Abstract
Beer, one of the most commonly consumed alcoholic beverages, is rich in polyphenols and is the main dietary source of xanthohumol and related prenylflavonoids. However, to avoid haze formation caused by the interaction between polyphenols and proteins, most phenolic compounds are removed from beer and lost in the brewery waste stream via polyvinylpolypyrrolidone (PVPP) adsorption. This waste stream contains several polyphenols with high antioxidant capacity and pharmacological effects; that waste could be used as a rich, low-cost source of these compounds, though little is known about its composition and potential attributes. This work aims to review the polyphenols present in this brewery waste stream, as well as the health benefits associated with their consumption.
Keywords: Beer, hop (Humulus lupulus L.), hop bitter acids, malt, prenylated chalcones, PVPP brewery waste stream, xanthohumol.
Graphical Abstract
[http://dx.doi.org/10.1016/B978-0-12-373891-2.00001-8]
[http://dx.doi.org/10.1021/jf011345j] [PMID: 11958608]
[http://dx.doi.org/10.1016/j.foodchem.2013.08.033] [PMID: 24128467]
[http://dx.doi.org/10.1016/j.tox.2016.06.008] [PMID: 27317025]
[http://dx.doi.org/10.1093/alcalc/agt007] [PMID: 23408240]
[http://dx.doi.org/10.1016/j.jep.2014.10.058] [PMID: 25446602]
[http://dx.doi.org/10.1016/j.bcp.2014.10.001] [PMID: 25450671]
[http://dx.doi.org/10.3390/molecules21111566] [PMID: 27869750]
[http://dx.doi.org/10.1021/jf00029a014]
[http://dx.doi.org/10.1021/jf00029a014]
[http://dx.doi.org/10.1023/A:1026082325529]
[http://dx.doi.org/10.1016/j.foodres.2013.01.042]
[http://dx.doi.org/10.1111/j.1753-4887.1998.tb01670.x] [PMID: 9838798]
[http://dx.doi.org/10.1007/978-0-387-74118-5_23]
[http://dx.doi.org/10.1016/j.foodres.2011.03.050]
[http://dx.doi.org/10.1021/jf0260040] [PMID: 12617582]
[http://dx.doi.org/10.17221/690-CJFS]
[http://dx.doi.org/10.1016/j.foodchem.2014.07.154] [PMID: 25236235]
[http://dx.doi.org/10.1016/j.lwt.2015.11.017]
[http://dx.doi.org/10.1016/j.ejca.2005.04.012] [PMID: 15953717]
[http://dx.doi.org/10.1080/09168451.2015.1042832] [PMID: 25996959]
[http://dx.doi.org/10.1016/j.chroma.2009.10.068] [PMID: 19913228]
[http://dx.doi.org/10.1039/an9941900863] [PMID: 8067536]
[http://dx.doi.org/10.1021/jf960139m]
[http://dx.doi.org/10.1021/jf00058a025]
[http://dx.doi.org/10.1002/j.2050-0416.1994.tb00839.x]
[http://dx.doi.org/10.1016/j.fitote.2015.03.007] [PMID: 25771121]
[http://dx.doi.org/10.1093/jn/136.7.1862] [PMID: 16772450]
[http://dx.doi.org/10.1016/0021-9673(93)80033-5]
[http://dx.doi.org/10.1002/jssc.200500003] [PMID: 16013828]
[http://dx.doi.org/10.1016/j.chroma.2010.12.012] [PMID: 21196008]
[http://dx.doi.org/10.1139/m75-029] [PMID: 803401]
[http://dx.doi.org/10.1016/j.foodchem.2014.09.139] [PMID: 25442616]
[PMID: 16099209]
[http://dx.doi.org/10.1021/np800740m] [PMID: 19476340]
[http://dx.doi.org/10.1016/j.phanu.2015.03.001]
[http://dx.doi.org/10.1021/jf904079h] [PMID: 20329731]
