Umezawamides, new bioactive polycyclic tetramate macrolactams isolated from a combined-culture of Umezawaea sp. and mycolic acid-containing bacterium

Shotaro Hoshino; Chin Piow Wong; Masahiro Ozeki; Huiping Zhang; Fumiaki Hayashi; Takayoshi Awakawa; Shumpei Asamizu; Hiroyasu Onaka; Ikuro Abe

doi:10.1038/s41429-018-0040-4

Umezawamides, new bioactive polycyclic tetramate macrolactams isolated from a combined-culture of Umezawaea sp. and mycolic acid-containing bacterium

J Antibiot (Tokyo). 2018 Jul;71(7):653-657. doi: 10.1038/s41429-018-0040-4. Epub 2018 Mar 14.

Authors

Shotaro Hoshino¹, Chin Piow Wong¹, Masahiro Ozeki¹, Huiping Zhang², Fumiaki Hayashi², Takayoshi Awakawa¹, Shumpei Asamizu³, Hiroyasu Onaka³, Ikuro Abe⁴

Affiliations

¹ Graduate School of Pharmaceutical Sciences, The University of Tokyo, Bunkyo-ku, Tokyo, 113-0033, Japan.
² RIKEN Center for Life Science Technologies, 1-7-22, Suehiro-cho, Tsurumi-ku, Yokohama, 230-0045, Japan.
³ Graduate School of Agricultural and Life Sciences, The University of Tokyo, Bunkyo-ku, Tokyo, 113-8657, Japan.
⁴ Graduate School of Pharmaceutical Sciences, The University of Tokyo, Bunkyo-ku, Tokyo, 113-0033, Japan. abei@mol.f.u-tokyo.ac.jp.

PMID: 29540776
DOI: 10.1038/s41429-018-0040-4

Abstract

New polycyclic tetramate macrolactams, Umezawamides A (1) and B (2) were isolated from a combined-culture of Umezawaea sp. RD066910 and mycolic-acid containing bacterium Tsukamurella pulmonis TP-B0596. Their planar structures and partial stereochemistries were determined based on the spectroscopic analysis, MMFF conformational search, and ECD calculations. Umezawamides are the first secondary metabolites isolated from the genus Umezawaea and they exhibited cytotoxicities to P388 murine leukemia cells. Furthermore, umezawamide A (1) showed growth inhibitory activity against Candida albicans.

MeSH terms

Actinomycetales / chemistry*
Animals
Anti-Bacterial Agents / chemistry*
Anti-Bacterial Agents / isolation & purification*
Anti-Bacterial Agents / pharmacology
Antibiotics, Antineoplastic / chemistry
Antibiotics, Antineoplastic / isolation & purification
Antibiotics, Antineoplastic / pharmacology
Antifungal Agents / chemistry
Antifungal Agents / isolation & purification
Antifungal Agents / pharmacology
Bacteria / drug effects
Candida albicans / drug effects
Cell Line, Tumor
Humans
Lactams, Macrocyclic / isolation & purification*
Lactams, Macrocyclic / pharmacology*
Leukemia P388 / drug therapy
Mice
Microbial Sensitivity Tests
Molecular Conformation
Mycolic Acids / metabolism*
Polycyclic Compounds / isolation & purification*
Polycyclic Compounds / pharmacology*

Substances

Anti-Bacterial Agents
Antibiotics, Antineoplastic
Antifungal Agents
Lactams, Macrocyclic
Mycolic Acids
Polycyclic Compounds