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ation in alzheimer s disease neural regeneration research 10 8 1181 5 doi 10 4103 1673 5374 162686 pmc 4590215 pmid 26487830 flavonoids linus pauling institute oregon state university november 2015 retrieved 26 january 2021 viola h wasowski c levi de stein m et al june 1995 apigenin a component of matricaria recutita flowers is a central benzodiazepine receptors ligand with anxiolytic effects planta medica 61 3 213 216 bibcode 1995plmed 61 213v doi 10 1055 s 2006 958058 issn 0032 0943 pmid 7617761 dekermendjian k kahnberg p witt mr et al 21 october 1999 structure activity relationships and molecular modeling analysis of flavonoids binding to the benzodiazepine site of the rat brain gaba a receptor complex journal of medicinal chemistry 42 21 4343 4350 doi 10 1021 jm991010h issn 0022 2623 pmid 10543878 avallone r zanoli p puia g et al 1 june 2000 pharmacological profile of apigenin a flavonoid isolated from matricaria chamomilla biochemical pharmacology 59 11 1387 1394 doi 10 1016 s0006 2952 00 00264 1 hdl 11380 1207274 issn 0006 2952 pmid 10751547 forkmann g january 1991 flavonoids as flower pigments the formation of the natural spectrum and its extension by genetic engineering plant breeding 106 1 1 26 bibcode 1991pbree 106 1f doi 10 1111 j 1439 0523 1991 tb00474 x issn 0179 9541 herrmann km january 1995 the shikimate pathway as an entry to aromatic secondary metabolism plant physiology 107 1 7 12 doi 10 1104 pp 107 1 7 pmc 161158 pmid 7870841 lee h kim bg kim m et al september 2015 biosynthesis of two flavones apigenin and genkwanin in escherichia coli journal of microbiology and biotechnology 25 9 1442 8 doi 10 4014 jmb 1503 03011 pmid 25975614 austin mb noel jp february 2003 the chalcone synthase superfamily of type iii polyketide synthases natural product reports 20 1 79 110 doi 10 1039 b100917f pmid 12636085 martens s forkmann g matern u et al september 2001 cloning of parsley flavone synthase i phytochemistry 58 1 43 6 bibcode 2001pchem 58 43m doi 10 1016 s0031 9422 01 00191 1 pmid 11524111 leonard e yan y lim kh et al december 2005 investigation of two distinct flavone synthases for plant specific flavone biosynthesis in saccharomyces cerevisiae applied and environmental microbiology 71 12 8241 8 bibcode 2005apenm 71 8241l doi 10 1128 aem 71 12 8241 8248 2005 pmc 1317445 pmid 16332809 ververidis filippos f trantas emmanouil douglas carl et al october 2007 biotechnology of flavonoids and other phenylpropanoid derived natural products part i chemical diversity impacts on plant biology and human health biotechnology journal 2 10 1214 34 doi 10 1002 biot 200700084 pmid 17935117 hădărugă di hădărugă ng 2023 flavones structure properties sources and food applications handbook of food bioactive ingredients pp 111 158 doi 10 1007 978 3 031 28109 9_4 isbn 978 3 031 28108 2 meyer h bolarinwa a wolfram g et al 2006 bioavailability of apigenin from apiin rich parsley in humans annals of nutrition metabolism 50 3 167 72 doi 10 1159 000090736 pmid 16407641 s2cid 8223136 usda database for the flavonoid content of selected foods release 3 2011 v t e flavones and their conjugates aglycones monohydroxyflavone 3 hydroxyflavone 6 hydroxyflavone dihydroxyflavones chrysin 4 7 dihydroxyflavone 7 8 dihydroxyflavone trihydroxyflavones apigenin baicalein galangin norwogonin 7 8 3 trihydroxyflavone 6 7 4 trihydroxyflavone tetrahydroxyflavones fisetin kaempferol isoscutellarein luteolin norartocarpetin scutellarein pentahydroxyflavones herbacetin morin quercetin nortangeretin 6 hydroxyluteolin norwightin hypolaetin tricetin o methylated flavones 4 7 dihydroxy 6 methoxyflavone acacetin alnetin artocarpetin chrysoeriol cirsilineol cirsiliol cirsimaritin diosmetin eupatilin