[http://dx.doi.org/10.1271/bbb.59.740] [PMID: 7772843]
[http://dx.doi.org/10.1021/jf401718z] [PMID: 23971792]
[http://dx.doi.org/10.1021/bk-2012-1104.ch014]
[http://dx.doi.org/10.1094/ASBCJ-2008-0310-01]
[http://dx.doi.org/10.1002/j.2050-0416.2010.tb00412.x]
[http://dx.doi.org/10.1002/mnfr.200500027] [PMID: 15968705]
[http://dx.doi.org/10.17660/ActaHortic.2005.668.28]
[http://dx.doi.org/10.1055/s-2005-916212] [PMID: 16534727]
[http://dx.doi.org/10.1016/j.phytochem.2008.02.001] [PMID: 18358504]
[http://dx.doi.org/10.1186/1476-9255-6-26] [PMID: 19712471]
[http://dx.doi.org/10.1016/S0014-5793(99)01727-5] [PMID: 10631313]
[http://dx.doi.org/10.1093/carcin/bgm080] [PMID: 17434926]
[http://dx.doi.org/10.1271/bbb.61.1027] [PMID: 9214766]
[http://dx.doi.org/10.1021/jf034737u] [PMID: 14709013]
[http://dx.doi.org/10.1016/S0145-2126(98)00046-0] [PMID: 9680110]
[http://dx.doi.org/10.1016/j.phytol.2009.10.006]
[http://dx.doi.org/10.3892/or.2012.1925] [PMID: 22825405]
[http://dx.doi.org/10.1159/000227448] [PMID: 7854777]
[http://dx.doi.org/10.1093/carcin/bgm054] [PMID: 17372274]
[http://dx.doi.org/10.1006/bbrc.2001.5934] [PMID: 11708802]
[http://dx.doi.org/10.4162/nrp.2012.6.5.405] [PMID: 23198019]
[http://dx.doi.org/10.1016/j.nut.2012.05.004] [PMID: 22985971]
[http://dx.doi.org/10.1371/journal.pone.0033858] [PMID: 22470484]
[http://dx.doi.org/10.1017/S000711451200061X] [PMID: 22715886]
[http://dx.doi.org/10.1371/journal.pone.0087848] [PMID: 24498211]
[http://dx.doi.org/10.1016/j.clnu.2009.03.012] [PMID: 19395131]
[http://dx.doi.org/10.1186/1743-7075-5-29] [PMID: 18983673]
[http://dx.doi.org/10.1016/j.jacl.2011.03.002] [PMID: 21600524]
[http://dx.doi.org/10.1016/j.jacl.2009.11.002] [PMID: 21122628]
[http://dx.doi.org/10.1016/j.jpba.2019.02.022] [PMID: 30807916]
[http://dx.doi.org/10.1016/j.foodchem.2018.01.073] [PMID: 29478534]
[http://dx.doi.org/10.1096/fj.07-8110com] [PMID: 17666455]
[http://dx.doi.org/10.1016/j.jep.2006.07.008] [PMID: 16920300]
[http://dx.doi.org/10.1016/j.ejmech.2006.09.019] [PMID: 17112640]
[http://dx.doi.org/10.1016/j.phytochem.2004.04.025] [PMID: 15231405]
[http://dx.doi.org/10.1096/fj.05-5128fje] [PMID: 16403733]
[http://dx.doi.org/10.1016/j.biopha.2015.05.020] [PMID: 26211581]
[http://dx.doi.org/10.3109/03602539409029789] [PMID: 8082563]
[http://dx.doi.org/10.1007/978-3-642-81919-3_4]
[http://dx.doi.org/10.1016/S0304-3835(99)00328-6] [PMID: 10737704]
[http://dx.doi.org/10.1080/004982500237631] [PMID: 10752639]
[http://dx.doi.org/10.1002/jcb.21738] [PMID: 18348194]
[http://dx.doi.org/10.1002/mnfr.200500045] [PMID: 16144030]
[http://dx.doi.org/10.1016/j.ygyno.2011.04.027] [PMID: 21616523]
[http://dx.doi.org/10.1016/j.phymed.2006.01.001] [PMID: 16678392]
[http://dx.doi.org/10.1002/mnfr.200500065] [PMID: 15995977]
[http://dx.doi.org/10.1016/j.canlet.2006.02.015] [PMID: 16563612]
[PMID: 20043079]
[http://dx.doi.org/10.1021/np900230p] [PMID: 19757857]
[http://dx.doi.org/10.1016/j.tiv.2007.09.009] [PMID: 17981005]
