Isolation and structure determination of a new antibacterial peptide pentaminomycin C from Streptomyces cacaoi subsp. cacaoi

Issara Kaweewan; Hikaru Hemmi; Hisayuki Komaki; Shinya Kodani

doi:10.1038/s41429-019-0272-y

Isolation and structure determination of a new antibacterial peptide pentaminomycin C from Streptomyces cacaoi subsp. cacaoi

J Antibiot (Tokyo). 2020 Apr;73(4):224-229. doi: 10.1038/s41429-019-0272-y. Epub 2020 Jan 10.

Authors

Issara Kaweewan¹, Hikaru Hemmi², Hisayuki Komaki³, Shinya Kodani^{4

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Affiliations

¹ Graduate School of Science and Technology, Shizuoka University, Shizuoka, Japan.
² Food Research Institute, National Agriculture and Food Research Organization (NARO), Ibaraki, Japan.
³ Biological Resource Center, National Institute of Technology and Evaluation (NBRC), Chiba, Japan.
⁴ Graduate School of Science and Technology, Shizuoka University, Shizuoka, Japan. kodani.shinya@shizuoka.ac.jp.
⁵ Graduate School of Integrated Science and Technology, Shizuoka University, Shizuoka, Japan. kodani.shinya@shizuoka.ac.jp.
⁶ Academic Institute, Shizuoka University, Shizuoka, Japan. kodani.shinya@shizuoka.ac.jp.

PMID: 31919422
DOI: 10.1038/s41429-019-0272-y

Abstract

A new antibacterial peptide named pentaminomycin C was isolated from an extract of Streptomyces cacaoi subsp. cacaoi NBRC 12748^T, along with a known peptide BE-18257A. Pentaminomycin C was determined to be a cyclic pentapeptide containing an unusual amino acid, Nδ-hydroxyarginine (5-OHArg), by a combination of ESI-MS and NMR analyses. The structure of pentaminomycin C was determined to be cyclo(-L-Leu-D-Val-L-Trp-L-5-OHArg-D-Phe-). Pentaminomycin C exhibited antibacterial activities against Gram-positive bacteria including Micrococcus luteus, Bacillus subtilis, and Staphylococcus aureus. The biosynthetic gene cluster for pentaminomycin C and BE-18257A was identified from the genome sequence data of S. cacaoi subsp. cacaoi.

Publication types

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

MeSH terms

Anti-Bacterial Agents / chemistry
Anti-Bacterial Agents / isolation & purification*
Anti-Bacterial Agents / pharmacology
Gram-Positive Bacteria / drug effects*
Magnetic Resonance Spectroscopy
Multigene Family
Spectrometry, Mass, Electrospray Ionization
Streptomyces / chemistry*
Streptomyces / genetics

Substances

Anti-Bacterial Agents

Supplementary concepts

Streptomyces cacaoi