Isolation and Synthesis of Veranamine, an Antidepressant Lead from the Marine Sponge Verongula rigida

The natural product veranamine was isolated from the marine sponge Verongula rigida. It contains a unique heterocyclic scaffold and demonstrates in vivo antidepressant activity and selective affinity for 5HT2B and sigma-1 receptors. The first total synthesis of veranamine is reported. Our scalable s...

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Bibliographic Details
Published in:Journal of natural products (Washington, D.C.) D.C.), 2020-04, Vol.83 (4), p.1092-1098
Main Authors: Kochanowska-Karamyan, Anna J, Araujo, Hugo C, Zhang, Xiong, El-Alfy, Abir, Carvalho, Paulo, Avery, Mitchell A, Holmbo, Stephen D, Magolan, Jakob, Hamann, Mark T
Format: Article
Language:English
Subjects:
Animals
Antidepressive Agents - chemistry
Antidepressive Agents - isolation & purification
Antidepressive Agents - pharmacology
Molecular Structure
Porifera - chemistry
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Summary:The natural product veranamine was isolated from the marine sponge Verongula rigida. It contains a unique heterocyclic scaffold and demonstrates in vivo antidepressant activity and selective affinity for 5HT2B and sigma-1 receptors. The first total synthesis of veranamine is reported. Our scalable synthesis offers veranamine in six steps and 25% yield via an unprecedented vinylogous Pictet–Gams pyridine formation strategy. Veranamine is a promising new lead compound for antidepressant drug development.
ISSN:0163-3864
1520-6025
1520-6025
DOI:10.1021/acs.jnatprod.9b01107