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MedKoo Cat#: 584793 | Name: Mitraphylline
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Description:

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

Mitraphylline is isolated from Uncaria tomentosa and has potential anti-inflammatory activity.

Chemical Structure

Mitraphylline
Mitraphylline
CAS#509-80-8

Theoretical Analysis

MedKoo Cat#: 584793

Name: Mitraphylline

CAS#: 509-80-8

Chemical Formula: C21H24N2O4

Exact Mass: 368.1736

Molecular Weight: 368.43

Elemental Analysis: C, 68.46; H, 6.57; N, 7.60; O, 17.37

Price and Availability

Size Price Availability Quantity
5mg USD 400.00 2 weeks
10mg USD 750.00 2 weeks
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Related CAS #
No Data
Synonym
Mitraphylline; Mitraphilline
IUPAC/Chemical Name
Methyl 19alpha-methyl-2-oxoformosanan-16-carboxylate
InChi Key
JMIAZDVHNCCPDM-DAFCLMLCSA-N
InChi Code
InChI=1S/C21H24N2O4/c1-12-14-10-23-8-7-21(16-5-3-4-6-17(16)22-20(21)25)18(23)9-13(14)15(11-27-12)19(24)26-2/h3-6,11-14,18H,7-10H2,1-2H3,(H,22,25)/t12-,13-,14+,18-,21+/m0/s1
SMILES Code
O=C(C1=CO[C@@H](C)[C@@]([C@]1([H])C[C@]23[H])([H])CN2CC[C@@]43C(NC5=C4C=CC=C5)=O)OC
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
Product Data
Product Data
Instruction
View handling instruction
Biological target:
Mitraphylline inhibits lipopolysaccharide-mediated activation of primary human neutrophils.
In vitro activity:
Treatment with MTP (mitraphylline) reduced the LPS-dependent activation effects. Activated neutrophils (CD16(+)CD62L(-)) diminished after MTP administration. Moreover, proinflamatory cytokines (TNF-α, IL-6 or IL-8) expression and secretion were concomitantly reduced, similar to basal control conditions. Reference: Phytomedicine. 2016 Feb 15;23(2):141-8. https://pubmed.ncbi.nlm.nih.gov/26926175/
In vivo activity:
Mice received mitraphylline once a day for 3 days at 30 mg/kg/day by oral route. Then, they were subjected to bacterial lipopolysaccharide (LPS) endotoxin (15 mg/kg) and the LPS-induced production of 16 different cytokines was determined by Elisa multiplex. Control group received dexamethasone orally at 2mg/kg/day. Toxicity on K565 cells and murine peritoneal macrophages, in vitro, at doses up to 100 μM was monitored by XTT-colorimetric assay.For the first time mitraphylline was tested in vivo against a large range of cytokines that play a crucial role in inflammation. Mitraphylline inhibited around 50% of the release of interleukins 1α, 1β, 17, and TNF-α. Reference: J Ethnopharmacol. 2012 Oct 11;143(3):801-4. https://pubmed.ncbi.nlm.nih.gov/22846434/
Solvent mg/mL mM comments
Solubility
DMF 5.0 13.57
DMSO 5.9 15.96
DMSO:PBS (pH 7.2) (1:2) 0.3 0.90
Note: There can be variations in solubility for the same chemical from different vendors or different batches from the same vendor. The following factors can affect the solubility of the same chemical: solvent used for crystallization, residual solvent content, polymorphism, salt versus free form, degree of hydration, solvent temperature. Please use the solubility data as a reference only. Warming and sonication will facilitate dissolving. Still have questions? Please contact our Technical Support scientists.

