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Natural Product Research
Formerly Natural Product Letters
Volume 35, 2021 - Issue 8
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Research Article

Boshramycinones A-C: New anthracyclinones produced by a marine-derived Streptomyces sp.: isolation, structure elucidation and biological activities

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Pages 1281-1291 | Received 28 Apr 2019, Accepted 14 Jul 2019, Published online: 20 Aug 2019

References

  • Abdelfattah MS. 2009. Mansoquinone: isolation and structure elucidation of new antibacterial aromatic polyketides from terrestrial Streptomyces sp. Eg5. Nat Prod Res. 23(3):212–218.
  • Arcamone F, Cassinelli G, Fantini G, Grein A, Orezzi P, Pol C, Spalla C. 1969. Adriamycin, 14-hydroxydaunomycin, a new antitumor antibiotic from S. peucetius var. caesius. Biotechnol Bioeng. 11(6):1101–1110.
  • Balachandran C, Duraipandiyan V, Arun Y, Sangeetha B, Emi N, Al-Dhabi NA, Ignacimuthu S, Inaguma Y, Okamoto A, Perumal PT. 2016. Isolation and characterization of 2-hydroxy-9,10-anthraquinone from Streptomyces olivochromogenes (ERINLG-261) with antimicrobial and antiproliferative properties. Rev Bras Farmacogn. 26(3):285–295.
  • Brockmann H. 1963. Anthracyclinone und anthracycline. Fortschr Chem Org Naturst. 21:121–182.
  • Cassinelli G, Rivola G, Ruggieri D, Arcamone F, Grein A, Merli S, Spalla C, Casazza M, Di Marco A, Pratesi G. 1982. New anthracycline glycosides: 4-O-Demethyl-ll-deoxydoxorubicin and analogues from Streptomyces peucetius var. aureus. J Antibiot. 35(2):176–183.
  • Chapman & Hall Chemical Database. 2018. Dictionary of Natural Products on CD-ROM.
  • Cox G, Koteva K, Wright GD. 2014. An unusual class of anthracyclines potentiate Gram-positive antibiotics in intrinsically resistant Gram-negative bacteria. J Antimicrob Chemother. 69(7):1844–1855.
  • Dengler WA, Schulte J, Berger DP, Mertelsmann R, Fiebig HH. 1995. Development of a propidium iodide fluorescence assay for proliferation and cytotoxicity assays. Anti-Cancer Drugs. 6(4):522–532.
  • Dimarco A, Gaetani M, Orezzi P, Scarpinato BM, Silvestrini R, Soldati M, Dasdia T, Valentini L. 1964. 'Daunomycin', A new antibiotic of the rhodomycin group. Nature. 201:706–707.
  • Eckardt K, Tresselt D, Ihn W, Schumann G, Eritt I, Sedmera P, Novak J. 1991. Anthracyclinone-blue A and B, new natural anthracyclinones containing nitrogen in the molecules: isolation, chemical structures and biosynthesis. J Basic Microbiol. 31(5):371–376.
  • Elshahawi SI, Shaaban KA, Kharel MK, Thorson J. 2015. Comprehensive review of glycosylated bacterial natural products. Chem Soc Rev. 44(21):7591–7697.
  • Frändberg E, Petersson C, Lundgren LN, Schnürer J. 2000. Streptomyces halstedii K122 produces the antifungal compounds bafilomycin B1 and C1. Can J Microbiol. 46(8):753–757.
  • Frisch MJ, Trucks GW, Schlegel HB, Scuseria GE, Robb MA, Cheeseman JR, Scalmani G, Barone V, Mennucci B, Petersson GA, et al. 2009. Gaussian 09W, Version 7.0; Gaussian, Wallingford, CT.
  • Holkar S, Begde D, Nashikkar N, Kadam T, Upadhyay A. 2013. Rhodomycin analogues from Streptomyces purpurascens: isolation, characterization and biological activities. Springerplus. 2(1):93.
  • Ihn W, Wagner C, Fleck WF, Tresselt D, Eritt I, Sedmera P. 1984. Leukemomycin-blocked mutants of Streptomyces griseus and their pigments. II. New 7-hydroxy-bisanhydro-rhodomycinones from the mutant ZIMET 41707/1P. Z Allg Mikrobiol. 24:525–532.
  • Jizba JV, Sedmera P, Vokoun L, Blumauerová M, Vaněk Z. 1980. Naphthacenequinone derivatives from a mutant strain of Streptomyces coeruleorubidus. Collect Czech Chem Commun. 45(3):764–771.
