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Draft:List of polyphenols

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The polyphenols are a class of phytochemicals.[1]

Class

[edit]

Polyphenols groups are classified on the basis of differing strengths of the phenolic ring.[2]

Quantity

[edit]

In a survey of total polyphenol content of 100 foods including beans and bean products, cereals, fruits, herbs, spices, tea, vegetables, and wine, cloves were found to have the most (1st) with dried peppermint (2nd) having a similar range (10000 range mg/ml per 100 g); star anise was found to have the 3rd most polyphenol quantity - in a similar range (1000s mg/ml per 100g) 4th: cocoa powder, 5th: dried Mexican oregano, 6th: celery seed, 7th: black chokeberry.[3]

Antioxidant bioavailability

[edit]

Polyphenols have antioxidant properties,[1][4]which is the modulatation of oxidative stress;[5] are antioxidant systems with possible application as redox medicine.[6]

Main article: Bioavailability

Almost all phenols and many plant polyphenols in vitro are antioxidants. In the case of flavonoids, apparent antioxidant effects are reported in vivo in foods such as blackcurrant, cocoa, dark chocolate, dealcoholized wine, garlic extract, grape juice, green tea, soy - these effects though aren't necessarily attributable to the action of flavonoids.[7]

First-pass metabolism

[edit]

The potential for an antioxidant function of most polyphenols is minimally[8] or never realized within the body[9] when administered orally [8] because of conjugation action on the active chemical constituent within first-pass metabolism.[9]

Xenobiotical

[edit]
Main article: xenobiotic metabolism

The in corpore response to polyphenols is xenobiotic.[8]

1

[edit]
(1,2-benzopyron / 2H-1-benzopyran-2-one)[10] Coumarins[11][12] are a benzopyrone type,[13] characterised by the presence of a benzo[α]pyrone (2H-benzopyran2-one) moiety[14]
types: furano, oligomeric, pyrano, sesquiterpenyl, simple, simple geranylated, simple prenylated.[15]
quantity in natural sources (most first):[b] tonka bean, [c] sweet clover, [d] chinese cinnamon [e]
(6-β-glucoside-7-hydroxycoumarin)[33] aesculin[11] syn. esculin[34] [f]
dried bark of: Fraxinus chinensis subsp. rhynchophylla Hance., Fraxinus chinensis Roxb., Fraxinus chinensis subsp. chinensis, Fraxinus stylosa Lingelsh[33][35]
[(3R,4S,5R,6S)-6-[8-chloro-4-hydroxy-3-[[4-hydroxy-3-(3-methylbut-2-enyl)benzoyl]amino]-2-oxochromen-7-yl]oxy-5-hydroxy-3-methoxy-2,2-dimethyloxan-4-yl] 5-methyl-1H-pyrrole-2-carboxylate [36] clorobiocin[37]
product of secondary metabolism in streptomycetes[38]
application as an antibiotic[36]
4,9-Bis[(3-methyl-2-buten-1-yl)oxy]-7H-furo[3,2-g][1]benzopyran-7-one[39] cnidicin[40]
Angelica koreana[40] Ostericum grosseserratum[39]
[(3R,4S,5R,6R)-5-hydroxy-6-[4-hydroxy-3-[[5-[[4-hydroxy-7-[(2R,3R,4S,5R)-3-hydroxy-5-methoxy-6,6-dimethyl-4-(5-methyl-1H-pyrrole-2-carbonyl)oxyoxan-2-yl]oxy-8-methyl-2-oxochromen-3-yl]carbamoyl]-4-methyl-1H-pyrrole-3-carbonyl]amino]-8-methyl-2-oxochromen-7-yl]oxy-3-methoxy-2,2-dimethyloxan-4-yl] 5-methyl-1H-pyrrole-2-carboxylate[41] coumermycin A1[42]
application as an antibiotic[36]
(3,3’-methylenebis(4-hydroxycoumarin) dicoumarol[43]
Melilotus officinalis (L.) Pall.: Link 1940)[43]
(7, 8-dihydroxy-6-methoxycoumarin) fraxetin[44]
Aesculus turbinata, Salsola laricifolia[45]
(8-hydroxy-6,7-dimethoxycoumarin) fraxidin[44]
Artemisia minor, Salsola laricifolia[46]
(7-hydroxy-6-methoxycoumarin 8-glucoside) fraxin[44]
Aesculus turbinata, Solanum tuberosum[47]
(6-hydroxy-5, 7-dimethoxycoumarin) fraxinol[44]
Elsholtzia bodinieri, Prunus prostrata[48]
(furan ring attached to carbon 6&7 (linear type) / 7&8 (angular type) of a benzo-α-pyrone (coumarin))[49] furanocoumarins[50]
7H-Furo[3,2-g][1]benzopyran-7-one[51] psoralen[11]
Ficus salicifolia, Psoralea corylifolia[51]
(7H-Furo[3,2-g][1]benzopyran-7-one, 9-(2,3-dihydroxy-3-methylbutoxy)-4-methoxy-)[52] byakangelicin[50]
Angelica dahurica[53]
(7H-Furo[3,2-g][1]benzopyran-7-one, 9-[(3-methyl-2-butenyl)oxy]-)[54] imperatorin[50]
Aegle marmelos (bael fruit), seeds of Pastinaca sativa (parsnip)[54]
(7H-Furo(3,2-g)(1)benzopyran-7-one, 4-((3-methyl-2-butenyl)oxy)-)[55] isoimperatorin[50]
Angelica dahurica, A. gigas, A. koreana, Glehniae root, Poncirus trifoliate Raf, Salvia miltiorrhiza[55]
4-{[(2S)-3,3-dimethyloxiran-2-yl]methoxy}-7H-furo[3,2-g][1]benzopyran-7-one[56] oxypeucedanin[50]
Citrus reticulata, Ferula syreitschikowii[56]
4-Methoxy-9-((3-methyl-2-buten-1-yl)oxy)-7H-furo(3,2-g)(1)benzopyran-7-one[57] phellopterin[50]
(7-hydroxy-6,8-dimethoxy coumarin)[44] isofraxidin[58]
Fraxinus exelsior (Spath & Jerzmanowska 1937)[44] Eleutherococcisenticosi (Rupr. et Maxim.) Maxim. rhizoma [g][58]
N-(7-((3-O-(aminocarbonyl)-6-deoxy-5-C-methyl-4-O-methyl-beta-L-lyxo-hexopyranosyl)oxy)-4-hydroxy-8-methyl-2-oxo-2H-1-benzopyran-3-yl)-4-hydroxy-3-(3-methyl-2-butenyl)-[59] novobiocin[37]
antibacterial[59] product from secondary metabolism in streptomycetes[38] Streptomyces niveus[59]
2H-1-Benzopyran-2-one, 6-(3-hydroxy-3-methyl-1-butenyl)-7-methoxy-, (E)-[60] suberenol[61]
Citrus reticulata, Zanthoxylum ovalifolium[60]
2H-1-Benzopyran-2-one, 7-methoxy-6-(3-methyl-2-butenyl)-[62] suberosin[61]
Semenovia dasycarpa, Zanthoxylum ovalifolium[62]
2H-1-Benzopyran-2-one, 7-hydroxy-[63] umbelliferone[11][64]
Caragana frutex, Hydrangea serrata[63]
2H-1-Benzopyran-2-one, 7-hydroxy-4-methyl-[65] 4-methylumbelliferone[66]
Ferula fukanensis, Tripterygium wilfordii[65]
6,7-Dihydroxy-2H-1-benzopyran-2-one esculetin[67][64]
Caragana frutex, Sonchus fruticosus[67]
(6,7-Dimethoxycoumarin) scoparone[68]
Cedrelopsis grevei, Saussurea eopygmaea[69]
(7-hydroxy-6-methoxycoumarin) scopoletin[70][64]
Caragana frutex, Phyllanthus sellowianus[71]
(7-methoxycoumarin) herniarin[10][64] / Methylumbelliferone[72]
Trichogonia grazielae, Yponomeuta mahalebellus[72]
(7-hydroxycoumarin glucoside) skimmin[10][64]
Artemisia ordosica, Daphne feddei, Edgeworthia chrysantha, Skimmia reevesiana[73]

