886:
899:
885:
701:
493:
898:
390:
256:
462:
356:
235:
428:
3388:
586:
649:
526:
3402:
556:
619:
40:
1953:
1866:"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 1924/20061 following a request in accordance with Article 19 of Regulation (EC) No 1924/2006"
247:
The flavonoids are products from a cinnamoyl-CoA starter unit, with chain extension using three molecules of malonyl-CoA. Reactions are catalyzed by a type III PKS enzyme. These enzyme do not use ACPSs, but instead employ coenzyme A esters and have a single active site to perform the necessary series
891:
Schematic representation of the flavan-3-ol (â)-epicatechin metabolism in humans as a function of time post-oral intake. SREM: structurally related (â)-epicatechin metabolites. 5C-RFM: 5-carbon ring fission metabolites. 3/1C-RFM: 3- and 1-carbon-side chain ring fission metabolites. The structures of
869:
containing 200 mg of flavanols, stating that such intake "may contribute to maintenance of vascular elasticity and normal blood flow". As of 2022, food-based evidence indicates that intake of 400â600 mg per day of flavan-3-ols could have a small positive effect on cardiovascular
248:
of reactions, e.g. chain extension, condensation, and cyclization. Chain extension of 4-hydroxycinnamoyl-CoA with three molecules of malonyl-CoA gives initially a polyketide (Figure 1), which can be folded. These allow
Claisen-like reactions to occur, generating aromatic rings.
137:
was imprecisely applied to include the flavanols, which are distinguished by absence of ketone(s). Catechin monomers, dimers, and trimers (oligomers) are colorless. Higher order polymers, anthocyanidins, exhibit deepening reds and become
1675:
904:
Flavan-3-ol precursors of the microbial metabolite 5-(3â˛/4â˛-dihydroxyphenyl)-Îł-valerolactone (gVL). Only compounds with intact (epi)catechin moiety result in the formation of ÎłVL by the intestinal microbiome. ECG,
1236:
Payne MJ, Hurst WJ, Miller KB, Rank C, Stuart DA (October 2010). "Impact of fermentation, drying, roasting, and Dutch processing on epicatechin and catechin content of cacao beans and cocoa ingredients".
780:
configuration. While monomeric flavan-3-ols are readily taken up, oligomeric forms are not absorbed. Most data for human metabolism of flavan-3-ols are available for monomeric compounds, especially
1392:"Assessing the respective contributions of dietary flavanol monomers and procyanidins in mediating cardiovascular effects in humans: randomized, controlled, double-masked intervention trial"
3301:
1559:"The metabolome of [2-C](â)-epicatechin in humans: implications for the assessment of efficacy, safety, and mechanisms of action of polyphenolic bioactives"
3232:
102:
The single-molecule (monomer) catechin, or isomer epicatechin (see diagram), adds four hydroxyls to flavan-3-ol, making building blocks for concatenated polymers (
804:
has also an important role in the metabolism of flavan-3-ols and they are catabolized to smaller compounds such as 5-(3â˛/4â˛-dihydroxyphenyl)-Îł-valerolactones and
1897:
Crowe-White, Kristi M; Evans, Levi W; Kuhnle, Gunter G C; Milenkovic, Dragan; Stote, Kim; Wallace, Taylor; Handu, Deepa; Senkus, Katelyn E (3 October 2022).
3269:
1796:"Dietary intakes of flavan-3-ols and cardiometabolic health: systematic review and meta-analysis of randomized trials and prospective cohort studies"
3244:
249:
3249:
808:. Only flavan-3-ols with an intact (epi)catechin moiety can be metabolized into 5-(3â˛/4â˛-dihydroxyphenyl)-Îł-valerolactones (image in Gallery).
1676:"Summary Safety Review - Green tea extract-containing natural health products - Assessing the potential risk of liver injury (hepatotoxicity)"
3274:
3264:
1281:
1069:
1985:
1441:"Intestinal absorption, metabolism, and excretion of (â)-epicatechin in healthy humans assessed by using an intestinal perfusion technique"
266::Schematic overview of the flavan-3-ol (â)-epicatechin biosynthesis in plants: Enzymes are indicated in blue, abbreviated as follows: E1,
2695:
2778:
492:
3370:
2503:
1343:"Dietary (poly)phenolics in human health: structures, bioavailability, and evidence of protective effects against chronic diseases"
1013:"Dietary (poly)phenolics in human health: structures, bioavailability, and evidence of protective effects against chronic diseases"
3365:
3259:
3210:
3291:
3128:
3337:
2422:
303:
1843:
1480:
Kuhnle G, Spencer JP, Schroeter H, Shenoy B, Debnam ES, Srai SK, et al. (October 2000). "Epicatechin and catechin are
2655:
3021:
283:
3296:
2685:
2601:
757:
299:
267:
1619:"Evaluation at scale of microbiome-derived metabolites as biomarker of flavan-3-ol intake in epidemiological studies"
291:
3238:
700:
3254:
3342:
3279:
2640:
2635:
1136:"Two-photon excitation with pico-second fluorescence lifetime imaging to detect nuclear association of flavanols"
2660:
3123:
2724:
1978:
910:
498:
461:
209:
79:
1957:
1519:
Das NP (December 1971). "Studies on flavonoid metabolism. Absorption and metabolism of (+)-catechin in man".
295:
255:
3441:
2771:
2630:
2310:
892:
the most abundant (â)-epicatechin metabolites present in the systemic circulation and in urine are depicted.
389:
307:
279:
275:
936:
Ullah C, Unsicker SB, Fellenberg C, Constabel CP, Schmidt A, Gershenzon J, Hammerbacher A (December 2017).
3306:
2650:
2645:
2496:
2472:
2432:
2427:
271:
2676:
2673:
2669:
2665:
3043:
2729:
427:
66:-chromen-3-ol skeleton. Flavan-3-ols are structurally diverse and include a range of compounds, such as
1087:"Flavonoid biosynthesis. A colorful model for genetics, biochemistry, cell biology, and biotechnology"
3446:
3406:
3357:
3347:
3103:
2965:
2955:
2597:
2287:
1630:
1570:
1390:
RodrĂguez Mateos A, Weber T, Skene SS, Ottaviani JI, Crozier A, Kelm M, et al. (December 2018).
