D-Fructose-L-histidine

Last updated
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
3D model (JSmol)
ChemSpider
PubChem CID
  • pyranose:InChI=1S/C12H19N3O7/c16-8-3-22-12(21,10(18)9(8)17)4-14-7(11(19)20)1-6-2-13-5-15-6/h2,5,7-10,14,16-18,21H,1,3-4H2,(H,13,15)(H,19,20)/t7-,8+,9-,10?,12?/m0/s1
    Key: DTFFYNMHSHLNDP-NAORZKMKSA-N
  • InChI=1S/C12H19N3O7/c13-7(1-6-2-14-5-15-6)12(21)22-4-9(18)11(20)10(19)8(17)3-16/h2,5,7-8,10-11,16-17,19-20H,1,3-4,13H2,(H,14,15)/t7-,8+,10+,11+/m0/s1
    Key: CJYXLKPEYVVNDY-SCVMZPAESA-N
  • pyranose:O=C(O)[C@H](Cc1cnc[nH]1)NCC1(O)OC[C@@H](O)[C@H](O)C1O
  • C1=C(NC=N1)C[C@@H](C(=O)OCC(=O)[C@H]([C@@H]([C@@H](CO)O)O)O)N
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).

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

  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. PMID   18004802.
  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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