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Quantification of javamide‐I and ‐II in twelve coffee drinks and their effects on sirtuin1/2/3 enzymes and p53‐acetylation in THP‐1 cells.
Author(s) -
Park Jae
Publication year - 2016
Publication title -
the faseb journal
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 1.709
H-Index - 277
eISSN - 1530-6860
pISSN - 0892-6638
DOI - 10.1096/fasebj.30.1_supplement.145.2
Subject(s) - chemistry , acetylation , in vitro , enzyme , food science , ic50 , biochemistry , gene
Coffee is one of most consumed drinks worldwide. Javamide‐I ( N ‐coumaroyltryptophan) and‐ II ( N ‐caffeoyltryptophan) are phenolic amides found in coffee. However, the amounts of javamide‐I and‐ II have not been determined in daily consumed coffee drinks, and their effects on sirtuin1/2/3 enzymes are still unknown. Therefore, in this paper, javamide‐I and ‐II were isolated and quantified from coffee using a HPLC method, and their effects on sirtuin1/2/3 enzymes were studied. First, the chemical structures of isolated javamide‐I and‐ II were unambiguously confirmed using NMR spectroscopic methods. Then, their amounts were determined in 12 different coffee samples prepared using five beans, four ground and three instant coffees. Javamide‐I and ‐II were detected in some coffee samples at the ranges of 0.04–2.31 mg/g. Using javamide‐I and ‐II isolated from coffee, their effects on sirtuin1 (nuclear), sirtuin2 (cytoplasm) and sirtuin3 (mitochondria) were investigated in vitro . Javamide‐II showed higher inhibition activity against sirtuin1 (IC 50 of 30 μM), 2 (IC 50 of 8 μM) and 3(IC 50 of 61 μM) than javamide‐I. Especially related to sirtuin2, javamide‐II exhibited noncompetitive inhibition of sirtuin2 with K i = 9.6 μM. In a docking simulation, javamide‐II showed stronger binding pose to sirtuin2 than EX527. Also, javamide‐II was able to increase total acetylation levels and the acetylation of p53 in monocytic THP‐1 cells. In addition, differential effects of javamide‐I and ‐II analogues on inhibiting sirtuin1/2/3 will be also discussed in this study. Support or Funding Information USDA