117:
occur for each of them. They are distinguished from the yellow, ketone-containing flavonoids such as
3451:
3322:
3169:
3068:
2885:
2624:
2618:
2540:
2131:
1971:
858:
691:
585:
467:
238:
Structures (Epi)catechin, (epi)catechin-gallate, (epi)gallocatechin and (epi)gallocatechin-gallate.
71:
2691:
3436:
3431:
3392:
3332:
3184:
3058:
2975:
2950:
2930:
2764:
2199:
1163:
1134:
Mueller-Harvey I, Feucht W, Polster J, TrnkovĂĄ L, Burgos P, Parker AW, Botchway SW (March 2012).
687:
648:
525:
355:
287:
1844:"Article 13 (5): Cocoa flavanols; Search filters: Claim status - authorised; search - flavanols"
1439:
Actis-Goretta L, LÊvèques A, Rein M, Teml A, Schäfer C, Hofmann U, et al. (October 2013).
831:
and EFSA have advised for caution, recommending intake should not exceed 800 mg per day.
3284:
3200:
3154:
3098:
3083:
3073:
3033:
3028:
2945:
2681:
2489:
2381:
1930:
1898:
1825:
1776:
1727:
1656:
1617:
Ottaviani JI, Fong R, Kimball J, Ensunsa JL, Britten A, Lucarelli D, et al. (June 2018).
1596:
1536:
1501:
1462:
1421:
1372:
1320:
1277:
1254:
1218:
1155:
1116:
1065:
1042:
993:
967:
714:
610:
3205:
3088:
2940:
2807:
2211:
2102:
1920:
1910:
1877:
1815:
1807:
1766:
1758:
1717:
1709:
1696:
Younes M, Aggett P, Aguilar F, Crebelli R, Dusemund B, FilipiÄ M, et al. (April 2018).
1646:
1638:
1586:
1578:
1528:
1493:
1452:
1411:
1403:
1362:
1354:
1310:
1246:
1208:
1147:
1106:
1098:
1032:
1024:
957:
949:
914:
801:
673:
555:
433:
213:
171:
164:, from which it derives its name. Heating catechin past its point of decomposition releases
103:
83:
75:
3352:
3327:
3093:
3063:
2995:
2990:
2823:
2447:
2442:
2437:
2392:
846:
793:
777:
773:
769:
753:
724:
168:(also called catechol), which explains the common origin of the names of these compounds.
114:
1634:
1574:
1341:
Del RĂo D, RodrĂguez Mateos A, Spencer JP, Tognolini M, Borges G, Crozier A (May 2013).
1011:
Del Rio D, Rodriguez-Mateos A, Spencer JP, Tognolini M, Borges G, Crozier A (May 2013).
618:
3133:
3078:
3053:
3048:
3038:
3011:
2985:
2970:
2960:
2870:
2560:
2452:
2322:
2278:
1925:
1820:
1795:
1771:
1746:
1722:
1697:
1651:
1618:
1591:
1558:
1416:
1391:
1367:
1342:
1111:
1086:
1037:
1012:
962:
937:
850:
824:
591:
453:
234:
179:
1794:
Raman G, Avendano EE, Chen S, Wang J, Matson J, Gayer B, et al. (November 2019).
3425:
3217:
3159:
3118:
3016:
2980:
2875:
2575:
2555:
2545:
2207:
2159:
1745:
Ried K, Fakler P, Stocks NP, et al. (Cochrane
Hypertension Group) (April 2017).
1532:
828:
805:
654:
531:
175:
107:
2481:
1167:
3222:
3138:
2920:
2895:
2817:
2812:
2710:
2318:
2263:
2094:
2012:
1762:
862:
854:
719:
195:
165:
1899:"Flavan-3-ols and cardiometabolic health: First ever dietary bioactive guideline"
3227:
3179:
2890:
2745:
2550:
2299:
2240:
2170:
2067:
866:
561:
419:
395:
381:
217:
202:
183:
149:
91:
1915:
1642:
94:. They play a part in plant defense and are present in the majority of plants.
2905:
2900:
2880:
2855:
2850:
2840:
2797:
2591:
2529:
2457:
2350:
2345:
2250:
2235:
2230:
2188:
2056:
1151:
840:
728:), although the content is affected considerably by processing, especially in
695:
191:
87:
1882:
1865:
1713:
1213:
1196:
748:. Their content in food is variable and affected by various factors, such as
2787:
2565:
2513:
2400:
2360:
2258:
2222:
2079:
2052:
2044:
2003:
1995:
1457:
1440:
1315:
1298:
997:
871:
817:
741:
732:. Flavan-3-ols are also present in the human diet in fruits, in particular
729:
624:
228:
224:
118:
55:
1934:
1829:
1780:
1731:
1660:
1600:
1505:
1497:
1466:
1425:
1376:
1324:
1258:
1222:
1159:
1120:
1046:
971:
1952:
1811:
1540:
1407:
1358:
1028:
3164:
2915:
2910:
2865:
2845:
2534:
2369:
2295:
2184:
2175:
2155:
2146:
2075:
2029:
1102:
781:
749:
361:
187:
145:
126:
67:
31:
953:
39:
17:
3174:
3113:
2337:
2033:
2021:
938:"Flavan-3-ols Are an Effective Chemical Defense against Rust Infection"
820:
785:
161:
1963:
1582:
1250:
156:, with (â)-epicatechin and (+)-catechin being the most common optical
2570:
2377:
2116:
2083:
157:
153:
139:
59:
1135:
160:
found in nature. Catechin was first isolated from the plant extract
1197:"Procyanidin content and variation in some commonly consumed foods"
3108:
797:
784:. These compounds are taken up and metabolized upon uptake in the
737:
699:
233:
205:
122:
38:
857:, with only minor effects demonstrated, as of 2019. In 2015, the
704:
Reported range of flavan-3-ol content in foods commonly consumed.
1297:
Manach C, Scalbert A, Morand C, RĂŠmĂŠsy C, JimĂŠnez L (May 2004).
745:
733:
2760:
2485:
1967:
709:
1181:
2756:
254:
1557:
Ottaviani JI, Borges G, Momma TY, et al. (July 2016).
1698:"Scientific opinion on the safety of green tea catechins"
1484:-methylated and glucuronidated in the small intestine".
252:(FLIM) can be used to detect flavanols in plant cells.
212:, which is commonly the most abundant catechin in tea.
1195:
Hammerstone JF, Lazarus SA, Schmitz HH (August 2000).
