Genisteïne

	Genisteïne
	Structuurformule en molecuulmodel
	Structuurformule van genisteïne
	Algemeen
Molecuulformule; (uitleg)	C15H10O5
IUPAC-naam	5,7-dihydroxy-3-(4-hydroxyfenyl)chromen-4-on
Molmassa	270,2369 g/mol
SMILES	C1=CC(=CC=C1C2=COC3=CC(=CC(=C3C2=O)O)O)O
InChI	1S/C15H10O5/c16-9-3-1-8(2-4-9)11-7-20-13-6-10(17)5-12(18)14(13)15(11)19/h1-7,16-18H
CAS-nummer	446-72-0
PubChem	5280961
	Waarschuwingen en veiligheidsmaatregelen
Waarschuwing
H-zinnen	H302
EUH-zinnen	geen
P-zinnen	geen
Portaal	Scheikunde

Genisteïne behoort tot de fyto-oestrogenen, komt voor in planten zoals soja[1] en vertoont een werking zoals het vrouwelijk hormoon oestrogeen.

De stof behoort tot de isoflavonen.

Effect op vrouwen

Genisteïne werkt als oestrogeen en kan de ontwikkeling en het behoud van vrouwelijke kenmerken bevorderen. Genisteïne kan de ontwikkeling van een al aanwezige borstkanker bevorderen voor zover die gevoelig is voor oestrogeen.[2][3][4][5][6]

Effect op mannen

Genisteïne veroorzaakt het apoptose van cellen in de teelballen en kan zo mannelijke vruchtbaarheid en mannelijke kenmerken verminderen.[7] Genisteïne kan de ontwikkeling van prostaatkanker remmen.[8]

Aderverkalking

Genisteïne gaat aderverkalking tegen.[9][10]

Schildklier

Genisteïne vermindert de werking van de schildklier.[11]

Bronnen, noten en/of referenties

(en) L.U. Thompson, B.A. Boucher, Z. Liu, M. Cotterchio & N. Kreiger (2006) – Phytoestrogen content of foods consumed in Canada, including isoflavones, lignans, and coumestan, Nutr. Cancer., 54 (2), pp. 184-201
(en) L. Hilakivi-Clarke, E. Cho, I. Onojafe, M. Raygada & R. Clarke (1999) – Maternal exposure to genistein during pregnancy increases carcinogen-induced mammary tumorigenesis in female rat offspring, Oncol. Rep., 6 (5), 1089-1095
(en) W.F. Chen & M.S. Wong (2004) – Genistein enhances insulin-like growth factor signaling pathway in human breast cancer (MCF-7) cells, J. Clin. Endocrinol. Metab., 89 (5), pp. 2351-2359
(en) S. De Assis & L. Hilakivi-Clarke (2006) – Timing of dietary estrogenic exposures and breast cancer risk, Ann. NY Acad. Sci., 1089, pp. 14-35
(en) Y.H. Ju, K.F. Allred, C.D. Allred & W.G. Helferich (2006) – Genistein stimulates growth of human breast cancer cells in a novel, postmenopausal animal model, with low plasma estradiol concentrations, Carcinogenesis, 27 (6), pp. 1292-1299
(en) M. Messina, W. McCaskill-Stevens & J.W. Lampe (2006) – Addressing the soy and breast cancer relationship: review, commentary, and workshop proceedings, J. Natl. Cancer Inst., 98 (18), pp. 1275-1284
(en) J. Kumi-Diaka, R. Rodriguez & G. Goudaze (1998) – Influence of genistein (4',5,7-trihydroxyisoflavone) on the growth and proliferation of testicular cell lines, Biol. Cell., 90 (4), pp. 349-354
(en) B.L. Dillingham, B.L. McVeigh, J.W. Lampe & A.M. Duncan (2005) – Soy protein isolates of varying isoflavone content exert minor effects on serum reproductive hormones in healthy young men, J. Nutr., 135 (3), pp. 584-591
(en) D. Liu, L.L. Homan & J.S. Dillon (2004) – Genistein acutely stimulates nitric oxide synthesis in vascular endothelial cells by a cyclic adenosine 5'-monophosphate-dependent mechanism, Endocrinology, 145 (12), pp. 5532-5539
(en) H. Si & D. Liu (2007) – Phytochemical genistein in the regulation of vascular function: new insights, Curr. Med. Chem., 14 (24), pp. 2581-2589
(en) S. Yellayi, A. Naaz, M.A. Szewczykowski, T. Sato, J.A. Woods, J. Chang, M. Segre, C.D. Allred, W.G. Helferich & P.S. Cooke (2002) – The phytoestrogen genistein induces thymic and immune changes: A human health concern?, Proceedings of the National Academy of Sciences of the United States of America, 99 (11), pp. 7616-7621

