Abstract
Separacenes A–D (1–4), novel polyene polyols, were isolated from Streptomyces sp. collected from the southern area of Jeju Island, Korea. The chemical structures of 1–4 were established by NMR, mass, UV, and IR spectroscopy as well as the modified Mosher’s method. Separacenes A–B (1–2), which share an identical planar structure but possess different relative configurations, bear tetraene units flanked by two diol moieties, whereas the stereoisomeric separacenes C–D (3–4) possess a triene moiety between two diol substructures. Separacenes A–D each contain a terminal olefinic methylene. Separacene A displayed inhibitory activity against Candida albicans isocitrate lyase and weak cytotoxicity against both the colon carcinoma cell line HCT-116 and the lung cancer cell line A549.
Highlights
Bioactive natural products represent a broad frontier in drug discovery [1]
We recently discovered a new macrocyclic lactone that functions as an isocitrate lyase inhibitor, bahamaolide A, from a Streptomyces sp. isolated from the Bahamas [9], and a new lasso peptide, sungsanpin, from another Streptomyces sp. collected from deep-sea areas off of Jeju Island, Korea [10]
Despite the lack of activity against the pathogenic fungi, separacene A displayed weak inhibitory activity against C. albicans isocitrate lyase (ICL), an enzyme that plays an important role in the pathogenicity of C. albicans [13], with an IC50 value of 45.7 μg/mL (172 μM)
Summary
Bioactive natural products represent a broad frontier in drug discovery [1]. Despite extensive study of the synthesis of bioactive compounds via directed organic and combinatorial methods, only 0.001% of synthetic compounds become drug candidates [2]. The secondary metabolites of actinomycetes are prolific sources of bioactive natural products for drug discovery [4]. As a result of several pioneering studies of marine actinomycetes, new drug candidates such as salinosporamide A and thiocoraline are in clinical trials for drug development. This clearly indicates the biomedical potential of marine actinomycetes [7,8]. As part of ongoing efforts to identify new bioactive compounds from marine actinomycetes, we selectively isolated actinomycetes from marine-derived sediment samples collected on seashores and chemically analyzed the cultures for secondary metabolite production. We report the isolation, structural determination (including absolute configurations), and biological activity of four new polyene polyols, separacenes A–D (1–4)
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