Jump to content

Daidzein

From Wikipedia, the free encyclopedia

This is an old revision of this page, as edited by 70.137.131.199 (talk) at 10:21, 7 August 2012 (minor ed ref). The present address (URL) is a permanent link to this revision, which may differ significantly from the current revision.

Not to be confused with Daidzin.
Daidzein
Names
IUPAC name
7-Hydroxy-3-(4-hydroxyphenyl) chromen-4-one
Other names
4',7-Dihydroxyisoflavone
Daidzeol
Isoaurostatin
Identifiers
3D model (JSmol)
ChEBI
ChEMBL
ChemSpider
ECHA InfoCard 100.006.942 Edit this at Wikidata
KEGG
UNII
  • InChI=1S/C15H10O4/c16-10-3-1-9(2-4-10)13-8-19-14-7-11(17)5-6-12(14)15(13)18/h1-8,16-17H checkY
    Key: ZQSIJRDFPHDXIC-UHFFFAOYSA-N checkY
  • InChI=1/C15H10O4/c16-10-3-1-9(2-4-10)13-8-19-14-7-11(17)5-6-12(14)15(13)18/h1-8,16-17H
    Key: ZQSIJRDFPHDXIC-UHFFFAOYAG
  • O=C\1c3c(O/C=C/1c2ccc(O)cc2)cc(O)cc3
Properties
C15H10O4
Molar mass 254.23 g/mol
Appearance Pale yellow prisms
Melting point 315–323 °C
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
checkY verify (what is checkY☒N ?)

Daidzein structurally belongs to the group of isoflavones. Daidzein and other isoflavone compounds, such as genistein, are present in a number of plants and herbs like the Thai Kwao Krua or Pueraria mirifica, Kudzu or Pueraria lobata, and in food sources such as soybeans and soy products like tofu and textured vegetable protein. Soy isoflavones are a group of compounds found in and isolated from the soybean. Of note, total isoflavones in soy beans are—in general—37 percent daidzein, 57 percent genistein and 6 percent glycitein, according to USDA data.[2] Soy germ contains 41.7 percent daidzein.[3] Besides functioning as antioxidants, isoflavones have been shown to interact with animal and human estrogen receptors, and are therefore referred to as phytoestrogens. Soy isoflavones also produce non-hormonal effects.

Daidzein can be converted to its end metabolite S-equol in some humans based on the presence of certain intestinal bacteria. Based on several decades of research, S-equol has potential for significant health benefits.

Daidzein is not legally classified as a drug in the United States. It has not been tested in clinical trials to make sure that it is both safe and effective for treating any disease, although studies of soy or soy isoflavones have found evidence of some health benefits and minimal adverse effects. Daidzein is legally classified as a dietary supplement in the United States, typically available in soy germ or soy extract. Dietary supplements are not regulated as drugs in the U.S., and the labeling of dietary supplements in the U.S. may not describe the supplement as having any drug activity or effectiveness.

Biological activities

Scientists have studied some of the activities of daidzein in their laboratories, working with cells or with animals such as mice. Studies in cells and in animals sometimes give hints as to what a chemical might do when given to humans, but no one can know what a chemical does in humans until the chemical is tested in a clinical trial.

Activation of PPARs

Isoflavone daidzein transactivates all three PPAR[clarification needed] isoforms, α, δ, and γ and influences target cells.[4] Similar to another isoflavone genistein,[5] daidzein at concentrations between 1 and 100 uM activates PPARs in a dose dependent way in KS483 mesenchymal progenitor cells, breast cancer MCF-7 cells, T47D cells and MDA-MD-231 cells. Studies have shown that both ERs and PPARs influence each other and therefore induce differential effects in a dose-dependent way. The final biological effects of daidzein are determined by the balance among these pleiotrophic actions.[4][6]

