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D-Fructose-L-histidine

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d-Fructose-l-histidine
Names
IUPAC name (2S)-3-(1H-Imidazol-5-yl)-2-({methyl}amino)propanoate
Other names N-(1-Deoxy-d-fructos-1-yl)-l-histidine; Fructose-histidine; FruHis
Identifiers
CAS Number
ChemSpider
PubChem CID
Properties
Chemical formula C12H19N3O7
Molar mass 317.298 g·mol
Except where otherwise noted, data are given for materials in their standard state (at 25 °C , 100 kPa). Infobox references
Chemical compound

d-Fructose-l-histidine (FruHis) is a ketosamine combining the d-isomer of fructose and the l-isomer of histidine into a functional group. FruHis is present in dried fruits. In interaction with lycopene, FruHis is a potential food related antioxidant and chemopreventive agent, found abundantly in dried tomatoes.

Research

A group of carbohydrate derivatives present in dehydrated tomato products interact with lycopene against prostate cancer. FruHis strongly synergizes with lycopene against the proliferation of highly metastatic rat prostate cancer cell lines in vitro. The FruHis/lycopene combination significantly inhibits in vivo tumorigenesis in syngeneic rats. The ketosamine completely blocks DNA oxidative degradation at >250 μmol/L in vitro, whereas neither ascorbate nor phenolic antioxidants from tomato are effective protectors.

Based on these studies, the American Association for Cancer Research has concluded that FruHis may exert tumor-preventive effect through its antioxidant activity and interaction with lycopene.

References

  1. Valeri V. Mossine and Thomas P. Mawhinney (2007). "N-(1-Deoxy-D-fructos-1-yl)-L-histidine ("D-Fructose-L-histidine"): a Potent Copper Chelator from Tomato Powder". J. Agric. Food Chem. 55 (25): 10373–10381. doi:10.1021/jf072092i.
  2. Mossine, V. V.; Chopra, P.; Mawhinney, T. P. (2008). "Interaction of Tomato Lycopene and Ketosamine against Rat Prostate Tumorigenesis". Cancer Research. 68 (11): 4384–91. doi:10.1158/0008-5472.CAN-08-0108. PMID 18519700.
  3. Pannellini, T.; Iezzi, M.; Liberatore, M.; Sabatini, F.; Iacobelli, S.; Rossi, C.; Alberti, S.; Di Ilio, C.; Vitaglione, P. (2010). "A Dietary Tomato Supplement Prevents Prostate Cancer in TRAMP Mice". Cancer Prevention Research. 3 (10): 1284–91. doi:10.1158/1940-6207.CAPR-09-0237. PMID 20716635.
  4. "Dehydrated Tomatoes Show Promise For Preventing Prostate Cancer". ScienceDaily. 2 June 2008.
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