-7 2505:10.1021/jf960721a 2460:10.1021/jf9913458 2381:10.1021/jf8026765 2297:(10): 1289–1298. 2185:10.1021/jf9016652 2179:(16): 7298–7303. 1890:978-0-85404-580-8 1845:(12): 1727–1738. 1814:10.1002/jctb.1222 1617:Nonaka G (1989). 1543:Angewandte Chemie 1479:green tea extract 1405:clinical evidence 1326:cognitive effects 1114:digestive enzymes 889:condensed tannins 672:mass spectrometry 658:analyses include 584:liquid extraction 521:tellimagrandin II 467:Proanthocyanidins 463:condensed tannins 319:proanthocyanidins 251:proanthocyanidins 237:(citrus fruits), 16:(Redirected from 9637: 9579:Alkylresorcinols 9443:Chlorogenic acid 9218: 9209: 9189: 9182: 9175: 9166: 9116:Phenylpropanoids 9088:Diarylheptanoids 8964:Fucophlorethol A 8789: 8768: 8761: 8754: 8745: 8606:Prenylflavonoids 8601:Pyranoflavonoids 8596:Furanoflavonoids 8524: 8442: 8370:Leucodelphinidin 8358:Flavan-3,4-diols 8280: 8261:Dalbergichromene 8176: 8167: 8146: 8139: 8132: 8123: 8100: 8093: 8086: 8077: 8013: 8006: 7999: 7990: 7806: 7799: 7792: 7783: 7387:Alkylresorcinols 7251:Chlorogenic acid 7026: 7017: 6997: 6990: 6983: 6974: 6924:Phenylpropanoids 6896:Diarylheptanoids 6772:Fucophlorethol A 6597: 6576: 6569: 6562: 6553: 6414:Prenylflavonoids 6409:Pyranoflavonoids 6404:Furanoflavonoids 6332: 6250: 6178:Leucodelphinidin 6166:Flavan-3,4-diols 6088: 6069:Dalbergichromene 5984: 5975: 5954: 5947: 5940: 5931: 5908: 5901: 5894: 5885: 5821: 5814: 5807: 5798: 5591: 5423: 5400:Sesterterpenoids 5366:Levopimaric acid 5228:Geranyl-linalool 5209: 5142:Sesquiterpenoids 5082:Perillyl alcohol 4996: 4891: 4770: 4763: 4756: 4747: 4724: 4717: 4710: 4701: 4682: 4681: 4657: 4651: 4650: 4640: 4608: 4602: 4601: 4585: 4575: 4569: 4568: 4566: 4564: 4543: 4537: 4536: 4534: 4532: 4526: 4518: 4512: 4511: 4509: 4507: 4492: 4482: 4476: 4475: 4455: 4449: 4448: 4420: 4411: 4410: 4400: 4376: 4370: 4369: 4359: 4327: 4321: 4320: 4318: 4316: 4301: 4295: 4294: 4292: 4290: 4279: 4266: 4265: 4263: 4261: 4250: 4244: 4243: 4241: 4232: 4226: 4225: 4215: 4205: 4181: 4175: 4174: 4140: 4131: 4125: 4124: 4079: 4070: 4069: 4059: 4042:(5): 1067–1078. 4027: 4021: 4020: 4010: 3978: 3972: 3971: 3923: 3917: 3916: 3906: 3889:(1): 249S–285S. 3874: 3868: 3867: 3827: 3821: 3820: 3792: 3786: 3785: 3757: 3751: 3750: 3740: 3708: 3702: 3701: 3699: 3676: 3670: 3669: 3664: 3662: 3651: 3645: 3644: 3642: 3619: 3613: 3612: 3607: 3605: 3594: 3588: 3587: 3579: 3570: 3569: 3567: 3565: 3554: 3548: 3547: 3545: 3543: 3532: 3526: 3525: 3523: 3521: 3510: 3504: 3503: 3501: 3478: 3472: 3471: 3461: 3451: 3427: 3421: 3420: 3403:(4): 1376–1386. 3392: 3386: 3385: 3375: 3351: 3345: 3332: 3326: 3325: 3315: 3291: 3285: 3284: 3274: 3250: 3244: 3243: 3233: 3223: 3214:(4): 1321–1342. 3199: 3193: 3192: 3182: 3150: 3144: 3143: 3123: 3117: 3116: 3088: 3082: 3081: 3071: 3047: 3041: 3040: 3012: 3006: 3005: 2985: 2979: 2978: 2958: 2952: 2951: 2933: 2909: 2903: 2884: 2878: 2877: 2861: 2855: 2854: 2838: 2832: 2831: 2803: 2797: 2796: 2786: 2769:(877): 485–503. 2754: 2748: 2747: 2719: 2713: 2712: 2684: 2678: 2677: 2649: 2643: 2642: 2622: 2616: 2615: 2605: 2599: 2598: 2580: 2574: 2573: 2550: 2544: 2543: 2515: 2509: 2508: 2499:(5): 1638–1643. 2488: 2482: 2481: 2471: 2454:(8): 3396–3402. 2443: 2437: 2436: 2399: 2393: 2392: 2375:(4): 1156–1161. 2364: 2358: 2357: 2337: 2331: 2330: 2286: 2280: 2279: 2278: 2272: 2262: 2238: 2232: 2231: 2211: 2205: 2204: 2168: 2162: 2161: 2127: 2118: 2112: 2111: 2093: 2084: 2078: 2077: 2060:(9): 1121–1125. 2049: 2043: 2042: 2014: 2008: 2007: 1979: 1973: 1972: 1955:(1): E101–E107. 1943: 1930: 1929: 1901: 1895: 1894: 1878: 1869: 1863: 1862: 1834: 1828: 1827: 1822: 1789: 1783: 1782: 1775: 1769: 1759: 1753: 1752: 1724: 1718: 1717: 1707: 1683: 1672: 1671: 1669: 1667: 1656: 1650: 1649: 1623: 1614: 1608: 1607: 1605: 1603: 1592: 1569: 1568: 1558: 1534: 1436:hemolytic anemia 1386:non-prescription 1294:chlorogenic acid 1049:of polyphenols. 692:autofluorescence 582:, high-pressure 510:carboxylic acids 489:and its 10-atom 417:Polyphenols are 282:WBSSH definition 181: 175: 174: 137:tanning garments 110: 109: 106: 105: 102: 99: 94: 93: 90: 87: 84: 81: 78: 75: 72: 69: 66: 63: 21: 9645: 9644: 9640: 9639: 9638: 9636: 9635: 9634: 9615: 9614: 9613: 9608: 9583: 9557: 9530:Phenylethanoids 9520: 9472: 9448:Diferulic acids 9405: 9384: 9321: 9312:Orsellinic acid 9258: 9242: 9198: 9193: 9151: 9136: 9110:Naphthoquinones 9072: 9021: 9012:Epicutissimin A 9004: 8996: 8915: 8873: 8850: 8778: 8772: 8734: 8720: 8693: 8685: 8663: 8659: 8651: 8633: 8620: 8563: 8551:Dihydrochalcone 8545: 8513: 8486: 8463: 8427: 8403: 8375: 8352: 8331: 8323: 8302: 8294: 8265: 8247: 8220: 8197: 8156: 8150: 8118: 8110: 8104: 8066: 8023: 8017: 7987: 7982: 7970: 7942: 7909: 7881: 7869:Natural phenols 7863: 7825: 7815: 7810: 7780: 7775: 7760: 7715:Polysaccharides 7698:Monosaccharides 7684: 7621: 7603: 7561: 7462:Isothiocyanates 7447:Gluconasturtiin 7437:isothiocyanates 7422: 7421: 7416: 7391: 7365: 7338:Phenylethanoids 7328: 7280: 7256:Diferulic acids 7213: 7192: 7129: 7120:Orsellinic acid 7066: 7050: 7006: 7001: 6959: 6944: 6918:Naphthoquinones 6880: 6829: 6820:Epicutissimin A 6812: 6804: 6723: 6681: 6658: 6586: 6580: 6542: 6528: 6501: 6493: 6471: 6467: 6459: 6441: 6428: 6371: 6359:Dihydrochalcone 6353: 6321: 6294: 6271: 6235: 6211: 6183: 6160: 6139: 6131: 6110: 6102: 6073: 6055: 6028: 6005: 5964: 5958: 5926: 5918: 5912: 5874: 5831: 5825: 5785: 5784: 5779: 5756: 5734: 5717: 5686: 5642: 5582: 5580:Tetraterpenoids 5574: 5553: 5494: 5485:Cholecalciferol 5411: 5408:Geranylfarnesol 5390: 5373:Neoabietic acid 5358:Isopimaric acid 5333: 5307: 5277: 5252: 5231: 5197: 5132: 5091: 5040: 4991: 4990:Monoterpenoids 4981: 4936: 4910: 4886: 4882: 4878: 4870: 4866:Isovaleric acid 4856: 4852: 4832: 4789: 4774: 4734: 4728: 4691: 4686: 4685: 4659: 4658: 4654: 4610: 4609: 4605: 4594: 4583: 4577: 4576: 4572: 4562: 4560: 4545: 4544: 4540: 4530: 4528: 4524: 4520: 4519: 4515: 4505: 4503: 4501: 4490: 4484: 4483: 4479: 4457: 4456: 4452: 4437: 4422: 4421: 4414: 4398:10.1002/fft2.25 4378: 4377: 4373: 4329: 4328: 4324: 4314: 4312: 4303: 4302: 4298: 4288: 4286: 4281: 4280: 4269: 4259: 4257: 4252: 4251: 4247: 4239: 4234: 4233: 4229: 4183: 4182: 4178: 4138: 4133: 4132: 4128: 4081: 4080: 4073: 4029: 4028: 4024: 3993:(5): CD008893. 