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Structure Database (LMSD)

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Common Name

tomatine

Systematic Name

(22S,25S)-5α-spirosolan-3β-yl β-D-glucopyranosyl-(1-2)-[β-D-xylopyranosyl-(1-3)]-β-D-glucopyranosyl-(1-4)-β-D-galactopyranoside

Synonyms

(3beta,5alpha,22beta,25S)-spirosolan-3-yl O-beta-D-glucopyranosyl-(1->2)-O-(beta-D-xylopyranosyl)-(1->3)-O-beta-D-glucopyranosyl-(1->4)-beta-D-galactopyranoside
A''-Tomatidine
Tomatine
alpha-tomatine
lycopersicin

LM ID

LMST01150015

Formula

C₅₀H₈₃NO₂₁

Exact Mass

Calculate m/z

1033.545764

Status

Curated

Show lipids differing only in stereochemistry/bond geometry

Classification

Biological Context

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

This information has been provided by Cayman Chemical

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).

String Representations

InChiKey (Click to copy)

REJLGAUYTKNVJM-SGXCCWNXSA-N

InChi (Click to copy)

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

SMILES (Click to copy)

O([C@H]1CC[C@@]2(C)[C@]([H])(C1)CC[C@@]1([H])[C@@]3([H])[C@@](C)([C@@]4([H])[C@H](C)[C@@]5(O[C@@]4([H])C3)CC[C@H](C)CN5)CC[C@@]12[H])[C@@H]1O[C@H](CO)[C@H](O[C@@H]2O[C@H](CO)[C@@H](O)[C@H](O[C@@H]3OC[C@@H](O)[C@H](O)[C@H]3O)[C@H]2O[C@@H]2O[C@H](CO)[C@@H](O)[C@H](O)[C@H]2O)[C@H](O)[C@H]1O