Cell proliferation studies

Daidzein, like other isoflavones, has both estrogenic and anti-estrogenic effects. Soy supplements are often consumed by women for alleviating menopausal symptoms or for the perceived protective effects against breast cancer, particularly after a well documented low incidence rates of breast cancer and high soy food intake among Asian women.[7] But taking soy supplements carries serious risks of harm, especially in people who already have cancer and are taking drugs to treat the cancer. Experimental evidence in cells and in animals show that even low concentration stimulates breast tumor growth in in vitro and in vivo, and interfere with the antitumor effect of the cancer drug, tamoxifen.[8] T47D:A18/PKC alpha tumor growth was demonstrated to be stimulated by genistein, but partially inhibited by daidzein; however, coadministration of TAM with either daidzein or genistein produced tumors of greater size.[9] On the other hand an epidemiological study suggests a hypothesis that soy isoflavones consumed at levels comparable to those in Asian populations may reduce the risk of cancer recurrence in women receiving TAM therapy and moreover, appears not to interfere with the drug efficacy.[10] Supportingly daidzein was demonstrated to induce human MCF-7 breast cancer cell line apoptosis through the mitochondrial caspase-dependent cell death pathway.[11] However, epidemiological studies suggest that consuming soy isoflavones reduces the risks of certain types of cancer including breast and endometrial.[12][13] Additionally, clinical studies, in which 44 to 103 milligrams of daidzein were consumed daily for two years, showed minimal risks in menopausal women.[14][15][16]

Antioxidant

Phytoestrogens are often strong antioxidant compounds. Antioxidants are important in maintaining normal physiology. Some people think that antioxidants might prevent aging by eliminating harmful free radicals but there is no evidence that this is true in humans. Scientific studies of daidzein's antioxidant abilities have given contradictory results: some studies have shown antioxidant properties in laboratory experiments on cells, but in other experiments daidzein has caused oxidative stress on cells.[17]

Daidzein metabolite S-equol activities

Daidzein, when consumed from soy, is transformed in some, but not all, humans to produce S-Equol [7-hydroxy-3-(49-hydroxyphenyl)-chroman],[18] which may have some health benefits, particularly the reduction of some menopausal symptoms. Because it is a metabolite of daidzein, S-equol is not of plant origin. The molecular and physical structure of S-equol is similar to that of estradiol,[19] the main sex hormone found in women.

The ability to transform daidzein into S-equol is based on the presence of certain intestinal bacteria. In fact, several studies indicate that only 25 to 30 percent of the adult population of Western countries produces S-equol after eating soy foods containing isoflavones,[19][20][21][22] significantly lower than the reported 50 to 60 percent frequency of equol-producers in adults from Japan, Korea, or China.[23][24][25][26]

Although still under investigation, the ability to produce S-equol may be associated with other health benefits, according to data from epidemiological and intervention studies. Studies in both animal models and humans have yielded data about the potential of S-equol use in menopause,[27][28][29][30] breast,[19] bone[31][32] and prostate health.[19]

Based on several decades of research, Kenneth D. R. Setchell, PhD., et al., proposed in 2002 that S-equol had potential for disease prevention and treatment. The scientists described that “There is good rationale for expecting greater efficacy in equol-producers because equol binds with greater affinity to estrogen receptor than daidzein.”[33]

Supplements containing S-equol are under development, and testing in humans is ongoing for the management of menopausal symptoms, including the reduction in the frequency and severity of hot flashes as well as neck and shoulder stiffness.[27][34][35]