113:
Flavan-3-ols possess two chiral carbons, meaning four
3315:
3193:
3147:
3004:
2929:
2833:
2796:
2738:
2717:
2705:
2696:
3â-O-methyl-(-)-epicatechin 7-O-β-D-glucopyranoside
2611:
2584:
2520:
2413:
2391:
2368:
2359:
2336:
2309:
2286:
2277:
2249:
2221:
2198:
2169:
2140:
2124:
2115:
2093:
2066:
2043:
2020:
2011:
2002:
1486:
1062:
Medicinal
Natural Products: a biosynthetic approach
792:-methylation and glucuronidation, and then further
1846:. European Commission, EU Register. 31 March 2015
1612:
1610:
1182:"Database on polyphenol content in foods, v. 3.6"
845:Research has shown that flavan-3-ols may affect
1299:"Polyphenols: food sources and bioavailability"
2772:
2497:
1979:
841:Cocoa bean § Phytochemicals and research
696:Cocoa bean § Phytochemicals and research
190:, respectively, similar to the difference in
8:
983:
981:
1751:The Cochrane Database of Systematic Reviews
2779:
2765:
2757:
2504:
2490:
2482:
2365:
2283:
2121:
2017:
2008:
1986:
1972:
1964:
1800:The American Journal of Clinical Nutrition
1445:The American Journal of Clinical Nutrition
1396:The American Journal of Clinical Nutrition
1303:The American Journal of Clinical Nutrition
1239:Journal of Agricultural and Food Chemistry
333:
1924:
1914:
1881:
1819:
1770:
1721:
1650:
1590:
1456:
1415:
1366:
1314:
1212:
1110:
1036:
961:
227:, flavan-3-ols do not generally exist as
1272:Mabrym H, Harborne JB, Mabry TJ (1975).
250:Fluorescence-lifetime imaging microscopy
928:
881:
3250:European Cocoa and Chocolate Directive
1064:. John Wiley & Sons. p. 168.
3265:International Cocoa Quarantine Centre
1678:. Health Canada, Government of Canada
1552:
1550:
1336:
1334:
62:that possess a 2-phenyl-3,4-dihydro-2
7:
3233:CĂ´te d'IvoireâGhana Cocoa Initiative
2627:(Afzelechin-3-O-β-D-glucopyranoside)
3302:Production in SĂŁo TomĂŠ and PrĂncipe
2656:(+)-Catechin 7-O-β-D-xylopyranoside
2621:(Afzelechin-3-O-β-D-xylopyranoside)
1747:"Effect of cocoa on blood pressure"
988:Schwitters B, Masquelier J (1995).
1674:Health Canada (12 December 2017).
1347:Antioxidants & Redox Signaling
1017:Antioxidants & Redox Signaling
25:
43:Chemical structure of flavan-3-ol
3400:
3387:
3386:
3260:International Cocoa Organization
3211:Child labour in cocoa production
2686:(+)-catechin 7-O-Îą-L-arabinoside
2602:4â˛-O-methyl-(â)-epigallocatechin
1951:
897:
884:
647:
617:
584:
554:
524:
491:
460:
426:
388:
354:
208:of the catechins; an example is
3401:
772:of flavan-3-ols depends on the
302:, E10, anthocyanidin synthase (
243:Biosynthesis of (â)-epicatechin
178:contain an additional phenolic
27:Category of polyphenol compound
2423:List of phytochemicals in food
1763:10.1002/14651858.CD008893.pub3
1085:Winkel-Shirley B (June 2001).
764:Bioavailability and metabolism
304:leucoanthocyanidin dioxygenase
1:
3275:Philippine chocolate industry
776:, type of compound and their
708:Flavan-3-ols are abundant in
220:are oligomeric flavan-3-ols.
106:) and higher order polymers (
1533:10.1016/0006-2952(71)90449-7
1276:. London: Chapman and Hall.
503:(â)-Epigallocatechin gallate
284:naringenin-chalcone synthase
712:derived from the tea plant
300:dihydroflavanol 4-reductase
268:phenylalanine ammonia lyase
3468:
3239:The Dark Side of Chocolate
2661:Epicatechin-3â˛-O-glucoside
1643:10.1038/s41598-018-28333-w
838:
685:
223:In contrast to many other
58:. They are derivatives of
50:(sometimes referred to as
29:
3381:
3292:Production in Ivory Coast
2470:
1207:(8S Suppl): 2086Sâ2092S.
1152:10.1016/j.aca.2011.12.068
282:, E5, chalcone synthase (
3270:Manufacturers (vertical)
2725:Epigallocatechin gallate
2585:O-methylated flavan-3ols
1916:10.1093/advances/nmac105
1883:10.2903/j.efsa.2014.3654
1714:10.2903/j.efsa.2018.5239
1521:Biochemical Pharmacology
1201:The Journal of Nutrition
1184:. Phenol Explorer. 2016.
911:Epigallocatechin gallate
812:Possible adverse effects
722:(made from the seeds of
499:Epigallocatechin gallate
292:Flavonoid 3'-hydroxylase
210:epigallocatechin gallate
133:. Early use of the term
80:epigallocatechin gallate
30:Not to be confused with
3129:Chocolate-covered foods
2641:Catechin-4'-O-glucoside
2636:Catechin-3'-O-glucoside
2512:Flavan-3-ols and their
2433:O-methylated flavonoids
2428:C-methylated flavonoids
1458:10.3945/ajcn.113.065789
398:, EC, (â)-Epicatechin (
308:anthocyanidin reductase
296:flavonone 3-hydroxylase
280:4-coumaroyl: CoA-ligase
276:cinnamate 4-hydroxylase
3307:World Cocoa Foundation
2651:Catechin-7-O-glucoside
2646:Catechin-5-O-glucoside
2631:Catechin-3-O-glucoside
2473:Flavonoid biosynthesis
2311:3-hydroxyanthocyanidin
1498:10.1006/bbrc.2000.3701
1214:10.1093/jn/130.8.2086S
1140:Analytica Chimica Acta
705:
272:tyrosine ammonia lyase
260:
239:
201:Catechin gallates are
44:
3297:Production in Nigeria
3255:HarkinâEngel Protocol
3044:Chocolate chip cookie
2730:Gallocatechin gallate
2288:3-deoxyanthocyanidins
1903:Advances in Nutrition
1359:10.1089/ars.2012.4581
1316:10.1093/ajcn/79.5.727
1029:10.1089/ars.2012.4581
718:, as well as in some
703:
310:. HSCoA, Coenzyme A.
