Lychnopholide

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MedKoo CAT#: 530261

CAS#: 77448-64-7

Description: Lychnopholide is isolated from Vanillosmopsis erythropappa.


Price and Availability

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Pricing updated 2020-10-26. Prices are subject to change without notice.

Lychnopholide is not in stock, may be available through custom synthesis. For cost-effective reason, minimum 1 gram order is requested. The product will be characterized by NMR, HPLC and MS analysis. Purity (HPLC) is usually >98%. CoA, QC data, MSDS will be provided when product is successfully made. The estimated lead time is 2-3 months. Please send email to sales@medkoo.com to inquire quote.


Chemical Structure

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Theoretical Analysis

MedKoo Cat#: 530261
Name: Lychnopholide
CAS#: 77448-64-7
Chemical Formula: C20H22O6
Exact Mass: 358.1416
Molecular Weight: 358.39
Elemental Analysis: C, 67.03; H, 6.19; O, 26.78


Synonym: Lychnopholide

IUPAC/Chemical Name: 2-Butenoic acid, 2-methyl-, 2,3,3a,4,5,6,7,11a-octahydro-6,10-dimethyl-3-methylene-2,7-dioxo-6,9-epoxycyclodeca(b)furan-4-yl ester, (3aR-(3aR*,4S*(Z),6R*,10Z,11aR*))-

InChi Key: QATUWZPYBIHFFR-AWCNYIIHSA-N

InChi Code: InChI=1S/C20H22O6/c1-6-10(2)18(22)25-15-9-20(5)16(21)8-13(26-20)11(3)7-14-17(15)12(4)19(23)24-14/h6-8,14-15,17H,4,9H2,1-3,5H3/b10-6+,11-7-/t14-,15+,17+,20-/m1/s1

SMILES Code: C/C=C(C)/C(O[C@H]([C@](C1=C)([H])[C@]2([H])OC1=O)C[C@](O3)(C)C(C=C3/C(C)=C\2)=O)=O


Technical Data

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:
2934.99.03.00


References

1: Tupinambá Branquinho R, Pound-Lana G, Marques Milagre M, Saúde-Guimarães DA, Vilela JMC, Spangler Andrade M, de Lana M, Mosqueira VCF. Increased Body Exposure to New Anti-Trypanosomal Through Nanoencapsulation. Sci Rep. 2017 Aug 16;7(1):8429. doi: 10.1038/s41598-017-08469-x. PubMed PMID: 28814794; PubMed Central PMCID: PMC5559493.

2: Branquinho RT, Roy J, Farah C, Garcia GM, Aimond F, Le Guennec JY, Saude-Guimarães DA, Grabe-Guimaraes A, Mosqueira VC, de Lana M, Richard S. Biodegradable Polymeric Nanocapsules Prevent Cardiotoxicity of Anti-Trypanosomal Lychnopholide. Sci Rep. 2017 Mar 28;7:44998. doi: 10.1038/srep44998. PubMed PMID: 28349937; PubMed Central PMCID: PMC5368638.

3: de Mello CG, Branquinho RT, Oliveira MT, Milagre MM, Saúde-Guimarães DA, Mosqueira VC, Lana Md. Efficacy of Lychnopholide Polymeric Nanocapsules after Oral and Intravenous Administration in Murine Experimental Chagas Disease. Antimicrob Agents Chemother. 2016 Aug 22;60(9):5215-22. doi: 10.1128/AAC.00178-16. Print 2016 Sep. PubMed PMID: 27324760; PubMed Central PMCID: PMC4997880.

4: Lachi-Silva L, Sousa JPB, Montanha MC, Sy SKB, Lopes JLC, Silva DB, Lopes NP, Diniz A, Kimura E. Rapid and efficient method for the quantification of lychnopholide in rat plasma by liquid chromatography-tandem mass spectrometry for pharmacokinetic application. Biomed Chromatogr. 2016 Jul;30(7):1092-1096. doi: 10.1002/bmc.3654. Epub 2016 Jan 3. PubMed PMID: 26577838.

