Tomatine
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MedKoo CAT#: 571049

CAS#: 17406-45-0

Description: Tomatine is an glycoalkaloid 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. Treatment of human myeloid leukemia HL‑60 cells with tomatine has been shown to result in growth inhibition and apoptosis in a concentration‑dependent manner.

Chemical Structure

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Tomatine
CAS# 17406-45-0
Instruction

Theoretical Analysis

MedKoo Cat#: 571049
Name: Tomatine
CAS#: 17406-45-0
Chemical Formula: C50H83NO21
Exact Mass: 1,033.55
Molecular Weight: 1,034.200
Elemental Analysis: C, 58.07; H, 8.09; N, 1.35; O, 32.49

Price and Availability

Size Price Availability Quantity
5mg USD 350 2 Weeks
10mg USD 650 2 Weeks
25mg USD 1050 2 Weeks
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Synonym: Tomatine; Lycopersicin; NSC 234440; NSC 9223; α-Tomatine

IUPAC/Chemical Name: (2S,3R,4S,5S,6R)-2-(((2S,3R,4S,5R,6R)-2-(((2R,3R,4R,5R,6R)-4,5-dihydroxy-2-(hydroxymethyl)-6-(((2aS,4S,5'S,6aS,6bS,8aS,8bR,9S,10S,11aS,12aS,12bR)-5',6a,8a,9-tetramethyloctadecahydrospiro[naphtho[2',1':4,5]indeno[2,1-b]furan-10,2'-piperidin]-4-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

InChi Key: REJLGAUYTKNVJM-SGXCCWNXSA-N

InChi Code: 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

SMILES Code: C[C@H]1CC[C@]2([C@H]([C@H]3[C@@H](O2)C[C@@H]4[C@@]3(CC[C@H]5[C@H]4CC[C@@H]6[C@@]5(CC[C@@H](C6)O[C@H]7[C@@H]([C@H]([C@H]([C@H](O7)CO)O[C@H]8[C@@H]([C@H]([C@@H]([C@H](O8)CO)O)O[C@H]9[C@@H]([C@H]([C@@H](CO9)O)O)O)O[C@H]2[C@@H]([C@H]([C@@H]([C@H](O2)CO)O)O)O)O)O)C)C)C)NC1

Appearance: Solid powder

Purity: >98% (or refer to the Certificate of Analysis)

Shipping Condition: Shipped under ambient temperature as non-hazardous chemical. This product is stable enough for a few weeks during ordinary shipping and time spent in Customs.

Storage Condition: Dry, dark and at 0 - 4 C for short term (days to weeks) or -20 C for long term (months to years).

Solubility: Soluble in DMSO

Shelf Life: >2 years if stored properly

Drug Formulation: This drug may be formulated in DMSO

Stock Solution Storage: 0 - 4 C for short term (days to weeks), or -20 C for long term (months).

HS Tariff Code: 2934.99.9001

More Info:

Biological target:
In vitro activity:
In vivo activity:

Preparing Stock Solutions

The following data is based on the product molecular weight 1,034.20 Batch specific molecular weights may vary from batch to batch due to the degree of hydration, which will affect the solvent volumes required to prepare stock solutions.

Recalculate based on batch purity %
Concentration / Solvent Volume / Mass 1 mg 5 mg 10 mg
1 mM 1.15 mL 5.76 mL 11.51 mL
5 mM 0.23 mL 1.15 mL 2.3 mL
10 mM 0.12 mL 0.58 mL 1.15 mL
50 mM 0.02 mL 0.12 mL 0.23 mL
Formulation protocol:
In vitro protocol:
In vivo protocol:

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1: Huang H, Chen S, Van Doren J, Li D, Farichon C, He Y, Zhang Q, Zhang K, Conney AH, Goodin S, Du Z, Zheng X. α-Tomatine inhibits growth and induces apoptosis in HL-60 human myeloid leukemia cells. Mol Med Rep. 2015 Jun;11(6):4573-8. doi: 10.3892/mmr.2015.3238. Epub 2015 Jan 22. PubMed PMID: 25625536; PubMed Central PMCID: PMC4735690.