258:
237:
42:
3245:Environmental impact
3104:Cioccolato di Modica
2594:(3-O-methylcatechin)
1960:at Wikimedia Commons
1103:10.1104/pp.126.2.485
54:) are a subgroup of
3362:Military chocolate
3323:Chocolate addiction
3280:Production in Ghana
3069:Chocolate ice cream
2886:Tetramethylpyrazine
2666:Glochiflavanoside A
2541:Epicatechin gallate
1812:10.1093/ajcn/nqz178
1635:2018NatSR...8.9859O
1575:2016NatSR...629034O
1408:10.1093/ajcn/nqy229
1245:(19): 10518â10527.
954:10.1104/pp.17.00842
859:European Commission
692:Polyphenols in wine
468:Epicatechin gallate
336:
125:, which are called
72:epicatechin gallate
3333:Chocolate fountain
3059:Chocolate crackles
1623:Scientific Reports
1563:Scientific Reports
1060:Dewick PM (2009).
905:(â)-epicatechin-3-
706:
688:Polyphenols in tea
611:Proguibourtinidins
334:
288:chalcone isomerase
261:
240:
98:Chemical structure
45:
3419:
3418:
3343:Chocolate museums
3338:Legal definitions
3285:Ghana Cocoa Board
3201:Organic chocolate
3155:Aerated chocolate
3099:Chocolate truffle
3084:Chocolate pudding
3074:Chocolate liqueur
3034:Chocolate brownie
3029:Chocolate biscuit
2754:
2753:
2479:
2478:
2466:
2465:
2409:
2408:
2382:Isoliquiritigenin
2332:
2331:
2273:
2272:
2111:
2110:
1956:Media related to
1583:10.1038/srep29034
1527:(12): 3435â3445.
1353:(14): 1818â1892.
1283:978-0-412-11960-6
1251:10.1021/jf102391q
1071:978-0-471-49641-0
1023:(14): 1818â1892.
847:vascular function
715:Camellia sinensis
679:
678:
674:Prorobinetinidins
364:, C, (+)-Catechin
325:
321:
317:
313:
214:Proanthocyanidins
182:when compared to
104:proanthocyanidins
84:proanthocyanidins
16:(Redirected from
3459:
3409:
3404:
3403:
3395:
3390:
3389:
3206:Fair trade cocoa
3089:Chocolate spread
2933:
2808:Chocolate liquor
2800:
2790:
2781:
2774:
2767:
2758:
2546:Epigallocatechin
2506:
2499:
2492:
2483:
2448:Prenylflavonoids
2443:Pyranoflavonoids
2438:Furanoflavonoids
2366:
2284:
2212:Leucodelphinidin
2200:Flavan-3,4-diols
2122:
2103:Dalbergichromene
2018:
2009:
1988:
1981:
1974:
1965:
1955:
1939:
1938:
1928:
1918:
1894:
1888:
1887:
1885:
1862:
1856:
1855:
1853:
1851:
1840:
1834:
1833:
1823:
1806:(5): 1067â1078.
1791:
1785:
1784:
1774:
1742:
1736:
1735:
1725:
1693:
1687:
1686:
1684:
1683:
1671:
1665:
1664:
1654:
1614:
1605:
1604:
1594:
1554:
1545:
1544:
1516:
1510:
1509:
1477:
1471:
1470:
1460:
1436:
1430:
1429:
1419:
1402:(6): 1229â1237.
1387:
1381:
1380:
1370:
1338:
1329:
1328:
1318:
1294:
1288:
1287:
1269:
1263:
1262:
1233:
1227:
1226:
1216:
1192:
1186:
1185:
1178:
1172:
1171:
1131:
1125:
1124:
1114:
1091:Plant Physiology
1082:
1076:
1075:
1057:
1051:
1050:
1040:
1008:
1002:
1001:
992:(3rd ed.).
985:
976:
975:
965:
948:(4): 1560â1578.
942:Plant Physiology
933:
915:Epigallocatechin
909:-gallate; EGCG,
901:
888:
816:As catechins in
651:
621:
588:
558:
528:
495:
464:
434:Epigallocatechin
430:
392:
358:
337:
326:-phenylalanine.
323:
319:
315:
311:
172:Epigallocatechin
115:diastereoisomers
76:epigallocatechin
21:
3467:
3466:
3462:
3461:
3460:
3458:
3457:
3456:
3422:
3421:
3420:
3415:
3414:
3407:
3393:
3377:
3353:Cocoa smuggling
3328:Chocolate bloom
3311:
3189:
3143:
3094:Chocolate syrup
3064:Chocolate gravy
3054:Chocolate coins
3000:
2931:
2925:
2829:
2824:Theobroma cacao
2798:
2792:
2788:
2785:
2755:
2750:
2734:
2713:
2701:
2607:
2598:Ourateacatechin
2580:
2516:
2510:
2480:
2475:
2462:
2405:
2393:Dihydrochalcone
2387:
2355:
2328:
2305:
2269:
2245:
2217:
2194:
2173:
2165:
2144:
2136:
2107:
2089:
2062:
2039:
1998:
1992:
1948:
1943:
1942:
1896:
1895:
1891:
1864:
1863:
1859:
1849:
1847:
1842:
1841:
1837:
1793:
1792:
1788:
1757:(5): CD008893.
