Jatrophone

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

MedKoo CAT#: 596170

CAS#: 29444-03-9

Description: Jatrophone is a novel macrocyclic diterpenoid tumor inhibitor from Jatropha gossypiifolia.


Chemical Structure

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Jatrophone
CAS# 29444-03-9

Theoretical Analysis

MedKoo Cat#: 596170
Name: Jatrophone
CAS#: 29444-03-9
Chemical Formula: C20H24O3
Exact Mass: 312.1725
Molecular Weight: 312.4
Elemental Analysis: C, 76.89; H, 7.74; O, 15.36

Price and Availability

This product is not in stock, which may be available by custom synthesis. For cost-effective reason, minimum order is 1g (price is usually high, lead time is 2~3 months, depending on the technical challenge). Quote less than 1g will not be provided. To request quote, please email to sales @medkoo.com or click below button.
Note: Price will be listed if it is available in the future.

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Synonym: Jatrophone; Jatropha principle; NSC 135037; NSC-135037; NSC135037;

IUPAC/Chemical Name: (2R,3aR,9E,12Z)-2,5,8,8,12-pentamethyl-2,3,7,8-tetrahydro-3a,6-epoxycyclopenta[12]annulene-4,11-dione

InChi Key: MJNNONLDVCCGCA-ZQHAHMAHSA-N

InChi Code: InChI=1S/C20H24O3/c1-12-8-15-9-13(2)16(21)6-7-19(4,5)11-17-14(3)18(22)20(15,10-12)23-17/h6-9,12H,10-11H2,1-5H3/b7-6+,13-9-/t12-,20+/m0/s1

SMILES Code: O=C([C@]1(O2)C(/C=C3/C)=C[C@H](C)C1)C(C)=C2CC(C)(C)/C=C/C3=O

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

Preparing Stock Solutions

The following data is based on the product molecular weight 312.4 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

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1: Fatima I, El-Ayachi I, Taotao L, Angeles Lillo M, Krutilina RI, Seagroves TN, Radaszkiewicz TW, Hutnan M, Bryja V, Krum SA, Rivas F, Miranda-Carboni GA. Correction: The natural compound Jatrophone interferes with Wnt/β-catenin signaling and inhibits proliferation and EMT in human triple-negative breast cancer. PLoS One. 2018 May 17;13(5):e0197796. doi: 10.1371/journal.pone.0197796. eCollection 2018. PubMed PMID: 29771986.

2: Zolezzi JM, Lindsay CB, Serrano FG, Ureta RC, Theoduloz C, Schmeda-Hirschmann G, Inestrosa NC. Neuroprotective Effects of Ferruginol, Jatrophone, and Junicedric Acid Against Amyloid-β Injury in Hippocampal Neurons. J Alzheimers Dis. 2018;63(2):705-723. doi: 10.3233/JAD-170701. PubMed PMID: 29660932.

3: Fatima I, El-Ayachi I, Taotao L, Lillo MA, Krutilina R, Seagroves TN, Radaszkiewicz TW, Hutnan M, Bryja V, Krum SA, Rivas F, Miranda-Carboni GA. The natural compound Jatrophone interferes with Wnt/β-catenin signaling and inhibits proliferation and EMT in human triple-negative breast cancer. PLoS One. 2017 Dec 27;12(12):e0189864. doi: 10.1371/journal.pone.0189864. eCollection 2017. Erratum in: PLoS One. 2018 May 17;13(5):e0197796. PubMed PMID: 29281678; PubMed Central PMCID: PMC5744972.

4: Fröhlich JK, Stein T, da Silva LA, Biavatti MW, Tonussi CR, Lemos-Senna E. Antinociceptive and anti-inflammatory activities of the Jatropha isabellei dichloromethane fraction and isolation and quantitative determination of jatrophone by UFLC-DAD. Pharm Biol. 2017 Dec;55(1):1215-1222. doi: 10.1080/13880209.2017.1295999. PubMed PMID: 28249559.

5: Ovando-Medina I, Pérez-Díaz LP, Ruiz-González S, Salvador-Figueroa M, Urbina-Reyes ME, Adriano-Anaya L. Production of cytotoxic compounds in dedifferentiated cells of Jatropha curcas L. (Euphorbiaceae). PeerJ. 2016 Nov 1;4:e2616. eCollection 2016. PubMed PMID: 27833801; PubMed Central PMCID: PMC5101598.

