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Isomitraphylline

CAS# 4963-01-3

Isomitraphylline

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Chemical structure

Isomitraphylline

3D structure

Chemical Properties of Isomitraphylline

Cas No. 4963-01-3 SDF Download SDF
PubChem ID 11726520 Appearance White powder
Formula C21H24N2O4 M.Wt 368.42
Type of Compound Alkaloids Storage Desiccate at -20°C
Synonyms Ajmalicine oxindole A
Solubility Soluble in chloroform, diethyl ether and methanol; sparingly soluble in water
Chemical Name methyl (1S,4aS,5aS,6S,10aR)-1-methyl-2'-oxospiro[1,4a,5,5a,7,8,10,10a-octahydropyrano[3,4-f]indolizine-6,3'-1H-indole]-4-carboxylate
SMILES CC1C2CN3CCC4(C3CC2C(=CO1)C(=O)OC)C5=CC=CC=C5NC4=O
Standard InChIKey JMIAZDVHNCCPDM-NWQITLLVSA-N
Standard InChI 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
General tips For obtaining a higher solubility , please warm the tube at 37 ℃ and shake it in the ultrasonic bath for a while.Stock solution can be stored below -20℃ for several months.
We recommend that you prepare and use the solution on the same day. However, if the test schedule requires, the stock solutions can be prepared in advance, and the stock solution must be sealed and stored below -20℃. In general, the stock solution can be kept for several months.
Before use, we recommend that you leave the vial at room temperature for at least an hour before opening it.
About Packaging 1. The packaging of the product may be reversed during transportation, cause the high purity compounds to adhere to the neck or cap of the vial.Take the vail out of its packaging and shake gently until the compounds fall to the bottom of the vial.
2. For liquid products, please centrifuge at 500xg to gather the liquid to the bottom of the vial.
3. Try to avoid loss or contamination during the experiment.
Shipping Condition Packaging according to customer requirements(5mg, 10mg, 20mg and more). Ship via FedEx, DHL, UPS, EMS or other couriers with RT, or blue ice upon request.

Source of Isomitraphylline

The leaves of Mitragyna speciosa.

Biological Activity of Isomitraphylline

Description1. Isomitraphylline and pteropodine are the most suitable for standardization of medical cat's claw preparations. 2. Isomitraphylline can inhibit proliferation of acute lymphoblastic leukaemia cells.
TargetsBcl-2/Bax

Isomitraphylline Dilution Calculator

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Isomitraphylline Molarity Calculator

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Preparing Stock Solutions of Isomitraphylline

1 mg 5 mg 10 mg 20 mg 25 mg
1 mM 2.7143 mL 13.5715 mL 27.1429 mL 54.2859 mL 67.8573 mL
5 mM 0.5429 mL 2.7143 mL 5.4286 mL 10.8572 mL 13.5715 mL
10 mM 0.2714 mL 1.3571 mL 2.7143 mL 5.4286 mL 6.7857 mL
50 mM 0.0543 mL 0.2714 mL 0.5429 mL 1.0857 mL 1.3571 mL
100 mM 0.0271 mL 0.1357 mL 0.2714 mL 0.5429 mL 0.6786 mL
* Note: If you are in the process of experiment, it's necessary to make the dilution ratios of the samples. The dilution data above is only for reference. Normally, it's can get a better solubility within lower of Concentrations.

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References on Isomitraphylline

Long-term response on growth, antioxidant enzymes, and secondary metabolites in salicylic acid pre-treated Uncaria tomentosa microplants.[Pubmed:26272395]

Biotechnol Lett. 2015 Dec;37(12):2489-96.

OBJECTIVE: To obtain micro propagated Uncaria tomentosa plantlets with enhanced secondary metabolites production, long-term responses to salicylic acid (SA) pre-treatments at 1 and 100 microM were evaluated after propagation of the plantlets in a SA-free medium. RESULTS: SA pre-treatments of single node cuttings OF U. tomentosa produced long-term responses in microplants grown for 75 days in a SA-free medium. Reduction in survival rate, root formation, and stem elongation were observed only with 100 microM SA pre-treatments with respect to the control (0 + DMSO).Both pre-treatments enhanced H2O2 and inhibited superoxide dismutase and catalase activities, while guaiacol peroxidase was increased only with 1 microM SA. Also, both pre-treatments increased total monoterpenoid oxindole alkaloids by ca. 55 % (16.5 mg g(-1) DW), including isopteropodine, speciophylline, mitraphylline, Isomitraphylline, rhynchopylline, and isorhynchopylline; and flavonoids by ca. 21 % (914 mug g(-1) DW), whereas phenolic compounds were increased 80 % (599 mug g(-1) DW) at 1 microM and 8.2 % (359 mug g(-1) DW) at 100 microM SA. CONCLUSION: Pre-treatment with 1 microM SA of U.tomentosa microplants preserved the survival rate and increased oxindole alkaloids, flavonoids, and phenolic compounds in correlation with H2O2 and peroxidase activity enhancements, offering biotechnological advantages over non-treated microplants.

