啤酒花的化学成分及药理作用研究进展

5212009,Vol.30,No.23(830046)ChemicalCompositionandPharmacologicalEffectsofHops:AReviewLIUYu-mei(CollegeofChemistryandChemicalEngineering,XinjiangUniversity,Urmuqi830046,China)AbstractThehopplant(Humuluslupulus),commonlyusedinbrewing,isavigorousclimbingherbaceousperennial,usuallygrownupstringsinHopfieldandhopgarden.Somemembersofthisfamilyarewell-knownfortheircontentofpharmacologi-callyactiveresins,polyphenols(suchasxanthohumolandisoxanthohumol)andtheessentialoil.Inadditiontobrewing,recentstudieshaveshownbiologicalactivitiesofhopsextractagainstcancer,antivirusandininhibitingboneresorptionaswellaslipidperoxidation.Hopshavealsobeenusedasatraditionalherbwithsedative,hypnotic,antispasmodic,stomachic,tonic,diureticandtopicalbactericidalproperties.Thechemicalcompositioninhopsandtheirpharmacologicaleffectsarereviewedinthispapersoastopresentsomesightsforfurtherapplicationresearchanddevelopment.KeywordshopchemicalcompositionpharmacologicaleffectsTS261A1002-6630(2009)23-0521-072008-12-11(200991247)(1965)[e-mail].[1]3555[2-3][4]1213()[5-7]1/5--[8]2009,Vol.30,No.235221(%)(%)10263550-21800.1-110240.550.525()21002122471213()510Table1Chemicalcompositionofdriedhopcones-5-3-4-[11-12]2--(%)34345.08.0--1.01.02.01.82.52.0-28%30%20%45%20%40%2.52.510%5%SAAZspaltHallertauGoldClusterNorthernGalenaTettnangercrystalWillametteBrewingTargetfuggleMountHoodTable2Classificationandcharacterizationofhops.[13]1-3-[14-15]---0.7--1.6--2-Fig.1Light-crackingreactionHOOOOOHRhvSHSH---3--2------Fig.2ChemicalstructuresofacidanditsderivatesOOROHOHO-OOROHHOO-BH4H2Pd/COOHOHHOO-BH4H2Pd/COOHOHHOHO--OOHHOOOHRROOHHOHO--ROOHHOOHOHBH4BH4OOHHOOHOOHROOROHHOHOH--R=-CH2CH(CH3)2()R=-CH(CH3)2()R=-CH(CH3)CH2CH3(2--)R=-CH2CH3()R=-CH2CH2CH(CH3)2()HR5232009,Vol.30,No.23--5395%[16]----3Fig.3Chemicalstructureof-acidanditsderivatesOOHROO-OROOH2Pd/C(hulupones)OOROOH--R=-CH2CH(CH3)2()R=-CH(CH3)2()R=-CH(CH3)CH2CH3(2--)R=-CH2CH3()R=-CH2CH2CH(CH3)2()75%[17-18]4Fig.4Structuresofsomecompoundsinhopsessentialoil-----422-3-[19]8-[20-21]513[22][23]2.1[24-26]Fig.5ChemicalstructuresofpolyphenolsinhopsOMeHOOOHOOOHOHOMeHOOOOHOHOO8HO6OHOMeOOHOHOOHOHHOOHOOHHOOHOHOOHOOMeOHOHOOOHHO682,4,6,4-Terahydroxy-3-prenylchalconeDehydrocycloxanthohumolIsoxanthohumolXanthohumolDehydrocycloxanthohumolhydrateOH6-Prenylnaringenin8-Prenylnaringenin5-Prenylxanthohumol2,4,6,4-Terahydroxy-3-geranylchalconeOMeOHOH2009,Vol.30,No.2352411()()()[27]Tagashira[28](pH=47)20119[29]----2(COX-2)[30]15g[31]--2.2(MCF-7)(HT-9)(A-2780)0.1100mol/LDNA[32]P-450[33][34]B-B-[35](12-O-tetradecanoylphorbol-13-acetateTPA)[36]()[37-39]D3D3[40]2.3[41-43]LOXB3()2.4[44]Keiji-II[45](PPARs)(PPARs)3PPAR-PPAR-/PPAR---PPAR-PPAR-KK-Ay-C57BL/6N--II-8-A1c[46]-[47]5252009,Vol.30,No.232.5[48][49-50][51]2.6DNARNA[52-53]-HSV-1HSV-2Frolich[54]2.7[55-58]2--3--2-2.8[59-64]8-[1].:[M].:,1996:770-771.