2

[edit]
Curcuminoid
curcuma longa rhizome [74] [h]
bisdemethoxycurcumin
C. amada Roxb.[76] [77] C. kwangsiensis [78][79] (syn. C. chuanyujin C.K.Hsieh & Hao Zhang), [80] C. longa [81] C. zanthorrhiza [78]
curcumin [74]
[i]
demethoxycurcumin [74]
C. amada [76]

3

[edit]
Flavonoid: [83][2][84]
2-phenylchromans [85][86]
Anthocyanins[87]
noncomprehensive known most quantity: 750mg / 100 g−1: aubergine [87]
Apigeninidin [88] (traditional name) syn. apigenidin: corn [89]
Cyanidin [90]
noncomprehensive known most quantity: berries, especially within blueberries: 558.3 mg/100 g [91][87]
3,5-O-diglucoside [90]
3-O-
[2-O-(6-O-E-caffeoyl-β-D-glucopyanosyl)]-{6-O-[4-O-(6-O-E-3,5-dihydroxycinnamoyl-β-D-glucopyranosyl)-E-caffeoyl]-β-D-glucopyranosyl}-5-O-β-D-glucopyranoside [92]
(2-O-(6-O-(E)-caffeoyl-D glucoside)-D-glucoside)-5-O-D-glucoside [90]
[2-O-(6-O-E-coumaroyl-β-D-glucopyanosyl)]-{6-O-[4-O-(6-O-E-coumaroyl-β-D-glucopyranosyl)-E-caffeoyl]-β-D-glucopyranosyl}-5-O-β-D-glucopyranoside [93]
(3,6-O-dimalonyl-glucoside) [90]
(6-acetyl-galactoside) [90]
(6-acetyl-glucoside) [90]
(6-caffeoyl-glucoside) [90]
(6-dioxalyl-glucoside) [90]
(6-malonyl-3-glucosyl-glucoside) [90]
(6-malonyl-glucoside) [90]
(6-p-coumaroyl-glucoside) [90]
(6-succinyl-glucoside) [90]
arabinoside [90]
diglucoside-5-O-glucoside [90]
galactoside [90]
glucoside [90]
glucosyl-rutinoside [90]
rutinoside [90]
sambubioside [90]
sambubioside 5-O-glucoside [90]
sophoroside [90]
xyloside [90]
xylosyl-rutinoside [90]
4'-O-Methylcyanidin 3-O-D-glucoside [90]
delphinidin [94]
3,3',5'-triglucoside [95]
(ternatins [j]) C. ternatea [96]
3,5-O-diglucoside [90]
3-O-
(6-acetyl-galactoside) [90]
(6-acetyl-glucoside) [90]
(6-p-coumaroyl-glucoside) [90]
arabinoside [90]
feruloyl-glucoside [90]
galactoside [90]
glucoside [90]
glucosyl-glucoside [90]
rutinoside [90]
sambubioside [90]
xyloside [90]
4-O-Methyldelphinidin 3-O-D-glucoside [90]
4'-O-Methyldelphinidin 3-O-rutinoside [90]
Isopeonidin
3-O-
arabinoside [90]
galactoside [90]
glucoside [90]
rutinoside [90]
sambubioside [90]
xyloside [90]
malvidin [94]
3,5-O-diglucoside [90]
3-O-
(6-acetyl-galactoside) [90]
(6-acetyl-glucoside) [90]
(6-caffeoyl-glucoside) [90]
(6-p-coumaroyl-glucoside) [90]
rabinoside [90]
galactoside [90]
glucoside [90]
pelargonidin [94]
3,5-O-diglucoside [90]
3-O-
(6-malonyl-glucoside) [90]
(6-succinyl-glucoside) [90]
arabinoside [90]
galactoside [90]
glucoside [90]
glucosyl-rutinoside [90]
rutinoside [90]
sambubioside [90]
sophoroside [90]
Peonidin [90]
3,5-O-diglucoside [90]
3-O-
(2-O-(6-O-(E)-caffeoyl-D-glucosyl)-D-glucoside)-5-O-D-glucoside [90]
(6-acetyl-galactoside) [90]
(6-acetyl-glucoside) [90]
(6-p-coumaroyl-glucoside) [90]
arabinoside [90]
diglucoside-5-O-glucoside [90]
galactoside [90]
glucoside [90]
rutinoside [90]
sambubioside [90]
sambubioside-5-O-glucoside [90]
sophoroside [90]
xyloside [90]
Petunidin
3-O-
(6-acetyl-galactoside) [90]
(6-acetyl-glucoside) [90]
(6-p-coumaroyl-glucoside) [90]
arabinoside [90]
galactoside [90]
glucoside [90]
rhamnoside [90]
rutinoside [90]
Pigment A [90]
Pinotin A [90]
Vitisin A [90]
Aurones [97][98]
leptosidin [99]
maritimetin [99]
sulfuretin [99]
Chalcones [100]
Natural [100][101]
2′,4′-dihydroxychalcone [100]
Oxytropis chiliophylla Benth. [102][103][104] O. falcata Bunge [105]
2′,6′-dihydroxy-4′-methoxychalcone [100]
2′-hydroxy-2,4,4′,6′-tetramethoxychalcone [100]
2′-hydroxy-2,3,4,4′,6′-pentamethoxychalcone [100]
3,2′-dihydroxy-2,4,4′,6′-tetramethoxychalcone [100]
3,4,2′,4′-tetrahydroxychalcone 4′-O-β-D-glucopyranoside [100]
4-hydroxychalcone [100]
4′-hydroxychalcone [100]
