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Jozimine A2 : the first dimeric dioncophyllaceae-type naphthylisoquinoline alkaloid, with three chiral axes and high antiplasmodial activity

Bringmann, G. and Zhang, G. and Büttner, T. and Bauckmann, G. and Kupfer, T. and Braunschweig, H. and Brun, R. and Mudogo, V.. (2013) Jozimine A2 : the first dimeric dioncophyllaceae-type naphthylisoquinoline alkaloid, with three chiral axes and high antiplasmodial activity. Chemistry : a European journal, Vol. 19, H. 3. S. 916-923.

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Official URL: http://edoc.unibas.ch/dok/A6094254

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Abstract

A new dimeric naphthylisoquinoline alkaloid, jozimine A(2) (2), was isolated from the root bark of an Ancistrocladus species from the Democratic Republic of Congo. Its absolute stereostructure was determined by chemical, spectroscopic, and chiroptical methods, and confirmed by X-ray crystallography. Jozimine A(2) (2) is one of the as yet very rare naphthylisoquinoline dimers whose central biaryl axis is rotationally hindered. Moreover, it is the first natural dimer of a Dioncophyllaceae-type alkaloid, that is, lacking oxygen functions at C6, and bearing R configurations at C3 in its two isoquinoline portions. Despite this decreased steric hindrance, the outer biaryl axes are chiral, too, so that jozimine A(2) (2) has three consecutive stereogenic axes and, together with the four stereogenic centers, seven elements of chirality and is C(2) -symmetric. The new dimer exhibits excellent, and specific, antiplasmodial activity. To further confirm its stereostructure and for likewise testing the bioactivities of its (unnatural) atropo-diastereomer, compound 2 was prepared by semi-synthesis from the co-occurring (and likewise synthetically available) dioncophylline A (5), along with its atropo-diastereomer, 3'-epi-2.
Faculties and Departments:09 Associated Institutions > Swiss Tropical and Public Health Institute (Swiss TPH) > Department of Medical Parasitology and Infection Biology > Parasite Chemotherapy (Mäser)
UniBasel Contributors:Brun, Reto
Item Type:Article, refereed
Bibsysno:Link to catalogue
Publisher:Wiley-VCH Verlag
ISSN:0947-6539
Note:Publication type according to Uni Basel Research Database: Journal article
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Last Modified:16 Aug 2013 07:34
Deposited On:16 Aug 2013 07:30

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