Oxindole alkaloids from Uncaria tomentosa induce apoptosis in proliferating, G0/G1-arrested and bcl-2-expressing acute lymphoblastic leukaemia cells.[Pubmed:16445836]

Br J Haematol. 2006 Mar;132(5):615-22.

Natural products are still an untapped source of promising lead compounds for the generation of antineoplastic drugs. Here, we investigated for the first time the antiproliferative and apoptotic effects of highly purified oxindole alkaloids, namely isopteropodine (A1), pteropodine (A2), Isomitraphylline (A3), uncarine F (A4) and mitraphylline (A5) obtained from Uncaria tomentosa, a South American Rubiaceae, on human lymphoblastic leukaemia T cells (CCRF-CEM-C7H2). Four of the five tested alkaloids inhibited proliferation of acute lymphoblastic leukaemia cells. Furthermore, the antiproliferative effect of the most potent alkaloids pteropodine (A2) and uncarine F (A4) correlated with induction of apoptosis. After 48 h, 100 micromol/l A2 or A4 increased apoptotic cells by 57%. CEM-C7H2 sublines with tetracycline-regulated expression of bcl-2, p16ink4A or constitutively expressing the cowpox virus protein crm-A were used for further studies of the apoptosis-inducing properties of these alkaloids. Neither overexpression of bcl-2 or crm-A nor cell-cycle arrest in G0/G1 phase by tetracycline-regulated expression of p16INK4A could prevent alkaloid-induced apoptosis. Our results show the strong apoptotic effects of pteropodine and uncarine F on acute leukaemic lymphoblasts and recommend the alkaloids for further studies in xenograft models.

Phytochemical characterization of the leaves of Mitragyna speciosa grown in U.S.A.[Pubmed:19731590]

Nat Prod Commun. 2009 Jul;4(7):907-10.

Mitragyna speciosa (Rubiaceae) has traditionally been used in the tropical regions of Asia, Africa and Indonesia as a substitute for opium. Indole alkaloids are the most common compounds that have been isolated. We investigated the constituents of the leaves of M. speciosa that was grown at the University of Mississippi. Several alkaloids were isolated, including ajmalicine, corynantheidine, Isomitraphylline, mitraphylline, paynantheine, isocorynantheidine, 7-hydroxymitragynine and mitragynine, but their percentages were lower than those in a commercial Thai sample of "kratom". In addition, we isolated the flavonoid epicatechin, a saponin daucosterol, the triterpenoid saponins quinovic acid 3-O-beta-D-quinovopyranoside, quinovic acid 3-O-beta-D-glucopyranoside, as well as several glycoside derivatives including 1-O-feruloyl-beta-D-glucopyranoside, benzyl-beta-D-glucopyranoside, 3-oxo-alpha-ionyl-O-beta-D-glucopyranoside, roseoside, vogeloside, and epivogeloside. This is the first report of the last group of compounds having been isolated from a Mitragyna species. Biological studies are currently underway to test these compounds for opioid activity.

Antiproliferative activity of various Uncaria tomentosa preparations on HL-60 promyelocytic leukemia cells.[Pubmed:18048957]

Pharmacol Rep. 2007 Sep-Oct;59(5):565-72.

The woody Amazonian vine Uncaria tomentosa (cat's claw) has been recently more and more popular all over the world as an immunomodulatory, antiinflammatory and anti-cancer remedy. This study investigates anti-proliferative potency of several cat's claw preparations with different quantitative and qualitative alkaloid contents on HL-60 acute promyelocytic human cells by applying trypan blue exclusion and 3-(4,5-dimethylthiazol-2-yl)-2,5-diphenyltetrazolium bromide reduction assay (MTT). By standardization and statistical comparison of the obtained results pteropodine and Isomitraphylline are indicated to be most suitable for standardization of medical cat's claw preparations.

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