Cystargamides C and D, New Cyclic Lipopeptides From a Tidal Mudflat-Derived Streptomyces sp. JMS132

Jeongwon Seo; Yern-Hyerk Shin; Se Jin Jo; Young Eun Du; Soohyun Um; Young Ran Kim; Kyuho Moon

doi:10.3389/fmicb.2022.904954

Cystargamides C and D, New Cyclic Lipopeptides From a Tidal Mudflat-Derived Streptomyces sp. JMS132

Front Microbiol. 2022 May 13:13:904954. doi: 10.3389/fmicb.2022.904954. eCollection 2022.

Authors

Jeongwon Seo¹, Yern-Hyerk Shin², Se Jin Jo¹, Young Eun Du³, Soohyun Um⁴, Young Ran Kim¹, Kyuho Moon¹

Affiliations

¹ College of Pharmacy, Research Institute of Pharmaceutical Sciences, Chonnam National University, Gwangju, South Korea.
² Department of Biological Chemistry and Molecular Pharmacology, Harvard Medical School and Blavatnik Institute, Boston, MA, United States.
³ Natural Products Research Institute, College of Pharmacy, Seoul National University, Seoul, South Korea.
⁴ College of Pharmacy, Yonsei University, Incheon, South Korea.

Abstract

Cystargamides C and D (2 and 3) were isolated from a marine actinomycete strain collected at Beolgyo, South Korea. The planar structures of the cystargamides were elucidated by 1/2D NMR, UV, and MS spectroscopic analyses. The absolute configurations of 2 and 3 were determined based on ROESY correlations and the advanced Marfey's methods. The structures of the compounds were elucidated as new lipodepsipeptides bearing six amino acids with an epoxy fatty acid side chain. For the first time, the nonribosomal peptide synthetase biosynthetic pathway of the cystargamides has been proposed using whole genome sequence analysis. The cystargamides displayed antioxidant effect in the DPPH and ABTS assay. The discovery of new cyclic lipopeptides, cystargamides C and D, from a tidal mudflat-derived Streptomyces sp. supported that marine bacteria have potential as source of bioactive natural products.

Keywords: antioxidant activity; bacterial secondary metabolite; cystargamide; lipodepsipeptide; structural determination; tidal mudflat.