1744:
1743:
1739:
1695:
1694:
1690:
1681:
1679:
1673:
1672:
1668:
1616:
1615:
1608:
1556:
1555:
1548:
1518:
1517:
1513:
1479:
1478:
1474:
1438:
1437:
1433:
1389:
1388:
1384:
1340:
1339:
1332:
1296:
1295:
1291:
1284:
1271:
1270:
1266:
1235:
1234:
1230:
1194:
1193:
1189:
1180:
1179:
1175:
1133:
1132:
1128:
1084:
1083:
1079:
1072:
1059:
1058:
1054:
1010:
1009:
1005:
990:OPC in Practice
987:
986:
979:
935:
934:
930:
925:
918:
902:
893:
889:
880:
843:
837:
814:
770:bioavailability
766:
725:Theobroma cacao
698:
684:
682:Dietary sources
670:
666:
662:
640:
636:
632:
607:
603:
599:
577:
573:
569:
547:
543:
539:
517:
513:
509:
502:
484:
480:
476:
454:Prodelphinidins
450:
446:
442:
416:
412:
408:
378:
374:
370:
332:
245:
100:
35:
28:
23:
22:
15:
12:
11:
5:
3465:
3463:
3455:
3454:
3449:
3444:
3442:Phytochemicals
3439:
3434:
3424:
3423:
3417:
3416:
3413:
3412:
3398:
3383:
3382:
3379:
3378:
3376:
3375:
3374:
3373:
3368:
3360:
3355:
3350:
3345:
3340:
3335:
3330:
3325:
3319:
3317:
3313:
3312:
3310:
3309:
3304:
3299:
3294:
3289:
3288:
3287:
3277:
3272:
3267:
3262:
3257:
3252:
3247:
3242:
3235:
3230:
3225:
3220:
3215:
3214:
3213:
3203:
3197:
3195:
3191:
3190:
3188:
3187:
3182:
3177:
3172:
3167:
3162:
3157:
3151:
3149:
3145:
3144:
3142:
3141:
3136:
3134:Mint chocolate
3131:
3126:
3121:
3116:
3111:
3106:
3101:
3096:
3091:
3086:
3081:
3079:Chocolate milk
3076:
3071:
3066:
3061:
3056:
3051:
3049:Chocolate chip
3046:
3041:
3039:Chocolate cake
3036:
3031:
3026:
3025:
3024:
3014:
3008:
3006:
3002:
3001:
2999:
2998:
2993:
2988:
2983:
2978:
2973:
2968:
2963:
2958:
2953:
2948:
2943:
2937:
2935:
2927:
2926:
2924:
2923:
2918:
2913:
2908:
2903:
2898:
2893:
2888:
2883:
2878:
2873:
2871:Phenethylamine
2868:
2863:
2858:
2853:
2848:
2843:
2837:
2835:
2831:
2830:
2828:
2827:
2820:
2815:
2810:
2804:
2802:
2794:
2793:
2786:
2784:
2783:
2776:
2769:
2761:
2752:
2751:
2749:
2748:
2742:
2740:
2736:
2735:
2733:
2732:
2727:
2721:
2719:
2718:Gallate esters
2715:
2714:
2709:
2707:
2703:
2702:
2700:
2699:
2689:
2679:
2663:
2658:
2653:
2648:
2643:
2638:
2633:
2628:
2622:
2615:
2613:
2609:
2608:
2606:
2605:
2595:
2588:
2586:
2582:
2581:
2579:
2578:
2573:
2568:
2563:
2561:Guibourtinidol
2558:
2553:
2548:
2543:
2538:
2532:
2526:
2524:
2518:
2517:
2511:
2509:
2508:
2501:
2494:
2486:
2477:
2476:
2471:
2468:
2467:
2464:
2463:
2461:
2460:
2455:
2453:Methylenedioxy
2450:
2445:
2440:
2435:
2430:
2425:
2419:
2417:
2411:
2410:
2407:
2406:
2404:
2403:
2397:
2395:
2389:
2388:
2386:
2385:
2374:
2372:
2363:
2357:
2356:
2354:
2353:
2348:
2342:
2340:
2334:
2333:
2330:
2329:
2327:
2326:
2323:Guibourtinidin
2315:
2313:
2307:
2306:
2304:
2303:
2292:
2290:
2281:
2279:Anthocyanidins
2275:
2274:
2271:
2270:
2268:
2267:
2261:
2255:
2253:
2247:
2246:
2244:
2243:
2238:
2233:
2227:
2225:
2219:
2218:
2216:
2215:
2204:
2202:
2196:
2195:
2193:
2192:
2181:
2179:
2167:
2166:
2164:
2163:
2152:
2150:
2138:
2137:
2135:
2134:
2128:
2126:
2119:
2113:
2112:
2109:
2108:
2106:
2105:
2099:
2097:
2091:
2090:
2088:
2087:
2072:
2070:
2064:
2063:
2061:
2060:
2049:
2047:
2041:
2040:
2038:
2037:
2026:
2024:
2015:
2006:
2000:
1999:
1993:
1991:
1990:
1983:
1976:
1968:
1962:
1961:
1947:
1946:External links
1944:
1941:
1940:
1909:(6): 2070â83.
1889:
1857:
1835:
1786:
1737:
1688:
1666:
1606:
1546:
1511:
1492:(2): 507â512.
1472:
1451:(4): 924â933.
1431:
1382:
1330:
1309:(5): 727â747.
1289:
1282:
1274:The Flavonoids
1264:
1228:
1187:
1173:
1126:
1097:(2): 485â493.
