Aranciamycin K (1) and isotirandamycin B (2) were isolated from a marine-derived Streptomyces sp. SCSIO 41399, along with the previously reported four anthracycline derivatives (3–6), and two known tirandamycin derivatives (7 and 8). Their structures including absolute configurations were determined by extensive analysis of their spectroscopic analysis and ECD calculation method. Most of the isolated compounds were tested for their cytotoxic, antibacterial, and antifungal activities. Compounds 2, 7 and 8 displayed potent bacteriostatic effects against Streptococcus agalactiae with MIC values of 11.5, 5.9 and 5.7 μM, respectively. Besides, compounds 3, 5 and 6 exhibited moderate in vitro cytotoxic activities against the K562 cell lines with IC50 values of 22.0 ± 0.20, 1.80 ± 0.01 and 12.1 ± 0.07 μM, respectively.
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Laatsch H, Fotso S. Naturally occurring anthracyclines. Top Curr Chem. 2008;282:3–74.
Gui C, Mo XH, Gu YC, Ju JH. Elucidating the sugar tailoring steps in the cytorhodin biosynthetic pathway. Org Lett. 2017;19:5617–20.
Sann CL. Maleimide spacers as versatile linkers in the synthesis of bioconjugates of anthracyclines. Nat Prod Rep. 2006;23:357–67.
Royles BJL. Naturally occurring tetramic acids: structure, isolation, and synthesis. Chem Rev. 1995;95:1981–2001.
Mo XH, Huang HB, Ma JY, Wang ZW, Wang B, Zhang S, et al. Characterization of TrdL as a 10-hydroxy dehydrogenase and generation of new analogues from a tirandamycin biosynthetic pathway. Org Lett. 2011;13:2212–5.
Carlson JC, Li SY, Burr DA, Sherman DV. Isolation and characterization of tirandamycins from a marine-derived streptomyces sp. J Nat Prod. 2009;72:2076–9.
Carlson JC, Li SY, Gunatilleke SS, Anzai Y, Burr DA, Podust LM, et al. Tirandamycin biosynthesis is mediated by co-dependent oxidative enzymes. Nat Chem. 2011;3:628–33.
Pang XY, Lin XP, Wang JF, Liang R, Tian YQ, Salendra L, et al. Three new highly oxygenated sterols and one new dihydroisocoumarin from the marine sponge-derived fungus Cladosporium sp. SCSIO41007. Steroids. 2018;129:41–6.
Chen ST, Wang JF, Wang Z, Lin XP, Zhao BX, Kaliaperumal K, et al. Structurally diverse secondary metabolites from a deep-sea-derived fungus Penicillium chrysogenum SCSIO 41001 and their biological evaluation. Fitoterapia. 2017;117:71–8.
Wang JF, Wei XY, Qin XC, Lin XP, Zhou XF, Liao SR, et al. Arthpyrones A–C, pyridone alkaloids from a sponge-derived fungus Arthrinium arundinis ZSDS1-F3. Org Lett. 2015;17:656–9.
Johdo O, Yoshioka T. Isolation of new anthracyclines 10-O-rhodosaminyl β-rhodomycinone and β-isorhodomycinone from mild-acid treated culture of obelmycin-producing Streptomyces violaceus. J Antibiot. 1997;50:522–5.
Hermentin P, Raab E, Paal M, Boettger D, Berscheid HG, Gerken M, et al. Synthesis and structure elucidation of p-methoxybenzoyl derivatives of rhodomycins. J Carbohyd Chem. 1989;8:255–63.
Wang JF, He WJ, Huang XL, Tian XP, Liao SR, Yang B, et al. Antifungal new oxepine-containing alkaloids and xanthones from the deep-sea-derived fungus Aspergillus versicolor SCSIO 05879. J Agric Food Chem. 2016;64:2910–6.
This work was financially supported by the National Natural Science Foundation of China (Nos. 41776169, 41476135, 21502204, 21772210, 81741154 and 81741158), Science and Technology Project of Guangdong Province (No. 2016A020222010), Pearl River S&T Nova Program of Guangzhou (No. 201710010136) and the High Education Teaching and reform Research Fund Program of Hainan province (number Hnjg2017ZD-3). We are grateful for the analytical facilities provided in SCSIO.
Conflict of interest
The authors declare that they have no conflict of interest.