[http://dx.doi.org/10.1055/s-0031-1295738] [PMID: 22295144]
[http://dx.doi.org/10.1016/j.intimp.2013.04.029] [PMID: 23669332]
[http://dx.doi.org/10.1016/j.phytochem.2012.04.018] [PMID: 22640929]
[http://dx.doi.org/10.1016/j.abb.2016.03.008] [PMID: 26976708]
[http://dx.doi.org/10.3390/nu2121231] [PMID: 22254006]
[http://dx.doi.org/10.1021/jf0509714] [PMID: 16076107]
[http://dx.doi.org/10.1016/j.tet.2013.02.087]
[http://dx.doi.org/10.1124/jpet.110.176925] [PMID: 21398514]
[http://dx.doi.org/10.1371/journal.pone.0047516] [PMID: 23094058]
[http://dx.doi.org/10.1021/tx200126r] [PMID: 21504213]
[http://dx.doi.org/10.1016/j.foodres.2016.04.026] [PMID: 29544832]
[http://dx.doi.org/10.1016/B978-0-12-373891-2.00032-8]
[http://dx.doi.org/10.1016/j.canlet.2008.03.049] [PMID: 18457915]
[http://dx.doi.org/10.1093/carcin/bgh095] [PMID: 14742313]
[http://dx.doi.org/10.1371/journal.pone.0027444] [PMID: 22087318]
[http://dx.doi.org/10.1002/(SICI)1097-0010(20000515)80:7<1094:: AID-JSFA569>3.0.CO;2-1]
[http://dx.doi.org/10.1179/135100002125000172] [PMID: 11981454]
[http://dx.doi.org/10.1007/PL00013940]
[http://dx.doi.org/10.1016/j.jfca.2013.11.004]
[http://dx.doi.org/10.1007/BF02490811]
[http://dx.doi.org/10.1016/j.phymed.2004.07.006] [PMID: 16360942]
[http://dx.doi.org/10.1055/s-2004-815453] [PMID: 14765291]
[http://dx.doi.org/10.1016/j.cbi.2008.06.005] [PMID: 18619951]
[http://dx.doi.org/10.1016/j.mce.2008.08.008] [PMID: 18775763]
[http://dx.doi.org/10.1210/jcem.84.6.5887] [PMID: 10372741]
[http://dx.doi.org/10.1016/S0960-0760(03)00050-5] [PMID: 12711023]
[http://dx.doi.org/10.1016/j.jsbmb.2005.05.009] [PMID: 16153822]
[http://dx.doi.org/10.1016/j.jsbmb.2004.03.118] [PMID: 15276617]
[http://dx.doi.org/10.1016/0169-6009(91)90124-I] [PMID: 1773131]
[http://dx.doi.org/10.1055/s-2006-957505] [PMID: 9741296]
[http://dx.doi.org/10.1530/rep.0.1230235] [PMID: 11866690]
[http://dx.doi.org/10.1677/joe.1.06919] [PMID: 17088409]
[http://dx.doi.org/10.1016/j.mce.2014.05.014] [PMID: 24859648]
[http://dx.doi.org/10.1016/S0021-9673(98)01001-2] [PMID: 10070768]
[http://dx.doi.org/10.1021/jf0500177] [PMID: 15884869]
[http://dx.doi.org/10.1002/ptr.2286] [PMID: 17726738]
[http://dx.doi.org/10.1016/j.jnutbio.2005.06.006] [PMID: 16169200]
[http://dx.doi.org/10.1016/S0899-9007(01)00695-5] [PMID: 11827770]
[http://dx.doi.org/10.1016/j.arabjc.2013.02.004]
[http://dx.doi.org/10.1002/mnfr.200800021] [PMID: 19065585]
[http://dx.doi.org/10.1021/jf0620719] [PMID: 17177504]
[http://dx.doi.org/10.1016/j.ejphar.2006.11.014] [PMID: 17184768]
[http://dx.doi.org/10.1111/j.0953-816X.2004.03441.x] [PMID: 15217394]
[http://dx.doi.org/10.1007/s11357-009-9124-1] [PMID: 20431987]
[http://dx.doi.org/10.1096/fasebj.13.10.1137] [PMID: 10385605]
[http://dx.doi.org/10.3390/molecules16043338] [PMID: 21512441]
[http://dx.doi.org/10.1002/eji.200425778] [PMID: 15668926]
[http://dx.doi.org/10.1016/j.mam.2010.09.002] [PMID: 20837053]
[http://dx.doi.org/10.1016/j.chemphyslip.2004.02.001] [PMID: 15081861]