1077:
1070:
1052:
1003:
977:
927:
926:
924:
921:
920:
919:
903:
896:
894:
890:
883:
879:
876:
851:blood pressure
836:
833:
813:
810:
800:. The colonic
778:stereochemical
765:
762:
683:
680:
677:
676:
671:
668:
664:
660:
657:
652:
644:
643:
641:
638:
634:
630:
627:
622:
614:
613:
608:
605:
601:
597:
594:
592:Guibourtinidol
589:
581:
580:
578:
575:
571:
567:
564:
559:
551:
550:
548:
545:
541:
537:
534:
529:
521:
520:
518:
515:
511:
507:
504:
496:
488:
487:
485:
482:
478:
474:
471:
465:
457:
456:
451:
448:
444:
440:
437:
431:
423:
422:
417:
414:
410:
406:
403:
393:
385:
384:
379:
376:
372:
368:
365:
359:
351:
350:
347:
344:
341:
331:
328:
244:
241:
180:hydroxyl group
108:anthocyanidins
99:
96:
26:
24:
14:
13:
10:
9:
6:
4:
3:
2:
3464:
3453:
3450:
3448:
3445:
3443:
3440:
3438:
3435:
3433:
3430:
3429:
3427:
3411:
3410:
3399:
3397:
3396:
3385:
3384:
3380:
3372:
3371:United States
3369:
3367:
3364:
3363:
3361:
3359:
3356:
3354:
3351:
3349:
3346:
3344:
3341:
3339:
3336:
3334:
3331:
3329:
3326:
3324:
3321:
3320:
3318:
3314:
3308:
3305:
3303:
3300:
3298:
3295:
3293:
3290:
3286:
3283:
3282:
3281:
3278:
3276:
3273:
3271:
3268:
3266:
3263:
3261:
3258:
3256:
3253:
3251:
3248:
3246:
3243:
3241:
3240:
3236:
3234:
3231:
3229:
3226:
3224:
3221:
3219:
3218:Big Chocolate
3216:
3212:
3209:
3208:
3207:
3204:
3202:
3199:
3198:
3196:
3192:
3186:
3183:
3181:
3178:
3176:
3173:
3171:
3170:Dutch process
3168:
3166:
3163:
3161:
3160:Broma process
3158:
3156:
3153:
3152:
3150:
3146:
3140:
3137:
3135:
3132:
3130:
3127:
3125:
3122:
3120:
3119:Hot chocolate
3117:
3115:
3112:
3110:
3107:
3105:
3102:
3100:
3097:
3095:
3092:
3090:
3087:
3085:
3082:
3080:
3077:
3075:
3072:
3070:
3067:
3065:
3062:
3060:
3057:
3055:
3052:
3050:
3047:
3045:
3042:
3040:
3037:
3035:
3032:
3030:
3027:
3023:
3020:
3019:
3018:
3017:Chocolate bar
3015:
3013:
3010:
3009:
3007:
3003:
2997:
2994:
2992:
2989:
2987:
2984:
2982:
2981:Raw chocolate
2979:
2977:
2974:
2972:
2969:
2967:
2964:
2962:
2959:
2957:
2954:
2952:
2949:
2947:
2944:
2942:
2939:
2938:
2936:
2934:
2928:
2922:
2919:
2917:
2914:
2912:
2909:
2907:
2904:
2902:
2899:
2897:
2894:
2892:
2889:
2887:
2884:
2882:
2879:
2877:
2876:Phenylalanine
2874:
2872:
2869:
2867:
2864:
2862:
2859:
2857:
2854:
2852:
2849:
2847:
2844:
2842:
2839:
2838:
2836:
2832:
2826:
2825:
2821:
2819:
2816:
2814:
2811:
2809:
2806:
2805:
2803:
2801:
2795:
2791:
2782:
2777:
2775:
2770:
2768:
2763:
2762:
2759:
2747:
2744:
2743:
2741:
2737:
2731:
2728:
2726:
2723:
2722:
2720:
2716:
2712:
2708:
2704:
2697:
2693:
2690:
2687:
2683:
2680:
2678:
2675:
2671:
2667:
2664:
2662:
2659:
2657:
2654:
2652:
2649:
2647:
2644:
2642:
2639:
2637:
2634:
2632:
2629:
2626:
2625:Arthromerin B
2623:
2620:
2619:Arthromerin A
2617:
2616:
2614:
2610:
2603:
2599:
2596:
2593:
2590:
2589:
2587:
2583:
2577:
2576:Robinetinidol
2574:
2572:
2569:
2567:
2564:
2562:
2559:
2557:
2556:Gallocatechin
2554:
2552:
2549:
2547:
2544:
2542:
2539:
2537:(Epicatechin)
2536:
2533:
2531:
2528:
2527:
2525:
2523:
2519:
2515:
2507:
2502:
2500:
2495:
2493:
2488:
2487:
2484:
2474:
2469:
2459:
2456:
2454:
2451:
2449:
2446:
2444:
2441:
2439:
2436:
2434:
2431:
2429:
2426:
2424:
2421:
2420:
2418:
2416:
2415:Miscellaneous
2412:
2402:
2399:
2398:
2396:
2394:
2390:
2383:
2379:
2376:
2375:
2373:
2371:
2367:
2364:
2362:
2358:
2352:
2349:
2347:
2344:
2343:
2341:
2339:
2335:
2324:
2320:
2317:
2316:
2314:
2312:
2308:
2301:
2297:
2294:
2293:
2291:
2289:
2285:
2282:
2280:
2276:
2265:
2262:
2260:
2257:
2256:
2254:
2252:
2248:
2242:
2239:
2237:
2234:
2232:
2229:
2228:
2226:
2224:
2220:
2213:
2209:
2208:Leucocyanidin
2206:
2205:
2203:
2201:
2197:
2190:
2186:
2183:
2182:
2180:
2177:
2172:
2168:
2161:
2160:Gallocatechol
2157:
2154:
2153:
2151:
2148:
2143:
2139:
2133:
2132:Luteoliflavan
2130:
2129:
2127:
2123:
2120:
2118:
2114:
2104:
2101:
2100:
2098:
2096:
2095:Neoflavonoids
2092:
2085:
2081:
2077:
2074:
2073:
2071:
2069:
2065:
2058:
2054:
2051:
2050:
2048:
2046:
2042:
2035:
2031:
2028:
2027:
2025:
2023:
2019:
2016:
2014:
2013:Anthoxanthins
2010:
2007:
2005:
2001:
1997:
1989:
1984:
1982:
1977:
1975:
1970:
1969:
1966:
1959:
1954:
1950:
1949:
1945:
1936:
1932:
1927:
1922:
1917:
1912:
1908:
1904:
1900:
1893:
1890:
1884:
1879:
1875:
1871:
1867:
1861:
1858:
1845:
1839:
1836:
1831:
1827:
1822:
1817:
1813:
1809:
1805:
1801:
1797:
1790:
1787:
1782:
1778:
1773:
1768:
1764:
1760:
1756:
1752:
1748:
1741:
1738:
1733:
1729:
1724:
1719:
1715:
1711:
1708:(4): e05239.
