Tomatidine

{{cs1 config|name-list-style=vanc}} {{Chembox | ImageFile = Tomatidine.svg | ImageSize = 250px | IUPACName = (1''R'',2''S'',4''S'',5{{prime}}''S'',6''S'',7''S'',8''R'',9''S'',12''S'',13''S'',16''S'',18''S'')-5{{prime}},7,9,13-tetramethylspiro[5-oxapentacyclo[10.8.0.02,9.04,8.013,18]icosane-6,2{{prime}}-piperidine]-16-ol | OtherNames = {{Unbulleted list | 5alpha-Tomatidan-3beta-ol | (3beta,5alpha,22beta,25S)-Spirosolan-3-ol | Tomatidin | (22S,25S)-5alpha-spirosolan-3beta-ol }} | Section1={{Chembox Identifiers | index_label =  | CASNo_Ref = | CASNo = 77-59-8 | CASNo1 = 6192-62-7 | Beilstein = 91747 | ChEBI = 9629 | ChEMBL = 2165711 | ChemSpiderID = 59019 | EINECS = 201-040-3 | KEGG = C10826 | PubChem = 65576 | UNII_Ref = | UNII = 2B73S48786 | StdInChI = 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 | StdInChIKey = XYNPYHXGMWJBLV-VXPJTDKGSA-N | SMILES = CC1CCC2(C(C3C(O2)CC4C3(CCC5C4CCC6C5(CCC(C6)O)C)C)C)NC1 }} |Section2={{Chembox Properties | C=27 | H=45 | N=1 |O=2 }} |Section7={{Chembox Hazards | GHSPictograms = {{GHS06}}{{GHS07}} | GHSSignalWord = Danger | HPhrases = {{H-phrases|301|302|331}} | PPhrases = {{P-phrases|261|264|270|271|301+310|301+312|304+340|311|321|330|403+233|405|501}} }} }}

'''Tomatidine''' is a natural compound found in leaves of tomatoes and green tomatoes.<ref name="sciencedailytomatidine">{{Cite web|url=https://www.sciencedaily.com/releases/2014/04/140409134638.htm|title = Green is good: Natural compound from green tomatoes increases muscle, protects against muscle wasting}}</ref> Chemically, it is the aglycone of tomatine. It has been shown to have potential health benefits in animal models.<ref>{{cite journal |last1=Friedman |first1=Mendel |year=2013 |title=Anticarcinogenic, Cardioprotective, and Other Health Benefits of Tomato Compounds Lycopene, α-Tomatine, and Tomatidine in Pure Form and in Fresh and Processed Tomatoes |journal=Journal of Agricultural and Food Chemistry |volume=61 |issue=40 |pages= 9534–50|pmid=24079774 |doi=10.1021/jf402654e |bibcode=2013JAFC...61.9534F }}</ref> For instance, tomatidine inhibited skeletal muscle atrophy in a mouse model of skeletal unloading-induced atrophy<ref>{{Cite journal|pmc=4031541|year=2014|last1=Dyle|first1=M. C.|title=Systems-based Discovery of Tomatidine as a Natural Small Molecule Inhibitor of Skeletal Muscle Atrophy|journal=Journal of Biological Chemistry|volume=289|issue=21|pages=14913–14924|last2=Ebert|first2=S. M.|last3=Cook|first3=D. P.|last4=Kunkel|first4=S. D.|last5=Fox|first5=D. K.|last6=Bongers|first6=K. S.|last7=Bullard|first7=S. A.|last8=Dierdorff|first8=J. M.|last9=Adams|first9=C. M.|doi=10.1074/jbc.M114.556241|pmid=24719321|doi-access=free}}</ref> and to prevent or reverse sarcopenia (loss of muscle mass and strength due to biological aging) by inhibiting the activation of genes by ATF4.<ref>{{Cite journal|pmc=4646196|year=2015|last1=Ebert|first1=S. M.|title=Identification and Small Molecule Inhibition of an Activating Transcription Factor 4 (ATF4)-dependent Pathway to Age-related Skeletal Muscle Weakness and Atrophy|journal=Journal of Biological Chemistry|volume=290|issue=42|pages=25497–25511|last2=Dyle|first2=M. C.|last3=Bullard|first3=S. A.|last4=Dierdorff|first4=J. M.|last5=Murry|first5=D. J.|last6=Fox|first6=D. K.|last7=Bongers|first7=K. S.|last8=Lira|first8=V. A.|last9=Meyerholz|first9=D. K. |last10=Talley|first10=J. J.|last11=Adams|first11=C. M.|doi=10.1074/jbc.M115.681445|pmid=26338703|doi-access=free}}</ref>

Dietary supplementation with ~0.04% tomatidine for 10 weeks reduced plasma cholesterol and atherosclerosis in ApoE-deficient mice without evidence of toxicity.<ref>{{Cite journal|pmid=22224814|year=2012|last1=Fujiwara|first1=Y|title=Tomatidine, a tomato sapogenol, ameliorates hyperlipidemia and atherosclerosis in apoE-deficient mice by inhibiting acyl-CoA:cholesterol acyl-transferase (ACAT)|journal=Journal of Agricultural and Food Chemistry|volume=60|issue=10|pages=2472–9|last2=Kiyota|first2=N|last3=Tsurushima|first3=K|last4=Yoshitomi|first4=M|last5=Horlad|first5=H|last6=Ikeda|first6=T|last7=Nohara|first7=T|last8=Takeya|first8=M|last9=Nagai|first9=R|doi=10.1021/jf204197r |bibcode=2012JAFC...60.2472F }}</ref>

== Research == It is investigated as compound to increase longevity and it increased lifespan and healthspan of ''C. elegans''.<ref name="pmid28397803">{{cite journal |vauthors=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 |title=Tomatidine enhances lifespan and healthspan in C. elegans through mitophagy induction via the SKN-1/Nrf2 pathway |journal=Scientific Reports |volume=7 |issue= |article-number=46208 |date=April 2017 |pmid=28397803 |pmc=5387417 |doi=10.1038/srep46208 |bibcode=2017NatSR...746208F |url= |issn=}}</ref> It is also investigated in osteoporosis.<ref name="pmid30285579">{{cite journal |vauthors=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 |title=Tomatidine suppresses osteoclastogenesis and mitigates estrogen deficiency-induced bone mass loss by modulating TRAF6-mediated signaling |journal=FASEB Journal |volume=33 |issue=2 |pages=2574–2586 |date=February 2019 |pmid=30285579 |doi=10.1096/fj.201800920R |doi-access=free |s2cid=52918610 |url= |issn=}}</ref><ref name="pmid32300098">{{cite journal |vauthors=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 |title=Tomatidine Alleviates Osteoporosis by Downregulation of p53 |journal= Medical Science Monitor |volume=26 |issue= |article-number=e923996 |date=April 2020 |pmid=32300098 |pmc=7191956 |doi=10.12659/MSM.923996 |url= |issn=}}</ref>

== See also == * Ursolic acid

== References == {{Reflist}}

Category:Heterocyclic compounds with 5 rings Category:Piperidines Category:Oxygen heterocycles Category:Spiro compounds