Abstract
Three new secondary metabolites, amycofuran (1), amycocyclopiazonic acid (2), and amycolactam (3), were isolated from the sponge-associated rare actinomycete Amycolatopsis sp. Based on combined spectroscopic analyses, the structures of 1–3 were determined to be a new benzofuran glycoside and new indole alkaloids related to cyclopiazonic acids, a class that has previously only been reported in fungi. The absolute configurations of 1 and 3 were deduced by ECD calculations, whereas that of 2 was determined using the modified Mosher method. Amycolactam (3) displayed significant cytotoxicity against the gastric cancer cell line SNU638 and the colon cancer cell line HCT116.
Highlights
IntroductionNatural products from marine organisms have been proposed as “a new wave of drugs” because of their great potential for supplying structurally and biologically novel compounds for drug discovery [1]
Natural products from marine organisms have been proposed as “a new wave of drugs” because of their great potential for supplying structurally and biologically novel compounds for drug discovery [1].As of 2013, several drugs derived from marine natural products are in clinical use
We found that a rare actinomycete strain (Cra33g) belonging to Amycolatopsis sp., produced a new benzofuran glycoside, as well as two new indole alkaloids, which are quite rare as bacterial metabolites
Summary
Natural products from marine organisms have been proposed as “a new wave of drugs” because of their great potential for supplying structurally and biologically novel compounds for drug discovery [1]. As of 2013, several drugs derived from marine natural products are in clinical use. A [7], and psymberin [8] were shown to be bacterially produced natural products These results have spurred the study of the chemistry and phylogenetic diversity of symbiotic microbial communities in marine invertebrates [9,10]. Actinomycetes, belonging to the phylum Actinobacteria, are prolific chemical synthesizers, providing 40% of the 33,500 microbial bioactive compounds reported as of 2010, including numerous drugs in clinical use [11]. Compared to the phylogenetic analysis of sponge-associated microbial communities, the chemical investigation of sponge-associated actinomycetes is only just beginning, as demonstrated by a few recent examples, including new nucleoside analogs discovered from Streptomyces microflavus in association with the sponge. We report the structural elucidation and biological activity of these three new compounds from the Amycolatopsis strain: amycofuran (1), amycocyclopiazonic acid (2), and amycolactam (3) (Figure 1)
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