Terpenyl-purines from the sea

Abstract

Agelasines, asmarines and related compounds are natural products with a hybrid terpene-purine structure isolated from numerous genera of sponges (Agela sp., Raspailia sp.). Some agelasine analogs and related structures have displayed high general toxicity towards protozoa, and have exhibited broad-spectrum antimicrobial activity against a variety of species, including Mycobacterium tuberculosis, and also an important cytotoxic activity against several cancer cell lines, including multidrug-resistant ones. Of particular interest in this context are the asmarines (tetrahydro[1,4]diazepino[1,2,3-g,h]purines), which have shown potent antiproliferative activity against several types of human cancer cell lines. This review summarizes the sources of isolation, chemistry and bioactivity of marine alkylpurines and their bioactive derivatives.

Keywords: agelasimine; agelasine; ageline; alkyl-purine; asmarine; terpene-purine; terpenylpurine.

Figure 1.

Structures of agelasines A–L.

Figure 1.

Structures of agelasines A–L.

Figure 2.

Structure of agelasimines A and B.

Figure 3.

Structure of agelasidines A, B and C (guanidine derivatives, diterpene derivatives of hypotaurocyamine).

Figure 4.

Structures of asmarines.

Figure 5.

Methylpurines from marine organisms.

Scheme 1.

General synthetic route to agelasines [71].

Scheme 2.

Retrosynthetic route to agelasine D [79].

Scheme 3.

Retrosynthetic analysis of agelasine F [82].

Scheme 4.

Synthetic routes to asmarines [83].