Chemistry and Biology of Bengamides and Bengazoles, Bioactive Natural Products from Jaspis Sponges

Cristina García-Ruiz,Francisco Sarabia

doi:10.3390/md12031580

Abstract

Sponges corresponding to the Jaspidae family have proved to be a prolific source of bioactive natural products. Among these, the bengamides and the bengazoles stand out by virtue of their unprecedented molecular architectures and impressive biological profiles, including antitumor, antibiotic and anthelmintic properties. As a consequence, intense research activity has been devoted to these compounds from both chemical and biological standpoints. This review describes in detail the research into these classes of natural products and the benefits they offer in chemistry and biology.

Highlights

The sponges corresponding to the Jaspidae family represent a valuable source of interesting natural products, some of which display impressive biological profiles such as antitumoral, anthelmintic and antibiotic properties
Its isolation from Jaspis johnstoni [5] was followed by the discovery of new members, the jaspamides B–P (2–15) [6,7,8,9], from other sponges belonging to the Jaspis family and with similar striking antitumor properties
As a consequence of these results, a more detailed study focused on the 14-3-3 protein family revealed a retention of the initiator methionine in the isoform 14-3-3 when treated with the bengamides, and allowed to determine the direct targets of bengamides as both human methionine aminopeptidases (MetAP) isoforms, MetAP1 and MetAP2

Summary

Introduction

The sponges corresponding to the Jaspidae family represent a valuable source of interesting natural products, some of which display impressive biological profiles such as antitumoral, anthelmintic and antibiotic properties. This class of sponges has been mainly collected in the Indian Ocean and has provided a wide array of natural products in terms of structural diversity and biological properties, there are three classes of natural compounds that stand out over the rest, the bengamides [1], the bengazoles [2] and the jaspamides [3] (Figure 1) due to their unique molecular architectures and biological activities. Rhabdastrella cf. globostellata [30], Stellata globostellata [31] and Geodia globostellifera [32]. e Jaspines were described from Pachastrissa sp. [33]

Chemistry and Biology of the Bengamides

Antitumor Properties and Mechanism of Action

Chemical Synthesis of Natural Bengamides

Synthesis of Bengamide Analogues and Biological Evaluation

Discovery and Structural Elucidation of Bengazoles

Biology of Bengazoles

Chemical Synthesis of Bengazoles

Findings

Conclusions