1707:
1703:
1699:
1692:
1689:
1677:
1670:
1667:
1662:
1658:
1653:
1648:
1644:
1640:
1636:
1632:
1628:
1624:
1620:
1613:
1611:
1607:
1602:
1598:
1593:
1588:
1584:
1580:
1576:
1572:
1568:
1564:
1560:
1553:
1551:
1547:
1542:
1538:
1534:
1530:
1526:
1522:
1515:
1512:
1507:
1503:
1499:
1495:
1491:
1487:
1483:
1476:
1473:
1468:
1464:
1459:
1454:
1450:
1446:
1442:
1435:
1432:
1427:
1423:
1418:
1413:
1409:
1405:
1401:
1397:
1393:
1386:
1383:
1378:
1374:
1369:
1364:
1360:
1356:
1352:
1348:
1344:
1337:
1335:
1331:
1326:
1322:
1317:
1312:
1308:
1304:
1300:
1293:
1290:
1285:
1279:
1275:
1268:
1265:
1260:
1256:
1252:
1248:
1244:
1240:
1232:
1229:
1224:
1220:
1215:
1210:
1206:
1202:
1198:
1191:
1188:
1183:
1177:
1174:
1169:
1165:
1161:
1157:
1153:
1149:
1145:
1141:
1137:
1130:
1127:
1122:
1118:
1113:
1108:
1104:
1100:
1096:
1092:
1088:
1081:
1078:
1073:
1067:
1063:
1056:
1053:
1048:
1044:
1039:
1034:
1030:
1026:
1022:
1018:
1014:
1007:
1004:
999:
995:
991:
984:
982:
978:
973:
969:
964:
959:
955:
951:
947:
943:
939:
932:
929:
922:
916:
912:
908:
900:
895:
887:
882:
877:
875:
873:
868:
864:
860:
856:
852:
848:
842:
834:
832:
830:
829:Health Canada
826:
822:
819:
811:
809:
807:
806:hippuric acid
803:
799:
795:
791:
787:
783:
779:
775:
771:
763:
761:
759:
755:
751:
747:
743:
739:
735:
731:
727:
726:
721:
717:
716:
711:
702:
697:
693:
689:
681:
675:
672:
658:
656:
655:Robinetinidol
653:
650:
646:
645:
642:
628:
626:
623:
620:
616:
615:
612:
609:
595:
593:
590:
587:
583:
582:
579:
565:
563:
560:
557:
553:
552:
549:
535:
533:
532:Epiafzelechin
530:
527:
523:
522:
519:
505:
500:
497:
494:
490:
489:
486:
472:
469:
466:
463:
459:
458:
455:
452:
438:
435:
432:
429:
425:
424:
421:
418:
404:
401:
397:
394:
391:
387:
386:
383:
380:
366:
363:
360:
357:
353:
352:
348:
345:
342:
339:
338:
335:Flavan-3-ols
329:
327:
309:
305:
301:
297:
293:
289:
285:
281:
277:
273:
269:
265:
257:
253:
251:
242:
236:
232:
230:
226:
221:
219:
215:
211:
207:
204:
199:
197:
193:
189:
185:
181:
177:
176:gallocatechin
173:
169:
167:
163:
159:
155:
151:
147:
143:
141:
136:
132:
130:
124:
120:
116:
111:
109:
105:
97:
95:
93:
89:
85:
81:
77:
73:
69:
65:
61:
57:
53:
49:
41:
37:
33:
19:
3405:
3391:
3348:Chocolatiers
3316:Other topics
3237:
3223:Chocolaterie
2921:Valeric acid
2896:Theophylline
2860:
2822:
2818:Cocoa solids
2813:Cocoa butter
2746:Thearubigins
2711:Phylloflavan
2692:Symplocoside
2522:Flavan-3-ols
2521:
2414:
2319:Apigeninidin
2264:Aromadendrin
2171:Flavan-4-ols
2142:Flavan-3-ols
2141:
1958:Flavan-3-ols
1906:
1902:
1892:
1873:
1870:EFSA Journal
1869:
1860:
1848:. Retrieved
1838:
1803:
1799:
1789:
1754:
1750:
1740:
1705:
1702:EFSA Journal
1701:
1691:
1680:. Retrieved
1669:
1626:
1622:
1569:(1): 29034.
1566:
1562:
1524:
1520:
1514:
1489:
1485:
1481:
1475:
1448:
1444:
1434:
1399:
1395:
1385:
1350:
1346:
1306:
1302:
1292:
1273:
1267:
1242:
1238:
1231:
1204:
1200:
1190:
1176:
1143:
1139:
1129:
1094:
1090:
1080:
1061:
1055:
1020:
1016:
1006:
989:
945:
941:
931:
906:
867:cocoa solids
863:health claim
855:blood lipids
844:
815:
789:
788:, mainly by
767:
723:
713:
707:
420:Procyanidins
399:
382:Procyanidins
263:
262:
246:
222:
218:thearubigins
200:
196:pyrocatechol
194:compared to
170:
166:pyrocatechol
144:
135:bioflavonoid
134:
128:
112:
101:
92:thearubigins
63:
51:
48:Flavan-3-ols
47:
46:
36:
3447:Polyphenols
3366:Switzerland
3228:Chocolatier
3180:Sugar crust
3012:Caffè mocha
2891:Theobromine
2861:Flavan-3-ol
2551:Fisetinidol
2458:Castavinols
2300:Delphinidin
2251:Flavanonols
2241:Eriodictyol
2068:Isoflavones
1876:(5). 2014.
1850:8 September
1629:(1): 9859.
861:approved a
825:hepatotoxic
794:metabolized
774:food matrix
758:preparation
734:pome fruits
562:Fisetinidol
396:Epicatechin
318:-tyrosine,
274:(TAL), E3,
270:(PAL), E2,
231:in plants.
203:gallic acid
184:epicatechin
150:epicatechin
88:theaflavins
3452:Flavonoids
3426:Categories
2956:Couverture
2906:Tryptophan
2901:Tryptamine
2881:Salsolinol
2856:Enkephalin
2851:Endorphins
2841:Anandamide
2834:Components
2799:Cocoa bean
2706:Acetylated
2612:Glycosides
2592:Meciadanol
2530:Afzelechin
2514:glycosides
2351:Leptosidin
2346:Aureusidin
2236:Naringenin
2231:Hesperidin
2223:Flavanones
2189:Luteoforol
2057:Kaempferol
2004:Flavonoids
1996:flavonoids
1682:2022-05-06
923:References
872:biomarkers
839:See also:
802:microbiome
782:epiatechin
754:processing
742:vegetables
686:See also:
349:Oligomers
229:glycosides
225:flavonoids
192:pyrogallol
56:flavonoids
3437:Nutrition
3432:Flavanols
3185:Tempering
3148:Processes
3124:beverages
2789:Chocolate
2566:Mesquitol
2401:Phloretin
2370:Chalcones
2361:Chalcones
2259:Taxifolin
2176:flavanols
2147:flavanols
2080:Genistein
2053:Quercetin
2045:Flavonols
1994:Types of
1146:: 68â75.