4-methoxychalcone [101]
arbutin [101]
Butein [100]
Calomelanone [100]
chalconaringenin [101]
Dihydrochalcone diglycoside [100]
Dimethyl-cardamonin [100]
Echinantin [100]
Flavokawain B [100]
Flavokawain C [100]
Lophirones B [100]
Lophirones C [100]
Homobutein [100]
Isoliquiritigenin [100]
Isosalipurposide [100]
Kamalachalcone E [100]
Licochalcone A [100]
Licochalcone B [100]
Licochalcone C [100]
Licochalcone D [100]
Licochalcone G [100]
Lonchocarpin [100]
Mallotophilippens C [100]
Mallotophilippens D [100]
Mallotophilippens E [100]
Naringenin chalcone [100]
phlioridzin [101]
phloretin [101]
Rottlerin [100]
Xanthoangelol [100]
Angelica keiskei [106]
((E)-1-[2,4-dihydroxy-3-[(2E)-6-hydroxy-3,7-dimethylocta-2,7-dienyl]phenyl]-3-(4-hydroxyphenyl)prop-2-en-1-one [107]) Xanthoangelols B [100]
Xanthoangelols D [100]
Xanthoangelols E [100]
Xanthoangelols F [100]
Xanthoangelols G [100]
Xanthodeistal [100]
Synthetic [100]
1,1-bis-[(3′,4′-N-(urenylphenyl)-3-(3″,4″,5″-trimethoxyphenyl)]-2-propen-1-one (dimeric derivative group) [100]
1-(2,3,4-trimethoxyphenyl)-3-(3-(2-chloroquinolinyl)-2-propen-1-one [100]
1-(2-benzyloxy-6-hydroxyphenyl)-3-(5-bromo-2-methoxyphenyl)-propenone (O-benzyl-substituted group) [100]
1-(4-benzimidazol-1-yl-phenyl)-3-(2, 4-dimethoxy-phenyl)-propen-1-one [100]
1-(4-hydroxyphenyl)-3-(4-methoxyphenyl)propan-1-one [100]
2,2′-hydroxychalcone [100]
2,3,4-trimethoxy-2′-hydroxychalcone [100]
2′,3′,4′-trihydroxychalcone [100]
2′,4-dihydroxy-6′-isopentyloxychalcone [100]
2′,4′-dihydroxy-6-methoxy-3,5-dimethylchalcone [100]
2′,5′-dihydroxy-2-furfurylchalcone [100]
2′,5′-dihydroxy2-naphthylchalcone [100]
2-chloro-4′,6′-dimethoxy-2′-hydroxychalcone [100]
(2E)-1-(2,5-dimethoxy-phenyl)-3-(1-naphthyl)-2-propene-1-one [100]
(2E)-3-(2-naphthyl)-1-(3′-methoxy-4′-hydroxy-phenyl)-2-propen-1-one [100]
2-hydroxy-3′,5,5′-trimethoxychalcone (DK-139) [100]
2′-hydroxy-4-methoxychalcone (AN07) [100]
3-(2,5-dimethoxyphenyl)-1-(5-methylfuran-2-yl)prop-2-en-1-one (DMPF-1) [100]
3,5-bis(4-methylphenyl)-1-(phenylsulfonyl)-4,5-dihydro-1H-pyrazole [100]
3′-bromo-3,4-dimethoxychalcone [100]
3-phenyl-1-(2,4,6- tris(methoxymethoxy)phenyl)prop-2-yn-1-one [100]
4,2′,4′-trihydroxychalcone [100]
(4-(3-(2-fluorophenyl)acryloyl)phenyl)amino)-2-oxoethyl)-N,N-dimethyloctan-1-aminium chloride) [100]
4,5-dihydro-1-phenyl-3,5-dip-tolyl-1H-pyrazole [100]
4,5-dihydro-3,5-dip-tolylpyrazole-1-carbothioamide [100]
4,5-dihydro-3,5-dip-tolylpyrazole-1-carboxamide [100]
(4,5-dihydro-3,5-dip-tolylpyrazol-1-yl)(phenyl)methanone [100]
chalcone-1,2,3-triazole hybrids [108]
Chalcone 195 (synthetic) [100]
(Chalcone-phenylpyran-2-one derivatives bearing a N,N-dimethyl ethylamine side chain) Chalcone 47 [100]
Chalcone acetamides [109]
chalcone sulphonamides [100]
Chromanochalcones [100]
chromenochalcones [100]
chromeno-dehydrochalcones [100]
(E)-1-;[B2-hydroxy-4-methoxy-3-(morpholinomethyl)phenyl];-3-(pyridin-2-yl)prop-2-en-1-one (heterocyclic) [100]
(E)-1-(2-hydroxyphenyl)-3-(4-methyl-phenyl)-prop-2-en-1-one [100]
(E)-1,3-dip-tolylprop-2-en-1-one [100]
(E)-1-(4-aminophenyl)-3-(2,3-dimethoxyphenyl)-prop-2-en-1-one [100]
(E)-1-(4-aminophenyl)-3-(phenylprop-2-en-1-one) [100]
(E)-1-[4-ethoxy-2-hydroxy-5-(morpholinomethyl)phenyl]-3-(pyridin-2-yl)prop-2-en-1-one) (Heterocyclic) [100]
(E)-1-(4-hydroxyphenyl)-3-(4-methoxyphenyl)prop-2-en-1-one [100]
(E)-1-(4-hydroxyphenyl)-3-phenylprop-2-en-1-one [100]
(E)-2-(3′,4′-dimethoxy-benzylidene)-1-tetralone [100]
(E)-2-(4′-methoxybenzylidene)-1-benzosuberone [100]
(E)-2,6-difluoro-4′-methoxychalcone (L6H9) [100]
(E)-3-(4-methoxyphenyl)-2-methyl-1-(3,4,5-trimethoxyphenyl)prop-2-en-1-one [100]
