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Equol
Biological functions of estrone
1. Hormonal like effects
As a metabolic product of soy isoflavones, estrogenic effects of estradiol were the first to receive attention. When there is a deficiency of estrogen in the body, it can become an estrogen agonist; When there is an excessive amount of estrogen in the body, it competes with ER for binding, reducing the opportunity for estrogen to bind with ER, thereby reducing the promoting effect of estrogen on cell proliferation and lowering the risk of estrogen related diseases.
Female estrogen imbalance can lead to many diseases, such as breast cancer, atherosclerosis, osteoporosis, and estrol can combine with ER receptor to play the role of estrogen, thus inhibiting the related diseases caused by estrogen imbalance.
Estrogen exhibits anti androgenic effects in male animals. Estrogen has a high affinity for 5 α - dihydrotestosterone (5 α - DHT) and can bind to it to isolate it, but cannot bind to 5 α - DHT receptors. Androgens can promote the growth of prostate cancer cells.
2. Antioxidant
Estrogen belongs to polyphenolic substances and can act as a hydrogen/electron acceptor to scavenge free radicals.
3. Immune regulation
The immunoprotective effect of estradiol may be mediated by its antioxidant activity. Applying estradiol has an immunoprotective effect on the skin, not only by activating the estrogen receptor signaling pathway in the skin, but also by inducing the endogenous skin antioxidant enzyme heme oxygenase (HO) to provide protection.
4. Health function
A large number of medical studies have shown that estrone has a certain effect on the prevention and treatment of tumors and cardiovascular diseases. R-Eq and S-Eq can inhibit the proliferation of human breast cancer MDA-MB-231 cells by down regulating the expression of matrix metalloproteinase-2 (MMP-2). Estrogen has an inhibitory effect on skin cancer induced by ultraviolet radiation or 7,12-dimethylanthracene (2).
| Concentration / Solvent Volume / Mass | 1 mg | 5 mg | 10 mg |
|---|---|---|---|
| 1 mM | 4.1276 mL | 20.6381 mL | 41.2763 mL |
| 5 mM | 0.8255 mL | 4.1276 mL | 8.2553 mL |
| 10 mM | 0.4128 mL | 2.0638 mL | 4.1276 mL |
Equol (4',7-isoflavandiol) is an isoflavandiol[1] estrogen metabolized from daidzein, a type of isoflavone found in soybeans and other plant sources, by bacterial flora in the intestines.[2][3] While endogenous estrogenic hormones such as estradiol are steroids, equol is a nonsteroidal estrogen. Only about 30–50% of people have intestinal bacteria that make equol.
| (+/-)-EQUOL Basic information |
| Product Name: | (+/-)-EQUOL |
| Synonyms: | 7,4'-HoMoisoflavane;NV 07α;3-(4-Hydroxyphenyl)-3,4-dihydro-2H-1-benzopyran-7-ol 7-Hydroxy-3-(4-hydroxyphenyl)chroman 4',7-Isoflavandiol;3,4-Dihydro-3-(4-hydroxyphenyl)-2H-chromen-7-ol, (+/-)-Equol, 4',7-Isoflavandiol, 7-Hydroxy-3-(4-hydroxyphenyl)chroman;4',7-Isoflavandiol, (+/-)-Equol;4′,7-Dihydroxyisoflavane;(+/-)-Equol (GMP);(±)-EQUOL >= 99.0% (TLC) |
| CAS: | 94105-90-5 |
| MF: | C15H14O3 |
| MW: | 242.27 |
| EINECS: | 618-999-2 |
| Product Categories: | Metabolites;metabolite;Aromatics;Heterocycles;Intermediates & Fine Chemicals;Metabolites & Impurities;Pharmaceuticals |
| Mol File: | 94105-90-5.mol |
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| (+/-)-EQUOL Chemical Properties |
| Melting point | 158-160?C |
| Boiling point | 441.7±45.0 °C(Predicted) |
| density | 1.286±0.06 g/cm3(Predicted) |
| storage temp. | Inert atmosphere,Store in freezer, under -20°C |
| solubility | soluble in Ethanol |
| form | Crystalline powder |
| pka | 9.94±0.40(Predicted) |
| color | White to Light yellow to Light red |
| Water Solubility | Soluble in DMSO and methanol or 100% ethanol. Insoluble in water. |
| Sensitive | Hygroscopic |
| BRN | 87752 |
| InChI | InChI=1S/C15H14O3/c16-13-4-1-10(2-5-13)12-7-11-3-6-14(17)8-15(11)18-9-12/h1-6,8,12,16-17H,7,9H2 |
| InChIKey | ADFCQWZHKCXPAJ-UHFFFAOYSA-N |
| SMILES | C1OC2=CC(O)=CC=C2CC1C1=CC=C(O)C=C1 |
| Safety Information |
| WGK Germany | 3 |
| HS Code | 2932990090 |
| MSDS Information |
| (+/-)-EQUOL Usage And Synthesis |
| Description | Equol is a nonsteroidal estrogen produced from the metabolism of the isoflavonoid phytoestrogen daidzein by human intestinal microflora. The estrogen receptor (ER) binding activity of the naturally occurring (S)-enantiomer demonstrates greater affinity toward ERβ while the (R)-enantiomer demonstrates greater affinity towards ERα. Synthesized as a racemic mixture, (±)-equol exhibits EC50 values of 200 and 74 nM for human ERα and ERβ, respectively and induces breast cancer cell proliferation in vitro at concentrations as low as 100 nM. |
| Chemical Properties | White to Off-White Solid |
| Uses | (R,S)-Equol is a human urinary metabolite of the soy isoflavones Daidzein (D103500). |
| Uses | (+/-)-Equol exhibits EC50 values of 200 and 74 nM for human ERα and ERβ, respectively and induces breast cancer cell proliferation in vitro at concentrations as low as 100 nM. It is a weak estrogenic agonist, and competitive inhibitor of 17β-estradiol at the estradiol receptor. It inhibits 12-O-tetradecanoylphorbol 13-acetate (TPA)-induced neoplastic cell transformation by targeting the MEK/ERK/p90RSK/activator protein-1 signalling pathway. It functions as a DHT blocker. |
| Uses | A human urinary metabolite of Daidzein. It is also a natural estrogenic metabolite from soy isoflavones. |
| Definition | ChEBI: 3-(4-Hydroxyphenyl)chroman-7-ol is a member of hydroxyisoflavans. |
