Equol

Equol (4′,7-Isoflavandiol) ist ein Isoflavandiol¹The structures of 7,4’-dihydroxy-isoflavan and its precursors is shown in Structural Elucidation of Hydroxylated Metabolites of the Isoflavan Equol by GC/MS and HPLC/MS by Corinna E. Rüfer, Hansruedi Glatt, and Sabine E. Kulling in Drug Metabolism and Disposition (2005, electronic publication). -Östrogen, das von der Bakterienflora im Darm aus Daidzein, einer Art Isoflavon, das in Sojabohnen und anderen pflanzlichen Quellen vorkommt, verstoffwechselt wird.²Wang XL, Hur HG, Lee JH, Kim KT, Kim SI (January 2005). “Enantioselective synthesis of S-equol from dihydrodaidzein by a newly isolated anaerobic human intestinal bacterium”. Appl. Environ. Microbiol. 71 (1): 214–9. Bibcode:2005ApEnM..71..214W. doi:10.1128/AEM.71.1.214-219.2005. PMC 544246. PMID 15640190.³Muthyala, Rajeev S; Ju, Young H; Sheng, Shubin; Williams, Lee D; Doerge, Daniel R; Katzenellenbogen, Benita S; Helferich, William G; Katzenellenbogen, John A (2004). “Equol, a natural estrogenic metabolite from soy isoflavones”. Bioorganic & Medicinal Chemistry. 12 (6): 1559–1567. doi:10.1016/j.bmc.2003.11.035. ISSN 0968-0896. PMID 15018930. Während körpereigene östrogene Hormone wie Östradiol Steroide sind, ist Equol ein nichtsteroidales Östrogen. Nur etwa 30-50% der Menschen haben Darmbakterien, die Equol herstellen.⁴Frankenfeld CL, Atkinson C, Thomas WK, et al. (December 2005). “High concordance of daidzein-metabolizing phenotypes in individuals measured 1 to 3 years apart”. Br. J. Nutr. 94 (6): 873–6. doi:10.1079/bjn20051565. PMID 16351761.

Geschichte

(S)-Equol wurde erstmals 1932 aus Pferdeurin isoliert,⁵Marrian, GF; Haslewood, GA (1932). “Equol, a new inactive phenol isolated from the ketohydroxyoestrin fraction of mares’ urine”. The Biochemical Journal. 26 (4): 1227–32. doi:10.1042/bj0261227. PMC 1261026. PMID 16744928. und der Name wurde durch diese Verbindung zum Pferd vorgeschlagen.⁶Axelson, M; Kirk, DN; Farrant, RD; Cooley, G; Lawson, AM; Setchell, KD (1982-02-01). “The identification of the weak oestrogen equol [7-hydroxy-3-(4′-hydroxyphenyl)chroman] in human urine”. The Biochemical Journal. 201 (2): 353–7. doi:10.1042/bj2010353. PMC 1163650. PMID 7082293. Seitdem wurde Equol im Urin oder Plasma vieler anderer Tierarten gefunden, obwohl diese Tiere erhebliche Unterschiede in ihrer Fähigkeit haben, Daidzein in Equol zu verstoffwechseln. Im Jahr 1980 meldeten Wissenschaftler die Entdeckung von Equol beim Menschen.⁷Setchell, KD; Clerici, C (July 2010). “Equol: history, chemistry, and formation”. The Journal of Nutrition. 140 (7): 1355S–62S. doi:10.3945/jn.109.119776. PMC 2884333. PMID 20519412. Die Möglichkeit, dass (S)-Equol eine Rolle bei der Behandlung von östrogen- oder androgenvermittelten Krankheiten oder Störungen spielen könnte, wurde erstmals 1984 vorgeschlagen.⁸Setchell, KD; Borriello, SP; Hulme, P; Kirk, DN; Axelson, M (September 1984). “Nonsteroidal estrogens of dietary origin: possible roles in hormone-dependent disease”. The American Journal of Clinical Nutrition. 40 (3): 569–78. doi:10.1093/ajcn/40.3.569. PMID 6383008. S2CID 4467689.

Chemische Struktur

Equol ist eine Verbindung, die in zwei Formen vorkommen kann Enantiomeren existieren kann: (S)-Equol und (R)-Equol. (S)-Equol wird von Menschen und Tieren produziert, die in der Lage sind, das Soja-Isoflavon Daidzein zu verstoffwechseln, während (R)-Equol chemisch synthetisiert werden kann.⁹Marrian, GF; Haslewood, GA (1932). “Equol, a new inactive phenol isolated from the ketohydroxyoestrin fraction of mares’ urine”. The Biochemical Journal. 26 (4): 1227–32. doi:10.1042/bj0261227. PMC 1261026. PMID 16744928. Die molekulare und physikalische Struktur von (S)-Equol ähnelt der des Hormons Estradiol.¹⁰Atkinson, C; Frankenfeld, CL; Lampe, JW (March 2005). “Gut bacterial metabolism of the soy isoflavone daidzein: exploring the relevance to human health”. Experimental Biology and Medicine. 230 (3): 155–70. doi:10.1177/153537020523000302. PMID 15734719. S2CID 14112442. (S)-Equol bindet bevorzugt an den Östrogenrezeptor beta.¹¹Wang XL, Hur HG, Lee JH, Kim KT, Kim SI (January 2005). “Enantioselective synthesis of S-equol from dihydrodaidzein by a newly isolated anaerobic human intestinal bacterium”. Appl. Environ. Microbiol. 71 (1): 214–9. Bibcode:2005ApEnM..71..214W. doi:10.1128/AEM.71.1.214-219.2005. PMC 544246. PMID 15640190.¹²Mueller SO, Simon S, Chae K, Metzler M, Korach KS (April 2004). “Phytoestrogens and their human metabolites show distinct agonistic and antagonistic properties on estrogen receptor {α} (ER{α}) and ERβ in human cells”. Toxicol. Sci. 80 (1): 14–25. doi:10.1093/toxsci/kfh147. PMID 15084758.