(E)-N-(2-((4-(3-(2-fluorophenyl)acryloyl)phenyl)amino)-2-oxoethyl)-N,N-dimethyloctan-1-aminium chloride (cationic) [100]
(E)-N-(2-((4-cinnamoylphenyl)amino)-2-oxoethyl)-N,N-dimethyloctan-1-aminium chloride (cationic) [100]
licochalcones [100]
morachalcones [100]
prenylated chalcones [100]
Quinolinone-chalcone derivatives [100]
quinolinyl chalcones [100]
quinoxaline chalcones [100]
Dihydrochalcones [110]
2′,4′-dihydroxydihydrochalcone-4-O-β-D-glucopyranoside [111]
3-hydroxyphloretin [111]
3-hydroxyphlorizin [111]
3′-O-β-d-glucopyranosyl [111]
α,β-dihydroxantohumol [111]
aspalathin [111]
balsacone A [111]
balsacone B [111]
balsacone C [111]
dihydroisorcordoin [111]
elastichalcone C [111]
evelynin A [111]
evelynin B [111]
hesperetin-7-O-glucoside [111]
hesperetin dihydrochalcone-7-O-glucoside [111]
isopanduratin [111]
naringin dihydrochalcone [111]
neohesperidin dihydrochalcone [111]
nothofagin [111]
panduratin [111]
phloretin [111]
phloretin 2′-xyloglucosid [111]
phlorizin [111]
prunin [111]
sakenin F [111]
sakenin H [111]
sieboldin [111]
trilobatin [111]
zornioside [111]
Dihydroflavonols [110]
dihydrokaempferol [112]
dihydromyricetin [112]
dihydroquercetin [112]
Flavanols[94]
apple, tea[94]
Flavan-3,4-ols [113]
Flavan-3-ols [113]
afzelechin [113]
(+)-afzelechin [114]
Zizyphus jujuba Mill. var. spinosa root [114]
(−)-afzelechin[114]
Astilbe rivularis rhizome [114]
afzelechin-5-O-β-d-glucopyranoside [113]
afzelechin-7-O-β-d-glucopyranoside [113]
catechin: [94]
tea leaves, beans, black grapes, cherries, cacao [115]
3′- deoxycatechin-3-O-α-l-rhamnopyranoside [113]
3′-O-methylcatechin-5-O-β-d-glucopyranoside [113]
4′-O-methylcatechin 5-O-β-d-glucopyranoside [113]
catechin-5-O-β-d-glucoside [113]
epicatechin [94][116]
epigallocatechin [94][116]
epigallocatechin gallate / [77] epigallocatechin-3-gallate[116]
green tea [116]
gallocatechin[113]
fisetinidol [113]
glausan-3 [94]
proanthocyanidins [94][117]
(type: depending on the STEREOCHEMICAL CONFIGURATION and linkage between monomers) [118][119]
A-type [120]
B-type [120]
Procyanidin B2 [121][122]
(constituently most of foods sampled) cocoa powder, chocolate, Vicia faba,[123] (most of of compounds within) Tamarindus indica L. (516.95 ± 4.64 μg/g)[121]
robinetinidol [113]
Flavan-4-ols [113]
Flavanones [87]
orange juice, grapefruit juice, lemon juice [87]
eriodictyol [124]
hesperidin [94]
liquiritigenin [124]
naringenin [94]
naringin [94]
pinocembrin [124]
taxifolin [94]
Flavones [87]
parsley, celery [87]
(4,’5,7-trihydroxyflavone)[125] apigenin [94]
most quantity in selected foods sampled: dried Petroselinum crispum [125][126][127] most quantity in dried forms [126][128] mean 215.46 (maximum 630) mg/100 (confidence level (CL): 74-50 CL range is 0-100=least-most) [127]
(apigenin 6-C-glucoside) isovitexin [129]
(5, 7, 4-trihydroxyflavone-8-glucoside / apigenin 8-C-glucoside) vitexin [129]
chrysin [94]
glucosidestangeretin [94]
luteolin [94]
rutin [94]
Flavonols [87]
yellow onion, curly kale, leek, cherry tomato, brocolli, blueberry [87]
Monomeric flavanols[87]
chocolate, beans, apricot [87]
isorhamnetin [130]
kaempferol [94]
myricetin [94]
quercetin [94]
tamarixetin [94]
3-phenylchromans [85][86]
Isoflavonoids [85][101]
isoflavans [85]
Isoflavan-4-ols [113]
isoflavones [85]
Isoflavones [87]
soy flour, boiled soybeans, miso, tofu, tempeh, soy milk [87]
daidzein [94]
genistein [94]
pterocarpans [85][98]
4-phenylchromen [101] / 4-phenylcoumarin [131]
Neoflavonoids [101][131]
4-arylchromanes [131]
4-arylcoumarins (neoflavones) [131]
dalbergiones [131]
dalbergiquinols [131]

