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MedKoo Cat#: 462002 | Name: Tomentosin
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Description:

WARNING: This product is for research use only, not for human or veterinary use.

Tomentosin, a sesquiterpene lactone primarily isolated from Inula viscosa and related plant species, exhibits a range of bioactivities, including anticancer, anti-inflammatory, and antimicrobial effects. Studies have shown that tomentosin induces apoptosis and inhibits proliferation in various cancer cell lines, such as breast, lung, and colon cancers, by modulating pathways like NF-κB, STAT3, and MAPK. Its anti-inflammatory properties are linked to the suppression of pro-inflammatory cytokines and oxidative stress, making it a potential candidate for inflammatory disease treatment. Additionally, tomentosin has demonstrated antimicrobial activity against bacteria and fungi.

Chemical Structure

Tomentosin
CAS#33649-15-9

Theoretical Analysis

MedKoo Cat#: 462002

Name: Tomentosin

CAS#: 33649-15-9

Chemical Formula: C15H20O3

Exact Mass: 248.1412

Molecular Weight: 248.32

Elemental Analysis: C, 72.55; H, 8.12; O, 19.33

Price and Availability

Size Price Availability Quantity
1mg USD 850.00 2 Weeks
5mg USD 1,750.00 2 Weeks
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Related CAS #
No Data
Synonym
Tomentosin; 6-Deacetoxybritanlin G; Xanthalongi
IUPAC/Chemical Name
(3aR,7S,8aR)-7-methyl-3-methylidene-6-(3-oxobutyl)-4,7,8,8a-tetrahydro-3aH-cyclohepta[b]furan-2-one
InChi Key
AVFIYMSJDDGDBQ-CUOATXAZSA-N
InChi Code
InChI=1S/C15H20O3/c1-9-8-14-13(11(3)15(17)18-14)7-6-12(9)5-4-10(2)16/h6,9,13-14H,3-5,7-8H2,1-2H3/t9-,13+,14+/m0/s1
SMILES Code
O=C(O[C@@]1([H])[C@]2([H])CC=C(CCC(C)=O)[C@@H](C)C1)C2=C
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
>3 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