3980: 3979: 3975: 3925: 3924: 3920: 3876: 3875: 3871: 3829: 3828: 3824: 3794: 3793: 3789: 3759: 3758: 3754: 3710: 3709: 3705: 3678: 3677: 3673: 3660: 3658: 3653: 3652: 3648: 3633:(5). May 2014. 3621: 3620: 3616: 3603: 3601: 3596: 3595: 3591: 3581: 3580: 3573: 3563: 3561: 3556: 3555: 3551: 3541: 3539: 3534: 3533: 3529: 3519: 3517: 3512: 3511: 3507: 3480: 3479: 3475: 3429: 3428: 3424: 3394: 3393: 3389: 3353: 3352: 3348: 3343:Wayback Machine 3333: 3329: 3293: 3292: 3288: 3252: 3251: 3247: 3201: 3200: 3196: 3152: 3151: 3147: 3125: 3124: 3120: 3090: 3089: 3085: 3049: 3048: 3044: 3014: 3013: 3009: 2987: 2986: 2982: 2960: 2959: 2955: 2911: 2910: 2906: 2885: 2881: 2863: 2862: 2858: 2840: 2839: 2835: 2805: 2804: 2800: 2756: 2755: 2751: 2721: 2720: 2716: 2686: 2685: 2681: 2651: 2650: 2646: 2633:(12): 665–673. 2624: 2623: 2619: 2607: 2606: 2602: 2595: 2582: 2581: 2577: 2567: 2552: 2551: 2547: 2517: 2516: 2512: 2490: 2489: 2485: 2445: 2444: 2440: 2401: 2400: 2396: 2366: 2365: 2361: 2339: 2338: 2334: 2288: 2287: 2283: 2273: 2240: 2239: 2235: 2213: 2212: 2208: 2170: 2169: 2165: 2125: 2120: 2119: 2115: 2096:Food Bioscience 2091: 2086: 2085: 2081: 2051: 2050: 2046: 2016: 2015: 2011: 1981: 1980: 1976: 1945: 1944: 1933: 1903: 1902: 1898: 1891: 1876: 1871: 1870: 1866: 1836: 1835: 1831: 1820: 1791: 1790: 1786: 1777: 1776: 1772: 1760: 1756: 1726: 1725: 1721: 1685: 1684: 1675: 1665: 1663: 1658: 1657: 1653: 1626:Pure Appl. Chem 1621: 1616: 1615: 1611: 1601: 1599: 1594: 1593: 1572: 1536: 1535: 1528: 1523: 1491: 1475:furanocoumarins 1428:Adverse effects 1425: 1413: 1359: 1353: 1334: 1322: 1306: 1279: 1248:clinical trials 1192:, as exist for 1178: 1145: 1089: 1081:Main articles: 1079: 1073: 1004:phenylpropanoid 1000:natural phenols 996: 936: 897:natural phenols 893:nutrient cycles 885: 853: 827:leather tanning 819: 807:absolute values 708: 684: 619:natural phenols 611: 599:ultrafiltration 557: 533: 499:hydroxyl groups 438: 421:species toward 396: 358:phenylpropanoid 334: 284: 233:(tea, fruits), 219:hydroxyl groups 204: 164: 96: 60: 56: 42:phenylpropanoid 28: 23: 22: 15: 12: 11: 5: 9643: 9641: 9633: 9632: 9630:Phytochemicals 9627: 9617: 9616: 9610: 9609: 9607: 9606: 9600: 9594: 9592: 9585: 9584: 9582: 9581: 9576: 9571: 9565: 9563: 9559: 9558: 9556: 9555: 9550: 9545: 9543:Hydroxytyrosol 9540: 9534: 9532: 9526: 9525: 9522: 9521: 9519: 9518: 9513: 9508: 9503: 9498: 9493: 9488: 9482: 9480: 9474: 9473: 9471: 9470: 9468:Sinapinic acid 9465: 9460: 9455: 9450: 9445: 9440: 9435: 9430: 9425: 9419: 9417: 9411: 9410: 9407: 9406: 9404: 9403: 9398: 9392: 9390: 9386: 9385: 9383: 9382: 9377: 9372: 9367: 9362: 9357: 9352: 9347: 9342: 9337: 9331: 9329: 9323: 9322: 9320: 9319: 9314: 9309: 9304: 9299: 9294: 9289: 9284: 9279: 9272: 9270: 9264: 9263: 9260: 9259: 9257: 9256: 9250: 9248: 9244: 9243: 9241: 9240: 9238:Salicylic acid 9235: 9230: 9224: 9222: 9215: 9206: 9204:Phenolic acids 9200: 9199: 9196:Aromatic acids 9194: 9192: 9191: 9184: 9177: 9169: 9163: 9161:Aromatic acids 9157: 9156: 9153: 9152: 9147: 9145: 9138: 9137: 9135: 9134: 9125: 9119: 9113: 9107: 9102: 9096: 9094:Anthraquinones 9091: 9084: 9082: 9078: 9077: 9074: 9073: 9071: 9070: 9069: 9068: 9063: 9058: 9053: 9045: 9040: 9038:Pseudo tannins 9035: 9033:Tannin sources 9029: 9027: 9023: 9022: 9020: 9019: 9014: 9008: 9006: 8998: 8997: 8995: 8994: 8991: 8986: 8981: 8976: 8971: 8966: 8961: 8956: 8951: 8946: 8941: 8936: 8931: 8925: 8923: 8917: 8916: 8914: 8913: 8908: 8903: 8898: 8893: 8887: 8885: 8879: 8878: 8875: 8874: 8872: 8871: 8866: 8860: 8858: 8852: 8851: 8849: 8848: 8843: 8838: 8833: 8828: 8823: 8818: 8813: 8808: 8803: 8797: 8795: 8786: 8780: 8779: 8773: 8771: 8770: 8763: 8756: 8748: 8742: 8736: 8735: 8730: 8728: 8722: 8721: 8719: 8718: 8713: 8708: 8703: 8697: 8695: 8687: 8686: 8684: 8683: 8678: 8673: 8667: 8665: 8661: 8653: 8652: 8647: 8645: 8643:Flavonolignans 8639: 8638: 8635: 8634: 8629: 8626: 8625: 8622: 8621: 8619: 8618: 8613: 8611:Methylenedioxy 8608: 8603: 8598: 8593: 8588: 8583: 8577: 8575: 8569: 8568: 8565: 8564: 8562: 8561: 8555: 8553: 8547: 8546: 8544: 8543: 8532: 8530: 8521: 8515: 8514: 8512: 8511: 8506: 8500: 8498: 8492: 8491: 8488: 8487: 8485: 8484: 8481:Guibourtinidin 8473: 8471: 8465: 8464: 8462: 8461: 8450: 8448: 8439: 8437:Anthocyanidins 8433: 8432: 8429: 8428: 8426: 8425: 8419: 8413: 8411: 8405: 8404: 8402: 8401: 8396: 8391: 8385: 8383: 8377: 8376: 8374: 8373: 8362: 8360: 8354: 8353: 8351: 8350: 8339: 8337: 8325: 8324: 8322: 8321: 8310: 8308: 8296: 8295: 8293: 8292: 8286: 8284: 8277: 8271: 8270: 8267: 8266: 8264: 8263: 8257: 8255: 8249: 8248: 8246: 8245: 8230: 8228: 8222: 8221: 8219: 8218: 8207: 8205: 8199: 8198: 8196: 8195: 8184: 8182: 8173: 8164: 8158: 8157: 8151: 8149: 8148: 8141: 8134: 8126: 8120: 8112: 8111: 8105: 8103: 8102: 8095: 8088: 8080: 8074: 8068: 8067: 8065: 8064: 8059: 