[http://dx.doi.org/10.3177/jnsv.47.357] [PMID: 11814152]
[http://dx.doi.org/10.1016/j.ejphar.2009.06.022] [PMID: 19549512]
[http://dx.doi.org/10.1097/01.hjh.0000198029.22472.d9] [PMID: 16331104]
[http://dx.doi.org/10.1016/0014-2999(93)90968-N] [PMID: 8223884]
[http://dx.doi.org/10.1248/bpb.27.2035] [PMID: 15577228]
[http://dx.doi.org/10.1002/ptr.2008] [PMID: 17072829]
[http://dx.doi.org/10.1039/C4FO00818A] [PMID: 25562607]
[http://dx.doi.org/10.1016/j.atherosclerosis.2008.03.007] [PMID: 18436224]
[http://dx.doi.org/10.1093/ajcn/72.5.1150] [PMID: 11063442]
[http://dx.doi.org/10.1046/j.1538-7836.2003.00212.x] [PMID: 12871380]
[http://dx.doi.org/10.1016/j.freeradbiomed.2015.01.018] [PMID: 25645952]
[http://dx.doi.org/10.2174/138955711795305335] [PMID: 21428901]
[http://dx.doi.org/10.1158/1535-7163.MCT-06-0788] [PMID: 17876051]
[http://dx.doi.org/10.1002/jcp.10340] [PMID: 12942547]
[http://dx.doi.org/10.1093/carcin/bgh052] [PMID: 14688022]
[http://dx.doi.org/10.1016/j.jss.2008.02.036] [PMID: 18570926]
[http://dx.doi.org/10.1002/mnfr.201000005] [PMID: 20564475]
[http://dx.doi.org/10.1007/s12272-010-0519-4] [PMID: 20512478]
[http://dx.doi.org/10.1016/j.bbrc.2008.07.131] [PMID: 18680719]
[http://dx.doi.org/10.1016/j.cbi.2008.10.048] [PMID: 19028473]
[http://dx.doi.org/10.1158/1535-7163.MCT-07-0001] [PMID: 17876056]
[http://dx.doi.org/10.4161/cbt.7.7.6164] [PMID: 18443432]
[http://dx.doi.org/10.1007/s12272-010-0808-y] [PMID: 20803121]
[http://dx.doi.org/10.1177/0960327109107002] [PMID: 19755441]
[http://dx.doi.org/10.1080/01635580802666281] [PMID: 19838928]
[http://dx.doi.org/10.1016/j.foodchem.2011.07.045] [PMID: 21927533]
[http://dx.doi.org/10.1371/journal.pone.0022934] [PMID: 21857970]
[http://dx.doi.org/10.1007/s10555-006-7886-9] [PMID: 16680569]
[http://dx.doi.org/10.1002/jcp.22226] [PMID: 20458747]
[http://dx.doi.org/10.1016/j.neuroscience.2006.02.028] [PMID: 16580779]
[http://dx.doi.org/10.1016/j.yexcr.2012.02.017] [PMID: 22394507]
[http://dx.doi.org/10.1016/j.toxlet.2003.10.012] [PMID: 14700523]
[http://dx.doi.org/10.1038/aps.2009.107] [PMID: 19617894]
[http://dx.doi.org/10.1038/sj.bjp.0702879] [PMID: 10556937]
[http://dx.doi.org/10.1007/s11010-005-9085-3] [PMID: 16645725]
[http://dx.doi.org/10.1016/j.fitote.2008.04.002] [PMID: 18538949]
[http://dx.doi.org/10.4162/nrp.2011.5.2.107] [PMID: 21556223]
[http://dx.doi.org/10.4162/nrp.2012.6.3.201] [PMID: 22808343]
[PMID: 25671197]
[http://dx.doi.org/10.1179/1351000214Y.0000000117] [PMID: 25494817]
[http://dx.doi.org/10.1016/j.lfs.2007.12.021] [PMID: 18262572]
[http://dx.doi.org/10.1055/s-0029-1185944] [PMID: 19637114]
[http://dx.doi.org/10.1016/j.ejphar.2011.08.011] [PMID: 21914439]
[http://dx.doi.org/10.1016/S0232-4393(86)80010-5] [PMID: 3811648]
[http://dx.doi.org/10.1002/1099-1573(200102)15:1<39:AID-PTR684>3.0.CO;2-R] [PMID: 11180521]
[PMID: 19374167]
[http://dx.doi.org/10.1007/s005350170147] [PMID: 11211212]
[http://dx.doi.org/10.1055/s-2005-837816] [PMID: 15770537]
