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isoflavone
3-phenyl-4H-1-benzopyran-4-one. C15 H10 O2, melting point 148 C UV(max) 245 nm (log e 4.41), 307 nm (log e 3.82)
One of the 3 classes of phytoestrogens. Enriched in soy, chickpeas, red clover & coffee.
The 2 major forms of isoflavones genistein & daidzein are formed from precursors genistin & daidzin.
Uses:
- treatment of menopausal symptoms [6]
Contraindications:
- avoid high doses in women with breast cancer
Adverse effects:
- high doses > 150 mg/day for 5 year may result in endometrial hyperplasia [4]
Mechanism of action:
1) diminishes LDL cholesterol
2) reduces menopausal symptoms [5]
3) no improvement in plasma lipids in postmenopausal women [3]
4) small improvement in bone mineral density in postmenopausal women [3]
Interactions
drug adverse effects of estrogens
Related
phytoestrogen
soy bean (Tofu, Tempe)
Specific
daidzein
equol
fisetin
genistein
isoflavonoid
General
flavone
ketone
Properties
SIZE: MW = 222.2 G/MOL
Database Correlations
PUBCHEM cid=72304
References
- Journal Watch 22(9):70-71, 2002
Hann LL et al, Obstet Gynecol, 99 389, 2002
- Merck Index, I2th ed, Merck & Co, Rahway NJ, 1996 # 5189
- Journal Watch 24(16):130, 2004
Kreijkamp-Kaspers S, Kok L, Grobbee DE, de Haan EH, Aleman A,
Lampe JW, van der Schouw YT.
Effect of soy protein containing isoflavones on cognitive
function, bone mineral density, and plasma lipids in
postmenopausal women: a randomized controlled trial.
JAMA. 2004 Jul 7;292(1):65-74.
PMID: 15238592
- Prescriber's Letter 11(9): 2004
Soy for Preventing Aging Effects in Older Women
Detail-Document#: 200914
(subscription needed) http://www.prescribersletter.com
- Bolanos R, Del Castillo A, Francia J.
Soy isoflavones versus placebo in the treatment of climacteric
vasomotor symptoms: systematic review and meta-analysis.
Menopause. 2010 May-Jun;17(3):660-6. Review.
PMID: 20464785
- Medical Knowledge Self Assessment Program (MKSAP) 18,
American College of Physicians, Philadelphia 2018
Component-of
Avlimil
Trifolium pratense, red clover (Promensil)