A steroidal saponin with diverse biological activities
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Tomatine

Item No. 16024

Product Insert (PDF)Safety Data Sheet (SDS) (PDF)
Technical Information
Formal Name
(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
CAS Number
17406-45-0
Synonyms
  • Lycopersicin
  • NSC 9223
  • NSC 234440
  • α-Tomatine
Molecular Formula
C50H83NO21
Formula Weight
1034.2
Purity
≥95%
Formulation (Request formulation change)
A solid
Solubility(Learn about Variance in Solubility)
DMSO: 2 mg/ml
SMILES
C[C@H]1CC[C@@]2(O[C@]3(C[C@]4([C@@]5(CC[C@]6(C[C@H](CC[C@@]6([C@]5(CC[C@@]4([C@]3([C@@H]2C)[H])C)[H])C)O[C@@]7(O[C@@H]([C@@H]([C@@H]([C@H]7O)O)O[C@]8([C@@H]([C@H]([C@@H]([C@H](O8)CO)O)O[C@]9([C@@H]([C@H]([C@@H](CO9)O)O)O)[H])O[C@@]%10(O[C@@H]([C@H]([
InChi Code
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)1
InChi Key
REJLGAUYTKNVJM-SGXCCWNXSA-N
Origin
Plant/Tomato
Shipping & Storage Information
Storage
-20°C
Shipping
Room temperature in continental US; may vary elsewhere
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    5 mg

    $63

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    10 mg

    $119

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    25 mg

    $279

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    50 mg

    $433

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    Cayman Chemical
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    Product Description

    Tomatine is a steroidal saponin that has been found in S. lycopersicum and has diverse biological activities.1,2,3,4 It is active against a panel of 19 plant pathogenic fungi (EC50s = 13-912 µM) and inhibits the growth of L. amazonensis promastigotes (IC50 = 124 nM).1,2 Tomatine (0.75, 1, and 1.5 µM) inhibits autophagy and induces apoptosis in SKOV3 ovarian cancer cells.3 Dietary administration of tomatine (0.1 and 0.2% w/w) decreases serum LDL levels and increases fecal cholesterol secretion in hamsters.4

    WARNING This product is not for human or veterinary use.

    References & Product Citations
    Product Description References

    1. Sandrock, R.W., and Vanetten, H.D. Fungal sensitivity to and enzymatic degradation of the phytoanticipin α-tomatine. Phytopathology 88(2), 137-143 (1998).

    2. 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. 61(40), 9534-9550 (2013).

    3. Wu, H., Li, W., Wang, T., et al. α-Tomatine, a novel early-stage autophagy inhibitor, inhibits autophagy to enhance apoptosis via Beclin-1 in Skov3 cells. Fitoterapia 152, 104911 (2021).

    4. Friedman, M., Fitch, T.E., and Yokoyama, W.E. Lowering of plasma LDL cholesterol in hamsters by the tomato glycoalkaloid tomatine. Food Chem. Toxicol. 38(7), 549-553 (2000).