Identification of the potent phytoestrogen glycinol in elicited soybean (glycine max)

Endocrinology

Volumn 150, Issue 5, 2009, Pages 2446-2453

  Boue, Stephen M ^a   Tilghman, Syreeta L ^b,c,d,e   Elliott, Steven ^b,e   Zimmerman, M Carla ^c   Williams, K Y ^e   Payton Stewart, Florastina ^b,d   Miraflor, Allen P ^c   Howell, Melanie H ^c   Shih, Betty Y ^a   Carter Wientjes, Carol H ^a   Segar, Chris ^f   Beckman, Barbara S ^c,e   Wiese, Thomas E ^e,f   Cleveland, Thomas E ^a   McLachlan, John A ^c,d,e   Burow, Matthew E ^b,c,d,e  

^a SOUTHERN REGIONAL RESEARCH CENTER   (United States)

^b Section of Hematology and Medical Oncology   (United States)

^c Department of Pulmonary Diseases Critical Care and Environmental Medicine ^*  (United States)

^d TULANE UNIVERSITY SCHOOL OF MEDICINE   (United States)

^e TULANE UNIVERSITY HEALTH SCIENCES CENTER   (United States)

^f XAVIER UNIVERSITY OF LOUISIANA   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

ESTROGEN; ESTROGEN RECEPTOR ALPHA; ESTROGEN RECEPTOR BETA; FULVESTRANT; GLYCINOL; ISOFLAVONE DERIVATIVE; MESSENGER RNA; PHYTOESTROGEN; PROGESTERONE RECEPTOR; STROMAL CELL DERIVED FACTOR 1; UNCLASSIFIED DRUG; ESTROGEN RECEPTOR; FLAVONOL DERIVATIVE; GLYCEOLLIN; PTEROCARPAN DERIVATIVE;

ARTICLE; BINDING AFFINITY; BIOASSAY; CELL STRAIN MCF 7; COLONY FORMATION; CONCENTRATION RESPONSE; CONTROLLED STUDY; DRUG ACTIVITY; DRUG BINDING; DRUG IDENTIFICATION; DRUG ISOLATION; DRUG POTENCY; DRUG STRUCTURE; ESTROGEN RESPONSIVE ELEMENT; GENE EXPRESSION; HUMAN; HUMAN CELL; IN VITRO STUDY; MOLECULAR DOCKING; PRIORITY JOURNAL; SIGNAL TRANSDUCTION; SOYBEAN; BINDING COMPETITION; BIOLOGICAL MODEL; CELL CULTURE; CELL PROLIFERATION; CHEMICAL STRUCTURE; CHEMISTRY; DRUG EFFECT; DRUG SCREENING; FERMENTATION; GENE EXPRESSION REGULATION; GENETIC TRANSCRIPTION; ISOLATION AND PURIFICATION; METABOLISM; PHYSIOLOGY;

BINDING, COMPETITIVE; CELL PROLIFERATION; CELLS, CULTURED; DRUG EVALUATION, PRECLINICAL; ESTROGENS; FERMENTATION; FLAVONOLS; GENE EXPRESSION REGULATION; HUMANS; MODELS, BIOLOGICAL; MODELS, MOLECULAR; PHYTOESTROGENS; PTEROCARPANS; RECEPTORS, ESTROGEN; SOYBEANS; TRANSCRIPTION, GENETIC;

EID: 66449115906     PISSN: 00137227     EISSN: 00137227     Source Type: Journal    
DOI: 10.1210/en.2008-1235     Document Type: Article

References (50)

