Cytotoxic and antibacterial angucycline- and prodigiosin-analogues from the deep-sea derived Streptomyces sp. SCSIO 11594

Marine Drugs

Volumn 13, Issue 3, 2015, Pages 1304-1316

  Song, Yongxiang ^a   Liu, Guangfu ^b   Li, Jie ^a   Huang, Hongbo ^a   Zhang, Xing ^a   Zhang, Hua ^b   Ju, Jianhua ^a  

^a SOUTH CHINA SEA INSTITUTE OF OCEANOLOGY   (China)

^b GUANGDONG MEDICAL UNIVERSITY   (China)

Author keywords

Antibacterial; Cytotoxicity; Deep sea; Marangucyclines; Streptomyces sp. SCSIO 11594

Indexed keywords

ANGUCYCLINE DERIVATIVE; ANTIINFECTIVE AGENT; CISPLATIN; DEHYDROXYAQUAYAMYCIN; MARANGUCYCLINE A; MARANGUCYCLINE B; METACYCLOPRODIGIOSIN; PRODIGIOSIN; UNCLASSIFIED DRUG; UNDECYLPRODIGIOSIN; ANTINEOPLASTIC AGENT; C-GLYCOSIDE; MONOSACCHARIDE;

ANTIBACTERIAL ACTIVITY; ANTINEOPLASTIC ACTIVITY; ARTICLE; CANCER CELL LINE; CARBON NUCLEAR MAGNETIC RESONANCE; CONTROLLED STUDY; DRUG CYTOTOXICITY; DRUG DETERMINATION; DRUG SCREENING; DRUG STRUCTURE; ENTEROCOCCUS FAECALIS; HUMAN; HUMAN CELL; IC50; IN VITRO STUDY; METHICILLIN-RESISTANT STAPHYLOCOCCUS EPIDERMIDIS; MINIMUM INHIBITORY CONCENTRATION; NONHUMAN; NUCLEOTIDE SEQUENCE; PROTON NUCLEAR MAGNETIC RESONANCE; STREPTOMYCES; STREPTOMYCES RUBROGRISEUS; ANALOGS AND DERIVATIVES; CHEMISTRY; COMPARATIVE STUDY; ISOLATION AND PURIFICATION; MICROBIAL SENSITIVITY TEST; NEOPLASMS; NUCLEAR MAGNETIC RESONANCE SPECTROSCOPY; PATHOLOGY; TUMOR CELL LINE;

ENTEROCOCCUS FAECALIS; STAPHYLOCOCCUS EPIDERMIDIS; STREPTOMYCES SP.;

ANTI-BACTERIAL AGENTS; ANTINEOPLASTIC AGENTS; CELL LINE, TUMOR; CISPLATIN; HUMANS; INHIBITORY CONCENTRATION 50; MAGNETIC RESONANCE SPECTROSCOPY; MICROBIAL SENSITIVITY TESTS; MONOSACCHARIDES; NEOPLASMS; PRODIGIOSIN; STREPTOMYCES;

EID: 84925882714     PISSN: None     EISSN: 16603397     Source Type: Journal    
DOI: 10.3390/md13031304     Document Type: Article

References (32)

