This review summarizes the methylene-bridged dimeric natural products involving one-carbon unit in biosynthesis, including their structures, biological activities, synthetic methods, and formation mechanisms.
Four new aromatic polyketides, wailupemycins M− P (1−4), and two new hydroxamate siderophores, streptamides A (5) and B (6), together with the previously reported nocardamine (7), were isolated from the marine-algae-derived Streptomyces sp. OUCMDZ-3434. Wailupemycins M−P (1−4), possessing an αpyrone moiety, were isolated from the extract of a liquid fermentation, and the siderophores (5−7) were isolated from the extract of a solid fermentation. Their structures were assigned based on detailed spectroscopic analysis and quantum chemical calculations. Compounds 5−7 were capable of binding Fe(III). Compound 5 can form a tighter Fe(III) complex than that of deferoxamine B mesylate (DFB).
To expand the chemical diversity of secondary metabolites produced by two marine-derived enterocin-and wailupemycin-producing Streptomyces strains, OUCMDZ-3434 and OUCMDZ-2599, precursor feeding and solid fermentation strategies were used. Two new compounds, wailupemycins Q (1) and R (2), were isolated from the extracts of liquid and solid fermentation of OUCMDZ-3434. Furthermore, during the fermentation of OUCMDZ-3434, p-fluorobenzoic acid was added as the key biosynthetic precursor, which resulted in the isolation of eight new fluorinated enterocin and wailupemycin derivatives (3− 10) and 10 previously reported analogues (11−20). From the solid fermentation extract of OUCMDZ-2599, a new sulfur-containing compound thiotetromycin B (21) and its known analogue thiotetromycin (22) were identified. Moreover, the solid fermentation strategy effectively activated the biosynthesis of siderophores (23−25) of strain OUCMDZ-2599. Compound 3 showed moderate antibacterial activity against Staphylococcus aureus and methicillin-resistant Staphylococcus aureus subsp. aureus with MIC values of 4 μg/mL. Compounds 23−25 were significantly capable of binding Fe(III).
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