Isolation and structure determination of a new lantibiotic cinnamycin B from Actinomadura atramentaria based on genome mining

Shinya Kodani; Hisayuki Komaki; Sho Ishimura; Hikaru Hemmi; Mayumi Ohnishi-Kameyama

doi:10.1007/s10295-016-1788-9

Isolation and structure determination of a new lantibiotic cinnamycin B from Actinomadura atramentaria based on genome mining

J Ind Microbiol Biotechnol. 2016 Aug;43(8):1159-65. doi: 10.1007/s10295-016-1788-9. Epub 2016 Jun 2.

Authors

Shinya Kodani^{1

2

3}, Hisayuki Komaki⁴, Sho Ishimura⁵, Hikaru Hemmi⁶, Mayumi Ohnishi-Kameyama⁶

Affiliations

¹ College of Agriculture, Academic Institute, Shizuoka University, 836 Ohya, Suruga-ku, Shizuoka, 422-8529, Japan. kodani.shinya@shizuoka.ac.jp.
² Graduate School of Integrated Science and Technology, Shizuoka University, 836 Ohya, Suruga-ku, Shizuoka, 422-8529, Japan. kodani.shinya@shizuoka.ac.jp.
³ Graduate School of Science and Technology, Shizuoka University, 836 Ohya, Suruga-ku, Shizuoka, 422-8529, Japan. kodani.shinya@shizuoka.ac.jp.
⁴ Biological Resource Center, National Institute of Technology and Evaluation (NBRC), 2-5-8 Kazusakamatari, Kisarazu, Chiba, 292‒0818, Japan.
⁵ Graduate School of Integrated Science and Technology, Shizuoka University, 836 Ohya, Suruga-ku, Shizuoka, 422-8529, Japan.
⁶ Food Research Institute, NARO, 2-1-12 Kan-nondai, Tsukuba, Ibaraki, 305-8642, Japan.

PMID: 27255974
DOI: 10.1007/s10295-016-1788-9

Abstract

New lantibiotic cinnamycin B was isolated from the extract of Actinomadura atramentaria NBRC 14695(T), based on genome mining and chemical investigation. The partial structure of cinnamycin B was established by 2D NMR experiments, which indicated that cinnamycin B had same methyl lanthionine bridging pattern with cinnamycin. The reduction with NaBH4-NiCl2 afforded the reduced cinnamycin B, and MS/MS experiment indicated the presence of hydroxy asparatic acid in the molecule. Cinnamycin B showed an antibacterial activity against Streptomyces antibioticus with dosage of 5 μg (0.5μL, 10 mg/mL solution) at spot-on-lawn testing method. The gene cluster of cinnamycin B on the genome of A. atramentaria was identified and discussed in comparison with that of cinnamycin.

Keywords: Actinomadura atramentaria NBRC 14695; Genome mining; Lantibiotic; MS/MS analysis; NMR spectrum.

MeSH terms

Actinomycetales / chemistry*
Actinomycetales / genetics
Actinomycetales / metabolism
Anti-Bacterial Agents / chemistry*
Anti-Bacterial Agents / isolation & purification
Anti-Bacterial Agents / metabolism
Anti-Bacterial Agents / pharmacology
Bacteriocins / biosynthesis
Bacteriocins / chemistry*
Bacteriocins / isolation & purification
Bacteriocins / metabolism
Bacteriocins / pharmacology
Data Mining
Genome, Bacterial
Genomics
Peptides, Cyclic / chemistry

Substances

Anti-Bacterial Agents
Bacteriocins
Peptides, Cyclic
cinnamycin B
cinnamycin