6: Geng D, Yi LT, Shi Y, Min ZD. Structure and antibacterial property of a new diterpenoid from Euphorbia helioscopia. Chin J Nat Med. 2015 Sep;13(9):704-6. doi: 10.1016/S1875-5364(15)30069-8. PubMed PMID: 26412431.

7: Hadi V, Hotard M, Ling T, Salinas YG, Palacios G, Connelly M, Rivas F. Evaluation of Jatropha isabelli natural products and their synthetic analogs as potential antimalarial therapeutic agents. Eur J Med Chem. 2013 Jul;65:376-80. doi: 10.1016/j.ejmech.2013.04.030. Epub 2013 Apr 23. PubMed PMID: 23747806.

8: Theoduloz C, Rodríguez JA, Pertino M, Schmeda-Hirschmann G. Antiproliferative activity of the diterpenes jatrophone and jatropholone and their derivatives. Planta Med. 2009 Nov;75(14):1520-2. doi: 10.1055/s-0029-1185834. Epub 2009 Jun 26. PubMed PMID: 19562659.

9: Martini LH, Jung F, Soares FA, Rotta LN, Vendite DA, Frizzo ME, Yunes RA, Calixto JB, Wofchuk S, Souza DO. Naturally occurring compounds affect glutamatergic neurotransmission in rat brain. Neurochem Res. 2007 Nov;32(11):1950-6. Epub 2007 Jun 19. PubMed PMID: 17577666.

10: Pertino M, Schmeda-Hirschmann G, Rodríguez JA, Theoduloz C. Gastroprotective effect and cytotoxicity of terpenes from the Paraguayan crude drug "yagua rova" (Jatropha isabelli). J Ethnopharmacol. 2007 May 22;111(3):553-9. Epub 2007 Jan 7. PubMed PMID: 17276635.

11: Duarte N, Ferreira MJ. Lagaspholones A and B: two new jatropholane-type diterpenes from Euphorbia lagascae. Org Lett. 2007 Feb 1;9(3):489-92. PubMed PMID: 17249794.

12: Zhang W, Guo YW. Chemical studies on the constituents of the chinese medicinal herb Euphorbia helioscopia L. Chem Pharm Bull (Tokyo). 2006 Jul;54(7):1037-9. PubMed PMID: 16819227.

13: Brum RL, Cardoso CA, Honda NK, Andreu MP, Viana LL. Quantitative determination of jatrophone in "cachaça" prepared with Jatropha elliptica. Chem Pharm Bull (Tokyo). 2006 May;54(5):754-7. PubMed PMID: 16651786.

14: Zhang W, Guo YW. Three new jatrophone-type diterpenoids from Euphorbia helioscopia. Planta Med. 2005 Mar;71(3):283-6. PubMed PMID: 15770554.

15: Abdelgaleil SA, el-Aswad AF, Nakatani M. Molluscicidal and anti-feedant activities of diterpenes from Euphorbia paralias L. Pest Manag Sci. 2002 May;58(5):479-82. PubMed PMID: 11997975.

16: Moreira RR, Carlos IZ, Vilega W. Release of intermediate reactive hydrogen peroxide by macrophage cells activated by natural products. Biol Pharm Bull. 2001 Feb;24(2):201-4. PubMed PMID: 11217094.

17: Martini LH, Souza CR, Marques PB, Calixto JB, Yunes RA, Souza DO. Compounds extracted from Phyllantus and Jatropha elliptica inhibit the binding of [3H]glutamate and [3H]GMP-PNP in rat cerebral cortex membrane. Neurochem Res. 2000 Feb;25(2):211-5. PubMed PMID: 10786704.

18: dos Santos AF, Sant'Ana AE. Molluscicidal activity of the diterpenoids jatrophone and jatropholones A and B isolated from Jatropha elliptica (Pohl) Muell. Arg. Phytother Res. 1999 Dec;13(8):660-4. PubMed PMID: 10594934.

19: de Moraes VL, Rumjanek VM, Calixto JB. Jatrophone and 12-O-tetradecanoyl phorbol-13-acetate antagonism of stimulation of natural killer activity and lymphocyte proliferation. Eur J Pharmacol. 1996 Oct 3;312(3):333-9. PubMed PMID: 8894616.

20: Silva AM, Brum RL, Calixto JB. The relaxant action of jatrophone in rat portal vein. A comparison with protein kinase C inhibitors. Life Sci. 1995;57(9):863-71. PubMed PMID: 7630315.