Mirilactams C–E, novel polycyclic macrolactams isolated from combined-culture of actinosynnema mirum NBRC 14064 and mycolic acid-containing bacterium

Shotaro Hoshino, Masahiro Ozeki, Chin Piow Wong, Huiping Zhang, Fumiaki Hayashi, Takayoshi Awakawa, Hiroyuki Morita, Hiroyasu Onaka, Ikuro Abe*

*Corresponding author for this work

Research output: Contribution to journalArticlepeer-review

20 Scopus citations

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).

Original languageEnglish
Pages (from-to)660-667
Number of pages8
JournalChemical and Pharmaceutical Bulletin
Volume66
Issue number6
DOIs
StatePublished - 2018

Keywords

  • Combined-culture
  • Mycolic acid-containing bacterium
  • Polyene macrolactam

ASJC Scopus subject areas

  • General Chemistry
  • Drug Discovery

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