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Dioncophylline E From Dioncophyllum Thollonii, the First 7,3'-coupled Dioncophyllaceous Naphthylisoquinoline Alkaloid

Dioncophylline E From Dioncophyllum Thollonii, the First 7,3'-coupled Dioncophyllaceous Naphthylisoquinoline Alkaloid

Gerhard Bringmann, Kim Messer, Kristina Wolf, Jörg Mühlbacher, Matthias Grüne, Reto Brun, Adriaan M Louis

Phytochemistry. 2002 Jun;60(4):389-97.

PMID: 12031431

Abstract:

The isolation and structural elucidation of dioncophylline E, a novel naphthylisoquinoline alkaloid from the rare West African liana Dioncophyllum thollonii, is described. The alkaloid displays an unusual 7,3'-linkage between the naphthalene and the isoquinoline portions. Due to the resulting medium degree of steric hindrance exerted by the ortho-substituents next to the biaryl axis, the compound undergoes slow rotation about the axis at room temperature and thus is the first such alkaloid that occurs as a mixture of two configurationally semi-stable atropo-diastereomers. Dioncophylline E exhibits good antimalarial activity against both chloroquine-sensitive and -resistant strains of Plasmodium falciparum while its antitrypanosomal activity against Trypanosoma cruzi is weak and that against T. brucei rhodesiense is moderate. Furthermore, four additional naphthylisoquinoline alkaloids previously known from the related plant species Triphyophyllum peltatum, have been identified in D. thollonii.

Chemicals Related in the Paper:

Catalog Number	Product Name	Structure	CAS Number	Price
ALP5428615	Chloroquine Related Compound E		5428-61-5 (free base)	Price

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