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IBUB research group attains the first total synthesis of madangamine D, a molecule of biomedical interest

By 11 de July de 2014November 18th, 2020No Comments
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This is the first total synthesis of a sponge isolated marine alkaloid with complex structure.
 11.07.2014

IBUB research group attains the first total synthesis of madangamine D, a molecule of biomedical interest

Madangamines are a group of polycyclic alkaloids from marine sponges which have biomedical interest due to their cytotoxic activity. A research group from the Faculty of Pharmacy ot the University of Barcelona (UB) and the Institute of Biomedicine of UB (IBUB) has just described on a paper published in the journal Angewandte Chemie International Edition (doi: 10.1002/anie.201402263) the first total synthesis of madangamine D, a scientific discovery in the field of organic chemistry.


Sponges are a group of marine organisms rich in bioactive products. However, it is usually very difficult to develop in-depth studies about their biological activity because they contain isolated small quantities of these products. Madangamines A and F have shown significant cytotoxicity against a number of tumour cell lines. In the study, madangamine D showed significant in vitro cytotoxic activity against human colon and pancreas cancer cell lines.

To successfully accomplish the synthesis of madangamine D, experts use the knowledge attained by the UB research group in order to use phenylglycinol-derived bicyclic lactams in the enantioselective synthesis of piperidine-containing alkaloids. By using this type of lactam, the diazatricyclic ABC core, common to all madangamines, was synthetized in a completely stereocontrolled way. Once the core is obtained, madangamine D macrocyclic rings are elaborated.

This is the first total synthesis of a sponge isolated marine alkaloid with complex structure. The synthesis has enabled for the first having a pure sample of this natural product, as when it was isolated, in really small quantities, madangamine D was not pure as it was mixed with other alkaloid of the same group (madangamine E). Consequently, the UB research group was able to carry out bioactivity assays. Furthermore, enantioselective synthesis enabled to prove the configuration of this alkaloid family.

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