genkwanin hispidulin nepetin nobiletin oroxylin a pratol salvigenin sinensetin tangeretin techtochrysin tricin wogonin zapotin glycosides of apigenin apiin apigetrin isovitexin rhoifolin saponarin schaftoside vicenin 2 vitexin of baicalein baicalin tetuin of hypolaetin hypolaetin 8 glucoside hypolaetin 8 glucuronide of luteolin cynaroside isoorientin orientin veronicastroside luteolin 7 o glucuronide giraldiin a and b nepitrin oroxindin scutellarin acetylated artocarpetin a artoindonesianin p sulfated glycosides theograndin i and ii polymers amentoflavone ochnaflavone drugs diosmin hidrosmin category v t e xenoestrogens phytoestrogens flavanones hesperetin liquiritigenin naringenin pinocembrin flavones acacetin 7 8 dihydroxyflavone mirificin prenylflavonoids 8 prenylnaringenin 6 prenylnaringenin 8 geranylnaringenin 6 8 diprenylnaringenin icaritin isoflavones biochanin a daidzein daidzin formononetin genistein genistin glycitein ononin prunetin puerarin tectorigenin isoflavanes equol s equol glabridin dihydrochalcones phloretin phlorizin isoflavenes glabrene coumestans coumestan coumestrol desmethylwedelolactone wedelolactone lignans enterodiol enterolactone flavonolignans silybin cinchonain ib flavonols quercetin others deoxymiroestrol miroestrol resveratrol α isosparteine mycoestrogens zearalanone zearalenone α zearalanol zeranol α zearalenol β zearalanol β zearalenol derivatives d penicillamine synthetic alkylphenols atrazine bha bisphenol a bisphenol f bisphenol s dde ddt dieldrin dioxins endosulfan enzacamene erythrosine heptachlor lindane methoxychlor nonylphenol parabens pbbs pcbs pentachlorophenol phba phthalates propyl gallate perfluorinated compound metalloestrogens aluminium antimony arsenite barium cadmium chromium cobalt copper lead mercury nickel selenite tin vanadate v t e purine receptor modulators receptor ligands p0 adenine agonists 8 aminoadenine adenine p1 adenosine agonists 2 1 hexynyl n methyladenosine 2 cl ib meca 2 chloroadenosine 2 meccpa 4 o β d glucosyl 9 o 6 deoxysaccharosyl olivil 5 n ethylcarboxamidoadenosine adenosine adp amp apadenoson atl 146e atp bay 60 6583 binodenoson capadenoson cgs 21680 cp 532 903 cv 1808 evodenoson gr 79236 heneca luf 5835 luf 5845 n 6 cyclopentyladenosine namodenoson neca neladenoson dalanate piclidenoson regadenoson sdz wag 994 selodenoson sonedenoson tecadenoson trabodenoson uk 432 097 yzg 331 antagonists 3 chlorostyrylcaffeine csc 7 methylxanthine 8 chlorotheophylline 8 phenyl 1 3 dipropylxanthine 8 phenyltheophylline acefylline aminophylline atl 444 azd 4635 bamifylline cafedrine caffeine caffeine citrate cartazolate cgh 2466 cgs 15943 choline theophyllinate ciforadenant cpx cvt 6883 dimethazan dmpx dpcpx dyphylline enprofylline etazolate etrumadenant fenethylline ibmx imaradenant inupadenant isam 140 isam r316 isovaleric acid istradefylline kf 26777 lu aa41063 lu aa47070 mre3008f20 mrs 1191 mrs 1220 mrs 1334 mrs 1523 mrs 1706 mrs 1754 mrs 3777 msx 2 msx 3 msx 4 muvadenant paraxanthine pentoxifylline preladenant propentofylline proxyphylline psb 10 psb 11 psb 36 psb 603 psb 788 psb 1115 psb 1901 reversine rolofylline sch 442 416 sch 58261 sipagladenant taminadenant theacrine theobromine theodrenaline theophylline tozadenant tracazolate vipadenant vuf 5574 zm 241 385 p2 nucleotide p2x atp tooltip adenosine triphosphate agonists 2 me satp α β me atp adenosine adp amp ap4a ap5a atp atpγs bzatp cibacron blue ctp d β γ me atp gtp ht amp ivermectin l β γ me atp mrs 2219 papet atp utp zinc antagonists 5 bdbd a 317491 a 438079 a 740003 a 804598 a 839977 af 353 az 10606120 az 11645373 bbg calcium calmidazolium chelerythrine copper emodin rheum officinale evans blue gefapixant gw 791343 hma ip5i isoppads jnj 47965567 kn 04 kn 62 magnesium mrs 2159 nf 023 nf 110 