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Tomatine

Tomatine structure

Tomatine 

structure
  • CAS No:

    17406-45-0

  • Formula:

    C50H83NO21

  • Chemical Name:

    Tomatine

  • Synonyms:

    β-D-Galactopyranoside,(3β,5α,22β,25S)-spirosolan-3-yl O-β-D-glucopyranosyl-(1→2)-O-[β-D-xylopyranosyl-(1→3)]-O-β-D-glucopyranosyl-(1→4)-;Tomatine;α-Tomatine;Spiro[8H-naphth[2′,1′:4,5]indeno[2,1-b]furan-8,2′-piperidine],β-D-galactopyranoside deriv.;Spirosolane,β-D-galactopyranoside deriv.;(3β,5α,22β,25S)-Spirosolan-3-yl O-β-D-glucopyranosyl-(1→2)-O-[β-D-xylopyranosyl-(1→3)]-O-β-D-glucopyranosyl-(1→4)-β-D-galactopyranoside;Lycopersicin;NSC 234440;NSC 9223;1389-21-5;7090-83-7;17406-24-5;21283-97-6

  • Categories:

    Natural Products  >  Alkaloids

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].


Solid


An alkaloid that occurs in the extract of leaves of wild tomato plants. It has been found to inhibit the growth of various fungi and bacteria. It is used as a precipitating agent for steroids. (From The Merck Index, 11th ed)

Tomatine Basic Attributes

1034.19

1034.19

241-429-5

234440|9223

DTXSID5040413

NEEDLES FROM METHANOL|WHITE CRYSTALS

29329990

Characteristics

337.86000

2.22

white to light yellow

1.5±0.1 g/cm3

263-268 °C

1.638

SOLUBLE IN ETHANOL, METHANOL, DIOXANE, PROPYLENE GLYCOL; PRACTICALLY INSOLUBLE IN WATER, ETHER, PETROLEUM ETHER

2-8°C

D20 -18° (c = 0.55 in pyridine)

Safety Information

1544

23/25-22

45-24/25-22

XW1050000

Xn

H302

|Warning|H302 (100%): Harmful if swallowed [Warning Acute toxicity, oral]|P264, P270, P301+P312, P330, and P501|Aggregated GHS information provided by 4 companies from 1 notifications to the ECHA C&L Inventory.

Toxicity

TOMATINE REDUCED THE GROWTH ENHANCED BY 10-4 MOLAR INDOLE-3-ACETIC ACID.

OCCURS IN THE EXTRACT OF LEAVES OF WILD TOMATO PLANTS.

Drug Information

Antifungal Agents; Anti-Infective Agents; Indicators and Reagents|EXPTL USE: TOMATINE GIVEN TO INTACT RATS AT 1-10 MG/KG IM OR 15-30 MG/KG ORALLY PRODUCED A DOSE-DEPENDENT INHIBITION OF CARRAGEENAN-INDUCED PAW EDEMA. THE EFFECT OF THE IM 10 MG/KG DOSE LASTED 24 HOURS. TOMATINE AT 5-10 MG/KG GIVEN DAILY TO INTACT RATS FOR 7 DAYS PRODUCED A DOSE-DEPENDENT INHIBITION OF GRANULATION TISSUE FORMATION INDUCED BY SC IMPLANTATION OF CARRAGEENAN-IMPREGNATED COTTON PELLETS.

Substances that prevent infectious agents or organisms from spreading or kill infectious agents in order to prevent the spread of infection. (See all compounds classified as Anti-Infective Agents.)|Substances used for the detection, identification, analysis, etc. of chemical, biological, or pathologic processes or conditions. Indicators are substances that change in physical appearance, e.g., color, at or approaching the endpoint of a chemical titration, e.g., on the passage between acidity and alkalinity. Reagents are substances used for the detection or determination of another substance by chemical or microscopical means, especially analysis. Types of reagents are precipitants, solvents, oxidizers, reducers, fluxes, and colorimetric reagents. (From Grant and Hackh's Chemical Dictionary, 5th ed, p301, p499) (See all compounds classified as Indicators and Reagents.)|Substances that destroy fungi by suppressing their ability to grow or reproduce. They differ from FUNGICIDES, INDUSTRIAL because they defend against fungi present in human or animal tissues. (See all compounds classified as Antifungal Agents.)

SIX GLYCOALKALOIDS AND ONE AGLYCONE WERE TESTED FOR CARDIOTONIC ACTIVITIES AND COMPARED WITH K-STROPHANTHOSIDE BY USE OF THE ISOLATED FROG HEART. THE DECREASING ORDER OF POTENCY WAS AS FOLLOWS: K-STROPHANTHOSIDE GREATER THAN TOMATINE GREATER THAN ALPHA-CHACONINE EQUAL TO ALPHA-SOLANINE GREATER THAN DEMISSINE EQUAL TO COMMERSONINE GREATER THAN BETA-CHACONINE GREATER THAN SOLANIDINE. CARDIOTONIC ACTIVITY WAS DIRECTLY RELATED TO THE NUMBER OF SUGARS IN THE MOLECULE IN WHICH THE GLYCOALKALOIDS HAD A COMMON AGLYCONE.|REMOVAL OF 1 OR MORE SUGAR RESIDUES FROM THE ALPHA-TOMATINE MOLECULE MARKEDLY DECREASED ITS FUNGITOXICITY. ALTHOUGH THE PARTIAL HYDROLYSIS OF ALPHA-TOMATINE DID NOT GREATLY AFFECT ITS SURFACTANT PROPERTIES, IT DID DESTROY THE ABILITY OF THE ALKALOID TO FORM A COMPLEX WITH CHOLESTEROL.

Tomatine

Tomatine Use and Manufacturing

Methods of Manufacturing

A GLYCOSIDAL ALKALOID PREPARED FROM THE DRIED LEAVES AND STEMS OF THE TOMATO PLANT. ... THE CRUDE EXTRACT IS REFERRED TO AS TOMATIN.

Uses

Precipitating agent for steroids.

HAS BEEN FOUND TO INHIBIT THE GROWTH OF VARIOUS FUNGI AND BACTERIA.|YIELDS ON PARTIAL HYDROLYSIS, BESIDES ALPHA-TOMATINE, THE MAIN CONSTITUENT, BETA1-, BETA2-, GAMMA-, AND DELTA-TOMATINE... ALPHA-TOMATINE CONSISTS OF ONE MOL TOMATIDINE LINKED TO A TETRASACCHARIDE COMPOSED OF 2 MOLS D-GLUCOSE, 1 MOL D-XYLOSE AND 1 MOL D-GALACTOSE...|STABLE TO STRONG ALKALI BUT HYDROLYZED BY ACIDS TO PRODUCE CRYSTALLINE TOMATIDINE AND A SOLUTION RICH IN REDUCING SUGARS.

Computed Properties

Molecular Weight:1034.2
XLogP3:-0.7
Hydrogen Bond Donor Count:13
Hydrogen Bond Acceptor Count:22
Rotatable Bond Count:11
Exact Mass:1033.54575866
Monoisotopic Mass:1033.54575866
Topological Polar Surface Area:338
Heavy Atom Count:72
Complexity:1840
Undefined Atom Stereocenter Count:31
Covalently-Bonded Unit Count:1
Compound Is Canonicalized:Yes

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