Mirilactams C–E, Novel Polycyclic Macrolactams Isolated from Combined-Culture of <i>Actinosynnema mirum</i> NBRC 14064 and Mycolic Acid-Containing Bacterium

• Hoshino Shotaro

  Graduate School of Pharmaceutical Sciences, The University of Tokyo

• Ozeki Masahiro

  Graduate School of Pharmaceutical Sciences, The University of Tokyo

• Wong Chin Piow

  Institute of Natural Medicine, University of Toyama

• Zhang Huiping

  RIKEN Center for Life Science Technologies

• Hayashi Fumiaki

  RIKEN Center for Life Science Technologies

• Awakawa Takayoshi

  Graduate School of Pharmaceutical Sciences, The University of Tokyo

• Morita Hiroyuki

  RIKEN Center for Life Science Technologies

• Onaka Hiroyasu

  Graduate School of Agricultural and Life Sciences, The University of Tokyo

• Abe Ikuro

  Graduate School of Pharmaceutical Sciences, The University of Tokyo

Bibliographic Information

Other Title

• Highlighted Paper selected by Editor-in-Chief : Mirilactams C-E, Novel Polycyclic Macrolactams Isolated from Combined-Culture of Actinosynnema mirum NBRC 14064 and Mycolic Acid-Containing Bacterium
• Mirilactams C-E, novel polycyclic macrolactams isolated from combined-culture of Actinosynnema mirum NBRC 14064 and mycolic acid-containing bacterium

Abstract

Mycolic acid-containing bacteria (MACB) are known to activate cryptic natural product biosynthesis in co-cultures with actinobacteria. We cultured Actinosynnema mirum NBRC 14064, a producer of the mono-cyclic polyene macrolactam mirilactam A (6), with the MACB Tsukamurella pulmonis TP-B0596. As a result, three novel compounds (mirilactams C–E, 1–3) were produced in the co-culture conditions. Compounds 1–3 were likely derived from 6 by epoxidation and subsequent spontaneous cyclization. The chemical structures and stereochemistries of 1–3 were determined by spectroscopic analyses (NMR and MS), conformational searches in the optimized potentials for liquid simulations-3 (OPLS3) force field, and calculations of electronic circular dichroism (ECD).

Journal

• Chemical and Pharmaceutical Bulletin

  Chemical and Pharmaceutical Bulletin 66 (6), 660-667, 2018-06-01

  The Pharmaceutical Society of Japan

Keywords

• mycolic acid-containing bacterium
• combined-culture
• polyene macrolactam

Details

• CRID: 1390282763013079424
• NII Article ID: 130007382327
• NII Book ID: AA00602100
• DOI: 10.1248/cpb.c18-00143
• ISSN: 13475223
• ISSN: 00092363
• NDL BIB ID: 029007108
• PubMed: 29863068
• Web Site: https://ndlsearch.ndl.go.jp/books/R000000004-I029007108
• Web Site: https://www.jstage.jst.go.jp/article/cpb/66/6/66_c18-00143/_pdf
• Web Site: https://search.jamas.or.jp/link/ui/2019071609
• Text Lang: en
• Data Source:
  • JaLC
  • NDL
  • Crossref
  • PubMed
  • CiNii Articles
  • KAKEN
• Abstract License Flag: Disallowed