Recent progress regarding the bioactivities, biosynthesis and synthesis of naturally occurring resorcinolic macrolides

Abstract

Macrolides, which comprise a family of lactones with different ring sizes, belong to the polyketide class of natural products. Resorcinolic macrolides, an important subgroup, possess interesting structures and exhibit a wide variety of bioactivities, such as anti-tumor, anti-bacteria, and anti-malaria activities, etc. This review summarizes progress in isolation, bioactivity studies, biosynthesis, and representative chemical syntheses of this group of macrolides in recent decades, encompassing 63 naturally occurring macrolides published in 120 articles.

Comparison of 10,11‐Dehydrocurvularin Polyketide Synthases from Alternaria cinerariae and Aspergillus terreus Highlights Key Structural Motifs

“…[8] These effects and other biological activities have prompted a number of chemical syntheses of curvularin derivatives. [15–22] …”

Diversity-oriented combinatorial biosynthesis of benzenediol lactone scaffolds by subunit shuffling of fungal polyketide synthases

“…Among fungal polyketides, benzenediol lactones (BDLs) offer rich pharmacophores with an extraordinary range of biological activities (8). They are defined by a 1,3-benzenediol moiety bridged by a macrocyclic lactone ring (9).…”

“…10,11-dehydrocurvularin (7; Fig. 1) is a DAL with a 12-membered ring (DAL 12 ) that modulates the heat shock response and the immune system (8,9). BDL scaffolds are biosynthesized by pairs of collaborating, sequentially acting iterative polyketide synthases (iPKSs) (3) forming quasi-modular BDL synthases (BDLSs) (Fig.…”

Utilização de planejamento experimental para otimizar a produção de metabólitos secundários produzidos por Penicillium sp., isolado do ambiente marinho

“…A curvularina (25) foi a primeira lactona pertencente à família das DALs que foi isolada a partir do meio de cultura produzido por fungos (MUSGRAVE, 1956;Xu et. al., 2014).…”

“…al., 2014). Desde então foram identificados vários macrolídeos desta classe apresentando um anel benzênico substituído e vários tamanhos de anel da lactona, contendo duplas ligações, grupos carbonilas ou epóxidos, além de ligações a grupos metila ou hidroxila (XU et al, 2014). A curvularina e a 10,11-dehidrocurvularina (26) são as curvularinas mais conhecidas e foram isoladas a partir de diferentes espécies de fungos, tais como Aspergillus aureofulgens, Nectria galligena, Alternaria cinerariae, Chrysosporium lobatum.…”