(+/-)-EQUOL

그림문자(GHS)

• 그림문자(GHS)

  

• 신호 어

  Warning

• 유해·위험 문구

  H302：삼키면 유해함

  H315：피부에 자극을 일으킴

  H319：눈에 심한 자극을 일으킴

  H332：흡입하면 유해함

  H335：호흡 자극성을 일으킬 수 있음

• 예방조치문구

  P261：분진·흄·가스·미스트·증기·...·스프레이의 흡입을 피하시오.

  P280：보호장갑/보호의/보안경/안면보호구를 착용하시오.

  P305+P351+P338：눈에 묻으면 몇 분간 물로 조심해서 씻으시오. 가능하면 콘택트렌즈를 제거하시오. 계속 씻으시오.

(+/-)-EQUOL 화학적 특성, 용도, 생산

• 개요

  Equol is a nonsteroidal estrogen produced from the metabolism of the isoflavonoid phytoestrogen daidzein by human intestinal microflora. The estrogen receptor (ER) binding activity of the naturally occurring (S)-enantiomer demonstrates greater affinity toward ERβ while the (R)-enantiomer demonstrates greater affinity towards ERα. Synthesized as a racemic mixture, (±)-equol exhibits EC50 values of 200 and 74 nM for human ERα and ERβ, respectively and induces breast cancer cell proliferation in vitro at concentrations as low as 100 nM.

• 화학적 성질

  White to Off-White Solid

• 용도

  (+/-)-Equol exhibits EC50 values of 200 and 74 nM for human ERα and ERβ, respectively and induces breast cancer cell proliferation in vitro at concentrations as low as 100 nM. It is a weak estrogenic agonist, and competitive inhibitor of 17β-estradiol at the estradiol receptor. It inhibits 12-O-tetradecanoylphorbol 13-acetate (TPA)-induced neoplastic cell transformation by targeting the MEK/ERK/p90RSK/activator protein-1 signalling pathway. It functions as a DHT blocker.

• 주요 응용

  (±)-Equol is a metabolite produced in vivo from the soy phytoestrogen daidzein by the action of certain gut microflora, and is a nonsteroidal estrogen of the isoflavonoid class. (±)-Equo has been reported to have estrogenic activity and affinity for estrogen receptors. (±)-Equo can exist in two enantiomeric forms, (S)-equol and (R)-equol. In binding assays, (S)-equol has a higher binding affinity for estrogen β receptors.

• 생물학적 활성

  Metabolite of daidzein. Weak estrogenic agonist, and competitive inhibitor of 17β-estradiol at the estradiol receptor.
  (R,S)-Equol is a flavonoid. Racemic mixture. This is a metabolite that is produced in vivo from soy phytoestrogen daidzein from gut microflora. (R,S)-Equol inhibits 12-O-tetradecanoylphorbol 13-acetate (TPA)-induced neoplastic cell transformation by targeting the MEK/ERK/p90RSK/activator protein-1 signalling pathway. (R,S)-Equol shows positive effects on the incidence of prostate cancer. Functions as a DHT blocker. Preferentially activates estrogen receptor β (ERβ).

• 참고 문헌

  Equol, a natural estrogenic metabolite from soy isoflavones convenient preparation and resolution of R- and S-equols and their differing binding and biological activity through estrogen receptors alpha and beta
  R. S. Muthyala, Y. H. Ju, S. Sheng, L. D. Williams, D. R. Doerge, B. S. Katzenellenbogen, W. G. Helferich, J. A. Katzenellenbogen, Bioorg. Med. Chem. 2004, 12, 1559.
  Isolation and identification of new bacterial stains producing equol from Pueraria lobate extract fermentation
  J. E. Kwon, J. Lim, I. Kim, D. Kim, S. C. Kang, PLoS ONE 2018, 13, e0192490.
  Setchell, K.D.R., Clerici, C., Lephart, E.D., et al. S-equol, a potent ligand for estrogen receptor β, is the exclusive enantiomeric form of the soy isoflavone metabolite produced by human intestinal bacterial flora. Am. J. Clin. Nutr. 81(5), 1072-1079 (2005).
  Liu, H., Du, J., Hu, C., et al. Delayed activation of extracellular-signal-regulated kinase ? is involved in genistein- and equol-induced cell proliferation and estrogen-receptor-α-mediated transcription in MCF-7 breast cancer cells. Journal of Nutritional Biochemistry (2009).

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