[http://dx.doi.org/10.1007/s00535-008-2184-7] [PMID: 18600388]
[http://dx.doi.org/10.1016/j.bmc.2008.06.049] [PMID: 18640042]
[http://dx.doi.org/10.1006/bbrc.1996.1759] [PMID: 8954085]
[http://dx.doi.org/10.1016/j.foodchem.2011.03.022] [PMID: 25212137]
[http://dx.doi.org/10.1021/np50090a003] [PMID: 1338212]
[http://dx.doi.org/10.1016/j.lfs.2016.02.032] [PMID: 26874033]
[http://dx.doi.org/10.1021/jf980737w] [PMID: 10563998]
[http://dx.doi.org/10.1016/S0278-6915(02)00329-0] [PMID: 12738180]
[http://dx.doi.org/10.1016/j.jecm.2010.12.005]
[http://dx.doi.org/10.1002/ijc.22571] [PMID: 17304508]
[PMID: 14728590]
[http://dx.doi.org/10.1016/S0006-2952(00)00322-1] [PMID: 10856425]
[http://dx.doi.org/10.1186/bcr752] [PMID: 14979919]
[http://dx.doi.org/10.1080/004982598239155] [PMID: 9741952]
[http://dx.doi.org/10.1016/S0300-483X(02)00615-7] [PMID: 12604171]
[PMID: 15302093]
[http://dx.doi.org/10.1201/b11872-7]
[http://dx.doi.org/10.1016/0891-5849(95)02227-9] [PMID: 8743980]
[http://dx.doi.org/10.2174/09298673113209990141] [PMID: 23834166]
[http://dx.doi.org/10.1007/s11101-009-9142-8]
[http://dx.doi.org/10.1006/jcrs.1996.0090]
[http://dx.doi.org/10.1021/jf050579q] [PMID: 16159191]
[http://dx.doi.org/10.1016/j.foodchem.2005.06.030]
[http://dx.doi.org/10.1016/j.btre.2014.09.002] [PMID: 28626667]
[http://dx.doi.org/10.1021/jf011348w] [PMID: 11902973]
[http://dx.doi.org/10.1021/jf970055t]
[http://dx.doi.org/10.1271/bbb.56.324]
[http://dx.doi.org/10.1007/s00592-003-0099-6] [PMID: 14605967]
[http://dx.doi.org/10.1002/ptr.1440] [PMID: 15162367]
[http://dx.doi.org/10.1002/biof.552210161] [PMID: 15630218]
[http://dx.doi.org/10.1358/mf.2008.30.2.1143090] [PMID: 18560627]
[http://dx.doi.org/10.3858/emm.2011.43.12.078] [PMID: 21975281]
[http://dx.doi.org/10.1093/ndt/16.suppl_1.60] [PMID: 11369823]
[http://dx.doi.org/10.1161/01.HYP.27.1.32] [PMID: 8591884]
[http://dx.doi.org/10.1016/S0895-7061(01)02337-8] [PMID: 11991222]
[http://dx.doi.org/10.1055/s-2006-960005] [PMID: 1648246]
[http://dx.doi.org/10.1080/15376520500194783] [PMID: 20021059]
[http://dx.doi.org/10.1016/j.nrl.2012.10.006] [PMID: 23246214]
[http://dx.doi.org/10.1248/bpb.27.120] [PMID: 14709913]
[http://dx.doi.org/10.1038/sj.bjp.0704047] [PMID: 11325798]
[http://dx.doi.org/10.1111/j.1471-4159.2004.02899.x] [PMID: 15686476]
[http://dx.doi.org/10.1016/j.neuint.2005.11.006] [PMID: 16386335]
[http://dx.doi.org/10.1016/j.jpba.2004.04.008] [PMID: 15336368]
[http://dx.doi.org/10.1016/S0378-5173(00)00358-6] [PMID: 10794925]
[http://dx.doi.org/10.1002/(SICI)1097-0010(19990301)79:3<476:AID-JSFA270>3.0.CO;2-L]
[http://dx.doi.org/10.1111/j.0022-202X.2005.23768.x] [PMID: 16185284]
[http://dx.doi.org/10.1093/carcin/bgg117] [PMID: 12869420]
[http://dx.doi.org/10.1111/j.1365-2036.2006.02754.x] [PMID: 16393303]
[http://dx.doi.org/10.1080/01635581.2011.538486] [PMID: 21500097]
[http://dx.doi.org/10.1021/jf050489l] [PMID: 16104781]
[http://dx.doi.org/10.1002/jcb.20281] [PMID: 15486966]