8054: 8049: 8044: 8039: 8033: 8031: 8025: 8024: 8018: 8016: 8015: 8008: 8001: 7993: 7984: 7983: 7980: 7978: 7972: 7971: 7969: 7968: 7963: 7958: 7952: 7950: 7944: 7943: 7941: 7940: 7935: 7930: 7925: 7919: 7917: 7911: 7910: 7908: 7907: 7902: 7897: 7891: 7889: 7887:Monoterpenoids 7883: 7882: 7880: 7879: 7873: 7871: 7865: 7864: 7862: 7861: 7856: 7851: 7846: 7841: 7835: 7833: 7827: 7826: 7823: 7821: 7817: 7816: 7811: 7809: 7808: 7801: 7794: 7786: 7777: 7776: 7771: 7769: 7762: 7761: 7759: 7758: 7757: 7756: 7751: 7746: 7745: 7744: 7734: 7733: 7732: 7727: 7712: 7711: 7710: 7705: 7694: 7692: 7686: 7685: 7683: 7682: 7677: 7672: 7667: 7662: 7660:Anacardic acid 7657: 7652: 7647: 7646: 7645: 7640: 7631: 7629: 7623: 7622: 7620: 7619: 7613: 7611: 7605: 7604: 7602: 7601: 7600: 7599: 7594: 7584: 7583: 7582: 7571: 7569: 7563: 7562: 7560: 7559: 7558: 7557: 7552: 7547: 7542: 7537: 7532: 7527: 7517: 7516: 7515: 7514: 7513: 7503: 7496:Organosulfides 7493: 7492: 7491: 7486: 7481: 7480: 7479: 7474: 7469: 7456: 7455: 7454: 7449: 7444: 7432: 7430: 7428:Glucosinolates 7424: 7423: 7418: 7417: 7415: 7414: 7408: 7402: 7400: 7393: 7392: 7390: 7389: 7384: 7379: 7373: 7371: 7367: 7366: 7364: 7363: 7358: 7353: 7351:Hydroxytyrosol 7348: 7342: 7340: 7334: 7333: 7330: 7329: 7327: 7326: 7321: 7316: 7311: 7306: 7301: 7296: 7290: 7288: 7282: 7281: 7279: 7278: 7276:Sinapinic acid 7273: 7268: 7263: 7258: 7253: 7248: 7243: 7238: 7233: 7227: 7225: 7219: 7218: 7215: 7214: 7212: 7211: 7206: 7200: 7198: 7194: 7193: 7191: 7190: 7185: 7180: 7175: 7170: 7165: 7160: 7155: 7150: 7145: 7139: 7137: 7131: 7130: 7128: 7127: 7122: 7117: 7112: 7107: 7102: 7097: 7092: 7087: 7080: 7078: 7072: 7071: 7068: 7067: 7065: 7064: 7058: 7056: 7052: 7051: 7049: 7048: 7046:Salicylic acid 7043: 7038: 7032: 7030: 7023: 7014: 7012:Phenolic acids 7008: 7007: 7004:Aromatic acids 7002: 7000: 6999: 6992: 6985: 6977: 6971: 6969:Aromatic acids 6965: 6964: 6961: 6960: 6955: 6953: 6946: 6945: 6943: 6942: 6933: 6927: 6921: 6915: 6910: 6904: 6902:Anthraquinones 6899: 6892: 6890: 6886: 6885: 6882: 6881: 6879: 6878: 6877: 6876: 6871: 6866: 6861: 6853: 6848: 6846:Pseudo tannins 6843: 6841:Tannin sources 6837: 6835: 6831: 6830: 6828: 6827: 6822: 6816: 6814: 6806: 6805: 6803: 6802: 6799: 6794: 6789: 6784: 6779: 6774: 6769: 6764: 6759: 6754: 6749: 6744: 6739: 6733: 6731: 6725: 6724: 6722: 6721: 6716: 6711: 6706: 6701: 6695: 6693: 6687: 6686: 6683: 6682: 6680: 6679: 6674: 6668: 6666: 6660: 6659: 6657: 6656: 6651: 6646: 6641: 6636: 6631: 6626: 6621: 6616: 6611: 6605: 6603: 6594: 6588: 6587: 6581: 6579: 6578: 6571: 6564: 6556: 6550: 6544: 6543: 6538: 6536: 6530: 6529: 6527: 6526: 6521: 6516: 6511: 6505: 6503: 6495: 6494: 6492: 6491: 6486: 6481: 6475: 6473: 6469: 6461: 6460: 6455: 6453: 6451:Flavonolignans 6447: 6446: 6443: 6442: 6437: 6434: 6433: 6430: 6429: 6427: 6426: 6421: 6419:Methylenedioxy 6416: 6411: 6406: 6401: 6396: 6391: 6385: 6383: 6377: 6376: 6373: 6372: 6370: 6369: 6363: 6361: 6355: 6354: 6352: 6351: 6340: 6338: 6329: 6323: 6322: 6320: 6319: 6314: 6308: 6306: 6300: 6299: 6296: 6295: 6293: 6292: 6289:Guibourtinidin 6281: 6279: 6273: 6272: 6270: 6269: 6258: 6256: 6247: 6245:Anthocyanidins 6241: 6240: 6237: 6236: 6234: 6233: 6227: 6221: 6219: 6213: 6212: 6210: 6209: 6204: 6199: 6193: 6191: 6185: 6184: 6182: 6181: 6170: 6168: 6162: 6161: 6159: 6158: 6147: 6145: 6133: 6132: 6130: 6129: 6118: 6116: 6104: 6103: 6101: 6100: 6094: 6092: 6085: 6079: 6078: 6075: 6074: 6072: 6071: 6065: 6063: 6057: 6056: 6054: 6053: 6038: 6036: 6030: 6029: 6027: 6026: 6015: 6013: 6007: 6006: 6004: 6003: 5992: 5990: 5981: 5972: 5966: 5965: 5959: 5957: 5956: 5949: 5942: 5934: 5928: 5920: 5919: 5913: 5911: 5910: 5903: 5896: 5888: 5882: 5876: 5875: 5873: 5872: 5867: 5862: 5857: 5852: 5847: 5841: 5839: 5833: 5832: 5826: 5824: 5823: 5816: 5809: 5801: 5795: 5793: 5787: 5786: 5781: 5780: 5778: 5777: 5771: 5764: 5762: 5758: 5757: 5755: 5754: 5751:protein domain 5742: 5740: 5736: 5735: 5733: 5732: 5729: 5725: 5723: 5719: 5718: 5716: 5715: 5712: 5707: 5705:Natural rubber 5701: 5699: 5696:Polyterpenoids 5692: 5691: 5688: 5687: 5685: 5684: 5679: 5674: 5669: 5664: 5659: 5653: 5651: 5644: 5643: 5641: 5640: 5635: 5630: 5625: 5620: 5618:Delta-Carotene 5615: 5613:Gamma-Carotene 5610: 5605: 5603:Alpha-Carotene 5599: 5597: 5588: 5576: 5575: 5573: 5572: 5569: 5565: 5563: 5559: 5558: 5555: 5554: 5552: 5551: 5550: 5549: 5544: 5542:Betulinic acid 5539: 5534: 5532:Oleanolic acid 5526: 5521: 5518: 5513: 5508: 5502: 5500: 5496: 5495: 5493: 5492: 5487: 5482: 5477: 5472: 5467: 5466: 5465: 5460: 5455: 5450: 5445: 5444:Citrostadienol 5442: 5431: 5429: 5420: 5413: 5412: 5410: 5409: 5405: 5403: 5396: 5395: 5392: 5391: 5389: 5388: 5387:Palustric acid 5385: 5382: 5379: 5374: 5371: 5368: 5363: 5360: 5355: 5352: 5349: 5343: 5341: 5335: 5334: 5332: 5331: 5326: 5321: 5315: 5313: 5309: 5308: 5306: 5305: 5302: 5299: 5296: 5291: 5285: 5283: 5279: 5278: 5276: 5275: 5270: 5267: 5260: 5258: 5254: 5253: 5251: 5250: 5245: 5239: 5237: 5233: 5232: 5230: 5229: 5226: 5221: 5215: 5213: 5206: 5199: 5198: 5196: 5195: 5192: 5189: 5184: 5181: 5176: 5173: 5168: 5163: 5158: 5153: 5147: 5145: 5138: 5137: 5134: 5133: 5131: 5130: 5125: 5120: 5115: 5113:Bornyl acetate 5110: 5105: 5099: 5097: 5093: 5092: 5090: 5089: 5084: 5079: 5074: 5064: 5059: 5054: 5048: 5046: 5042: 5041: 5039: 5038: 5033: 5028: 5023: 5018: 5013: 5008: 5002: 5000: 4993: 4987: 4986: 4983: 4982: 4980: 4979: 4974: 4969: 4964: 4959: 4944: 4942: 4938: 4937: 4935: 4934: 4929: 4924: 4918: 4916: 4912: 4911: 4909: 4908: 4903: 4897: 4895: 4888: 4884: 4880: 4872: 4871: 4869: 4868: 4863: 4858: 4854: 4850: 4843: 4841: 4838:Hemiterpenoids 4834: 4833: 4831: 4830: 4824: 4821: 4815: 4812: 4809: 4797: 4795: 4791: 4790: 4775: 4773: 4772: 4765: 4758: 4750: 4744: 4742: 4736: 4735: 4732:phytochemicals 4729: 4727: 4726: 4719: 4712: 4704: 4698: 4697: 4690: 4689:External links 4687: 4684: 4683: 4652: 4603: 4592: 4570: 4538: 4513: 4499: 4477: 4450: 4435: 4412: 4391:(2): 109–133. 