Isomitraphylline

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

MedKoo CAT#: 592324

CAS#: 4963-01-3

Description: Isomitraphylline is a biochemical.


Chemical Structure

img
Isomitraphylline
CAS# 4963-01-3

Theoretical Analysis

MedKoo Cat#: 592324
Name: Isomitraphylline
CAS#: 4963-01-3
Chemical Formula: C21H24N2O4
Exact Mass: 368.17
Molecular Weight: 368.430
Elemental Analysis: C, 68.46; H, 6.57; N, 7.60; O, 17.37

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.

Request quote for custom synthesis

Synonym: Isomitraphylline; Ajmalicine oxindole A

IUPAC/Chemical Name: Formosanan-16-carboxylic acid, 19-methyl-2-oxo-, methyl ester, (7alpha,19alpha)-

InChi Key: JMIAZDVHNCCPDM-NWQITLLVSA-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: COC(C1=CO[C@H]([C@H]2CN3CC[C@@]4(C(Nc5c4cccc5)=O)[C@@H]3C[C@H]12)C)=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: >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

More Info:

Biological target:
In vitro activity:
In vivo activity:

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:
In vitro protocol:
In vivo protocol:

Molarity Calculator

Calculate the mass, volume, or concentration required for a solution.
=
x
x
g/mol

*When preparing stock solutions always use the batch-specific molecular weight of the product found on the vial label and SDS / CoA (available online).

Reconstitution Calculator

The reconstitution calculator allows you to quickly calculate the volume of a reagent to reconstitute your vial. Simply enter the mass of reagent and the target concentration and the calculator will determine the rest.

=
÷

Dilution Calculator

Calculate the dilution required to prepare a stock solution.
x
=
x

1: Alvarenga-Venutolo S, Rosales-López C, Sánchez-Chinchilla L, Muñoz-Arrieta R, Aguilar-Cascante F. Seasonality effect on the composition of oxindole alkaloids from distinct organs of Uncaria tomentosa from the Caribbean region of Costa Rica. Phytochemistry. 2018 Jul;151:26-31. doi: 10.1016/j.phytochem.2018.03.008. Epub 2018 Apr 6. PubMed PMID: 29631104.

2: 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.

3: 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.

4: Chang CW, Yeh YY, Chang LC, Hsu MC, Wu YT. Rapid determination of oxindole alkaloids in cat's claw by HPLC using ionic liquid-based microwave-assisted extraction and silica monolithic column. Biomed Chromatogr. 2017 Aug;31(8). doi: 10.1002/bmc.3925. Epub 2017 Jan 24. PubMed PMID: 28009448.

5: 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.

6: Sánchez-Rojo S, Cerda-García-Rojas CM, Esparza-García F, Plasencia J, Poggi-Varaldo HM, Ponce-Noyola T, Ramos-Valdivia AC. Long-term response on growth, antioxidant enzymes, and secondary metabolites in salicylic acid pre-treated Uncaria tomentosa microplants. Biotechnol Lett. 2015 Dec;37(12):2489-96. doi: 10.1007/s10529-015-1931-0. Epub 2015 Aug 14. PubMed PMID: 26272395.

7: 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.

8: Luna-Palencia GR, Huerta-Heredia AA, Cerda-García-Rojas CM, Ramos-Valdivia AC. Differential alkaloid profile in Uncaria tomentosa micropropagated plantlets and root cultures. Biotechnol Lett. 2013 May;35(5):791-7. doi: 10.1007/s10529-012-1128-8. Epub 2013 Jan 8. PubMed PMID: 23296316.

9: Shukla A, Srinivasan BP. 16,17-Dihydro-17b-hydroxy isomitraphylline alkaloid as an inhibitor of DPP-IV, and its effect on incretin hormone and β-cell proliferation in diabetic rat. Eur J Pharm Sci. 2012 Sep 29;47(2):512-9. doi: 10.1016/j.ejps.2012.07.012. Epub 2012 Jul 20. PubMed PMID: 22820565.

10: León F, Habib E, Adkins JE, Furr EB, McCurdy CR, Cutler SJ. Phytochemical characterization of the leaves of Mitragyna speciosa grown in U.S.A. Nat Prod Commun. 2009 Jul;4(7):907-10. PubMed PMID: 19731590.

11: 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.

12: Xin WB, Gu P, Chou GX, Wang ZT. [Studies on alkalodial constituents in leaves of Uncaria hirsuta]. Zhongguo Zhong Yao Za Zhi. 2008 Sep;33(17):2124-8. Chinese. PubMed PMID: 19066056.

13: Paradowska K, Wolniak M, Pisklak M, Gliński JA, Davey MH, Wawer I. (13)C, (15)N CPMAS NMR and GIAO DFT calculations of stereoisomeric oxindole alkaloids from Cat's Claw (Uncaria tomentosa). Solid State Nucl Magn Reson. 2008 Nov;34(4):202-9. doi: 10.1016/j.ssnmr.2008.10.002. Epub 2008 Oct 22. PubMed PMID: 19019638.

14: Pilarski R, Poczekaj-Kostrzewska M, Ciesiołka D, Szyfter K, Gulewicz K. Antiproliferative activity of various Uncaria tomentosa preparations on HL-60 promyelocytic leukemia cells. Pharmacol Rep. 2007 Sep-Oct;59(5):565-72. PubMed PMID: 18048957.

15: 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.

16: 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.