Preparing Stock Solutions

The following data is based on the product molecular weight 368.43 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
Formulation protocol:
1. Montserrat-de la Paz S, Fernandez-Arche A, de la Puerta R, Quilez AM, Muriana FJ, Garcia-Gimenez MD, Bermudez B. Mitraphylline inhibits lipopolysaccharide-mediated activation of primary human neutrophils. Phytomedicine. 2016 Feb 15;23(2):141-8. doi: 10.1016/j.phymed.2015.12.015. Epub 2016 Jan 14. PMID: 26926175. 2. García Giménez D, García Prado E, Sáenz Rodríguez T, Fernández Arche A, De la Puerta R. Cytotoxic effect of the pentacyclic oxindole alkaloid mitraphylline isolated from Uncaria tomentosa bark on human Ewing's sarcoma and breast cancer cell lines. Planta Med. 2010 Feb;76(2):133-6. doi: 10.1055/s-0029-1186048. Epub 2009 Sep 1. PMID: 19724995. 3. Rojas-Duran R, González-Aspajo G, Ruiz-Martel C, Bourdy G, Doroteo-Ortega VH, Alban-Castillo J, Robert G, Auberger P, Deharo E. Anti-inflammatory activity of Mitraphylline isolated from Uncaria tomentosa bark. J Ethnopharmacol. 2012 Oct 11;143(3):801-4. doi: 10.1016/j.jep.2012.07.015. Epub 2012 Jul 27. PMID: 22846434.
In vitro protocol:
1. Montserrat-de la Paz S, Fernandez-Arche A, de la Puerta R, Quilez AM, Muriana FJ, Garcia-Gimenez MD, Bermudez B. Mitraphylline inhibits lipopolysaccharide-mediated activation of primary human neutrophils. Phytomedicine. 2016 Feb 15;23(2):141-8. doi: 10.1016/j.phymed.2015.12.015. Epub 2016 Jan 14. PMID: 26926175. 2. García Giménez D, García Prado E, Sáenz Rodríguez T, Fernández Arche A, De la Puerta R. Cytotoxic effect of the pentacyclic oxindole alkaloid mitraphylline isolated from Uncaria tomentosa bark on human Ewing's sarcoma and breast cancer cell lines. Planta Med. 2010 Feb;76(2):133-6. doi: 10.1055/s-0029-1186048. Epub 2009 Sep 1. PMID: 19724995.
In vivo protocol:
1. Rojas-Duran R, González-Aspajo G, Ruiz-Martel C, Bourdy G, Doroteo-Ortega VH, Alban-Castillo J, Robert G, Auberger P, Deharo E. Anti-inflammatory activity of Mitraphylline isolated from Uncaria tomentosa bark. J Ethnopharmacol. 2012 Oct 11;143(3):801-4. doi: 10.1016/j.jep.2012.07.015. Epub 2012 Jul 27. PMID: 22846434.
1: Montserrat-de la Paz S, Fernandez-Arche A, de la Puerta R, Quilez AM, Muriana FJ, Garcia-Gimenez MD, Bermudez B. Mitraphylline inhibits lipopolysaccharide-mediated activation of primary human neutrophils. Phytomedicine. 2016 Feb 15;23(2):141-8. doi: 10.1016/j.phymed.2015.12.015. Epub 2016 Jan 14. PubMed PMID: 26926175. 2: Manda VK, Avula B, Ali Z, Khan IA, Walker LA, Khan SI. Evaluation of in vitro absorption, distribution, metabolism, and excretion (ADME) properties of mitragynine, 7-hydroxymitragynine, and mitraphylline. Planta Med. 2014 May;80(7):568-76. doi: 10.1055/s-0034-1368444. Epub 2014 May 19. PubMed PMID: 24841968. 3: Montserrat-de la Paz S, de la Puerta R, Fernandez-Arche A, Quilez AM, Muriana FJ, Garcia-Gimenez MD, Bermudez B. Pharmacological effects of mitraphylline from Uncaria tomentosa in primary human monocytes: Skew toward M2 macrophages. J Ethnopharmacol. 2015 Jul 21;170:128-35. doi: 10.1016/j.jep.2015.05.002. Epub 2015 May 11. PubMed PMID: 25975515. 4: García Prado E, García Gimenez MD, De la Puerta Vázquez R, Espartero Sánchez JL, Sáenz Rodríguez MT. Antiproliferative effects of mitraphylline, a pentacyclic oxindole alkaloid of Uncaria tomentosa on human glioma and neuroblastoma cell lines. Phytomedicine. 2007 Apr;14(4):280-4. Epub 2007 Feb 12. PubMed PMID: 17296291. 5: Rojas-Duran R, González-Aspajo G, Ruiz-Martel C, Bourdy G, Doroteo-Ortega VH, Alban-Castillo J, Robert G, Auberger P, Deharo E. Anti-inflammatory activity of Mitraphylline isolated from Uncaria tomentosa bark. J Ethnopharmacol. 2012 Oct 11;143(3):801-4. doi: 10.1016/j.jep.2012.07.015. Epub 2012 Jul 27. PubMed PMID: 22846434. 6: García Giménez D, García Prado E, Sáenz Rodríguez T, Fernández Arche A, De la Puerta R. Cytotoxic effect of the pentacyclic oxindole alkaloid mitraphylline isolated from Uncaria tomentosa bark on human Ewing's sarcoma and breast cancer cell lines. Planta Med. 2010 Feb;76(2):133-6. doi: 10.1055/s-0029-1186048. Epub 2009 Sep 1. PubMed PMID: 19724995. 