Pharmakologie

Östrogenrezeptor-Bindung

(S)-Equol ist ein nichtsteroidaler, selektiver Agonist von ERβ (Ki = 16 nM) mit 13-facher Selektivität für ERβ gegenüber ERα.¹³Muthyala, Rajeev S; Ju, Young H; Sheng, Shubin; Williams, Lee D; Doerge, Daniel R; Katzenellenbogen, Benita S; Helferich, William G; Katzenellenbogen, John A (2004). “Equol, a natural estrogenic metabolite from soy isoflavones”. Bioorganic & Medicinal Chemistry. 12 (6): 1559–1567. doi:10.1016/j.bmc.2003.11.035. ISSN 0968-0896. PMID 15018930. Im Vergleich zu (S)-Equol ist (R)-Equol weniger stark und bindet an ERα (Ki = 50 nM) mit 3. 3 (S)-Equol hat etwa 2 % der Bindungsaffinität von Estradiol für den menschlichen Östrogenrezeptor alpha (ERα) und 20 % der Bindungsaffinität von Estradiol für den menschlichen Östrogenrezeptor beta (ERβ). Die bevorzugte Bindung von (S)-Equol an ERβ gegenüber ERα und im Vergleich zu Estradiol deutet darauf hin, dass das Molekül einige der Eigenschaften eines selektiven Östrogenrezeptormodulators (SERM) aufweist.¹⁴Setchell, KD; Clerici, C; Lephart, ED; Cole, SJ; Heenan, C; Castellani, D; Wolfe, BE; Nechemias-Zimmer, L; Brown, NM; Lund, TD; Handa, RJ; Heubi, JE (May 2005). “S-equol, a potent ligand for estrogen receptor beta, is the exclusive enantiomeric form of the soy isoflavone metabolite produced by human intestinal bacterial flora”. The American Journal of Clinical Nutrition. 81 (5): 1072–9. doi:10.1093/ajcn/81.5.1072. PMID 15883431. Equol wirkt als Agonist des GPER (GPR30).¹⁵Prossnitz, Eric R.; Barton, Matthias (2014). “Estrogen biology: New insights into GPER function and clinical opportunities”. Molecular and Cellular Endocrinology. 389 (1–2): 71–83. doi:10.1016/j.mce.2014.02.002. ISSN 0303-7207. PMC 4040308. PMID 24530924.

Pharmakokinetik

(S)-Equol ist ein sehr stabiles Molekül, das im Wesentlichen unverändert bleibt, wenn es verdaut wird, und dieser Mangel an weiterem Metabolismus erklärt seine sehr schnelle Absorption und hohe Bioverfügbarkeit.¹⁶Setchell, KD; Zhao, X; Jha, P; Heubi, JE; Brown, NM (Oct 2009). “The pharmacokinetic behavior of the soy isoflavone metabolite S-(-)equol and its diastereoisomer R-(+)equol in healthy adults determined by using stable-isotope-labeled tracers”. The American Journal of Clinical Nutrition. 90 (4): 1029–37. doi:10.3945/ajcn.2009.27981. PMC 2744624. PMID 19710188. Wenn (S)-Equol konsumiert wird, wird es schnell absorbiert und erreicht eine Tmax (Spitzenplasmakonzentration) in zwei bis drei Stunden. Im Vergleich dazu liegt die Tmax von Daidzein bei 4 bis 10 Stunden, weil Daidzein als Glykosid (mit einer Glukoseseitenkette) vorliegt. Der Körper muss Daidzein in seine Aglykonform (ohne die Glukoseseitenkette) umwandeln, indem er die Zuckerseitenkette während der Verdauung entfernt, bevor er Daidzein verwenden kann. Wenn Daidzein direkt in der Aglykonform verzehrt wird, liegt die Tmax bei ein bis drei Stunden.¹⁷Setchell, KD; Zhao, X; Shoaf, SE; Ragland, K (Nov 2009). “The pharmacokinetics of S-(-)equol administered as SE5-OH tablets to healthy postmenopausal women”. The Journal of Nutrition. 139 (11): 2037–43. doi:10.3945/jn.109.110874. PMID 19776178. Die prozentuale Ausscheidung von (S)-Equol im Urin nach oraler Einnahme ist hoch und kann bei manchen Erwachsenen fast 100 Prozent erreichen. Die prozentuale Ausscheidung von Daidzein ist mit 30 bis 40 Prozent viel geringer¹⁸Setchell, KD; Clerici, C (Jul 2010). “Equol: pharmacokinetics and biological actions”. The Journal of Nutrition. 140 (7): 1363S–8S. doi:10.3945/jn.109.119784. PMC 2884334. PMID 20519411..

Herstellung beim Menschen

Um nach dem Verzehr von Soja (S)-Equol zu produzieren, müssen bestimmte Bakterienstämme in den Därmen des Menschen leben.¹⁹Setchell, KD; Borriello, SP; Hulme, P; Kirk, DN; Axelson, M (September 1984). “Nonsteroidal estrogens of dietary origin: possible roles in hormone-dependent disease”. The American Journal of Clinical Nutrition. 40 (3): 569–78. doi:10.1093/ajcn/40.3.569. PMID 6383008. S2CID 4467689. Einundzwanzig verschiedene Darmbakterienstämme, die bei Menschen gezüchtet wurden, sind nachweislich in der Lage, Daidzein in (S)-Equol oder eine verwandte Zwischenverbindung umzuwandeln. ²⁰Setchell, KD; Clerici, C (July 2010). “Equol: history, chemistry, and formation”. The Journal of Nutrition. 140 (7): 1355S–62S. doi:10.3945/jn.109.119776. PMC 2884333. PMID 20519412. Mehrere Studien zeigen, dass nur 25 bis 30 Prozent der erwachsenen Bevölkerung in den westlichen Ländern nach dem Verzehr von isoflavonhaltigen Sojanahrungsmitteln (S)-Equol produzieren,²¹Setchell, KD; Clerici, C (July 2010). “Equol: history, chemistry, and formation”. The Journal of Nutrition. 140 (7): 1355S–62S. doi:10.3945/jn.109.119776. PMC 2884333. PMID 20519412.²²Setchell, KD; Clerici, C (July 2010). “Equol: history, chemistry, and formation”. The Journal of Nutrition. 140 (7): 1355S–62S. doi:10.3945/jn.109.119776. PMC 2884333. PMID 20519412.²³Setchell, KD; Cole, SJ (August 2006). “Method of defining equol-producer status and its frequency among vegetarians”. The Journal of Nutrition. 136 (8): 2188–93. doi:10.1093/jn/136.8.2188. PMID 16857839.²⁴Rowland, IR; Wiseman, H; Sanders, TA; Adlercreutz, H; Bowey, EA (2000). “Interindividual variation in metabolism of soy isoflavones and lignans: influence of habitual diet on equol production by the gut microflora”. Nutrition and Cancer. 36 (1): 27–32. doi:10.1207/S15327914NC3601_5. PMID 10798213. S2CID 10603402.während 50 bis 60 Prozent der Erwachsenen in Japan, Korea und China Equol produzieren.²⁵Watanabe, S; Yamaguchi, M; Sobue, T; Takahashi, T; Miura, T; Arai, Y; Mazur, W; Wähälä, K; Adlercreutz, H (October 1998). “Pharmacokinetics of soybean isoflavones in plasma, urine and feces of men after ingestion of 60 g baked soybean powder (kinako)”. The Journal of Nutrition. 128 (10): 1710–5. doi:10.1093/jn/128.10.1710. PMID 9772140.²⁶Arai, Y; Uehara, M; Sato, Y; Kimira, M; Eboshida, A; Adlercreutz, H; Watanabe, S (March 2000). “Comparison of isoflavones among dietary intake, plasma concentration and urinary excretion for accurate estimation of phytoestrogen intake”. Journal of Epidemiology. 10 (2): 127–35. doi:10.2188/jea.10.127. PMID 10778038.²⁷Akaza, H; Miyanaga, N; Takashima, N; Naito, S; Hirao, Y; Tsukamoto, T; Fujioka, T; Mori, M; Kim, WJ; Song, JM; Pantuck, AJ (February 2004). “Comparisons of percent equol producers between prostate cancer patients and controls: case-controlled studies of isoflavones in Japanese, Korean and American residents”. Japanese Journal of Clinical Oncology. 34 (2): 86–9. doi:10.1093/jjco/hyh015. PMID 15067102. ²⁸Song, KB; Atkinson, C; Frankenfeld, CL; Jokela, T; Wähälä, K; Thomas, WK; Lampe, JW (May 2006). “Prevalence of daidzein-metabolizing phenotypes differs between Caucasian and Korean American women and girls”. The Journal of Nutrition. 136 (5): 1347–51. doi:10.1093/jn/136.5.1347. PMID 16614428. Es wurde auch berichtet, dass Vegetarier eher in der Lage sind, Daidzein in (S)-Equol umzuwandeln.²⁹Patisaul, HB; Jefferson, W (October 2010). “The pros and cons of phytoestrogens”. Front Neuroendocrinol. 31 (4): 400–419. doi:10.1016/j.yfrne.2010.03.003. PMC 3074428. PMID 20347861. Der Verzehr von Algen und Milchprodukten kann die Produktion von Equol steigern.³⁰Atkinson, C; Frankenfeld, CL; Lampe, JW (March 2005). “Gut bacterial metabolism of the soy isoflavone daidzein: exploring the relevance to human health”. Experimental Biology and Medicine. 230 (3): 155–70. doi:10.1177/153537020523000302. PMID 15734719. S2CID 14112442.³¹Atkinson, C; Frankenfeld, CL; Lampe, JW (March 2005). “Gut bacterial metabolism of the soy isoflavone daidzein: exploring the relevance to human health”. Experimental Biology and Medicine. 230 (3): 155–70. doi:10.1177/153537020523000302. PMID 15734719. S2CID 14112442. Die Fähigkeit einer Person, (S)-Equol zu produzieren, wird bestimmt, indem Personen getestet werden, die mindestens einen Monat lang keine Antibiotika genommen haben. Für diesen standardisierten Test trinkt die Person drei Tage lang zwei 240-Milliliter-Gläser Sojamilch oder isst ein gleichwertiges Sojalebensmittel. Die (S)-Equol-Konzentration im Urin jeder Testperson wird am vierten Tag bestimmt.³²Setchell, KD; Cole, SJ (August 2006). “Method of defining equol-producer status and its frequency among vegetarians”. The Journal of Nutrition. 136 (8): 2188–93. doi:10.1093/jn/136.8.2188. PMID 16857839.

