PMC

Concentration-dependent rate of metabolic conversion of estragole in incubations with Chinese (a) or Caucasian (b) liver microsomes. Data points represent mean values ± SEM of three individual experiments for each metabolite, including estragole-2′,3′-oxide (closed upward triangle), 1′-hydroxyestragole (closed circle), 3′-hydroxyanethole (closed square), 4-allylphenol (closed downward triangle), and M5 (closed diamond)

1–2-oxo-propanal; 4 –hydroxyacetaldehyde; 6 –acetic acid; 7–1-hydroxy-propan-2-one; 11–3-hydroxypropanal; 14 –CH₃-CO-CHOH-CHO; 15 –CHO-CH₂-CH₂-CHO; 16 –furfural; 17–2-cyclopenten-1-one; 21–2-hydroxy-2-cyclopenten-1-one; 22 –dihydro-methyl furanone isomer; 27 – 5H-furan-2-one; 28–4-hydroxy-5,6-dihydro-(2H)-pyran-2-one; 29–3-methyl-furan-2,5-dione; 31–2-hydroxy-3-methyl-2-cyclopenten-1-one; 33–2-hydroxy-1-methyl-1-cyclopentene-3-one; 36 –sugar derivative; 39–5-hydroxymethyldihydrofuran-2-one; 42 –sugar derivative; 47 –sugar derivative; 51–2,3-dihydrobenzofuran; 52–4-vinylguaiacol; 54 –similar to 4-allylphenol; 59–2-hydroxymethyl-5-hydroxy-2,3-dihydro-(4H)-pyran-4-one; 60 –methylindole; 67–4-vinylsyringol; 68–4-allylsyringol; 72–1,6-anhydro-β-D-glucopyranose; 73 –trans-4-propenylsyringol; 75 –Not identified; 81 –trans-sinapaldehyde.

(A) Phenolic metabolites, belonging to the benzoate, tyrosine, and food component/plant pathways that are significantly different between ASD vs TD groups in plasma (P), and feces (F). Directionality and significance defined in legend, and numerical fold change in text within the box. (B) Scaled intensity values indicating relative levels of 4-allylphenol sulfate in plasma (all samples). (C) Scaled intensity values indicating relative levels of 2-ethylphenyl sulfate in plasma (all samples). (D) Scaled intensity values indicating relative levels of 4-ethylphenyl sulfate (4EPS) in plasma (all samples). (E) Spearman correlation between plasma 4EPS and 4-acetylphenol sulfate, log₂ scale. Data in (B-D) are represented as mean ± SEM. Asterisks indicate significance in ANOVA contrasts with an FDR cutoff q-value<0.1 performed on total metabolomics dataset (p-values: **<0.01, ****<0.0001).