A submarine journey: The pyrrole-imidazole alkaloids

Barbara Forte; Beatrice Malgesini; Claudia Piutti; Francesca Quartieri; Alessandra Scolaro; Gianluca Papeo

doi:10.3390/md7040705

A submarine journey: The pyrrole-imidazole alkaloids

Barbara Forte, Beatrice Malgesini, Claudia Piutti, Francesca Quartieri, Alessandra Scolaro, Gianluca Papeo (Lead / Corresponding author)

Drug Discovery Unit

Research output: Contribution to journal › Review article › peer-review

219 Citations (Scopus)

51 Downloads (Pure)

Abstract

In his most celebrated tale "The Picture of Dorian Gray", Oscar Wilde stated that "those who go beneath the surface do so at their peril". This sentence could be a prophetical warning for the practitioner who voluntarily challenges himself with trying to synthesize marine sponge-deriving pyrrole-imidazole alkaloids. This now nearly triple-digit membered community has been growing exponentially in the last 20 years, both in terms of new representatives and topological complexity - from simple, achiral oroidin to the breathtaking 12-ring stylissadines A and B, each possessing 16 stereocenters. While the biosynthesis and the role in the sponge economy of most of these alkaloids still lies in the realm of speculations, significant biological activities for some of them have clearly emerged. This review will account for the progress in achieving the total synthesis of the more biologically enticing members of this class of natural products.

Original language	English
Pages (from-to)	705-753
Number of pages	49
Journal	Marine Drugs
Volume	7
Issue number	4
DOIs	https://doi.org/10.3390/md7040705
Publication status	Published - Dec 2009

Keywords

Marine sponges
Oroidin
Pyrrole-imidazole alkaloids
Total synthesis

ASJC Scopus subject areas

Drug Discovery

UN SDGs

This output contributes to the following UN Sustainable Development Goals (SDGs)

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10.3390/md7040705Licence: CC BY

Final Published VersionFinal published version, 426 KBLicence: CC BY

Cite this

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title = "A submarine journey: The pyrrole-imidazole alkaloids",

abstract = "In his most celebrated tale {"}The Picture of Dorian Gray{"}, Oscar Wilde stated that {"}those who go beneath the surface do so at their peril{"}. This sentence could be a prophetical warning for the practitioner who voluntarily challenges himself with trying to synthesize marine sponge-deriving pyrrole-imidazole alkaloids. This now nearly triple-digit membered community has been growing exponentially in the last 20 years, both in terms of new representatives and topological complexity - from simple, achiral oroidin to the breathtaking 12-ring stylissadines A and B, each possessing 16 stereocenters. While the biosynthesis and the role in the sponge economy of most of these alkaloids still lies in the realm of speculations, significant biological activities for some of them have clearly emerged. This review will account for the progress in achieving the total synthesis of the more biologically enticing members of this class of natural products.",

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language = "English",

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AU - Forte, Barbara

AU - Malgesini, Beatrice

AU - Piutti, Claudia

AU - Quartieri, Francesca

AU - Scolaro, Alessandra

AU - Papeo, Gianluca

PY - 2009/12

Y1 - 2009/12

N2 - In his most celebrated tale "The Picture of Dorian Gray", Oscar Wilde stated that "those who go beneath the surface do so at their peril". This sentence could be a prophetical warning for the practitioner who voluntarily challenges himself with trying to synthesize marine sponge-deriving pyrrole-imidazole alkaloids. This now nearly triple-digit membered community has been growing exponentially in the last 20 years, both in terms of new representatives and topological complexity - from simple, achiral oroidin to the breathtaking 12-ring stylissadines A and B, each possessing 16 stereocenters. While the biosynthesis and the role in the sponge economy of most of these alkaloids still lies in the realm of speculations, significant biological activities for some of them have clearly emerged. This review will account for the progress in achieving the total synthesis of the more biologically enticing members of this class of natural products.

AB - In his most celebrated tale "The Picture of Dorian Gray", Oscar Wilde stated that "those who go beneath the surface do so at their peril". This sentence could be a prophetical warning for the practitioner who voluntarily challenges himself with trying to synthesize marine sponge-deriving pyrrole-imidazole alkaloids. This now nearly triple-digit membered community has been growing exponentially in the last 20 years, both in terms of new representatives and topological complexity - from simple, achiral oroidin to the breathtaking 12-ring stylissadines A and B, each possessing 16 stereocenters. While the biosynthesis and the role in the sponge economy of most of these alkaloids still lies in the realm of speculations, significant biological activities for some of them have clearly emerged. This review will account for the progress in achieving the total synthesis of the more biologically enticing members of this class of natural products.

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KW - Pyrrole-imidazole alkaloids

KW - Total synthesis

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A submarine journey: The pyrrole-imidazole alkaloids

Abstract

Keywords

ASJC Scopus subject areas

UN SDGs

Access to Document

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