Isolation and structure determination of new linear azole-containing peptides spongiicolazolicins A and B from Streptomy
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BIOTECHNOLOGICAL PRODUCTS AND PROCESS ENGINEERING
Isolation and structure determination of new linear azole-containing peptides spongiicolazolicins A and B from Streptomyces sp. CWH03 Mana Suzuki 1 & Hisayuki Komaki 2 & Issara Kaweewan 3 & Hideo Dohra 1,4,5 & Hikaru Hemmi 6 & Hiroyuki Nakagawa 6,7 & Hideki Yamamura 8 & Masayuki Hayakawa 8 & Shinya Kodani 1,3,5 Received: 27 August 2020 / Revised: 2 November 2020 / Accepted: 9 November 2020 # Springer-Verlag GmbH Germany, part of Springer Nature 2020
Abstract Linear azole-containing peptides are a class of ribosomally synthesized and post-translationally modified peptides. We performed a chemical investigation on marine actinomycetes, and new linear azole-containing peptides named spongiicolazolicins A and B were found in the MeOH extracts of a newly isolated strain Streptomyces sp. CWH03 (NBRC 114659) and two strains of S. spongiicola (strain HNM0071T: DSM 103383T and strain 531S: NBRC 113560). The strain Streptomyces sp. CWH03 was indicated to be a new species closely related to S. spongiicola by phylogenetic analysis using the genome sequence. The new peptides named spongiicolazolicins A and B were isolated from the cell of Streptomyces sp. CWH03. The partial structure of spongiicolazolicin A was determined by 2D NMR experiments. Based on data of MS/MS experiments, the chemical structures of spongiicolazolicins A and B were proposed using the amino acid sequence deduced from the precursor-encoding gene, which was found from whole-genome sequence data of Streptomyces sp. CWH03. The biosynthetic gene cluster of spongiicolazolicins was proposed based on comparative analysis with that of a known linear azole peptide goadsporin. Key points • Streptomyces sp. CWH03 was a new species isolated from marine sediment. • New linear azole-containing peptides named spongiicolazolicins A and B were isolated. • Biosynthetic pathway of spongiicolazolicins was proposed. Keywords Linear azole-containing peptide . NMR . MS/MS . Biosynthesis . Streptomyces spongiicola
* Shinya Kodani [email protected] 1
Graduate School of Integrated Science and Technology, Shizuoka University, Shizuoka, Japan
2
Biological Resource Center, National Institute of Technology and Evaluation (NBRC), Chiba, Japan
3
Graduate School of Science and Technology, Shizuoka University, Shizuoka, Japan
4
Research Institute of Green Science and Technology, Shizuoka University, Shizuoka, Japan
5
Academic Institute, Shizuoka University, Shizuoka, Japan
6
Food Research Institute, National Agriculture and Food Research Organization (NARO), Ibaraki, Japan
7
Advanced Analysis Center, National Agriculture and Food Research Organization (NARO), Ibaraki, Japan
8
Interdisciplinary Graduate School of Medicine and Engineering, University of Yamanashi, Yamanashi, Japan
Introduction Ribosomally synthesized and post-translationally modified peptides (RiPPs) are a class of naturally occurring peptides that are classified into several groups, such as lanthipeptides (McAuliffe et al. 2001; Willey and van d
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