Tomatidine

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Contents

Tomatidine
Tomatidine.svg
Names
IUPAC name
(1R,2S,4S,5′S,6S,7S,8R,9S,12S,13S,16S,18S)-5′,7,9,13-tetramethylspiro[5-oxapentacyclo[10.8.0.02,9.04,8.013,18]icosane-6,2′-piperidine]-16-ol
Other names
  • 5alpha-Tomatidan-3beta-ol
  • (3beta,5alpha,22beta,25S)-Spirosolan-3-ol
  • Tomatidin
  • (22S,25S)-5alpha-spirosolan-3beta-ol
Identifiers
3D model (JSmol)
91747
ChEBI
ChEMBL
ChemSpider
ECHA InfoCard 100.000.947 OOjs UI icon edit-ltr-progressive.svg
EC Number
  • 201-040-3
KEGG
PubChem CID
UNII
  • InChI=1S/C27H45NO2/c1-16-7-12-27(28-15-16)17(2)24-23(30-27)14-22-20-6-5-18-13-19(29)8-10-25(18,3)21(20)9-11-26(22,24)4/h16-24,28-29H,5-15H2,1-4H3/t16-,17-,18-,19-,20+,21-,22-,23-,24-,25-,26-,27-/m0/s1
    Key: XYNPYHXGMWJBLV-VXPJTDKGSA-N
  • CC1CCC2(C(C3C(O2)CC4C3(CCC5C4CCC6C5(CCC(C6)O)C)C)C)NC1
Properties
C27H45NO2
Molar mass 415.662 g·mol−1
Hazards
GHS labelling:
GHS-pictogram-skull.svg GHS-pictogram-exclam.svg
Danger
H301, H302, H331
P261, P264, P270, P271, P301+P310, P301+P312, P304+P340, P311, P321, P330, P403+P233, P405, P501
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).

Tomatidine is a natural compound found in leaves of tomatoes and green tomatoes. [1] Chemically, it is the aglycone of tomatine. It has been shown to have potential health benefits in animal models. [2] For instance, tomatidine inhibited skeletal muscle atrophy in a mouse model of skeletal unloading-induced atrophy [3] and to prevent or reverse sarcopenia (loss of muscle mass and strength due to biological aging) by inhibiting the activation of genes by ATF4. [4]

Dietary supplementation with ~0.04% tomatidine for 10 weeks reduced plasma cholesterol and atherosclerosis in ApoE-deficient mice without evidence of toxicity. [5]

Research

It is investigated as compound to increase longevity and it increased lifespan and healthspan of C. elegans . [6] It is also investigated in osteoporosis. [7] [8]

See also

References

  1. ↑ "Green is good: Natural compound from green tomatoes increases muscle, protects against muscle wasting".
  2. ↑ Friedman M (2013). "Anticarcinogenic, Cardioprotective, and Other Health Benefits of Tomato Compounds Lycopene, α-Tomatine, and Tomatidine in Pure Form and in Fresh and Processed Tomatoes". Journal of Agricultural and Food Chemistry. 61 (40): 9534–50. Bibcode:2013JAFC...61.9534F. doi:10.1021/jf402654e. PMID   24079774.
  3. ↑ Dyle MC, Ebert SM, Cook DP, Kunkel SD, Fox DK, Bongers KS, Bullard SA, Dierdorff JM, Adams CM (2014). "Systems-based Discovery of Tomatidine as a Natural Small Molecule Inhibitor of Skeletal Muscle Atrophy". Journal of Biological Chemistry. 289 (21): 14913–14924. doi: 10.1074/jbc.M114.556241 . PMC   4031541 . PMID   24719321.
  4. ↑ Ebert SM, Dyle MC, Bullard SA, Dierdorff JM, Murry DJ, Fox DK, Bongers KS, Lira VA, Meyerholz DK, Talley JJ, Adams CM (2015). "Identification and Small Molecule Inhibition of an Activating Transcription Factor 4 (ATF4)-dependent Pathway to Age-related Skeletal Muscle Weakness and Atrophy". Journal of Biological Chemistry. 290 (42): 25497–25511. doi: 10.1074/jbc.M115.681445 . PMC   4646196 . PMID   26338703.
  5. ↑ Fujiwara Y, Kiyota N, Tsurushima K, Yoshitomi M, Horlad H, Ikeda T, Nohara T, Takeya M, Nagai R (2012). "Tomatidine, a tomato sapogenol, ameliorates hyperlipidemia and atherosclerosis in apoE-deficient mice by inhibiting acyl-CoA:cholesterol acyl-transferase (ACAT)". Journal of Agricultural and Food Chemistry. 60 (10): 2472–9. Bibcode:2012JAFC...60.2472F. doi:10.1021/jf204197r. PMID   22224814.
  6. ↑ Fang EF, Waltz TB, Kassahun H, Lu Q, Kerr JS, Morevati M, Fivenson EM, Wollman BN, Marosi K, Wilson MA, Iser WB, Eckley DM, Zhang Y, Lehrmann E, Goldberg IG, Scheibye-Knudsen M, Mattson MP, Nilsen H, Bohr VA, Becker KG (April 2017). "Tomatidine enhances lifespan and healthspan in C. elegans through mitophagy induction via the SKN-1/Nrf2 pathway". Scientific Reports . 7 46208. Bibcode:2017NatSR...746208F. doi:10.1038/srep46208. PMC   5387417 . PMID   28397803.
  7. ↑ Hu B, Sun X, Yang Y, Ying Z, Meng J, Zhou C, Jiang G, Li S, Wu F, Zhao X, Zhu H, Wu H, Cai X, Shi Z, Yan S (February 2019). "Tomatidine suppresses osteoclastogenesis and mitigates estrogen deficiency-induced bone mass loss by modulating TRAF6-mediated signaling". FASEB Journal . 33 (2): 2574–2586. doi: 10.1096/fj.201800920R . PMID   30285579. S2CID   52918610.
  8. ↑ Yu T, Wu Q, You X, Zhou H, Xu S, He W, Li Z, Li B, Xia J, Zhu H, Zhao Y, Yang Y, Chen K (April 2020). "Tomatidine Alleviates Osteoporosis by Downregulation of p53". Medical Science Monitor. 26 e923996. doi:10.12659/MSM.923996. PMC   7191956 . PMID   32300098.
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