Names | |
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IUPAC name
(2S)-3-(1H-Imidazol-5-yl)-2-({[(3S,4S,5R)-2,3,4-trihydroxy-5-(hydroxymethyl)oxolan-2-yl]methyl}amino)propanoate
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Other names
Nα-(1-Deoxy-d-fructos-1-yl)-l-histidine; Fructose-histidine; FruHis
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Identifiers | |
ChemSpider | |
PubChem
CID
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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).
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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]
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]