4

[edit]
Lignans [132][2][84]
lariciresinol [132]
matairesinol [132]
pinoresinol [132]
secoisolariciresinol diglucoside [132]

5

[edit]
Phenolic acids:[132][2][84]
hydroxybenzoic acids[87]
blackberry, black currant, raspberry [87]
2,3-Dihydroxybenzoic acid [133]
2,4-Dihydroxybenzoic acid [133]
2,6-Dihydroxybenzoic acid [133]
2-Hydroxybenzoic acid [133] (salicylic acid) [134]
first, second, third most [k] (333 foods sampled): paprika hot powder 203 mg/1OOg, thyme leaves dried: 183 mg, turmeric: 76.4 [135]
2-Hydroxyhippuric acid [133]
3,4-dihydroxybenzoic acid (protocatechuic acid) [136][137]
3,4-O-Dimethylgallic acid [133]
3,5-Dihydroxybenzoic acid [133]
3-Hydroxybenzoic acid [133]
3-Hydroxyhippuric acid [133]
3-O-Methylgallic acid [133]
4-Hydroxybenzoic acid [133]
4-Hydroxybenzoic acid 4-O-glucoside [133]
4-Hydroxyhippuric acid [133]
4-O-Methylgallic acid [133]
5-O-Galloylquinic acid [133]
gallic acid[138][139]
crocus sativus L.[138]
Ellagic acid glucoside [133]
Ellagic acid [133]
Ellagic acid acetyl-arabinoside [133]
Ellagic acid acetyl-xyloside [133]
Ellagic acid arabinoside [133]
Gallic acid 3-O-gallate [133]
Gallic acid 4-O-glucoside [133]
Gallic acid ethyl ester [133]
Gallagic acid [133]
Galloyl glucose [133]
Gentisic acid [133]
Hippuric acid [133]
Lambertianin C [133]
Paeoniflorin [133]
Protocatechuic acid 4-O-glucoside [133]
Punicalagin [133]
Punicalin [133]
Sanguiin H-6 [133]
Syringic acid [133]
Valoneic acid dilactone [133]
Vanillic acid [133]
Vanillic acid 4-sulfate [133]
hydroxycinnamic acids[87]
blueberry, kiwi, cherry, plum[87]
1,2,2'-Triferuloylgentiobiose [140]
1,2,2'-Trisinapoylgentiobiose [140]
1,2-Diferuloylgentiobiose [140]
1,2'-Disinapoyl-2-feruloylgentiobiose [140]
1,2-Disinapoylgentiobiose [140]
1,5-Dicaffeoylquinic acid [140]
1,5-Diferuloylquinic acid [140]
1-Caffeoyl-5-feruloylquinic acid [140]
1-Feruloyl-5-caffeoylquinic acid [140]
1-Sinapoyl-2,2'-diferuloylgentiobiose [140]
1-Sinapoyl-2-feruloylgentiobiose [140]
2,5-di-S-Glutathionyl caftaric acid [140]
2-S-Glutathionyl caftaric acid [140]
3,4-Dicaffeoylquinic acid [140]
3,4-Diferuloylquinic acid [140]
3,5-Dicaffeoylquinic acid [140]
3,5-Diferuloylquinic acid [140]
3-Caffeoylquinic acid [140]
3-Feruloylquinic acid [140]
3-O-Methylrosmarinic acid [140]
3-p-Coumaroylquinic acid [140]
3-Sinapoylquinic acid [140]
4,5-Dicaffeoylquinic acid [140]
4-Caffeoylquinic acid [140]
4-Feruloylquinic acid [140]
4-p-Coumaroylquinic acid [140]
4-Sinapoylquinic acid [140]
5-5'-Dehydrodiferulic acid [140]
5-8'-Benzofuran dehydrodiferulic acid [140]
5-8'-Dehydrodiferulic acid [140]
5-Caffeoylquinic acid [140]
5-Feruloylquinic acid [140]
5-p-Coumaroylquinic acid [140]
5-Sinapoylquinic acid [140]
8-O-4'-Dehydrodiferulic acid [140]
24-Methylcholestanol ferulate [140]
24-Methylcholesterol ferulate [140]
24-Methylenecholestanol ferulate [140]
24-Methyllathosterol ferulate [140]
Avenanthramide 2c [140]
Avenanthramide 2f [140]
Avenanthramide 2p [140]
