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3. Chemie Von Rotklee … DIPLOMARBEIT / DIPLOMA THESIS Titel der Diplomarbeit / Title of the Diploma Thesis „Neue Daten zur Chemie, Pharmakologie, Toxikologie und Klinik von Rotklee“ verfasst von / submitted b" Jasmin Jandera angestrebter akademischer %rad / in partial fulfilment of the re&uirements for the degree of 'agistra der Pharmazie ('ag.pharm)* +ien, ,-./ / 0ienna, ,-./ 1tudienkennzahl lt) 1tudienblatt2 / 3 445 degree programme code as it appears on the student record sheet2 1tudienrichtung lt) 1tudienblatt / Diplomstudium Pharmazie degree programme as it appears on the student record sheet2 6etreut von / 1upervisor2 3o) 7niv) Prof) 'ag) Dr) 8iselotte Krenn 2 Danksagung Mein Dank gilt zuerst Frau ao. Univ. Prof. Dr. Liselotte Krenn für die interessante Aufgabenstellung und die stets freundliche Betreuung bei einer Diplo arbeit. Au"erde #chte ich ich bei eine Mann und einer $ochter bedanken, die i er hinter ir stehen, ich unterstützen, und es ir er #glicht haben, ein &tudium zu beenden. Bei einen 'ltern #chte ich ich bedanken, dass sie ir ein &tudium er #glicht haben. Mein Dank gilt nicht zuletzt all (enen, die ich bei der Anfertigung der Di!lo arbeit it Rat und $at unterstützt und ich auf eine &tudien*eg begleitet haben. 3 4 Inhaltsverzeichnis +. EINLEITUNG ,................................................................................................. + -. MATERIAL UND METHODEN ,....................................................................... - .. CHEMIE VON ROT LEE ,................................................................................ ..+ /nhaltsstoffe ,........................................................................................... ..+.+ /soflavone ,..................................................................................... ..+.+.+ 0erteilung der /soflavone in der Pflanze,............................... 1 ..+.- &2uren ,........................................................................................... 1 ..+.. Pol3saccharide ,.............................................................................. 4 ..+.5 6therische 7le ,.............................................................................. 4 ..+.1 8eitere /nhaltsstoffe ,.................................................................... 4 ..- /soflavonkonzentrationen in 9ahrungserg2nzungsmitteln.............. ,...... 4 5. IN VITRO !TUDIEN ,...................................................................................... : 5.+ /n Vitro &tudien it $estsubstraten ,....................................................... : 5.- /n 0itro &tudien in ;ells3ste en ,............................................................ : 5.-.+ $estung an verschiedenen $umorzelllinien ,................................... : 5.-.- $estung an 9ervenzelllinien ,........................................................ +5 5.-.. $estung der antiinfla atorischen Aktivit2t................................. +< 5.-.5 $estung an $racheage*ebe ,......................................................... +: 5.-.1 $estung an =steoklasten und =steoblasten ,................................ +: 5.-.4 $estung an der Prostata ,.............................................................. +> 5.-.< $estung auf anti 3kotische 8irkung ,......................................... +> 5.. /n 0itro &tudien zur )eze!torbindung ,................................................. +> 5.5 /n 0itro &tudien zur Phar akokinetik ,.................................................. -. 5 1. IN VIVO !TUDIEN ,...................................................................................... -5 1.+ 8irkung auf den Uterus ,...................................................................... -5 1.- 8irkung auf das 'ndo etrium ,............................................................ -4 1.. 8irkung auf die Kei drüsen ,............................................................... -< 1.5 8irkung auf Brustge*ebe und Brustdrüsen ,........................................ -< 1.1 8irkung auf die Leber ,......................................................................... -: 1.4 8irkung auf die Prostata ,..................................................................... -> 1.< 8irkung auf die Lunge ,......................................................................... -> 1.: 8irkung auf den Knochenmetabolismus ,............................................. .? 1.> Analgetische 8irkung ,......................................................................... .: 1.+? 8irkung auf die 8undheilung ,........................................................... .> 1.++ 8irkung auf die @aut ,......................................................................... .> 1.+- 8irkung auf BlutglucoseA und Fett*erte ,........................................... 5? 1.