Equol produzierende Bakterien

Zwar sind noch viele weitere Bakterien an dem damit zusammenhängenden Zwischenprozess der Equolproduktion beteiligt, z. B. an der Umwandlung von Daidzin in Daidzein oder von Genistein in 5-Hydroxy-Equol, aber zu den Bakterien, die die vollständige Umwandlung von Daidzein in (S)-Equol erreichen,³³Setchell KD, Clerici C, Lephart ED, Cole SJ, Heenan C, Castellani D, Wolfe BE, Nechemias-Zimmer L, Brown NM, Lund TD, Handa RJ, Heubi JE (2005). “S-equol, a potent ligand for estrogen receptor beta, is the exclusive enantiomeric form of the soy isoflavone metabolite produced by human intestinal bacterial flora”. Am. J. Clin. Nutr. 81 (5): 1072–9. doi:10.1093/ajcn/81.5.1072. PMID 15883431. gehören:³⁴Setchell, K. D.; Clerici, C. (2010). “Equol: History, Chemistry, and Formation”. The Journal of Nutrition. 140 (7): 1355S–1362S. doi:10.3945/jn.109.119776. PMC 2884333. PMID 20519412.

Adlercreutzia equolifaciens
Asaccharobacter celatus AHU1763
Bacteroides ovatus
Bifidobacterium
Bifidobacterium animalis
Coriobacteriaceae sp MT1B9
Eggerthella sp YY7918
Enterococcus faecium
Eubacterium sp D1 und D2
Finegoldia magna
Lactobacillus mucosae
Lactobacillus sp Niu-O16
Lactococcus garvieae (Lc 20-92)
Ruminococcus productus
Slackia sp HE8
Slackia equolifaciens (Stamm DZE)
Streptococcus intermedius
Veillonella sp

Die Umwandlung durch Bifidobacterium wurde nur einmal von Tsangalis et al. im Jahr 2002³⁵V, Ravishankar Rai; Bai, Jamuna A. (2014-12-17). Beneficial Microbes in Fermented and Functional Foods. CRC Press. ISBN 978-1-4822-0663-0. beschrieben und seitdem nicht mehr reproduziert.Bifidobakterien: Genomics and Molecular Aspects Mischkulturen wie Lactobacillus sp. Niu-O16 und Eggerthella sp. Julong 732 können ebenfalls (S)-Equol produzieren.Bifidobakterien: Genomics and Molecular Aspects Einige equolproduzierende Bakterien sind, wie ihre Nomenklatur andeutet, Adlercreutzia equolifaciens, Slackia equolifaciens und Slackia isoflavoniconvertens.

Gesundheitliche Auswirkungen

Gesundheit der Haut

Die topischen Wirkungen von Equol als Anti-Aging-Substanz sind in verschiedenen Studien nachgewiesen worden. Die Wirkungen resultieren sowohl aus molekularen als auch aus strukturellen Veränderungen der Haut. Equol kann z.B. zu einer Verlängerung der Telomere führen. Als Antioxidans kann Equol den Alterungsprozess verlangsamen, indem es die durch reaktive Sauerstoffspezies (ROS) verursachten Schäden reduziert. Es kann auch als schützende Anti-Photoaging-Substanz wirken, indem es die akute UVA-induzierte Lipidperoxidation hemmt.³⁶Reeve V, Widyarini S, Domanski D, Chew K, Barnes K. Protection Against Photoaging in the Hairless Mouse by the Isoflavone Equol. Photochemistry and Photobiology, Volume 81, Issue 6, November 2005, Pages 1548-1553 Darüber hinaus kann Equol einen positiven Einfluss auf die epigenetische Regulierung haben.³⁷Magnet, U.; Urbanek, C.; Gaisberger, D.; Tomeva, E.; Dum, E.; Pointner, A.; Haslberger, A.G. (October 2017). “Topical equol preparation improves structural and molecular skin parameters”. International Journal of Cosmetic Science. 39 (5): 535–542. doi:10.1111/ics.12408. PMID 28574180. S2CID 44910993. Die phytoöstrogenen Eigenschaften von Equol können sich auch auf die Hautgesundheit auswirken.³⁸Lephart ED (November 2016). “Skin aging and oxidative stress: Equol’s anti-aging effects via biochemical and molecular mechanisms”. Ageing Research Reviews. 31: 36–54. doi:10.1016/j.arr.2016.08.001. PMID 27521253. S2CID 205668316. Es wurde über eine Verringerung von Augenringen und -falten nach einer Behandlung mit Equol berichtet.³⁹Lephart ED (November 2016). “Skin aging and oxidative stress: Equol’s anti-aging effects via biochemical and molecular mechanisms”. Ageing Research Reviews. 31: 36–54. doi:10.1016/j.arr.2016.08.001. PMID 27521253. S2CID 205668316. Equol kann die Haut aufgrund seiner antioxidativen und entzündungshemmenden Eigenschaften auch vor Schäden durch Umweltverschmutzung schützen.⁴⁰Lephart, Edwin (2018-01-29). “Equol’s Anti-Aging Effects Protect against Environmental Assaults by Increasing Skin Antioxidant Defense and ECM Proteins While Decreasing Oxidative Stress and Inflammation”. Cosmetics. 5 (1): 16. doi:10.3390/cosmetics5010016. ISSN 2079-9284.

