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MedKoo Cat#: 525238 | Name: Dehydroleucodin
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Description:

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

Dehydroleucodin is an inducer of cell cycle arrest, senescence and apoptosis, inhibiting tumor growth in a preclinical melanoma model.

Chemical Structure

Dehydroleucodin
Dehydroleucodin
CAS#36150-07-9

Theoretical Analysis

MedKoo Cat#: 525238

Name: Dehydroleucodin

CAS#: 36150-07-9

Chemical Formula: C15H16O3

Exact Mass: 244.1099

Molecular Weight: 244.29

Elemental Analysis: C, 73.75; H, 6.60; O, 19.65

Price and Availability

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5mg USD 350.00 Back order
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Related CAS #
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Synonym
Dehydroleucodin; Dehydroleucodine; NSC 180034; NSC180034; NSC-180034
IUPAC/Chemical Name
(3aS,9aS,9bS)-6,9-Dimethyl-3-methylidene-4,5,9a,9b-tetrahydro-3aH-azuleno[4,5-b]furan-2,7-dione
InChi Key
SKNVIAFTENCNGB-BPNCWPANSA-N
InChi Code
InChI=1S/C15H16O3/c1-7-4-5-10-9(3)15(17)18-14(10)13-8(2)6-11(16)12(7)13/h6,10,13-14H,3-5H2,1-2H3/t10-,13-,14-/m0/s1
SMILES Code
O=C(O[C@@]1([H])[C@@]2([H])CCC(C)=C3C(C=C(C)[C@@]31[H])=O)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
>2 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 244.29 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: Bailon-Moscoso N, González-Arévalo G, Velásquez-Rojas G, Malagon O, Vidari G, Zentella-Dehesa A, Ratovitski EA, Ostrosky-Wegman P. Correction: Phytometabolite Dehydroleucodine Induces Cell Cycle Arrest, Apoptosis, and DNA Damage in Human Astrocytoma Cells through p73/p53 Regulation. PLoS One. 2017 Mar 9;12(3):e0173648. doi: 10.1371/journal.pone.0173648. eCollection 2017. PubMed PMID: 28278226; PubMed Central PMCID: PMC5344509. 2: Zapata-Martínez J, Sánchez-Toranzo G, Chaín F, Catalán CA, Bühler MI. Effect of guaianolides in the meiosis reinitiation of amphibian oocytes. Zygote. 2017 Feb;25(1):10-16. doi: 10.1017/S0967199416000265. Epub 2016 Nov 3. PubMed PMID: 27806737. 3: Ratovitski EA. Dehydroleucodine induces a TP73-dependent transcriptional regulation of multiple cell death target genes in human glioblastoma cells. Anticancer Agents Med Chem. 2016 Sep 23. [Epub ahead of print] PubMed PMID: 27671304. 4: Ordóñez PE, Sharma KK, Bystrom LM, Alas MA, Enriquez RG, Malagón O, Jones DE, Guzman ML, Compadre CM. Dehydroleucodine, a Sesquiterpene Lactone from Gynoxys verrucosa, Demonstrates Cytotoxic Activity against Human Leukemia Cells. J Nat Prod. 2016 Apr 22;79(4):691-6. doi: 10.1021/acs.jnatprod.5b00383. Epub 2016 Apr 8. PubMed PMID: 27057812. 5: Costantino VV, Lobos-Gonzalez L, Ibañez J, Fernandez D, Cuello-Carrión FD, Valenzuela MA, Barbieri MA, Semino SN, Jahn GA, Quest AF, Lopez LA. Dehydroleucodine inhibits tumor growth in a preclinical melanoma model by inducing cell cycle arrest, senescence and apoptosis. Cancer Lett. 2016 Mar 1;372(1):10-23. doi: 10.1016/j.canlet.2015.12.004. Epub 2015 Dec 21. PubMed PMID: 26718258. 6: Mustafi S, Veisaga ML, López LA, Barbieri MA. A Novel Insight into Dehydroleucodine Mediated Attenuation of Pseudomonas aeruginosa Virulence Mechanism. Biomed Res Int. 2015;2015:216097. doi: 10.1155/2015/216097. Epub 2015 Nov 16. PubMed PMID: 26640783; PubMed Central PMCID: PMC4658400. 7: Zapata-Martínez J, Medina MF, Gramajo-Bühler MC, Sánchez-Toranzo G. Participation of PLA2 and PLC in DhL-induced activation of Rhinella arenarum oocytes. Zygote. 2016 Aug;24(4):495-501. doi: 10.1017/S096719941500043X. Epub 2015 Sep 9. PubMed PMID: 26350822. 8: Bailon-Moscoso N, González-Arévalo G, Velásquez-Rojas G, Malagon O, Vidari G, Zentella-Dehesa A, Ratovitski EA, Ostrosky-Wegman P. Phytometabolite Dehydroleucodine Induces Cell Cycle Arrest, Apoptosis, and DNA Damage in Human Astrocytoma Cells through p73/p53 Regulation. PLoS One. 2015 Aug 26;10(8):e0136527. doi: 10.1371/journal.pone.0136527. eCollection 2015. Erratum in: PLoS One. 2017 Mar 9;12 (3):e0173648. PubMed PMID: 26309132; PubMed Central PMCID: PMC4550445. 