4385:Food Frontiers 4371: 4322: 4296: 4267: 4245: 4227: 4196:(6): 432–443. 4176: 4126: 4071: 4022: 3973: 3918: 3869: 3822: 3803:(7): 838–849. 3787: 3768:(7): 838–849. 3752: 3703: 3671: 3646: 3614: 3589: 3571: 3549: 3527: 3505: 3473: 3422: 3387: 3346: 3327: 3306:(1): 139–147. 3286: 3245: 3194: 3165:(5): 270–278. 3145: 3118: 3083: 3042: 3017:Water Research 3007: 2996:(2): 144–149. 2980: 2969:(7): 939–948. 2963:Phytopathology 2953: 2904: 2892:Phytochemistry 2879: 2876:(31): 371–381. 2856: 2853:(19): 333–342. 2833: 2814:(1): 103–126. 2798: 2749: 2730:(6): 919–932. 2714: 2695:(6): 238–243. 2679: 2660:(5): 311–315. 2644: 2617: 2600: 2594:978-0240802770 2593: 2587:. p. 25. 2575: 2565: 2545: 2526:(3): 636–645. 2510: 2483: 2438: 2411:(2): 109–124. 2394: 2359: 2332: 2281: 2233: 2222:(2): 176–181. 2206: 2163: 2136:(8): 770–795. 2113: 2079: 2044: 2025:(1–2): 37–43. 2009: 1990:(1): 117–124. 1974: 1931: 1912:(2): 129–133. 1896: 1889: 1864: 1829: 1800:(4): 433–438. 1784: 1770: 1754: 1719: 1698:(5): 727–747. 1673: 1651: 1632:(3): 357–360. 1609: 1570: 1549:(3): 586–621. 1525: 1524: 1522: 1519: 1518: 1517: 1512: 1507: 1505:Phytochemistry 1502: 1497: 1490: 1487: 1440:hepatotoxicity 1424: 1421: 1417:gut microbiota 1412: 1411:Gut microbiome 1409: 1355:Main article: 1352: 1349: 1345:phytoestrogens 1333: 1332:Phytoestrogens 1330: 1321: 1318: 1305: 1302: 1278: 1275: 1233:hydroxytyrosol 1221:European Union 1186:dietary energy 1177: 1174: 1156:polymerization 1144: 1141: 1072: 1069: 1065:fruit browning 995: 992: 990:interactions. 975: 974: 967: 964: 957: 954: 951:plant pigments 947: 935: 932: 916:sclerotization 884: 881: 861:polymerization 852: 849: 818: 815: 737:technologies. 720:standard curve 707: 706:Quantification 704: 683: 680: 610: 607: 556: 553: 549:quantification 537:phytochemistry 532: 529: 442:macromolecules 437: 434: 395: 392: 333: 330: 329: 328: 322: 312: 311: 308: 305: 302: 283: 280: 279: 278: 264: 258: 223:aromatic rings 213:, a polyphenol 203: 200: 163: 160: 117:phenolic acids 26: 24: 14: 13: 10: 9: 6: 4: 3: 2: 9642: 9631: 9628: 9626: 9623: 9622: 9620: 9604: 9603:Phlorotannins 9601: 9599: 9596: 9595: 9593: 9590: 9586: 9580: 9577: 9575: 9572: 9570: 9567: 9566: 9564: 9560: 9554: 9551: 9549: 9546: 9544: 9541: 9539: 9536: 9535: 9533: 9531: 9527: 9517: 9514: 9512: 9509: 9507: 9504: 9502: 9499: 9497: 9494: 9492: 9489: 9487: 9486:phenylalanine 9484: 9483: 9481: 9479: 9475: 9469: 9466: 9464: 9461: 9459: 9456: 9454: 9453:Coumaric acid 9451: 9449: 9446: 9444: 9441: 9439: 9438:Cinnamic acid 9436: 9434: 9433:Chicoric acid 9431: 9429: 9426: 9424: 9421: 9420: 9418: 9416: 9412: 9402: 9399: 9397: 9394: 9393: 9391: 9387: 9381: 9378: 9376: 9375:Syringic acid 9373: 9371: 9368: 9366: 9363: 9361: 9358: 9356: 9353: 9351: 9350:Eudesmic acid 9348: 9346: 9345:Ethyl gallate 9343: 9341: 9340:Chebulic acid 9338: 9336: 9333: 9332: 9330: 9328: 9324: 9318: 9315: 9313: 9310: 9308: 9305: 9303: 9302:Gentisic acid 9300: 9298: 9295: 9293: 9290: 9288: 9285: 9283: 9280: 9277: 9274: 9273: 9271: 9269: 9265: 9255: 9252: 9251: 9249: 9245: 9239: 9236: 9234: 9231: 9229: 9226: 9225: 9223: 9219: 9216: 9214: 9210: 9207: 9205: 9201: 9197: 9190: 9185: 9183: 9178: 9176: 9171: 9170: 9167: 9164: 9162: 9158: 9150: 9146: 9143: 9139: 9133: 9129: 9126: 9123: 9120: 9117: 9114: 9111: 9108: 9106: 9103: 9100: 9097: 9095: 9092: 9089: 9086: 9085: 9083: 9079: 9067: 9064: 9062: 9059: 9057: 9054: 9052: 9049: 9048: 9046: 9044: 9041: 9039: 9036: 9034: 9031: 9030: 9028: 9024: 9018: 9017:Acutissimin A 9015: 9013: 9010: 9009: 9007: 9003: 8999: 8992: 8990: 8989:7-Phloroeckol 8987: 8985: 8982: 8980: 8977: 8975: 8972: 8970: 8967: 8965: 8962: 8960: 8957: 8955: 8952: 8950: 8947: 8945: 8942: 8940: 8937: 8935: 8932: 8930: 8927: 8926: 8924: 8922: 8921:Phlorotannins 8918: 8912: 8909: 8907: 8904: 8902: 8899: 8897: 8894: 8892: 8889: 8888: 8886: 8884: 8880: 8870: 8867: 8865: 8862: 8861: 8859: 8857: 8853: 8847: 8844: 8842: 8839: 8837: 8834: 8832: 8829: 8827: 8824: 8822: 8819: 8817: 8814: 8812: 8809: 8807: 8804: 8802: 8799: 8798: 8796: 8794: 8793:Ellagitannins 8790: 8787: 8785: 8781: 8777: 8769: 8764: 8762: 8757: 8755: 8750: 8749: 8746: 8743: 8741: 8737: 8733: 8729: 8727: 8723: 8717: 8714: 8712: 8709: 8707: 8706:Pterostilbene 8704: 8702: 8699: 8698: 8696: 8692: 8688: 8682: 8679: 8677: 8674: 8672: 8669: 8668: 8666: 8658: 8654: 8650: 8646: 8644: 8640: 8632: 8627: 8617: 8614: 8612: 8609: 8607: 8604: 8602: 8599: 8597: 8594: 8592: 8589: 8587: 8584: 8582: 8579: 8578: 8576: 8574: 8573:Miscellaneous 8570: 8560: 8557: 8556: 8554: 8552: 8548: 8541: 8537: 8534: 8533: 8531: 8529: 8525: 8522: 8520: 8516: 8510: 8507: 8505: 8502: 8501: 8499: 8497: 8493: 8482: 8478: 8475: 8474: 8472: 8470: 8466: 8459: 8455: 8452: 8451: 8449: 8447: 8443: 8440: 8438: 8434: 8423: 8420: 8418: 8415: 8414: 8412: 8410: 8406: 8400: 8397: 8395: 8392: 8390: 8387: 8386: 8384: 8382: 8378: 8371: 8367: 8366:Leucocyanidin 8364: 8363: 8361: 8359: 8355: 8348: 8344: 8341: 8340: 8338: 8335: 8330: 8326: 8319: 8318:Gallocatechol 8315: 8312: 8311: 8309: 8306: 8301: 8297: 8291: 8290:Luteoliflavan 8288: 8287: 8285: 8281: 8278: 8276: 8272: 8262: 