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The Info List - 8-Prenylnaringenin


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8-Prenylnaringenin (8-PN), also known as flavaprenin, (S)-8-dimethylallylnaringenin, hopein, or sophoraflavanone B, is a prenylflavonoid phytoestrogen. It is reported to be the most estrogenic phytoestrogen known.[1] The compound is equipotent at ERα and ERβ,[2] and acts as a full agonist of ERα.[3] Its effects are similar to those of estradiol, but it is considerably less potent in comparison.[2] 8-PN is found in hops (Humulus lupulus) and in beer, and is responsible for the estrogenic effects of the former.[2][4] It can be produced from isoxanthohumol in fungal cells cultures,[5] and by flora in the human intestine.[1][6]

Contents

1 Properties

1.1 Estrogenic

2 Chemistry 3 Etymology 4 References

Properties[edit] In an in vitro study, 8-PN and its synthesized derivatives of it demonstrated to have anticancer activity.[7] Estrogenic[edit] 8-PN was shown to preserve bone density[1] and has been demonstrated to reduce hot flashes.[1][8] 8-PN also induces the secretion of prolactin, and increases other estrogenic responses.[9] The compound binds to and activates ERα more times than it does to ERβ.[1][2][10] This prenylflavanoid has drawn interest in the study of hormone replacement therapy, and it is comparable to selective estrogen-receptor modulators.[11][12] In an in vivo study, 8-PN has activated proliferation of mammary cells.[9] At the concentration found in beer, it is unlikely to have an estrogenic effect in breast tissue.[13] Prenylflavonoids from hops, namely 8-PN, are common in herbal breast enlargement preparations.[14] Similarly to other estrogens, 8-PN induces the expression of the progesterone receptor in various tissues.[9] Luteinizing hormone (LH) and follicle stimulating hormone (FSH) are suppressed by 8-PN, indicating that it possesses antigonadotropic properties.[9] 8-PN adversely affects male sperm.[15] The role 8-PN plays in fertility requires further research. Chemistry[edit] The enzyme naringenin 8-dimethylallyltransferase uses dimethylallyl diphosphate and (−)-(2S)-naringenin to produce diphosphate and sophoraflavanone B (8-prenylnaringenin). The enzyme 8-dimethylallylnaringenin 2'-hydroxylase uses sophoraflavanone B (8-prenylnaringenin), NADPH, H+ and O2 to produce leachianone G, NADP+ and H2O. Synthesized derivatives of 8-PN are: 7,4′-di-O-methyl-8-prenylnaringenin; 7-O-pentyl-8-prenylnaringenin; 7,4′-Di-O-allyl-8-prenylnaringenin; 7,4′-Di-O-acetyl-8-prenylnaringenin; and 7,4′-Di-O-palmitoyl-8-prenylnaringenin.[7] 8-Neopentylnaringenin and 8-n-heptylnaringenin are synthetic derivatives of 8-PN.[16] Etymology[edit] There is another compound, 8-isopentenylnaringenin,[1] also known as sophoraflavanone B, from Sophora flavescens, that could properly be called 8-prenylnaringenin by scientific naming convention.[17] References[edit]

