Chemistry:D-Fructose-L-histidine

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d-Fructose-l-histidine
D-Fructose-L-histidine.svg
Names
IUPAC name
(2S)-3-(1H-Imidazol-5-yl)-2-({[(3S,4S,5R)-2,3,4-trihydroxy-5-(hydroxymethyl)oxolan-2-yl]methyl}amino)propanoate
Other names
Nα-(1-Deoxy-d-fructos-1-yl)-l-histidine; Fructose-histidine; FruHis
Identifiers
ChemSpider
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Properties
C12H19N3O7
Molar mass 317.298 g·mol−1
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
Infobox references
Tracking categories (test):

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.[1]

Research[edit]

A group of carbohydrate derivatives present in dehydrated tomato products interact with lycopene against prostate cancer.[2][3] 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.[4]

References[edit]

  1. Valeri V. Mossine and Thomas P. Mawhinney (2007). "Nα-(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. et al. (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. https://www.sciencedaily.com/releases/2008/05/080529091118.htm. 

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