Nomimicin, a new spirotetronate-class polyketide from an actinomycete of the genus Actinomadura

Journal of Antibiotics

Volumn 65, Issue 7, 2012, Pages 355-359

  Igarashi, Yasuhiro ^a   Iida, Takako ^a   Oku, Naoya ^a   Watanabe, Hiroyuki ^b   Furihata, Kazuo ^c   Miyanouchi, Koji ^d  

^a TOYAMA PREFECTURAL UNIVERSITY   (Japan)

^b YOKOGAWA ANALYTICAL SYSTEMS INC   (Japan)

^c UNIVERSITY OF TOKYO   (Japan)

^d Bio Technical Research Industry Co Ltd   (Japan)

Author keywords

Actinomadura; polyketide; spirotetronate

Indexed keywords

ANTIBIOTIC AGENT; NOMIMICIN; UNCLASSIFIED DRUG;

ACTINOMADURA; ANTIMICROBIAL ACTIVITY; ARTICLE; CANDIDA ALBICANS; CYTOTOXICITY; DRUG ISOLATION; DRUG STRUCTURE; HETERONUCLEAR MULTIPLE BOND CORRELATION; HIGH PERFORMANCE LIQUID CHROMATOGRAPHY; HUMAN; HUMAN CELL; IC 50; KLUYVEROMYCES MARXIANUS; MICROCOCCUS LUTEUS; NONHUMAN; NUCLEAR MAGNETIC RESONANCE SPECTROSCOPY; NUCLEAR OVERHAUSER EFFECT; PRIORITY JOURNAL; STEREOCHEMISTRY;

ACTINOBACTERIA; ANTI-INFECTIVE AGENTS; CANDIDA ALBICANS; KLUYVEROMYCES; MAGNETIC RESONANCE SPECTROSCOPY; MICROBIAL SENSITIVITY TESTS; MICROCOCCUS LUTEUS; MOLECULAR SEQUENCE DATA; POLYKETIDES; RNA, RIBOSOMAL, 16S; SPECTRUM ANALYSIS;

ACTINOMADURA; CANDIDA; KLUYVEROMYCES MARXIANUS; MICROCOCCUS LUTEUS;

EID: 84864426788     PISSN: 00218820     EISSN: 18811469     Source Type: Journal    
DOI: 10.1038/ja.2012.30     Document Type: Article

References (17)

1. Butler, M. S. Natural products to drugs: Natural product-derived compounds in clinical trials. Nat. Prod. Rep. 25, 475-516 (2008).
2. Beacute;rdy, J. Bioactive microbial metabolites. J. Antibiot. 58, 1-26 (2005).
3. Smith, A. L. sNicolaou, K. C. The enediyne antibiotics. J. Med. Chem. 39, 2103-2117 (1996).
4. Walsh, T. J. Giri, N. Pradimicins: A novel class of broad-spectrum antifungal compounds. Eur. J. Clin. Microbiol. Infect. Dis. 16, 93-97 (1997).
5. Dirlam, J. P. et al. CP-84,657, a potent polyether anticoccidial related to portmicin and produced by Actinomadura sp. J. Antibiot. 43, 668-679 (1990).
6. Igarashi, Y. et al. Brartemicin, an inhibitor of tumor cell invasion from the actinomycete Nonomuraea sp. J. Nat. Prod 72, 980-982 (2009).
7. Igarashi, Y. et al. Maklamicin, an antibacterial polyketide from an endophytic Micromonospora sp. J. Nat. Prod. 74, 670-674 (2011).
8. Matsumori, N Kaneno, D Murata, M Nakamura, H. Tachibana, K. Stereochemical determination of acyclic structures based on carbon-proton spin-coupling constants. method of configuration analysis for natural products. J. Org. Chem. 64, 866-876 (1999).
9. Furihata, K. Seto, H. J-Resolved HMBC, a new NMR technique for measuring heteronuclear long-range coupling constants. Tetrahedron Lett. 40, 6271-6275 (1999).
10. Furihata, K Tashiro, M. Seto, H. Selective J-resolved HMBC, an efficient method for measuring heteronuclear long-range coupling constants. Magn. Reson. Chem. 47, 814-818 (2009).
11. Ohtani, I Kusumi, T Kashman, Y. Kakisawa, H. High-field FT NMR application of Mosher's method. The absolute configurations of marine terpenoids. J. Am. Chem. Soc. 113, 4092-4096 (1991).
12. Konno, K Fujishima, T Liu, Z. Takayama, H. Determination of absolute configuration of 1,3-diols by the modified Mosher's method using their di-MTPA esters. Chirality 13, 72-80 (2002).
13. Momose, I. et al. Decatromicins A and B, new antibiotics produced by Actinomadura sp. MK73-NF4. II. Structure determination. J. Antibiot. 52, 787-796 (1999).
14. Park, H-R Chijiwa, S Furihata, K Hayakawa, Y.Shin-ya, K. Relative and absolute configuration of versipelostatin, a down-regulator of olecular cha perone GRP78 expression. Org. Lett. 9, 1457-1460 (2007).
15. Mallams, A. K Puar, M. S Rossman, R. R McPhail, A. T. Macfarlane, R. D. Kijanimicin. 2. Structure and absolute stereochemistry of kijanimicin. J. Am. Chem. Soc. 103, 3940-3943 (1981).
16. Igarashi, Y. et al. Abyssomicin I, a modified polycyclic polyketide from Streptomyces sp. CHI39. J. Nat. Prod. 73, 1943-1946 (2010).
17. Fukuda, T. et al. Marianins A and B, prenylated phenylpropanoids from Mariannaea camptospora. J. Nat. Prod. 74, 1327-1330 (2011).