Details of Metabolite (Meta)

General Information of Metabolite (ID: MT104)
  Meta Name
equol
  Unify Name
Equol
  Synonym    Click to Show/Hide the Detailed Synonyms of This Metabolite
AUS-131(S)-equol;(-)-(S)-Equol;(-)-Equol;(S)-(-)-4',7-Isoflavandiol;(S)-3,4-Dihydro-3-(4-hydroxyphenyl)-2H-1-benzopyran-7-ol;(S)-Equol;4',7-Dihydroxyisoflavan;4',7-Isoflavandiol;3'-Hydroxy-equol;4' Methoxy 7 isoflavanol;4'-O-Methyl equol;6'-Hydroxy-equol;Equol, 4'-O-methyl;3' Hydroxy equol;4'-Methoxy-7-isoflavanol;6' Hydroxy equol;4' O Methyl equol;(+-)-Isomer OF equol
  Molecule Type
Isoflavonoids
  Formula
C15H14O3
  Inchi Key
ADFCQWZHKCXPAJ-GFCCVEGCSA-N
  Description    Click to Show/Hide the Detailed Description of This Metabolite
Human Metabolome Database (HMDB): Equol is a metabolite of daidzein, a phytoestrogen common in the human diet and abundant in soy. Intestinal bacteria in humans can reduce daidzein to equol, and can be found in normal human urine. The clinical effectiveness of soy isoflavones may be a function of the ability to biotransform soy isoflavones to the more potent estrogenic metabolite, equol, which may enhance the actions of soy isoflavones, owing to its greater affinity for estrogen receptors, unique antiandrogenic properties, and superior antioxidant activity. However, not all individuals consuming daidzein produce equol. Only approximately one-third to one-half of the population is able to metabolize daidzein to equol. This high variability in equol production is presumably attributable to interindividual differences in the composition of the intestinal microflora, which may play an important role in the mechanisms of action of isoflavones. (PMID:17579895,17579894). Equol can be found in Bacteroides, Bifidobacterium, Enterococcus, Lactobacillus and Eggerthella.
  External Links   HMDB ID   HMDB0002209
  VMH ID   
  KEGG ID   C14131

The epigenetic modification information of this metabolite
Modification Type Molecule EM Info Cell/Tissue Type Modified sites Condition REF
DNA Methylation BRCA1 EM Info MCF-7 cells promoter Breast cancer [1], [2]
DNA Methylation BRCA1 EM Info MDA-MB-231 cells promoter Breast cancer [1], [2]
DNA Methylation BRCA2 EM Info MCF-7 cells promoter Breast cancer [1], [2]
DNA Methylation BRCA2 EM Info MDA-MB-231 cells promoter Breast cancer [1], [2]
Histone Trimethylation H3K27 EM Info MCF-7 cells ER-alpha promoter Breast cancer [3], [4]
Histone Trimethylation H3K27 EM Info MCF-7 cells ER-BETA promoter Breast cancer [3], [4]
Histone Trimethylation H3K27 EM Info MCF-7 cells P300 promoter Breast cancer [4], [5]
Histone Trimethylation H3K27 EM Info MDA-MB-231 cells P300 promoter Breast cancer [1], [6]
Histone Trimethylation H3K27 EM Info MCF-7 cells BRCA1 promoter Breast cancer [1], [2]
Histone Trimethylation H3K27 EM Info MCF-7 cells EZH2 promoter Breast cancer [1], [2]
Histone Trimethylation H3K27 EM Info MCF-7 cells SRC3 promoter Breast cancer [1], [2]
Histone Trimethylation H3K27 EM Info MDA-MB-231 cells BRCA1 promoter Breast cancer [1], [2]
Histone Trimethylation H3K27 EM Info MDA-MB-231 cells ER-alpha promoter Breast cancer [1], [2]
Histone Trimethylation H3K27 EM Info MDA-MB-231 cells ER-BETA promoter Breast cancer [1], [2]
Histone Trimethylation H3K27 EM Info MDA-MB-231 cells EZH2 promoter Breast cancer [1], [2]
Histone Trimethylation H3K27 EM Info MDA-MB-231 cells SRC3 promoter Breast cancer [1], [2]
Histone Acetylation H3K4 EM Info MCF-7 cells P300 promoter Breast cancer [3], [7]
Histone Acetylation H3K4 EM Info MCF-7 cells ER-alpha promoter Breast cancer [3], [4]
Histone Acetylation H3K4 EM Info MCF-7 cells ER-BETA promoter Breast cancer [4], [8]
Histone Acetylation H3K4 EM Info MDA-MB-231 cells P300 promoter Breast cancer [1], [6]
Histone Acetylation H3K4 EM Info MCF-7 cells BRCA1 promoter Breast cancer [1], [2]
Histone Acetylation H3K4 EM Info MCF-7 cells EZH2 promoter Breast cancer [1], [2]
Histone Acetylation H3K4 EM Info MCF-7 cells SRC3 promoter Breast cancer [1], [2]
Histone Acetylation H3K4 EM Info MDA-MB-231 cells BRCA1 promoter Breast cancer [1], [2]
Histone Acetylation H3K4 EM Info MDA-MB-231 cells ER-alpha promoter Breast cancer [1], [2]
Histone Acetylation H3K4 EM Info MDA-MB-231 cells ER-BETA promoter Breast cancer [1], [2]
Histone Acetylation H3K4 EM Info MDA-MB-231 cells EZH2 promoter Breast cancer [1], [2]
Histone Acetylation H3K4 EM Info MDA-MB-231 cells SRC3 promoter Breast cancer [1], [2]
Histone Trimethylation H3K9 EM Info MCF-7 cells ER-alpha promoter Breast cancer [3], [4]
Histone Trimethylation H3K9 EM Info MCF-7 cells ER-BETA promoter Breast cancer [4], [8]
Histone Trimethylation H3K9 EM Info MCF-7 cells BRCA1 promoter Breast cancer [1], [2]
Histone Trimethylation H3K9 EM Info MCF-7 cells EZH2 promoter Breast cancer [1], [2]
Histone Trimethylation H3K9 EM Info MCF-7 cells P300 promoter Breast cancer [1], [2]
Histone Trimethylation H3K9 EM Info MCF-7 cells SRC3 promoter Breast cancer [1], [2]
Histone Trimethylation H3K9 EM Info MDA-MB-231 cells BRCA1 promoter Breast cancer [1], [2]
Histone Trimethylation H3K9 EM Info MDA-MB-231 cells ER-alpha promoter Breast cancer [1], [2]
Histone Trimethylation H3K9 EM Info MDA-MB-231 cells ER-BETA promoter Breast cancer [1], [2]
Histone Trimethylation H3K9 EM Info MDA-MB-231 cells EZH2 promoter Breast cancer [1], [2]
Histone Trimethylation H3K9 EM Info MDA-MB-231 cells P300 promoter Breast cancer [1], [2]
Histone Trimethylation H3K9 EM Info MDA-MB-231 cells SRC3 promoter Breast cancer [1], [2]
Histone Acetylation H4K8 EM Info MCF-7 cells ER-alpha promoter Breast cancer [3], [4]
Histone Acetylation H4K8 EM Info MCF-7 cells ER-BETA promoter Breast cancer [4], [5]
Histone Acetylation H4K8 EM Info MCF-7 cells BRCA1 promoter Breast cancer [1], [2]
Histone Acetylation H4K8 EM Info MCF-7 cells EZH2 promoter Breast cancer [1], [2]
Histone Acetylation H4K8 EM Info MCF-7 cells P300 promoter Breast cancer [1], [2]
Histone Acetylation H4K8 EM Info MCF-7 cells SRC3 promoter Breast cancer [1], [2]
Histone Acetylation H4K8 EM Info MDA-MB-231 cells BRCA1 promoter Breast cancer [1], [2]
Histone Acetylation H4K8 EM Info MDA-MB-231 cells ER-alpha promoter Breast cancer [1], [2]
Histone Acetylation H4K8 EM Info MDA-MB-231 cells ER-BETA promoter Breast cancer [1], [2]
Histone Acetylation H4K8 EM Info MDA-MB-231 cells EZH2 promoter Breast cancer [1], [2]
Histone Acetylation H4K8 EM Info MDA-MB-231 cells P300 promoter Breast cancer [1], [2]
Histone Acetylation H4K8 EM Info MDA-MB-231 cells SRC3 promoter Breast cancer [1], [2]

