ISOMITRAPHYLLINE Chemical Properties

Boiling point:

555.2±50.0 °C(Predicted)

Density 

1.33±0.1 g/cm3(Predicted)

storage temp. 

-20°C

solubility 

Acetonitrile: Slightly soluble: 0.1-1 mg/ml
Chloroform: Sparingly soluble: 1-10 mg/ml

pka

13.56±0.60(Predicted)

ISOMITRAPHYLLINE Usage And Synthesis

Description

This Mitragyna alkaloid has been isolated from the leaves of M. speciosa Korth by Beckett and his colleagues. It is an amorphous solid which cannot be obtained crystalline. The base may be characterized as the picrate which forms pale yellow needles from MeOH, m.p. 223°C (dec.). A methylgroup, a methoxycarbonyl group and one imino group are present. The second nitrogen atom is tertiary.

Uses

Isomitraphylline is an oxoindole alkaloid derivied from amazonian plants and maintain medicinal benefits. Used in the treatment of ulcers, arthritis, etc.

Biological Activity

Isomitraphylline, an oxindole alkaloid, has potent anti-cancer activity.

References

[1] Beckett et al., J. Pharm. Pharmacol., 17,753 (1965)
[2] Beckett et ai., Planta Med., 14, 266 (1966)
[3] Structure:
[4] Finch, Taylor., J. Amer. Chem. Soc., 84,3871 (1962)
[5] Prepara tion:
[6] Seaton et al., Can. J. Chem., 38, 1035 (1960)
[7] [1] L DINAN. Assessment of natural products in the Drosophila melanogaster B(II) cell bioassay for ecdysteroid agonist and antagonist activities.[J]. Psychological Reports, 2001, 8 1: 321-342. DOI: 10.1007/pl00000859

[8] [2] NICOLE BACHER. Oxindole alkaloids from Uncaria tomentosa induce apoptosis in proliferating, G0/G1-arrested and bcl-2-expressing acute lymphoblastic leukaemia cells[J]. British Journal of Haematology, 2006, 132 5: 615-622. DOI: 10.1111/j.1365-2141.2005.05907.x

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