Date of Award

1978

Document Type

Dissertation

Degree Name

Doctor of Philosophy (Ph.D.)

Department

Graduate School

First Advisor

Madhukar Chaubal

First Committee Member

Donald K. Wedegaertner

Second Committee Member

John K. Brown

Third Committee Member

Marvin Malone

Fourth Committee Member

Donald M. Pace

Abstract

The genus Brunfelsia (Fam. Solannceae) comprises some 40 species of shrubs native to South Africa and West Indies. Brunfelsia hopeana (common name: Manaca root) and related species are recognized in folk medicine in South America as being useful as diuretic, antirheumatic, antisyphilitic agents and as narcotic hallucinogens. In view of the interesting folkloric uses and a paucity of chemical and pharmacological investigation of B. hopeana, a systematic phytochemical and pharmacological investigation on B. hopeana was undertaken in our laboratory.

Hippocratic screening of the whole root powder and extracts of B. hopeana administered intrapcritonially to rats, indicated that the whole root had CNS depressant activity and that the chloroform extract which contained the basic or 'alkaloidal' fraction concentrates this activity. The chloroform extract at an oral dose level of 100 mg/Kg, was equally effective (w/w) as rhenylbutazone in reducing carrageenin-induced pedal edema in rats.

In addition, the extract also exhibited significant in vitro selective toxicity against SV 3T3 cells at a dose level of 2000 µg/ml. Based en these results, detailed studies on the isolation and characterization of the constituents of the chloroform extract: were carried out.

A large-scale extraction of the plant material provided significant amounts of the chloroform. extract for further study. Isolation of the constituents of the extract, was carried out using Column- and Preparative Thin-Layer Chromatography. Three alkaloids designated as Alkaloid I, Alkaioid II, and Alkaloid III and in addition a previously isolated coumarin compound, Scopoletin, were obtained from the chloroform extract. The major 'alkaloidal' component was Alkaloid III. The structure of this compound was elucidated with the help of UV, IR, PMR. C-13 NMR and Low- and High Resolution Mass Spectroscopy.

Based on these data, the following structure was assigned to Alkaloid III. (SEE TEXT OF DISSERTATION FOR IMAGE)

A survey of the literature to date showed that the structure of Alkaloid III was unique and new; being reported for the first time. The name 'Hopeanine' was therefore given to this compound. Alkaloid I and Alkaloid II were obtained in small amounts and hence only partial characterization of these two constituents could be achieved.

Pages

132

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