| Application | (±)-Equol is a metabolite produced in vivo from the soy phytoestrogen daidzein by the action of certain gut microflora, and is a nonsteroidal estrogen of the isoflavonoid class. (±)-Equo has been reported to have estrogenic activity and affinity for estrogen receptors. (±)-Equo can exist in two enantiomeric forms, (S)-equol and (R)-equol. In binding assays, (S)-equol has a higher binding affinity for estrogen β receptors. |
| Biological Activity | Metabolite of daidzein. Weak estrogenic agonist, and competitive inhibitor of 17β-estradiol at the estradiol receptor. (R,S)-Equol is a flavonoid. Racemic mixture. This is a metabolite that is produced in vivo from soy phytoestrogen daidzein from gut microflora. (R,S)-Equol inhibits 12-O-tetradecanoylphorbol 13-acetate (TPA)-induced neoplastic cell transformation by targeting the MEK/ERK/p90RSK/activator protein-1 signalling pathway. (R,S)-Equol shows positive effects on the incidence of prostate cancer. Functions as a DHT blocker. Preferentially activates estrogen receptor β (ERβ). |
| Biochem/physiol Actions | Metabolite of daidzein. Weak estrogenic agonist, and competitive inhibitor of 17β-estradiol at the estradiol receptor. |
| References | Equol, a natural estrogenic metabolite from soy isoflavones convenient preparation and resolution of R- and S-equols and their differing binding and biological activity through estrogen receptors alpha and beta R. S. Muthyala, Y. H. Ju, S. Sheng, L. D. Williams, D. R. Doerge, B. S. Katzenellenbogen, W. G. Helferich, J. A. Katzenellenbogen, Bioorg. Med. Chem. 2004, 12, 1559. Isolation and identification of new bacterial stains producing equol from Pueraria lobate extract fermentation J. E. Kwon, J. Lim, I. Kim, D. Kim, S. C. Kang, PLoS ONE 2018, 13, e0192490. Setchell, K.D.R., Clerici, C., Lephart, E.D., et al. S-equol, a potent ligand for estrogen receptor β, is the exclusive enantiomeric form of the soy isoflavone metabolite produced by human intestinal bacterial flora. Am. J. Clin. Nutr. 81(5), 1072-1079 (2005). Liu, H., Du, J., Hu, C., et al. Delayed activation of extracellular-signal-regulated kinase ? is involved in genistein- and equol-induced cell proliferation and estrogen-receptor-α-mediated transcription in MCF-7 breast cancer cells. Journal of Nutritional Biochemistry (2009). |
See also
[edit]
Daidzein
Estrogen receptor
Genistein
Liquiritigenin
Menerba
Prinaberel
WAY-200070
Diarylpropionitrile
References
[edit]
^ 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).
^ Jump up to:a b 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.
^ Jump up to:a b c 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.
^ 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.
^ 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.
^ Jump up to:a b c 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.
^ 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.
^ Jump up to:a b 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.
^ Setchell, KD; Brown, NM; Lydeking-Olsen, E (December 2002). "The clinical importance of the metabolite equol-a clue to the effectiveness of soy and its isoflavones". The Journal of Nutrition. 132 (12): 3577–84. doi:10.1093/jn/132.12.3577. PMID 12468591.
^ Jump up to:a b c 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.
^ 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.
^ 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.
^ 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.
^ 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.
^ 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.
^ 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.
^ Lampe, JW; Karr, SC; Hutchins, AM; Slavin, JL (March 1998). "Urinary equol excretion with a soy challenge: influence of habitual diet". Proceedings of the Society for Experimental Biology and Medicine. 217 (3): 335–9. doi:10.3181/00379727-217-44241. PMID 9492344. S2CID 23496918.
^ 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.
^ 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.
^ 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.
^ 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.
^ 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.
^ 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.
^ 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.
^ Teas, J.; Hurley, TG (August 2009). "Dietary seaweed modifies estrogen and phytoestrogen metabolism in healthy postmenopausal women". The Journal of Nutrition. 139 (9): 939–44. doi:10.3945/jn.108.100834. PMID 19321575.
^ 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.
^ 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.
^ 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.
^ V, Ravishankar Rai; Bai, Jamuna A. (2014-12-17). Beneficial Microbes in Fermented and Functional Foods. CRC Press. ISBN 978-1-4822-0663-0.
^ 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
^ 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.
^ 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.
^ Urbanek C, Haslberger A, Hippe B, Gessner D, Fiala H, Equol – a Topically Applied Phyto-Oestrogen Improves Skin Characteristics. Global ingredients and Formulations Guide 2016
^ 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.
^ Jump up to:a b 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.
^ Efficacy and safety of natural S-equol supplement in US postmenopausal women. Belinda H. Jenks of Scientific Affairs, Pharmavite LLC, Northridge, CA, et.al.
^ 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
^ 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.
^ "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". Retrieved 2023-11-17.
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