  • Kawasaki M, Matsuda F, Terashima S. 1988. Synthetic studies on nogalamycin congener: total syntheses of (+)-nogarene, (+)-7-deoxynogarol, and (+)-7-con-o-methylnogarol. Tetrahedron. 44(18):5727–5743.
  • Kitahara T, Naganawa H, Okazaki T, Okami Y, Umezawa H. 1975. The structure of SS-228Y, an antibiotic from Chainia sp. J Antibiot. 28(4):280–285.
  • Krohn K, Broser E. 1982. Synthese des 3-Desmethoxyaranciamycinons. Liebigs Ann Chem. 1982(10):1907–1919.
  • Laatsch H, Fotso S. 2008. Naturally occurring anthracyclines. Top Curr Chem. 282:3–74.
  • Laatsch H. 2017. AntiBase: the natural compound identifier. Weinheim, Germany: Wiley.
  • Maskey RP, Grün-Wollny I, Laatsch H. 2003. Resomycins A – C: new anthracyclinone antibiotics formed by a terrestrial Streptomyces sp. J Antibiot. 56(9):795–800.
  • Moon SS, Hwang W, Chung YR, Shin J. 2003. New cytotoxic bafilomycin C1-amide produced by Kitasatospora cheerisanensis. J Antibiot. 56(10):856–861.
  • Nair V, Schuhmann I, Anke H, Kelter G, Fiebig H-H, Helmke E, Laatsch H. 2016. Marine bacteria, XLVII - psychrotolerant bacteria from extreme antarctic habitats as producers of rare bis- and trisindole alkaloids. Planta Med. 82(9–10):910–918.
  • O'Shea MG, Rickards RW, Rothschild JM, Lacey E. 1997. Absolute configurations of macrolide antibiotics of the bafilomycin and leucanicidin groups. J Antibiot. 50:1073–1077.
  • Pandey RC, Toussaint MW, McGuire JC, Thomas MC. 1989. Maggiemycin and anhydromaggiemycin: two novel anthracyclinone antitumor antibiotics. Isolation, structures, partial synthesis and biological properties. J Antibiot. 42(11):1567–1577.
  • Rong X, Guo Y, Huang Y. 2009. Proposal to reclassify the Streptomyces albidoflavus clade on the basis of multilocus sequence analysis and DNA-DNA hybridization, and taxonomic elucidation of Streptomyces griseus subsp. solvifaciens. Syst Appl Microbiol. 32(5):314–322.
  • Sajid I, Fondja YCB, Shaaban KA, Hasnain S, Laatsch H. 2009. Antifungal and antibacterial activities of indigenous Streptomyces isolates from saline farmlands: prescreening, ribotyping and metabolic diversity. World J Microbiol Biotechnol. 25(4):601–610.
  • SPARTAN'14 2014. Wavefunction, Irvine, CA (USA).
  • Tanaka H, Yoshioka T, Shimauchi Y, Matsuzawa Y, Oki T, Inui T. 1980. Chemical modification of anthracycline antibiotics. I. 10-Decarbomethoxylation, 10-epimerization and 4-O-methylation of aclacinomycin A. J Antibiot. 33(11):1323–1330.
  • Thibodeaux CJ, Liu H-W, Thorson JS. 2007. Complementary routes to natural product glycodiversification: pathway engineering and glycorandomization. In: Kamerling JP, Boons G-J, editors. Comprehensive glycoscience: from chemistry to systems biology. Vol. 3. Oxford: Elsevier.
  • Wagner C, Eckardt K, Schumann G, Ihn W, Tresselt D. 1984. Microbial transformation of aklanonic acid, a potential early intermediate in the biosynthesis of anthracyclines. J Antibiot. 37(6):691–692.
  • Werner G, Hagenmaier H, Drautz H, Baumgartner A, Zähner H. 1984. Metabolic products of microorganisms. 224. Bafilomycins, a new group of macrolide antibiotics. Production, isolation, chemical structure and biological activity. J Antibiot. 37(2):110–117.
  • Westman EL, Canova MJ, Radhi IJ, Koteva K, Kireeva I, Waglechner N, Wright GD. 2012. Bacterial Inactivation of the Anticancer Drug Doxorubicin. Chem Biol. 19(10):1255–1264.
  • Yu Z, Zhao L-X, Jiang C-L, Duan Y, Wong L, Carver KC, Schuler LA, Shen B. 2011. Bafilomycins produced by an endophytic actinomycete Streptomyces sp. YIM56209. J Antibiot. 64(1):159–162.

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