8259: 8258: 8256: 8254: 8253:Neoflavonoids 8250: 8243: 8239: 8235: 8232: 8231: 8229: 8227: 8223: 8216: 8212: 8209: 8208: 8206: 8204: 8200: 8193: 8189: 8186: 8185: 8183: 8181: 8177: 8174: 8172: 8171:Anthoxanthins 8168: 8165: 8163: 8159: 8155: 8147: 8142: 8140: 8135: 8133: 8128: 8127: 8124: 8121: 8117: 8113: 8109: 8101: 8096: 8094: 8089: 8087: 8082: 8081: 8078: 8075: 8073: 8069: 8063: 8060: 8058: 8055: 8053: 8050: 8048: 8045: 8043: 8042:Benzenetriols 8040: 8038: 8035: 8034: 8032: 8030: 8026: 8022: 8014: 8009: 8007: 8002: 8000: 7995: 7994: 7991: 7979: 7977: 7973: 7967: 7964: 7962: 7959: 7957: 7954: 7953: 7951: 7949: 7945: 7939: 7936: 7934: 7931: 7929: 7926: 7924: 7921: 7920: 7918: 7916: 7912: 7906: 7903: 7901: 7898: 7896: 7893: 7892: 7890: 7888: 7884: 7878: 7875: 7874: 7872: 7870: 7866: 7860: 7857: 7855: 7852: 7850: 7847: 7845: 7842: 7840: 7837: 7836: 7834: 7832: 7828: 7822: 7818: 7814: 7807: 7802: 7800: 7795: 7793: 7788: 7787: 7784: 7774: 7770: 7767: 7763: 7755: 7752: 7750: 7747: 7743: 7740: 7739: 7738: 7735: 7731: 7728: 7726: 7723: 7722: 7721: 7718: 7717: 7716: 7713: 7709: 7706: 7704: 7701: 7700: 7699: 7696: 7695: 7693: 7691: 7690:Carbohydrates 7687: 7681: 7680:Fertaric acid 7678: 7676: 7675:Coutaric acid 7673: 7671: 7670:Caftaric acid 7668: 7666: 7663: 7661: 7658: 7656: 7655:Tartaric acid 7653: 7651: 7648: 7644: 7641: 7639: 7636: 7635: 7633: 7632: 7630: 7628: 7627:Organic acids 7624: 7618: 7617:Chlorophyllin 7615: 7614: 7612: 7610: 7606: 7598: 7595: 7593: 7592:Indicaxanthin 7590: 7589: 7588: 7585: 7581: 7578: 7577: 7576: 7573: 7572: 7570: 7568: 7564: 7556: 7553: 7551: 7548: 7546: 7543: 7541: 7538: 7536: 7533: 7531: 7528: 7526: 7523: 7522: 7521: 7518: 7512: 7509: 7508: 7507: 7504: 7502: 7499: 7498: 7497: 7494: 7490: 7487: 7485: 7482: 7478: 7475: 7473: 7470: 7468: 7465: 7464: 7463: 7460: 7459: 7457: 7453: 7452:Glucoraphanin 7450: 7448: 7445: 7443: 7440: 7439: 7438: 7435:Precursor to 7434: 7433: 7431: 7429: 7425: 7412: 7411:Phlorotannins 7409: 7407: 7404: 7403: 7401: 7398: 7394: 7388: 7385: 7383: 7380: 7378: 7375: 7374: 7372: 7368: 7362: 7359: 7357: 7354: 7352: 7349: 7347: 7344: 7343: 7341: 7339: 7335: 7325: 7322: 7320: 7317: 7315: 7312: 7310: 7307: 7305: 7302: 7300: 7297: 7295: 7294:phenylalanine 7292: 7291: 7289: 7287: 7283: 7277: 7274: 7272: 7269: 7267: 7264: 7262: 7261:Coumaric acid 7259: 7257: 7254: 7252: 7249: 7247: 7246:Cinnamic acid 7244: 7242: 7241:Chicoric acid 7239: 7237: 7234: 7232: 7229: 7228: 7226: 7224: 7220: 7210: 7207: 7205: 7202: 7201: 7199: 7195: 7189: 7186: 7184: 7183:Syringic acid 7181: 7179: 7176: 7174: 7171: 7169: 7166: 7164: 7161: 7159: 7158:Eudesmic acid 7156: 7154: 7153:Ethyl gallate 7151: 7149: 7148:Chebulic acid 7146: 7144: 7141: 7140: 7138: 7136: 7132: 7126: 7123: 7121: 7118: 7116: 7113: 7111: 7110:Gentisic acid 7108: 7106: 7103: 7101: 7098: 7096: 7093: 7091: 7088: 7085: 7082: 7081: 7079: 7077: 7073: 7063: 7060: 7059: 7057: 7053: 7047: 7044: 7042: 7039: 7037: 7034: 7033: 7031: 7027: 7024: 7022: 7018: 7015: 7013: 7009: 7005: 6998: 6993: 6991: 6986: 6984: 6979: 6978: 6975: 6972: 6970: 6966: 6958: 6954: 6951: 6947: 6941: 6937: 6934: 6931: 6928: 6925: 6922: 6919: 6916: 6914: 6911: 6908: 6905: 6903: 6900: 6897: 6894: 6893: 6891: 6887: 6875: 6872: 6870: 6867: 6865: 6862: 6860: 6857: 6856: 6854: 6852: 6849: 6847: 6844: 6842: 6839: 6838: 6836: 6832: 6826: 6825:Acutissimin A 6823: 6821: 6818: 6817: 6815: 6811: 6807: 6800: 6798: 6797:7-Phloroeckol 6795: 6793: 6790: 6788: 6785: 6783: 6780: 6778: 6775: 6773: 6770: 6768: 6765: 6763: 6760: 6758: 6755: 6753: 6750: 6748: 6745: 6743: 6740: 6738: 6735: 6734: 6732: 6730: 6729:Phlorotannins 6726: 6720: 6717: 6715: 6712: 6710: 6707: 6705: 6702: 6700: 6697: 6696: 6694: 6692: 6688: 6678: 6675: 6673: 6670: 6669: 6667: 6665: 6661: 6655: 6652: 6650: 6647: 6645: 6642: 6640: 6637: 6635: 6632: 6630: 6627: 6625: 6622: 6620: 6617: 6615: 6612: 6610: 6607: 6606: 6604: 6602: 6601:Ellagitannins 6598: 6595: 6593: 6589: 6585: 6577: 6572: 6570: 6565: 6563: 6558: 6557: 6554: 6551: 6549: 6545: 6541: 6537: 6535: 6531: 6525: 6522: 6520: 6517: 6515: 6514:Pterostilbene 6512: 6510: 6507: 6506: 6504: 6500: 6496: 6490: 6487: 6485: 6482: 6480: 6477: 6476: 6474: 6466: 6462: 6458: 6454: 6452: 6448: 6440: 6435: 6425: 6422: 6420: 6417: 6415: 6412: 6410: 6407: 6405: 6402: 6400: 6397: 6395: 6392: 6390: 6387: 6386: 6384: 6382: 6381:Miscellaneous 6378: 6368: 6365: 6364: 6362: 6360: 6356: 6349: 6345: 6342: 6341: 6339: 6337: 6333: 6330: 6328: 6324: 6318: 6315: 6313: 6310: 6309: 6307: 6305: 6301: 6290: 6286: 6283: 6282: 6280: 6278: 6274: 6267: 6263: 6260: 6259: 6257: 6255: 6251: 6248: 6246: 6242: 6231: 6228: 6226: 6223: 6222: 6220: 6218: 6214: 6208: 6205: 6203: 6200: 6198: 6195: 6194: 6192: 6190: 6186: 6179: 6175: 6174:Leucocyanidin 6172: 6171: 6169: 6167: 6163: 6156: 6152: 6149: 6148: 6146: 6143: 6138: 6134: 6127: 6126:Gallocatechol 6123: 6120: 6119: 6117: 6114: 6109: 6105: 6099: 6098:Luteoliflavan 6096: 6095: 6093: 6089: 6086: 6084: 6080: 6070: 6067: 6066: 6064: 6062: 6061:Neoflavonoids 6058: 6051: 6047: 6043: 6040: 6039: 6037: 6035: 6031: 6024: 6020: 6017: 6016: 6014: 6012: 6008: 6001: 5997: 5994: 5993: 5991: 5989: 5985: 5982: 5980: 5979:Anthoxanthins 5976: 5973: 5971: 5967: 5963: 5955: 5950: 5948: 5943: 5941: 5936: 5935: 5932: 5929: 5925: 5921: 5917: 5909: 5904: 5902: 5897: 5895: 5890: 5889: 5886: 5883: 5881: 5877: 5871: 5868: 5866: 5863: 5861: 5858: 5856: 5853: 5851: 5850:Benzenetriols 5848: 5846: 5843: 5842: 5840: 5838: 5834: 5830: 5822: 5817: 5815: 5810: 5808: 5803: 5802: 5799: 5794: 5792: 5788: 5775: 