818:green tea
730:chocolate
625:Mesquitol
330:Aglycones
119:quercitin
52:flavanols
3394:Category
3194:Industry
3165:Conching
3005:Products
2976:Modeling
2966:Gianduja
2951:Compound
2916:Tyrosine
2911:Tyramine
2866:Lecithin
2846:Caffeine
2682:Polydine
2535:Catechin
2296:Cyanidin
2185:Apiforol
2156:Catechin
2076:Daidzein
2030:Apigenin
2022:Flavones
1935:36190328
1830:31504087
1781:28439881
1732:32625874
1661:29959422
1601:27363516
1506:11032751
1467:23864538
1426:30358831
1377:22794138
1325:15113710
1259:20843086
1223:10917927
1168:24094780
1160:22340533
1121:11402179
1047:22794138
998:45289285
972:29070515
835:Research
750:cultivar
362:Catechin
306:), E11,
264:Figure 1
259:Figure 1
188:catechin
146:Catechin
68:catechin
32:Flavonol
18:Flavanol
3408:Outline
3358:History
3175:Enrober
3114:Ganache
2946:Belgian
2384:, et.c.
2338:Aurones
2325:, et.c.
2302:, et.c.
2266:, et.c.
2214:, et.c.
2191:, et.c.
2162:, et.c.
2117:Flavans
2059:, et.c.
2036:, et.c.
2034:Chrysin
1926:9776652
1821:6821550
1772:6478304
1723:7009618
1652:6026136
1631:Bibcode
1592:4929566
1571:Bibcode
1541:5132890
1417:6290365
1368:3619154
1112:1540115
1038:3619154
963:5717727
913:; EGC,
878:Gallery
823:can be
821:extract
796:by the
786:jejunum
738:berries
501:, EGCG,
346:Formula
286:), E6,
162:catechu
158:isomers
154:epimers
140:tannins
60:flavans
3022:brands
2941:Baking
2571:Oritin
2378:Butein
2125:Flavan
2084:Orobol
1933:
1923:
1828:
1818:
1779:
1769:
1730:
1720:
1659:
1649:
1599:
1589:
1539:
1504:
1465:
1424:
1414:
1375:
1365:
1323:
1280:
1257:
1221:
1166:
1158:
1119:
1109:
1068:
1045:
1035:
996:
970:
960:
853:, and
756:, and
744:, and
720:cocoas
694:, and
322:-Phe,
314:-Tyr,
298:, E9,
294:, E8,
290:, E7,
278:, E4,
206:esters
3109:Fudge
2996:White
2991:Swiss
2932:Types
2739:Misc.
2086:et.c.
1164:S2CID
798:liver
470:, ECG
436:, EGC
340:Image
123:rutin
3139:Mole
2986:Ruby
2971:Milk
2961:Dark
1931:PMID
1852:2022
1826:PMID
1777:PMID
1728:PMID
1657:PMID
1597:PMID
1537:PMID
1502:PMID
1463:PMID
1422:PMID
1373:PMID
1321:PMID
1278:ISBN
1255:PMID
1219:PMID
1156:PMID
1117:PMID
1066:ISBN
1043:PMID
994:OCLC
968:PMID
865:for
768:The
746:wine
710:teas
343:Name
216:and
186:and
174:and
152:are
148:and
131:nols
127:flav
121:and
1921:PMC
1911:doi
1878:doi
1816:PMC
1808:doi
1804:110
1767:PMC
1759:doi
1718:PMC
1710:doi
1647:PMC
1639:doi
1587:PMC
1579:doi
1529:doi
1494:doi
1490:277
1453:doi
1412:PMC
1404:doi
1400:108
1363:PMC
1355:doi
1311:doi
1247:doi
1209:doi
1205:130
1148:doi
1144:719
1107:PMC
1099:doi
1095:126
1033:PMC
1025:doi
958:PMC
950:doi
946:175
400:cis
110:).
3428::
2672:,
2668:,
2380:,
2321:,
2298:,
2210:,
2187:,
2158:,
2082:,
2078:,
2055:,
2032:,
1929:.
1919:.
1907:13
1905:.
1901:.
1874:12
1872:.
1868:.
1824:.
1814:.
1802:.
1798:.
1775:.
1765:.
1753:.
1749:.
1726:.
1716:.
1706:16
1704:.
1700:.
1655:.
1645:.
1637:.
1625:.
1621:.
1609:^
1595:.
1585:.
1577:.
1565:.
1561:.
1549:^
1535:.
1525:20
1523:.
1500:.
1488:.
1461:.
1449:98
1447:.
1443:.
1420:.
1410:.
1398:.
1394:.
1371:.
1361:.
1351:18
1349:.
1345:.
1333:^
1319:.
1307:79
1305:.
1301:.
1253:.
1243:58
1241:.
1217:.
1203:.
1199:.
1162:.
1154:.
1142:.
1138:.
1115:.
1105:.
1093:.
1089:.
1041:.
1031:.
1021:18
1019:.
1015:.
980:^
966:.
956:.
944:.
940:.
874:.
849:,
827:,
760:.
752:,
740:,
736:,
690:,
665:14
661:15
635:14
631:15
602:14
598:15
572:14
568:15
542:14
538:15
516:11
512:18
508:22
483:10
479:18
475:22
445:14
441:15
411:14
407:15
373:14
369:15
198:.
142:.
90:,
86:,
82:,
78:,
74:,
70:,
2780:e
2773:t
2766:v
2698:)
2694:(
2688:)
2684:(
2677:D
2674:C
2670:B
2604:)
2600:(
2505:e
2498:t
2491:v
2178:)
2174:(
2149:)
2145:(
1987:e
1980:t
1973:v
1937:.
1913::
1886:.
1880::
1854:.
1832:.
1810::
1783:.
1761::
1755:4
1734:.
1712::
1685:.
1663:.
1641::
1633::
1627:8
1603:.
1581::
1573::
1567:6
1543:.
1531::
1508:.
1496::
1482:O
1469:.
1455::
1428:.
1406::
1379:.
1357::
1327:.
1313::
1286:.
1261:.
1249::
1225:.
1211::
1170:.
1150::
1123:.
1101::
1074:.
1049:.
1027::
1000:.
974:.
952::
917:.
907:O
790:O
669:6
667:O
663:H
659:C
639:6
637:O
633:H
629:C
606:4
604:O
600:H
596:C
576:5
574:O
570:H
566:C
546:5
544:O
540:H
536:C
514:O
510:H
506:C
481:O
477:H
473:C
449:7
447:O
443:H
439:C
415:6
413:O
409:H
405:C
402:)
377:6
375:O
371:H
367:C
324:L
320:L
316:L
312:L
129:o
64:H
34:.
20:)
Text is available under the Creative Commons Attribution-ShareAlike License. Additional terms may apply.
