Abstract
Marine actinomycetes are prolific chemical sources of complex and novel natural products, providing an excellent chance for new drug discovery. The chemical investigation of the marine-derived Streptomyces sp. ITBB-ZKa6, from Zhaoshu island, Hainan, led to the discovery of two unique antimycin-type depsipeptides, zhaoshumycins A (1) and B (2), along with the isolation of the four known neoantimycins A (3), F (4), D (5), and E (6). The structures of the new compounds 1 and 2 were elucidated on the basis of the analysis of diverse spectroscopic data and biogenetic consideration. Zhaoshumycins A (1) and B (2) represent a new class of depsipeptides, featuring two neoantimycin monomers (only neoantimycin D or neoantimycins D and E) linked to a 1,4-disubstituted benzene ring via an imino group. Initial toxicity tests of 1–6 in MCF7 human breast cancer cells revealed that compounds 5 and 6 possess weak cytotoxic activity. Further structure–activity relationship analysis suggested the importance of the NH2 group at C-34 in 5 and 6 for cytotoxicity in MCF7 cells.
Highlights
Accepted: 2 November 2021Marine-derived actinomycetes are an excellent treasure house of structurally novel and biologically active natural products with potent medicinal properties [1,2,3,4,5]
During the analysis of novel natural products from the fermentation extract of actinomycetes from underexplored ecological niches, we discovered two unique dimeric antimycin-type depsipeptides, zhaoshumycins A (1) and B (2), together with the four known neoantimycins A (3), F (4), D (5), and E (6)
These compounds were obtained from the marine-derived Streptomyces sp
Summary
Accepted: 2 November 2021Marine-derived actinomycetes are an excellent treasure house of structurally novel and biologically active natural products with potent medicinal properties [1,2,3,4,5]. Antimycins are a family of depsipeptide compounds typically discovered in actinomycetes, displaying a broad range of promising biological activities including anticancer, antiviral, antifungal, and nematocidal effects [11] They are generated by a hybrid multimodular protein complex of non-ribosomal peptide synthetase and polyketide synthase assembly lines and have a common core structure composed of a macrocyclic ring with an amide linkage to a 3-formamidosalicylate unit [12,13,14]. This kind of depsipeptide natural products have attracted researchers’ attention due to their diverse structures and important bioactivities. Members of the antimycin family differ by the varying size of their macrocyclic ring and modifications of their ester forming α-hydroxy acid components
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