1. Adlercreutz H 1990 Western diet and Western diseases: some hormonal and biochemical mechanisms and associations. Scand J Clin Lab Invest 50:3-23
2. Wu AH, Ziegler RG, Horn-Ross PL, Nomura AM, West DW, Kolonel LN, Rosenthal JF, Hoover RN, Pike MC 1996 Tofu and risk of breast cancer in Asian-Americans. Cancer Epidemiol Biomarkers Prev 5:901-906
3. Fournier DB, Erdman Jr JW, Gordon GB 1998Soy,itscomponents, and cancer prevention: a review of the in vitro, animal and human data. Cancer Epidemiol Biomarkers Prev 7:1055-1065
4. Baird DD, Umbach DM, Lansdell L, Hughes CL, Setchell KD, Weinberg CR, HaneyAF,Wilcox AJ, McLachlan JA 1995 Dietary in tervention study to assess estrogenicity of dietary soy among postmen opausal women. J Clin Endocrinol Metab 80:1685-1690
5. Adlercreutz H 1995 Phytoestrogens: epidemiology and a possible role in cancer protection. In: McLachlan JA, Korach KS, eds. Estrogens in the environment, III: global health implications. Environ Health Perspect 103(Suppl 7):103-112
6. Tham DM, Gardner CD, Haskell WL1998 Clinicalreview97: potentialhealth benefits of dietary phytoestrogens: a review of the clinical, epidemiological, and mechanistic evidence. J Clin Endocrinol Metab 83:2223-2235
7. Murkies AL, Wilcox G, Davis SR 1998 Clinical review 92: phytoestrogens. J Clin Endocrinol Metab 83:297-303
8. Cline JM, Hughes CL 1998 Phytochemicals for the prevention of breast and endometrial cancer. In: Foon KA, Muss HB, eds. Biological and hormonal therapies of cancer. Boston: Klewer Academic Publishers; 107-134
9. Humfrey CDN 1998 Phytoestrogens and human health effects: weighing up the current evidence. Nat Toxins 6:51-59
10. Bingham SA, Atkinson C, Liggins J, Bluck L, Coward A 1998 Phyto-estrogens: where are we now? Br J Nutr 79:393-406
11. Coward L, Smith M, Kirk M, Barnes S 1998 Chemical modification of isofla- vones in soyfoods during cooking and processing. Am J Clin Nutr 68:1486S-1491S
12. Dakora FD, Phillips DA 1996 Diverse functions of isoflavonoids in legumes transcend anti-microbial definitions of phytoalexins. Physiol Mol Plant Physiol 49:1-20
13. Darvill AG, Albersheim P 1984 Phytoalexins and their elcitors-a defense against microbial infection in plants. Ann Rev Plant Physiol 35:243-275
14. Graham TL, Kim JE, Graham MY 1990 Role of constitutive isoflavone conjugates in the accumulation of glyceollin in soybean infected with Phytoph- thora megasperma. Mol Plant Microbe Interact 3:157-166
15. Paxton JD 1991 Biosynthesis and accumulation of legume phytoalexins in Mycotoxins and Phytoalexins. In: Sharma RP, Salunkhe DK, eds. Boca Raton, FL: CRC Press; 485-499
16. Rivera-Vargas LI, Schmitthenner AF, Graham TL 1993 Soybean flavonoid effects on and metabolism by Phytophthora sojae. Phytochem 32:851-857
17. Graham TL, Graham MY 1991 Glyceollin elicitors induce major but distinctly different shifts in isoflavonoid metabolism in proximal and distal soybean cell populations. Mol Plant Microbe Interact 4:60-68
18. Banks SW, Dewick PM1983 Bio synthesis of glyceoll insI, II, and III insoybean. Phytochemistry 22):2729-2733
19. Burow ME, Boue SM, Collins-Burow BM, Melnik LI, Duong BN, Carter- Wientjes CH, Li S, Wiese TE, Cleveland TE, McLachlan JA 2001 Phytochem- ical glyceollins, isolated from soy, mediate antihormonal effects through estrogen receptor a and j. J Endocrinol 86:1750-1758
20. Salvo VA, Boue SM, Fonseca JP, Elliott S, Corbitt C, Collins-Burow BM, Curiel TJ, Srivastav SK, Shih BY, Carter-Wientjes C, Wood CE, Erhardt PW, Beckman BS, McLachlan JA, Cleveland TE, Burow ME 2006 Antiestrogenic glyceollins suppress human breast and ovarian carcinoma tumorigenesis. Clin Cancer Res 12:7159-7164
21. Wood CE, Clarkson TB, Appt SE, Franke AA, Boue SM, Burow ME, McCoy T, Cline JM 2006 Effects of soybean glyceollins and estradiol on postmenopausal female monkeys. Nutr Cancer 56:74-81
22. Moesta P, Hahn MG, Grisebach H 1983 Development of a radioimmunoassay for the soybean phytoalexin glyceollin I. Plant Physiol 73:233-237
23. Garcez WS, Martins D, Garcez FR, Marques MR, Pereira AA, Oliveira LA, Rondon JN, Peruca AD 2000 Effect of spores of saprophytic fungi on phy- toalexin accumulation in seeds of frog-eye leaf spot and stem canker-resistant and -susceptible soybean (Glycine max L.) cultivars. J Agric Food Chem 48:3662-3665
24. Weinstein LI, Hahn MG, Albersheim P 1981 Host-Pathogen Interactions XVIII. Isolation and biological activity of glycinol, a pterocarpan phytoalexin synthesized by soybeans. Plant Physiol 69:358-363
25. Lyne RL, Mulheirn LH 1978 Minor pterocarpinoids of soybean. Tetrahedron Lett 34:3127-3128