5772: 5769: 5766: 5765: 5763: 5759: 5752: 5748: 5744: 5743: 5741: 5737: 5730: 5728:3-oxo-α-ionol 5727: 5726: 5724: 5720: 5713: 5711: 5708: 5706: 5703: 5702: 5700: 5697: 5693: 5683: 5680: 5678: 5675: 5673: 5670: 5668: 5665: 5663: 5662:Cryptoxanthin 5660: 5658: 5657:Canthaxanthin 5655: 5654: 5652: 5649: 5645: 5639: 5636: 5634: 5631: 5629: 5626: 5624: 5621: 5619: 5616: 5614: 5611: 5609: 5608:Beta-Carotene 5606: 5604: 5601: 5600: 5598: 5596: 5592: 5589: 5586: 5581: 5577: 5570: 5568:Ferrugicadiol 5567: 5566: 5564: 5560: 5548: 5545: 5543: 5540: 5538: 5535: 5533: 5530: 5529: 5527: 5525: 5522: 5520:Serratenediol 5519: 5517: 5514: 5512: 5509: 5507: 5504: 5503: 5501: 5497: 5491: 5488: 5486: 5483: 5481: 5478: 5476: 5473: 5471: 5468: 5464: 5461: 5459: 5456: 5454: 5451: 5449: 5446: 5443: 5441: 5438: 5437: 5436: 5433: 5432: 5430: 5428: 5424: 5421: 5418: 5417:Triterpenoids 5414: 5407: 5406: 5404: 5401: 5397: 5386: 5383: 5380: 5378: 5375: 5372: 5370:Mercusic acid 5369: 5367: 5364: 5361: 5359: 5356: 5353: 5351:Communic acid 5350: 5348: 5345: 5344: 5342: 5340: 5336: 5330: 5327: 5325: 5322: 5320: 5317: 5316: 5314: 5310: 5303: 5300: 5297: 5295: 5292: 5290: 5287: 5286: 5284: 5280: 5274: 5271: 5268: 5265: 5262: 5261: 5259: 5255: 5249: 5246: 5244: 5241: 5240: 5238: 5234: 5227: 5225: 5222: 5220: 5217: 5216: 5214: 5210: 5207: 5204: 5200: 5193: 5190: 5188: 5185: 5182: 5180: 5177: 5174: 5172: 5169: 5167: 5164: 5162: 5159: 5157: 5154: 5152: 5149: 5148: 5146: 5143: 5139: 5129: 5126: 5124: 5121: 5119: 5116: 5114: 5111: 5109: 5106: 5104: 5101: 5100: 5098: 5094: 5088: 5085: 5083: 5080: 5078: 5075: 5072: 5068: 5065: 5063: 5060: 5058: 5055: 5053: 5050: 5049: 5047: 5043: 5037: 5034: 5032: 5029: 5027: 5024: 5022: 5019: 5017: 5014: 5012: 5009: 5007: 5004: 5003: 5001: 4997: 4994: 4988: 4978: 4975: 4973: 4970: 4968: 4965: 4963: 4960: 4957: 4953: 4949: 4946: 4945: 4943: 4939: 4933: 4930: 4928: 4925: 4923: 4920: 4919: 4917: 4913: 4907: 4904: 4902: 4899: 4898: 4896: 4892: 4889: 4877: 4873: 4867: 4864: 4862: 4859: 4848: 4845: 4844: 4842: 4839: 4835: 4828: 4825: 4822: 4819: 4816: 4813: 4810: 4807: 4803: 4799: 4798: 4796: 4792: 4787: 4783: 4779: 4771: 4766: 4764: 4759: 4757: 4752: 4751: 4748: 4743: 4741: 4737: 4733: 4725: 4720: 4718: 4713: 4711: 4706: 4705: 4702: 4696: 4693: 4692: 4688: 4679: 4675: 4671: 4667: 4663: 4656: 4653: 4648: 4644: 4639: 4634: 4630: 4626: 4623:(4): e05239. 4622: 4618: 4614: 4607: 4604: 4600: 4595: 4593:9780117069923 4589: 4582: 4581: 4574: 4571: 4558: 4554: 4553: 4548: 4542: 4539: 4523: 4517: 4514: 4502: 4500:9780117069923 4496: 4489: 4488: 4481: 4478: 4473: 4469: 4465: 4461: 4454: 4451: 4446: 4442: 4438: 4432: 4428: 4427: 4419: 4417: 4413: 4408: 4404: 4399: 4394: 4390: 4386: 4382: 4375: 4372: 4367: 4363: 4358: 4353: 4349: 4345: 4341: 4337: 4333: 4326: 4323: 4310: 4306: 4300: 4297: 4284: 4278: 4276: 4274: 4272: 4268: 4255: 4249: 4246: 4238: 4231: 4228: 4223: 4219: 4214: 4209: 4204: 4199: 4195: 4191: 4187: 4180: 4177: 4172: 4168: 4164: 4160: 4156: 4152: 4148: 4144: 4137: 4130: 4127: 4122: 4118: 4114: 4110: 4106: 4102: 4098: 4094: 4090: 4086: 4078: 4076: 4072: 4067: 4063: 4058: 4053: 4049: 4045: 4041: 4037: 4033: 4026: 4023: 4018: 4014: 4009: 4004: 4000: 3996: 3992: 3988: 3984: 3977: 3974: 3969: 3965: 3961: 3957: 3953: 3949: 3945: 3941: 3937: 3933: 3929: 3922: 3919: 3914: 3910: 3905: 3900: 3896: 3892: 3888: 3884: 3880: 3873: 3870: 3865: 3861: 3857: 3853: 3849: 3845: 3841: 3837: 3833: 3826: 3823: 3818: 3814: 3810: 3806: 3802: 3798: 3791: 3788: 3783: 3779: 3775: 3771: 3767: 3763: 3756: 3753: 3748: 3744: 3739: 3734: 3730: 3726: 3722: 3718: 3714: 3707: 3704: 3698: 3693: 3689: 3685: 3681: 3675: 3672: 3668: 3656: 3650: 3647: 3641: 3636: 3632: 3628: 3624: 3618: 3615: 3611: 3599: 3593: 3590: 3585: 3578: 3576: 3572: 3559: 3553: 3550: 3537: 3531: 3528: 3515: 3509: 3506: 3500: 3495: 3491: 3487: 3483: 3477: 3474: 3469: 3465: 3460: 3455: 3450: 3445: 3441: 3437: 3433: 3426: 3423: 3418: 3414: 3410: 3406: 3402: 3398: 3391: 3388: 3383: 3379: 3374: 3369: 3365: 3361: 3357: 3350: 3347: 3344: 3340: 3337: 3331: 3328: 3323: 3319: 3314: 3309: 3305: 3301: 3297: 3290: 3287: 3282: 3278: 3273: 3268: 3264: 3260: 3256: 3249: 3246: 3241: 3237: 3232: 3227: 3222: 3217: 3213: 3209: 3205: 3198: 3195: 3190: 3186: 3181: 3176: 3172: 3168: 3164: 3160: 3156: 3149: 3146: 3141: 3137: 3133: 3129: 3122: 3119: 3114: 3110: 3106: 3102: 3098: 3094: 3087: 3084: 3079: 3075: 3070: 3065: 3061: 3057: 3053: 3046: 3043: 3038: 3034: 3030: 3026: 3022: 3018: 3011: 3008: 3003: 2999: 2995: 2991: 2984: 2981: 2976: 2972: 2968: 2964: 2957: 2954: 2949: 2945: 2941: 2937: 2932: 2927: 2923: 2919: 2915: 2908: 2905: 2901: 2900:81-308-0034-9 2897: 2893: 2889: 2883: 2880: 2875: 2871: 2867: 2860: 2857: 2852: 2848: 2844: 2837: 2834: 2829: 2825: 2821: 2817: 2813: 2809: 2802: 2799: 2794: 2790: 2785: 2780: 2776: 2772: 2768: 2764: 2760: 2753: 2750: 2745: 2741: 2737: 2733: 2729: 2725: 2718: 2715: 2710: 2706: 2702: 2698: 2694: 2690: 2683: 2680: 2675: 2671: 2667: 2663: 2659: 2655: 2648: 2645: 2640: 2636: 2632: 2628: 2621: 2618: 2613: 2612: 2604: 2601: 2596: 2590: 2586: 2579: 2576: 2572: 2568: 2562: 2558: 2557: 2549: 2546: 2541: 2537: 2533: 2529: 2525: 2521: 2514: 2511: 2506: 2502: 2498: 2494: 2487: 2484: 2479: 2475: 2470: 2465: 2461: 2457: 2453: 2449: 2442: 2439: 2434: 2430: 2426: 2422: 2418: 2414: 2410: 2406: 2398: 2395: 2390: 2386: 2382: 2378: 2374: 2370: 2363: 2360: 2355: 2351: 2347: 2343: 2336: 2333: 2328: 2324: 2320: 2316: 2312: 2308: 2304: 2300: 2296: 2292: 2285: 2282: 2277: 2270: 2266: 2261: 2256: 2252: 2248: 2247:BioTechniques 