Glycosides

List of plants that contain the chemical

Notes and references

  1. ^ Merck Index, 11th Edition, 2805.
  2. ^ "Isoflavones contents of food". Top Cultures. Retrieved 15 May 2012.
  3. ^ Zhang, Y. (1999). "Urinary disposition of the soybean isoflavones daidzein, genistein and glycitein differs among humans with moderate fecal isoflavone degradation activity". The Journal of Nutrition. 129 (5): 957–962. PMID 10222386. {{cite journal}}: Unknown parameter |coauthors= ignored (|author= suggested) (help)
  4. ^ a b Dang Z. C.; Löwik, C. (2004). "The Balance between Concurrent Activation of ERs and PPARs Determines Daidzein-Induced Osteogenesis and Adipogenesis". Journal of Bone and Mineral Research. 19 (5): 853–861. doi:10.1359/jbmr.040120. PMID 15068509.{{cite journal}}: CS1 maint: multiple names: authors list (link)
  5. ^ Dang Z. C. (2009). "Dose-dependent effects of soy phyto-oestrogen genistein on adipocytes: mechanisms of action". Obesity Reviews. 10 (3): 342–349. doi:10.1111/j.1467-789X.2008.00554.x. PMID 19207876.
  6. ^ Dang Z. C.; Löwik, C. (2005). "Dose-dependent effects of phytoestrogens on bone: Molecular mechanisms". Trends in Endocrinology and Metabolism. 16 (5): 207–213. doi:10.1016/j.tem.2005.05.001. PMID 15922618.{{cite journal}}: CS1 maint: multiple names: authors list (link)
  7. ^ Messina, M.; Wu, A. H. (2009). "Perspectives on the soy-breast cancer relation". American Journal of Clinical Nutrition. 89 (5): 1673S–1679S. doi:10.3945/ajcn.2009.26736V. PMID 19339397.{{cite journal}}: CS1 maint: multiple names: authors list (link)
  8. ^ de Lemos, M. L. (2001). "Effects of soy phytoestrogens genistein and daidzein on breast cancer growth". Annals of Pharmacotherapy. 35 (9): 11118–11121. doi:10.1345/aph.10257. PMID 11573864.
  9. ^ Tonetti, D. A.; Zhang, Y.; Zhao, H.; Lim, S. B.; Constantinou, A. I. (2007). "The effect of the phytoestrogens genistein, daidzein, and equol on the growth of tamoxifen-resistant T47D / PKCα". Nutrition and Cancer. 58 (2): 1222–1229. doi:10.1080/01635580701328545. PMID 17640169.{{cite journal}}: CS1 maint: multiple names: authors list (link)
  10. ^ Guha, N.; Kwan, M. L.; Quesenberry, C. P. Jr.; Weltzien, E. K.; Castillo, A. L.; Caan, B. J. (2009). "Soy Isoflavones and Risk of Cancer Recurrence in a Cohort of Breast Cancer Survivors: The Life After Cancer Epidemiology Study". Breast Cancer Research and Treatment. 118 (2): 395–405. doi:10.1007/s10549-009-0321-5. PMID 19221874.{{cite journal}}: CS1 maint: multiple names: authors list (link)
  11. ^ Jin, S.; Zhang, Q. Y.; Kang, X. M.; Wang, J. X.; Zhao, W. H. (2010). "Daidzein induces MCF-7 breast cancer cell apoptosis via the mitochondrial pathway". Annals of Oncology. 21 (2): 263–268. doi:10.1093/annonc/mdp499. PMID 19889614.{{cite journal}}: CS1 maint: multiple names: authors list (link)
  12. ^ Trock, B. J. (2006). "Meta-Analysis of Soy Intake and Breast Cancer Risk". Journal of the National Cancer Institute. 98 (7): 459–471. doi:10.1093/jnci/djj102. PMID 16595782. {{cite journal}}: Unknown parameter |coauthors= ignored (|author= suggested) (help)
  13. ^ Horn-Ross, P. L. (2003). "Phytoestrogen Intake and Endometrial Cancer Risk". Journal of the National Cancer Institute. 95 (15): 1158–1164. doi:10.1093/jnci/djg015. PMID 12902445. {{cite journal}}: Unknown parameter |coauthors= ignored (|author= suggested) (help)
  14. ^ Steinberg, F. M. (2011). "Clinical outcomes of a 2-y soy isoflavone supplementation in menopausal women" (pdf). The American Journal of Clinical Nutrition. 93 (2): 356–367. doi:10.3945/​ajcn.110.008359. PMC 3021428. PMID 21177797. {{cite journal}}: Unknown parameter |coauthors= ignored (|author= suggested) (help); zero width space character in |doi= at position 9 (help)