26. Weinstein LI, Albersheim P 1983 Host-Pathogen Interactions XXIII. The mechanism of the antibacterial action of glycinol, a pterocarpan phytoalexin synthesized by soybeans. Plant Physiol 72:557-563
27. Qi Y, Moco S, Boeren S, de Vos C, Bovy A 2005 Isolation and identification of glycinol form glycine max [L.] Merri. Chin J Chromatogr 23:353-357
28. Burow ME, Tang Y, Collins-Burow BM, Krajewski S, Reed JC, McLachlan JA, Beckman BS 1999 Effects of environmental estrogens on tumor necrosis factor a-mediated apoptosis in MCF-7 cells. Carcinogenesis 20:2057-2061
29. Klotz DM, Beckman BS, Hill SM, McLachlan JA, Walters MR, Arnold SF 1996 Identification of environmental chemicals with estrogenic activity using a combination of in vitro assays. Environ Health Perspect 104:84-89
30. Bolger R, Wiese TE, Ervin K, Nestich S, Checovich W 1998 Rapid screening of environmental chemicals for estrogen receptor binding capacity. Environ Health Perspect 106:551-557
31. Dewick PM, Barz W, Griesbach H 1970 Biosynthesis of coumestrol in Phaseo-lus aureus. Phytochemistry 9:775-783
32. Boue SM, Carter CH, Ehrlich KC, Cleveland TE 2000 Induction of the soybean phytoalexins coumestrol and glyceollin by Aspergillus. J Agric Food Chem 48:2167-2172
33. Hall JM, Korach KS 2003 Stromal cell-derived factor 1, a novel target of estrogen receptor action, mediates the mitogenic effects of estradiol in ovarian and breast cancer cells. Mol Endocrinol 17:792-803
34. Collins-Burow BM, Burow ME, Duong BN, McLachlan JA 2000 The estrogenic and antiestrogenic activities of flavonoid phytochemicals through estrogen receptor binding dependent and independent mechanisms. Nutr Cancer 38:229-244
35. Kuiper GG, Carlsson B, Grandien K, Enmark E, Haggblad J, Nilsson S, Gustafsson JA 1997 Comparison of the ligand binding specificity and transcript distribution of estrogen receptors α and β. Endocrinology 138:863-870
36. Barkhem T, Carlsson B, Nilsson Y, Enmark E, Gustafsson J, Nilsson S 1998 Differential response of estrogen receptor α and estrogen receptor β to partial estrogen agonists/antagonists. Mol Pharmacol 54:105-112
37. McInerney EM, Weis KE, Sun J, Mosselmam S, Katzenellenbogen BS 1998 Transcription activation by the human estrogen receptor subtype β (ER β ) studied with ERj and ERa receptor chimeras. Endocrinology139: 4513-4522
38. Wolters M, Hahn A 2004 Soy isoflavones-a therapy for menopausal symptoms? Wien Med Wochenschr 154:334-341
39. Nikov G, Hopkins NE, Boue S, Alworth W 2000 Interactions of dietary estrogens with human estrogen receptors and the effect of estrogen receptor- estrogen response element complex formation. Environ Health Perspect 108:867-372
40. Hagmann ML, Heller W, Grisebach H 1984 Induction of phytoalexin synthesis in soybean. Stereospecific 3,9-dihydropterocarpan 6a-hydrolase from elicitor-induced soybean cell cultures. Eur J Biochem 142:127-131
41. ZaliringerU,SchallerE,GrisebachH 1981 Induction of phytoalexin synthesis in soybean. Structure and reactions of naturally occurring and enzymatically prepared prenylated pterocarpans from elicitor-treated cotyledons and cell cultures of soybean. Z. Naturforsch 36:234-241
42. Oldfield JE, Fox CW, Bahn AV, Bickoff EM, Kohler GO 1966 Coumestrol in alfalfa as a factor in growth and carcass quality in lambs. J Anim Sci 25:167-174
43. Wong E, Latch GCM 1971 Coumestans in diseased white clover. Phytochemistry 10:466-468
44. O'Neil M, Adesnaya SA, Roberts MF, Pantry I 1986 Inducible isoflavonoids from the lima bean, Phaseolus lunatus. Phytochemistry 25:1315-1332
45. GutendorfB, WestendorfJ2001 Comparisonofanarrayofin vitro assaysfor the assessment of the estrogenic potential of natural and synthetic estrogens, phytoestrogens and xenoestrogens. Toxicology 166:79 -89
46. Bickoff EM, Livingston AL, Hendrickson AP, Booth AN 1962 Relative potencies of several estrogen-like compounds found in forages. J Agric Food Chem 10:410-412
47. Dodge JA, Glaesbbrook AL, Magee DE, Philips DL, Sato M, Short L, Bryant HU 1996 Environmental estrogens: effect of cholesterol lowering and bone in the ovariectomized rat. J Steroid Biochem Mol Biol 59:155-161
48. Martin PM, Horwitz KB, Ryan DS, McGuire WL 1978 Phytoestrogen interaction with estrogen receptors in human breast cancer cells. Endocrinology 103:1860 -1867
49. Whitten PL, Patisaul HB, Young LJ2002 Neuro behavioral actions of coumes- trol and related flavonoids in rodents. Neurotoxicol Teratol 24:47-54
50. Markaverich BM, Webb B, Densmore CL, Gregory RR 1995 Effects of coumestrol on estrogen receptor function and uterine growth in ovariecto- mized rats. Environ Health Perspect 103:574-581