Niizalactams A-C, Multicyclic Macrolactams Isolated from Combined Culture of Streptomyces with Mycolic Acid-Containing Bacterium

Shotaro Hoshino; Masahiro Okada; Toshiyuki Wakimoto; Huiping Zhang; Fumiaki Hayashi; Hiroyasu Onaka; Ikuro Abe

doi:10.1021/acs.jnatprod.5b00804

Niizalactams A-C, Multicyclic Macrolactams Isolated from Combined Culture of Streptomyces with Mycolic Acid-Containing Bacterium

J Nat Prod. 2015 Dec 24;78(12):3011-7. doi: 10.1021/acs.jnatprod.5b00804. Epub 2015 Dec 1.

Authors

Shotaro Hoshino¹, Masahiro Okada¹, Toshiyuki Wakimoto¹, Huiping Zhang², Fumiaki Hayashi², Hiroyasu Onaka³, Ikuro Abe¹

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.

PMID: 26624939
DOI: 10.1021/acs.jnatprod.5b00804

Abstract

A terrestrial bacterium, Streptomyces sp. NZ-6, produced niizalactams A-C (1-3), unprecedented di- and tricyclic macrolactams, by coculturing with the mycolic acid-containing bacterium Tsukamurella pulmonis TP-B0596. Their complete structures, including absolute configurations, were elucidated on the basis of spectroscopic data and chemical derivatization. Their unique skeletons are proposed to be biosynthesized from a common 26-membered macrolactam intermediate by SN2 cyclization or an intramolecular Diels-Alder reaction.

Publication types

Research Support, Non-U.S. Gov't

MeSH terms

Animals
Bacillus subtilis / drug effects
Candida albicans / drug effects
Drug Screening Assays, Antitumor
Lactams, Macrocyclic / chemistry
Lactams, Macrocyclic / isolation & purification*
Lactams, Macrocyclic / pharmacology
Leukemia P388
Microbial Sensitivity Tests
Molecular Structure
Mycolic Acids / chemistry
Nuclear Magnetic Resonance, Biomolecular
Saccharomyces cerevisiae / drug effects
Streptomyces / chemistry*

Substances

Lactams, Macrocyclic
Mycolic Acids
niizalactam A
niizalactam B
niizalactam C