2: Zhao B, Zhou B, Bao L, Yang Y, Guo K. Alpha-Tomatine Exhibits Anti-inflammatory Activity in Lipopolysaccharide-Activated Macrophages. Inflammation. 2015 Oct;38(5):1769-76. doi: 10.1007/s10753-015-0154-9. PubMed PMID: 25772114.

3: Ökmen B, Etalo DW, Joosten MH, Bouwmeester HJ, de Vos RC, Collemare J, de Wit PJ. Detoxification of α-tomatine by Cladosporium fulvum is required for full virulence on tomato. New Phytol. 2013 Jun;198(4):1203-14. doi: 10.1111/nph.12208. Epub 2013 Mar 1. PubMed PMID: 23448507.

4: Huang H, Chen X, Li D, He Y, Li Y, Du Z, Zhang K, DiPaola R, Goodin S, Zheng X. Combination of α-Tomatine and Curcumin Inhibits Growth and Induces Apoptosis in Human Prostate Cancer Cells. PLoS One. 2015 Dec 2;10(12):e0144293. doi: 10.1371/journal.pone.0144293. eCollection 2015. PubMed PMID: 26630272; PubMed Central PMCID: PMC4668011.

5: Tomsik P, Micuda S, Sucha L, Cermakova E, Suba P, Zivny P, Mazurova Y, Knizek J, Niang M, Rezacova M. The anticancer activity of alpha-tomatine against mammary adenocarcinoma in mice. Biomed Pap Med Fac Univ Palacky Olomouc Czech Repub. 2013 Jun;157(2):153-61. doi: 10.5507/bp.2013.031. Epub 2013 May 3. PubMed PMID: 23681309.

6: Koh E, Kaffka S, Mitchell AE. A long-term comparison of the influence of organic and conventional crop management practices on the content of the glycoalkaloid α-tomatine in tomatoes. J Sci Food Agric. 2013 May;93(7):1537-42. doi: 10.1002/jsfa.5951. Epub 2012 Nov 9. PubMed PMID: 23138335.

7: Huang SL, He HB, Zou K, Bai CH, Xue YH, Wang JZ, Chen JF. Protective effect of tomatine against hydrogen peroxide-induced neurotoxicity in neuroblastoma (SH-SY5Y) cells. J Pharm Pharmacol. 2014 Jun;66(6):844-54. doi: 10.1111/jphp.12205. Epub 2014 Jan 7. PubMed PMID: 24392651.

8: Hsu PY, Wu CA, Shen SS, Yang YW. The role of tomatine adjuvant in antigen delivery for cross- presentation. Curr Drug Deliv. 2015;12(3):342-50. PubMed PMID: 26054535.

9: Sucha L, Hroch M, Rezacova M, Rudolf E, Havelek R, Sispera L, Cmielova J, Kohlerova R, Bezrouk A, Tomsik P. The cytotoxic effect of α-tomatine in MCF-7 human adenocarcinoma breast cancer cells depends on its interaction with cholesterol in incubation media and does not involve apoptosis induction. Oncol Rep. 2013 Dec;30(6):2593-602. doi: 10.3892/or.2013.2778. Epub 2013 Oct 2. PubMed PMID: 24100733; PubMed Central PMCID: PMC3839989.

10: Lee ST, Wong PF, He H, Hooper JD, Mustafa MR. Alpha-tomatine attenuation of in vivo growth of subcutaneous and orthotopic xenograft tumors of human prostate carcinoma PC-3 cells is accompanied by inactivation of nuclear factor-kappa B signaling. PLoS One. 2013;8(2):e57708. doi: 10.1371/journal.pone.0057708. Epub 2013 Feb 21. PubMed PMID: 23437404; PubMed Central PMCID: PMC3578807.

