Abstract

Exploration for specialized metabolites of Okinawan marine sponges Agelas spp. resulted in the isolation of five new bromopyrrole alkaloids, agesasines A (1) and B (2), 9-hydroxydihydrodispacamide (3), 9-hydroxydihydrooroidin (4), and 9E-keramadine (5). Their structures were elucidated on the basis of spectroscopic analyses. Agesasines A (1) and B (2) were assigned as rare bromopyrrole alkaloids lacking an aminoimidazole moiety, while 3–5 were elucidated to be linear bromopyrrole alkaloids with either aminoimidazolone, aminoimidazole, or N-methylated aminoimidazole moieties.

Highlights

  • A number of structurally unique bioactive specialized metabolites have been isolated from marine sources including sponges, algae, cnidarians, and marine microorganisms, etc. [1]

  • In our search for structurally unique marine natural products [6,7,8], we have recently reported the isolation of diterpene alkaloids from the extracts of a marine sponge Agelas spp

  • As part of this research project, we have investigated another specimen of Agelas marine sponges, which resulted in the isolation of five new bromopyrrole alkaloids (1–5)

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Summary

Introduction

A number of structurally unique bioactive specialized metabolites have been isolated from marine sources including sponges, algae, cnidarians, and marine microorganisms, etc. [1]. A number of structurally unique bioactive specialized metabolites have been isolated from marine sources including sponges, algae, cnidarians, and marine microorganisms, etc. Natural products isolated from marine sponges are recognized as an attractive source of leads for therapeutic agents due to a diversity of their chemical structures and biological activities. Marine sponges belonging to the genus Agelas are known to be a rich source of bromopyrrole alkaloids and diterpene alkaloids that have been used as a taxonomically characteristic maker [5]. In our search for structurally unique marine natural products [6,7,8], we have recently reported the isolation of diterpene alkaloids from the extracts of a marine sponge Agelas spp.

Isolation
Structure Elucidation of 1–5
Key two-dimensional correlationsfor foragesasines agesasines
Selected
Selected correlationsfor for 9-hydroxydihydrooroidin
General Procedures
Extraction and Isolation
Optical Resolutions of 1–3
Evaluation for Antiproliferative Activity of 1–5
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