The microbes that produce this metabolite
      Bacteroides ovatus
         Detailed Information MIC Info click to show the detail information of this Microbiota [1], [2]
         Description
Bacteroides ovatus is an obligate anaerobic, gram-negative common human gut bacteria. It is part of the normal human gut flora, however it is the least common of the Bacteroides intestinal isolates. It has also been associated with Coeliac disease.

References
1 Daidzein Intake Is Associated with Equol Producing Status through an Increase in the Intestinal Bacteria Responsible for Equol Production. Nutrients. 2019 Feb 19;11(2):433. doi: 10.3390/nu11020433.
2 Histone lysine trimethylation or acetylation can be modulated by phytoestrogen, estrogen or anti-HDAC in breast cancer cell lines. Epigenomics. 2013 Feb;5(1):51-63. doi: 10.2217/epi.12.74.
3 Dietary metabolites derived from gut microbiota: critical modulators of epigenetic changes in mammals. Nutr Rev. 2017 May 1;75(5):374-389. doi: 10.1093/nutrit/nux001.
4 Total Lipopolysaccharide from the Human Gut Microbiome Silences Toll-Like Receptor Signaling mSystems. 2017 Nov 14;2(6):e00046-17. doi: 10.1128/mSystems.00046-17. eCollection 2017 Nov-Dec.
5 Transforming growth factor-beta 1 inhibits non-pathogenic Gram negative bacteria-induced NF-kappa B recruitment to the interleukin-6 gene promoter in intestinal epithelial cells through modulation of histone acetylation J Biol Chem. 2003 Jun 27;278(26):23851-60. doi: 10.1074/jbc.M300075200. Epub 2003 Apr 2.
6 Epigenetic modulation of BRCA1 and BRCA2 gene expression by equol in breast cancer cell lines. Br J Nutr. 2012 Oct;108(7):1187-93. doi: 10.1017/S000711451100657X. Epub 2012 Jan 5.
7 p-Cresyl Sulfate. Toxins (Basel). 2017 Jan 29;9(2):52. doi: 10.3390/toxins9020052.
8 Epigenetic Modifications of Histones in Periodontal Disease. J Dent Res. 2016 Feb;95(2):215-22. doi: 10.1177/0022034515611876. Epub 2015 Oct 23.

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