Jedes der Enantiomere und das racemische Gemisch beider Enantiomere haben unterschiedliche Eigenschaften, Bioverfügbarkeiten und molekulare Wirkungen.⁴¹Lephart, Edwin D. (November 2013). “Protective effects of equol and their polyphenolic isomers against dermal aging: Microarray/protein evidence with clinical implications and unique delivery into human skin”. Pharmaceutical Biology. 51 (11): 1393–1400. doi:10.3109/13880209.2013.793720. ISSN 1388-0209. PMID 23862588. Einer Studie zufolge brachte (RS)-Equol die größte Gesamtverbesserung der Hautgesundheit, insbesondere bei topischer Anwendung.

Hormonbedingte Gesundheitseffekte

Neben den topischen Wirkungen hat sich gezeigt, dass (RS)-Equol Wechseljahrsbeschwerden wie Hitzewallungen sowie Muskel- und Gelenkschmerzen lindert.⁴²Lephart, Edwin D. (November 2013). “Protective effects of equol and their polyphenolic isomers against dermal aging: Microarray/protein evidence with clinical implications and unique delivery into human skin”. Pharmaceutical Biology. 51 (11): 1393–1400. doi:10.3109/13880209.2013.793720. ISSN 1388-0209. PMID 23862588.⁴³Effect of natural S-equol on bone metabolism in equol non-producing postmenopausal Japanese women: a pilot randomized placebo-controlled trial. Tomomi Ueno of Saga Nutraceutricals Research Institute, Otsuka Pharmaceutical Co., Ltd., Japan, et.al Es wurde auch berichtet, dass (RS)-Equol die mit der vaginalen Atrophie der Wechseljahre verbundenen Symptome wie vaginalen Juckreiz, vaginale Trockenheit und Schmerzen beim Geschlechtsverkehr reduziert und positive Veränderungen der vaginalen Bakterienpopulation, der Zellzusammensetzung und des pH-Werts bewirkt.⁴⁴Mayr, Linda; Georgiev, Dimitar; Toulev, Albena (2019-03-01). “Eine Proof-of-concept-Studie von Isoflavandiol-E55-RS-Vaginalkapseln oder Vaginalgel zur Linderung der menopausalen Vaginalatrophie”. Journal für Gynäkologische Endokrinologie/Österreich (in German). 29 (1): 13–22. doi:10.1007/s41974-019-0085-9. ISSN 1996-1553.

Tierversuchen zufolge⁴⁵“Equol Is a Novel Anti-Androgen that Inhibits Prostate Growth and Hormone Feedback, Biology of Reproduction, Volume 70, Issue 4, 1 April 2004, Pages 1188–1195,”. academic.oup.com. Retrieved 2023-11-17. hat es antiandrogene Wirkungen und kann zu einer Hemmung der 5-alpha-Reduktase sowie zu einer Senkung des Dihydrotestosteronspiegels (DHT) führen.

Siehe auch

Daidzein
Östrogenrezeptor
Genistein
Liquiritigenin
Menerba
Prinaberel
WAY-200070
Diarylpropionitril