nf 157 nf 279 nf 449 opiranserin vvz 149 oxidized atp phenol red phenolphthalein ppads ppnds psb 12062 puerarin radix puerariae purotoxin 1 rb 2 ro 0437626 ro 51 ro 3 sodium ferulate angelica sinensis ligusticum wallichii suramin tc p 262 tetramethylpyrazine ligustrazine ligusticum wallichii tnp atp zinc p2y agonists 2 me sadp 2 me satp 2 thio utp 5 br udp 5 ome udp α β me atp adenosine adp adpβs ap3a ar c 67085mx atp atpγs ctp datp denufosol diquafosol idp itp ins 365 ins 37217 mrs 2365 mrs 2690 mrs 2693 mrs 2768 mrs 2957 mrs 4062 nf 546 papet atp psb 0474 psb 1114 udp udpβs udp galactose udp glucose udp n acetylglucosamine up3u utp utpγs antagonists 2 me samp a3p5ps ampαs ap4a ar c 66096 ar c 67085mx ar c 69931mx ar c 118925xx atp bzatp c1330 7 cangrelor clopidogrel elinogrel ip5i mrs 2179 mrs 2211 mrs 2279 mrs 2395 mrs 2500 mrs 2578 nf 157 nf 340 pit ppads prasugrel psb 0739 rb 2 regrelor suramin ticagrelor ticlopidine udp transporter blockers cnts tooltip concentrative nucleoside transporters 6 hydroxy 7 methoxyflavone adenosine dmethpmr estradiol kgo 2142 kgo 2173 methpmr phloridzin progesterone ents tooltip equilibrative nucleoside transporters barbiturates benzodiazepines cilostazol dilazep dipyridamole estradiol ethanol hexobendine nbmpr pentoxifylline progesterone propentofylline pmat tooltip plasma membrane monoamine transporter decynium 22 enzyme inhibitors xo tooltip xanthine oxidase allopurinol amflutizole benzbromarone caffeic acid cinnamaldehyde cinnamomum osmophloeum febuxostat myo inositol kaempferol myricetin niraxostat oxipurinol phytic acid pistacia integerrima propolis quercetin tisopurine topiroxostat others aminopterin azathioprine methotrexate mycophenolic acid pemetrexed pralatrexate many others others precursors adenine adenosine amp adp atp cytosine cytidine cmp cdp ctp guanine guanosine gmp gdp gtp hypoxanthine inosine imp idp itp ribose uracil uridine ump udp utp others chrysophanol rhubarb see also receptor signaling modulators v t e estrogen receptor modulators er tooltip estrogen receptor agonists steroidal 2 hydroxyestradiol 2 hydroxyestrone 3 methyl 19 methyleneandrosta 3 5 dien 17β ol 3α androstanediol 3α 5α dihydrolevonorgestrel 3β 5α dihydrolevonorgestrel 3α hydroxytibolone 3β hydroxytibolone 3β androstanediol 4 androstenediol 4 androstenedione 4 fluoroestradiol 4 hydroxyestradiol 4 hydroxyestrone 4 methoxyestradiol 4 methoxyestrone 5 androstenediol 7 oxo dhea 7α hydroxy dhea 7α methylestradiol 7β hydroxyepiandrosterone 8 9 dehydroestradiol 8 9 dehydroestrone 8β ve2 10β 17β dihydroxyestra 1 4 dien 3 one dhed 11β chloromethylestradiol 11β methoxyestradiol 15α hydroxyestradiol 16 ketoestradiol 16 ketoestrone 16α fluoroestradiol 16α hydroxy dhea 16α hydroxyestrone 16α iodoestradiol 16α le2 16β hydroxyestrone 16β 17α epiestriol 16β hydroxy 17α estradiol 17α estradiol alfatradiol 17α dihydroequilenin 17α dihydroequilin 17α epiestriol 16α hydroxy 17α estradiol 17α ethynyl 3α androstanediol 17α ethynyl 3β androstanediol 17β dihydroequilenin 17β dihydroequilin 17β methyl 17α dihydroequilenin abiraterone abiraterone acetate alestramustine almestrone anabolic steroids e g testosterone and esters methyltestosterone metandienone methandrostenolone nandrolone and esters many others via estrogenic metabolites atrimustine bolandiol bolandiol dipropionate butolame clomestrone cloxestradiol cloxestradiol acetate conjugated estriol conjugated estrogens cyclodiol cyclotriol dhea dhea s ent estradiol epiestriol 16β epiestriol 16β hydroxy 17β estradiol epimestrol equilenin equilin era 63 org 37663 esterified estrogens estetrol estradiol estradiol esters lipoidal estradiol polyestradiol phosphate estramustine estramustine phosphate estrapronicate estrazinol estriol estriol esters polyestriol