Details
Stereochemistry | ABSOLUTE |
Molecular Formula | C50H83NO21 |
Molecular Weight | 1034.1881 |
Optical Activity | UNSPECIFIED |
Defined Stereocenters | 31 / 31 |
E/Z Centers | 0 |
Charge | 0 |
SHOW SMILES / InChI
SMILES
[H][C@]12C[C@@]3([H])[C@]4([H])CC[C@@]5([H])C[C@H](CC[C@]5(C)[C@@]4([H])CC[C@]3(C)[C@@]1([H])[C@H](C)[C@]6(CC[C@H](C)CN6)O2)O[C@]7([H])O[C@H](CO)[C@H](O[C@]8([H])O[C@H](CO)[C@@H](O)[C@H](O[C@]9([H])OC[C@@H](O)[C@H](O)[C@H]9O)[C@H]8O[C@]%10([H])O[C@H](CO)[C@@H](O)[C@H](O)[C@H]%10O)[C@H](O)[C@H]7O
InChI
InChIKey=REJLGAUYTKNVJM-SGXCCWNXSA-N
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
Alpha (α)-tomatine (simply tomatine) is the major saponin and occurs naturally in tomatoes, possesses a variety of biological properties including antioxidant, and anti-inflammatory. In additıon, tomatine is also known that it breaks down the cell membrane induces growth inhibition and apoptosis in different cancer cells: myeloid leukemia cells; prostate cancer cells; lung adenocarcinoma cells. However, the mechanisms of α-tomatine actions were not well understood. Nevertheless, was shown, that tomatine inhibited the NF-κB and phosphatidyl-inositol-3-kinase/Akt signaling pathways activation. However, the primary cellular target(s) for α-tomatine and its mechanisms for modulating apoptosis-associated pathways remain to be elucidated. The interaction of α-tomatine with cholesterol and the disruptive effect on the cell membrane may be one of the mechanisms by which α-tomatine induces apoptosis. The formation of complexes of α-tomatine and cholesterol may modulate the responsiveness of cell membrane receptors to growth stimuli and thus decrease the growth of cancer cells. Moreover, the anti-inflammatory mechanisms of α-tomatine, which may be a valuable therapeutic agent in the treatment of inflammation-related diseases was due to the ability of tomatine accelerated the phosphorylation of Akt in macrophages.
Approval Year
Targets
Primary Target | Pharmacology | Condition | Potency |
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Target ID: map04151 Sources: https://www.ncbi.nlm.nih.gov/pubmed/19457446 |
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Target ID: map04010 Sources: https://www.ncbi.nlm.nih.gov/pubmed/19457446 |
Conditions
Condition | Modality | Targets | Highest Phase | Product |
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Primary | Unknown Approved UseUnknown |
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Primary | Unknown Approved UseUnknown |
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Primary | Unknown Approved UseUnknown |
PubMed
Title | Date | PubMed |
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Potentiation by a novel alkaloid glycoside adjuvant of a protective cytotoxic T cell immune response specific for a preerythrocytic malaria vaccine candidate antigen. | 2001 Jul 20 |
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Common phytochemicals are ecdysteroid agonists and antagonists: a possible evolutionary link between vertebrate and invertebrate steroid hormones. | 2001 Jun |
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Tomato glycoalkaloids: role in the plant and in the diet. | 2002 Oct 9 |
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Determination of glycoalkaloids and relative aglycones by nonaqueous capillary electrophoresis coupled with electrospray ionization-ion trap mass spectrometry. | 2002 Sep |
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Purification, crystallization and preliminary X-ray diffraction analysis of a fungal saponin-detoxifying enzyme. | 2004 Jul |
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Tomatidine and lycotetraose, hydrolysis products of alpha-tomatine by Fusarium oxysporum tomatinase, suppress induced defense responses in tomato cells. | 2004 Jul 30 |
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The apoptotic and necrotic effects of tomatine adjuvant. | 2004 Jun 2 |
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Immunobiology of the Tomatine adjuvant. | 2004 Jun 23 |
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Tissue distribution of cholinesterases and anticholinesterases in native and transgenic tomato plants. | 2004 May |
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Influence of incorporated wild Solanum genomes on potato properties in terms of starch nanostructure and glycoalkaloid content. | 2005 Jun 29 |
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A liquid chromatography-mass spectrometry-based metabolome database for tomato. | 2006 Aug |
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Interaction of the glycoalkaloid tomatine with DMPC and sterol monolayers studied by surface pressure measurements and Brewster angle microscopy. | 2006 Nov 9 |
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Tomatinase from Fusarium oxysporum f. sp. lycopersici is required for full virulence on tomato plants. | 2008 Jun |
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Alpha-tomatine inactivates PI3K/Akt and ERK signaling pathways in human lung adenocarcinoma A549 cells: effect on metastasis. | 2009 Aug |
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Tomatine-containing green tomato extracts inhibit growth of human breast, colon, liver, and stomach cancer cells. | 2009 Jul 8 |
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Evidence for allosteric interactions of antagonist binding to the smoothened receptor. | 2009 Jun |
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Immunology and cell biology of parasitic diseases. | 2010 |
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Changes in free amino acid, phenolic, chlorophyll, carotenoid, and glycoalkaloid contents in tomatoes during 11 stages of growth and inhibition of cervical and lung human cancer cells by green tomato extracts. | 2010 Jul 14 |
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Mass spectrometry screening reveals widespread diversity in trichome specialized metabolites of tomato chromosomal substitution lines. | 2010 May |
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Naturally occurring food toxins. | 2010 Sep |
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In vivo antimalarial activities of glycoalkaloids isolated from Solanaceae plants. | 2010 Sep |
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The tomato odorless-2 mutant is defective in trichome-based production of diverse specialized metabolites and broad-spectrum resistance to insect herbivores. | 2010 Sep |
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Applications of femtochemistry to proteomic and metabolomic analysis. | 2010 Sep 30 |
Patents
Sample Use Guides
In Vivo Use Guide
Sources: https://www.ncbi.nlm.nih.gov/pubmed/26630272
Male severe combined immunodeficient (SCID) mice bearing PC-3 xenograft tumors were treated with i.p injections with vehicle (5 μl/g body weight), α-tomatine (5 mg/kg), curcumin (5 mg/kg), or α-tomatine (5 mg/kg) + curcumin (5 mg/kg) three times a week for 30 days.
Route of Administration:
Intraperitoneal
In Vitro Use Guide
Sources: https://www.ncbi.nlm.nih.gov/pubmed/28669925
There was evaluated the effect of tomatine on cytotoxicity, apoptosis and matrix metalloproteinase inhibition in MCF-7 cell lines. Human breast cancer cell line (MCF-7) was used as a cell line. In MCF-7 cells, the IC50 dose of tomatine was determined to be 7.07 μM. According to the control cells, apoptosis increased 3.4 fold in 48thh. Activation of MMP-2, MMP-9 and MMP-9\NGAL has been shown to decrease significantly in cells treated with tomatine by gelatin zymography compared to the control. As a result, matrix metalloproteinase activity and cell proliferation were suppressed by tomatine
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SUBSTANCE RECORD