9: Medina MF, Bühler MI, Sánchez-Toranzo G. Chemical activation in Rhinella arenarum oocytes: effect of dehydroleucodine (DhL) and its hydrogenated derivative (2H-DhL). Zygote. 2015 Dec;23(6):924-32. doi: 10.1017/S0967199414000641. Epub 2014 Nov 26. PubMed PMID: 25424172. 10: Jimenez V, Kemmerling U, Paredes R, Maya JD, Sosa MA, Galanti N. Natural sesquiterpene lactones induce programmed cell death in Trypanosoma cruzi: a new therapeutic target? Phytomedicine. 2014 Sep 25;21(11):1411-8. doi: 10.1016/j.phymed.2014.06.005. Epub 2014 Jul 8. PubMed PMID: 25022207. 11: Barrera P, Sülsen VP, Lozano E, Rivera M, Beer MF, Tonn C, Martino VS, Sosa MA. Natural Sesquiterpene Lactones Induce Oxidative Stress in Leishmania mexicana. Evid Based Complement Alternat Med. 2013;2013:163404. doi: 10.1155/2013/163404. Epub 2013 Jun 4. PubMed PMID: 23861697; PubMed Central PMCID: PMC3687511. 12: Costantino VV, Mansilla SF, Speroni J, Amaya C, Cuello-Carrión D, Ciocca DR, Priestap HA, Barbieri MA, Gottifredi V, Lopez LA. The sesquiterpene lactone dehydroleucodine triggers senescence and apoptosis in association with accumulation of DNA damage markers. PLoS One. 2013;8(1):e53168. doi: 10.1371/journal.pone.0053168. Epub 2013 Jan 14. PubMed PMID: 23341930; PubMed Central PMCID: PMC3544853. 13: Lozano E, Barrera P, Salinas R, Vega I, Nieto M, Tonn C, Kemmerling U, Mortara RA, Sosa MA. Sesquiterpene lactones and the diterpene 5-epi-icetexone affect the intracellular and extracellular stages of Trypanosoma cruzi. Parasitol Int. 2012 Dec;61(4):628-33. doi: 10.1016/j.parint.2012.06.005. Epub 2012 Jun 23. PubMed PMID: 22735296. 14: Bevacqua RJ, Pereyra-Bonnet F, Olivera R, Hiriart MI, Sipowicz P, Fernandez-Martín R, Radrizzani M, Salamone DF. Production of IVF transgene-expressing bovine embryos using a novel strategy based on cell cycle inhibitors. Theriogenology. 2012 Jul 1;78(1):57-68. doi: 10.1016/j.theriogenology.2012.01.020. Epub 2012 Apr 10. PubMed PMID: 22494679. 15: Vera ME, Persia FA, Mariani ML, Rudolph MI, Fogal TH, Ceñal JP, Favier LS, Tonn CE, Penissi AB. Activation of human leukemic mast cell line LAD2 is modulated by dehydroleucodine and xanthatin. Leuk Lymphoma. 2012 Sep;53(9):1795-803. doi: 10.3109/10428194.2012.662644. Epub 2012 May 29. PubMed PMID: 22300345. 16: Moreno LE, Juárez AO, Pelzer LE. Lethal effect of dehydroleucodine (DhL) on amphibian Bufo arenarum embryos. Food Chem Toxicol. 2012 Mar;50(3-4):672-4. doi: 10.1016/j.fct.2011.12.037. Epub 2012 Jan 3. PubMed PMID: 22240414. 17: Galvis A, Marcano A, Stefancin C, Villaverde N, Priestap HA, Tonn CE, Lopez LA, Barbieri MA. The effect of dehydroleucodine in adipocyte differentiation. Eur J Pharmacol. 2011 Dec 5;671(1-3):18-25. doi: 10.1016/j.ejphar.2011.09.033. Epub 2011 Sep 19. PubMed PMID: 21963454; PubMed Central PMCID: PMC3401420. 18: Ordóñez PE, Quave CL, Reynolds WF, Varughese KI, Berry B, Breen PJ, Malagón O, Smeltzer MS, Compadre CM. Sesquiterpene lactones from Gynoxys verrucosa and their anti-MRSA activity. J Ethnopharmacol. 2011 Sep 2;137(2):1055-9. doi: 10.1016/j.jep.2011.07.012. Epub 2011 Jul 12. PubMed PMID: 21782013; PubMed Central PMCID: PMC3159821. 19: Suhaiman L, Carlos de-Rosas J, Sartor T, Palmada N, Giordano OS, Lopez LA. Effect of dehydroleucodine on the reproductive tract of male mice. Andrologia. 2011 Oct;43(5):297-302. doi: 10.1111/j.1439-0272.2010.01053.x. Epub 2011 Jun 30. PubMed PMID: 21714796. 20: Wendel GH, María AO, Aguilar CF, Pelzer LE. Effect of dehydroleucodine on intestinal transit: structural basis of the interaction with the α(2)-adrenergic receptor. Eur Biophys J. 2011 Aug;40(8):981-6. doi: 10.1007/s00249-011-0716-1. Epub 2011 Jun 14. PubMed PMID: 21671152.