7: Matsunaga T, Morikawa Y, Kamase K, Horinouchi M, Sasajima Y, Suenami K, Sato K, Takekoshi Y, Endo S, El-Kabbani O, Ikari A. Enhancement of Endothelial Barrier Permeability by Mitragynine. Biol Pharm Bull. 2017;40(10):1779-1783. doi: 10.1248/bpb.b17-00117. PubMed PMID: 28966251. 8: Honório ICG, Bertoni BW, Telles MPC, Braga RDS, França SC, Coppede JDS, Correa VSC, Diniz Filho JAF, Pereira AMS. Genetic and chemical diversity of Uncaria tomentosa (Willd. ex. Schult.) DC. in the Brazilian Amazon. PLoS One. 2017 May 5;12(5):e0177103. doi: 10.1371/journal.pone.0177103. eCollection 2017. PubMed PMID: 28475604; PubMed Central PMCID: PMC5419575. 9: Azevedo BC, Morel LJF, Carmona F, Cunha TM, Contini SHT, Delprete PG, Ramalho FS, Crevelin E, Bertoni BW, França SC, Borges MC, Pereira AMS. Aqueous extracts from Uncaria tomentosa (Willd. ex Schult.) DC. reduce bronchial hyperresponsiveness and inflammation in a murine model of asthma. J Ethnopharmacol. 2018 May 23;218:76-89. doi: 10.1016/j.jep.2018.02.013. Epub 2018 Feb 10. PubMed PMID: 29432856. 10: Pandey R, Singh SC, Gupta MM. Heteroyohimbinoid type oxindole alkaloids from Mitragyna parvifolia. Phytochemistry. 2006 Oct;67(19):2164-9. Epub 2006 Jul 26. PubMed PMID: 16872649. 11: NOZOYE T. Studies on uncaria alkaloid. XIX. On mitraphylline. Chem Pharm Bull (Tokyo). 1958 Jun;6(3):306-8. PubMed PMID: 13573490. 12: Bertol G, Franco L, Oliveira BH. HPLC analysis of oxindole alkaloids in Uncaria tomentosa: sample preparation and analysis optimisation by factorial design. Phytochem Anal. 2012 Mar-Apr;23(2):143-51. doi: 10.1002/pca.1335. Epub 2011 Aug 2. PubMed PMID: 21809407. 13: Le D, Goggin MM, Janis GC. Analysis of mitragynine and metabolites in human urine for detecting the use of the psychoactive plant kratom. J Anal Toxicol. 2012 Nov-Dec;36(9):616-25. doi: 10.1093/jat/bks073. Epub 2012 Sep 28. PubMed PMID: 23024321. 14: Zhang Q, Zhao JJ, Xu J, Feng F, Qu W. Medicinal uses, phytochemistry and pharmacology of the genus Uncaria. J Ethnopharmacol. 2015 Sep 15;173:48-80. doi: 10.1016/j.jep.2015.06.011. Epub 2015 Jun 17. Review. PubMed PMID: 26091967. 15: Bacher N, Tiefenthaler M, Sturm S, Stuppner H, Ausserlechner MJ, Kofler R, Konwalinka G. Oxindole alkaloids from Uncaria tomentosa induce apoptosis in proliferating, G0/G1-arrested and bcl-2-expressing acute lymphoblastic leukaemia cells. Br J Haematol. 2006 Mar;132(5):615-22. PubMed PMID: 16445836. 16: Lesiak AD, Cody RB, Dane AJ, Musah RA. Rapid detection by direct analysis in real time-mass spectrometry (DART-MS) of psychoactive plant drugs of abuse: the case of Mitragyna speciosa aka "Kratom". Forensic Sci Int. 2014 Sep;242:210-218. doi: 10.1016/j.forsciint.2014.07.005. Epub 2014 Jul 14. PubMed PMID: 25086346. 17: Mohamed AF, Matsumoto K, Tabata K, Takayama H, Kitajima M, Watanabe H. Effects of Uncaria tomentosa total alkaloid and its components on experimental amnesia in mice: elucidation using the passive avoidance test. J Pharm Pharmacol. 2000 Dec;52(12):1553-61. PubMed PMID: 11197086. 18: Honório ICG, Coppede JS, Delprete PG, Costa FHS, Telles MPC, Braga RS, Diniz-Filho JAF, Correa VSC, França SC, Pereira AMS, Bertoni BW. Genetic structure and chemical diversity in natural populations of Uncaria guianensis (Aubl.) J.F.Gmel. (Rubiaceae). PLoS One. 2018 Oct 26;13(10):e0205667. doi: 10.1371/journal.pone.0205667. eCollection 2018. PubMed PMID: 30365495; PubMed Central PMCID: PMC6203251. 19: Nakabayashi R, Tsugawa H, Kitajima M, Takayama H, Saito K. Boosting Sensitivity in Liquid Chromatography-Fourier Transform Ion Cyclotron Resonance-Tandem Mass Spectrometry for Product Ion Analysis of Monoterpene Indole Alkaloids. Front Plant Sci. 2015 Dec 17;6:1127. doi: 10.3389/fpls.2015.01127. eCollection 2015. PubMed PMID: 26734034; PubMed Central PMCID: PMC4681812. 20: Kaiser S, Carvalho ÂR, Pittol V, Dietrich F, Manica F, Machado MM, de Oliveira LF, Oliveira Battastini AM, Ortega GG. Genotoxicity and cytotoxicity of oxindole alkaloids from Uncaria tomentosa (cat's claw): Chemotype relevance. J Ethnopharmacol. 2016 Aug 2;189:90-8. doi: 10.1016/j.jep.2016.05.026. Epub 2016 May 13. PubMed PMID: 27180878.