  15. ^ Maskarinec, G. (2009). "Various Doses of Soy Isoflavones do not Modify Mammographic Density in Postmenopausal Women" (pdf). The Journal of Nutrition. 139 (5): 981–986. doi:10.3945/​jn.108.102913. PMC 2714394. PMID 19321587. {{cite journal}}: Unknown parameter |coauthors= ignored (|author= suggested) (help); zero width space character in |doi= at position 9 (help)
  16. ^ Levis, S. (2011). "Soy isoflavones in the prevention of menopausal bone loss and menopausal symptoms: a randomized, double-blind trial". Archives of Internal Medicine. 171 (15): 1363–1369. doi:10.1001/archinternmed.2011.330. PMID 21824950. {{cite journal}}: Unknown parameter |coauthors= ignored (|author= suggested) (help)
  17. ^ Röhrdanz, E.; Ohler, S.; Tran-Thi, Q. H.; Kahl, R. (2002). "The Phytoestrogen Daidzein Affects the Antioxidant Enzyme System of Rat Hepatoma H4IIE Cells" (pdf). Journal of Nutrition. 132 (2): 370–375. PMID 11880557.{{cite journal}}: CS1 maint: multiple names: authors list (link)
  18. ^ Setchell, K. D. (2010). "Equol: History, Chemistry, and Formation" (pdf). The Journal of Nutrition. 140 (7): 1355S–1362S. doi:10.3945/jn.109.119776. PMC 2884333. PMID 20519412. {{cite journal}}: Unknown parameter |coauthors= ignored (|author= suggested) (help)
  19. ^ a b c d Atkinson, C. (2005). "Gut bacterial metabolism of the soy isoflavone daidzein: exploring the relevance to human health" (pdf). Experimental Biology and Medicine. 230 (3): 155–170. PMID 15734719. {{cite journal}}: Unknown parameter |coauthors= ignored (|author= suggested) (help)
  20. ^ Lampe, J. W. (1998). "Urinary Equol Excretion with a Soy Challenge: Influence of Habitual Diet". Proceedings of the Society for Experimental Biology and Medicine. 217 (3): 335–339. PMID 9492344. {{cite journal}}: Unknown parameter |coauthors= ignored (|author= suggested) (help)
  21. ^ Setchell, K. D. (2006). "Method of Defining Equol-Producer Status and its Frequency among Vegetarians" (pdf). The Journal of Nutrition. 136 (8): 2188–2193. PMID 16857839. {{cite journal}}: Unknown parameter |coauthors= ignored (|author= suggested) (help)
  22. ^ Rowland, I. R. (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. {{cite journal}}: Unknown parameter |coauthors= ignored (|author= suggested) (help)
  23. ^ Watanabe, S. (1998). "Pharmacokinetics of Soybean Isoflavones in Plasma, Urine and Feces of Men after Ingestion of 60 g Baked Soybean Powder (Kinako)" (pdf). The Journal of Nutrition. 128 (10): 1710–1715. PMID 9772140. {{cite journal}}: Unknown parameter |coauthors= ignored (|author= suggested) (help)
  24. ^ Arai, Y. (2000). "Comparison of Isoflavones among Dietary Intake, Plasma Concentration and Urinary Excretion for Accurate Estimation of Phytoestrogen Intake" (pdf). Journal of Epidemiology. 10 (2): 127–135. PMID 10778038. {{cite journal}}: Unknown parameter |coauthors= ignored (|author= suggested) (help)
  25. ^ Attention: This template ({{cite pmid}}) is deprecated. To cite the publication identified by PMID 15067102 , please use {{cite journal}} with |pmid= 15067102 instead.
  26. ^ Song, K. B. (2006). "Prevalence of Daidzein-Metabolizing Phenotypes Differs between Caucasian and Korean American Women and Girls" (pdf). The Journal of Nutrition. 136 (5): 1347–1351. PMID 16614428. {{cite journal}}: Unknown parameter |coauthors= ignored (|author= suggested) (help)
  27. ^ a b Avis, N. E. (2001). "Is there a Menopausal Syndrome? Menopausal Status and Symptoms across Racial / Ethnic Groups". Social Science & Medicine. 52 (3): 345–356. PMID 11330770. {{cite journal}}: Unknown parameter |coauthors= ignored (|author= suggested) (help)