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[1] (en) L.U. Thompson, B.A. Boucher, Z. Liu, M. Cotterchio & N. Kreiger (2006) – Phytoestrogen content of foods consumed in Canada, including isoflavones, lignans, and coumestan, Nutr. Cancer., 54 (2), pp. 184-201

[2] (en) L. Hilakivi-Clarke, E. Cho, I. Onojafe, M. Raygada & R. Clarke (1999) – Maternal exposure to genistein during pregnancy increases carcinogen-induced mammary tumorigenesis in female rat offspring, Oncol. Rep., 6 (5), 1089-1095

[3] (en) W.F. Chen & M.S. Wong (2004) – Genistein enhances insulin-like growth factor signaling pathway in human breast cancer (MCF-7) cells, J. Clin. Endocrinol. Metab., 89 (5), pp. 2351-2359

[4] (en) S. De Assis & L. Hilakivi-Clarke (2006) – Timing of dietary estrogenic exposures and breast cancer risk, Ann. NY Acad. Sci., 1089, pp. 14-35

[5] (en) Y.H. Ju, K.F. Allred, C.D. Allred & W.G. Helferich (2006) – Genistein stimulates growth of human breast cancer cells in a novel, postmenopausal animal model, with low plasma estradiol concentrations, Carcinogenesis, 27 (6), pp. 1292-1299

[6] (en) M. Messina, W. McCaskill-Stevens & J.W. Lampe (2006) – Addressing the soy and breast cancer relationship: review, commentary, and workshop proceedings, J. Natl. Cancer Inst., 98 (18), pp. 1275-1284

[7] (en) J. Kumi-Diaka, R. Rodriguez & G. Goudaze (1998) – Influence of genistein (4',5,7-trihydroxyisoflavone) on the growth and proliferation of testicular cell lines, Biol. Cell., 90 (4), pp. 349-354

[8] (en) B.L. Dillingham, B.L. McVeigh, J.W. Lampe & A.M. Duncan (2005) – Soy protein isolates of varying isoflavone content exert minor effects on serum reproductive hormones in healthy young men, J. Nutr., 135 (3), pp. 584-591

[9] (en) D. Liu, L.L. Homan & J.S. Dillon (2004) – Genistein acutely stimulates nitric oxide synthesis in vascular endothelial cells by a cyclic adenosine 5'-monophosphate-dependent mechanism, Endocrinology, 145 (12), pp. 5532-5539

[10] (en) H. Si & D. Liu (2007) – Phytochemical genistein in the regulation of vascular function: new insights, Curr. Med. Chem., 14 (24), pp. 2581-2589

[11] (en) S. Yellayi, A. Naaz, M.A. Szewczykowski, T. Sato, J.A. Woods, J. Chang, M. Segre, C.D. Allred, W.G. Helferich & P.S. Cooke (2002) – The phytoestrogen genistein induces thymic and immune changes: A human health concern?, Proceedings of the National Academy of Sciences of the United States of America, 99 (11), pp. 7616-7621