^ a b c d e f Keiler AM, Zierau O, Kretzschmar G (2013). "Hop extracts and hop substances in treatment of menopausal complaints". Planta Med. 79 (7): 576–9. doi:10.1055/s-0032-1328330. PMID 23512496.  ^ a b c d Hajirahimkhan A, Dietz BM, Bolton JL (2013). "Botanical modulation of menopausal symptoms: mechanisms of action?". Planta Med. 79 (7): 538–53. doi:10.1055/s-0032-1328187. PMC 3800090 . PMID 23408273.  ^ Green, Sarah E (2015), In Vitro Comparison of Estrogenic Activities of Popular Women’s Health Botanicals  ^ Nikolic, D; Li, Y; Chadwick, LR; Grubjesic, S; Schwab, P; Metz, P; Van Breemen, RB (2004). "Metabolism of 8-prenylnaringenin, a potent phytoestrogen from hops (Humulus lupulus), by human liver microsomes". Drug Metabolism and Disposition. 32 (2): 272–9. doi:10.1124/dmd.32.2.272. PMID 14744951.  ^ Fu, Ming-Liang; Wang, Wei; Chen, Feng; Dong, Ya-Chen; Liu, Xiao-jie; Ni, Hui; Chen, Qi-he (2011). "Production of 8-Prenylnaringenin from Isoxanthohumol through Biotransformation by Fungi Cells". Journal of Agricultural and Food Chemistry. 59 (13): 7419–26. doi:10.1021/jf2011722. PMID 21634799.  ^ Possemiers, S.; et al. (July 2006). "The Prenylflavonoid Isoxanthohumol from Hops (Humulus lupulus L.) Is Activated into the Potent Phytoestrogen 8-Prenylnaringenin In Vitro and in the Human Intestine". Journal of Nutrition. American Society for Nutrition. 136 (7): 1862–1867. PMID 16772450.  ^ a b Anioł, Mirosław (January 7, 2012). "Antiproliferative activity and synthesis of 8-prenylnaringenin derivatives by demethylation of 7-O- and 4′-O-substituted isoxanthohumols". Med Chem Res. 21: 4230–4238. doi:10.1007/s00044-011-9967-8. PMC 3474914 . PMID 23087590.  ^ Bowe, James (November 15, 2012). "The hop phytoestrogen, 8-prenylnaringenin, reverses the ovariectomy-induced rise in skin temperature in an animal model of menopausal hot flushes". Journal of Endocrinology. doi:10.1677/joe.1.06919. Retrieved 2013-04-07.  ^ a b c d Overk, CR; Guo, J; Chadwick, LR; Lantvit, DD; Minassi, A; Appendino, G; Chen, SN; Lankin, DC; Farnsworth, NR; Pauli, GF; Van Breemen, RB; Bolton, JL (2008). "In vivo estrogenic comparisons of Trifolium pratense (red clover) Humulus lupulus (hops), and the pure compounds isoxanthohumol and 8-prenylnaringenin". Chemico-biological interactions. 176 (1): 30–39. doi:10.1016/j.cbi.2008.06.005. PMC 2574795 . PMID 18619951.  ^ Overk, C. R.; et al. (August 2005). "Comparison of the In Vitro Estrogenic Activities of Compounds from Hops (Humulus lupulus) and Red Clover (Trifolium pratense)". J Agric Food Chem. 53 (16): 6246–6253. doi:10.1021/jf050448p. PMC 1815392 . PMID 16076101.  ^ Rad; Hümpel; Schaefer; Schoemaker; Schleuning; Cohen; Burggraaf (September 1, 2006). "Pharmacokinetics and systemic endocrine effects of the phyto-oestrogen 8-prenylnaringenin after single oral doses to postmenopausal women". British Journal of Clinical Pharmacology. 62 (3): 288–296. doi:10.1111/j.1365-2125.2006.02656.x. PMC 1885137 . PMID 16934044.  ^ Bowe (November 2006). "The hop phytoestrogen, 8-prenylnaringenin, reverses the ovariectomy-induced rise in skin temperature in an animal model of menopausal hot flushes". Journal of Endocrinology. 191: 399–405. doi:10.1677/joe.1.06919. PMC 1635969 . PMID 17088409.  ^ Bolca, Selin; Li, Jinghu; Nikolic, Dejan; Roche, Nathalie; Blondeel, Phillip; Possemiers, Sam; De Keukeleire, Denis; Bracke, Marc; Heyerick, Arne; Van Breemen, Richard B.; Depypere, Herman (2010). "Disposition of hop prenylflavonoids in human breast tissue". Molecular Nutrition & Food Research. 54: S284–94. doi:10.1002/mnfr.200900519. PMC 3856213 . PMID 20486208.  ^ S. R. Milligan; J. C. Kalita; V. Pocock; V. Van De Kauter; J. F. Stevens; M. L. Deinzer; H. Rong & D. De Keukeleire (December 2000). "The Endocrine Activities of 8-Prenylnaringenin and Related Hop (Humulus lupulus L.) Flavonoids". Journal of Clinical Endocrinology & Metabolism. 85 (12): 4912–4915. doi:10.1210/jcem.85.12.7168. PMID 11134162.  ^ "Environmental 'hormones' wreck sperm". BBC News. July 2, 2002. Retrieved 2013-06-26.  ^ Breen, L.; et al. (2009). "The effect of synthetic analogues of the phyto-oestrogen 8-prenylnaringenin on tail skin temperature in a rat hot flush model". The Physiological Society.  ^ Chadwick; Pauli; Farnsworth (July 1, 2005). "The pharmacognosy of Humulus lupulus L. (hops) with an emphasis on estrogenic properties". Phytomedicine. 13: 119–31. doi:10.1016/j.phymed.2004.07.006. PMC 1852439 . PMID 16360942. 