  28. ^ Aso, T. (2012). "A natural S-equol supplement alleviates hot flushes and other menopausal symptoms in equol nonproducing postmenopausal Japanese women". Journal of Women's Health. 21 (1): 92–100. doi:10.1089/jwh.2011.2753. PMID 21992596. {{cite journal}}: Unknown parameter |coauthors= ignored (|author= suggested) (help)
  29. ^ Yoneda, T. (2011). "S-equol and the fermented soy product SE5-OH containing S-equol similarly decrease ovariectomy-induced increase in rat tail skin temperature in an animal model of hot flushes". Menopause. 18 (7): 814–820. doi:10.1097/gme.0b013e318208fb0d. PMID 21451423. {{cite journal}}: Unknown parameter |coauthors= ignored (|author= suggested) (help)
  30. ^ Jou, H. J. (2008). "Effect of intestinal production of equol on menopausal symptoms in women treated with soy isoflavones". International Journal of Gynaecology and Obstetrics. 102 (1): 44–49. doi:10.1016/j.ijgo.2008.01.028. PMID 18395723. {{cite journal}}: Unknown parameter |coauthors= ignored (|author= suggested) (help)
  31. ^ Wu, J. (2007). "Possible role of equol status in the effects of isoflavone on bone and fat mass in postmenopausal Japanese women: a double-blind, randomized, controlled trial". Menopause. 14 (5): 866–874. doi:10.1097/gme.0b013e3180305299. PMID 17464237. {{cite journal}}: Unknown parameter |coauthors= ignored (|author= suggested) (help)
  32. ^ Tousen, Y. (2011). "Natural S-Equol Decreases Bone Resorption in Postmenopausal, Non-Equol-Producing Japanese Women: A Pilot Randomized, Placebo-Controlled Trial". Menopause. 18 (5): 563–574. doi:10.1097/gme.0b013e3181f85aa7. PMID 21252728. {{cite journal}}: Unknown parameter |coauthors= ignored (|author= suggested) (help)
  33. ^ Setchell, K. D. (2002). "The Clinical Importance of the Metabolite Equol - A clue to the Effectiveness of Soy and its Isoflavones" (pdf). The Journal of Nutrition. 132 (12): 3577–3584. PMID 12468591. {{cite journal}}: Unknown parameter |coauthors= ignored (|author= suggested) (help)
  34. ^ Kudo, Y. (2005). "A Comparative Study on Menopausal Status and Climacteric Complaints of Japanese Women in Urban and Rural Area by Cross-Sectional, Community Based Survey". Journal of the Japan Menopause Society. 13: 47–54. {{cite journal}}: Unknown parameter |coauthors= ignored (|author= suggested) (help)
  35. ^ Uchiyama, S. (2007). "The Cross-Sectional Study of the Relationship between Soy Isoflavones, Equol and the Menopausal Symptoms in Japanese Women". Journal of the Japan Menopause Society. 15: 28–37. {{cite journal}}: Unknown parameter |coauthors= ignored (|author= suggested) (help)
  36. ^ Chen, G.; Zhang, J.; Ye, J. (2001). "Determination of Puerarin, Daidzein and Rutin in Pueraria lobata (Willd.) Ohwi by Capillary Electrophoresis with Electrochemical Detection". Journal of Chromatography A. 923 (1–2): 255–262. doi:10.1016/S0021-9673(01)00996-7. PMID 11510548.
  37. ^ Xu, H.-N.; He, C.-H. (2007). "Extraction of Isoflavones from Stem of Pueraria lobata (Willd.) Ohwi Using n-Butanol / Water Two-Phase Solvent System and Separation of Daidzein". Separation and Purification Technology. 56 (1): 255–262. doi:10.1016/j.seppur.2007.01.027.{{cite journal}}: CS1 maint: multiple names: authors list (link)
  38. ^ Zhou, H. Y.; Wang, J. H.; Yan, F. Y. (2007). Zhongguo Zhong Yao Za Zhi (in Chinese). 32 (10): 937–939. PMID 17655152. {{cite journal}}: Missing or empty |title= (help); Unknown parameter |trans_title= ignored (|trans-title= suggested) (help)CS1 maint: multiple names: authors list (link)

Retrieved from "https://en.wikipedia.org/w/index.php?title=Daidzein&oldid=506206528"