Chemistry:D-Fructose-L-histidine
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| 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). | |
| Infobox references | |
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
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
- ↑ 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.
- ↑ 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.
- ↑ 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.
- ↑ "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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