Avenanthramide K [140]
caffeic acid [141]
Caffeic acid 4-sulfate [140]
Caffeic acid 3-sulfate [140]
Caffeic acid ethyl ester [140]
Caffeic acid 3-O-glucuronide [140]
Caffeic acid 4-O-glucuronide [140]
Caffeic acid 4-O-glucoside [140]
Caffeoyl aspartic acid [140]
Caffeoyl C1-glucuronide [140]
Caffeoyl glucose [140]
Caffeoyl tartaric acid [140]
Chicoric acid [140]
chlorogenic acid; [142] isomers of: cryptochlorogenic acid, cynarin, isochlorogenic acid A, isochlorogenic acid B, isochlorogenic acid C [132]
Cinnamic acid [140]
Cinnamoyl glucose [140]
ferulic acid [132]
Ferulic acid 4-O-glucuronide [140]
Ferulic acid 4-O-glucoside [140]
Ferulic acid 4-sulfate [140]
Feruloyl C1-glucuronide [140]
Feruloyl glucose [140]
Feruloyl tartaric acid [140]
Feruloylglycine [140]
Hydroxycaffeic acid [140]
Isoferulic acid [140]
Isoferulic acid 3-O-glucuronide [140]
Isoferulic acid 3-sulfate [140]
Isoferuloyl C1-glucuronide [140]
m-Coumaric acid [140]
o-Coumaric acid [140]
p-Coumaric acid [140]
p-Coumaric acid 4-O-glucoside [140]
p-Coumaric acid ethyl ester [140]
p-Coumaroyl glycolic acid [140]
p-Coumaroyl glucose [140]
p-Coumaroyl malic acid [140]
p-Coumaroyl tartaric acid [140]
p-Coumaroyl tartaric acid glucosidic ester [140]
p-Coumaroyl tyrosine [140]
p-Coumaroylquinic acid [140]
Rosmarinic acid [140]
Schottenol ferulate [140]
Sinapic acid [140]
Sinapine [140]
Sitosterol ferulate [140]
Stigmastanol ferulate [140]
Verbascoside [140]
Hydroxyphenylacetic acids [143]
2-Hydroxy-2-phenylacetic acid [144]
2-Hydroxyphenylacetic acid [144]
3,4-Dihydroxyphenylacetic acid [144]
3-Hydroxyphenylacetic acid [144]
4-Hydroxymandelic acid [144]
4-Hydroxyphenylacetic acid [144]
Homovanillic acid [144]
Homovanillic acid 4-sulfate [144]
Homoveratric acid [144]
Methoxyphenylacetic acid [144]
Phenacetylglycine [144]
Phenylacetic acid [144]
Hydroxyphenylpentanoic acids [143]
3-Hydroxyphenylvaleric acid [145]
4-Hydroxy-(3',4'-dihydroxyphenyl)valeric acid [145]
5-(3',4',5'-trihydroxyphenyl)-γ-valerolactone [145]
5-(3',4',-dihydroxyphenyl)-γ-valerolactone [145]
5-(3',4'-dihydroxyphenyl)-valeric acid [145]
5-(3',5'-dihydroxyphenyl)-γ-valerolactone [145]
5-(3',5'-dihydroxyphenyl)-γ-valerolactone 3-O-glucuronide [145]
5-(3'-Methoxy-4'-hydroxyphenyl)-γ-valerolactone [145]
Hydroxyphenylpropanoic acids [143]
3-(3,4-Dihydroxyphenyl)-2-methoxypropionic acid [146]
3,4-Dihydroxyphenyllactic acid methyl ester [146]
3-Hydroxy-3-(3-hydroxyphenyl)propionic acid [146]
3-Hydroxy-4-methoxyphenyllactic acid [146]
3-Hydroxyphenylpropionic acid [146]
3-Methoxy-4-hydroxyphenyllactic acid [146]
3-Phenylpropionic acid [146]
4-Hydroxyphenyl-2-propionic acid [146]
Danshensu [146]
Dihydrocaffeic acid [146]
Dihydro-p-coumaric acid [146]
Dihydrocaffeic acid 3-O-glucuronide [146]
Dihydrocaffeic acid 3-sulfate [146]
Dihydroferulic acid [146]
Dihydroferulic acid 4-O-glucuronide [146]
Dihydroferulic acid 4-sulfate [146]
Dihydroferuloylglycine [146]
Dihydrosinapic acid [146]
Hydroxydanshensu [146]