phosphate estrofurate estrogenic substances estromustine estrone estrone esters estrone methyl ether estropipate etamestrol eptamestrol ethinylandrostenediol ethandrostate ethinylestradiol ethinylestradiol 3 benzoate ethinylestradiol sulfonate ethinylestriol ethylestradiol etynodiol etynodiol diacetate hexolame hippulin hydroxyestrone diacetate lynestrenol lynestrenol phenylpropionate mestranol methylestradiol moxestrol mytatrienediol nilestriol norethisterone noretynodrel orestrate pentolame prodiame prolame promestriene ru 16117 quinestradol quinestrol tibolone nonsteroidal r r thc s s thc 2 8 dhhhc β lgnd1 β lgnd2 gtx 878 ac 186 allenestrol allenolic acid benzestrol bifluranol bisdehydrodoisynolic acid butestrol carbestrol d 15414 dcw234 diarylpropionitrile dienestrol dienestrol diacetate diethylstilbestrol diethylstilbestrol esters dimestrol dianisylhexene dimethylstilbestrol doisynoestrol fenocycline doisynolic acid efavirenz elacestrant erb 196 way 202196 erteberel serba 1 ly 500307 estrobin dbe fenestrel ferb 033 fosfestrol diethylstilbestrol diphosphate furostilbestrol diethylstilbestrol difuroate gtx 758 hexestrol hexestrol esters ici 85966 stilbostat m2613 meso butestrol meso hexestrol mestilbol methallenestril methestrol methestrol dipropionate osu erβ 12 paroxypropione pentafluranol phenestrol prinaberel erb 041 way 202041 propylpyrazoletriol quadrosilan sc 3296 sc 4289 serba 2 skf 82 958 terfluranol triphenylbromoethylene triphenylchloroethylene triphenyliodoethylene triphenylmethylethylene triphenylpropene way 166818 way 169916 way 200070 way 204688 sim 688 way 214156 unknown unsorted erb 26 era 45 erb 79 zk 283197 xenoestrogens anise related e g anethole anol dianethole dianol photoanethole chalconoids e g isoliquiritigenin phloretin phlorizin phloridzin wedelolactone coumestans e g coumestrol psoralidin flavonoids incl 7 8 dhf 8 prenylnaringenin apigenin baicalein baicalin biochanin a calycosin catechin daidzein daidzin ecg egcg epicatechin equol formononetin glabrene glabridin genistein genistin glycitein kaempferol liquiritigenin mirificin myricetin naringenin penduletin pinocembrin prunetin puerarin quercetin tectoridin tectorigenin lavender oil lignans e g enterodiol enterolactone nyasol cis hinokiresinol metalloestrogens e g cadmium pesticides e g alternariol dieldrin endosulfan fenarimol hpte methiocarb methoxychlor triclocarban triclosan phytosteroids e g digitoxin digitalis diosgenin guggulsterone phytosterols e g β sitosterol campesterol stigmasterol resorcylic acid lactones e g zearalanone α zearalenol β zearalenol zearalenone zeranol α zearalanol taleranol teranol β zearalanol steroid like e g deoxymiroestrol miroestrol stilbenoids e g resveratrol rhaponticin synthetic xenoestrogens e g alkylphenols bisphenols e g bpa bpf bps ddt parabens pbbs phba phthalates pcbs others e g agnuside rotundifuran mixed serms tooltip selective estrogen receptor modulators 2 phenylbenzofuran 2 phenyl 1 benzothiophene 4 hydroxynorendoxifen 27 hydroxycholesterol acefluranol acolbifene afimoxifene anordiol anordrin arzoxifene bazedoxifene brilanestrant broparestrol camizestrant chlorotrianisene clomifene clomifenoxide cn 55945 27 cyclofenil d 15413 desmethylchlorotrianisene droloxifene enclomifene endoxifen etacstil gw 5638 dpc 974 ethamoxytriphetol mer 25 femarelle fispemifene gw 7604 ici 55548 idoxifene lasofoxifene levormeloxifene ln 1643 ln 2299 ly 117018 menerba miproxifene miproxifene phosphate mrl 37 nafoxidine nitromifene nnc 45 0095 nnc 45 0320 nnc 45 0781 nnc 45 1506 ormeloxifene ospemifene panomifene pipendoxifene promensil raloxifene rimostil p 081 spironolactone ss1010 tamoxifen tas 108 sr 16234 toremifene trioxifene tze 5323 u 11555a u ...
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