2244: 2237: 2234: 2229: 2225: 2221: 2217: 2210: 2207: 2202: 2198: 2194: 2190: 2186: 2182: 2178: 2174: 2167: 2164: 2159: 2155: 2151: 2147: 2143: 2139: 2135: 2131: 2124: 2117: 2114: 2109: 2105: 2101: 2097: 2090: 2083: 2080: 2075: 2071: 2067: 2063: 2059: 2055: 2048: 2045: 2040: 2036: 2032: 2028: 2024: 2020: 2013: 2010: 2005: 2001: 1997: 1993: 1989: 1985: 1978: 1975: 1970: 1966: 1962: 1958: 1954: 1950: 1942: 1940: 1938: 1936: 1932: 1927: 1923: 1919: 1915: 1911: 1907: 1900: 1897: 1892: 1886: 1882: 1875: 1868: 1865: 1860: 1856: 1852: 1848: 1844: 1840: 1833: 1830: 1825: 1819: 1815: 1811: 1807: 1803: 1799: 1795: 1788: 1785: 1780: 1774: 1771: 1768: 1767:0-521-46513-3 1764: 1758: 1755: 1750: 1746: 1742: 1738: 1734: 1730: 1723: 1720: 1715: 1711: 1706: 1701: 1697: 1693: 1689: 1682: 1680: 1678: 1674: 1661: 1655: 1652: 1647: 1643: 1639: 1635: 1631: 1627: 1620: 1613: 1610: 1597: 1591: 1589: 1587: 1585: 1583: 1581: 1579: 1577: 1575: 1571: 1566: 1562: 1557: 1552: 1548: 1544: 1540: 1533: 1531: 1527: 1520: 1516: 1513: 1511: 1508: 1506: 1503: 1501: 1498: 1496: 1493: 1492: 1488: 1486: 1484: 1480: 1476: 1472: 1468: 1464: 1459: 1457: 1453: 1452:non-haem iron 1449: 1445: 1441: 1437: 1433: 1429: 1422: 1420: 1418: 1410: 1408: 1406: 1402: 1398: 1394: 1390: 1387: 1383: 1379: 1375: 1371: 1367: 1364: 1358: 1350: 1348: 1346: 1342: 1341:17ÎČ-estradiol 1338: 1331: 1329: 1327: 1319: 1317: 1314: 1309: 1303: 1301: 1299: 1295: 1291: 1287: 1283: 1276: 1274: 1272: 1268: 1264: 1260: 1255: 1253: 1249: 1244: 1242: 1238: 1234: 1230: 1226: 1225:health claims 1222: 1217: 1215: 1214:physiological 1211: 1207: 1203: 1199: 1195: 1191: 1187: 1183: 1175: 1173: 1171: 1168: 1165: 1161: 1157: 1152: 1150: 1142: 1140: 1138: 1134: 1130: 1126: 1121: 1119: 1115: 1111: 1107: 1106:antinutrients 1101: 1096: 1094: 1088: 1084: 1078: 1070: 1068: 1066: 1062: 1058: 1054: 1050: 1048: 1044: 1039: 1037: 1033: 1029: 1026:oxidation of 1025: 1021: 1017: 1016:phenylalanine 1013: 1009: 1008:shikimic acid 1005: 1001: 993: 991: 989: 985: 984: 979: 972: 968: 965: 962: 958: 955: 952: 948: 945: 941: 940: 939: 933: 931: 929: 925: 921: 917: 913: 909: 905: 900: 898: 894: 890: 882: 880: 878: 874: 870: 867:, as well as 866: 862: 858: 850: 848: 846: 841: 839: 836: 832: 828: 824: 816: 814: 812: 808: 804: 799: 797: 792: 790: 786: 782: 778: 774: 769: 767: 764:, which is a 763: 759: 755: 751: 747: 743: 738: 736: 732: 728: 723: 721: 717: 713: 705: 703: 701: 700:plant science 697: 693: 689: 688:DMACA reagent 681: 679: 677: 673: 669: 665: 661: 657: 653: 651: 647: 646:fractionation 643: 639: 635: 628: 624: 620: 615: 608: 606: 604: 600: 595: 593: 588: 585: 581: 577: 573: 569: 565: 561: 554: 552: 550: 546: 543:, isolation, 542: 538: 530: 526: 522: 517: 513: 511: 507: 504: 500: 492: 488: 482: 478: 476: 472: 468: 464: 460: 455: 451: 447: 443: 435: 433: 431: 428: 424: 420: 412: 408: 404: 400: 393: 391: 389: 385: 382: 377: 373: 369: 365: 363: 359: 355: 346: 342: 338: 331: 326: 323: 320: 317: 316: 315: 309: 306: 303: 300: 299:water-soluble 296: 295: 294: 291: 289: 281: 276: 272: 271:phenylalanine 268: 265: 263: 259: 256: 252: 248: 244: 240: 236: 232: 228: 227: 226: 224: 220: 212: 208: 201: 199: 197: 193: 189: 185: 180: 169: 168:Ancient Greek 161: 156: 155:Curcuma longa 152: 148: 144: 140: 138: 134: 130: 126: 122: 118: 114: 108: 54: 47: 43: 39: 34: 30: 19: 9588: 9463:Ferulic acid 9428:Caffeic acid 9401:Ellagic acid 9148: 9141: 9132:isocoumarins 9105:Kavalactones 9047:Tannin uses 8974:Tetrafucol A 8954:Diphlorethol 8939:6,6'-Bieckol 8934:8,8â€Č-Bieckol 8856:Gallotannins 8821:Casuarictins 8801:Punicalagins 8726:Curcuminoids 8671:Matairesinol 8572: 8477:Apigeninidin 8422:Aromadendrin 8329:Flavan-4-ols 8300:Flavan-3-ols 8107: 8071: 8037:Benzenediols 7966:Tetracycline 7961:Streptomycin 7915:Diterpenoids 7876: 7854:Tetrodotoxin 7765: 7609:Chlorophylls 7597:Vulgaxanthin 7587:Betaxanthins 7506:Polysulfides 7489:Thiocyanates 7467:Sulforaphane 7396: 7271:Ferulic acid 7236:Caffeic acid 7209:Ellagic acid 6956: 6949: 6940:isocoumarins 6913:Kavalactones 6855:Tannin uses 6782:Tetrafucol A 6762:Diphlorethol 6747:6,6'-Bieckol 6742:8,8â€Č-Bieckol 6664:Gallotannins 6629:Casuarictins 6609:Punicalagins 6534:Curcuminoids 6479:Matairesinol 6380: 6285:Apigeninidin 6230:Aromadendrin 6137:Flavan-4-ols 6108:Flavan-3-ols 5915: 5879: 5845:Benzenediols 5714:Gutta-balatĂĄ 5710:Gutta percha 5648:Xanthophylls 5628:Neurosporene 5547:Moronic acid 5537:Ursolic acid 5480:Testosterone 5463:Stigmasterol 5448:Cycloartenol 5435:Phytosterols 5377:Pimaric acid 5347:Abietic acid 5298:Manoyl oxide 5273:Salvinorin A 5263: 5203:Diterpenoids 5067:Thujaplicins 4992:(2,modified) 4932:Phellandrene 4876:Monoterpenes 4805: 4801: 4794:Basic forms: 4669: 4666:EFSA Journal 4665: 4655: 4620: 4617:EFSA Journal 4616: 4606: 4597: 4579: 4573: 4561:. Retrieved 4556: 4550: 4541: 4529:. Retrieved 4516: 4504:. Retrieved 4486: 4480: 4463: 4459: 4453: 4425: 4388: 4384: 4374: 4339: 4335: 4325: 4313:. Retrieved 4308: 4299: 4287:. Retrieved 4258:. Retrieved 4248: 4230: 4213:10072/389251 4193: 4189: 4179: 4146: 4142: 4129: 4088: 4084: 4039: 4035: 4025: 3990: 3986: 3976: 3938:(2): 77–81. 