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This study was performed to isolate and identify a compound with antiproliferative activity against human stomach cancer cell lines, from fructose-tryptophan Maillard reaction products (MRPs). The MRPs, prepared from a fructose-tryptophan solution heated at 130 °C for 2 h, were fractionated into five solvent fractions: n-hexane, chloroform, ethyl acetate, butanol, and water. The highest antiproliferative activity was found in the chloroform fraction (85.93% at 200 μg/mL), and the active compound from this chloroform fraction was purified by silica gel column chromatography, TLC, and preparative HPLC. The antiproliferative activity (IC50) of the active compound was 42.24 μg/mL, and the active compound was identified as perlolyrine (C16H10N2O2) by (1)H/(13)C NMR, DEPT, HMBC, and LC-ESI-MS. Therefore, this research may be useful in developing perlolyrine as a functional therapeutic agent.

Abstract: We isolated a substance from fructose–tyrosine Maillard reaction products (MRPs) and investigated its antiproliferative effect on six human cancer cell lines. The ethyl acetate fraction of fructose–tyrosine MRPs showed a strong antiproliferative effect; this fraction was isolated and purified using silica gel column chromatography, semipreparative RP-HPLC, and recycling HPLC. The structure of the purified compound was determined using spectroscopic methods. The isolated compound was identified as 2,4-bis(p-hydroxyphenyl)-2-butenal (C16H14O3, HPB242). HPB242 inhibited cell growth in a dose-dependent manner (10–80μg/ml) on the six human cancer cell lines. The IC50 values of HPB242 on the six human cancer cell lines were 17.34μg/ml (MCF-7), 29.21μg/ml (HCT-116), 34.57μg/ml (H-460), 34.87μg/ml (HepG2), 48.77μg/ml (PC-3), and 55.83μg/ml (MKN-45). [Copyright &y& Elsevier]

Abstract: An α-glucosidase inhibitory substance was isolated and characterised from fructose–tyrosine Maillard reaction products (MRPs) and the inhibition mode of the active substance determined. The ethyl acetate fraction of fructose–tyrosine MRPs showed strong α-glucosidase inhibitory activity; this fraction was isolated and purified using silica gel column chromatography and semi-preparative RP-HPLC. The structure of the purified compound was determined using spectroscopic methods. The isolated compound was identified as 2,4-bis (p-hydroxyphenyl)-2-butenal (C16H14O3, HPB242). This is the first report of baker’s yeast α-glucosidase inhibitory activity of HPB242 isolated from fructose–tyrosine MRPs. The IC50 value of HPB242 on α-glucosidase inhibition was 4.00±0.09μg/ml. Kinetic data revealed that HPB242 inhibits the p-NPG hydrolysing activity of baker’s yeast α-glucosidase noncompetitively with a K i value of 0.870mM. [Copyright &y& Elsevier]

Abstract: The various biological activities of Maillard reaction products (MRPs) from sugar (fructose and glucose) and 20 amino acid model systems were evaluated. Colour development, in vitro antioxidant, α-glucosidase inhibitory, antihypertensive, and antiproliferative activities of aqueous solutions of MRPs produced by heating at 130°C for 2h were measured. The fructose–amino acid mixture showed higher UV-absorbance and browning intensity than the glucose–amino acid mixture. The fructose–amino acid model MRPs showed higher DPPH and ABTS radical scavenging and ACE inhibitory activities than the glucose–amino acid model MRPs. The α-glucosidase inhibitory effect of MRPs derived from fructose– and glucose–tyrosine showed higher α-glucosidase inhibitory activity than that of other MRPs. Sugar–amino acid model MRPs inhibited the growth of HCT116 colon cancer cell in a dose-dependent manner (from 0.5 to 1.5mg/ml). Glucose MRPs showed slightly higher antiproliferative activity than fructose MRPs. In particular, sugar–tryptophan and –tyrosine MRPs exerted higher biological activities than the other MRPs. [ABSTRACT FROM AUTHOR]