11: Kim SP, Nam SH, Friedman M. The Tomato Glycoalkaloid α-Tomatine Induces Caspase-Independent Cell Death in Mouse Colon Cancer CT-26 Cells and Transplanted Tumors in Mice. J Agric Food Chem. 2015 Jan 23. [Epub ahead of print] PubMed PMID: 25614934.

12: Chao MW, Chen CH, Chang YL, Teng CM, Pan SL. α-Tomatine-mediated anti-cancer activity in vitro and in vivo through cell cycle- and caspase-independent pathways. PLoS One. 2012;7(9):e44093. doi: 10.1371/journal.pone.0044093. Epub 2012 Sep 6. PubMed PMID: 22970166; PubMed Central PMCID: PMC3435411.

13: Lee ST, Wong PF, Hooper JD, Mustafa MR. Alpha-tomatine synergises with paclitaxel to enhance apoptosis of androgen-independent human prostate cancer PC-3 cells in vitro and in vivo. Phytomedicine. 2013 Nov 15;20(14):1297-305. doi: 10.1016/j.phymed.2013.07.002. Epub 2013 Aug 4. PubMed PMID: 23920276.

14: Raj V, Johnson T, Joseph K. Cholesterol aided etching of tomatine gold nanoparticles: a non-enzymatic blood cholesterol monitor. Biosens Bioelectron. 2014 Oct 15;60:191-4. doi: 10.1016/j.bios.2014.03.062. Epub 2014 Apr 23. PubMed PMID: 24811192.

15: Shi MD, Shih YW, Lee YS, Cheng YF, Tsai LY. Suppression of 12-O-tetradecanoylphorbol-13-acetate-induced MCF-7 breast adenocarcinoma cells invasion/migration by α-tomatine through activating PKCα/ERK/NF-κB-dependent MMP-2/MMP-9 expressions. Cell Biochem Biophys. 2013 May;66(1):161-74. doi: 10.1007/s12013-012-9465-8. PubMed PMID: 23114726.

16: Ohyama K, Okawa A, Fujimoto Y. Biosynthesis of steroidal alkaloids in Solanaceae plants: incorporation of 3β-hydroxycholest-5-en-26-al into tomatine with tomato seedlings. Bioorg Med Chem Lett. 2014 Aug 1;24(15):3556-8. doi: 10.1016/j.bmcl.2014.05.048. Epub 2014 May 23. PubMed PMID: 24909078.

17: Friedman M. Anticarcinogenic, cardioprotective, and other health benefits of tomato compounds lycopene, α-tomatine, and tomatidine in pure form and in fresh and processed tomatoes. J Agric Food Chem. 2013 Oct 9;61(40):9534-50. doi: 10.1021/jf402654e. Epub 2013 Sep 30. Review. PubMed PMID: 24079774.

18: Shieh JM, Cheng TH, Shi MD, Wu PF, Chen Y, Ko SC, Shih YW. α-Tomatine suppresses invasion and migration of human non-small cell lung cancer NCI-H460 cells through inactivating FAK/PI3K/Akt signaling pathway and reducing binding activity of NF-κB. Cell Biochem Biophys. 2011 Jul;60(3):297-310. doi: 10.1007/s12013-011-9152-1. PubMed PMID: 21264526.

19: Liu J, Kanetake S, Wu YH, Tam C, Cheng LW, Land KM, Friedman M. Antiprotozoal Effects of the Tomato Tetrasaccharide Glycoalkaloid Tomatine and the Aglycone Tomatidine on Mucosal Trichomonads. J Agric Food Chem. 2016 Nov 23;64(46):8806-8810. Epub 2016 Nov 11. PubMed PMID: 27934291.

20: Medina JM, Rodrigues JC, Moreira OC, Atella G, Souza Wd, Barrabin H. Mechanisms of growth inhibition of Phytomonas serpens by the alkaloids tomatine and tomatidine. Mem Inst Oswaldo Cruz. 2015 Feb;110(1):48-55. doi: 10.1590/0074-02760140097. Epub 2015 Feb 13. PubMed PMID: 25742263; PubMed Central PMCID: PMC4371217.