1. Xiong, Z. Q.; Wang, J. F.; Hao, Y. Y.; Wang, Y. Recent advances in the discovery and development of marine microbial natural products. Mar. Drugs 2013, 11, 700-717.
2. Eom, S. H.; Kim, Y. M.; Kim, S. K. Marine bacteria: Potential sources for compounds to overcome antibiotic resistance. Appl. Microbiol. Biotechnol. 2013, 97, 4763-4773.
3. Cheung, R. C.; Wong, J. H.; Pan, W. L.; Chan, Y. S.; Yin, C. M.; Dan, X. L.; Wang, H. X.; Fang, E. F.; Lam, S. K.; Ngai, P. H.; et al. Antifungal and antiviral products of marine organisms. Appl. Microbiol. Biotechnol. 2014, 98, 3475-3494.
4. Skropeta, D. Deep-sea natural products. Nat. Prod. Rep. 2008, 25, 1131-1166.
5. Skropeta, D.; Wei, L. Recent advances in deep-sea natural products. Nat. Prod. Rep. 2014, 31, 999-1025.
6. Berdy, J. Bioactive microbial metabolites. J. Antibiot. 2005, 58, 1-26.
7. Lam, K. S. Discovery of novel metabolites from marine actinomycetes. Curr. Opin. Microbiol. 2006, 9, 245-251.
8. Zotchev, S. B. Marine actinomycetes as an emerging resource for the drug development pipelines. J. Biotechnol. 2012, 158, 168-175.
9. Subramani, R.; Aalbersberg, W. Marine actinomycetes: An ongoing source of novel bioactive metabolites. Microbiol. Res. 2012, 167, 571-580.
10. Zhou, X.; Huang, H.; Chen, Y.; Tan, J.; Song, Y.; Zou, J.; Tian, X.; Hua, Y.; Ju, J. Marthiapeptide A, an anti-infective and cytotoxic polythiazole cyclopeptide from a 60 L scale fermentation of the deep sea-derived Marinactinospora thermotolerans SCSIO 00652. J. Nat. Prod. 2012, 75, 2251-2255.
11. Huang, H.; Yao, Y.; He, Z.; Yang, T.; Ma, J.; Tian, X.; Li, Y.; Huang, C.; Chen, X.; Li, W.; et al. Antimalarial β-carboline and indolactam alkaloids from Marinactinospora thermotolerans, a deep sea isolate. J. Nat. Prod. 2011, 74, 2122-2127.
12. Song, Y.; Li, Q.; Liu, X.; Chen, Y. C.; Zhang, Y.; Sun, A.; Zhang, W.; Zhang, J.; Ju, J. Cyclic hexapeptides from the deep South China Sea-derived Streptomyces scopuliridis SCSIO ZJ46 active against pathogenic Gram-positive Bacteria. J. Nat. Prod. 2014, 77, 1937-1941.
13. Zhou, X.; Huang, H.; Li, J.; Song, Y.; Jiang, R.; Liu, J.; Zhang, S.; Hua, Y.; Ju, J. New anti-infective cycloheptadepsipeptide congeners and absolute stereochemistry from the deep sea-derived Streptomyces drozdowiczii SCSIO 10141. Tetrahedron 2014, 70, 7795-7801.
14. Supong, K.; Thawai, C.; Suwanborirux, K.; Choowong, W.; Supothina, S.; Pittayakhajonwut, P. Antimalarial and antitubercular C-glycosylated benz[α]anthraquinones from the marine-derived Streptomyces sp. BCC45596. Phytochem. Lett. 2012, 5, 651-656.
15. Sezaki, M.; Kondo, S.; Maeda, K.; Umezawa, H.; Ono, M. The structure of aquayamycin. Tetrahedron 1970, 26, 5171-5190.
16. Kuntsmann, M. P.; Mitscher, L. A. The structural characterization of tetrangomycin and tetrangulol. J. Org. Chem. 1966, 31, 2920-2925.
17. Rohr, J.; Thiericke, R. Angucycline group antibiotics. Nat. Prod. Rep. 1992, 9, 103-137.
18. Oki, T.; Kitamura, I.; Matsuzawa, Y.; Shibamoto, N.; Ogasawara, T.; Yoshimoto, A.; Inui, T.; Naganawa, H.; Takeuchi, T.; Umezawa, H. Anti-tumor anthracycline antibiotics, aclacinomycin-A and analogs. 2. structural determination. J. Antibiot. 1979, 32, 801-819.
19. Huang, H.; Yang, T.; Ren, X.; Liu, J.; Song, Y.; Sun, A.; Ma, J.; Wang, B.; Zhang, Y.; Huang, C.; et al. Cytotoxic angucycline class glycosides from the deep sea actinomycete Streptomyces lusitanus SCSIO LR32. J. Nat. Prod. 2012, 75, 202-208.
20. Liu, R.; Cui, C. B.; Duan, L.; Gu, Q. Q.; Zhu, W. M. Potent in vitro anticancer activity of metacycloprodigiosin and undecylprodigiosin from a sponge-derived actinomycete Saccharopolyspora sp. nov. Arch. Pharm. Res. 2005, 28, 1341-1344.
21. Abdelfattah, M. S.; Kharel, M. K.; Hitron, J. A.; Baig, I.; Rohr, J. Moromycins A and B, isolation and structure elucidation of C-glycosylangucycline-type antibiotics from Streptomyces sp. KY002. J. Nat. Prod. 2008, 71, 1569-1573.
22. Omura, S.; Tanaka, H.; Oiwa, R.; Awaya, J.; Masuma, R.; Tanaka, K. New antitumor antibiotics, OS-4742 A1, A2, B1 and B2 produced by a strain of Streptomyces. J. Antibiot. 1977, 30, 908-916.
23. Imamura, N.; Kakinuma, K.; Ikekawa, N.; Tanaka, H.; Omura, S. The structure of vineomycin B2. J. Antibiot. 1981, 34, 1517-1518.
24. Imamura, N.; Kakinuma, K.; Ikekawa, N.; Tanaka, H.; Omura, S. Biosynthesis of vineomycins A1 and B2. J. Antibiot. 1982, 35, 602-608.
25. Morton, G. E.; Barrett, A. G. M. Iterative benzyne-furan cycloaddition reactions: Studies toward the total synthesis of ent-Sch 47554 and ent-Sch 47555. Org. Lett. 2006, 8, 2859-2861.
26. Sobti, A.; Kim, K. J.; Sulikowski, G. A. Application of glycosyltetrazoles in oligosaccharide synthesis: Assembly of the C3 trisaccharide component of the antibiotic PI-080. J. Org. Chem. 1996, 61, 6-7.
27. Yu, X.; O'Doherty, G. A. De novo asymmetric synthesis and biological evaluation of the trisaccharide portion of PI-080 and vineomycin B2. Org. Lett. 2008, 10, 4529-4532.
28. Yu, X. M.; Li, M. S.; O'doherty, G. A. De novo asymmetric approach to the disaccharide portion of Sch-47554. Heterocycles 2011, 82, 1577-1584.
29. You, Z. Q.; Li, J.; Qin, S.; Tian, X. P.; Wang, F. Z.; Zhang, S. Georgenia sediminis sp. nov. a moderately thermophilic actinobacterium isolated from sediment. Int. J. Syst. Evol. Microbiol. 2013, 63, 4243-4247.
30. Mosmann, T. Rapid colorimetric assay for cellular growth and survival: Application to proliferation and cytotoxicity assays. J. Immunol. Methods 1983, 65, 55-63.
31. CLSI. Methods for Dilution Antimicrobial Susceptibility Tests for Bacteria That Grow Aerobically, Approved Standard-8th ed.; Clinical and Laboratory Standards Institute: Wayne, PA, USA, 2009; pp. M07-A8.
32. Song, Y.; Huang, H.; Chen, Y.; Ding, J.; Zhang, Y.; Sun, A.; Zhang, W.; Ju, J. Cytotoxic and antibacterial marfuraquinocins from the deep South China Sea-derived Streptomyces niveus SCSIO 3406. J. Nat. Prod. 2013, 76, 2263-2268.