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A Direct, Regioselective and Atom-Economical Synthesis of 3-Aroyl-N-hydroxy-5-nitroindoles by Cycloaddition of 4-Nitronitrosobenzene with Alkynones

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New Polyindolenine Alkaloids from Calycodendron milnei.

Y Adjibadé¹, H Saad, T Sévenet

¹Université Louis Pasteur, Faculté de Pharmacie, Laboratoire de Pharmacognosie, B.P. 24, F-67401 Illkirch Cédex, France.

|April 1, 1990

Summary

Four novel polyindolinic alkaloids were discovered in CALYCODENDRON MILNEI. These compounds, named vatine, vatine A, vatamine, and vatamidine, are polymers of N(b)-methyltryptamine units.

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Area of Science:

Natural Product Chemistry
Phytochemistry
Organic Chemistry

Background:

CALYCODENDRON MILNEI is a plant species known for its potential chemical constituents.
Alkaloids represent a diverse class of natural products with significant pharmacological interest.

Purpose of the Study:

To isolate and characterize new alkaloid compounds from CALYCODENDRON MILNEI.
To investigate the structural diversity of polyindolinic alkaloids.

Main Methods:

Extraction of alkaloids from the aerial parts of CALYCODENDRON MILNEI.
Isolation and purification of compounds using chromatographic techniques.
Structure elucidation using spectroscopic methods (e.g., NMR, Mass Spectrometry).

Main Results:

Isolation of four new polyindolinic alkaloids: vatine, vatine A, vatamine, and vatamidine.
Identification of these alkaloids as polymers composed of six, seven, and eight N(b)-methyltryptamine units.
Vatine and vatine A represent a stereoisomeric pair.

Conclusions:

The discovery of vatine, vatine A, vatamine, and vatamidine expands the known structural classes of polyindolinic alkaloids.
These findings contribute to the understanding of the chemical diversity within the CALYCODENDRON genus.
Further research may explore the biological activities of these novel alkaloids.