Files

650745.pdf (2.67 MB)

Embargo

Item embargoed until 2099-01-01

Document type

Book part

Version

Accepted version

Publication date

2015

All rights reserved

Please use this identifier to cite or link to this item: https://hdl.handle.net/2445/164418

The Alkaloids of the Madangamine Group

Journal Title

Authors

Director/Tutor

Journal ISSN

Volume Title

Related resource

https://doi.org/10.1016/bs.alkal.2014.10.001

Abstract

This chapter is focused on madangamines, a small group of complex diamine alkaloids isolated from marine sponges of the order Haplosclerida, and covers their isolation, characterization, biogenesis, biological activity, and synthesis. Structurally, madangamines are pentacyclic alkaloids with an unprecedented skeletal type, characterized by a common diazatricyclic core and two peripheral macrocyclic rings. The isolation of these alkaloids from Xestospongia ingens (madangamines A E) and Pachychalina alcaloidifera (madangamine F) is described in detail. Physical and complete spectroscopic 1H and 13C NMR data are included. The proposed biogenesis of madangamines from ammonia, a functionalized three-carbon unit, and saturated or unsaturated linear long-chain dialdehydes, via partially reduced bis-alkylpyridine macrocycles, is discussed. The synthesis of alkaloids of the madangamine group has been little explored, with only one total synthesis reported so far, that of (þ)-madangamine D. This review also describes several model synthetic approaches to the diazatricyclic ABC core of these alkaloids, as well as model studies on the construction of the (Z,Z)-unsaturated 11-membered E macrocycle common to madangamines A E, the 13- and 14-membered D rings of madangamines C E, and the all-cistriunsaturated 15-membered D ring of madangamine A. Some members of this group have shown significant in vitro cytotoxicity against a number of cancer cell lines.

Subject

Alcaloides, Productes naturals marins, Síntesi orgànica, Enantiòmers

Subject (English)

Alkaloids, Marine natural products, Organic synthesis, Enantiomers

Citation

Collections

Llibres / Capítols de llibre (Nutrició, Ciències de l'Alimentació i Gastronomia)
Llibres / Capítols de llibre (Farmacologia, Toxicologia i Química Terapèutica)

Citation

AMAT TUSÓN, Mercedes, et al. The Alkaloids of the Madangamine Group. The Alkaloids: Chemistry and Biology. 2015. Vol. 74, num. 159-199. ISSN 1099-4831. [consulted: 14 of June of 2026]. Available at: https://hdl.handle.net/2445/164418

Export metadata

JSON - METS

Share record