+. Antiinfla atorische und antiangiogene 8irkung ,........................... 5? 1.+5 Phar akokinetische 8irkung ,............................................................ 5+ 1.+1 Übergangsraten von Ph3to#strogenen in Milch ,................................ 5. 4. LINISCHE !TUDIEN ,.................................................................................. 55 4.+ 8irkung bei enopausalen Besch*erden ,.......................................... 55 4.- 8irkung auf das Cedächtnis ,................................................................ 5: 4.. 8irkung auf Angst und depressive &3 !to e ,.................................... 5> 4.5 8irkung auf den Knochenstoff*echsel ,............................................... 1? 4.1 8irkung auf die Brust ,.......................................................................... 1? 4.4 8irkung auf Prostata und Leber ,.......................................................... 1? 4.< 8irkung auf das Li!idprofil ,.................................................................. 1+ 4.: 8irkung auf die /nsulinsensitivit2t ,...................................................... 1+ 4.> 8irkung auf das /CF D &3ste ,............................................................. 1- 6 4.+? 8irkung auf den @o oc3steinspiegel ,............................................... 1. 4.++ Phar akokinetische 8irkung ,............................................................ 15 4.+- Uner*ünschte Arznei ittel*irkungen ,.............................................. 15 <. IN !ILICO !TUDIE ,....................................................................................... 14 :. "U!AMMENFA!!UNG ,............................................................................... 1< >. !UMMAR$ ,................................................................................................. 1> +?. LITERATURVER"EICHNIS ,........................................................................... 4+ ++. A%%ILDUNG!VER"EICHNIS ,........................................................................ <+ +-. TA%ELLENVER"EICHNIS ,............................................................................. <. 7 8 Abk'rzungsverzeichnis 4& ;ellen Prostatastro azellen AhR Ar3lh3drocarbon )eze!tor A) Androgen )eze!tor AUC Area under the curve BaF BCL-Aassociated G Bcl- B ;ell L3 pho - BPH benigne Prostatah3per!lasie E. humaner Ko !le entfaktor . E'' konjugiertes equines 7strogen cAMIE $ranskri!tionsfaktor E=G E3clooF3genase E=G<RP E3tochro c =xidase Untereinheit <Aver*andtes Protein EIP E3tochro DAD Diodenarra3ADetektion D@'A Deh3droepiandrosteron DM&= Di eth3lsulfoFid DPD DeoF3!3ridinolin '- 7stradiol ')J 7strogen )eze!tor J ')K 7strogen )eze!tor K 'RK+L- extrazellul2re &ignal regulierende Kinase M FP F2kalpr2parate F&@ Follikel sti ulierendes @or on C=$ =Falacetat $ransa inase CP$ Cluta at P3ruvat $ransa inase @aAras Protoonkogen @E9 +AA ;ellen humane kortikale 9ervenzellen @DL high densit3 lipoprotein @'&C ;ellen enschliche 'ndo etrium &tro azellen @MCACoAA)eduktase @3droF3 eth3lglutar3lACoenz3 A )eduktase @PLC @ochleistungs-Flüssigkeits-Chro atographie @PLEAM& @PLC gekoppelt it Massenspektro eter @PLEAUV-M& @PLC it UV-&pektrosko!ie und M& hT')$ humane $elo erase reverse $ranskri!tase @&D @3droF3steroid Deh3drogenase /E1? halbmaxi ale he ende Konzentration /CF /nsulinAlike gro*th factor /CFBP /CF bindende Proteine /CFA+) /CFA+ )eze!tor /NOJ /nhibitor des 9uklear Faktor Kappa Beta Alpha /' internationale 'inheiten /KK /NO Kinase 9 /L /nterleukin i9=& induzierte &tickstoff onoxid &3nthase /)E be*2sserter )otklee KC K#rperge*icht LAPC- 5 ;ellen Prostatakarzino zellen LE Flüssigkeitschro atographie LD@ Lactatdeh3drogenase LDL lo* densit3 lipoprotein L9EaP ;ellen Prostatakrebs ;elllinie LPS Lipopol3saccharid MAPK Mitogen-aktivierte Proteinkinasen Kaskade MCFA< ;ellen enschliche Brustkrebszelllinie MMP-+4 Matrix Metalloproteinase +4 MPA MedroF3progesteronacetat M& Massenspektro etrie M$$ .AP5%1ADi eth3lthiazolA-A3lAQA-%1Adiphen3lA tetrazoliumbro id 9FANB 9uklear Faktor Kappa Beta 9/)E )otklee der $rockenstress ausgesetzt *ar 9= &tickstoff onoFid =DMA OADesmeth3langolensin =0G =variekto ie, die 'ntfernung einerLbeider 'ierst#cke !AAkt Antik#rper PAMPA parallel artificial e brane per eabilit3 assa3 PC-. ;ellen Prostatakrebs ;elllinie PC-+- ;ellen Phäochro oz3to von Ratten !A/CFA+) onoklonaler Antik#rper PPA)J PeroFiso Proliferator aktivierender )eze!tor J PPA)R PeroFiso Proliferator aktivierender )eze!tor R PR Progesteron )eze!tor PRE Progesteron responsive ele ent PSA Prostataspezifisches Antigen S) Chinon )eduktase Ras rat sarco a% Pro =nkogen Raf ra!idl3 accelerated fibrosarco a% Protein RA8 -45.< ;ellen leuk2 ische onoz3tische Mausmakrophagen RP reverse phase, Umkehrphase )$APCR reverse $ranskri!taseAPol3 erasen-Kettenreaktion
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