Tomatine

Not to be confused with Tomatin or thaumatin.

α-Tomatine
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
CAS Number	17406-45-0^N
ChEBI	CHEBI:9630^Y
ChEMBL	ChEMBL525778^Y
ChemSpider	26536^Y
Jmol interactive 3D	Image
PubChem	623058
InChI InChI=1S/C50H83NO21/c1-20-7-12-50(51-15-20)21(2)32-28(72-50)14-26-24-6-5-22-13-23(8-10-48(22,3)25(24)9-11-49(26,32)4)65-45-40(63)37(60)41(31(18-54)68-45)69-47-43(71-46-39(62)36(59)34(57)29(16-52)66-46)42(35(58)30(17-53)67-47)70-44-38(61)33(56)27(55)19-64-44/h20-47,51-63H,5-19H2,1-4H3/t20-,21-,22-,23-,24+,25-,26-,27+,28-,29+,30+,31+,32-,33-,34+,35+,36-,37+,38+,39+,40+,41-,42-,43+,44-,45+,46-,47-,48-,49-,50-/m0/s1^Y Key: REJLGAUYTKNVJM-SGXCCWNXSA-N^Y
SMILES [H][C@@]12CC[C@]3([H])[C@]([H])(CC[C@@]4(C)[C@@]3([H])C[C@]3([H])O[C@@]5(CC[C@H](C)CN5)[C@@H](C)[C@]43[H])[C@@]1(C)CC[C@@H](C2)O[C@@H]1O[C@H](CO)[C@H](O[C@@H]2O[C@H](CO)[C@@H](O)[C@H](O[C@@H]3OC[C@@H](O)[C@H](O)[C@H]3O)[C@H]2O[C@@H]2O[C@H](CO)[C@@H](O)[C@H](O)[C@H]2O)[C@H](O)[C@H]1O
Properties
Chemical formula	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 is ^YN ?)
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

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

1 2 "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
↑ tomatine (CHEBI:9630)
↑ 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.
↑ 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.
↑ 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.
↑ Cayen, M. N. (1971). "Effect of dietary tomatine on cholesterol metabolism in the rat". Journal of Lipid Research 12 (4): 482–90. PMID 4362143.
↑ 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.

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