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 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

Estrogen receptor modulators

ER

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-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) 16α-Hydroxy-DHEA 16α-Hydroxyestrone 16α-Iodo-E2 16α-LE2 16β,17α-Epiestriol (16β-hydroxy-17α-estradiol) 17α-Estradiol (alfatradiol) 17α-Dihydroequilenin 17α-Dihydroequilin 17α-Epiestriol (16α-hydroxy-17α-estradiol) 17β-Dihydroequilenin 17β-Dihydroequilin 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 estrogens DHEA DHEA-S Epiestriol (16β-epiestriol, 16β-hydroxy-17β-estradiol) Epimestrol Equilenin Equilin

Equilin acetate Equilin benzoate

ERA-63 (ORG-37663) Esterified estrogens Estetrol Estradiol

Estradiol esters Lipoidal estradiol Polyestradiol phosphate

Estramustine Estramustine phosphate Estrapronicate Estrazinol Estriol

Estriol esters

Estrofurate Estromustine Estrone

Estrone esters Estrone methyl ether Estropipate

Etamestrol (eptamestrol) Ethinylestradiol

Ethinylestradiol 3-benzoate Ethinylestradiol sulfonate

Ethinylestriol Ethylestradiol Etynodiol Etynodiol diacetate Hexolame Hippulin Hydroxyestrone diacetate Lynestrenol 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 AC-186 Allenestrol Allenolic acid Benzestrol Bifluranol Bisdehydrodoisynolic acid Carbestrol D-15414 DCW234 Diarylpropionitrile Dienestrol

Dienestrol diacetate

Diethylstilbestrol

Diethylstilbestrol esters

Dimestrol (dianisylhexene) Doisynoestrol (fenocycline) Doisynolic acid Efavirenz 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) Mestilbol Methallenestril Methestrol Methestrol dipropionate Paroxypropione Pentafluranol Phenestrol Prinaberel (ERB-041, WAY-202041) Propylpyrazoletriol Quadrosilan SC-4289 SERBA-2 SKF-82,958 Terfluranol Triphenylbromoethylene Triphenylchloroethylene Triphenyliodoethylene Triphenylmethylethylene (triphenylpropene) WAY-166818 WAY-200070 WAY-214156

Unknown/unsorted: ERB-26 ERA-45 ERB-79

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, 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) Synthetic xenoestrogens (e.g., alkylphenols, bisphenols (e.g., BPA, BPF, BPS), DDT, parabens, PBBs, PHBA, phthalates, PCBs) Others (e.g., agnuside, rotundifuran)

Mixed (SERMs)

2-Phenylbenzofuran 2-Phenylbenzothiophene 4'-Hydroxynorendoxifen 27-Hydroxycholesterol Acefluranol Acolbifene Afimoxifene Anordiol Anordrin Arzoxifene Bazedoxifene Brilanestrant Broparestrol Elacestrant Chlorotrianisene Clomifene Clomifenoxide Cyclofenil D-15413 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 Nafoxidine Nitromifene Ormeloxifene Ospemifene Panomifene Pipendoxifene Raloxifene Spironolactone SS1010 Tamoxifen TAS-108 (SR-16234) Toremifene Trioxifene TZE-5323 Y-134 Zindoxifene Zuclomifene

Antagonists

(R,R)-THC 7β-Hydroxy-DHEA Chloroindazole Cytestrol acetate EM-800 Epitiostanol ERA-90 ERB-88 Fulvestrant (ICI-182780) Glyceollins (I, II, III, IV) ICI-164384 Mepitiostane Methylepitiostanol Methylpiperidinopyrazole MIBE Oxabicycloheptene sulfonate Phenytoin PHTPP Prochloraz RU-58668 SS1020 TAS-108 (SR-16234) ZB716 ZK-164015 ZK-191703

GPER

Agonists

2-Methoxyestradiol 7β-Hydroxyepiandrosterone Afimoxifene (4-hydroxytamoxifen) Atrazine Bisphenol A Daidzein DDT (p,p'-DDT, o',p'-DDE) Equol Estradiol Ethinylestradiol Fulvestrant (ICI-182780) G-1 Genistein GPER-L1 GPER-L2 Hydroxytyrosol Kepone Niacin Nicotinamide Nonylphenol Oleuropein PCBs (2,2',5'-PCB-4-OH) Propylpyrazoletriol Quercetin Raloxifene Resveratrol Tamoxifen Tectoridin Zearalanone Zearalenol Zearalenone Zeranol (zearalanol))

Antagonists

CCL18 Estriol G-15 G-36 MIBE

See also Receptor/signaling modulators Estrogens and antiestrogens Androgen receptor modulators Progesterone receptor modulators List of estrogens

v t e

Flavanones and their glycosides

Flavanones

Butin Eriodictyol Naringenin Pinocembrin

O-methylated flavanones

Alpinetin Hesperetin Homoeriodictyol Isosakuranetin Pinostrobin (Pinocembrin-7-methylether) Sakuranetin Sterubin

C-methylated flavanones

Poriol

Glycosides

Eriocitrin Neoeriocitrin Hesperidin Liquiritin Naringin (Narigenin 7-O-neohesperidoside) Narirutin (Naringenin 7-O-rutinoside) Poncirin Prunin (Naringenin-7-O-glucoside) Sakuranin

Acetylated

8-Prenylnaringenin Isoxanthohumol Sophoraflavanone G

Acetylated glycos

.