Tomatine

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Not to be confused with Tomatin or thaumatin.
α-Tomatine
Alpha-Tomatine.png
Names
IUPAC name
(22S,25S)-5α-spirosolan-3β-yl β-D-glucopyranosyl-(1→2)-[β-D-xylopyranosyl-(1→3)]-β-D-glucopyranosyl-(1→4)-β-D-galactopyranoside
Other names
Tomatine, Tomatin, Lycopersicin
Identifiers
17406-45-0 N
ChEBI CHEBI:9630 YesY
ChEMBL ChEMBL525778 YesY
ChemSpider 26536 YesY
Jmol-3D images Image
PubChem 623058
Properties
C50H83NO21
Molar mass 1034.18816
Appearance crystalline solid
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
 N verify (what isYesY/N?)
Infobox references

Tomatine is a glycoalkaloid found in the stems and leaves of tomato plants, which has fungicidal properties.[1] Chemically pure tomatine is a white crystalline solid at standard temperature and pressure.[2][3] Tomatine as well as the a-glycone derivative Tomatidine have been shown to have multiple health benefits.[4] Tomatine has antimicrobial properties against certain classes of microbes although some microbes produce an enzyme called tomatinase which can degrade tomatine, rendering it ineffective as an antimicrobial.[5]

Uses[edit]

Tomatine has been used as a reagent in analytical chemistry for precipitating cholesterol from solution.[1][6] Also, tomatine is known to be an immune adjuvant in connection with certain protein antigens.[7]

References[edit]

  1. ^ a b "tomatine." McGraw-Hill Dictionary of Scientific and Technical Terms. McGraw-Hill Companies, Inc., 2003. Answers.com 28 Mar. 2010. http://www.answers.com/topic/tomatine
  2. ^ tomatine (CHEBI:9630)
  3. ^ Degtyarenko, K.; De Matos, P.; Ennis, M.; Hastings, J.; Zbinden, M.; McNaught, A.; Alcantara, R.; Darsow, M.; Guedj, M.; Ashburner, M. (2007). "ChEBI: A database and ontology for chemical entities of biological interest". Nucleic Acids Research 36 (Database issue): D344–50. doi:10.1093/nar/gkm791. PMC 2238832. PMID 17932057. 
  4. ^ Friedman, Mendel (2013). "Anticarcinogenic, Cardioprotective, and Other Health Benefits of Tomato Compounds Lycopene, α-Tomatine, and Tomatidine in Pure Form and in Fresh and Processed Tomatoes". Journal of Agricultural and Food Chemistry 61 (40): 9534–50. doi:10.1021/jf402654e. PMID 24079774. 
  5. ^ Seipke, Ryan F.; Loria, Rosemary (2008). "Streptomyces scabies 87-22 Possesses a Functional Tomatinase". Journal of Bacteriology 190 (23): 7684–92. doi:10.1128/JB.01010-08. PMC 2583622. PMID 18835993. 
  6. ^ Cayen, M. N. (1971). "Effect of dietary tomatine on cholesterol metabolism in the rat". Journal of Lipid Research 12 (4): 482–90. PMID 4362143. 
  7. ^ Heal, K. G.; Taylor-Robinson, A. W. (2010). "Tomatine Adjuvantation of Protective Immunity to a Major Pre-erythrocytic Vaccine Candidate of Malaria is Mediated via CD8+ T Cell Release of IFN-γ". Journal of Biomedicine and Biotechnology 2010: 834326. doi:10.1155/2010/834326. PMC 2837906. PMID 20300588.