6

[edit]
Phenylethanoid glucosides [147]
verbascoside: olive [148]

7

[edit]
Polyphenolic Amides [149][150]
anthranilic acid amides (avenanthramides) Avena sativa [151]

8

[edit]
Secoiridoid [148] [l]
oleacein virgin olive oil [153]
oleocanthal virgin olive oil [153]
oleuropein: olive [154][148] most (1st) 1840.29 ± 49.27 mg/kg: Sigoise (Algerian), 2nd: 1459.5 ± 100.1 Throuba Thassos (Greek), 3rd: 1411.0 ± 452.7 Manzanilla (Spanish), 4th: 553.4 ± 133 Ascolana tenera (Italian)[155]
3,4-dihydroxyphenylethanol-elenolic acid extra virgin olive oil [156][157]

9

[edit]
Stilbenes [132][2][84]
pallidol [158]
resveratrol:[132] japanese knotweed [158]
trans-delta-viniferin [158]
trans-piceatannol [158]

10

[edit]
Tannins [84]
condensed tannins [159] =catechin tannins=proanthocyanidins[160]
hydrolysable tannins [159][160]
ellagitannins[159]
gallotannins[159]

11

[edit]
Xanthones [161]
bis-xanthones [162]
prenylated xanthone [162]
simple xanthones [162]
xanthone glucosides / glycosylated xanthones [162]
mangiferin mangifera indica [77][163]
xanthonolignoids [162]

See also

[edit]

Notes

[edit]
  1. ^ Used extensively by companies which produce fragrances (non-exhaustative list excluding specific product identifier): BDK, Byredo, d’Orsy, Guerlain, Jo Malone, Le Labo, Victoria Beckham Beauty[17] The White Company[18] Liberty[19] Laboratory Perfumes (British founded 2012)[20] onekind (Motley Brands, Los Angeles)[21][22] Lush[23] Maison Francis Kurkdjian (founded 2009)[24] Shay & Blue (Dom De Vetta)[25][26] Hermetica [27] Rochas, Dior, Chanel, Elie Saab, Tom Ford, Carolina Herrera[28]
  2. ^ risk of exceeding the tolerable daily intake (1mg per 12.5 kg body weight per day,[16] [a] an alternative assessment states: 1mg per 10kg [29])
  3. ^ extract:[30]
    6 samples of Dipteryx odorata range: 20.0 - 44.3 mg / g
  4. ^
    leaf extract:
    7 samples of Melilotus albus [31]
    range fresh herb: 6.42 - 11.73 mg/g
    dried: 0.79 - 3.21
    3 sample of Melilotus officinalis[31]
    fresh: 6.32 - 9.84
    dried: 1.33 - 1.97
    flower extract:
    7 samples of M albus[31]
    fresh: 12.31 - 25.57
    dried: 5.26 - 9.84
    3 sample of M officinalis[31]
    fresh: 11.26 - 26.47
    dried: 5.83 - 8.38
  5. ^ Coumarin § Natural occurrence
    Ceylon cinnamon bark samples (0.08-0.15 mg g-1)[32]
    Cinnamomum cassia Blume, C. burmanni Blume, C. loureiroi Nees (1.38-5.80 mg g-1)[32]
  6. ^ traditional Chinese medicine: Cortex Fraxini[33] Fraxini cortex[35] the same referent / difference indistinguishable
  7. ^ not Panax; i.e. ginseng (of Siberia) is a misnomer[58]
  8. ^ DILIN investigated cases of liver damage "strongly linked to HLA-B*35:01" (10 cases in the US for 2004 and 2022: [75] rate of approximately 0.003000 cases per 100,000 people)
  9. ^ 3 mg per kg body weight per day acceptable daily intake (assessed as E100) [82]
  10. ^ polyacylated derivatives of delphinidin 3,3',5'-triglucoside [95]
  11. ^ "218" curry powder was excluded as does not necessarily have the same (a standardized formulation) ingredients
  12. ^ "protection of blood lipids from oxidative stress" EU regulations state require: "olive oil which contains at least 5 mg of hydroxytyrosol and its derivatives", "a daily intake of 20 g"[152]