Quellenangaben

Quellen und Tiefen

• 1
  The structures of 7,4’-dihydroxy-isoflavan and its precursors is shown in Structural Elucidation of Hydroxylated Metabolites of the Isoflavan Equol by GC/MS and HPLC/MS by Corinna E. Rüfer, Hansruedi Glatt, and Sabine E. Kulling in Drug Metabolism and Disposition (2005, electronic publication).
• 2
  Wang XL, Hur HG, Lee JH, Kim KT, Kim SI (January 2005). “Enantioselective synthesis of S-equol from dihydrodaidzein by a newly isolated anaerobic human intestinal bacterium”. Appl. Environ. Microbiol. 71 (1): 214–9. Bibcode:2005ApEnM..71..214W. doi:10.1128/AEM.71.1.214-219.2005. PMC 544246. PMID 15640190.
• 3
  Muthyala, Rajeev S; Ju, Young H; Sheng, Shubin; Williams, Lee D; Doerge, Daniel R; Katzenellenbogen, Benita S; Helferich, William G; Katzenellenbogen, John A (2004). “Equol, a natural estrogenic metabolite from soy isoflavones”. Bioorganic & Medicinal Chemistry. 12 (6): 1559–1567. doi:10.1016/j.bmc.2003.11.035. ISSN 0968-0896. PMID 15018930.
• 4
  Frankenfeld CL, Atkinson C, Thomas WK, et al. (December 2005). “High concordance of daidzein-metabolizing phenotypes in individuals measured 1 to 3 years apart”. Br. J. Nutr. 94 (6): 873–6. doi:10.1079/bjn20051565. PMID 16351761.
• 5
  Marrian, GF; Haslewood, GA (1932). “Equol, a new inactive phenol isolated from the ketohydroxyoestrin fraction of mares’ urine”. The Biochemical Journal. 26 (4): 1227–32. doi:10.1042/bj0261227. PMC 1261026. PMID 16744928.
• 6
  Axelson, M; Kirk, DN; Farrant, RD; Cooley, G; Lawson, AM; Setchell, KD (1982-02-01). “The identification of the weak oestrogen equol [7-hydroxy-3-(4′-hydroxyphenyl)chroman] in human urine”. The Biochemical Journal. 201 (2): 353–7. doi:10.1042/bj2010353. PMC 1163650. PMID 7082293.
• 7
  Setchell, KD; Clerici, C (July 2010). “Equol: history, chemistry, and formation”. The Journal of Nutrition. 140 (7): 1355S–62S. doi:10.3945/jn.109.119776. PMC 2884333. PMID 20519412.
• 8
  Setchell, KD; Borriello, SP; Hulme, P; Kirk, DN; Axelson, M (September 1984). “Nonsteroidal estrogens of dietary origin: possible roles in hormone-dependent disease”. The American Journal of Clinical Nutrition. 40 (3): 569–78. doi:10.1093/ajcn/40.3.569. PMID 6383008. S2CID 4467689.
• 9
  Marrian, GF; Haslewood, GA (1932). “Equol, a new inactive phenol isolated from the ketohydroxyoestrin fraction of mares’ urine”. The Biochemical Journal. 26 (4): 1227–32. doi:10.1042/bj0261227. PMC 1261026. PMID 16744928.
• 10
  Atkinson, C; Frankenfeld, CL; Lampe, JW (March 2005). “Gut bacterial metabolism of the soy isoflavone daidzein: exploring the relevance to human health”. Experimental Biology and Medicine. 230 (3): 155–70. doi:10.1177/153537020523000302. PMID 15734719. S2CID 14112442.
• 11
  Wang XL, Hur HG, Lee JH, Kim KT, Kim SI (January 2005). “Enantioselective synthesis of S-equol from dihydrodaidzein by a newly isolated anaerobic human intestinal bacterium”. Appl. Environ. Microbiol. 71 (1): 214–9. Bibcode:2005ApEnM..71..214W. doi:10.1128/AEM.71.1.214-219.2005. PMC 544246. PMID 15640190.
• 12
  Mueller SO, Simon S, Chae K, Metzler M, Korach KS (April 2004). “Phytoestrogens and their human metabolites show distinct agonistic and antagonistic properties on estrogen receptor {α} (ER{α}) and ERβ in human cells”. Toxicol. Sci. 80 (1): 14–25. doi:10.1093/toxsci/kfh147. PMID 15084758.
• 13
  Muthyala, Rajeev S; Ju, Young H; Sheng, Shubin; Williams, Lee D; Doerge, Daniel R; Katzenellenbogen, Benita S; Helferich, William G; Katzenellenbogen, John A (2004). “Equol, a natural estrogenic metabolite from soy isoflavones”. Bioorganic & Medicinal Chemistry. 12 (6): 1559–1567. doi:10.1016/j.bmc.2003.11.035. ISSN 0968-0896. PMID 15018930.
• 14
  Setchell, KD; Clerici, C; Lephart, ED; Cole, SJ; Heenan, C; Castellani, D; Wolfe, BE; Nechemias-Zimmer, L; Brown, NM; Lund, TD; Handa, RJ; Heubi, JE (May 2005). “S-equol, a potent ligand for estrogen receptor beta, is the exclusive enantiomeric form of the soy isoflavone metabolite produced by human intestinal bacterial flora”. The American Journal of Clinical Nutrition. 81 (5): 1072–9. doi:10.1093/ajcn/81.5.1072. PMID 15883431.
• 15
  Prossnitz, Eric R.; Barton, Matthias (2014). “Estrogen biology: New insights into GPER function and clinical opportunities”. Molecular and Cellular Endocrinology. 389 (1–2): 71–83. doi:10.1016/j.mce.2014.02.002. ISSN 0303-7207. PMC 4040308. PMID 24530924.
• 16
  Setchell, KD; Zhao, X; Jha, P; Heubi, JE; Brown, NM (Oct 2009). “The pharmacokinetic behavior of the soy isoflavone metabolite S-(-)equol and its diastereoisomer R-(+)equol in healthy adults determined by using stable-isotope-labeled tracers”. The American Journal of Clinical Nutrition. 90 (4): 1029–37. doi:10.3945/ajcn.2009.27981. PMC 2744624. PMID 19710188.
• 17
  Setchell, KD; Zhao, X; Shoaf, SE; Ragland, K (Nov 2009). “The pharmacokinetics of S-(-)equol administered as SE5-OH tablets to healthy postmenopausal women”. The Journal of Nutrition. 139 (11): 2037–43. doi:10.3945/jn.109.110874. PMID 19776178.
• 18
  Setchell, KD; Clerici, C (Jul 2010). “Equol: pharmacokinetics and biological actions”. The Journal of Nutrition. 140 (7): 1363S–8S. doi:10.3945/jn.109.119784. PMC 2884334. PMID 20519411.
• 19
  Setchell, KD; Borriello, SP; Hulme, P; Kirk, DN; Axelson, M (September 1984). “Nonsteroidal estrogens of dietary origin: possible roles in hormone-dependent disease”. The American Journal of Clinical Nutrition. 40 (3): 569–78. doi:10.1093/ajcn/40.3.569. PMID 6383008. S2CID 4467689.
• 20
  Setchell, KD; Clerici, C (July 2010). “Equol: history, chemistry, and formation”. The Journal of Nutrition. 140 (7): 1355S–62S. doi:10.3945/jn.109.119776. PMC 2884333. PMID 20519412.
• 21
  Setchell, KD; Clerici, C (July 2010). “Equol: history, chemistry, and formation”. The Journal of Nutrition. 140 (7): 1355S–62S. doi:10.3945/jn.109.119776. PMC 2884333. PMID 20519412.
• 22
  Setchell, KD; Clerici, C (July 2010). “Equol: history, chemistry, and formation”. The Journal of Nutrition. 140 (7): 1355S–62S. doi:10.3945/jn.109.119776. PMC 2884333. PMID 20519412.
• 23
  Setchell, KD; Cole, SJ (August 2006). “Method of defining equol-producer status and its frequency among vegetarians”. The Journal of Nutrition. 136 (8): 2188–93. doi:10.1093/jn/136.8.2188. PMID 16857839.