5: Lachi-Silva L, Sy SK, Voelkner A, de Sousa JP, Lopes JL, Silva DB, Lopes NP, Kimura E, Derendorf H, Diniz A. Simultaneous Characterization of Intravenous and Oral Pharmacokinetics of Lychnopholide in Rats by Transit Compartment Model. Planta Med. 2015 Aug;81(12-13):1121-7. doi: 10.1055/s-0035-1546214. Epub 2015 Jul 28. PubMed PMID: 26218336.

6: Morilla MJ, Romero EL. Nanomedicines against Chagas disease: an update on therapeutics, prophylaxis and diagnosis. Nanomedicine (Lond). 2015 Feb;10(3):465-81. doi: 10.2217/nnm.14.185. Review. PubMed PMID: 25707979.

7: Branquinho RT, Mosqueira VC, de Oliveira-Silva JC, Simões-Silva MR, Saúde-Guimarães DA, de Lana M. Sesquiterpene lactone in nanostructured parenteral dosage form is efficacious in experimental Chagas disease. Antimicrob Agents Chemother. 2014;58(4):2067-75. doi: 10.1128/AAC.00617-13. Epub 2014 Jan 21. PubMed PMID: 24449777; PubMed Central PMCID: PMC4023798.

8: Branquinho RT, Mosqueira VC, Kano EK, de Souza J, Dorim DD, Saúde-Guimarães DA, de Lana M. HPLC-DAD and UV-spectrophotometry for the determination of lychnopholide in nanocapsule dosage form: validation and application to release kinetic study. J Chromatogr Sci. 2014 Jan;52(1):19-26. doi: 10.1093/chromsci/bms199. Epub 2012 Dec 17. PubMed PMID: 23247030.

9: de Souza MR, de Paula CA, Pereira de Resende ML, Grabe-Guimarães A, de Souza Filho JD, Saúde-Guimarães DA. Pharmacological basis for use of Lychnophora trichocarpha in gouty arthritis: anti-hyperuricemic and anti-inflammatory effects of its extract, fraction and constituents. J Ethnopharmacol. 2012 Aug 1;142(3):845-50. doi: 10.1016/j.jep.2012.06.012. Epub 2012 Jun 23. PubMed PMID: 22732730.

10: Ferrari FC, Ferreira LC, Souza MR, Grabe-Guimarães A, Paula CA, Rezende SA, Saúde-Guimarães DA. Anti-inflammatory sesquiterpene lactones from Lychnophora trichocarpha Spreng. (Brazilian Arnica). Phytother Res. 2013 Mar;27(3):384-9. doi: 10.1002/ptr.4736. Epub 2012 May 23. PubMed PMID: 22619042.

11: Kanashiro A, Kabeya LM, Grael CF, Jordão CO, Azzolini AE, Lopes JL, Lucisano-Valim YM. Sesquiterpene lactones from Lychnophora pohlii: neutrophil chemiluminescence inhibition and free radical scavenger activity. J Pharm Pharmacol. 2006 Jun;58(6):853-8. PubMed PMID: 16734987.

12: Grael CF, Albuquerque S, Lopes JL. Chemical constituents of Lychnophora pohlii and trypanocidal activity of crude plant extracts and of isolated compounds. Fitoterapia. 2005 Jan;76(1):73-82. PubMed PMID: 15664466.

13: Barrero AF, Oltra JE, Alvarez M, Raslan DS, Saúde DA, Akssira M. New sources and antifungal activity of sesquiterpene lactones. Fitoterapia. 2000 Feb;71(1):60-4. PubMed PMID: 11449472.

14: Canalle R, Burim RV, Callegari Lopes JL, Takahashi CS. Assessment of the cytotoxic and clastogenic activities of the sesquiterpene lactone lynchnopholide in mammalian cells in vitro and in vivo. Cancer Detect Prev. 2001;25(1):93-101. PubMed PMID: 11270427.

15: Barrero AF, Oltra JE, Raslan DS, Saude DA. Microbial transformation of sesquiterpene lactones by the fungi cunninghamella echinulata and rhizopus oryzae . J Nat Prod. 1999 May;62(5):726-9. PubMed PMID: 10346955.