Preparing Stock Solutions

The following data is based on the product molecular weight 248.32 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
1: Ouari S, Benzidane N. Chemical composition, biological activities, and molecular mechanism of Inula viscosa (L.) bioactive compounds: a review. Naunyn Schmiedebergs Arch Pharmacol. 2024 Jun;397(6):3857-3865. doi: 10.1007/s00210-023-02930-7. Epub 2024 Jan 5. PMID: 38180555. 2: Pane C, Manganiello G, Vitti A, Celano R, Piccinelli AL, De Falco E. Phytochemical Extracts of Dittrichia viscosa (L.) Greuter from Agroecological Systems: Seed Antigerminative Properties and Effectiveness in Counteracting Alternaria Leaf Spot Disease on Baby-Leaf Spinach. Biology (Basel). 2023 May 30;12(6):790. doi: 10.3390/biology12060790. PMID: 37372075; PMCID: PMC10295540. 3: Di YX, Bao YJ, Zhu ZQ, Sun SL, Tian FX, Wang FR, Yu G, Zhang MF, Han J, Zhou LL. Tomentosin suppressed M1 polarization via increasing MERTK activation mediated by regulation of GAS6. J Ethnopharmacol. 2023 Oct 5;314:116429. doi: 10.1016/j.jep.2023.116429. Epub 2023 Apr 1. PMID: 37011736. 4: Migheli R, Virdis P, Galleri G, Arru C, Lostia G, Coradduzza D, Muroni MR, Pintore G, Podda L, Fozza C, De Miglio MR. Antineoplastic Properties by Proapoptotic Mechanisms Induction of Inula viscosa and Its Sesquiterpene Lactones Tomentosin and Inuviscolide. Biomedicines. 2022 Oct 28;10(11):2739. doi: 10.3390/biomedicines10112739. PMID: 36359261; PMCID: PMC9687476. 5: Güçlü E, Çınar Ayan İ, Dursun HG, Vural H. Tomentosin induces apoptosis in pancreatic cancer cells through increasing reactive oxygen species and decreasing mitochondrial membrane potential. Toxicol In Vitro. 2022 Oct;84:105458. doi: 10.1016/j.tiv.2022.105458. Epub 2022 Aug 19. PMID: 35988885. 6: Yang S, Park SH, Oh SW, Kwon K, Yu E, Lee CW, Son YK, Kim C, Lee BH, Cho JY, Kim YJ, Lee J. Antioxidant Activities and Mechanisms of Tomentosin in Human Keratinocytes. Antioxidants (Basel). 2022 May 18;11(5):990. doi: 10.3390/antiox11050990. PMID: 35624854; PMCID: PMC9137523. 7: Zaki M, Loubidi M, Bilgiç T, Birim D, Akssira M, Dagcı T, Berteina-Raboin S, Saso L, Khouili M, Armagan G. Design, Synthesis, and Biological Evaluation of Novel Tomentosin Derivatives in NMDA-Induced Excitotoxicity. Pharmaceuticals (Basel). 2022 Mar 30;15(4):421. doi: 10.3390/ph15040421. PMID: 35455419; PMCID: PMC9027110. 8: Han J, Zhang S, Jiang B, Wang J, Ge X, Wu B, Zhang S, Wang D. Sesquiterpene lactones from Xanthium sibiricum Patrin alleviate asthma by modulating the Th1/Th2 balance in a murine model. Phytomedicine. 2022 May;99:154032. doi: 10.1016/j.phymed.2022.154032. Epub 2022 Mar 3. PMID: 35263672. 9: Aydin T, Saglamtas R, Dogan B, Kostekci E, Durmus R, Cakir A. A new specific method for isolation of tomentosin with a high yield from Inula viscosa (L.) and determination of its bioactivities. Phytochem Anal. 2022 Jun;33(4):612-618. doi: 10.1002/pca.3114. Epub 2022 Mar 4. PMID: 35243708. 10: Ponticelli M, Lela L, Russo D, Faraone I, Sinisgalli C, Mustapha MB, Esposito G, Jannet HB, Costantino V, Milella L. Dittrichia graveolens (L.) Greuter, a Rapidly Spreading Invasive Plant: Chemistry and Bioactivity. Molecules. 2022 Jan 28;27(3):895. doi: 10.3390/molecules27030895. PMID: 35164160; PMCID: PMC8840657. 11: Virdis P, Marchesi I, Fiorentino FP, Migheli R, Sanna L, Bordoni V, Pintore G, Galleri G, Muroni MR, Bagella L, Fozza C, De Miglio MR, Podda L. Tomentosin a Sesquiterpene Lactone Induces Antiproliferative and Proapoptotic Effects in Human Burkitt Lymphoma by Deregulation of Anti- and Pro-Apoptotic Genes. Life (Basel). 2021 Oct 23;11(11):1128. doi: 10.3390/life11111128. PMID: 34833004; PMCID: PMC8623649. 12: Virdis P, Migheli R, Bordoni V, Fiorentino FP, Sanna L, Marchesi I, Pintore G, Galleri G, Muroni MR, Bagella L, Fozza C, De Miglio MR, Podda L. Clarifying the molecular mechanism of tomentosin‑induced antiproliferative and proapoptotic effects in human multiple myeloma via gene expression profile and genetic interaction network analysis. Int J Mol Med. 2021 Dec;48(6):213. doi: 10.3892/ijmm.2021.5046. Epub 2021 Oct 13. PMID: 34643251; PMCID: PMC8522960. 13: El Yaagoubi OM, Lahmadi A, Bouyahya A, Filali H, Samaki H, El Antri S, Aboudkhil S. Antitumor Effect of Inula viscosa Extracts on DMBA-Induced Skin Carcinoma Are Mediated by Proteasome Inhibition. Biomed Res Int. 2021 Mar 27;2021:6687589. doi: 10.1155/2021/6687589. PMID: 33855081; PMCID: PMC8019636. 14: Fan Y, Maghimaa M, Chinnathambi A, Alharbi SA, Veeraraghavan VP, Mohan SK, Hussain S, Rengarajan T. Tomentosin Reduces Behavior Deficits and Neuroinflammatory Response in MPTP-Induced Parkinson's Disease in Mice. J Environ Pathol Toxicol Oncol. 2021;40(1):75-84. doi: 10.1615/JEnvironPatholToxicolOncol.v40.i1.70. PMID: 33639075. 15: Rahimi M, Bouwmeester H. Are sesquiterpene lactones the elusive KARRIKIN- INSENSITIVE2 ligand? Planta. 2021 Feb 1;253(2):54. doi: 10.1007/s00425-021-03571-x. PMID: 33521891; PMCID: PMC7847861. 16: Yang L, Xie J, Almoallim HS, Alharbi SA, Chen Y. Tomentosin inhibits cell proliferation and induces apoptosis in MOLT-4 leukemia cancer cells through the inhibition of mTOR/PI3K/Akt signaling pathway. J Biochem Mol Toxicol. 2021 Apr;35(4):e22719. doi: 10.1002/jbt.22719. Epub 2021 Jan 27. PMID: 33501684. 17: Zhu H, Wang Y, Sun J, Fan C, Wan J. Tomentosin Inhibits Lipopolysaccharide- Induced Acute Lung Injury and Inflammatory Response by Suppression of the NF-κB Pathway in a Mouse Model of Sepsis. J Environ Pathol Toxicol Oncol. 2020;39(4):291-298. doi: 10.1615/JEnvironPatholToxicolOncol.2020035116. PMID: 33389901. 18: He J, Wu H, Zhou Y, Zheng C. Tomentosin inhibit cerebral ischemia/reperfusion induced inflammatory response via TLR4/ NLRP3 signalling pathway - in vivo and in vitro studies. Biomed Pharmacother. 2020 Nov;131:110697. doi: 10.1016/j.biopha.2020.110697. Epub 2020 Sep 9. PMID: 32919189. 19: Yu SH, Lee CM, Ha SH, Lee J, Jang KY, Park SH. Induction of cell cycle arrest and apoptosis by tomentosin in hepatocellular carcinoma HepG2 and Huh7 cells. Hum Exp Toxicol. 2021 Feb;40(2):231-244. doi: 10.1177/0960327120943935. Epub 2020 Aug 13. PMID: 32787465. 20: Spring O, Schmauder K, Lackus ND, Schreiner J, Meier C, Wellhausen J, Smith LV, Frey M. Spatial and developmental synthesis of endogenous sesquiterpene lactones supports function in growth regulation of sunflower. Planta. 2020 Jun 5;252(1):2. doi: 10.1007/s00425-020-03409-y. PMID: 32504343; PMCID: PMC7275010.
Fan Y, Maghimaa M, Chinnathambi A, Alharbi SA, Veeraraghavan VP, Mohan SK, Hussain S, Rengarajan T. Tomentosin Reduces Behavior Deficits and Neuroinflammatory Response in MPTP-Induced Parkinson's Disease in Mice. J Environ Pathol Toxicol Oncol. 2021;40(1):75-84. doi: 10.1615/JEnvironPatholToxicolOncol.v40.i1.70. PMID: 33639075.