Structural diversity and chemical synthesis of peroxide and peroxide-derived polyketide metabolites from marine sponges

Abstract

Covering: up to early 2016Marine sponges are widely known as a rich source of natural products, especially of polyketide origin, with a wealth of chemical diversity. Within this vast collection, peroxide and peroxide-derived secondary metabolites have attracted significant interest in the fields of natural product isolation and chemical synthesis for their structural distinction and promising in vitro antimicrobial and anticancer properties. In this review, peroxide and peroxide-derived polyketide metabolites isolated from marine sponges in the past 35 years are summarised. Efforts toward their synthesis are detailed with a focus on methods that utilise or attempt to elucidate the complex biosynthetic interrelationships of these compounds beyond enzymatic polyketide synthesis. Recent isolations, advances in synthetic methodology and theories of biogenesis are highlighted and critically evaluated.

Detecting signatures of a sponge‐associated lifestyle in bacterial genomes

“…While two of these four functions have only predicted properties (COG1483 and COG4637), which makes speculations about their role difficult, the unique presence of O ‐methyltransferase involved in polyketide synthesis and the ankyrin repeats are of interest. O ‐methyltransferases are involved in the chemical tailoring of polyketides, which are a chemical class frequently found in sponges and which potentially have antagonistic activities that would benefit the sponge (Norris and Perkins, ). Ankyrin repeats are a class of eukaryotic‐like proteins that are abundantly found in metagenomes and metatranscriptomes of sponge‐associated microbial communities (Fan et al ., ; Díez‐Vives et al ., ) and which have been recently shown to interfere with eukaryotic phagocytosis (Nguyen et al ., ; Reynolds and Thomas, ).…”

Cytotoxicity of Endoperoxides from the Caribbean Sponge Plakortis halichondrioides towards Sensitive and Multidrug-Resistant Leukemia Cells: Acids vs. Esters Activity Evaluation

“…Endoperoxides are, therefore, worth investigating to unravel their full potential as anticancer drug leads. The Caribbean sponge Plakortis halichondrioides produces endoperoxides which were assumed to be synthesized by the polyketide pathway [26,27]. Similar to artesunate, these metabolites did not only display antimalarial activity, but also cytotoxic activity against several tumor cell lines [28,29,30].…”

Six-Membered Ring Systems

“…Reviews on natural products covered the origins and medicinal use of avermectins (16AGE10190), discovery, isolation, characterization and application of artemisinin (16AGE10210), biosynthesis of fungal meroterpenoids (16NPR26), isolation, biological properties, and synthesis of dimeric pyranonaphthoquinones (16EJO5778), and peroxide and peroxide-derived polyketide metabolites from marine sponges (16NPR861). Late-stage convergent annulation reactions (16T3345) and rhodium-catalyzed annulation reactions of arenes with alkynes via weak chelation-assisted CdH activation (16CC2872) for the synthesis of several natural six-membered oxacycles have also been reviewed.…”