Tomatine

Names

[ Name ]:
Tomatine

[Synonym ]:
Lycopersicin
(3β,5α,25S)-Spirosolan-3-yl-β-D-glucopyranosyl-(1->2)-[β-D-xylopyranosyl-(1->3)]-β-D-glucopyranosyl-(1->4)-β-D-galactopyranoside
EINECS 241-429-5
TOMATINE
(2S,3R,4S,5S,6R)-2-{[(2S,3R,4S,5R,6R)-2-{[(2R,3R,4R,5R,6R)-4,5-Dihydroxy-2-(hydroxyméthyl)-6-{[(2S,4aS,4bS,5'S,6aS,6bR,7S,8S,9aS,10aS,10bR,12aS)-4a,5',6a,7-tétraméthyloctadécahydrospiro[naphto[2',1':4,5]indéno[2,1-b]furane-8,2'-pipéridin]-2-yl]oxy}tétrahydro-2H-pyran-3-yl]oxy}-5-hydroxy-6-(hydroxyméthyl)-4-{[(2S,3R,4S,5R)-3,4,5-trihydroxytétrahydro-2H-pyran-2-yl]oxy}tétrahydro-2H-pyran-3-yl]oxy}-6-(hydroxyméthyl)tétrahydro-2H-pyran-3,4,5-triol
β-D-Galactopyranoside, (3β,5α,25S)-spirosolan-3-yl O-β-D-glucopyranosyl-(1->2)-O-[β-D-xylopyranosyl-(1->3)]-O-β-D-glucopyranosyl-(1->4)-
Tomatin
(3β,5α,25S)-Spirosolan-3-yl β-D-glucopyranosyl-(1->2)-[β-D-xylopyranosyl-(1->3)]-β-D-glucopyranosyl-(1->4)-β-D-galactopyranoside
(2S,3R,4S,5S,6R)-2-{[(2S,3R,4S,5R,6R)-2-{[(2R,3R,4R,5R,6R)-4,5-Dihydroxy-2-(hydroxymethyl)-6-{[(2S,4aS,4bS,5'S,6aS,6bR,7S,8S,9aS,10aS,10bR,12aS)-4a,5',6a,7-tetramethyloctadecahydrospiro[naphtho[2',1':4,5]indeno[2,1-b]furan-8,2'-piperidin]-2-yl]oxy}tetrahydro-2H-pyran-3-yl]oxy}-5-hydroxy-6-(hydroxymethyl)-4-{[(2S,3R,4S,5R)-3,4,5-trihydroxytetrahydro-2H-pyran-2-yl]oxy}tetrahydro-2H-pyran-3-yl]oxy}-6-(hydroxymethyl)tetrahydro-2H-pyran-3,4,5-triol

Biological Activity

[Description]:

Tomatine is a glycoalkaloid, found in the tomato plant (Lycopersicon esculentum Mill.). Tomatine elicits neurotoxicity in RIP1 kinase and caspase-independent manner. Tomatine promotes the upregulation of nuclear apoptosis inducing factor (AIF) in neuroblastoma cells. Tomatine also inhibits 20S proteasome activity[1].

[Related Catalog]:

Signaling Pathways >> Metabolic Enzyme/Protease >> Proteasome

Research Areas >> Neurological Disease

[In Vitro]

Tomatine inhibits gastric carcinoma cell line (AGS), neuroblastoma cell line (SH-SY5Y) and non-small cell lung cancer cell line (A549) with IC50s of 2 µM, 1.6 µM and 1.1 µM, respectively[1].

[References]

[1]. da Silva DC, et al. Neurotoxicity of the steroidal alkaloids tomatine and tomatidine is RIP1 kinase- and caspase-independent and involves the eIF2α branch of the endoplasmic reticulum. J Steroid Biochem Mol Biol. 2017 Jul;171:178-186.

Chemical & Physical Properties

[ Density]:
1.5±0.1 g/cm3

[ Melting Point ]:
300-305ºC

[ Molecular Formula ]:
C₅₀H₈₃NO₂₁

[ Molecular Weight ]:
1034.19

[ Exact Mass ]:
1033.545776

[ PSA ]:
337.86000

[ LogP ]:
2.22

[ Index of Refraction ]:
1.638

MSDS

Click to get detail MSDS

Toxicological Information

CHEMICAL IDENTIFICATION

RTECS NUMBER :: XW1050000

CHEMICAL NAME :: Tomatine

CAS REGISTRY NUMBER :: 17406-45-0

BEILSTEIN REFERENCE NO. :: 0078250

LAST UPDATED :: 199612

DATA ITEMS CITED :: 5

MOLECULAR FORMULA :: C50-H83-N-O21

MOLECULAR WEIGHT :: 1034.34

HEALTH HAZARD DATA

ACUTE TOXICITY DATA

TYPE OF TEST :: LD50 - Lethal dose, 50 percent kill

ROUTE OF EXPOSURE :: Oral

SPECIES OBSERVED :: Rodent - mouse

DOSE/DURATION :: 500 mg/kg

TOXIC EFFECTS :: Details of toxic effects not reported other than lethal dose value

TYPE OF TEST :: LD50 - Lethal dose, 50 percent kill

ROUTE OF EXPOSURE :: Intraperitoneal

SPECIES OBSERVED :: Rodent - mouse

DOSE/DURATION :: 25 mg/kg

TOXIC EFFECTS :: Details of toxic effects not reported other than lethal dose value

TYPE OF TEST :: LD50 - Lethal dose, 50 percent kill

ROUTE OF EXPOSURE :: Subcutaneous

SPECIES OBSERVED :: Rodent - mouse

DOSE/DURATION :: 1 gm/kg

TOXIC EFFECTS :: Details of toxic effects not reported other than lethal dose value

MUTATION DATA

TYPE OF TEST :: Mutation test systems - not otherwise specified

TEST SYSTEM :: Microorganism - not otherwise specified

DOSE/DURATION :: 25 ppm

REFERENCE :: FCTXAV Food and Cosmetics Toxicology. (London, UK) V.1-19, 1963-81. For publisher information, see FCTOD7. Volume(issue)/page/year: 17,61,1979

Safety Information

[ Hazard Codes ]:
Xn: Harmful;

[ Risk Phrases ]:
R23/25

[ Safety Phrases ]:
45-24/25-22

[ RIDADR ]:
UN 1544

[ RTECS ]:
XW1050000

[ HS Code ]:
29329990