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  152. ^ "COMMISSION REGULATION (EU) No 432/2012 establishing a list of permitted health claims made on foods, other than those referring to the reduction of disease risk and to children's development and health ANNEX LIST OF PERMITTED HEALTH CLAIMS". Official Journal of the European Union. Publications Office of the European Union. 16 May 2012 – via www.lecor.eu/2818174_lepur-2025-one-of-europe-s-most-powerful-high-polyphenol-olive-oils. Olive oil polyphenols contribute to the protection of blood lipids from oxidative stress: The claim may be used only for olive oil which contains at least 5 mg of hydroxytyrosol and its derivatives (e.g. oleuropein complex and tyrosol) per 20 g of olive oil. In order to bear the claim information shall be given to the consumer that the beneficial effect is obtained with a daily intake of 20 g of olive oil.
  153. ^ a b Ana Karković Marković; et al. (May 2019). "Hydroxytyrosol, Tyrosol and Derivatives and Their Potential Effects on Human Health - 1. Introduction". Molecules. 24 (10). MDPI. doi:10.3390/molecules24102001. PMC 6571782. PMID 31137753.
  154. ^ Barbara Barbaro; Gabriele Toietta; Roberta Maggio; Mario Arciello; Mirko Tarocchi; Andrea Galli; Clara Balsano (14 October 2014). "Effects of the Olive-Derived Polyphenol Oleuropein on Human Health - 2. Effects of Oleuropein on Human Health 2.1. Antioxidant Effect". Int J Mol Sci. 15 (10): 18508–18524. doi:10.3390/ijms151018508. PMC 4227229. PMID 25318054. Visioli et al. demonstrated in healthy volunteers that administration of oleuropein decreases, in a dose-dependent manner, the urinary excretion of 8-iso-PGF2α, indicating lower in vivo lipid peroxidation [34]. A scavenging effect of oleuropein was also demonstrated with respect to hypochlorous acid [30], a potent oxidant species produced in vivo by neutrophils myeloperoxidase at the site of inflammation [35].
  155. ^ Marta Gallardo-Fernández; et al. (6 August 2022). "Hydroxytyrosol in Foods: Analysis, Food Sources, EU Dietary Intake, and Potential Uses - 2. Methodology 2.1. Literature Search - Table 1". Foods. 11 (15). Universidad de Sevilla: MDPI. doi:10.3390/foods11152355. PMC 9368174. PMID 35954121.
  156. ^ Monica Bucciantini; et al. (29 June 2021). Rui F M Silva; Lea Pogačnik (eds.). "Olive Polyphenols: Antioxidant and Anti-Inflammatory Properties - 2. Olive Polyphenols: A Group of Molecules with Shared Chemical and Biological Properties: Structure, Abundance and Bioavailability". Antioxidants (Basel). 10 (7). University of Florence: MDPI. doi:10.3390/antiox10071044. PMC 8300823. PMID 34209636. The most abundant secoiridoid in olive oil is 3,4-dihydroxyphenylethanol-elenolic acid (3,4-DHPEA-EA), whose glucose-bound form is commonly known as oleuropein
  157. ^ Carlo Bisignano; Angela Filocamo; et al. (1 July 2014). "3,4-DHPEA-EA from Olea Europaea L. is effective against standard and clinical isolates of Staphylococcus sp". Ann Clin Microbiol Antimicrob. 13 (24) 24. University of Messina: BioMed Central Ltd. part of Springer Nature. doi:10.1186/1476-0711-13-24. ISSN 1476-0711. PMC 4107751. PMID 24986240. the antibacterial effect of 3,4-DHPEA-EA (methyl-4-(2-(3,4-dihydroxyphenethoxy)-2-oxoethyl)-3-formyl-2-methyl-3,4-dihydro-2H-pyran-5-carboxylate), a derivate of oleuropein
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  159. ^ a b c d Filomena Nazzaro; Francesca Coppola; Florinda Fratianni; Manar Abdalrazeq; Maria Neve Ombra; Beatrice De Giulio; Raffaele Coppola; Gokhan Zengin (2025). "Polyphenols Bioactive Metabolites, and Their Anti-Biofilm and Neuroprotective Potential: 2. Polyphenols: Chemical Classification and Dietary Sources - 2.1.5. Tannins". Foods. 14 (22). doi:10.3390/foods14223976. PMC 12651691. PMID 41300132. two main types: condensed and hydrolysable - Hydrolysable tannins are made when gallic or ellagic acid joins to sugar, forming gallotannins and ellagitannins
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