(±)-Equol: Structure, Benefits and Side Effects

(±)-Equol is an isoflavone metabolite formed from daidzein/daidzein by bacteria in the small intestine and distal colonic regions. Chemically, equol (4’,7-isoflavanediol) is an equol flavanol structure with a non-planar structure, optically active, and an asymmetric carbon atom at the C3 position, yielding R(-)- and S(-)-equol enantiomers. However, only S(-)-equol has been detected as a result of bacterial daidzein conversion. It is more stable, more readily absorbed, and has a lower clearance rate than its precursor molecule daidzein. It also exhibits more potent estrogenic activity than any other isoflavone or isoflavone-derived metabolite.

Benefits

(±)-Equol has high antioxidant and estrogenic activities and is believed to have many beneficial effects on human health. It reduces the incidence of estrogen-dependent and aging-related diseases such as menopausal symptoms, osteoporosis, cardiovascular disease, and cancer in women. Women who took S(-)-equol supplements (10 to 30 mg daily for 8-12 weeks) reported benefits in terms of major menopausal symptoms (hot flashes) and arteriosclerosis.

In mice, equol has been shown to reduce the expression of genes associated with inhibition of bone formation, osteoclast and immature osteoblast specificity, and cartilage destruction. In humans, postmenopausal women taking 10 mg of equol daily for one year were protected against whole-body bone mineral density loss. Studies have reported that in men, the ability to produce equol or equol itself is thought to help reduce the incidence of prostate cancer. In addition, a diet based on soy isoflavones may help prevent prostate cancer.

Effects of (±)-Equol on the Skin

Topical interventions with equol have shown that equol has anti-aging effects on the skin of postmenopausal women, reducing the area and depth of wrinkles. Recently, equol application to the skin has also been associated with improvements in skin roughness, texture, and smoothness, as well as improvements in some epigenetic molecular markers in skin cells (LINE-1 methylation and telomere length). However, the effectiveness in clinical practice needs further investigation.

Side Effects

(±)-Equol is probably safe when taken orally for one year when used as a supplement. Common side effects are constipation, bloating, and dizziness, which are generally mild and gradually improve after discontinuation of the drug. Use with caution in people who are allergic to the substance, as it may cause allergic reactions, including rash and itching in some people.

References:

[1] BALTASAR MAYO; Ana B F; Lucía Vázquez. Equol: A Bacterial Metabolite from The Daidzein Isoflavone and Its Presumed Beneficial Health Effects.[J]. ACS Applied Energy Materials, 2019. DOI:10.3390/nu11092231.

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