• 24
  Rowland, IR; Wiseman, H; Sanders, TA; Adlercreutz, H; Bowey, EA (2000). “Interindividual variation in metabolism of soy isoflavones and lignans: influence of habitual diet on equol production by the gut microflora”. Nutrition and Cancer. 36 (1): 27–32. doi:10.1207/S15327914NC3601_5. PMID 10798213. S2CID 10603402.
• 25
  Watanabe, S; Yamaguchi, M; Sobue, T; Takahashi, T; Miura, T; Arai, Y; Mazur, W; Wähälä, K; Adlercreutz, H (October 1998). “Pharmacokinetics of soybean isoflavones in plasma, urine and feces of men after ingestion of 60 g baked soybean powder (kinako)”. The Journal of Nutrition. 128 (10): 1710–5. doi:10.1093/jn/128.10.1710. PMID 9772140.
• 26
  Arai, Y; Uehara, M; Sato, Y; Kimira, M; Eboshida, A; Adlercreutz, H; Watanabe, S (March 2000). “Comparison of isoflavones among dietary intake, plasma concentration and urinary excretion for accurate estimation of phytoestrogen intake”. Journal of Epidemiology. 10 (2): 127–35. doi:10.2188/jea.10.127. PMID 10778038.
• 27
  Akaza, H; Miyanaga, N; Takashima, N; Naito, S; Hirao, Y; Tsukamoto, T; Fujioka, T; Mori, M; Kim, WJ; Song, JM; Pantuck, AJ (February 2004). “Comparisons of percent equol producers between prostate cancer patients and controls: case-controlled studies of isoflavones in Japanese, Korean and American residents”. Japanese Journal of Clinical Oncology. 34 (2): 86–9. doi:10.1093/jjco/hyh015. PMID 15067102. 
• 28
  Song, KB; Atkinson, C; Frankenfeld, CL; Jokela, T; Wähälä, K; Thomas, WK; Lampe, JW (May 2006). “Prevalence of daidzein-metabolizing phenotypes differs between Caucasian and Korean American women and girls”. The Journal of Nutrition. 136 (5): 1347–51. doi:10.1093/jn/136.5.1347. PMID 16614428.
• 29
  Patisaul, HB; Jefferson, W (October 2010). “The pros and cons of phytoestrogens”. Front Neuroendocrinol. 31 (4): 400–419. doi:10.1016/j.yfrne.2010.03.003. PMC 3074428. PMID 20347861.
• 30
  Atkinson, C; Frankenfeld, CL; Lampe, JW (March 2005). “Gut bacterial metabolism of the soy isoflavone daidzein: exploring the relevance to human health”. Experimental Biology and Medicine. 230 (3): 155–70. doi:10.1177/153537020523000302. PMID 15734719. S2CID 14112442.
• 31
  Atkinson, C; Frankenfeld, CL; Lampe, JW (March 2005). “Gut bacterial metabolism of the soy isoflavone daidzein: exploring the relevance to human health”. Experimental Biology and Medicine. 230 (3): 155–70. doi:10.1177/153537020523000302. PMID 15734719. S2CID 14112442.
• 32
  Setchell, KD; Cole, SJ (August 2006). “Method of defining equol-producer status and its frequency among vegetarians”. The Journal of Nutrition. 136 (8): 2188–93. doi:10.1093/jn/136.8.2188. PMID 16857839.
• 33
  Setchell KD, Clerici C, Lephart ED, Cole SJ, Heenan C, Castellani D, Wolfe BE, Nechemias-Zimmer L, Brown NM, Lund TD, Handa RJ, Heubi JE (2005). “S-equol, a potent ligand for estrogen receptor beta, is the exclusive enantiomeric form of the soy isoflavone metabolite produced by human intestinal bacterial flora”. Am. J. Clin. Nutr. 81 (5): 1072–9. doi:10.1093/ajcn/81.5.1072. PMID 15883431.
• 34
  Setchell, K. D.; Clerici, C. (2010). “Equol: History, Chemistry, and Formation”. The Journal of Nutrition. 140 (7): 1355S–1362S. doi:10.3945/jn.109.119776. PMC 2884333. PMID 20519412.
• 35
  V, Ravishankar Rai; Bai, Jamuna A. (2014-12-17). Beneficial Microbes in Fermented and Functional Foods. CRC Press. ISBN 978-1-4822-0663-0.
• 36
  Reeve V, Widyarini S, Domanski D, Chew K, Barnes K. Protection Against Photoaging in the Hairless Mouse by the Isoflavone Equol. Photochemistry and Photobiology, Volume 81, Issue 6, November 2005, Pages 1548-1553
• 37
  Magnet, U.; Urbanek, C.; Gaisberger, D.; Tomeva, E.; Dum, E.; Pointner, A.; Haslberger, A.G. (October 2017). “Topical equol preparation improves structural and molecular skin parameters”. International Journal of Cosmetic Science. 39 (5): 535–542. doi:10.1111/ics.12408. PMID 28574180. S2CID 44910993.
• 38
  Lephart ED (November 2016). “Skin aging and oxidative stress: Equol’s anti-aging effects via biochemical and molecular mechanisms”. Ageing Research Reviews. 31: 36–54. doi:10.1016/j.arr.2016.08.001. PMID 27521253. S2CID 205668316.
• 39
  Lephart ED (November 2016). “Skin aging and oxidative stress: Equol’s anti-aging effects via biochemical and molecular mechanisms”. Ageing Research Reviews. 31: 36–54. doi:10.1016/j.arr.2016.08.001. PMID 27521253. S2CID 205668316.
• 40
  Lephart, Edwin (2018-01-29). “Equol’s Anti-Aging Effects Protect against Environmental Assaults by Increasing Skin Antioxidant Defense and ECM Proteins While Decreasing Oxidative Stress and Inflammation”. Cosmetics. 5 (1): 16. doi:10.3390/cosmetics5010016. ISSN 2079-9284.
• 41
  Lephart, Edwin D. (November 2013). “Protective effects of equol and their polyphenolic isomers against dermal aging: Microarray/protein evidence with clinical implications and unique delivery into human skin”. Pharmaceutical Biology. 51 (11): 1393–1400. doi:10.3109/13880209.2013.793720. ISSN 1388-0209. PMID 23862588.
• 42
  Lephart, Edwin D. (November 2013). “Protective effects of equol and their polyphenolic isomers against dermal aging: Microarray/protein evidence with clinical implications and unique delivery into human skin”. Pharmaceutical Biology. 51 (11): 1393–1400. doi:10.3109/13880209.2013.793720. ISSN 1388-0209. PMID 23862588.
• 43
  Effect of natural S-equol on bone metabolism in equol non-producing postmenopausal Japanese women: a pilot randomized placebo-controlled trial. Tomomi Ueno of Saga Nutraceutricals Research Institute, Otsuka Pharmaceutical Co., Ltd., Japan, et.al
• 44
  Mayr, Linda; Georgiev, Dimitar; Toulev, Albena (2019-03-01). “Eine Proof-of-concept-Studie von Isoflavandiol-E55-RS-Vaginalkapseln oder Vaginalgel zur Linderung der menopausalen Vaginalatrophie”. Journal für Gynäkologische Endokrinologie/Österreich (in German). 29 (1): 13–22. doi:10.1007/s41974-019-0085-9. ISSN 1996-1553.
• 45
  “Equol Is a Novel Anti-Androgen that Inhibits Prostate Growth and Hormone Feedback, Biology of Reproduction, Volume 70, Issue 4, 1 April 2004, Pages 1188–1195,”. academic.oup.com. Retrieved 2023-11-17.

