Experimental determination of octanol-water partition coefficients of quercetin and related flavonoids

  • Rothwell J
  • Day A
  • Morgan M
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Abstract

Octanol-water partition coefficient (log P) values were determined for flavonoids from the flavone, flavonol, flavanone, and isoflavonoid subclasses. Each flavonoid was dissolved in an octanol-water system and allowed to equilibrate, and then both fractions were analyzed by high-performance liquid chromatography. log P was calculated as log[ratio of the concentration in the octanol phase to the concentration in the aqueous phase at pH 7.4]. The aglycons were more lipophilic than any conjugate. The conjugate moiety had a more significant effect on log P than the aglycon moiety. Quercetin was the least lipophilic aglycon (log P = 1.82 +/- 0.32) and, together with kaempferol (log P = 3.11 +/-0.54), gave the most variable results. The isoflavones genistein and daidzein and the isoflavone metabolite equol gave relatively high log P values (3.04 +/- 0.02, 2.51 +/- 0.06, and 3.20 +/- 0.13, respectively), while glycitein had an unexpectedly low value of 1.97 +/- 0.05. The conjugation characteristics and hydroxylation pattern were the most important determinants of log P in general, and log P was highly variable within the flavonoid subclass. The results are discussed in terms of further understanding of the in vivo fate of the flavonoids as important dietary bioactives.

Author-supplied keywords

  • Dietary nonnutrients
  • Flavonoids
  • Isoflavones
  • Log P
  • Partition coefficients
  • Phytochemicals
  • Quercetin

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Authors

  • Joseph A. Rothwell

  • Andrea J. Day

  • Michael R.A. Morgan

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