3935: 3931: 3921: 3886: 3882: 3872: 3839: 3835: 3825: 3800: 3796: 3790: 3765: 3761: 3755: 3738:10261/258758 3720: 3716: 3706: 3687: 3684:EFSA Journal 3683: 3674: 3666: 3659:. Retrieved 3649: 3630: 3627:EFSA Journal 3626: 3617: 3609: 3602:. Retrieved 3592: 3562:. Retrieved 3552: 3540:. Retrieved 3530: 3518:. Retrieved 3508: 3489: 3485: 3476: 3439: 3435: 3425: 3400: 3396: 3390: 3363: 3359: 3349: 3330: 3303: 3299: 3289: 3262: 3258: 3248: 3211: 3207: 3197: 3162: 3158: 3148: 3131: 3127: 3121: 3096: 3092: 3086: 3059: 3055: 3045: 3020: 3016: 3010: 2993: 2989: 2983: 2966: 2962: 2956: 2921: 2917: 2907: 2891: 2882: 2873: 2869: 2859: 2850: 2846: 2836: 2811: 2807: 2801: 2766: 2762: 2752: 2727: 2723: 2717: 2692: 2688: 2682: 2657: 2653: 2647: 2630: 2626: 2620: 2610: 2603: 2584: 2578: 2570: 2555: 2548: 2523: 2519: 2513: 2496: 2492: 2486: 2469:10261/112476 2451: 2447: 2441: 2408: 2404: 2397: 2372: 2368: 2362: 2345: 2341: 2335: 2294: 2290: 2284: 2253:(2): 65–71. 2250: 2246: 2236: 2219: 2215: 2209: 2176: 2172: 2166: 2133: 2129: 2116: 2099: 2095: 2082: 2057: 2053: 2047: 2022: 2018: 2012: 1987: 1983: 1977: 1952: 1948: 1909: 1905: 1899: 1880: 1867: 1842: 1838: 1832: 1797: 1793: 1787: 1773: 1757: 1735:(1): 41–66. 1732: 1728: 1722: 1695: 1691: 1664:. Retrieved 1660:"Polyphenol" 1654: 1629: 1625: 1612: 1600:. Retrieved 1596:"Flavonoids" 1546: 1542: 1460: 1426: 1414: 1401:medical food 1360: 1335: 1323: 1310: 1307: 1298:flavan-3-ols 1285: 1282:In the 1930s 1280: 1259:antioxidants 1256: 1246:As of 2022, 1245: 1239:complex and 1229:cocoa solids 1218: 1179: 1153: 1146: 1131:compared to 1122: 1103: 1098: 1090: 1051: 1040: 1023: 1012:gallotannins 1010:pathway for 997: 988:allelopathic 981: 976: 973:against rot. 971:preservation 961:phytoalexins 937: 934:Biochemistry 924:pigmentation 901: 886: 865:formaldehyde 854: 842: 820: 817:Applications 800: 793: 784: 770: 739: 727:colorimetric 724: 716:permanganate 709: 685: 654: 642:spectroscopy 632: 626: 596: 591: 589: 558: 534: 496: 453: 439: 427:antioxidants 416: 368:Ellagic acid 366: 351: 313: 292: 285: 262:caffeic acid 216: 211:Ellagic acid 195: 190:) ring to a 165: 154: 129:ellagitannin 52: 51: 29: 9625:Polyphenols 9548:Oleocanthal 9365:Norbergenin 9360:Tannic acid 9355:Gallic acid 9149:Polyphenols 9122:Xanthonoids 9099:Chalconoids 8949:Eckstolonol 8846:Terflavin B 8811:Vescalagins 8806:Castalagins 8711:Piceatannol 8701:Resveratrol 8691:Stilbenoids 8681:Pinoresinol 8616:Castavinols 8458:Delphinidin 8409:Flavanonols 8399:Eriodictyol 8226:Isoflavones 8108:polyphenols 8072:Polyphenols 7948:Antibiotics 7938:Pimaradiene 7933:Aphidicolin 7877:Polyphenols 7720:Beta-glucan 7650:Oxalic acid 7643:Quinic acid 7638:Phytic acid 7575:Betacyanins 7356:Oleocanthal 7173:Norbergenin 7168:Tannic acid 7163:Gallic acid 6957:Polyphenols 6930:Xanthonoids 6907:Chalconoids 6757:Eckstolonol 6654:Terflavin B 6619:Vescalagins 6614:Castalagins 6519:Piceatannol 6509:Resveratrol 6499:Stilbenoids 6489:Pinoresinol 6424:Castavinols 6266:Delphinidin 6217:Flavanonols 6207:Eriodictyol 6034:Isoflavones 5916:polyphenols 5880:Polyphenols 5682:Rubixanthin 5672:Astaxanthin 5633:Phytofluene 5585:Carotenoids 5475:Cholesterol 5470:Tocopherols 5440:Campesterol 5339:Resin acids 5324:Gibberellin 5319:Aphidicolin 5312:Tetracyclic 5187:Longifolene 5151:Artemisinin 5128:Umbellulone 5016:Citronellol 5006:Citronellal 4563:3 September 4531:3 September 4506:3 September 4466:: 379–394. 2193:10261/82508 2150:11336/87660 1666:23 February 1456:iron status 1384:. Some are 1382:hemorrhoids 1363:citrus peel 1351:Phlebotonic 1337:Isoflavones 1210:food labels 1160:epicatechin 1149:astringency 1143:Astringency 1059:to produce 1057:o-diphenols 1020:malonyl-CoA 914:hardening ( 908:crustaceans 835:pomegranate 791:oxidation. 475:epicatechin 388:tannic acid 376:gallic acid 360:and/or the 125:tannic acid 53:Polyphenols 46:gallic acid 38:tannic acid 9619:Categories 9553:Oleuropein 9491:tryptophan 9380:Theogallin 9247:Glycosides 9124:(C6-C1-C6) 9101:(C6-C3-C6) 9090:(C6-C7-C6) 9051:Enological 8831:Punicalins 8826:Grandinins 8716:Pinosylvin 8694:(C6-C2-C6) 8509:Leptosidin 8504:Aureusidin 8394:Naringenin 8389:Hesperidin 8381:Flavanones 8347:Luteoforol 8215:Kaempferol 8162:Flavonoids 8154:flavonoids 8119:(C6-C3-C6) 8116:Flavonoids 8062:Dillapiole 7956:Penicillin 7665:Malic acid 7361:Oleuropein 7299:tryptophan 7188:Theogallin 7055:Glycosides 6932:(C6-C1-C6) 6909:(C6-C3-C6) 6898:(C6-C7-C6) 6859:Enological 6639:Punicalins 6634:Grandinins 6524:Pinosylvin 6502:(C6-C2-C6) 6317:Leptosidin 6312:Aureusidin 6202:Naringenin 6197:Hesperidin 6189:Flavanones 6155:Luteoforol 6023:Kaempferol 5970:Flavonoids 5962:flavonoids 5927:(C6-C3-C6) 5924:Flavonoids 5870:Dillapiole 5667:Zeaxanthin 5511:Lanosterol 5458:Sitosterol 5453:Sitostanol 5329:Paclitaxel 5236:Monocyclic 5123:Ascaridole 5118:Eucalyptol 5071:Hinokitiol 5045:Monocyclic 4915:Monocyclic 4782:terpenoids 4740:Terpenoids 4315:8 November 4289:7 November 4149:: 96–105. 3842:: 101116. 3723:: 110655. 1602:28 October 1521:References 1448:absorption 1397:Diosmiplex 1391:, such as 1374:hesperidin 1372:, such as 1370:flavonoids 1252:biomarkers 1237:oleuropein 1125:carotenoid 1075:See also: 1061:o-quinones 1047:solubility 912:epicuticle 904:arthropods 883:Occurrence 796:biosensors 660:separation 560:Extraction 555:Extraction 541:extraction 491:benzopyran 487:isoflavone 407:theaflavin 362:polyketide 235:hesperetin 202:Definition 121:flavonoids 9569:Capsaicin 9506:thyroxine 9496:histidine 9221:Aglycones 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Index

Health effects of phenols and polyphenols

tannic acid
phenylpropanoid
gallic acid
/ˌpɒliˈfiːnoʊl,-nɒl/
phenols
phenolic acids
flavonoids
tannic acid
ellagitannin
dyes
tanning garments

Curcumin
turmeric
Ancient Greek
benzenoid
phenyl
hydroxyl

Ellagic acid
hydroxyl groups
aromatic rings
catechin
hesperetin
cyanidin
daidzein
soybean
proanthocyanidins

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