Kategorien:

GPER-Agonisten | Isoflavandiole | Phytoöstrogene | Steroid-Sulfotransferase-Inhibitoren | Selektive ERβ-Agonisten

Stand vom Feb 16, 2024 @ 15:28, zu den Wikipedia­artikeln … → WpEn

Quellen und Tiefen

• 1
  The structures of 7,4’-dihydroxy-isoflavan and its precursors is shown in Structural Elucidation of Hydroxylated Metabolites of the Isoflavan Equol by GC/MS and HPLC/MS by Corinna E. Rüfer, Hansruedi Glatt, and Sabine E. Kulling in Drug Metabolism and Disposition (2005, electronic publication).
• 2
  Wang XL, Hur HG, Lee JH, Kim KT, Kim SI (January 2005). “Enantioselective synthesis of S-equol from dihydrodaidzein by a newly isolated anaerobic human intestinal bacterium”. Appl. Environ. Microbiol. 71 (1): 214–9. Bibcode:2005ApEnM..71..214W. doi:10.1128/AEM.71.1.214-219.2005. PMC 544246. PMID 15640190.
• 3
  Muthyala, Rajeev S; Ju, Young H; Sheng, Shubin; Williams, Lee D; Doerge, Daniel R; Katzenellenbogen, Benita S; Helferich, William G; Katzenellenbogen, John A (2004). “Equol, a natural estrogenic metabolite from soy isoflavones”. Bioorganic & Medicinal Chemistry. 12 (6): 1559–1567. doi:10.1016/j.bmc.2003.11.035. ISSN 0968-0896. PMID 15018930.
• 4
  Frankenfeld CL, Atkinson C, Thomas WK, et al. (December 2005). “High concordance of daidzein-metabolizing phenotypes in individuals measured 1 to 3 years apart”. Br. J. Nutr. 94 (6): 873–6. doi:10.1079/bjn20051565. PMID 16351761.
• 5
  Marrian, GF; Haslewood, GA (1932). “Equol, a new inactive phenol isolated from the ketohydroxyoestrin fraction of mares’ urine”. The Biochemical Journal. 26 (4): 1227–32. doi:10.1042/bj0261227. PMC 1261026. PMID 16744928.
• 6
  Axelson, M; Kirk, DN; Farrant, RD; Cooley, G; Lawson, AM; Setchell, KD (1982-02-01). “The identification of the weak oestrogen equol [7-hydroxy-3-(4′-hydroxyphenyl)chroman] in human urine”. The Biochemical Journal. 201 (2): 353–7. doi:10.1042/bj2010353. PMC 1163650. PMID 7082293.
• 7
  Setchell, KD; Clerici, C (July 2010). “Equol: history, chemistry, and formation”. The Journal of Nutrition. 140 (7): 1355S–62S. doi:10.3945/jn.109.119776. PMC 2884333. PMID 20519412.
• 8
  Setchell, KD; Borriello, SP; Hulme, P; Kirk, DN; Axelson, M (September 1984). “Nonsteroidal estrogens of dietary origin: possible roles in hormone-dependent disease”. The American Journal of Clinical Nutrition. 40 (3): 569–78. doi:10.1093/ajcn/40.3.569. PMID 6383008. S2CID 4467689.
• 9
  Marrian, GF; Haslewood, GA (1932). “Equol, a new inactive phenol isolated from the ketohydroxyoestrin fraction of mares’ urine”. The Biochemical Journal. 26 (4): 1227–32. doi:10.1042/bj0261227. PMC 1261026. PMID 16744928.
• 10
  Atkinson, C; Frankenfeld, CL; Lampe, JW (March 2005). “Gut bacterial metabolism of the soy isoflavone daidzein: exploring the relevance to human health”. Experimental Biology and Medicine. 230 (3): 155–70. doi:10.1177/153537020523000302. PMID 15734719. S2CID 14112442.
• 11
  Wang XL, Hur HG, Lee JH, Kim KT, Kim SI (January 2005). “Enantioselective synthesis of S-equol from dihydrodaidzein by a newly isolated anaerobic human intestinal bacterium”. Appl. Environ. Microbiol. 71 (1): 214–9. Bibcode:2005ApEnM..71..214W. doi:10.1128/AEM.71.1.214-219.2005. PMC 544246. PMID 15640190.
• 12
  Mueller SO, Simon S, Chae K, Metzler M, Korach KS (April 2004). “Phytoestrogens and their human metabolites show distinct agonistic and antagonistic properties on estrogen receptor {α} (ER{α}) and ERβ in human cells”. Toxicol. Sci. 80 (1): 14–25. doi:10.1093/toxsci/kfh147. PMID 15084758.
• 13
  Muthyala, Rajeev S; Ju, Young H; Sheng, Shubin; Williams, Lee D; Doerge, Daniel R; Katzenellenbogen, Benita S; Helferich, William G; Katzenellenbogen, John A (2004). “Equol, a natural estrogenic metabolite from soy isoflavones”. Bioorganic & Medicinal Chemistry. 12 (6): 1559–1567. doi:10.1016/j.bmc.2003.11.035. ISSN 0968-0896. PMID 15018930.
• 14
  Setchell, KD; Clerici, C; Lephart, ED; Cole, SJ; Heenan, C; Castellani, D; Wolfe, BE; Nechemias-Zimmer, L; Brown, NM; Lund, TD; Handa, RJ; Heubi, JE (May 2005). “S-equol, a potent ligand for estrogen receptor beta, is the exclusive enantiomeric form of the soy isoflavone metabolite produced by human intestinal bacterial flora”. The American Journal of Clinical Nutrition. 81 (5): 1072–9. doi:10.1093/ajcn/81.5.1072. PMID 15883431.
• 15
  Prossnitz, Eric R.; Barton, Matthias (2014). “Estrogen biology: New insights into GPER function and clinical opportunities”. Molecular and Cellular Endocrinology. 389 (1–2): 71–83. doi:10.1016/j.mce.2014.02.002. ISSN 0303-7207. PMC 4040308. PMID 24530924.
• 16
  Setchell, KD; Zhao, X; Jha, P; Heubi, JE; Brown, NM (Oct 2009). “The pharmacokinetic behavior of the soy isoflavone metabolite S-(-)equol and its diastereoisomer R-(+)equol in healthy adults determined by using stable-isotope-labeled tracers”. The American Journal of Clinical Nutrition. 90 (4): 1029–37. doi:10.3945/ajcn.2009.27981. PMC 2744624. PMID 19710188.
• 17
  Setchell, KD; Zhao, X; Shoaf, SE; Ragland, K (Nov 2009). “The pharmacokinetics of S-(-)equol administered as SE5-OH tablets to healthy postmenopausal women”. The Journal of Nutrition. 139 (11): 2037–43. doi:10.3945/jn.109.110874. PMID 19776178.
• 18
  Setchell, KD; Clerici, C (Jul 2010). “Equol: pharmacokinetics and biological actions”. The Journal of Nutrition. 140 (7): 1363S–8S. doi:10.3945/jn.109.119784. PMC 2884334. PMID 20519411.
• 19
  Setchell, KD; Borriello, SP; Hulme, P; Kirk, DN; Axelson, M (September 1984). “Nonsteroidal estrogens of dietary origin: possible roles in hormone-dependent disease”. The American Journal of Clinical Nutrition. 40 (3): 569–78. doi:10.1093/ajcn/40.3.569. PMID 6383008. S2CID 4467689.
• 20
  Setchell, KD; Clerici, C (July 2010). “Equol: history, chemistry, and formation”. The Journal of Nutrition. 140 (7): 1355S–62S. doi:10.3945/jn.109.119776. PMC 2884333. PMID 20519412.
• 21
  Setchell, KD; Clerici, C (July 2010). “Equol: history, chemistry, and formation”. The Journal of Nutrition. 140 (7): 1355S–62S. doi:10.3945/jn.109.119776. PMC 2884333. PMID 20519412.
• 22
  Setchell, KD; Clerici, C (July 2010). “Equol: history, chemistry, and formation”. The Journal of Nutrition. 140 (7): 1355S–62S. doi:10.3945/jn.109.119776. PMC 2884333. PMID 20519412.
• 23