[2]VERZELEM,deKEUKELEIRED.Chemistryandanalysisofhopandbeerbitters[M].Amsterdam,Netherlands:ElsevierSciencePublishersBV,1991:1-3.[3].[M].,.:,1991:85-90.[4]BENITEZJL,FORSTERA,KEUKELEIRED.Hopsandhopproducts,manualofgoodpractice[M].Amsterdam,Netherlands:EBCandVerlagHansCarl,1997.[5]NEWALLCA.HerbalMedicines:Aguideforhealthcareprofessionals[M].London:ThePharmaceuticalPress,1996:162-163.[6]SHIPPEB,MEHIGHCS,HELFERICHWG.Theeffectofcolupulone(ahops-acid)onhepaticcytochromeP-450enzymaticactivityintherat[J].FoodandChemicalToxicology,1994,32:1007-1014.[7]YASUKAWAK,TAKEUCHIM,TAKIDOM.Humulone,abitterinthehop,inhibitstumorpromotionby12-O-tetradecanoylphorbol-13-acetateintwo-stagecarcinogenesisinmouseskin[J].Oncology,1995,52(2):156-158.[8]ONOM,KAKUDOY,YAMAMOTOY,etal.Quantitativeanalysisofhopbitteringcomponentsanditsapplicationtohopevaluation[J].Jour-nalAmericanSocietyBrewingChemical,1984,42:167-172.[9]LEWISMJ,YOUNGTW.Brewing[M].London:ChapmanandHall,1996:120-146.[10]IANSH.Brewing[M].London:theRoyalSocietyofChemistry,1999:59-84.[11]DARBYP.Acenturyofhopbreeding[M].England:PaulsandWhites,..2009,Vol.30,No.235261998:24-56.[12]MOIRM.Hops:amillenniumreview[J].JournalAmericanSocietyBrewingChemica,2000,58(4):131-146.[13]WEISSA,SCHOENBERGERC,MITTERW,etal.Sensoryandanalyticalcharacterizationofreduced,isomerisedhopextractsandtheirinfluenceanduseinbeer[J].JournaloftheInstituteofBrewing,2002,108(2):236-242[14]WILSONRJH,ROBERTST,SMITHRJ,etal.Improvinghoputilizationandflavourcontrolthroughtheuseofpre-isomerizedproductsinthebrewerykettle[J].TechnicalQuarterly,2001,38(1):11-21.[15]deCOOMANL,AERTSG,WITTERSA,etal.Comparativestudyofthestabilityofiso-alpha-acids,dihydroiso-alpha-acidsandtetrahydroiso-alpha-acidsduringbeerageing[J].Cerevisiae-BelgianJournalofBrew-ingandBiotechnology,2001,26(3):155-160.[16]VENTL,VENTJ.Groupsofhopvarietiesandtheirutilizationinbrewingindustry[J].KvasPrum,1999,45:335-337.[17]KOVACEVICM,KACM.Determinationandverificationofhopvari-etiesbyanalysisofessentialoils[J].FoodChemistry,2002,77:489-494.[18]KOVACEVICM,KACM.Solid-phasemicroextractionofhopvolatilespotentialusefordeterminationandverificationofhopvarieties[J].Jour-nalofChromatographyA,2001