  Setchell, KD; Cole, SJ (August 2006). “Method of defining equol-producer status and its frequency among vegetarians”. The Journal of Nutrition. 136 (8): 2188–93. doi:10.1093/jn/136.8.2188. PMID 16857839.
• 24
  Rowland, IR; Wiseman, H; Sanders, TA; Adlercreutz, H; Bowey, EA (2000). “Interindividual variation in metabolism of soy isoflavones and lignans: influence of habitual diet on equol production by the gut microflora”. Nutrition and Cancer. 36 (1): 27–32. doi:10.1207/S15327914NC3601_5. PMID 10798213. S2CID 10603402.
• 25
  Watanabe, S; Yamaguchi, M; Sobue, T; Takahashi, T; Miura, T; Arai, Y; Mazur, W; Wähälä, K; Adlercreutz, H (October 1998). “Pharmacokinetics of soybean isoflavones in plasma, urine and feces of men after ingestion of 60 g baked soybean powder (kinako)”. The Journal of Nutrition. 128 (10): 1710–5. doi:10.1093/jn/128.10.1710. PMID 9772140.
• 26
  Arai, Y; Uehara, M; Sato, Y; Kimira, M; Eboshida, A; Adlercreutz, H; Watanabe, S (March 2000). “Comparison of isoflavones among dietary intake, plasma concentration and urinary excretion for accurate estimation of phytoestrogen intake”. Journal of Epidemiology. 10 (2): 127–35. doi:10.2188/jea.10.127. PMID 10778038.
• 27
  Akaza, H; Miyanaga, N; Takashima, N; Naito, S; Hirao, Y; Tsukamoto, T; Fujioka, T; Mori, M; Kim, WJ; Song, JM; Pantuck, AJ (February 2004). “Comparisons of percent equol producers between prostate cancer patients and controls: case-controlled studies of isoflavones in Japanese, Korean and American residents”. Japanese Journal of Clinical Oncology. 34 (2): 86–9. doi:10.1093/jjco/hyh015. PMID 15067102. 
• 28
  Song, KB; Atkinson, C; Frankenfeld, CL; Jokela, T; Wähälä, K; Thomas, WK; Lampe, JW (May 2006). “Prevalence of daidzein-metabolizing phenotypes differs between Caucasian and Korean American women and girls”. The Journal of Nutrition. 136 (5): 1347–51. doi:10.1093/jn/136.5.1347. PMID 16614428.
• 29
  Patisaul, HB; Jefferson, W (October 2010). “The pros and cons of phytoestrogens”. Front Neuroendocrinol. 31 (4): 400–419. doi:10.1016/j.yfrne.2010.03.003. PMC 3074428. PMID 20347861.
• 30
  Atkinson, C; Frankenfeld, CL; Lampe, JW (March 2005). “Gut bacterial metabolism of the soy isoflavone daidzein: exploring the relevance to human health”. Experimental Biology and Medicine. 230 (3): 155–70. doi:10.1177/153537020523000302. PMID 15734719. S2CID 14112442.
• 31
  Atkinson, C; Frankenfeld, CL; Lampe, JW (March 2005). “Gut bacterial metabolism of the soy isoflavone daidzein: exploring the relevance to human health”. Experimental Biology and Medicine. 230 (3): 155–70. doi:10.1177/153537020523000302. PMID 15734719. S2CID 14112442.
• 32
  Setchell, KD; Cole, SJ (August 2006). “Method of defining equol-producer status and its frequency among vegetarians”. The Journal of Nutrition. 136 (8): 2188–93. doi:10.1093/jn/136.8.2188. PMID 16857839.
• 33
  Setchell KD, Clerici C, Lephart ED, Cole SJ, Heenan C, Castellani D, Wolfe BE, Nechemias-Zimmer L, Brown NM, Lund TD, Handa RJ, Heubi JE (2005). “S-equol, a potent ligand for estrogen receptor beta, is the exclusive enantiomeric form of the soy isoflavone metabolite produced by human intestinal bacterial flora”. Am. J. Clin. Nutr. 81 (5): 1072–9. doi:10.1093/ajcn/81.5.1072. PMID 15883431.
• 34
  Setchell, K. D.; Clerici, C. (2010). “Equol: History, Chemistry, and Formation”. The Journal of Nutrition. 140 (7): 1355S–1362S. doi:10.3945/jn.109.119776. PMC 2884333. PMID 20519412.
• 35
  V, Ravishankar Rai; Bai, Jamuna A. (2014-12-17). Beneficial Microbes in Fermented and Functional Foods. CRC Press. ISBN 978-1-4822-0663-0.
• 36
  Reeve V, Widyarini S, Domanski D, Chew K, Barnes K. Protection Against Photoaging in the Hairless Mouse by the Isoflavone Equol. Photochemistry and Photobiology, Volume 81, Issue 6, November 2005, Pages 1548-1553
• 37
  Magnet, U.; Urbanek, C.; Gaisberger, D.; Tomeva, E.; Dum, E.; Pointner, A.; Haslberger, A.G. (October 2017). “Topical equol preparation improves structural and molecular skin parameters”. International Journal of Cosmetic Science. 39 (5): 535–542. doi:10.1111/ics.12408. PMID 28574180. S2CID 44910993.
• 38
  Lephart ED (November 2016). “Skin aging and oxidative stress: Equol’s anti-aging effects via biochemical and molecular mechanisms”. Ageing Research Reviews. 31: 36–54. doi:10.1016/j.arr.2016.08.001. PMID 27521253. S2CID 205668316.
• 39
  Lephart ED (November 2016). “Skin aging and oxidative stress: Equol’s anti-aging effects via biochemical and molecular mechanisms”. Ageing Research Reviews. 31: 36–54. doi:10.1016/j.arr.2016.08.001. PMID 27521253. S2CID 205668316.
• 40
  Lephart, Edwin (2018-01-29). “Equol’s Anti-Aging Effects Protect against Environmental Assaults by Increasing Skin Antioxidant Defense and ECM Proteins While Decreasing Oxidative Stress and Inflammation”. Cosmetics. 5 (1): 16. doi:10.3390/cosmetics5010016. ISSN 2079-9284.
• 41
  Lephart, Edwin D. (November 2013). “Protective effects of equol and their polyphenolic isomers against dermal aging: Microarray/protein evidence with clinical implications and unique delivery into human skin”. Pharmaceutical Biology. 51 (11): 1393–1400. doi:10.3109/13880209.2013.793720. ISSN 1388-0209. PMID 23862588.
• 42
  Lephart, Edwin D. (November 2013). “Protective effects of equol and their polyphenolic isomers against dermal aging: Microarray/protein evidence with clinical implications and unique delivery into human skin”. Pharmaceutical Biology. 51 (11): 1393–1400. doi:10.3109/13880209.2013.793720. ISSN 1388-0209. PMID 23862588.
• 43
  Effect of natural S-equol on bone metabolism in equol non-producing postmenopausal Japanese women: a pilot randomized placebo-controlled trial. Tomomi Ueno of Saga Nutraceutricals Research Institute, Otsuka Pharmaceutical Co., Ltd., Japan, et.al
• 44
  Mayr, Linda; Georgiev, Dimitar; Toulev, Albena (2019-03-01). “Eine Proof-of-concept-Studie von Isoflavandiol-E55-RS-Vaginalkapseln oder Vaginalgel zur Linderung der menopausalen Vaginalatrophie”. Journal für Gynäkologische Endokrinologie/Österreich (in German). 29 (1): 13–22. doi:10.1007/s41974-019-0085-9. ISSN 1996-1553.
• 45
  “Equol Is a Novel Anti-Androgen that Inhibits Prostate Growth and Hormone Feedback, Biology of Reproduction, Volume 70, Issue 4, 1 April 2004, Pages 1188–1195,”. academic.oup.com. Retrieved 2023-11-17.

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